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A view you'll never tire of coming home to! Tucked among mature trees and established landscaping in the desirable Shawneeland community, this charming 3-bedroom, 2-bath home offers a wonderful combination of privacy, natural beauty and comfortable one-level living. Here, the surrounding scenery becomes part of everyday life, changing with the seasons and providing a beautiful backdrop throughout the year. Step onto the deck with your morning coffee and take in the peaceful surroundings and picturesque views across the Winchester landscape. From the colors of fall to the beauty of a setting sun, there is always something new to appreciate. Inside, the home offers 1,248 finished square feet of living space with 3 bedrooms, 2 bathrooms, an open plan kitchen/dining room and a spacious family room which provdes access to the beautiful front deck. The home benefits from fresh paint throughout several areas of the main level adding to the home’s bright, welcoming feel. The practical ranch-style layout provides comfortable everyday living, while the attached one-car garage adds convenience and storage. The home has also benefited from several important updates in recent years, including the HVAC system, water heater, pressure tank, and updated washer and dryer, with the roof replaced in 2021. Beyond the property itself, enjoy the natural surroundings and established character of Shawneeland, with community amenities including fishing, playgrounds, picnic areas and a four-hole golf course. And with NO HOA, homeowners can enjoy an added level of freedom that's increasingly difficult to find. Just beyond the peaceful surroundings of home, the shops, restaurants, coffee houses and historic charm of Winchester are only a short drive away. Spend an afternoon strolling the Old Town Walking Mall, meet friends for dinner, or enjoy one of the many events that bring the area to life throughout the year. Commuters will appreciate easy access to major routes including Routes 50 and 7, as well as I-81, providing convenient connections throughout the Winchester area and beyond. Travel east toward Clarke and Loudoun Counties, including Berryville, Purcellville and Leesburg, or connect with major corridors serving the greater Northern Virginia region. At 151 Huron Trail, the view isn't something you simply notice when you arrive—it becomes part of the way you live. Come experience the privacy, changing seasons and spectacular sunsets for yourself. Enjoy your tour!

3 Beds ⋅ 2 Baths

A view you'll never tire of coming home to! Tucked among mature trees and established landscaping in the desirable Shawneeland community, this charming 3-bedroom, 2-bath home offers a wonderful combination of privacy, natural beauty and comfortable one-level living. Here, the surrounding scenery becomes part of everyday life, changing with the seasons and providing a beautiful backdrop throughout the year. Step onto the deck with your morning coffee and take in the peaceful surroundings and picturesque views across the Winchester landscape. From the colors of fall to the beauty of a setting sun, there is always something new to appreciate. Inside, the home offers 1,248 finished square feet of living space with 3 bedrooms, 2 bathrooms, an open plan kitchen/dining room and a spacious family room which provdes access to the beautiful front deck. The home benefits from fresh paint throughout several areas of the main level adding to the home’s bright, welcoming feel. The practical ranch-style layout provides comfortable everyday living, while the attached one-car garage adds convenience and storage. The home has also benefited from several important updates in recent years, including the HVAC system, water heater, pressure tank, and updated washer and dryer, with the roof replaced in 2021. Beyond the property itself, enjoy the natural surroundings and established character of Shawneeland, with community amenities including fishing, playgrounds, picnic areas and a four-hole golf course. And with NO HOA, homeowners can enjoy an added level of freedom that's increasingly difficult to find. Just beyond the peaceful surroundings of home, the shops, restaurants, coffee houses and historic charm of Winchester are only a short drive away. Spend an afternoon strolling the Old Town Walking Mall, meet friends for dinner, or enjoy one of the many events that bring the area to life throughout the year. Commuters will appreciate easy access to major routes including Routes 50 and 7, as well as I-81, providing convenient connections throughout the Winchester area and beyond. Travel east toward Clarke and Loudoun Counties, including Berryville, Purcellville and Leesburg, or connect with major corridors serving the greater Northern Virginia region. At 151 Huron Trail, the view isn't something you simply notice when you arrive—it becomes part of the way you live. Come experience the privacy, changing seasons and spectacular sunsets for yourself. Enjoy your tour!

151 Huron Trl, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$499,900

Big, beautiful, and ideally located, this spacious three-level Colonial offers 4 bedrooms, 3.5 baths, over 3,100 finished square feet, a 2-car garage, and a fully finished walkout basement. All situated on a generous half-acre lot. The main level features new LVP flooring, a spacious kitchen with center island, stainless steel appliances, multiple living and entertaining spaces, separate dining and a cozy fireplace. Upstairs, you'll find LVP flooring continued, generously sized bedrooms & closets, including an impressive sized primary suite with a walk-in closet and private bath. The fully finished walkout lower level has a full bath & adds even more living space with plenty of flexibility for a recreation room, home office, gym, guest area, or combination of uses. Outside, enjoy a large half-acre lot backing to mature trees, offering added privacy and plenty of room to enjoy the outdoors or watch your kiddos or fur-babies play. The location is hard to beat. Just minutes from shopping, dining, schools, Winchester Medical Center, and major commuter routes including Route 37, Route 522, and I-81. Best of all, enjoy the convenience of Winchester without city taxes or HOA fees! ** Seller is offering a 1 yr home warranty.**

4 Beds ⋅ 4 Baths

Big, beautiful, and ideally located, this spacious three-level Colonial offers 4 bedrooms, 3.5 baths, over 3,100 finished square feet, a 2-car garage, and a fully finished walkout basement. All situated on a generous half-acre lot. The main level features new LVP flooring, a spacious kitchen with center island, stainless steel appliances, multiple living and entertaining spaces, separate dining and a cozy fireplace. Upstairs, you'll find LVP flooring continued, generously sized bedrooms & closets, including an impressive sized primary suite with a walk-in closet and private bath. The fully finished walkout lower level has a full bath & adds even more living space with plenty of flexibility for a recreation room, home office, gym, guest area, or combination of uses. Outside, enjoy a large half-acre lot backing to mature trees, offering added privacy and plenty of room to enjoy the outdoors or watch your kiddos or fur-babies play. The location is hard to beat. Just minutes from shopping, dining, schools, Winchester Medical Center, and major commuter routes including Route 37, Route 522, and I-81. Best of all, enjoy the convenience of Winchester without city taxes or HOA fees! ** Seller is offering a 1 yr home warranty.**

409 Fortress Dr, Winchester

Listing courtesy of NextHome Realty Select. Contact:

$139,000

Welcome to relaxed and comfortable living in the desirable Regency Lakes community of Winchester, where this remarkably large and expansive manufactured home stands out exceptionally from neighboring properties by offering vastly superior square footage, an extended exterior profile, and a deep, generous footprint. Step inside to discover a truly massive, open-concept living area featuring stunning floor-to-ceiling stone accent fireplaces, soaring ceilings, and abundant space for oversized furniture and grand entertaining. A chef-styled kitchen boasts an immense array of rich wooden cabinetry, a brand-new gas cooktop, an expansive center prep island, and a seamless flow into the adjoining dining room. Recent updates further elevate the home, including new carpet (installed in 2023) and new wood floors in the guest room. Combining this unmatched scale with a functional floor plan designed to maximize everyday living, a wide covered front porch, and a private storage shed on a wonderful lot, the home provides quick access to local parks, schools, commuter arteries, and historic downtown Winchester for a lifestyle far bigger than the rest. This residency pays a ground rent of $953 that includes the following community amenities: swimming pool, whirlpool/spa/hot tub, clubhouse, fitness center, tennis courts, basketball and volleyball courts, a playground, picnic areas, horseshoes, fishing, waterfront sites, RV storage, on-site management, pet-friendly spaces, and regular community activities.

3 Beds ⋅ 3 Baths

Welcome to relaxed and comfortable living in the desirable Regency Lakes community of Winchester, where this remarkably large and expansive manufactured home stands out exceptionally from neighboring properties by offering vastly superior square footage, an extended exterior profile, and a deep, generous footprint. Step inside to discover a truly massive, open-concept living area featuring stunning floor-to-ceiling stone accent fireplaces, soaring ceilings, and abundant space for oversized furniture and grand entertaining. A chef-styled kitchen boasts an immense array of rich wooden cabinetry, a brand-new gas cooktop, an expansive center prep island, and a seamless flow into the adjoining dining room. Recent updates further elevate the home, including new carpet (installed in 2023) and new wood floors in the guest room. Combining this unmatched scale with a functional floor plan designed to maximize everyday living, a wide covered front porch, and a private storage shed on a wonderful lot, the home provides quick access to local parks, schools, commuter arteries, and historic downtown Winchester for a lifestyle far bigger than the rest. This residency pays a ground rent of $953 that includes the following community amenities: swimming pool, whirlpool/spa/hot tub, clubhouse, fitness center, tennis courts, basketball and volleyball courts, a playground, picnic areas, horseshoes, fishing, waterfront sites, RV storage, on-site management, pet-friendly spaces, and regular community activities.

123 Averrell Ave, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact:

$399,737

**WOW!!!** NEW PRICE + EXCEPTIONAL VALUE IN WINCHESTER! Move-In Ready • No HOA • Fantastic Location Across from Winchester Country Club! | Tucked away on a quiet cul-de-sac in the desirable Rolling Fields community, this beautifully updated Split Foyer offers a spacious .38-Acre Lot, peaceful tree-lined backyard & an EXTRA-DEEP OVERSIZED 2-CAR GARAGE! | Freshly Painted throughout with Brand-New Carpet, Gleaming Hardwood Floors & updated Luxury Vinyl Plank Flooring, this home is truly Move-In Ready | The bright & inviting Main Level features a spacious Living Room, Formal Dining Room & Eat-In Kitchen with Granite Countertops & Stainless Steel Appliances | 3 Main-Level Bedrooms & 2 Full Baths include a comfortable Primary Suite with Private Bath | The Finished Lower Level provides even more flexible living space with a Large Recreation Room, 4th Bedroom, Laundry Area & direct access to the Oversized Garage—offering exceptional room for Vehicles, Storage, Hobbies or a Workshop | Relax on the Covered Front Porch or head out back to the FRESHLY STAINED DECK WITH ALL-NEW DECK BOARDS & HANDRAILS overlooking the spacious, tree-lined backyard | NOTABLE RECENT IMPROVEMENTS INCLUDE: Freshly Stained Deck + New Deck Boards & Handrails (Sept. 2026), Fresh Interior Paint (2026), New Carpet (2026), Updated Vanity Lighting in Both Bathrooms (2026), Kitchen & Primary Bath Luxury Vinyl Plank Flooring (2025), Dishwasher (2025), Dryer (2022), Water Heater (2022), Refrigerator (2021), Roof (2017) & Garage Doors (2008) | Conveniently located just minutes from Shopping, Dining, Schools, Commuter Routes & Historic Downtown Winchester | WITH ITS NEW PRICE, NO HOA, .38-ACRE LOT, OVERSIZED GARAGE & EXTENSIVE UPDATES, THIS HOME OFFERS AN EXCEPTIONAL VALUE—DON'T MISS IT!

4 Beds ⋅ 2 Baths

**WOW!!!** NEW PRICE + EXCEPTIONAL VALUE IN WINCHESTER! Move-In Ready • No HOA • Fantastic Location Across from Winchester Country Club! | Tucked away on a quiet cul-de-sac in the desirable Rolling Fields community, this beautifully updated Split Foyer offers a spacious .38-Acre Lot, peaceful tree-lined backyard & an EXTRA-DEEP OVERSIZED 2-CAR GARAGE! | Freshly Painted throughout with Brand-New Carpet, Gleaming Hardwood Floors & updated Luxury Vinyl Plank Flooring, this home is truly Move-In Ready | The bright & inviting Main Level features a spacious Living Room, Formal Dining Room & Eat-In Kitchen with Granite Countertops & Stainless Steel Appliances | 3 Main-Level Bedrooms & 2 Full Baths include a comfortable Primary Suite with Private Bath | The Finished Lower Level provides even more flexible living space with a Large Recreation Room, 4th Bedroom, Laundry Area & direct access to the Oversized Garage—offering exceptional room for Vehicles, Storage, Hobbies or a Workshop | Relax on the Covered Front Porch or head out back to the FRESHLY STAINED DECK WITH ALL-NEW DECK BOARDS & HANDRAILS overlooking the spacious, tree-lined backyard | NOTABLE RECENT IMPROVEMENTS INCLUDE: Freshly Stained Deck + New Deck Boards & Handrails (Sept. 2026), Fresh Interior Paint (2026), New Carpet (2026), Updated Vanity Lighting in Both Bathrooms (2026), Kitchen & Primary Bath Luxury Vinyl Plank Flooring (2025), Dishwasher (2025), Dryer (2022), Water Heater (2022), Refrigerator (2021), Roof (2017) & Garage Doors (2008) | Conveniently located just minutes from Shopping, Dining, Schools, Commuter Routes & Historic Downtown Winchester | WITH ITS NEW PRICE, NO HOA, .38-ACRE LOT, OVERSIZED GARAGE & EXTENSIVE UPDATES, THIS HOME OFFERS AN EXCEPTIONAL VALUE—DON'T MISS IT!

187 Village Ct, Winchester

Listing courtesy of RE/MAX Distinctive Real Estate, Inc.. Contact:

$235,000

COME SEE THIS CUTE HOME AND MAKE IT YOURS. LOCATED IN SHAWNEE LAND, EASY DRIVE TO SHOPPING, SCHOOLS, HOSPITAL. SHAWNEE LAND HAS SEVERAL LAKES FOR EJOYMENT.HOME IS SOLD "AS IS", YOU CAN PUT YOUR TOUGHEST THOUGH OUT.

2 Beds ⋅ 1 Baths

COME SEE THIS CUTE HOME AND MAKE IT YOURS. LOCATED IN SHAWNEE LAND, EASY DRIVE TO SHOPPING, SCHOOLS, HOSPITAL. SHAWNEE LAND HAS SEVERAL LAKES FOR EJOYMENT.HOME IS SOLD "AS IS", YOU CAN PUT YOUR TOUGHEST THOUGH OUT.

302 Doe Trl Trl Sw, Winchester

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

$325,000

Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent condition, creating a warm and welcoming atmosphere that is ready for its next owner to enjoy. Outside, the spacious lot provides plenty of room to relax, entertain, garden, play, or simply enjoy having some extra breathing room without sacrificing the convenience of being in the city. One of the property's standout features is the abundance of parking available in front of the home, making it easy to accommodate multiple vehicles and guests. Whether you're hosting family and friends or simply appreciate having extra parking space, this home delivers. Location is another major highlight. Enjoy convenient access to Downtown Winchester, shopping, restaurants, schools, parks, everyday necessities, and major commuter routes, while still coming home to a property with plenty of outdoor space to call your own. With its generous lot, well-cared-for condition, ample parking, and convenient Winchester location, 2817 Papermill Road offers a combination that's increasingly hard to find. Come see what makes this home special—you may just find the space, location, and feeling of home you've been looking for.

3 Beds ⋅ 2 Baths

Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent condition, creating a warm and welcoming atmosphere that is ready for its next owner to enjoy. Outside, the spacious lot provides plenty of room to relax, entertain, garden, play, or simply enjoy having some extra breathing room without sacrificing the convenience of being in the city. One of the property's standout features is the abundance of parking available in front of the home, making it easy to accommodate multiple vehicles and guests. Whether you're hosting family and friends or simply appreciate having extra parking space, this home delivers. Location is another major highlight. Enjoy convenient access to Downtown Winchester, shopping, restaurants, schools, parks, everyday necessities, and major commuter routes, while still coming home to a property with plenty of outdoor space to call your own. With its generous lot, well-cared-for condition, ample parking, and convenient Winchester location, 2817 Papermill Road offers a combination that's increasingly hard to find. Come see what makes this home special—you may just find the space, location, and feeling of home you've been looking for.

2817 Papermill Rd, Winchester

Listing courtesy of Weichert, REALTORS. Contact:

$388,645

This Adams interior unit features 4 bedrooms, 3.5 baths, and a 1-car garage. With a total of 1,889 sq. ft, there is plenty of space to entertain and live comfortably. Enjoy 9' ceilings and luxury vinyl plank flooring on the main level. The kitchen features white cabinets with quartz countertops along with stainless steel appliances by Whirlpool. Relax on your 8'x14' rear deck and take advantage of the built-in Smart Home features. Washer and dryer plus whole house blinds included! Set for a November closing! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

4 Beds ⋅ 4 Baths

This Adams interior unit features 4 bedrooms, 3.5 baths, and a 1-car garage. With a total of 1,889 sq. ft, there is plenty of space to entertain and live comfortably. Enjoy 9' ceilings and luxury vinyl plank flooring on the main level. The kitchen features white cabinets with quartz countertops along with stainless steel appliances by Whirlpool. Relax on your 8'x14' rear deck and take advantage of the built-in Smart Home features. Washer and dryer plus whole house blinds included! Set for a November closing! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

141 Sioux Loop, Winchester

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

$300,000

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:

$394,990

New End Unit Under Construction for Fall Move In!! Main-level living at its best in Hiatt Pointe at Snowden Bridge—a gated 55+ active adult community. This low-maintenance villa features a primary bedroom and laundry on the entry level, a screened rear porch, and a one-car garage. Upstairs offers two spacious bedrooms with walk-in closets and a full bath, plus a finished storage area! Enjoy a stylish kitchen with quartz counters and stainless steel appliances. Resort-style amenities include pickleball and bocce courts, clubhouse, fitness and yoga studios, outdoor kitchen, pool and hot tub—plus snow removal, trash, and recycling included. Ask about builder incentives today!

3 Beds ⋅ 3 Baths

New End Unit Under Construction for Fall Move In!! Main-level living at its best in Hiatt Pointe at Snowden Bridge—a gated 55+ active adult community. This low-maintenance villa features a primary bedroom and laundry on the entry level, a screened rear porch, and a one-car garage. Upstairs offers two spacious bedrooms with walk-in closets and a full bath, plus a finished storage area! Enjoy a stylish kitchen with quartz counters and stainless steel appliances. Resort-style amenities include pickleball and bocce courts, clubhouse, fitness and yoga studios, outdoor kitchen, pool and hot tub—plus snow removal, trash, and recycling included. Ask about builder incentives today!

422 Granite Ridge Dr, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact:

$499,990

Under construction for fall move in! Discover relaxed, low‑maintenance living in this beautifully crafted twin/semi‑detached home, coming this summer to a sought‑after gated active‑adult community. Designed with today’s vibrant 55+ lifestyle in mind, the home offers effortless main‑level living with both a primary and secondary bedroom conveniently located on the first floor, along with a versatile den—ideal for a home office, creative space, or quiet retreat. The open‑concept design brings the kitchen and family room together, creating a warm, welcoming space perfect for hosting friends or simply enjoying everyday living. The gourmet kitchen features a generous island, stainless steel appliances, colada cabinetry, and elegant quartz countertops—blending style with functionality. Sun‑filled rooms and modern finishes throughout add to the home’s airy, inviting feel. Upstairs, a private third bedroom and full bath provide the perfect accommodations for visiting guests or additional flexible living space. Life at Hiatt Pointe is about more than just the home—it’s about the lifestyle. Residents enjoy resort‑style amenities including a sparkling outdoor pool, fitness center, and tennis courts, all within a secure, gated setting that encourages connection, wellness, and ease. Please note that interior photos are similar while home is under construction This is your opportunity to enjoy comfort, convenience, and community—without compromise. Ask about current builder incentives and make this exceptional home yours today.

3 Beds ⋅ 3 Baths

Under construction for fall move in! Discover relaxed, low‑maintenance living in this beautifully crafted twin/semi‑detached home, coming this summer to a sought‑after gated active‑adult community. Designed with today’s vibrant 55+ lifestyle in mind, the home offers effortless main‑level living with both a primary and secondary bedroom conveniently located on the first floor, along with a versatile den—ideal for a home office, creative space, or quiet retreat. The open‑concept design brings the kitchen and family room together, creating a warm, welcoming space perfect for hosting friends or simply enjoying everyday living. The gourmet kitchen features a generous island, stainless steel appliances, colada cabinetry, and elegant quartz countertops—blending style with functionality. Sun‑filled rooms and modern finishes throughout add to the home’s airy, inviting feel. Upstairs, a private third bedroom and full bath provide the perfect accommodations for visiting guests or additional flexible living space. Life at Hiatt Pointe is about more than just the home—it’s about the lifestyle. Residents enjoy resort‑style amenities including a sparkling outdoor pool, fitness center, and tennis courts, all within a secure, gated setting that encourages connection, wellness, and ease. Please note that interior photos are similar while home is under construction This is your opportunity to enjoy comfort, convenience, and community—without compromise. Ask about current builder incentives and make this exceptional home yours today.

114 Carnation Way, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact:

$335,000

***New Lower Price ***Just a short drive from vibrant Old Town Winchester, this charmingly sophisticated 3-bedroom, 2½-bath townhome blends affordability with modern comfort and thoughtful updates. Lovingly maintained and beautifully situated on a lot backing to mature trees, this home offers an inviting combination of style, functionality, and outdoor living. The main level features a large living room, an open kitchen and dining area that opens to the deck, and a 1/2 bath. Upstairs, you will find 3 bedrooms, 2 full baths, and the laundry room. Recent improvements enhance both the home’s functionality and outdoor living experience, including professionally installed landscape lighting, a new patio, Ring cameras at both the front and rear doors, and GFCI protection for the outdoor fan and TV. The garage has also been refreshed with recessed lighting and freshly painted walls. The lower level is framed, with electrical work completed under Frederick County permits, leaving the space ready for drywall and your personal design vision. Additional updates throughout the home include new light fixtures and ceiling fans, as well as a refreshed primary bathroom featuring a new countertop, backsplash, and sink. The open floor plan makes entertaining friends and family effortless. Step outside to the spacious deck overlooking the mature trees, or gather on the new patio, enhanced by custom lighting for relaxing evenings outdoors. Enjoy all that Winchester has to offer, including museums, Jim Barnett Park, Patsy Cline’s historic home, and the vibrant walking mall. Home to more than 50 boutique shops and retail businesses and over 40 restaurants, cafés, breweries, and bars, Old Town offers something for everyone. After dinner, catch a performance at the Bright Box Theater and make an evening of it.

3 Beds ⋅ 3 Baths

***New Lower Price ***Just a short drive from vibrant Old Town Winchester, this charmingly sophisticated 3-bedroom, 2½-bath townhome blends affordability with modern comfort and thoughtful updates. Lovingly maintained and beautifully situated on a lot backing to mature trees, this home offers an inviting combination of style, functionality, and outdoor living. The main level features a large living room, an open kitchen and dining area that opens to the deck, and a 1/2 bath. Upstairs, you will find 3 bedrooms, 2 full baths, and the laundry room. Recent improvements enhance both the home’s functionality and outdoor living experience, including professionally installed landscape lighting, a new patio, Ring cameras at both the front and rear doors, and GFCI protection for the outdoor fan and TV. The garage has also been refreshed with recessed lighting and freshly painted walls. The lower level is framed, with electrical work completed under Frederick County permits, leaving the space ready for drywall and your personal design vision. Additional updates throughout the home include new light fixtures and ceiling fans, as well as a refreshed primary bathroom featuring a new countertop, backsplash, and sink. The open floor plan makes entertaining friends and family effortless. Step outside to the spacious deck overlooking the mature trees, or gather on the new patio, enhanced by custom lighting for relaxing evenings outdoors. Enjoy all that Winchester has to offer, including museums, Jim Barnett Park, Patsy Cline’s historic home, and the vibrant walking mall. Home to more than 50 boutique shops and retail businesses and over 40 restaurants, cafés, breweries, and bars, Old Town offers something for everyone. After dinner, catch a performance at the Bright Box Theater and make an evening of it.

292 Sage Cir, Winchester

Listing courtesy of Hunt Country Sotheby's International Realty. Contact:

$368,000

Low maintenance living near Town, Restaurants, and Shops. This charming 2 bedroom, 2 bath home is in the 55+ community of Woodbrook Village. Enjoy walking the trails and the large comfortable Community Center for large events or cozy gatherings. Hardwood floors throughout the home and granite countertops in the kitchen with a large pantry in the laundry room. A screened in porch adds additional space opening to a small fenced in garden area for enjoying the outdoors. HOA includes lawncare, trash, water, sewer and snow removal.

2 Beds ⋅ 2 Baths

Low maintenance living near Town, Restaurants, and Shops. This charming 2 bedroom, 2 bath home is in the 55+ community of Woodbrook Village. Enjoy walking the trails and the large comfortable Community Center for large events or cozy gatherings. Hardwood floors throughout the home and granite countertops in the kitchen with a large pantry in the laundry room. A screened in porch adds additional space opening to a small fenced in garden area for enjoying the outdoors. HOA includes lawncare, trash, water, sewer and snow removal.

102 Buckwood Ln, Winchester

Listing courtesy of CENTURY 21 New Millennium. Contact:

$275,000

Tucked away in the woods of Shawneeland, this 3-bedroom, 1-bath home sits on nearly half an acre and is just 20 minutes from Winchester City. With some TLC and a little vision, this property has the potential to become a charming retreat and a place to truly make your own. Set on a partially wooded lot, the property offers peaceful surroundings and inviting outdoor spaces, including a front deck and a private rear deck. A storage shed is located in the backyard for convenience. The open-concept main level features a kitchen with upgraded quartz countertops and stainless steel appliances, a living room with a stone wood-burning fireplace, and a dining area. Also on the main level is a spacious bedroom, a full bathroom, and a dedicated laundry area. Upstairs, a spiral staircase leads to two additional bedrooms, creating a cozy and flexible layout. Enjoy the privacy and natural beauty of a wooded setting while remaining conveniently close to Winchester. Approximate updates include new roof in 2023,new water heater in 2022, new water softener in 2022, septic pumped in 2026, new pressure tank in 2024, new microwave in 2026.

3 Beds ⋅ 1 Baths

Tucked away in the woods of Shawneeland, this 3-bedroom, 1-bath home sits on nearly half an acre and is just 20 minutes from Winchester City. With some TLC and a little vision, this property has the potential to become a charming retreat and a place to truly make your own. Set on a partially wooded lot, the property offers peaceful surroundings and inviting outdoor spaces, including a front deck and a private rear deck. A storage shed is located in the backyard for convenience. The open-concept main level features a kitchen with upgraded quartz countertops and stainless steel appliances, a living room with a stone wood-burning fireplace, and a dining area. Also on the main level is a spacious bedroom, a full bathroom, and a dedicated laundry area. Upstairs, a spiral staircase leads to two additional bedrooms, creating a cozy and flexible layout. Enjoy the privacy and natural beauty of a wooded setting while remaining conveniently close to Winchester. Approximate updates include new roof in 2023,new water heater in 2022, new water softener in 2022, septic pumped in 2026, new pressure tank in 2024, new microwave in 2026.

132 Dogwood Trl, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$384,990

***OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* The most affordable townhomes in Winchester City! END OF ROW Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free deck overlooking mature trees. Attached 1-car garage provides additional storage and convenience. New luxury townhomes in Winchester are selling quickly; schedule your tour today before this opportunity is gone!*Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing

3 Beds ⋅ 4 Baths

***OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* The most affordable townhomes in Winchester City! END OF ROW Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free deck overlooking mature trees. Attached 1-car garage provides additional storage and convenience. New luxury townhomes in Winchester are selling quickly; schedule your tour today before this opportunity is gone!*Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing

Homesite 126 Monteith Drive, Winchester

Listing courtesy of DRB Group Realty, LLC. Contact:

$325,000

Charming 3-bedroom, 2-full-bath Cape Cod situated on .88 acres in a convenient location just minutes from Winchester City. This inviting home offers the flexibility of a main-level bedroom and full bath, along with a cozy wood-burning fireplace that adds warmth and character. Enjoy relaxing or entertaining on the welcoming front porch or side porch, with plenty of outdoor space to enjoy. A standout feature of this property is the large detached barn/garage offering 7 bays—an incredible amount of space for vehicles, equipment, storage, a workshop, hobbies, or recreational toys. With nearly an acre, a versatile floor plan, and exceptional outbuilding space, this property offers a unique combination of convenience, character, and functionality while being extremely close to Winchester.

3 Beds ⋅ 2 Baths

Charming 3-bedroom, 2-full-bath Cape Cod situated on .88 acres in a convenient location just minutes from Winchester City. This inviting home offers the flexibility of a main-level bedroom and full bath, along with a cozy wood-burning fireplace that adds warmth and character. Enjoy relaxing or entertaining on the welcoming front porch or side porch, with plenty of outdoor space to enjoy. A standout feature of this property is the large detached barn/garage offering 7 bays—an incredible amount of space for vehicles, equipment, storage, a workshop, hobbies, or recreational toys. With nearly an acre, a versatile floor plan, and exceptional outbuilding space, this property offers a unique combination of convenience, character, and functionality while being extremely close to Winchester.

144 Apple Valley Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

$370,000

With special financing options available, Discover the promise of your future home. This stunning Colonial-style residence all most completed. Move in your new home in just 30 days or less. This property offers a perfect blend of modern design and classic comfort. With three spacious bedrooms and two and a half bathrooms, this home is designed for both relaxation and entertaining. The interior boasts luxurious vinyl plank flooring and cozy carpet, creating a warm atmosphere throughout. An unfinished walkout basement provides endless possibilities for customization, whether you envision a home gym, a cozy den, or additional storage. Enjoy the convenience of upper-floor laundry and a driveway for easy parking. Nestled on a generous 0.27-acre level lot with possible option for expansion, this property invites you to create your own outdoor oasis. Imagine summer barbecues or quiet evenings on your future patio. With its thoughtful design, this home is waiting for your personal touch. Embrace the opportunity to make this house your dream home!

3 Beds ⋅ 3 Baths

With special financing options available, Discover the promise of your future home. This stunning Colonial-style residence all most completed. Move in your new home in just 30 days or less. This property offers a perfect blend of modern design and classic comfort. With three spacious bedrooms and two and a half bathrooms, this home is designed for both relaxation and entertaining. The interior boasts luxurious vinyl plank flooring and cozy carpet, creating a warm atmosphere throughout. An unfinished walkout basement provides endless possibilities for customization, whether you envision a home gym, a cozy den, or additional storage. Enjoy the convenience of upper-floor laundry and a driveway for easy parking. Nestled on a generous 0.27-acre level lot with possible option for expansion, this property invites you to create your own outdoor oasis. Imagine summer barbecues or quiet evenings on your future patio. With its thoughtful design, this home is waiting for your personal touch. Embrace the opportunity to make this house your dream home!

904 Panther Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

$365,000

With special financing options available, Discover the promise of your future home. This stunning Colonial-style residence all most completed. Move in your new home in just 30 days or less. This property offers a perfect blend of modern design and classic comfort. With three spacious bedrooms and two and a half bathrooms, this home is designed for both relaxation and entertaining. The interior boasts luxurious vinyl plank flooring and cozy carpet, creating a warm atmosphere throughout. An unfinished walkout basement provides endless possibilities for customization, whether you envision a home gym, a cozy den, or additional storage. Enjoy the convenience of upper-floor laundry and a driveway for easy parking. Nestled on a generous 0.27-acre level lot with possible option for expansion, this property invites you to create your own outdoor oasis. Imagine summer barbecues or quiet evenings on your future patio. With its thoughtful design, this home is waiting for your personal touch. Embrace the opportunity to make this house your dream home!

3 Beds ⋅ 3 Baths

With special financing options available, Discover the promise of your future home. This stunning Colonial-style residence all most completed. Move in your new home in just 30 days or less. This property offers a perfect blend of modern design and classic comfort. With three spacious bedrooms and two and a half bathrooms, this home is designed for both relaxation and entertaining. The interior boasts luxurious vinyl plank flooring and cozy carpet, creating a warm atmosphere throughout. An unfinished walkout basement provides endless possibilities for customization, whether you envision a home gym, a cozy den, or additional storage. Enjoy the convenience of upper-floor laundry and a driveway for easy parking. Nestled on a generous 0.27-acre level lot with possible option for expansion, this property invites you to create your own outdoor oasis. Imagine summer barbecues or quiet evenings on your future patio. With its thoughtful design, this home is waiting for your personal touch. Embrace the opportunity to make this house your dream home!

902 Panther Dr, Winchester

Listing courtesy of Coldwell Banker Premier. 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:

$292,500

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:

$479,900

This lovingly maintained two-owner Colonial has been thoughtfully cared for and improved since 1994, offering the character of an established home with many of the updates today's buyers are looking for. Homes in this sought-after neighborhood rarely come to market, making this a special opportunity in one of the area's most convenient commuter locations. Inside, you'll find a comfortable blend of hardwood, tile, and carpet flooring, built-in shelving, fresh paint in many areas, and charming details including chair rail and crown molding in select rooms. The living area features an antique stained-glass mantle that has been beautifully refinished and incorporated above the gas fireplace, creating a distinctive focal point. Upstairs, four large bedrooms provide plenty of comfortable living space, including a spacious primary bedroom with its own private bathroom. A finished and conditioned third-floor loft adds a huge, flexible bonus space ready to meet your needs; perfect for a 5th bedroom, playroom, office, game room, or additional living area. Storage abounds throughout this versatile space, offering possibilities to suit a variety of lifestyles. The kitchen is designed for both everyday living and entertaining, with an oversized island offering abundant storage, a butcher block top, and an eat-up bar area. Granite countertops are complemented by a white subway tile backsplash and a dramatic floor-to-ceiling accent wall. Recent improvements include a new water softener, a 2018 water heater, and a new washer and dryer installed in 2026. The HVAC systems are approximately two and three years old and have been recently serviced. The roof is less than five years old, while newer HardieBoard siding and windows provide additional peace of mind. Step outside to the large covered rear porch, finished with beadboard and a ceiling fan, overlooking the spacious fenced backyard. Mature trees and established landscaping create a private setting that is ideal for relaxing, entertaining, or enjoying outdoor time. The paved driveway adds convenience, while the no-HOA neighborhood provides added flexibility. Perfectly positioned close to town, schools, and everyday amenities while offering quick access to Route 7 for commuters, this home combines a well-established neighborhood setting with an exceptionally convenient location. A home with genuine character, meaningful improvements, and a level of care that is evident throughout.

5 Beds ⋅ 3 Baths

This lovingly maintained two-owner Colonial has been thoughtfully cared for and improved since 1994, offering the character of an established home with many of the updates today's buyers are looking for. Homes in this sought-after neighborhood rarely come to market, making this a special opportunity in one of the area's most convenient commuter locations. Inside, you'll find a comfortable blend of hardwood, tile, and carpet flooring, built-in shelving, fresh paint in many areas, and charming details including chair rail and crown molding in select rooms. The living area features an antique stained-glass mantle that has been beautifully refinished and incorporated above the gas fireplace, creating a distinctive focal point. Upstairs, four large bedrooms provide plenty of comfortable living space, including a spacious primary bedroom with its own private bathroom. A finished and conditioned third-floor loft adds a huge, flexible bonus space ready to meet your needs; perfect for a 5th bedroom, playroom, office, game room, or additional living area. Storage abounds throughout this versatile space, offering possibilities to suit a variety of lifestyles. The kitchen is designed for both everyday living and entertaining, with an oversized island offering abundant storage, a butcher block top, and an eat-up bar area. Granite countertops are complemented by a white subway tile backsplash and a dramatic floor-to-ceiling accent wall. Recent improvements include a new water softener, a 2018 water heater, and a new washer and dryer installed in 2026. The HVAC systems are approximately two and three years old and have been recently serviced. The roof is less than five years old, while newer HardieBoard siding and windows provide additional peace of mind. Step outside to the large covered rear porch, finished with beadboard and a ceiling fan, overlooking the spacious fenced backyard. Mature trees and established landscaping create a private setting that is ideal for relaxing, entertaining, or enjoying outdoor time. The paved driveway adds convenience, while the no-HOA neighborhood provides added flexibility. Perfectly positioned close to town, schools, and everyday amenities while offering quick access to Route 7 for commuters, this home combines a well-established neighborhood setting with an exceptionally convenient location. A home with genuine character, meaningful improvements, and a level of care that is evident throughout.

109 Julee Dr, Winchester

Listing courtesy of Realty ONE Group Old Towne. 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:

$375,000

You are going to love this spacious, one-level ranch located on a half-acre lot in a great location! Here are some of the key features and recent updates: - Huge 20x26 family room with Red Oak hardwood floors, a brick fireplace, and newly replaced French doors that open onto a large L-shaped front deck. - Bedrooms & Baths: New paint and new flooring throughout bedrooms and bathrooms master bath features a new vanity and new ceramic tile flooring, which is also featured in the hallway bath. master bedroom has full bath -Laundry: 8x8 laundry room complete with washer, dryer, cabinets, and counter space. -Kitchen and living room has Bruce flooring All new painting through out house - Upgrades: New ceiling fans in all rooms. The water pump, septic tank, and attic air handler for the AC unit have all been replaced. Both decks have been recently remodeled and resealed. - Garaging & Parking: you are going to love the Oversized 20x28 garage with front and back entry doors, plus a second attached 12×20 garage with entry door from the main garage! Large driveway with a 10+ car capacity and turnaround area. - Outdoor Space: Fenced backyard with a 10x12 back deck and beautiful pastoral views in both the front and back. Large L-shaped deck on front of house This home offers peaceful country living while remaining convenient to local grocery stores, restaurants, gas stations, schools, and major commuter routes this ranch offers the space & amenities you been dreaming of....... LOOK NO FURTHER!

4 Beds ⋅ 2 Baths

You are going to love this spacious, one-level ranch located on a half-acre lot in a great location! Here are some of the key features and recent updates: - Huge 20x26 family room with Red Oak hardwood floors, a brick fireplace, and newly replaced French doors that open onto a large L-shaped front deck. - Bedrooms & Baths: New paint and new flooring throughout bedrooms and bathrooms master bath features a new vanity and new ceramic tile flooring, which is also featured in the hallway bath. master bedroom has full bath -Laundry: 8x8 laundry room complete with washer, dryer, cabinets, and counter space. -Kitchen and living room has Bruce flooring All new painting through out house - Upgrades: New ceiling fans in all rooms. The water pump, septic tank, and attic air handler for the AC unit have all been replaced. Both decks have been recently remodeled and resealed. - Garaging & Parking: you are going to love the Oversized 20x28 garage with front and back entry doors, plus a second attached 12×20 garage with entry door from the main garage! Large driveway with a 10+ car capacity and turnaround area. - Outdoor Space: Fenced backyard with a 10x12 back deck and beautiful pastoral views in both the front and back. Large L-shaped deck on front of house This home offers peaceful country living while remaining convenient to local grocery stores, restaurants, gas stations, schools, and major commuter routes this ranch offers the space & amenities you been dreaming of....... LOOK NO FURTHER!

178 Payne Rd, Winchester

Listing courtesy of Century 21 Redwood Realty. 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:

$375,000

265 McDonald Rd is a 1-story Winchester home built in 1974 with a lower level and connected outdoor spaces. The kitchen includes cabinet storage, a preparation counter, and an adjoining area for dining. The main living room provides space for seating, with an additional finished room on the lower level. The primary bedroom includes a walk-in closet with shelving for organization and an adjoining bathroom with a shower and vanity. A rear deck connects to the home through sliding doors, extending the usable space outdoors. A dedicated laundry area includes cabinetry and a folding counter. The layout combines everyday living with practical storage.

3 Beds ⋅ 2 Baths

265 McDonald Rd is a 1-story Winchester home built in 1974 with a lower level and connected outdoor spaces. The kitchen includes cabinet storage, a preparation counter, and an adjoining area for dining. The main living room provides space for seating, with an additional finished room on the lower level. The primary bedroom includes a walk-in closet with shelving for organization and an adjoining bathroom with a shower and vanity. A rear deck connects to the home through sliding doors, extending the usable space outdoors. A dedicated laundry area includes cabinetry and a folding counter. The layout combines everyday living with practical storage.

265 Mcdonald Rd, Winchester

Listing courtesy of Open Door Brokerage, LLC. 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:

$450,000

No HOA in the heart of Winchester! NEW Roof Oct. 2026. This charming brick rancher features three bedrooms, three full baths, tall ceilings, fresh paint, hardwood floors, and a fireplace on the main level. The layout includes a versatile sunroom with a private entrance and a kitchen equipped with stainless steel appliances. The basement expands your living space with a kitchen, large storage room, and another fireplace! It offers the opportunity for additional rental income with its own separate entrance. Walk outside to the spacious, fully fenced backyard with a storage shed. Enjoy ample parking with an oversized attached garage. Don’t miss the opportunity to own this home in an excellent location, just steps from Winchester Country Club and minutes to shopping, dining, and commuter routes. This home provides timeless construction and incredible potential. *Seller is also offering a one-year Home Warranty with the sale of the property!

3 Beds ⋅ 3 Baths

No HOA in the heart of Winchester! NEW Roof Oct. 2026. This charming brick rancher features three bedrooms, three full baths, tall ceilings, fresh paint, hardwood floors, and a fireplace on the main level. The layout includes a versatile sunroom with a private entrance and a kitchen equipped with stainless steel appliances. The basement expands your living space with a kitchen, large storage room, and another fireplace! It offers the opportunity for additional rental income with its own separate entrance. Walk outside to the spacious, fully fenced backyard with a storage shed. Enjoy ample parking with an oversized attached garage. Don’t miss the opportunity to own this home in an excellent location, just steps from Winchester Country Club and minutes to shopping, dining, and commuter routes. This home provides timeless construction and incredible potential. *Seller is also offering a one-year Home Warranty with the sale of the property!

131 Country Club Cir, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$317,265

Seller Credit of $3000! Use it for a buydown to lower your payment!! See Flyer in docs NEW PHOTOS! Landscaping done! Professional cleaning done! New Flooring in bedrooms! Welcome to this charming three-bedroom, two-bathroom raised ranch nestled on a quiet, tree-lined street in one of the area’s most close-knit neighborhoods. Full of character and potential, this home boasts a classic floor plan just waiting for your cosmetic updates and personal design vision. A brand new roof and pressure tank! The main level features a bright living area filled with natural light, a dedicated dining space, and original hardwood flooring. Three comfortably sized bedrooms complete the upper level, including a primary bedroom with its own private en-suite bath. The full basement offers so much room to expand with a laundry area, a finished area for a possible sleeping room, ample heavy shelving units for crafting, storage or a workshop, and a walkout with sliding doors. Beyond the front door lies a vibrant, amenity-rich community known for its warm atmosphere. Neighborhood residents enjoy access to a spring-fed/man-made lake featuring a sandy beach area, swimming, fishing, and a boat ramp (gas motors are not permitted). Cherokee Beach is open to residents without a beach pass, additional smaller ponds and scenic streams located throughout the community, two community playgrounds, wooded nature walks and trails, pavilion spaces, open sports areas, and picnic spots, and covered/lighted mailbox stations and covered school bus stops.

3 Beds ⋅ 2 Baths

Seller Credit of $3000! Use it for a buydown to lower your payment!! See Flyer in docs NEW PHOTOS! Landscaping done! Professional cleaning done! New Flooring in bedrooms! Welcome to this charming three-bedroom, two-bathroom raised ranch nestled on a quiet, tree-lined street in one of the area’s most close-knit neighborhoods. Full of character and potential, this home boasts a classic floor plan just waiting for your cosmetic updates and personal design vision. A brand new roof and pressure tank! The main level features a bright living area filled with natural light, a dedicated dining space, and original hardwood flooring. Three comfortably sized bedrooms complete the upper level, including a primary bedroom with its own private en-suite bath. The full basement offers so much room to expand with a laundry area, a finished area for a possible sleeping room, ample heavy shelving units for crafting, storage or a workshop, and a walkout with sliding doors. Beyond the front door lies a vibrant, amenity-rich community known for its warm atmosphere. Neighborhood residents enjoy access to a spring-fed/man-made lake featuring a sandy beach area, swimming, fishing, and a boat ramp (gas motors are not permitted). Cherokee Beach is open to residents without a beach pass, additional smaller ponds and scenic streams located throughout the community, two community playgrounds, wooded nature walks and trails, pavilion spaces, open sports areas, and picnic spots, and covered/lighted mailbox stations and covered school bus stops.

148 Doe Trl, Winchester

Listing courtesy of Keller Williams Realty Advantage. Contact:

$289,900

Spacious three-level townhome in a desirable Winchester community, conveniently located near Sunnyside and Old Town Winchester! Offering generously sized bedrooms, three and a half baths, and flexible living space across three levels, this home has room for everyone. The main level features a comfortable family room, dining area, kitchen, and convenient powder room, with access to the spacious rear deck overlooking mature trees and HOA owned property. The private wooded setting creates a peaceful outdoor oasis, perfect for relaxing, grilling, or entertaining. Upstairs, you'll find two spacious bedrooms, each with its own full bath, providing excellent privacy and comfort. The finished basement adds even more versatility with a large recreation room, additional bonus/bedroom space, and a full bathroom. Whether used for guests, a home office, hobbies, or recreation, the lower level offers valuable additional living space. Enjoy the best of both convenience and tranquility, with a private, tree-lined setting while being just minutes from Sunnyside, Old Town Winchester, shopping, dining, parks, and commuter routes. A wonderful opportunity to enjoy spacious townhome living in a great location with flexible space and a private backyard setting.

3 Beds ⋅ 4 Baths

Spacious three-level townhome in a desirable Winchester community, conveniently located near Sunnyside and Old Town Winchester! Offering generously sized bedrooms, three and a half baths, and flexible living space across three levels, this home has room for everyone. The main level features a comfortable family room, dining area, kitchen, and convenient powder room, with access to the spacious rear deck overlooking mature trees and HOA owned property. The private wooded setting creates a peaceful outdoor oasis, perfect for relaxing, grilling, or entertaining. Upstairs, you'll find two spacious bedrooms, each with its own full bath, providing excellent privacy and comfort. The finished basement adds even more versatility with a large recreation room, additional bonus/bedroom space, and a full bathroom. Whether used for guests, a home office, hobbies, or recreation, the lower level offers valuable additional living space. Enjoy the best of both convenience and tranquility, with a private, tree-lined setting while being just minutes from Sunnyside, Old Town Winchester, shopping, dining, parks, and commuter routes. A wonderful opportunity to enjoy spacious townhome living in a great location with flexible space and a private backyard setting.

114 Tudor Dr, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact: