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Classic Winchester charm awaits at 310 Bellview Avenue! This inviting Cape Cod combines character, convenience, and plenty of opportunity to make the space your own. Inside, you’ll find hardwood floors, comfortable living areas, two main-level bedrooms, a full bathroom, and an additional half bath upstairs. A full basement offers extra storage and future possibilities, while the detached one-car garage provides even more room for parking, hobbies, or equipment. Out back, the spacious yard gives you room to relax, garden, entertain, or create the outdoor space you’ve been envisioning. With shopping, dining, parks, and Winchester amenities nearby, this home is ready for its next chapter.

2 Beds ⋅ 1 Baths

Classic Winchester charm awaits at 310 Bellview Avenue! This inviting Cape Cod combines character, convenience, and plenty of opportunity to make the space your own. Inside, you’ll find hardwood floors, comfortable living areas, two main-level bedrooms, a full bathroom, and an additional half bath upstairs. A full basement offers extra storage and future possibilities, while the detached one-car garage provides even more room for parking, hobbies, or equipment. Out back, the spacious yard gives you room to relax, garden, entertain, or create the outdoor space you’ve been envisioning. With shopping, dining, parks, and Winchester amenities nearby, this home is ready for its next chapter.

310 Bellview Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact:

$735,000

Exceptional space, thoughtful updates, and tremendous future potential come together in this impressive home! With a brand-new HVAC system, freshly painted interior and exterior, a freshly painted deck, and beautifully refreshed hardwood floors in the living room, much of the work has already been done for the next owner. Seller has obtained a recent professional appraisal; contact listing agent for additional information.” Step inside to a bright and welcoming interior where fresh paint gives the home a clean, updated feel. The living room features newly varnished hardwood floors, adding warmth and character to the space. The home's generous layout provides plenty of room for comfortable everyday living as well as entertaining. One of the property's most exciting features is the expansive unfinished lower level. With extensive framing already in place, this impressive space offers tremendous possibilities for future finishing. Imagine a recreation room, home theater, fitness area, home office, hobby space, guest accommodations, additional storage—or a combination of uses. Existing plumbing and mechanical components further add to the possibilities and allow buyers to envision creating a lower level tailored specifically to their needs. The outdoor living spaces are equally impressive. A large, freshly painted rear deck provides plenty of room for outdoor dining, entertaining, or simply relaxing while overlooking the backyard. Multiple covered brick porch and patio areas create even more usable outdoor space. The spacious fenced backyard is bordered by mature trees, offering a wonderful combination of privacy, open lawn, and wooded views. Additional highlights include the home's attractive brick exterior, architectural arches, numerous windows and doors providing abundant natural light, and convenient connections between the indoor and outdoor living areas. With a brand-new HVAC system, fresh interior and exterior paint, newly varnished living room floors, refreshed deck, expansive unfinished lower level, and generous outdoor living spaces, this home offers an outstanding combination of immediate improvements and exciting possibilities for the future. Move in, make it your own, and enjoy all the space this exceptional property has to offer! Bring your ideas and imagine the possibilities this exceptional property has to offer! Convenient access to Winchester Transit and WinReady on-demand transportation, with nearby service connecting residents to Downtown Winchester, Winchester Medical Center and other destinations throughout the city. The location also offers convenient access to I-81, Route 7, Route 50, Route 37, US-11 and US-522 for travel throughout the Shenandoah Valley and Northern Virginia.

3 Beds ⋅ 3 Baths

Exceptional space, thoughtful updates, and tremendous future potential come together in this impressive home! With a brand-new HVAC system, freshly painted interior and exterior, a freshly painted deck, and beautifully refreshed hardwood floors in the living room, much of the work has already been done for the next owner. Seller has obtained a recent professional appraisal; contact listing agent for additional information.” Step inside to a bright and welcoming interior where fresh paint gives the home a clean, updated feel. The living room features newly varnished hardwood floors, adding warmth and character to the space. The home's generous layout provides plenty of room for comfortable everyday living as well as entertaining. One of the property's most exciting features is the expansive unfinished lower level. With extensive framing already in place, this impressive space offers tremendous possibilities for future finishing. Imagine a recreation room, home theater, fitness area, home office, hobby space, guest accommodations, additional storage—or a combination of uses. Existing plumbing and mechanical components further add to the possibilities and allow buyers to envision creating a lower level tailored specifically to their needs. The outdoor living spaces are equally impressive. A large, freshly painted rear deck provides plenty of room for outdoor dining, entertaining, or simply relaxing while overlooking the backyard. Multiple covered brick porch and patio areas create even more usable outdoor space. The spacious fenced backyard is bordered by mature trees, offering a wonderful combination of privacy, open lawn, and wooded views. Additional highlights include the home's attractive brick exterior, architectural arches, numerous windows and doors providing abundant natural light, and convenient connections between the indoor and outdoor living areas. With a brand-new HVAC system, fresh interior and exterior paint, newly varnished living room floors, refreshed deck, expansive unfinished lower level, and generous outdoor living spaces, this home offers an outstanding combination of immediate improvements and exciting possibilities for the future. Move in, make it your own, and enjoy all the space this exceptional property has to offer! Bring your ideas and imagine the possibilities this exceptional property has to offer! Convenient access to Winchester Transit and WinReady on-demand transportation, with nearby service connecting residents to Downtown Winchester, Winchester Medical Center and other destinations throughout the city. The location also offers convenient access to I-81, Route 7, Route 50, Route 37, US-11 and US-522 for travel throughout the Shenandoah Valley and Northern Virginia.

1748 Handley Ave, Winchester

Listing courtesy of RE/MAX Real Estate Connections. Contact:

$748,900

Classic all-brick home in a highly desirable Winchester location! Well maintained and thoughtfully designed, this five bedroom, three full bath home offers timeless character, spacious living areas and exceptional convenience. The main level features a gracious living room with fireplace, cozy den with fireplace and bookshelves and a primary bedroom on the main level. Four additional bedrooms provide excellent flexibility for family or guests. The finished basement offers valuable living and recreational space. Outside, enjoy the beautifully landscaped level lot and inviting brick patio. Two car garage. Ideally situated within walking distance to Handley High School and downtown Winchester.

5 Beds ⋅ 3 Baths

Classic all-brick home in a highly desirable Winchester location! Well maintained and thoughtfully designed, this five bedroom, three full bath home offers timeless character, spacious living areas and exceptional convenience. The main level features a gracious living room with fireplace, cozy den with fireplace and bookshelves and a primary bedroom on the main level. Four additional bedrooms provide excellent flexibility for family or guests. The finished basement offers valuable living and recreational space. Outside, enjoy the beautifully landscaped level lot and inviting brick patio. Two car garage. Ideally situated within walking distance to Handley High School and downtown Winchester.

416 Briarmont Dr, Winchester

Listing courtesy of Colony Realty. Contact:

$499,900

Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special. Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to its original central location within the home, where restored handmade cabinets were thoughtfully combined with new cabinetry and African Mahogany open shelving. The ceiling was raised and a dormer added to bring in additional natural light, while original brick was exposed on two walls. Reclaimed original wood was given new life throughout the space, creating beautiful beams, trim, and a distinctive vent hood. A dedicated coffee area with bar sink adds both function and charm. The main living spaces were opened up by removing the wall between the entry hall and living room, while the doorway to the restored kitchen was widened to create an inviting, connected floor plan. The fireplace was enhanced with gas logs, and even a trap door adds an unexpected touch of history and character. Original hard pine floors in the living room and kitchen were carefully restored, preserving the warmth and authenticity of the home. A new Dutch door welcomes you at the front entrance. The 2025 renovation also brought extensive structural and mechanical improvements, including a new metal roof, new gas furnace, new air conditioning system, upgraded 200-amp electrical service, and a repointed and reinforced brick foundation. A 22' x 16' addition expands the living space and features durable board-and-batten metal siding. Outdoor living was thoughtfully designed as well, with a new 22' x 10' deck featuring wire railing. The space beneath the deck includes a concrete pad and has been waterproofed, creating additional usable outdoor living space. A separate 22' x 9'9" concrete pad has also been added and prepped for electrical, ready for a future hot tub. From the original brick and restored floors to the reclaimed wood details and preserved architectural elements, small pieces of the home's history have been intentionally saved throughout. Every update was completed with an appreciation for what came before, resulting in a home that feels both historic and fresh. With its downtown Winchester location, extensive 2025 renovation, and rare combination of historic craftsmanship and modern amenities, this is a home that truly offers the best of both worlds.

3 Beds ⋅ 3 Baths

Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special. Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to its original central location within the home, where restored handmade cabinets were thoughtfully combined with new cabinetry and African Mahogany open shelving. The ceiling was raised and a dormer added to bring in additional natural light, while original brick was exposed on two walls. Reclaimed original wood was given new life throughout the space, creating beautiful beams, trim, and a distinctive vent hood. A dedicated coffee area with bar sink adds both function and charm. The main living spaces were opened up by removing the wall between the entry hall and living room, while the doorway to the restored kitchen was widened to create an inviting, connected floor plan. The fireplace was enhanced with gas logs, and even a trap door adds an unexpected touch of history and character. Original hard pine floors in the living room and kitchen were carefully restored, preserving the warmth and authenticity of the home. A new Dutch door welcomes you at the front entrance. The 2025 renovation also brought extensive structural and mechanical improvements, including a new metal roof, new gas furnace, new air conditioning system, upgraded 200-amp electrical service, and a repointed and reinforced brick foundation. A 22' x 16' addition expands the living space and features durable board-and-batten metal siding. Outdoor living was thoughtfully designed as well, with a new 22' x 10' deck featuring wire railing. The space beneath the deck includes a concrete pad and has been waterproofed, creating additional usable outdoor living space. A separate 22' x 9'9" concrete pad has also been added and prepped for electrical, ready for a future hot tub. From the original brick and restored floors to the reclaimed wood details and preserved architectural elements, small pieces of the home's history have been intentionally saved throughout. Every update was completed with an appreciation for what came before, resulting in a home that feels both historic and fresh. With its downtown Winchester location, extensive 2025 renovation, and rare combination of historic craftsmanship and modern amenities, this is a home that truly offers the best of both worlds.

510 S Cameron St, Winchester

Listing courtesy of Samson Properties. Contact:

$471,000

A must see property! This is a beautifull well kept colonial house with 3 bedrooms, 2 full bath and 1 half bath. The basement is unfinish but is ready to be build. As you enter the main level, you will see a nice welcoming livingroom, diningroom and beautiful granite countertops in the kitchen, with stainless steel appliances and high effitiency washer and dryer to the side. From the kitchen you can easily walkout to a huge concrete patio for a great family cookout and joyful huge backyard. The back yard is infenced with 6ft tall white vinyl privacy fence that makes it look very elegant and secured... In the upper level of the house, you will find the masterbedroom with a masterbath, and a second bath for the 2 other bedroom. This property is minutes away from the Winchester Historic downtown and a short drive to Shenandoah University. This is a well kept property and is waiting for you to make it yours! Schedule your showing online and allow time since the seller has two little dogs to take care off when you go show it. There are video cameras at the property.

3 Beds ⋅ 3 Baths

A must see property! This is a beautifull well kept colonial house with 3 bedrooms, 2 full bath and 1 half bath. The basement is unfinish but is ready to be build. As you enter the main level, you will see a nice welcoming livingroom, diningroom and beautiful granite countertops in the kitchen, with stainless steel appliances and high effitiency washer and dryer to the side. From the kitchen you can easily walkout to a huge concrete patio for a great family cookout and joyful huge backyard. The back yard is infenced with 6ft tall white vinyl privacy fence that makes it look very elegant and secured... In the upper level of the house, you will find the masterbedroom with a masterbath, and a second bath for the 2 other bedroom. This property is minutes away from the Winchester Historic downtown and a short drive to Shenandoah University. This is a well kept property and is waiting for you to make it yours! Schedule your showing online and allow time since the seller has two little dogs to take care off when you go show it. There are video cameras at the property.

421 Longview Ave, Winchester

Listing courtesy of Samson Properties. Contact:

$289,900

Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas. The updated kitchen features new cabinetry and stainless steel appliances, creating a clean, contemporary space perfect for everyday living and entertaining. Both bathrooms have also been thoughtfully updated, adding to the home’s fresh and modern appeal. Enjoy your morning coffee or unwind at the end of the day on the covered front porch. The partially fenced yard provides space to enjoy the outdoors, while the storage shed offers convenient additional space for tools, lawn equipment, and seasonal items. Convenient rear-entry parking provides easy access to the home, with additional street parking available in front. The unfinished basement provides valuable additional storage and utility space. With its attractive updates, functional floor plan, outdoor space, storage shed, and convenient parking, 621 Watson Avenue is a standout opportunity in Winchester! Whether you're searching for a comfortable place to call home or a great investment property, this beautifully refreshed duplex is ready for its next owner. Schedule your tour on ShowingTime today and see why 621 Watson Avenue stands out!

3 Beds ⋅ 2 Baths

Fresh, stylish, and move-in ready! Welcome to 621 Watson Avenue, a beautifully refreshed 3-bedroom, 1.5-bath duplex offering a wonderful blend of classic character and modern updates. Step inside to find freshly painted walls and beautiful hardwood floors that create a bright, inviting atmosphere throughout the main living areas. The updated kitchen features new cabinetry and stainless steel appliances, creating a clean, contemporary space perfect for everyday living and entertaining. Both bathrooms have also been thoughtfully updated, adding to the home’s fresh and modern appeal. Enjoy your morning coffee or unwind at the end of the day on the covered front porch. The partially fenced yard provides space to enjoy the outdoors, while the storage shed offers convenient additional space for tools, lawn equipment, and seasonal items. Convenient rear-entry parking provides easy access to the home, with additional street parking available in front. The unfinished basement provides valuable additional storage and utility space. With its attractive updates, functional floor plan, outdoor space, storage shed, and convenient parking, 621 Watson Avenue is a standout opportunity in Winchester! Whether you're searching for a comfortable place to call home or a great investment property, this beautifully refreshed duplex is ready for its next owner. Schedule your tour on ShowingTime today and see why 621 Watson Avenue stands out!

621 Watson Ave, Winchester

Listing courtesy of Samson Properties. Contact:

$325,000

Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or entertaining, and a private driveway for convenient off-street parking. Ideally located close to downtown Winchester, shopping, dining, and commuter routes. Move-in ready and waiting for you to make it your own!

4 Beds ⋅ 2 Baths

Welcome home! This beautifully maintained two-level home offers 4 bedrooms and 2 full bathrooms in the heart of Winchester. Warm and inviting, the home features a comfortable, functional layout with classic charm and thoughtful updates throughout. Pride of ownership is evident in every detail, both inside and out. Enjoy spacious living areas, a fully fenced yard perfect for relaxing or entertaining, and a private driveway for convenient off-street parking. Ideally located close to downtown Winchester, shopping, dining, and commuter routes. Move-in ready and waiting for you to make it your own!

805 S Kent St, Winchester

Listing courtesy of Weichert, REALTORS. Contact:

$359,000

Nestled on a quiet cul-de-sac surrounded by mature trees in the highly desirable Orchard Hills Subdivision with no HOA fees or restrictions, this traditional all-brick home features 3 bedrooms, 1.5 bathrooms, a 2-car driveway, and three beautifully finished levels of move-in-ready living space. From the tree-lined sidewalks and charming street lighting, you are welcomed onto a main level boasting gorgeous original hardwood floors, a convenient main-level half bath, a spacious formal dining room, and a warm living room anchored by a cozy wood-burning fireplace. The efficient kitchen offers a brand-new stove, plenty of storage and prep space, and a dedicated pantry for ultimate organization. The entire home has been freshly painted inside, with brand-new carpet installed across the stairs and bedrooms—including the large primary bedroom upstairs. Head downstairs to find a full, finished basement that provides additional living space, an abundance of extra storage, and a dedicated laundry area. Major mechanical updates offer complete peace of mind, including an all-brick exterior, a newer roof, newer HVAC, and newer windows throughout. Step outside to your private oasis—an extensive patio framed by beautiful mature trees that backs directly to the scenic Park Place Park, offering an extended backyard feel and peaceful views with no rear neighbors. Complete with a large storage shed to easily house all of your tools, lawn equipment, or outdoor gear. Conveniently located near shopping, dining, walking trails, and major commuter routes. Come see this home and schedule your private tour today!

3 Beds ⋅ 2 Baths

Nestled on a quiet cul-de-sac surrounded by mature trees in the highly desirable Orchard Hills Subdivision with no HOA fees or restrictions, this traditional all-brick home features 3 bedrooms, 1.5 bathrooms, a 2-car driveway, and three beautifully finished levels of move-in-ready living space. From the tree-lined sidewalks and charming street lighting, you are welcomed onto a main level boasting gorgeous original hardwood floors, a convenient main-level half bath, a spacious formal dining room, and a warm living room anchored by a cozy wood-burning fireplace. The efficient kitchen offers a brand-new stove, plenty of storage and prep space, and a dedicated pantry for ultimate organization. The entire home has been freshly painted inside, with brand-new carpet installed across the stairs and bedrooms—including the large primary bedroom upstairs. Head downstairs to find a full, finished basement that provides additional living space, an abundance of extra storage, and a dedicated laundry area. Major mechanical updates offer complete peace of mind, including an all-brick exterior, a newer roof, newer HVAC, and newer windows throughout. Step outside to your private oasis—an extensive patio framed by beautiful mature trees that backs directly to the scenic Park Place Park, offering an extended backyard feel and peaceful views with no rear neighbors. Complete with a large storage shed to easily house all of your tools, lawn equipment, or outdoor gear. Conveniently located near shopping, dining, walking trails, and major commuter routes. Come see this home and schedule your private tour today!

812 Appleseed Ct, Winchester

Listing courtesy of Realty FC. Contact:

$339,900

Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, functionality, and everyday convenience. The Floorplan is open and contemporary. The Great Room has Cathedral Ceilings and is very spacious. The grounds are taken care of by the community so life is easy. One level living w/ newer HVAC, a 4 year old roof, LVP flooring, updated bath, 2 bedrooms + 2 full bath. The 1 car garage is heated and cooled for year round comfort. There is space for a car and small workshop. You'll feel welcomed in this neighborly community where people walk, socialize and have planned activities at the well appointed Community Center. It is right around the corner from this home. Also, this home is located near the Abrams Creek Wetlands Preserve, perfect for walking + biking. Hospital + Down Town Winchester are 10 minutes away. Priced well and ready for you, come take a look today.

2 Beds ⋅ 2 Baths

Come see what makes Willow Lawn, a 55+ community, such a desirable place to call home! This inviting one owner Winchester home offers a comfortable blend of charm, functionality, and everyday convenience. The Floorplan is open and contemporary. The Great Room has Cathedral Ceilings and is very spacious. The grounds are taken care of by the community so life is easy. One level living w/ newer HVAC, a 4 year old roof, LVP flooring, updated bath, 2 bedrooms + 2 full bath. The 1 car garage is heated and cooled for year round comfort. There is space for a car and small workshop. You'll feel welcomed in this neighborly community where people walk, socialize and have planned activities at the well appointed Community Center. It is right around the corner from this home. Also, this home is located near the Abrams Creek Wetlands Preserve, perfect for walking + biking. Hospital + Down Town Winchester are 10 minutes away. Priced well and ready for you, come take a look today.

1847 Melvor Ln, Winchester

Listing courtesy of Century 21 Redwood Realty. Contact:

$409,000

Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully.

4 Beds ⋅ 1 Baths

Welcome to a Mid‑Century Modern Home Where Timeless Character Meets Modern Sophistication. This beautifully updated 3–4 bedroom mid‑century modern home, where timeless character meets modern sophistication in one of Winchester’s most convenient and walkable locations. The large covered front porch immediately sets the tone—an inviting space for morning coffee or relaxed evening conversation. Inside, natural light fills the home, highlighting refinished hardwood floors, fresh interior and exterior paint, and preserved architectural details including original wide wood baseboard trim and classic pocket doors. The well‑proportioned bedrooms offer comfortable retreats with the same warm character found throughout the home. Also added for efficient heating and cooling year‑round, a new ductless mini‑split system has been installed for your comfort. The renovated kitchen features new cabinetry, granite countertops, trending black stainless‑steel appliances, and a pantry with built‑in cabinetry, providing excellent storage and everyday functionality. Thoughtful upgrades and custom touches enhance each living space, creating an atmosphere that is both refined and inviting. Step outside to a covered back porch with new maintenance‑free decking, overlooking an open backyard ideal for relaxing, entertaining, gardening, or unwinding at the end of the day. Additional conveniences include off‑street parking and an oversized single‑car detached garage. The neighborhood continues to shine with recent street repaving and new sidewalks, enhancing curb appeal and walkability. Ideally located just a short stroll from Winchester’s vibrant downtown pedestrian mall, you’ll enjoy easy access to restaurants, coffee shops, boutiques, breweries, and community events. Mature trees, walkable streets, and proximity to commuter routes, parks, schools, and everyday amenities make this location truly exceptional. This is a rare opportunity to own a handsome, thoughtfully updated home that captures the best of Winchester living—where character, comfort, and location come together beautifully.

322 E Piccadilly, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$364,900

"Come On Down To Cidermill" Beautiful 3 bedroom, 2 1/2 bath duplex style townhome at end of street! All 3 bedrooms on upper level. Spacious family room, large eat in kitchen and back deck with stairs down to the yard. Large laundry room on basement level. One car garage and spacious driveway. Conveniently located in Winchester City. Home has just been remolded with the following: All new LVP flooring throughout, freshly painted on the inside, front door painted, garage door painted, shutters painted, handrail out front painted, deck remodeled, fresh mulch, bushes trimmed, new stainless-steel appliances and a new HVAC system! Hurry this one won't last long!

3 Beds ⋅ 3 Baths

"Come On Down To Cidermill" Beautiful 3 bedroom, 2 1/2 bath duplex style townhome at end of street! All 3 bedrooms on upper level. Spacious family room, large eat in kitchen and back deck with stairs down to the yard. Large laundry room on basement level. One car garage and spacious driveway. Conveniently located in Winchester City. Home has just been remolded with the following: All new LVP flooring throughout, freshly painted on the inside, front door painted, garage door painted, shutters painted, handrail out front painted, deck remodeled, fresh mulch, bushes trimmed, new stainless-steel appliances and a new HVAC system! Hurry this one won't last long!

1957 Cidermill Ln, Winchester

Listing courtesy of Samson Properties. Contact:

$699,000

Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

7 Beds ⋅ 5 Baths

Welcome to 2700 Loyalty Court—a beautifully maintained showcase home offering nearly 5,000 square feet of unmatched versatility in one of Winchester City’s most coveted locations. Commanding a prime corner lot on a peaceful cul-de-sac, this residence immediately captivates with its timeless stone-and-vinyl exterior, inviting covered front porch, and unmistakable curb appeal. Step inside to a soaring two-story foyer flowing into a light-filled interior boasting fresh paint, newer carpet, refined architectural details, and abundant natural light throughout. Designed for both grand scale entertaining and effortless everyday living, the main level features a dedicated office behind French doors, a formal dining room accented by elegant wainscoting, a den and a full bath. At the heart of the home, the sprawling family room makes a bold statement with architectural pillars and a floor-to-ceiling stone gas fireplace. It connects seamlessly to a chef-friendly kitchen complete with granite countertops, upgraded cabinetry, stainless steel appliances, a center island, pantry, built-in desk area, and a bright breakfast nook opening directly to the rear deck. A handy mudroom with laundry off the garage completes this level's intuitive floor plan. The impressive layout continues upstairs, offering abundant accommodations for family and guests across five generously sized bedrooms. The massive primary retreat serves as a true private sanctuary, complete with a dedicated sitting area, large walk-in closet, and a spa-like ensuite bath featuring a glass walk-in shower and a corner soaking tub. Two bedrooms are connected by a convenient Jack-and-Jill bath, alongside two more spacious bedrooms and another full bathroom. The real showstopper continues downstairs in the fully finished, walkout lower level—a massive multi-functional footprint that expands your living options exponentially. This lower level provides endless flexibility, featuring an expansive recreation room for hosting game days or movie nights, a full bath and two additional bedrooms perfect for guests, and multiple finished rooms ready to serve as a home gym, playroom, or hobby space—plus a storage area to keep it all organized. Offering extraordinary scale on a premier corner cul-de-sac lot, this move-in-ready home represents Winchester living at its finest and stands ready to welcome its next proud owners.

2700 Loyalty Ct, Winchester

Listing courtesy of Colony Realty. Contact:

$335,000

Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless appeal while providing modern living spaces that cater to today's lifestyle. With 1,507 square feet of thoughtfully designed space, this residence features three cozy bedrooms and one and a half bathrooms, making it an ideal retreat for anyone seeking a warm and inviting atmosphere. As you step inside, you'll be greeted by a spacious layout that encourages both relaxation and entertaining. The partially finished basement offers endless possibilities-whether you envision a cozy family room, a home office, or a play area, the choice is yours! The main living areas are bathed in natural light, creating a welcoming ambiance that feels like home. The exterior of the property is equally inviting, with a classic brick façade that stands the test of time. Enjoy the convenience of on-street parking, ensuring that you and your guests always have a place to park. The surrounding neighborhood is a tapestry of tree-lined streets and friendly faces, fostering a sense of community that is hard to find. Location is key, and this home does not disappoint. Situated in a vibrant area, you'll find an array of local amenities just a stone's throw away. Explore nearby parks for leisurely strolls or picnics, and take advantage of local shops and eateries that add character to the community. Whether you're grabbing a morning coffee or enjoying a weekend brunch, the neighborhood offers a delightful selection of options to satisfy your cravings. For those who appreciate the outdoors, the proximity to parks and recreational areas provides ample opportunities for hiking, biking, and enjoying nature. The community is well-connected, making it easy to access nearby attractions and essential services. This charming ranch-style home is more than just a property; it's a place where memories are made and cherished. With its inviting atmosphere, convenient location, and potential for personalization, this residence is ready to welcome you home. Don't miss the chance to make this delightful space your own!

3 Beds ⋅ 2 Baths

Nestled in a charming neighborhood, this delightful ranch-style home offers a perfect blend of comfort and convenience. Built in 1954, this brick beauty exudes timeless appeal while providing modern living spaces that cater to today's lifestyle. With 1,507 square feet of thoughtfully designed space, this residence features three cozy bedrooms and one and a half bathrooms, making it an ideal retreat for anyone seeking a warm and inviting atmosphere. As you step inside, you'll be greeted by a spacious layout that encourages both relaxation and entertaining. The partially finished basement offers endless possibilities-whether you envision a cozy family room, a home office, or a play area, the choice is yours! The main living areas are bathed in natural light, creating a welcoming ambiance that feels like home. The exterior of the property is equally inviting, with a classic brick façade that stands the test of time. Enjoy the convenience of on-street parking, ensuring that you and your guests always have a place to park. The surrounding neighborhood is a tapestry of tree-lined streets and friendly faces, fostering a sense of community that is hard to find. Location is key, and this home does not disappoint. Situated in a vibrant area, you'll find an array of local amenities just a stone's throw away. Explore nearby parks for leisurely strolls or picnics, and take advantage of local shops and eateries that add character to the community. Whether you're grabbing a morning coffee or enjoying a weekend brunch, the neighborhood offers a delightful selection of options to satisfy your cravings. For those who appreciate the outdoors, the proximity to parks and recreational areas provides ample opportunities for hiking, biking, and enjoying nature. The community is well-connected, making it easy to access nearby attractions and essential services. This charming ranch-style home is more than just a property; it's a place where memories are made and cherished. With its inviting atmosphere, convenient location, and potential for personalization, this residence is ready to welcome you home. Don't miss the chance to make this delightful space your own!

1048 Woodland Ave, Winchester

Listing courtesy of Re/Max Roots. Contact:

$419,000

Larger than it appears, this beautiful 3‑bedroom, 2‑bathroom home sits on a convenient street just minutes from historic downtown Winchester. The location offers effortless access to main commuter roads, making daily travel smooth and stress‑free. It’s also close to Shenandoah University, adding even more appeal for investors, students, faculty, or anyone who values proximity to campus and city amenities. Inside, the layout provides exceptional flexibility — the home can function as two completely separate rentals, giving it true income‑producing capabilities while maintaining all the original details you provided. A nice deck extends your living space outdoors, overlooking a large, flat, fully fenced backyard perfect for relaxing, entertaining, or tenant use. This is a great opportunity in a prime Winchester location. Come take a look and see the potential for yourself.

3 Beds ⋅ 2 Baths

Larger than it appears, this beautiful 3‑bedroom, 2‑bathroom home sits on a convenient street just minutes from historic downtown Winchester. The location offers effortless access to main commuter roads, making daily travel smooth and stress‑free. It’s also close to Shenandoah University, adding even more appeal for investors, students, faculty, or anyone who values proximity to campus and city amenities. Inside, the layout provides exceptional flexibility — the home can function as two completely separate rentals, giving it true income‑producing capabilities while maintaining all the original details you provided. A nice deck extends your living space outdoors, overlooking a large, flat, fully fenced backyard perfect for relaxing, entertaining, or tenant use. This is a great opportunity in a prime Winchester location. Come take a look and see the potential for yourself.

1412 S Loudoun St, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$299,900

This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full basement provides ample storage or potential for additional living space, enhancing the property's value. Set on a generous 0.34-acre lot, there's plenty of room for outdoor enjoyment or future enhancements. The vinyl siding ensures low maintenance, while the inviting architectural style adds character. Investors will appreciate the potential for significant returns as the renovations breathe new life into this home, making it an attractive option for renters or future buyers. With its warm ambiance and promising upgrades, this property is a sound investment in a thriving community. Don't miss the chance to be part of its exciting journey!

2 Beds ⋅ 2 Baths

This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full basement provides ample storage or potential for additional living space, enhancing the property's value. Set on a generous 0.34-acre lot, there's plenty of room for outdoor enjoyment or future enhancements. The vinyl siding ensures low maintenance, while the inviting architectural style adds character. Investors will appreciate the potential for significant returns as the renovations breathe new life into this home, making it an attractive option for renters or future buyers. With its warm ambiance and promising upgrades, this property is a sound investment in a thriving community. Don't miss the chance to be part of its exciting journey!

2519 Hockman Ave, Winchester

Listing courtesy of Link Realty Services LLC. Contact:

$250,000

Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to relax or entertain. Conveniently located near shopping, dining and everyday amenities, with quick access to I-81 from Winchester's east side—making it an excellent option for commuters. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance home in the city, this bungalow is worth a look. Schedule your showing today!

2 Beds ⋅ 1 Baths

Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to relax or entertain. Conveniently located near shopping, dining and everyday amenities, with quick access to I-81 from Winchester's east side—making it an excellent option for commuters. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance home in the city, this bungalow is worth a look. Schedule your showing today!

1125 Conway St, Winchester

Listing courtesy of NextHome Realty Select. Contact:

$750,000

Rare Historical Winchester Investment Opportunity – Three Properties in One Location An outstanding investment opportunity awaits in the heart of Winchester City. This unique portfolio comprises three properties positioned along the same street, offering exceptional potential for developers, investors, or those seeking a landmark project for multi-unit rentals or commercial development. Both existing multi-unit buildings have a total of 5 units. The properties benefit from an approved site plan and historical planning approval, providing a valuable foundation for future development, subject to the necessary consents and any relevant conditions. With the convenience of city-center living on the doorstep, the site is ideally placed close to Winchester’s historic attractions, independent shops, restaurants, cafés, transport links, and highly regarded schools. Opportunities of this scale and location are rarely available. Whether considered as a strategic investment, a redevelopment project, or a long-term development opportunity, this is a compelling chance to secure three properties together in the historic heart of Winchester. Key features: • Three properties located on one street • Prime central Winchester location • Approved site plan • Historical planning approval • Strong investment and development potential • Close to shops, restaurants, schools, transport links, and historic landmarks • Rare opportunity to acquire the properties as one portfolio 3 Physical property addresses are 224 Sharp Street, 225 E. Boscowan Street, and 11 S East Lane Interested parties should make their own inquiries with Winchester City Council and obtain independent legal, planning, and financial advice before proceeding.

224 Sharp St, Winchester

Listing courtesy of Real Broker LLC- Winchester. Contact:

$245,000

Roof replaced in 2020. Water heater: 2026. NEW PRICE! Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a convenient half bath. Upstairs offers two generously sized bedrooms with ample closet space and a full bath. Step outside to the Trex deck and manageable backyard, perfect for relaxing or entertaining. Off-street parking for two vehicles is a rare bonus in this downtown location. Whether you're a first-time buyer, downsizer, or investor, this home offers comfort, convenience, and an excellent location with easy access to I-81 and Northern Virginia. Enjoy everything Winchester has to offer, including the vibrant Old Town district, locally owned restaurants and boutiques, breweries, cultural attractions, and historic landmarks. Schedule your private showing today! All sizes are approximate.

2 Beds ⋅ 2 Baths

Roof replaced in 2020. Water heater: 2026. NEW PRICE! Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a convenient half bath. Upstairs offers two generously sized bedrooms with ample closet space and a full bath. Step outside to the Trex deck and manageable backyard, perfect for relaxing or entertaining. Off-street parking for two vehicles is a rare bonus in this downtown location. Whether you're a first-time buyer, downsizer, or investor, this home offers comfort, convenience, and an excellent location with easy access to I-81 and Northern Virginia. Enjoy everything Winchester has to offer, including the vibrant Old Town district, locally owned restaurants and boutiques, breweries, cultural attractions, and historic landmarks. Schedule your private showing today! All sizes are approximate.

103 E Germain St, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$364,900

NO HOA-City of Winchester on cul-de-sac with a spacious yard that feels like a private oasis.Charming and inviting townhome offering an unusual and versatile four-level floor plan with wonderful indoor and outdoor living spaces! The main level features a welcoming living room with a beautiful bay window, fireplace and built-in shelving, along with a dining room accented by crown molding and chair rail. A convenient closet provides additional storage for china and linens. The updated kitchen offers Corian countertops and includes a refrigerator, dishwasher, disposal, built in microwave and range. A half bath completes the main level. (a chairlift from the first level to the second level can remain with the property or removed) The second level offers three comfortable bedrooms and a full bath that has been updated. The first lower level expands the living space with a finished recreation room featuring built-ins, plus separate laundry area and half bath. Step outside to enjoy the beautifully landscaped rear yard—an unusually generous outdoor space for a townhome. The spacious deck is perfect for relaxing, entertaining or enjoying the surrounding greenery, with convenient access from the lower level recreation room. There is access from the front yard via steps on the side of the home leading to the deck providing both access to the lower level recreation room and deck. Additional steps from the deck lead down to the lush backyard. The lowest level is unfinished and provides a small workshop area, abundant storage and a walkout to the lush rear yard at ground level. An exceptional opportunity to enjoy the space and flexibility of a four level townhome complimented by a wonderfully private and expansive outdoor setting. Additional items of note: New roof 2025, new heat pump 2025, new hot water heater 2026, full bath remodeled 2024, new clothes dryer, 2024, new refrigerator 2020, Exterior painted 2017, windows replaced-2015 (most but not living room bay), kitchen remodeled,2015, wood walkway built on the side of the house, 2015 and additional insulation in attic, 2015

3 Beds ⋅ 3 Baths

NO HOA-City of Winchester on cul-de-sac with a spacious yard that feels like a private oasis.Charming and inviting townhome offering an unusual and versatile four-level floor plan with wonderful indoor and outdoor living spaces! The main level features a welcoming living room with a beautiful bay window, fireplace and built-in shelving, along with a dining room accented by crown molding and chair rail. A convenient closet provides additional storage for china and linens. The updated kitchen offers Corian countertops and includes a refrigerator, dishwasher, disposal, built in microwave and range. A half bath completes the main level. (a chairlift from the first level to the second level can remain with the property or removed) The second level offers three comfortable bedrooms and a full bath that has been updated. The first lower level expands the living space with a finished recreation room featuring built-ins, plus separate laundry area and half bath. Step outside to enjoy the beautifully landscaped rear yard—an unusually generous outdoor space for a townhome. The spacious deck is perfect for relaxing, entertaining or enjoying the surrounding greenery, with convenient access from the lower level recreation room. There is access from the front yard via steps on the side of the home leading to the deck providing both access to the lower level recreation room and deck. Additional steps from the deck lead down to the lush backyard. The lowest level is unfinished and provides a small workshop area, abundant storage and a walkout to the lush rear yard at ground level. An exceptional opportunity to enjoy the space and flexibility of a four level townhome complimented by a wonderfully private and expansive outdoor setting. Additional items of note: New roof 2025, new heat pump 2025, new hot water heater 2026, full bath remodeled 2024, new clothes dryer, 2024, new refrigerator 2020, Exterior painted 2017, windows replaced-2015 (most but not living room bay), kitchen remodeled,2015, wood walkway built on the side of the house, 2015 and additional insulation in attic, 2015

802 Appleseed Ct, Winchester

Listing courtesy of Colony Realty. Contact:

$396,190

660 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for October move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. Up to $7,500 total closing cost is tied to the use of DHI Mortgage. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

4 Beds ⋅ 4 Baths

660 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for October move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. Up to $7,500 total closing cost is tied to the use of DHI Mortgage. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

660 Arden Ct, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

$393,495

652 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for October move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. Up to $7,500 total closing cost is tied to the use of DHI Mortgage. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

4 Beds ⋅ 4 Baths

652 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for October move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances. The upper floor offers 3 bedrooms including a spacious owner's suite with a private bath and large walk-in closet and a convenient bedroom level laundry. Abrams Crossing at Meadow Branch features a fully walkable location and offers convenient access to I-81 and all major commute routes. It's close to shopping, restaurants, and Winchester Medical Center. Featuring America's Smart Home, D.R. Horton keeps you close to the people and places you value most. Simplify your life with a dream home that features hands-free communication, remote keyless entry, video doorbell, and so much more! It’s a home that adapts to your lifestyle. And with D.R. Horton's simple buying process and ten-year limited warranty, there's no reason to wait. Up to $7,500 total closing cost is tied to the use of DHI Mortgage. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

652 Arden Ct, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

$615,000

Welcome home to this beautifully updated brick-front residence in the City of Winchester, where a thoughtful floor plan, generous living spaces with 9' ceilings on the main and upper levels, and meaningful improvements come together across three finished levels. The main level is designed for connection and comfort, beginning with a two-story foyer that opens into an airy, open-concept layout. The kitchen flows seamlessly into the main living area, creating an ideal space for everyday living and entertaining, while offering defined rooms for flexibility. Just off the kitchen, the mudroom connects to the garage and provides ample storage and seating when entering and exiting the home. A dedicated office provides a quiet place to work, and the formal dining room—enhanced with beautiful moldings—offers an elegant setting for gatherings. A separate music room adds space to relax or unwind. Throughout the main level, new crown molding, freshly painted walls and ceilings, and bamboo flooring create a cohesive feel, while brushed nickel finishes add a modern touch. The fireplace with new gas logs serves as an inviting focal point for the living area. From the main level, step through one of the new sliding glass doors onto the newly built deck, with stairs leading directly to the yard. This outdoor space is ideal for morning coffee, summer dinners, or entertaining friends. Upstairs, new oak hardwood flooring enhances the main stairs, landing, hallway, and primary suite, including a large double-sided walk-in closet. The entire upper level has freshly painted walls and ceilings, while new crown molding extends from the two-story foyer into the hallway. The primary bathroom has been updated and features heated flooring with app control for added comfort. The additional upstairs bathroom has also been updated, and the other three upstairs bedrooms feature new carpeting, giving the entire level a fresh, cohesive feel. One of the most convenient features of the upper level is the dedicated laundry room—no more carrying baskets between floors. Finished with waterproof LVT flooring, cabinetry, a countertop, walk-in closet shelving, and included Consumer Reports top-rated high efficiency washer and dryer, it is both practical and well-appointed. The lower level expands the home even further with nearly 1,000 additional finished square feet. Fresh paint and new carpeting throughout give this level a clean, updated feel. This space includes a large recreation room with a separate entry, offering excellent flexibility for entertaining or everyday living. It also features a fifth bedroom (non-legal egress) and a full bathroom, and an additional washer and dryer hookup - making it ideal for guests, extended stays, or multi-use living arrangements. Behind the scenes, the home has been carefully maintained and upgraded for long-term comfort and efficiency. The roof, washer and dryer, and HVAC system are all approximately four years old. The HVAC system is a Carrier air handler paired with a Carrier air-conditioning unit featuring a variable-speed inverter compressor, providing exceptional efficiency and helping keep energy costs low. Additional improvements include upgraded R-52 attic insulation, Honeywell Home app controls, and a Tamko Titan architectural shingle roof rated for 50 years. The attached 2-car garage has also been enhanced with highly insulated Lewin-Yount doors and Aladdin Connect smartphone control. With approximately 2,700 square feet above grade plus nearly 1,000 finished square feet in the basement, this 5-bedroom, 3½-bath Winchester City home offers a rare combination of space, versatility, and move-in-ready convenience. From its open and functional floor plan to its hardwood and bamboo flooring, updated systems, flexible living spaces, and thoughtful upgrades throughout, this is a home designed for both everyday living and memorable gatherings. Come inside, take your time, and imagine making it yours. Welcome HOME!

5 Beds ⋅ 4 Baths

Welcome home to this beautifully updated brick-front residence in the City of Winchester, where a thoughtful floor plan, generous living spaces with 9' ceilings on the main and upper levels, and meaningful improvements come together across three finished levels. The main level is designed for connection and comfort, beginning with a two-story foyer that opens into an airy, open-concept layout. The kitchen flows seamlessly into the main living area, creating an ideal space for everyday living and entertaining, while offering defined rooms for flexibility. Just off the kitchen, the mudroom connects to the garage and provides ample storage and seating when entering and exiting the home. A dedicated office provides a quiet place to work, and the formal dining room—enhanced with beautiful moldings—offers an elegant setting for gatherings. A separate music room adds space to relax or unwind. Throughout the main level, new crown molding, freshly painted walls and ceilings, and bamboo flooring create a cohesive feel, while brushed nickel finishes add a modern touch. The fireplace with new gas logs serves as an inviting focal point for the living area. From the main level, step through one of the new sliding glass doors onto the newly built deck, with stairs leading directly to the yard. This outdoor space is ideal for morning coffee, summer dinners, or entertaining friends. Upstairs, new oak hardwood flooring enhances the main stairs, landing, hallway, and primary suite, including a large double-sided walk-in closet. The entire upper level has freshly painted walls and ceilings, while new crown molding extends from the two-story foyer into the hallway. The primary bathroom has been updated and features heated flooring with app control for added comfort. The additional upstairs bathroom has also been updated, and the other three upstairs bedrooms feature new carpeting, giving the entire level a fresh, cohesive feel. One of the most convenient features of the upper level is the dedicated laundry room—no more carrying baskets between floors. Finished with waterproof LVT flooring, cabinetry, a countertop, walk-in closet shelving, and included Consumer Reports top-rated high efficiency washer and dryer, it is both practical and well-appointed. The lower level expands the home even further with nearly 1,000 additional finished square feet. Fresh paint and new carpeting throughout give this level a clean, updated feel. This space includes a large recreation room with a separate entry, offering excellent flexibility for entertaining or everyday living. It also features a fifth bedroom (non-legal egress) and a full bathroom, and an additional washer and dryer hookup - making it ideal for guests, extended stays, or multi-use living arrangements. Behind the scenes, the home has been carefully maintained and upgraded for long-term comfort and efficiency. The roof, washer and dryer, and HVAC system are all approximately four years old. The HVAC system is a Carrier air handler paired with a Carrier air-conditioning unit featuring a variable-speed inverter compressor, providing exceptional efficiency and helping keep energy costs low. Additional improvements include upgraded R-52 attic insulation, Honeywell Home app controls, and a Tamko Titan architectural shingle roof rated for 50 years. The attached 2-car garage has also been enhanced with highly insulated Lewin-Yount doors and Aladdin Connect smartphone control. With approximately 2,700 square feet above grade plus nearly 1,000 finished square feet in the basement, this 5-bedroom, 3½-bath Winchester City home offers a rare combination of space, versatility, and move-in-ready convenience. From its open and functional floor plan to its hardwood and bamboo flooring, updated systems, flexible living spaces, and thoughtful upgrades throughout, this is a home designed for both everyday living and memorable gatherings. Come inside, take your time, and imagine making it yours. Welcome HOME!

922 Wayne Dr, Winchester

Listing courtesy of Samson Properties. Contact:

$419,000

PRICED BELOW RECENT APPRAISED VALUE. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level washer/dryer. The second level of the home offers a sitting area, primary bedroom with its own half bath and two addtional bedrooms with a shared bathroom. Accessed by the third bedroom, the attic offers a blank canvas and could be easily transformed into a secondary living area, home office, or a recreation and fitness room. Wide plank pine flooring remains throughout most of the home along with many traditional fiixtures. Recent improvements include a new gourmet kitchen with SS appliances, hvac, water heater, exterior clapboard cedar siding replaced where needed and new tile floors in the kitchen, main level bath and utility room. Step outside to the quaint backyard which offers an oasis for relaxation, play and gardening. The location of the home can't be beat. Just a few blocks to the pedestrian mall, one can experience a plethora of dining options, coffee shops, boutique stores, galleries and local social activities.

3 Beds ⋅ 3 Baths

PRICED BELOW RECENT APPRAISED VALUE. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen, additional full bath and main level washer/dryer. The second level of the home offers a sitting area, primary bedroom with its own half bath and two addtional bedrooms with a shared bathroom. Accessed by the third bedroom, the attic offers a blank canvas and could be easily transformed into a secondary living area, home office, or a recreation and fitness room. Wide plank pine flooring remains throughout most of the home along with many traditional fiixtures. Recent improvements include a new gourmet kitchen with SS appliances, hvac, water heater, exterior clapboard cedar siding replaced where needed and new tile floors in the kitchen, main level bath and utility room. Step outside to the quaint backyard which offers an oasis for relaxation, play and gardening. The location of the home can't be beat. Just a few blocks to the pedestrian mall, one can experience a plethora of dining options, coffee shops, boutique stores, galleries and local social activities.

422 S Loudoun St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

$400,000

Lofts at Creekside is one of the newest walkable communities in the city of Winchester with proximity to the upscale Creekside Station. Offering eateries, clothing stores, and professional services allows you to start or end your day at a plethora of local store fronts only steps from your home. Being only 2 years young allows the comfort of practically a new home in impeccable condition. Two car garage, front porch, and a recreation room greet you on the ground floor. Main level modern kitchen complemented by soft close cabinets and stunning countertops transitioning to the spacious living room with immense amount of natural light and back porch for morning coffee or evening happy hour. Condo association takes care of lawn maintenance and snow removal.

3 Beds ⋅ 3 Baths

Lofts at Creekside is one of the newest walkable communities in the city of Winchester with proximity to the upscale Creekside Station. Offering eateries, clothing stores, and professional services allows you to start or end your day at a plethora of local store fronts only steps from your home. Being only 2 years young allows the comfort of practically a new home in impeccable condition. Two car garage, front porch, and a recreation room greet you on the ground floor. Main level modern kitchen complemented by soft close cabinets and stunning countertops transitioning to the spacious living room with immense amount of natural light and back porch for morning coffee or evening happy hour. Condo association takes care of lawn maintenance and snow removal.

3135 Eton Pl, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$274,000

This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently painted and a new roof installed in 2025. This home would be great "Handyman's Delight" as the interior needs quite a bit of attention as the bath and kitchen are outdated. The 100 amp electric service was updated in 1993, water heater installed in 2012 and the oil furnace is a newer model. This house currently is winterized and electricity shut off. (There is no lighting in the basement.)

3 Beds ⋅ 2 Baths

This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently painted and a new roof installed in 2025. This home would be great "Handyman's Delight" as the interior needs quite a bit of attention as the bath and kitchen are outdated. The 100 amp electric service was updated in 1993, water heater installed in 2012 and the oil furnace is a newer model. This house currently is winterized and electricity shut off. (There is no lighting in the basement.)

519 Virginia Ave, Winchester

Listing courtesy of Colony Realty. Contact:

$340,000

SHORT SALE! Welcome to this adorable and beautifully refreshed Cape Cod, ideally located on a quiet street in Winchester City with no HOA! This move-in-ready home offers a comfortable and versatile floor plan, featuring a primary suite on the main level, plus two spacious bedrooms and a second full bathroom upstairs. Enjoy the peace of mind that comes with numerous recent updates and renovations completed in 2024, including architectural shingles, carport soffit, central heating and air conditioning with a dual-zone electric heat pump, crawl space sump pump and poly, and fresh paint throughout. Inside, you’ll find refinished real hardwood floors in the living areas and bedrooms, updated flooring in the kitchen and bathrooms, and numerous updated plumbing and light fixtures, vanities, outlets and switches. The Kitchen and primary bathroom feature a quartz countertop, an undermount sink with beautiful tiled shower with a glass door. This home offers a wonderful opportunity to move right in and enjoy.

3 Beds ⋅ 2 Baths

SHORT SALE! Welcome to this adorable and beautifully refreshed Cape Cod, ideally located on a quiet street in Winchester City with no HOA! This move-in-ready home offers a comfortable and versatile floor plan, featuring a primary suite on the main level, plus two spacious bedrooms and a second full bathroom upstairs. Enjoy the peace of mind that comes with numerous recent updates and renovations completed in 2024, including architectural shingles, carport soffit, central heating and air conditioning with a dual-zone electric heat pump, crawl space sump pump and poly, and fresh paint throughout. Inside, you’ll find refinished real hardwood floors in the living areas and bedrooms, updated flooring in the kitchen and bathrooms, and numerous updated plumbing and light fixtures, vanities, outlets and switches. The Kitchen and primary bathroom feature a quartz countertop, an undermount sink with beautiful tiled shower with a glass door. This home offers a wonderful opportunity to move right in and enjoy.

2919 S Pleasant Valley Rd, Winchester

Listing courtesy of Keller Williams Realty Dulles. Contact:

$490,000

Opportunity Knocks again. BACK ON THE MARKET. Major benefits/amenities, living within Winchester City Limits. New park being constructed a mile away. Location, Location, Location! NO HOA!!! Priced below assessed value! Hardwood floors on the main level. Formal living and dining room leads to the Family room with stone fireplace, breakfast nook and kitchen. Step out on to the deck to enjoy the views. Large fenced level backyard. Large Primary suite with sitting room and luxury bath. Good sized bedrooms, one with an attached bath. Lower level leads to a patio and backyard. Seller transferred. Opportunity to expand to 1 or 2 rental suites; seller had started the framing.... Near Shenandoah College, Publix new shopping center and major routes.

4 Beds ⋅ 4 Baths

Opportunity Knocks again. BACK ON THE MARKET. Major benefits/amenities, living within Winchester City Limits. New park being constructed a mile away. Location, Location, Location! NO HOA!!! Priced below assessed value! Hardwood floors on the main level. Formal living and dining room leads to the Family room with stone fireplace, breakfast nook and kitchen. Step out on to the deck to enjoy the views. Large fenced level backyard. Large Primary suite with sitting room and luxury bath. Good sized bedrooms, one with an attached bath. Lower level leads to a patio and backyard. Seller transferred. Opportunity to expand to 1 or 2 rental suites; seller had started the framing.... Near Shenandoah College, Publix new shopping center and major routes.

2643 Middle Rd, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$515,000

Fort Braddock Heights (Winchester City) - Detached Two-Level Home with Five (5) Bedrooms + Three (3) Full Bathrooms + One (1) Half Bathroom *Approx. 2,417 Finished Square Feet Across Two (2) Levels *Built 1992 *0.23 Acre Lot (Approx. 10,019 Square Feet) *One (1) Car Attached Front-Loading Garage + Paved Driveway *Second Garage Bay Converted to Oversized Main Level Laundry and Storage with Bonus Area Across the Front *Washer and Dryer Convey with the Property *Oversized Front Porch *Fully Fenced Rear Yard *Mature Landscaping *8' x 10' Outside Storage Shed *All Five (5) Bedrooms on the Upper Level *Two (2) Primary Suites *Primary Bathroom with Soaking Garden Tub + Separate Shower *Walk-In Closets *Vaulted Ceiling in Family Room Off the Kitchen *Wood-Burning Fireplace *Crown Moulding *Ceiling Fans *Additional Storage in Floored Attic Space *Updated Kitchen (2020) with Wood Cabinetry, Quartz Countertops and Stainless Steel Appliances *Luxury Vinyl Plank Flooring in Foyer and Kitchen *Architectural Shingle Roof (2009) *Tankless On-Demand Water Heater *Two (2) Zone Heating and Air Conditioning *No Homeowners Association *Cul-de-Sac Setting with No Through Street *Inside the City Limits of Winchester *Winchester City Public School Assignments *Close to Old Town Winchester *Minutes to Winchester Medical Center and the Shenandoah University Health Professions Campus *Convenient to Route 37 and Interstate 81 Commuter Routes.

5 Beds ⋅ 4 Baths

Fort Braddock Heights (Winchester City) - Detached Two-Level Home with Five (5) Bedrooms + Three (3) Full Bathrooms + One (1) Half Bathroom *Approx. 2,417 Finished Square Feet Across Two (2) Levels *Built 1992 *0.23 Acre Lot (Approx. 10,019 Square Feet) *One (1) Car Attached Front-Loading Garage + Paved Driveway *Second Garage Bay Converted to Oversized Main Level Laundry and Storage with Bonus Area Across the Front *Washer and Dryer Convey with the Property *Oversized Front Porch *Fully Fenced Rear Yard *Mature Landscaping *8' x 10' Outside Storage Shed *All Five (5) Bedrooms on the Upper Level *Two (2) Primary Suites *Primary Bathroom with Soaking Garden Tub + Separate Shower *Walk-In Closets *Vaulted Ceiling in Family Room Off the Kitchen *Wood-Burning Fireplace *Crown Moulding *Ceiling Fans *Additional Storage in Floored Attic Space *Updated Kitchen (2020) with Wood Cabinetry, Quartz Countertops and Stainless Steel Appliances *Luxury Vinyl Plank Flooring in Foyer and Kitchen *Architectural Shingle Roof (2009) *Tankless On-Demand Water Heater *Two (2) Zone Heating and Air Conditioning *No Homeowners Association *Cul-de-Sac Setting with No Through Street *Inside the City Limits of Winchester *Winchester City Public School Assignments *Close to Old Town Winchester *Minutes to Winchester Medical Center and the Shenandoah University Health Professions Campus *Convenient to Route 37 and Interstate 81 Commuter Routes.

1605 Fort Braddock Ct, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$450,000

$450,000 4 bedrooms, 2 Full baths, (Price is negotiable!) 2,493 square feet living space with a full basement 501 Fox drive is strategically located 1.5 miles from the Valley Health Hospital, 1.4 miles from James Wood High School and one mile from the highway at Route 37. Talk about great location!….This four bedroom family home is on a perfect corner lot for added space. Recently renovated with Fresh paint throughout, New laminate flooring, New blinds, Updated bathroom that includes a new sink/cabinet and a new toilet, The bedrooms include new carpeting and new ceiling fans. The new renovations also include a brand new dishwasher and dryer. To add on to the list this property add's new backyard fencing and new all weather 10 X 12 storage unit. Dream house for the first time buyer, Don’t miss this opportunity!

4 Beds ⋅ 2 Baths

$450,000 4 bedrooms, 2 Full baths, (Price is negotiable!) 2,493 square feet living space with a full basement 501 Fox drive is strategically located 1.5 miles from the Valley Health Hospital, 1.4 miles from James Wood High School and one mile from the highway at Route 37. Talk about great location!….This four bedroom family home is on a perfect corner lot for added space. Recently renovated with Fresh paint throughout, New laminate flooring, New blinds, Updated bathroom that includes a new sink/cabinet and a new toilet, The bedrooms include new carpeting and new ceiling fans. The new renovations also include a brand new dishwasher and dryer. To add on to the list this property add's new backyard fencing and new all weather 10 X 12 storage unit. Dream house for the first time buyer, Don’t miss this opportunity!

501 Fox Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$425,000

***Sellers offering $5k credit towards a mini-split -or- for closing cost assistance.*** This beautiful rancher sits on 0.38 acres with an expansive, level backyard that is fully fenced and shaded by gorgeous, mature trees. A large deck spans the back of the home and incorporates a charming stock-tank plunge pool with liner and filtration system, creating a fantastic space for relaxing and entertaining. Inside, the beautifully renovated kitchen is a standout, while the primary suite offers a walk-in closet and a stylishly remodeled en suite full bath with walk-in shower. The lower level adds even more living and entertaining space, with over half of the basement finished, a wet bar, and convenient walk-up access to the backyard. A carport and high-speed internet round out the home's practical features. Updated furnace, circuit breaker has a generator panel back up already wired just need a generator, heat lamp in the hallway bathroom, updated electrical and circuit breaker Electrical- $2,500, furnace $2,600

3 Beds ⋅ 2 Baths

***Sellers offering $5k credit towards a mini-split -or- for closing cost assistance.*** This beautiful rancher sits on 0.38 acres with an expansive, level backyard that is fully fenced and shaded by gorgeous, mature trees. A large deck spans the back of the home and incorporates a charming stock-tank plunge pool with liner and filtration system, creating a fantastic space for relaxing and entertaining. Inside, the beautifully renovated kitchen is a standout, while the primary suite offers a walk-in closet and a stylishly remodeled en suite full bath with walk-in shower. The lower level adds even more living and entertaining space, with over half of the basement finished, a wet bar, and convenient walk-up access to the backyard. A carport and high-speed internet round out the home's practical features. Updated furnace, circuit breaker has a generator panel back up already wired just need a generator, heat lamp in the hallway bathroom, updated electrical and circuit breaker Electrical- $2,500, furnace $2,600

413 Superior Ave, Winchester

Listing courtesy of Samson Properties. Contact: