Winchester, VA Homes for Sale under $500,000

/2
$250,000
- Land
- 5 Acres
- $50,000 per Acre
341 Laurel Grove Rd, Winchester, VA 22602

THERE ARE 2 -5 ACRE BUILDING LOTS W/4 BR CONVENTIONAL PERKS APPROVED. LOT 3 IS UP ON THE HILL AND LOT 4 FRONTS THE ROAD. THESE LOTS ARE CREATED FROM A LARGER PARCEL BY WAY OF A BOUNDRY LINE ADJUSTMENT. NEW PLATS AND BOUNDRY LINE ADJUSTMENTS INCLUDED IN DOCUMENTS. NEW DEEDS WILL BE ISSUED AT CLOSING. TAX ASSESSMENTS AND TAXES ARE BASED ON THE ENTIRE PROPERTY PRIOR TO BOUNDRY LINE ADJUSTMENT. NEW

Barbara Singhas Crum Realty, Inc.

341 Laurel Grove Rd, Winchester, VA 22602
/46
$360,000

$10K PRICE DROP
- 4 Beds
- 3 Baths
- 2,362 Sq Ft
300 Elk Trail, Winchester, VA 22602

Looking for a newer home with room to spread out and a peaceful wooded setting? Welcome to 300 Elk Trail.Built in 2021 and tucked among the trees in the Mountain Falls/Wilde Acres area, this 4-bedroom, 3-bath home offers the perfect blend of modern convenience and country living. The open main level creates a welcoming space for gathering with family and friends, while the finished lower

Abby Walters Preslee Real Estate

300 Elk Trail, Winchester, VA 22602
/78
$260,000
- 2 Beds
- 1.5 Baths
- 1,068 Sq Ft
103 E Germain St, Winchester, VA 22601

Roof replaced in 2020.Welcome to 103 E Germain St, a charming end-of-row townhouse just blocks from downtown Winchester! Enjoy easy access to restaurants, shops, breweries, entertainment, and historic attractions while enjoying low-maintenance living. The bright main level features an open floor plan, beautiful hardwood flooring, a spacious living room, kitchen, and dining area, plus a

RoxAnn Grimes RE/MAX Roots

103 E Germain St, Winchester, VA 22601
/11
$340,000
- 3 Beds
- 2 Baths
- 1,092 Sq Ft
197 Denny Ln, Winchester, VA 22603

Charming 3-bedroom, 2-bathroom cottage located off Berryville Ave. This inviting home features a large fully fenced back yard complete with a firepit, perfect for outdoor gatherings and relaxation.On the main level, you'll find two cozy bedrooms, kitchen with stainless appliances and a living room with shiplap accent wall. Upstairs, the spacious primary suite awaits, boasting a large dual

Stephanie Ambrogi Realty ONE Group Old Towne

197 Denny Ln, Winchester, VA 22603
/26
$400,000

$29K PRICE DROP
- 4 Beds
- 2 Baths
- 1,844 Sq Ft
1310 Whittier Ave, Winchester, VA 22601

Turn-key and move-in ready! This beautifully updated 4-bedroom, 2-bath home features a modern kitchen with recently updated appliances, a new HVAC system, and a new hot water heater for added peace of mind. Enjoy the spacious backyard, perfect for outdoor entertaining, along with convenient off-street parking and the freedom of no HOA. Nestled in an established neighborhood with large yards and a

Sarah Hott Realty ONE Group Old Towne

1310 Whittier Ave, Winchester, VA 22601
/32
$310,000
- 3 Beds
- 2 Baths
- 1,532 Sq Ft
204 Cochise Trail, Winchester, VA 22602

Adorable rancher in Shawneeland with access to a lake, trails, beach, and fishing. Ideally you wish for spacious living quarters,3 bedrooms, 2 full baths, and a walkout basement with a finished room for gym/office/den..well we have all that and more so come take a gander and make it your own before the summer ends.

Dave Spence RE/MAX Roots

204 Cochise Trail, Winchester, VA 22602
/78
$410,000

$85K PRICE DROP
- Land
- 20 Acres
- $20,500 per Acre
000 Light Rd, Winchester, VA 22603

Gentle stretches of open meadow roll into quiet, wooded groves where sunlight filters through the trees. Hidden among them, peaceful little ponds shimmer like jewels, inviting you to pause and simply breathe. Imagine sundrenched mornings, afternoons exploring your own private trails, and evenings watching the sky glow across wide open fields. Whether you long to build a cozy retreat, a forever

Melissa Johnston ERA Oakcrest Realty, Inc.

000 Light Rd, Winchester, VA 22603
/64
$359,000

$16K PRICE DROP
- 3 Beds
- 1 Bath
- 1,474 Sq Ft
805 Pennsylvania Ave, Winchester, VA 22601

Lovingly maintained, this charming brick rancher is the perfect starter home or investment opportunity! The main level offers three comfortable bedrooms, one full bath, a bright eat-in kitchen, and a spacious living room filled with natural light. The full unfinished basement provides endless potential for additional finished living space, while an existing hobby room is already in place—perfect

Sherry Santmyer Hunt Country Sotheby's International Realty

805 Pennsylvania Ave, Winchester, VA 22601
/45
$315,000

$35K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,728 Sq Ft
913 Orchard Hill Dr, Winchester, VA 22601

New roof, new windows, all brick exterior, wood burning fireplace, screened porch. Perfect opportunity for buyers to bring the interior of the property to neighborhood standards and enhance the value through sweat equity. This home has a great floor plan and an enviable location in beautifully maintained, established area. Located with easy access to amenities, shopping and commuter

Dallas Croft Samson Properties

913 Orchard Hill Dr, Winchester, VA 22601
/31
$384,000

$14K PRICE DROP
- 3 Beds
- 2 Baths
- 1,552 Sq Ft
103 Elaine Dr, Winchester, VA 22602

This is the one you’ve been waiting for — a beautifully maintained ranch‑style home with thoughtful updates and a bright, comfortable layout throughout. A newer roof, updated HVAC, and fresh carpet provide peace of mind and move‑in readiness from day one.The primary ensuite serves as a true retreat, featuring a spa‑like bath and a walk‑in closet. Two additional bedrooms offer flexible living

LESLIE WEBB Long & Foster Real Estate, Inc.

103 Elaine Dr, Winchester, VA 22602
/37
$399,900
- 3 Beds
- 2 Baths
- 1,176 Sq Ft
163 Margaret Ln, Winchester, VA 22603

(Magnificent Margaret) This home has a lot to offer: All bedrooms and bathrooms on the main level, fully updated kitchen with Stainless Steel Appliances (Fridge, Dishwasher, Stove, Microwave) Quartz counter top, built in pantry, remodeled bathrooms with a double vanity in the primary bathroom and a walk-in tile shower, Central Heating & Air, New windows, Laundry room, large driveway, two car

Michael Sprague Samson Properties

163 Margaret Ln, Winchester, VA 22603
/27
$339,999
- 3 Beds
- 2.5 Baths
- 1,848 Sq Ft
113 Windmill Ln, Winchester, VA 22602

Why rent when you can own? This spacious townhome has everything you are looking for. Located steps away from Route 7 & I Interstate 81, with grocery stores, pharmacy and restaurants. Who needs to go out when you can entertain at home. LARGE rooms, well equipped Kitchen w/ walk-in Pantry & Island, Microwave & Glass Top cooking Range & durable easy to clean Corian Countertops. Kitchen flows to

Sarah Hott Realty ONE Group Old Towne

113 Windmill Ln, Winchester, VA 22602
/71
$339,900

$10K PRICE DROP
- 3 Beds
- 2 Baths
- 1,673 Sq Ft
904 Archwood Trail, Winchester, VA 22602

"Escape To Archwood" Whether you're looking for a weekend retreat or a primary residence this 3-bedroom, 2-bathroom Chalet Style home is it! With incredible mountain views, privacy and room to stretch out this home can be your happy place! Open concept on the upper level with vaulted ceilings and a large kitchen with stainless steel appliances. Primary bedroom with a sliding door to the deck and

Matt Kilmer Samson Properties

904 Archwood Trail, Winchester, VA 22602
/58
$489,990

New Construction $40K PRICE DROP
- 4 Beds
- 2.5 Baths
- 1,971 Sq Ft
251 Rossmann Blvd, Winchester, VA 22602

The home is move-in ready, with a full basement, preselected upgrades, and a one-year home warranty. Welcome to this beautifully crafted new-construction home by a respected local builder, offering almost 2,000 square feet of thoughtfully designed living space in the desirable Sovereign Village community, with room to grow in the improved basement. The inviting, open-concept main level features a

Marisa Varley ERA Oakcrest Realty, Inc.

251 Rossmann Blvd, Winchester, VA 22602
/20
$449,990

New Construction
- 3 Beds
- 2.5 Baths
- 1,657+ Sq Ft
CABRAL Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

The Cabral, a 1,657 square foot two-story home, offers an open-concept design perfect for modern living. Featuring three bedrooms, two and a half bathrooms, a versatile loft, and a two-car garage, this home is ideal for families seeking both space and functionality. Upon entering through the front porch, you'll find a convenient first-floor powder room and coat closet in the foyer. The spacious

D.R. Horton Builder

137 Seminole Dr Unit 36203778, Winchester, VA 22602
/2
$300,000
- 3 Beds
- 1 Bath
- 1,008 Sq Ft
111 Haven Terrace, Winchester, VA 22602

Charming 3-Bedroom Rambler on a Spacious Lot! Welcome to 111 Haven Terrace, a conveniently located 3-bedroom, 1-bath rambler situated on approximately 0.26 acres. This single-level home offers a practical layout with comfortable living spaces and plenty of potential to make it your own.The main-level living design provides easy access throughout the home, making this property a great fit

Erin Kavanagh EXP Realty, LLC

111 Haven Terrace, Winchester, VA 22602
/45
$260,000
- 2 Beds
- 1 Bath
- 997 Sq Ft
108 Martin Dr, Winchester, VA 22602

Attention investors! Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-81—an ideal location for commuters. The property offers a driveway and a carport, perfect for convenient parking or doubling as a shaded outdoor space for entertaining, along with generous storage space. Inside, you’ll find an open-concept living room and eat-in kitchen with large

Heloisa Amar Samson Properties

108 Martin Dr, Winchester, VA 22602
/63
$330,000
- 4 Beds
- 2 Baths
- 1,592 Sq Ft
805 S Kent St, Winchester, VA 22601

Very well-maintained 2-level home offering 4 bedrooms and 2 full baths in the heart of Winchester. This home features a functional layout with a blend of classic charm and thoughtful updates throughout. Pride of ownership shows inside and out, with comfortable living spaces, a fully fenced yard, and a private driveway for off-street parking. Conveniently located near downtown, shopping, and

Carolina Mosquera Weichert, REALTORS

805 S Kent St, Winchester, VA 22601
/17
$289,000

$6K PRICE DROP
- 3 Beds
- 1 Bath
- 960 Sq Ft
1314 S Braddock St, Winchester, VA 22601

1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room

Jacqueline Moore Open Door Brokerage, LLC

1314 S Braddock St, Winchester, VA 22601
/38
$329,000

Open Sun 12PM - 3PM $20K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,667 Sq Ft
204 Cougar Trail, Winchester, VA 22602

Nestled in the serene Wilde Acres subdivision, this charming split foyer home, built in 2020, offers a perfect blend of modern comfort and natural beauty. With 3 spacious bedrooms and 2.5 bathrooms, this residence is designed for both relaxation and entertaining. Step inside to discover a warm and inviting interior featuring laminated flooring throughout. The heart of the home is the combination

Gerald Owens Realty ONE Group Old Towne

204 Cougar Trail, Winchester, VA 22602
/28
$485,990

New Construction
- 4 Beds
- 2.5 Baths
- 1,953 Sq Ft
PINE Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

The Pine is a 1,953 square foot open concept home, offering four bedrooms, two and a half bathrooms and a two-car garage. A foyer with a powder room and coat closet greets you as you enter this home. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for

D.R. Horton Builder

137 Seminole Dr Unit 36203779, Winchester, VA 22602
/32
$329,900
- 3 Beds
- 2.5 Baths
- 1,488 Sq Ft
103 Trade Wind Ln, Winchester, VA 22602

Welcome home to 103 Trade Wind Lane, a beautifully updated townhome offering low-maintenance living on Winchester’s desirable east side! Perfectly situated near top schools, shopping, dining, and major commuter routes, this turn-key residence delivers both comfort and ultimate convenience. Natural light pours into the bright living room, where modern flooring lead you straight into the open

Dan Whitacre Colony Realty

103 Trade Wind Ln, Winchester, VA 22602
/17
$456,490

New Construction
- 3 Beds
- 2.5 Baths
- 1,657 Sq Ft
136 Wappinger Terrace, Winchester, VA 22602

Step into 1,657 square feet of well-designed living space in the Cabral, featuring 3 spacious bedrooms, 2.5 bathrooms, and a flexible loft upstairs—perfect for a home office, playroom, or additional lounge area. This home showcases a charming white siding exterior with stone accents, while the interior boasts sleek white kitchen and bathroom cabinets paired with modern finishes throughout. Enjoy

D.R. Horton Builder

136 Wappinger Terrace, Winchester, VA 22602
/51
$224,900

$34K PRICE DROP
- 2 Beds
- 2 Baths
- 1,173 Sq Ft
8 Brookland Ct Unit 8, Winchester, VA 22602

2 Bed, 2 bath condominium. New appliances, including water heater and heat pump. Gas fireplace, open concept with separate dining room. Patio/ porch with french doors and skylights in living room allow tons of natural light. Primary suite includes walk-in closet. Conveniently located off rt 7 and 81.

Vicki Broy RE/MAX Roots

8 Brookland Ct Unit 8, Winchester, VA 22602
/52
$369,990

New Construction
- 3 Beds
- 3.5 Baths
- 1,756 Sq Ft
229 Monteith Dr, Winchester, VA 22601

The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! 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. ***OFFERING UP TO $5K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED

Brittany Newman DRB Group Realty, LLC

229 Monteith Dr, Winchester, VA 22601
/39
$290,000

$25K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,170 Sq Ft
126 Marple Rd, Winchester, VA 22603

Charming Cape Cod-style home located at 126 Marple Rd in the desirable north end of Winchester! This well-maintained 3-bedroom, 1.5-bath home offers timeless character, functional living space, and a convenient commuter-friendly location. The main level features a bedroom with a 1/2 bath, a living room, a dining room, and a kitchen. Upstairs, you’ll find additional bedrooms with a shared

RoxAnn Grimes RE/MAX Roots

126 Marple Rd, Winchester, VA 22603
/33
$348,000

$12K PRICE DROP
- 3 Beds
- 2 Baths
- 1,554 Sq Ft
302 Wentworth Dr, Winchester, VA 22601

Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on

Heloisa Amar Samson Properties

302 Wentworth Dr, Winchester, VA 22601
/22
$334,000
- 3 Beds
- 2.5 Baths
- 1,680 Sq Ft
308 Fawn Dr, Winchester, VA 22602

Nestled in the charming Wilde Acres community, this delightful Colonial home offers a perfect blend of comfort and style. Built in 2009, this residence features 3 spacious bedrooms and 2.5 bathrooms, providing ample space for relaxation and daily living. The inviting layout encompasses 1,680 sq. ft. of thoughtfully designed living space, ideal for both entertaining and quiet evenings at home.

Steve DuBrueler Coldwell Banker Premier

308 Fawn Dr, Winchester, VA 22602
/32
$399,900

$29K PRICE DROP
- 2 Beds
- 2 Baths
- 1,419 Sq Ft
118 1/2 E Cork St, Winchester, VA 22601

Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural

Janet Flaherty Keller Williams Realty

118 1/2 E Cork St, Winchester, VA 22601
/33
$429,000
- 3 Beds
- 2 Baths
- 1,544 Sq Ft
1412 S Loudoun St, Winchester, VA 22601

Awesome Interior Photo's Coming Soon! Step inside this tastefully renovated brick ranch and feel instantly at home. Offering three comfortable bedrooms and two full baths, this property blends classic charm with thoughtful updates throughout. The main level features a bright, welcoming layout perfect for everyday living, while the lower level opens the door to exceptional flexibility — complete

LESLIE WEBB Long & Foster Real Estate, Inc.

1412 S Loudoun St, Winchester, VA 22601
/26
$374,990

New Construction
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
HomeSite 5 Shuoner Ct, Winchester, VA 22602

MOVE IN READYSt. Paul Townhome TBB | 3 BR | 2.5 BA | 1-Car Garage | Finished Lower LevelBeautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living designed for today's lifestyle.Home HighlightsOpen-concept main level — perfect for entertaining family and friendsGranite countertopsStainless steel

Jimmy Thomas New Home Star Virginia, LLC

HomeSite 5 Shuoner Ct, Winchester, VA 22602
/9
$379,990

New Construction
- 3 Beds
- 1.5 Baths
- 1,752 Sq Ft
109 Heirloom Way, Winchester, VA 22603

This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

Brookfield Residential Builder

109 Heirloom Way, Winchester, VA 22603
/19
$381,690

New Construction
- 4 Beds
- 3.5 Baths
- 1,889 Sq Ft
652 Arden Ct, Winchester, VA 22601

652 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

D.R. Horton Builder

652 Arden Ct, Winchester, VA 22601
/39
$498,000

New Construction
- 4 Beds
- 2.5 Baths
- 2,023 Sq Ft
39 Rossmann Blvd, Winchester, VA 22602

To be built-choose your colors and upgrades! Photos are similar and include upgrades. Beautifully crafted new home by a respected local builder, offering over 2,000 square feet of thoughtfully designed living space in the desirable Sovereign Village community. The inviting, open-concept main level features a spacious kitchen with a large island, perfect for gathering and entertaining, that

Marisa Varley ERA Oakcrest Realty, Inc.

39 Rossmann Blvd, Winchester, VA 22602
/14
$389,990

New Construction
- 3 Beds
- 4 Baths
- 1,905 Sq Ft
116 Swansong Place, Winchester, VA 22603

The three-level Skyline model masterfully combines a traditional exterior with a contemporary, open-concept floor plan. On the main level, you’ll find an expansive living room, bathed in natural light from numerous windows, flows effortlessly into the dining area and kitchen. The kitchen is designed with an L-shaped countertop and an island that borders the dining room. A cozy nook serves as a

Brookfield Residential Builder

116 Swansong Place, Winchester, VA 22603
/23
$349,990

New Construction
- 3 Beds
- 1.5 Baths
- 1,893 Sq Ft
117 Castaway Place, Winchester, VA 22603

This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

Brookfield Residential Builder

117 Castaway Place, Winchester, VA 22603
/15
$435,000
- 5 Beds
- 4 Baths
- 2,014 Sq Ft
122 Cherry Hill Cir, Winchester, VA 22602

Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting you to gather with loved ones during chilly evenings. The fully finished basement, complete with

Jen Moore ERA Oakcrest Realty, Inc.

122 Cherry Hill Cir, Winchester, VA 22602
/40
$399,900

New Construction
- 3 Beds
- 2.5 Baths
- 1,251 Sq Ft
709 Ross St, Winchester, VA 22601

NEW AND READY TO MOVE IN!!!BRAND NEW SINGLE FAMILY COLONIAL WITH 3 BEDROOM, 2.5 BATH! NO HOA!Be the first to call this beautiful new construction yours. Conveniently located just outside the City of Winchester and close to shopping, this home offers an open layout designed for entertaining. The great room leads into the spacious kitchen featuring an oversized island, granite countertops,

Donna Anderson Samson Properties

709 Ross St, Winchester, VA 22601
/27
$429,990

New Construction
- 4 Beds
- 3 Baths
- 2,168 Sq Ft
FREEPORT DUPLEX Plan at Willow Run - Duplexes, Winchester, VA 22601

Looking for a beautiful home that meets all your needs? Look no further than the Freeport! This stunning 1,492 square foot residence features three bedrooms, two baths, and a convenient two-car garage, all designed with your active adult lifestyle in mind.As you step into the foyer, you are greeted by the open-concept kitchen and living area with plenty of space for cooking, dining, and

D.R. Horton Builder

105 Trellis View Ln Unit 36406838, Winchester, VA 22601
/22
$371,990

New Construction
- 4 Beds
- 3.5 Baths
- 2,000 Sq Ft
HOMESITE 112 Shuoner Ct, Winchester, VA 22602

110 SHUONER Ct – Model Home | We Have spec homes Summer 2026 Delivery AvailableSt. Paul TBB | 4 BR | 3.5 BA | 1-Car Garage | Finished Lower Level + Larger DeckBeautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living — customize your home the way you like, or keep everything as-is at this price, including a 4th bedroom.Home

Jimmy Thomas New Home Star Virginia, LLC

HOMESITE 112 Shuoner Ct, Winchester, VA 22602

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