Winchester, VA Homes

/23
$300,000
- 2 Beds
- 2 Baths
- 1,446 Sq Ft
209 S Braddock St, Winchester, VA 22601

Opportunity is knocking! Here's your chance to purchase a unique home in the beautiful Winchester Historic district. Freshly painted interior is light and bright-Step inside to hardwood flooring on your left is the formal living room featuring a decorative brick fireplace with a mantel to display your treasures, on the main level you will find a full bath, laundry, and kitchen with Tiled Floors-

Manuela Moyer Long & Foster Real Estate, Inc.

209 S Braddock St, Winchester, VA 22601
/14
$2,600 per month
- 4 Beds
- 2.5 Baths
- 1,940 Sq Ft
- House for Rent
2004 Taylor Grace Ct, Winchester, VA 22601

Spacious single family house featuring 4 bedrooms, 2.5 bathrooms, full unfinished basement, deck, fenced backyard, and two attached car garage.

Minh-Thieng Le Levi Clarke, LLC

2004 Taylor Grace Ct, Winchester, VA 22601
/26
$255,000 Sold Jul 01, 2025
- 1,080 Sq Ft
- $236/SF
- 4 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1986
237 Kimberly Way, Winchester, VA 22601

This beautifully renovated 2-bedroom, 1.5-bath townhouse features a spacious deck and a fenced backyard—perfect for outdoor entertaining. Enjoy fresh landscaping and stylish updates throughout. Ideally located within walking distance to downtown Winchester and Jim Barnett Park, and just minutes from shopping, Shenandoah University, and Winchester Medical Center. A perfect blend of comfort and

Leah Clowser RE/MAX Roots

237 Kimberly Way, Winchester, VA 22601

/46
Est $496,983 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,568 Sq Ft
605 Kernstown Ct, Winchester, VA 22601

605 Kernstown Ct, Winchester, VA 22601

/91
$959,000
- 4 Beds
- 4.5 Baths
- 6,566 Sq Ft
1509 Stone House Ct, Winchester, VA 22601

Perched on the edge of the walking trail with fall views of the lake, and host to a private oasis in the back yard, you'll find 1509 Stone House Court, one of the largest homes in Morlyn Hills. The current owners added the pool, extensive hardscaping, retainer walls, privacy fence, and a composite deck with angled stairs to the pool area. Marble floors welcome you to a light filled foyer that

Natalie Langford ERA Oakcrest Realty, Inc.

1509 Stone House Ct, Winchester, VA 22601
/13
$4,130 per month
- 9 Beds
- 2 Baths
- 1,650 Sq Ft
- House for Rent
548 -1/2 N Loudoun St Unit B, Winchester, VA 22601

Spacious 9-Bedroom, 2-Bath Apartment – Over 1,600 Sq Ft – Near Historic Downtown Winchester -Housing Vouchers WelcomeThis generously sized apartment offers over 1,600 square feet of living space with 9 bedrooms and 2 full bathrooms—perfect for large families, shared living arrangements, or agency housing needs. Located just a short walk from the charming and vibrant Old Town Winchester

Robert Adams Weichert Realtors - Blue Ribbon

548 -1/2 N Loudoun St Unit B, Winchester, VA 22601
/35
$540,000 Sold Jul 01, 2025
- 1,976 Sq Ft
- $273/SF
- 26 Days On Market
- 4 Beds
- 4 Baths
- Built 2008
2008 Taylor Grace Ct, Winchester, VA 22601

Wonderful location in Park Place subdivision near city park. Finished basement that includes a large recreation room and possible 5th bedroom with full bath. Bring the pets! Fenced back yard. Lots of upgrades to include, crown molding, chair rail and shadowboxes. Eat in kitchen opens to family room and large deck. Gas cooking with double oven and all stainless steel appliances. Shows

Kent Mull Link Realty Services LLC

2008 Taylor Grace Ct, Winchester, VA 22601

/67
Est $522,531 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,732 Sq Ft
624 Kernstown Ct, Winchester, VA 22601

624 Kernstown Ct, Winchester, VA 22601

/26
$385,000
- 3 Beds
- 2.5 Baths
- 1,536 Sq Ft
1004 S Cameron St, Winchester, VA 22601

PRICE REDUCED***Renovated Home in Winchester neighborhood.*** You’ll enter the house and find a spacious living room. As you continue walking, you’ll be led to the fully renovated kitchen. The kitchen features stainless steel appliances, including a new refrigerator, stove, microwave, dishwasher, new cabinets, and a granite countertop. The laundry room, located conveniently on the main level,

Patricia Salgado Metas Realty Group, LLC

1004 S Cameron St, Winchester, VA 22601
/11
$2,968 per month
- 6 Beds
- 2 Baths
- 1,500 Sq Ft
- House for Rent
548 N Loudoun St Unit B, Winchester, VA 22601

Spacious 6-Bedroom, 2-Bath Apartment – Over 1,500 Sq Ft – Near Historic Downtown Winchester -Housing Vouchers WelcomeThis generously sized apartment offers over 1,500 square feet of living space with 6 bedrooms and 2 full bathrooms—perfect for large families, shared living arrangements, or agency housing needs. Located just a short walk from the charming and vibrant Old Town Winchester

Robert Adams Weichert Realtors - Blue Ribbon

548 N Loudoun St Unit B, Winchester, VA 22601
/45
$335,000 Sold Jun 30, 2025
- 1,360 Sq Ft
- $246/SF
- 1 Day On Market
- 2 Beds
- 2.5 Baths
- Built 2020
1310 S Kent St, Winchester, VA 22601

Welcome to The Towns at Brooks Manor – where charm, comfort and convenience converge in this beautifully crafted end-unit townhome in Downtown Winchester. Step inside and experience the bright, open-concept floor plan—perfect for both everyday living and effortless entertaining. The main level features gleaming hardwood floors, a spacious living area, and a sleek, modern kitchen outfitted with

Laura White ERA Oakcrest Realty, Inc.

1310 S Kent St, Winchester, VA 22601

/38
Est $506,388 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,312 Sq Ft
3022 Saratoga Dr, Winchester, VA 22601

3022 Saratoga Dr, Winchester, VA 22601

/143
$950,000
- 5 Beds
- 4.5 Baths
- 4,438 Sq Ft
769 Seldon Dr, Winchester, VA 22601

Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living.The main level features a generously sized primary suite with a walk-in closet and en-suite bath,

Amanda Slate Keller Williams Realty

769 Seldon Dr, Winchester, VA 22601
/26
$1,850 per month
- 2 Beds
- 1 Bath
- 1,320 Sq Ft
- House for Rent
331 E Piccadilly St, Winchester, VA 22601

Super charming 1930's 3 bedroom 1 bathroom duplex just blocks from Old Town Winchester! This unit has been recently remodeled with an updated bathroom, flooring and light fixtures. You'll find the original wood floors, a large front porch, a fenced in backyard and spacious outbuilding. Pets allowed on a case by case basis, tenant pays all utilities, washer and dryer in basement, updated heating

Holly Graham Realty ONE Group Old Towne

331 E Piccadilly St, Winchester, VA 22601
/32
$365,000 Sold Jun 30, 2025
- 1,745 Sq Ft
- $209/SF
- 8 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2005
2079 Stoneleigh Dr, Winchester, VA 22601

Beautifully Maintained End-Unit Townhome in the City of WinchesterDon’t miss this rare opportunity to own a stunning 3-level end-unit townhome, impeccably maintained by its original owner. Located in the City of Winchester, this home offers timeless charm and modern updates throughout.The main level features gleaming hardwood floors, elegant crown molding, and an open-concept

Jeanne Mezzatesta Colony Realty

2079 Stoneleigh Dr, Winchester, VA 22601

/5
Est $298,402 Not Listed For Sale
329 Longview Ave, Winchester, VA 22601

329 Longview Ave, Winchester, VA 22601

/25
$359,900
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
553 Highland Ave, Winchester, VA 22601

Completely remodeled! Come enjoy ALL new everything, new electric, new windows, luxury floors, freshlypainted walls and brand-new custom kitchen and bathrooms, and all new plumbing and electricthroughout, nothing has been left untouched! New Mini Split HVAC system. Large living room opens into a gorgeous wrap aroundpeninsula kitchen with brand new Samsung appliances, granite

Lawrence Lessin Homes By Owner, Inc.

553 Highland Ave, Winchester, VA 22601
/39
$1,600 per month
- 2 Beds
- 1.5 Baths
- 920 Sq Ft
- Townhouse for Rent
527 Gray Ave Unit 2, Winchester, VA 22601

Unit fully renovated, professionally cleaned and ready for immediate move in. Washer/dryer hook ups in unit, Pets allowed on a case by case basis, Trash, water, sewer and all exterior maintenance included in rent. Owner looking for 640 credit score or better.

Joshua Jenkins Samson Properties

527 Gray Ave Unit 2, Winchester, VA 22601
/12
$375,000 Sold Jun 30, 2025
- 1,372 Sq Ft
- $273/SF
- 13 Days On Market
- Studio
- Built 1920
122 E Pall Mall St, Winchester, VA 22601

Renovated Duplex in Downtown Winchester – A Must-See Investment Opportunity!Discover this beautifully renovated duplex located in the heart of Downtown Winchester. Each unit features a stunning new kitchen redesign with: Gorgeous cabinets Granite countertops Large kitchen island with plenty of counter space Stainless steel appliances New LED recessed

Kathy Colville Century 21 Redwood Realty

122 E Pall Mall St, Winchester, VA 22601

/43
Est $436,285 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,355 Sq Ft
2817 Broadview St, Winchester, VA 22601

2817 Broadview St, Winchester, VA 22601

/56
$875,000
- 5 Beds
- 4.5 Baths
- 5,254 Sq Ft
1504 Brookdale Ct, Winchester, VA 22601

Paint/Carpet allowance up to $15,000 credit with an acceptable offer.Stunning 5BR/3.5BA Home in Prime Meadow Branch Area!Elegant 2-story foyer with sweeping staircase, coffered ceilings, and extended-height windows. Family room features floor-to-ceiling stone fireplace, open to gourmet kitchen with quartz countertops, stainless steel appliances, cooktop, and wall oven. Main level office

Julie Shiley Coldwell Banker Realty

1504 Brookdale Ct, Winchester, VA 22601
/31
$1,499 per month
- 2 Beds
- 3 Baths
- 1,148 Sq Ft
- Townhouse for Rent
1113 Franklin St Unit 1109, Winchester, VA 22601

Ready to Move In now, Cute Town-home, Complete house hardwood floor with 2 huge bedroom and walking closet on upper floor with one full bathroom and one bedroom has its own 1/2 bathroom,On Main Floor large living room and eat in kitchen dining combo with one half bathroom and laundry hook up ,House is located at end of the street right side of CUL-DE-SAC and next to I-81 exit 315 Rt.7 ,

Ram Beladia First American Real Estate

1113 Franklin St Unit 1109, Winchester, VA 22601
/26
$285,000 Sold Jun 30, 2025
- 963 Sq Ft
- $296/SF
- 49 Days On Market
- 3 Beds
- 1 Bath
- Built 1948
701 Watson Ave, Winchester, VA 22601

Immaculate Renovation of 3 Bedroom and 1 Bath Single Family Home*New Kitchen Includes: New White Cabinets, New Quartz Countertop, New Stainless Steel Appliances, New Ceramic Tile Flooring*Refinished Hardwood Floors*New Windows*New HVAC*All New Bathroom*Newer Roof, Gutters and Downspouts*New Side Porch and Decking*New Exterior Doors*New Recessed Lights*New Washer and Dryer*Full Unfinished

Gary Green Samson Properties

701 Watson Ave, Winchester, VA 22601

/39
Est $430,539 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,560 Sq Ft
421 Longview Ave, Winchester, VA 22601

421 Longview Ave, Winchester, VA 22601

/5
$289,500
- 4 Beds
- 1 Bath
- 1,732 Sq Ft
1006 S Cameron St, Winchester, VA 22601

Don't miss out on this opportunity to own this 5 bedroom/1 bath home. Hardwood flooring throughout. Large, covered front porch and rear deck. Less than a mile from downtown Winchester & the Handley Library. Close to schools. Off-street parking and a spacious backyard. Access to alley from backyard and off-street parking.

Sheila Pack RE/MAX Roots

1006 S Cameron St, Winchester, VA 22601
/14
$1,800 per month
- 1 Bed
- 1 Bath
- 826 Sq Ft
- House for Rent
122 N Loudoun St Unit 204, Winchester, VA 22601

Enjoy this beautiful luxury flat located in the heart of Old Town Winchester. Floor to ceiling windows, gleaming hardwood floors and natural quartz counter tops will leave you asking for nothing. This contemporary design includes keyless entry, dish TV, reserved parking in Loudoun Street Autopark and free Wi-Fi. You can also enjoy the upscale appliance which include washer/dryer. Electric to be

Dave Spence RE/MAX Roots

122 N Loudoun St Unit 204, Winchester, VA 22601
/28
$314,900 Sold Jun 30, 2025
- 1,373 Sq Ft
- $229/SF
- 187 Days On Market
- 3 Beds
- 1 Bath
- Built 1930
129 E Monmouth St, Winchester, VA 22601

HUGE PRICE REDUCTION. A beautifully updated home in the perfect spot to enjoy all of the excitement of downtown living. A short walk brings you to the historic walking mall; amidst the shops, restaurants and entertainment. Take advantage of First Fridays, Apple Blossom festivities and Old Town events throughout the year. Enjoy the large front and back porches for relaxing with a nice drink and a

Jimmy Biedrzycki CENTURY 21 New Millennium

129 E Monmouth St, Winchester, VA 22601

/38
Est $437,337 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
425 Longview Ave, Winchester, VA 22601

425 Longview Ave, Winchester, VA 22601

/45
$399,900
- 4 Beds
- 1.5 Baths
- 2,860 Sq Ft
684 Berryville Ave, Winchester, VA 22601

Come check out this 4-bedroom 1.5 bath 4 level Brick Colonial with a Detached Garage all on a double lot, updated roof, windows, new plumbing & water heater, updated electric & panel box. There is plenty of room to grow and put your flavor in the walk-up attic and basement. Home has the original Hardwood floors & Beautiful Woodworking that has never been painted on the main level. Large, Covered

Richard Kozlowski Long & Foster Real Estate, Inc.

684 Berryville Ave, Winchester, VA 22601
/32
$2,200 per month
- 4 Beds
- 1.5 Baths
- 1,800 Sq Ft
- House for Rent
317 S Kent St, Winchester, VA 22601

For Rent: 317 S Kent St, Winchester, VA.Live in the heart of historic downtown Winchester! This spacious 4-bedroom, 1.5-bath home offers 1,800 square feet of charm and comfort, just a short walk from shops, restaurants, and Shenandoah University. With front and back porches, a flat private backyard, and plenty of room to spread out, its ideal for student roommates, faculty, or anyone seeking

Sarah Abderrazzaq Realty ONE Group Old Towne

317 S Kent St, Winchester, VA 22601
/41
$365,000 Sold Jun 27, 2025
- 1,727 Sq Ft
- $211/SF
- 11 Days On Market
- 3 Beds
- 2 Baths
- Built 1948
512 Dunlap St, Winchester, VA 22601

Conveniently located near Route 7 and I-81, this beautiful all-brick home offers easy access to everything Winchester has to offer. Situated in the heart of the city, you're just minutes from downtown, schools, shopping, Jim Barnett Park, and a variety of entertainment options. Inside, the main level features classic hardwood floors, a full bathroom, and a cozy wood-burning fireplace — perfect

Sheila Pack RE/MAX Roots

512 Dunlap St, Winchester, VA 22601

/33
Est $422,771 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,366 Sq Ft
417 Circle Dr, Winchester, VA 22601

417 Circle Dr, Winchester, VA 22601

/58
$1,129,000
- 6 Beds
- 5.5 Baths
- 6,174 Sq Ft
1020 Breckinridge Ln, Winchester, VA 22601

A place to grow, gather, and stay awhile! From the moment you arrive, this property greets you with thoughtful details and a sense of home you can feel. A brick-paved, rocking chair-worthy front porch sets the tone, and the charming side porch with composite decking is both stylish and maintenance-free. This spacious 6+ bedroom/5.5 bath residence features a main-level bedroom and full bath—ideal

Sheila Pack RE/MAX Roots

1020 Breckinridge Ln, Winchester, VA 22601
/5
$1,199 per month
- 1 Bed
- 1 Bath
- 450 Sq Ft
- Condo for Rent
3107 3107 Shawnee Dr Unit 6, Winchester, VA 22601

Welcome to 3107 Shawnee Drive, Apartment #6. This newly renovated one-bedroom, one bathroom apartment home offers the best of all worlds. Luxury vinyl plank flooring throughout the entire unit. Open kitchen concept with brand new white cabinets with barrel handle, granite countertops,. Your newly renovated bathroom offers ample storage. Enjoy the spacious closet in the bedroom for all of your

Steve DuBrueler Coldwell Banker Premier

3107 3107 Shawnee Dr Unit 6, Winchester, VA 22601
/38
$499,000 Sold Jun 27, 2025
- 2,926 Sq Ft
- $171/SF
- 3 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1964
305 W Whitlock Ave, Winchester, VA 22601

Welcome to 305 W. Whitlock, also known as 'Walkable Whitlock'! Imagine the ease of strolling to Handley High School, enjoying a delicious dinner at Oakstone, or exploring the chic shops and Old Town events just a short walk from your doorstep.Walkable Whitlock offers the perfect blend of convenience and lifestyle. Picture yourself relaxing on your spacious front patio, hosting a summer

Gillian Greenfield Coldwell Banker Premier

305 W Whitlock Ave, Winchester, VA 22601

/36
Est $502,297 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,600 Sq Ft
2816 Baldwin St, Winchester, VA 22601

2816 Baldwin St, Winchester, VA 22601

/28
$339,900
- 3 Beds
- 1 Bath
- 1,376 Sq Ft
230 Allison Ave, Winchester, VA 22601

Welcome to 230 Allison Avenue, a recently renovated 3-bedroom, 1-bath home on a spacious 0.23-acre lot in Winchester. Ideally located just 1 mile from Winchester Medical Center and only minutes to Walmart Supercenter, shops, restaurants, and vibrant downtown Winchester, this home offers both convenience and charm. Step inside to discover a thoughtfully updated interior featuring luxury vinyl

Jon Fleming Weichert Realtors - Blue Ribbon

230 Allison Ave, Winchester, VA 22601
/18
$2,000 per month
- 3 Beds
- 1.5 Baths
- 1,780 Sq Ft
- House for Rent
433 Highland Ave, Winchester, VA 22601

Totally updated and refreshed! Adorable 3 bedroom, 1 and a half bath single family home, ready for occupancy 6/1/25. Large home with spacious addition in the back, which could be used as a fourth bedroom. Big kitchen with loads of cabinet and counter space, two living areas, huge dining room, and a cute half bath on the main level. Tenants pay all utilities. Pets considered on a case-by-case

Amanda White Nova Home Hunters Realty

433 Highland Ave, Winchester, VA 22601
/37
$251,111 Sold Jun 27, 2025
- 1,341 Sq Ft
- $187/SF
- 12 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1921
372 Gray Ave, Winchester, VA 22601

Enjoy the charm of this all-brick traditional home with lovely hardwood floors throughout. Nice size primary bedroom, all bedrooms have closets, and several recent updates in 2024 make this home absolutely move-in ready! You can decide if you prefer relaxing on your front or back porch or enjoying coffee on your rear balcony. There is also a back patio area if you want to grill your favorite

Pamela Foltz Realty ONE Group Old Towne

372 Gray Ave, Winchester, VA 22601

/52
Est $407,149 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,702 Sq Ft
209 W Cedarmeade Ave, Winchester, VA 22601

209 W Cedarmeade Ave, Winchester, VA 22601

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