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Situated on a desirable cul-de-sac homesite backing to community open space, this thoughtfully designed home offers the perfect blend of comfort and functionality. The main level features a spacious owner's suite, formal dining room, laundry room, powder room, and an open-concept kitchen overlooking the living and dining areas. The kitchen includes quartz countertops, an island with seating, pantry, and breakfast nook. Upstairs, you'll find four additional bedrooms, including a private en-suite and a shared full bath. Designer-selected finishes, luxury vinyl plank flooring, whole-house blinds, smart home features, stainless steel appliances, refrigerator, washer, and dryer are all included. Move - in ready! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

5 Beds ⋅ 5 Baths

Situated on a desirable cul-de-sac homesite backing to community open space, this thoughtfully designed home offers the perfect blend of comfort and functionality. The main level features a spacious owner's suite, formal dining room, laundry room, powder room, and an open-concept kitchen overlooking the living and dining areas. The kitchen includes quartz countertops, an island with seating, pantry, and breakfast nook. Upstairs, you'll find four additional bedrooms, including a private en-suite and a shared full bath. Designer-selected finishes, luxury vinyl plank flooring, whole-house blinds, smart home features, stainless steel appliances, refrigerator, washer, and dryer are all included. Move - in ready! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

112 Wappinger Ter, Winchester

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

$625,000

Welcome to this beautiful single-family home in the sought-after Ravenwing neighborhood of Winchester, Virginia. The sellers are open to offers that include credits toward financing or flooring. Key systems have been updated, featuring a new water heater installed in 2022 and a brand-new roof completed in 2024. Conveniently located near local shopping, downtown Winchester, Costco, I-81, Route 50, and Route 7, this spacious two-story property offers over 3,500 square feet of comfortable living space tailored for modern living. The main level features a large kitchen complete with an island and a generous pantry, seamlessly connecting to a formal dining room, an open living room enhanced by custom built-in shelves, a versatile flex room, and a convenient half bath. Upstairs, the expansive primary bedroom serves as a private retreat with two walk-in closets and a dedicated en suite bathroom. Three additional bedrooms, a second full bathroom, and a conveniently located laundry room round out the upper floor. The finished basement adds over 800 square feet of versatile living space, complete with a third full bath and direct access to the outdoors. Outside, the quarter-acre lot features a fenced yard area and a back deck ideal for morning coffee or casual gatherings. Don't miss this opportunity to live in one of the most sought-after neighborhoods in Winchester!

4 Beds ⋅ 4 Baths

Welcome to this beautiful single-family home in the sought-after Ravenwing neighborhood of Winchester, Virginia. The sellers are open to offers that include credits toward financing or flooring. Key systems have been updated, featuring a new water heater installed in 2022 and a brand-new roof completed in 2024. Conveniently located near local shopping, downtown Winchester, Costco, I-81, Route 50, and Route 7, this spacious two-story property offers over 3,500 square feet of comfortable living space tailored for modern living. The main level features a large kitchen complete with an island and a generous pantry, seamlessly connecting to a formal dining room, an open living room enhanced by custom built-in shelves, a versatile flex room, and a convenient half bath. Upstairs, the expansive primary bedroom serves as a private retreat with two walk-in closets and a dedicated en suite bathroom. Three additional bedrooms, a second full bathroom, and a conveniently located laundry room round out the upper floor. The finished basement adds over 800 square feet of versatile living space, complete with a third full bath and direct access to the outdoors. Outside, the quarter-acre lot features a fenced yard area and a back deck ideal for morning coffee or casual gatherings. Don't miss this opportunity to live in one of the most sought-after neighborhoods in Winchester!

132 Darby Dr, Winchester

Listing courtesy of Dream Real Estate. Contact:

$579,990

Rare cul-de-sac home! The Hayden offers 6 bedrooms, 4 bathrooms, and over 3,100 square feet of beautifully designed living space. The open-concept main level features a flex room, a bedroom with full bath, and a spacious kitchen that flows seamlessly into the dining and living areas. Upstairs, enjoy a luxurious owner's suite, three additional bedrooms, a loft, and convenient laundry room. The finished walkout basement adds a recreation room, bedroom, and full bath, providing even more room to live and entertain. This home includes designer-selected finishes, quartz countertops, luxury vinyl plank flooring, a whole-house blinds package, laundry appliances, French door refrigerator, and backs to a peaceful setting in desirable Retreat at Winding Creek. Ready for delivery! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

6 Beds ⋅ 4 Baths

Rare cul-de-sac home! The Hayden offers 6 bedrooms, 4 bathrooms, and over 3,100 square feet of beautifully designed living space. The open-concept main level features a flex room, a bedroom with full bath, and a spacious kitchen that flows seamlessly into the dining and living areas. Upstairs, enjoy a luxurious owner's suite, three additional bedrooms, a loft, and convenient laundry room. The finished walkout basement adds a recreation room, bedroom, and full bath, providing even more room to live and entertain. This home includes designer-selected finishes, quartz countertops, luxury vinyl plank flooring, a whole-house blinds package, laundry appliances, French door refrigerator, and backs to a peaceful setting in desirable Retreat at Winding Creek. Ready for delivery! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

143 Wappinger Ter, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. 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 December 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 December 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

Ready for Move In End Unit!! 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

Ready for Move In End Unit!! 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:

$599,900

Nestled in the charming community of Stonebrook Farms, this delightful ranch-style home offers a perfect blend of comfort and functionality. Built in 1977, this well-maintained residence boasts 2,260 square feet of inviting living space, ideal for creating lasting memories. Step inside to discover a warm and welcoming interior featuring beautiful hardwood floors and an abundance of natural light. The traditional floor plan includes a spacious family room that flows seamlessly into the eat-in kitchen, making it perfect for gatherings and everyday living. The kitchen is adorned with upgraded countertops and newer stainless steel appliances, and a great breakfast bar perfect for quick meals. The home features three generously sized bedrooms, including a primary suite with a walk-in closet and an newly renovated bathroom equipped with a walk-in shower. Enjoy the comfort of a wood-burning fireplace in the family room, perfect for cozy evenings. The main floor laundry adds convenience to your daily routine. Outside, the property sits on a spacious one-acre lot, offering plenty of room for outdoor activities and gardening. The attached two-car garage and ample driveway parking ensure that you and your guests will always have a place to park. Stonebrook Farms is not just about the home; it's about the lifestyle. This friendly neighborhood is known for its strong sense of community, with nearby Rose Hill Park perfect for weekend picnics and leisurely strolls. Stonebrook Club (membership required) offers top-notch services including Tennis, Pickleball, Racquetball, Fitness and Pool just down the street, this option ensures that residents enjoy a high quality of life. With easy access to local amenities, shopping, and dining, everything you need is just a short drive away. This home in Stonebrook Farms is more than just a property; it's a place where you can truly feel at home. Experience the warmth and comfort of this inviting residence, and make it your own today!

3 Beds ⋅ 2 Baths

Nestled in the charming community of Stonebrook Farms, this delightful ranch-style home offers a perfect blend of comfort and functionality. Built in 1977, this well-maintained residence boasts 2,260 square feet of inviting living space, ideal for creating lasting memories. Step inside to discover a warm and welcoming interior featuring beautiful hardwood floors and an abundance of natural light. The traditional floor plan includes a spacious family room that flows seamlessly into the eat-in kitchen, making it perfect for gatherings and everyday living. The kitchen is adorned with upgraded countertops and newer stainless steel appliances, and a great breakfast bar perfect for quick meals. The home features three generously sized bedrooms, including a primary suite with a walk-in closet and an newly renovated bathroom equipped with a walk-in shower. Enjoy the comfort of a wood-burning fireplace in the family room, perfect for cozy evenings. The main floor laundry adds convenience to your daily routine. Outside, the property sits on a spacious one-acre lot, offering plenty of room for outdoor activities and gardening. The attached two-car garage and ample driveway parking ensure that you and your guests will always have a place to park. Stonebrook Farms is not just about the home; it's about the lifestyle. This friendly neighborhood is known for its strong sense of community, with nearby Rose Hill Park perfect for weekend picnics and leisurely strolls. Stonebrook Club (membership required) offers top-notch services including Tennis, Pickleball, Racquetball, Fitness and Pool just down the street, this option ensures that residents enjoy a high quality of life. With easy access to local amenities, shopping, and dining, everything you need is just a short drive away. This home in Stonebrook Farms is more than just a property; it's a place where you can truly feel at home. Experience the warmth and comfort of this inviting residence, and make it your own today!

220 Greenfield Ave, Winchester

Listing courtesy of Colony Realty. 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:

$525,000

Welcome to this like-new Winchester home, built in 2023 and offering the opportunity to enjoy modern construction without the wait! Set in a peaceful country setting yet just under five miles straight into Old Town Winchester, this home offers the perfect balance of quiet surroundings and easy access to the charming shops, restaurants, and small-town atmosphere of downtown. Designed for comfort and ease, all three bedrooms and two full baths are conveniently located on the main level. Stylish finishes and a bright, inviting layout create a move-in-ready feel throughout. The modern kitchen features a spacious center island with seating and opens to the main living area, where a cozy gas fireplace adds warmth and charm. Convenient main-level laundry makes everyday living even easier. The unfinished lower level offers incredible potential to create the space that works best for you. With a bathroom rough-in already in place, there is plenty of room for a future recreation area, guest suite, home office, gym, or additional living space. Outside, enjoy the deck overlooking the surrounding setting, along with a two-car garage for parking and additional storage. With its 2023 construction, convenient one-level living, and close proximity to Old Town Winchester, this home offers a wonderful opportunity to own a property that still feels practically new!

3 Beds ⋅ 2 Baths

Welcome to this like-new Winchester home, built in 2023 and offering the opportunity to enjoy modern construction without the wait! Set in a peaceful country setting yet just under five miles straight into Old Town Winchester, this home offers the perfect balance of quiet surroundings and easy access to the charming shops, restaurants, and small-town atmosphere of downtown. Designed for comfort and ease, all three bedrooms and two full baths are conveniently located on the main level. Stylish finishes and a bright, inviting layout create a move-in-ready feel throughout. The modern kitchen features a spacious center island with seating and opens to the main living area, where a cozy gas fireplace adds warmth and charm. Convenient main-level laundry makes everyday living even easier. The unfinished lower level offers incredible potential to create the space that works best for you. With a bathroom rough-in already in place, there is plenty of room for a future recreation area, guest suite, home office, gym, or additional living space. Outside, enjoy the deck overlooking the surrounding setting, along with a two-car garage for parking and additional storage. With its 2023 construction, convenient one-level living, and close proximity to Old Town Winchester, this home offers a wonderful opportunity to own a property that still feels practically new!

322 Lehigh Dr, Winchester

Listing courtesy of Property Collective. Contact:

$715,000

New price improvement! Below pre-listing appraisal! 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

New price improvement! Below pre-listing appraisal! 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:

$550,000

Get ready for this elegant and a beautiful Colonial home in the sought-after Freedom Manor community. Built in 2021, this residence boasts a spacious 2,904 sq. ft. layout, perfect for modern living. Freshly painted. Step inside to find an inviting open floor plan that seamlessly connects the gourmet kitchen to the family room, creating an ideal space for gatherings and everyday comfort. The kitchen is a chef's dream, featuring stainless steel appliances, a generous island, and a pantry. Enjoy the convenience of a walk-in shower in the primary bath, along with ample storage in the walk-in closet. The home also includes a cozy electric fireplace, perfect for those chilly evenings. With four well-appointed bedrooms and 2.5 bathrooms, there's plenty of room for everyone. The upper floor laundry adds to the ease of daily living, laundry machines convey with the house. The finished basement offers a versatile space perfect for entertaining, movie nights, game nights, a home gym, home office, or recreation room. The basement also offers the option to add an additional bathroom, with plumbing already roughed in and ready for finishing. Outside, the 0.19-acre lot offers a lovely front yard and a spacious rear fenced yard with a custom vinyl fence, ideal for outdoor activities or simply relaxing in the sun. Parking is a breeze with an attached two-car garage, generous sized driveway and additional on-street options. This home combines modern structure with a warm, inviting atmosphere, making it the perfect place to create lasting memories. Don't miss the opportunity to make this beautiful property your own!

4 Beds ⋅ 3 Baths

Get ready for this elegant and a beautiful Colonial home in the sought-after Freedom Manor community. Built in 2021, this residence boasts a spacious 2,904 sq. ft. layout, perfect for modern living. Freshly painted. Step inside to find an inviting open floor plan that seamlessly connects the gourmet kitchen to the family room, creating an ideal space for gatherings and everyday comfort. The kitchen is a chef's dream, featuring stainless steel appliances, a generous island, and a pantry. Enjoy the convenience of a walk-in shower in the primary bath, along with ample storage in the walk-in closet. The home also includes a cozy electric fireplace, perfect for those chilly evenings. With four well-appointed bedrooms and 2.5 bathrooms, there's plenty of room for everyone. The upper floor laundry adds to the ease of daily living, laundry machines convey with the house. The finished basement offers a versatile space perfect for entertaining, movie nights, game nights, a home gym, home office, or recreation room. The basement also offers the option to add an additional bathroom, with plumbing already roughed in and ready for finishing. Outside, the 0.19-acre lot offers a lovely front yard and a spacious rear fenced yard with a custom vinyl fence, ideal for outdoor activities or simply relaxing in the sun. Parking is a breeze with an attached two-car garage, generous sized driveway and additional on-street options. This home combines modern structure with a warm, inviting atmosphere, making it the perfect place to create lasting memories. Don't miss the opportunity to make this beautiful property your own!

111 Alliance Ct, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$364,900

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:

$259,900

SELLER OFFERING UP TO $7,000 TOWARD BUYER'S CLOSING COSTS WITH AN ACCEPTABLE OFFER! Buyer may use this credit toward allowable closing costs, prepaid expenses, or an interest rate buydown to help reduce monthly mortgage payments. Subject to lender approval and loan program guidelines. Located in the wooded community of Shawneeland, approximately 20 minutes from Winchester City, this 3-bedroom, 1-bath home sits on nearly half an acre, offering the potential to become a charming retreat and a place to truly make your own. Recent updates include a roof replaced in 2023, water heater and water softener installed in 2022, pressure tank replaced in 2024, and septic system pumped in 2026. A new microwave was also added in 2026. The main level features an open-concept layout with a kitchen offering quartz countertops and stainless steel appliances, a dining area, and a living room with a stone wood-burning fireplace. A bedroom, full bathroom, and dedicated laundry area are also located on the main level. Upstairs, a spiral staircase leads to two additional bedrooms. Outside, the partially wooded lot includes a front deck, rear deck, and backyard storage shed. The setting offers a measure of privacy while remaining within driving distance of Winchester and its shopping, dining, and everyday conveniences. With its wooded location, existing features, and several key system updates, this property offers potential for buyers seeking an opportunity to renovate and personalize a home to their own preferences.

3 Beds ⋅ 1 Baths

SELLER OFFERING UP TO $7,000 TOWARD BUYER'S CLOSING COSTS WITH AN ACCEPTABLE OFFER! Buyer may use this credit toward allowable closing costs, prepaid expenses, or an interest rate buydown to help reduce monthly mortgage payments. Subject to lender approval and loan program guidelines. Located in the wooded community of Shawneeland, approximately 20 minutes from Winchester City, this 3-bedroom, 1-bath home sits on nearly half an acre, offering the potential to become a charming retreat and a place to truly make your own. Recent updates include a roof replaced in 2023, water heater and water softener installed in 2022, pressure tank replaced in 2024, and septic system pumped in 2026. A new microwave was also added in 2026. The main level features an open-concept layout with a kitchen offering quartz countertops and stainless steel appliances, a dining area, and a living room with a stone wood-burning fireplace. A bedroom, full bathroom, and dedicated laundry area are also located on the main level. Upstairs, a spiral staircase leads to two additional bedrooms. Outside, the partially wooded lot includes a front deck, rear deck, and backyard storage shed. The setting offers a measure of privacy while remaining within driving distance of Winchester and its shopping, dining, and everyday conveniences. With its wooded location, existing features, and several key system updates, this property offers potential for buyers seeking an opportunity to renovate and personalize a home to their own preferences.

132 Dogwood Trl, Winchester

Listing courtesy of RE/MAX Roots. Contact:

$4,990,000

Rutherford Crossing is a two-tenant NNN retail strip center at 105-109 Market Street in Winchester, VA, anchored by corporate Starbucks (S&P: BBB+) with 10% rent step-ups every five years, alongside V Nails & Spas on a lease running through 2035. The offering delivers approximately $330,000 in stabilized NOI with true triple net structure and minimal landlord responsibilities, making it a clean, passive addition to any retail investment portfolio. The property sits within Rutherford Crossing, an approximately 600,000 SF power center along the growing I-81 corridor, surrounded by national credit anchors and steady daily traffic that drive consistent consumer draw. Winchester continues to see strong population and retail growth, giving this asset the location fundamentals and co-tenancy strength that long-term investors look for.

105 Market St, Winchester

Listing courtesy of CapStar Properties. 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:

$11,900

Lot 112 .40 acre Lot. Certification letter - 3 Bdrm Perc This Lot has the Views !! Come Build your part or full time Dream Home & Enjoy the Picture Perfect Mountain views! Located in Shawneeland with No HOA, enjoy the amenities, Large Recreational Park Area with fishing ponds connected by running streams, Playground, Picnic Pavillion(s), Basketball hoops, Tuscarora Trails, Cherokee Lake w/beach & fishing area, Swan Lake for fishing, Another Park Area w/ playground on Maple Trail. Hard top roads. Common grounds & Road maintenance & plowed in Winter. As you drive up Tomahawk Trail take in the endless views & homes. Shawneeland is a Sanitary District Fee is included in Real Estate Tax Bill. Live Rural with a short distance to Shopping, Hospital and Town. Seller is Motivated. Also For Sale adjoining Lots 113 & 114 VAFV2044996 - VAFV2045000

112 Tomahawk Trl, Winchester

Listing courtesy of MarketPlace REALTY. 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:

$270,000

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:

$3,500,000

Be sure to see the video and 3D tour to fully explore this property! Award-Winning Virginia Winery + Luxury Vineyard Estate + Income-Producing Luxury Short Term Rental + Development Lots! br> **Briede Family Vineyards** presents an exceptional opportunity to acquire one of Virginia's distinguished boutique vineyard estates. Offering far more than beautiful real estate, it provides the new owners the opportunity to continue a well-established legacy within the Commonwealth's thriving wine industry. Combining an award-winning vineyard and winery brand with an elegant country residence currently operating as a licensed short-term rental, this remarkable property is ideally suited for those seeking both a lifestyle investment and an established business. The property's total acreage also includes three additional building lots (with approved Well and Septic), providing exceptional opportunities for future residential development, guest accommodations, or investment, subject to applicable approvals. For years, Briede Family Vineyards has earned recognition for producing award-winning wines while cultivating a reputation for offering intimate, highly personalized guest experiences. Unlike larger commercial wineries, the vineyard has become known for its thoughtfully curated tastings, signature Champagne experiences, and imported French cheese pairings, creating a destination that guests return to year after year. The recognized brand, loyal clientele, and respected presence within Virginia's wine community provide an invaluable foundation for future ownership. The beautifully appointed tasting room and adjoining great room provide an inviting setting for tastings, private gatherings, and special events. Guests can also enjoy the charming covered pavilion overlooking the vineyard, offering an ideal outdoor venue for relaxing, live entertainment, special events, and taking in the surrounding views. Complementing the vineyard experience, the beautifully maintained residence offers guests the opportunity to experience life among the vines. Surrounded by sweeping vineyard vistas and tranquil countryside, the home serves equally well as a private estate residence, luxury guest accommodations, or an expanded hospitality venue, offering exceptional flexibility for a variety of ownership goals. The property encompasses established vineyards, meticulously maintained grounds, and the infrastructure necessary to continue current operations while providing opportunities for future growth. This is a true turnkey opportunity, allowing a new owner to step into an established vineyard operation with recognized branding and a well-developed hospitality experience, while providing an exceptional foundation for future growth and continued success. Whether expanding wine production, enhancing agritourism, hosting private events, or preserving the vineyard's boutique character, the possibilities are exceptional. Conveniently located in Frederick County, Virginia, with easy access to Northern Virginia, Washington, D.C., and the Shenandoah Valley, Briede Family Vineyards represents a rare opportunity to acquire a recognized vineyard destination where years of dedicated ownership, reputation, and hospitality come together in one remarkable offering.

Winchester

Listing courtesy of Keller Williams Realty. Contact:

$535,000

Welcome home to 100 Winns Circle, perfectly situated on a generous 0.4-acre corner lot in Pioneer Heights. Located less than 5 minutes from Route 7 east of Winchester, this beautifully updated property offers the rare combination of neighborhood living without close neighbors or crowded structures. Step inside to find a freshly painted interior bathed in natural light, thanks to oversized Andersen windows and new LED lighting throughout. The main level features gleaming hardwood floors in the formal dining room and a massive living room centered around a magnificent floor-to-ceiling stone wood-burning fireplace. From here, premium patio swing doors open to a large rear deck—ideal for entertaining or relaxing. The kitchen is a chef's delight, outfitted with pristine oak cabinets, Corian countertops, brand-new LVP flooring, and new appliances, including a side-by-side refrigerator and slim-profile microwave. Upstairs, the layout is designed for modern living. The spacious primary suite acts as a private wing, cleverly partitioned away from the other bedrooms to include a dedicated home office space and a large bath with a two-person Jacuzzi tub. Practical upgrades abound, ensuring total peace of mind: a new second-floor gas furnace and A/C (warranty conveys), a new 50-gallon gas water heater, a new radon fan system, and upgraded blown-in attic insulation. The oversized two-car garage features a newly epoxied floor, built-in shelving, an extra refrigerator, and a convenient door to the rear deck. Below, an expansive walkout basement with double doors, a concrete patio, and a workshop area stands ready for your storage needs or future finishing. With zero-maintenance front porch PVC railings, a freshly sealed level asphalt driveway, and an incredibly low HOA fee of just $115/year, this move-in-ready gem is an absolute must-see!

4 Beds ⋅ 3 Baths

Welcome home to 100 Winns Circle, perfectly situated on a generous 0.4-acre corner lot in Pioneer Heights. Located less than 5 minutes from Route 7 east of Winchester, this beautifully updated property offers the rare combination of neighborhood living without close neighbors or crowded structures. Step inside to find a freshly painted interior bathed in natural light, thanks to oversized Andersen windows and new LED lighting throughout. The main level features gleaming hardwood floors in the formal dining room and a massive living room centered around a magnificent floor-to-ceiling stone wood-burning fireplace. From here, premium patio swing doors open to a large rear deck—ideal for entertaining or relaxing. The kitchen is a chef's delight, outfitted with pristine oak cabinets, Corian countertops, brand-new LVP flooring, and new appliances, including a side-by-side refrigerator and slim-profile microwave. Upstairs, the layout is designed for modern living. The spacious primary suite acts as a private wing, cleverly partitioned away from the other bedrooms to include a dedicated home office space and a large bath with a two-person Jacuzzi tub. Practical upgrades abound, ensuring total peace of mind: a new second-floor gas furnace and A/C (warranty conveys), a new 50-gallon gas water heater, a new radon fan system, and upgraded blown-in attic insulation. The oversized two-car garage features a newly epoxied floor, built-in shelving, an extra refrigerator, and a convenient door to the rear deck. Below, an expansive walkout basement with double doors, a concrete patio, and a workshop area stands ready for your storage needs or future finishing. With zero-maintenance front porch PVC railings, a freshly sealed level asphalt driveway, and an incredibly low HOA fee of just $115/year, this move-in-ready gem is an absolute must-see!

100 Winns Cir, Winchester

Listing courtesy of NetRealtyNow.com, LLC. Contact:

$360,000

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! Selling As Is, No Repairs.

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! Selling As Is, No Repairs.

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:

$324,900

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. This is a on eowner home.It has been well taken care of.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. This is a on eowner home.It has been well taken care of.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:

$342,000

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:

$400,000

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:

$437,000

Move-In Ready & No HOA in the Heart of Winchester! Welcome to this charming and spacious brick rancher offering timeless construction, incredible versatility, and a brand-new roof (October 2026)! Featuring 3 bedrooms and 3 full baths, the main level boasts soaring tall ceilings, fresh paint, gleaming hardwood floors, and a cozy fireplace. The main floor also offers a versatile sunroom with a private entrance and a well-appointed kitchen equipped with stainless steel appliances. Head down to the expansive basement, complete with its own kitchen, a large storage room, a second fireplace, and a separate entrance—creating an incredible opportunity for rental income or guest space. Step outside to a spacious, fully fenced backyard featuring a handy storage shed. Additional highlights include an oversized attached garage for ample parking. Located just steps from the Winchester Country Club and minutes from local shopping, dining, and commuter routes, this home truly has it all. Plus, a one-year Home Warranty to give you total peace of mind!

3 Beds ⋅ 3 Baths

Move-In Ready & No HOA in the Heart of Winchester! Welcome to this charming and spacious brick rancher offering timeless construction, incredible versatility, and a brand-new roof (October 2026)! Featuring 3 bedrooms and 3 full baths, the main level boasts soaring tall ceilings, fresh paint, gleaming hardwood floors, and a cozy fireplace. The main floor also offers a versatile sunroom with a private entrance and a well-appointed kitchen equipped with stainless steel appliances. Head down to the expansive basement, complete with its own kitchen, a large storage room, a second fireplace, and a separate entrance—creating an incredible opportunity for rental income or guest space. Step outside to a spacious, fully fenced backyard featuring a handy storage shed. Additional highlights include an oversized attached garage for ample parking. Located just steps from the Winchester Country Club and minutes from local shopping, dining, and commuter routes, this home truly has it all. Plus, a one-year Home Warranty to give you total peace of mind!

131 Country Club Cir, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

How much is your home worth?

How much is your home worth?