Winchester, VA Homes

/9
$1,300,000
- Land
- 64.91 Acres
- $20,028 per Acre
Lot 7 Cedar Creek Grade, Winchester, VA

Rare opportunity to own 64+ scenic acres on the desirable west side of Winchester, VA. This preservation parcel offers one building right and features a beautiful mix of open land and partial woodland, providing both usability and privacy. Formerly an apple orchard, the property is well suited for a small farm, specialty crops, or vineyard, with potential for additional uses with an approved

Lori Bales

Keller Williams Realty

(540) 974-1542

Lot 7 Cedar Creek Grade, Winchester, VA
/12
$2,200 per month
- 2 Beds
- 2 Baths
- 1,600 Sq Ft
- Condo for Rent
21 S Stewart St Unit 4, Winchester, VA 22601

Charming Remodeled 2-Bedroom Apartment Near Old Town Winchester!Enjoy the perfect mix of comfort and convenience in this beautifully remodeled 2 bedroom, 2 bathroom apartment located just steps from historic Old Town Winchester. This spacious unit features modern updates, in-unit laundry, and a fully fenced private yard—ideal for relaxing or entertaining. You'll also love the generous storage

Frank Armstrong, IV

Colony Realty

(540) 318-1292

21 S Stewart St Unit 4, Winchester, VA 22601
/69
$740,000 Sold Oct 29, 2025

170 Green Spring Rd, Winchester, VA 22603
- 4 Beds
- 4 Baths
- 2,740 Sq Ft
- Built 1999
Last Sold Summary
- $270/SF
- 13 Days On Market
Current Estimated Value $735,404

Last Listing Agent Kira Grubb Realty ONE Group Old Towne

170 Green Spring Rd, Winchester, VA 22603

/59
Est $537,893 Not Listed For Sale

1937 Harvest Dr, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,524 Sq Ft
- Built 2002
1937 Harvest Dr, Winchester, VA 22601

Last Sold Summary
- 2% Above List Price
- $208/SF
- 7 Days On Market
Last Sold Price $525,000

Last Listing Agent Karen O'Hare Colony Realty

/42
$599,000 Under Contract
- 3 Beds
- 2.5 Baths
- 2,964 Sq Ft
425 Briarmont Dr, Winchester, VA 22601

Welcome to a truly special opportunity in the heart of historic downtown Winchester. This inviting three-bedroom, 2.5 bath home offers the rare combination of one-level living, timeless charm, and an unbeatable walkable location. The fully renovated kitchen, completed in 2022, is absolutely gorgeous—featuring bright cabinetry, stunning quartz countertops, brand new appliances, and a fresh, modern

Lori Bales

Keller Williams Realty

(540) 274-1349

425 Briarmont Dr, Winchester, VA 22601
/11
$1,400 per month
- 1 Bed
- 1 Bath
- 15,699 Sq Ft
- Condo for Rent
44 S Loudoun St Unit 9, Winchester, VA 22601

Charming 1 bedroom, 1 bathroom apartment located on the Historic Downtown walking mall, with access to all of the Shops, restaurants, museums, and more right out the front door! Just minutes from Shenandoah University, Apple Blossom Mall, and Winchester Medical Center. Parking for each unit.

Brock Harris

Samson Properties

(540) 516-4753

44 S Loudoun St Unit 9, Winchester, VA 22601
/57
$630,000 Sold Jul 03, 2025

716 S Washington St, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 2,774 Sq Ft
- Built 1865
Last Sold Summary
- $227/SF
- 28 Days On Market
Current Estimated Value $634,092

Last Listing Agent Lisa Alberti Pearson Smith Realty, LLC

716 S Washington St, Winchester, VA 22601

/64
Est $543,029 Not Listed For Sale

605 Sterling Dr, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 2,746 Sq Ft
- Built 2003
605 Sterling Dr, Winchester, VA 22601

Last Sold Summary
- 9% Above List Price
- $182/SF
- 112 Days On Market
Last Sold Price $499,900

Last Listing Agent Brian Yoder Realty ONE Group Old Towne

/11
$624,880 New Construction
- 2 Beds
- 2 Baths
- 2,658 Sq Ft
159 Williamson Rd, Winchester, VA 22602

Richmond American Homes

Builder

159 Williamson Rd, Winchester, VA 22602
/74

$1,700 - $3,900 per month

The Local

1 - 4 Beds

230 Spring St, Winchester, VA 22601

Modern designs, elegant finishes, and the most desirable amenities await you at the areas newest apartment home living destination, the Local. Our Winchester apartments come in one, two, three, and four-bedroom floorplans, each featuring spacious and adaptable layouts. Various interior extras adorn them including an open floorplan concept, walk-in closets, in-unit washers/dryers, and more. As a

230 Spring St, Winchester, VA 22601
/65
$670,000 Sold Feb 03, 2026

521 Hidden Valley Ln, Winchester, VA 22603
- 3 Beds
- 4 Baths
- 2,973 Sq Ft
- Built 2001
Last Sold Summary
- 2% Above List Price
- $225/SF
- 10 Days On Market
Current Estimated Value $652,738

Last Listing Agent Kaitlyn Behr Samson Properties

521 Hidden Valley Ln, Winchester, VA 22603

/10
Est $281,360 Not Listed For Sale

1112 Opequon Ave, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,021 Sq Ft
- Built 1978
1112 Opequon Ave, Winchester, VA 22601

Last Sold Summary
- 4% Above List Price
- $264/SF
- 4 Days On Market
Last Sold Price $270,000

Last Listing Agent Ashley Wise Keller Williams Realty Advantage

/11
$61,900
- Land
- 0.69 Acre
- $89,710 per Acre
Lots 11 & 12 Glen Ridge Rd, Winchester, VA 22602

Entrance road, and road to this property now Paved! Amazing builder opportunity, new section availability. Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 698-4594

Lots 11 & 12 Glen Ridge Rd, Winchester, VA 22602
/51
$3,100 per month
- 4 Beds
- 3.5 Baths
- 3,164 Sq Ft
- House for Rent
2013 Taylor Grace Ct, Winchester, VA 22601

**Beautiful Brick-Front Colonial for Rent – Spacious, Finished Walk-Up Basement, Fenced Yard** Well-maintained brick-front home located in an established neighborhood with convenient access to Downtown Winchester, Apple Blossom Mall, shopping, restaurants, parks, and commuter routes. Impressive curb appeal with a large driveway accommodating 4+ vehicles and an oversized 2-car garage featuring

John Ginty Samson Properties

2013 Taylor Grace Ct, Winchester, VA 22601
/67
$620,000 Sold Aug 07, 2025

162 Darby Dr, Winchester, VA 22602
- 4 Beds
- 4 Baths
- 2,760 Sq Ft
- Built 2002
Last Sold Summary
- $225/SF
- 19 Days On Market
Current Estimated Value $620,075

Last Listing Agent Michael Elias Century 21 Redwood Realty

162 Darby Dr, Winchester, VA 22602

/54
Est $575,734 Not Listed For Sale

1905 Harvest Dr, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,946 Sq Ft
- Built 2001
1905 Harvest Dr, Winchester, VA 22601

Last Sold Summary
- 4% Above List Price
- $188/SF
- 3 Days On Market
Last Sold Price $554,000

Last Listing Agent Lisa Lowery Keller Williams Realty

/12
$54,900
- Land
- 0.73 Acre
- $75,205 per Acre
LOTS 7 & 8 Manor Dr, Winchester, VA 22602

Limited opportunity to pick up a prime building site in a desirable, rural community that is thriving and growing! High View Manor features lovely, new construction with some green space between homes, and mature trees all around. Ready to build lots just minutes from town, perfect for someone who wants to be in a community, but still have some space between neighbors. Lots 7 & 8 are being sold

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 565-5562

LOTS 7 & 8 Manor Dr, Winchester, VA 22602
/22

$1,908 - $2,489 per month

Meadow Branch Luxury Apartments

1 - 3 Beds

424 Ridgewood Ln, Winchester, VA 22601

Welcome to Meadow Branch, where luxury and convenience are standard. Our community offers beautiful 1,2 and 3 bedroom apartment homes. Community means convenience and at Meadow Branch, everything you need is nearby. We are conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

424 Ridgewood Ln, Winchester, VA 22601
/25
$410,000 Sold Apr 18, 2025

235 Bentley Ave, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 1,342 Sq Ft
- Built 1998
Last Sold Summary
- $306/SF
- 0 Days On Market
Current Estimated Value $408,598

Last Listing Agent Matt Baer MarketPlace REALTY

235 Bentley Ave, Winchester, VA 22602

/33
Est $376,158 Not Listed For Sale

1954 Cidermill Ln, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,711 Sq Ft
- Built 2012
1954 Cidermill Ln, Winchester, VA 22601

Last Sold Summary
- 4% Above List Price
- $210/SF
- 10 Days On Market
Last Sold Price $360,000

Last Listing Agent Sara Williams Century 21 Redwood Realty

/3
$674,990 New Construction
- 4 Beds
- 3 Baths
- 3,166 Sq Ft
156 Williamson Rd, Winchester, VA 22602

The Drexel home design is a spacious and versatile single-family home designed to suit a variety of lifestyles. With 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features main-level living with three bedrooms, including a private master suite with a walk-in closet and en-suite bathroom, along with two full bathrooms and a 2-car

Maronda Homes

Builder

156 Williamson Rd, Winchester, VA 22602
/2
$1,795 per month
- 3 Beds
- 2 Baths
- 1,004 Sq Ft
- Townhouse for Rent
107 Longstreet Ave, Winchester, VA 22603

Welcome to this recently completely renovated duplex unit in Winchester. Excellent location for commuters close to route 7 and I-81 as well as all the shopping in the area. This 3 Bedroom 2 Bath home has newer flooring throughout, newer paint. Updated kitchen and much more. Large backyard completely fenced in! Pets are welcome, there are certain breed restrictions for dogs, $250 pet deposit per

Jarrett Sowder RE/MAX Roots

107 Longstreet Ave, Winchester, VA 22603
/57
$480,000 Sold Jun 06, 2025

151 Morning Glory Dr, Winchester, VA 22602
- 4 Beds
- 2.5 Baths
- 2,532 Sq Ft
- Built 1992
Last Sold Summary
- $190/SF
- 17 Days On Market
Current Estimated Value $487,618

Last Listing Agent Gina Chatham Century 21 Redwood Realty

151 Morning Glory Dr, Winchester, VA 22602

/28
Est $372,024 Not Listed For Sale

336 Parkway St, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 1,620 Sq Ft
- Built 1964
336 Parkway St, Winchester, VA 22601

Last Sold Summary
- 1% Above List Price
- $228/SF
- 92 Days On Market
Last Sold Price $370,000

Last Listing Agent Teresa Strohmeyer ERA Oakcrest Realty, Inc.

/40
$549,900 Under Contract
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
435 Mikey Ct, Winchester, VA 22601

Welcome to 435 Mikey Court, a beautifully appointed home tucked within the highly desirable Village at Harvest Ridge, a premier 55+ community offering comfort, quality, and ease of living. Designed for effortless main-level living, this home features a well-thought-out open floorplan that connects the living, dining, and kitchen spaces, creating a warm and inviting atmosphere with generous room

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 530-3150

435 Mikey Ct, Winchester, VA 22601
/46

$1,700 - $2,670 per month

Stuart Hill

1 - 3 Beds

1981 Randolph Place, Winchester, VA 22601

Welcome to Stuart Hill Apartments comfortable living in scenic Winchester, VA. Nestled in the picturesque Shenandoah Valley and just minutes from Historic Downtown Winchester, dining, shopping, Shenandoah University, and Winchester Medical Center, this well-maintained community offers spacious 1-, 2-, and 3-bedroom homes with full-size in-unit washers and dryers, generous closet space, and

1981 Randolph Place, Winchester, VA 22601
/38
$621,490 Sold Nov 18, 2025

123 Hydrangea Way, Winchester, VA 22602
- 4 Beds
- 3 Baths
- 1,748 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $356/SF
- 19 Days On Market
D.R. Horton Willow Run

123 Hydrangea Way, Winchester, VA 22602

/73
Est $1,518,127 Not Listed For Sale

778 Johnston Ct, Winchester, VA 22601
- 6 Beds
- 8 Baths
- 10,500 Sq Ft
- Built 1998
778 Johnston Ct, Winchester, VA 22601

Last Sold Summary
- 8% Above List Price
- $133/SF
- 34 Days On Market
Last Sold Price $1,400,000

Last Listing Agent Carolyn Young Samson Properties

/2
$175,000
- Land
- 0.37 Acre
- $472,973 per Acre
719 Kennedy Dr, Winchester, VA 22601

Vacant Lot in Rolling HillsOne of the last opportunities to own a vacant lot in the desirable Rolling Hills community. This property offers the perfect setting to build your new home or presents an excellent opportunity for a long-term investment. Enjoy a well-established neighborhood with limited remaining buildable lots. Buyer to verify zoning, utilities, and intended use. Water and Sewer

Frank Armstrong, IV

Colony Realty

(540) 709-9357

719 Kennedy Dr, Winchester, VA 22601
/19
$2,100 per month
- 3 Beds
- 3.5 Baths
- 2,281 Sq Ft
- Townhouse for Rent
178 Solara Dr, Winchester, VA 22602

Well maintained/clean unit. Renter(s) must provide renter's insurancee. No pets or smoking.

Kathryn Hallett Long & Foster Real Estate, Inc.

178 Solara Dr, Winchester, VA 22602
/56
$545,000 Sold Nov 07, 2025

509 Marion St, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,691 Sq Ft
- Built 1992
Last Sold Summary
- $203/SF
- 3 Days On Market
Current Estimated Value $547,740

Last Listing Agent Mark Francis Real Broker LLC

509 Marion St, Winchester, VA 22601

/34
Est $437,337 Not Listed For Sale

105 Christopher Dr, Winchester, VA 22601
- 5 Beds
- 3 Baths
- 2,680 Sq Ft
- Built 1966
105 Christopher Dr, Winchester, VA 22601

Last Sold Summary
- 1% Above List Price
- $162/SF
- 53 Days On Market
Last Sold Price $433,000

Last Listing Agent Carolina Mosquera Weichert Corporate

/23
$310,000
- 3 Beds
- 1 Bath
- 1,134 Sq Ft
27 Jackson Ave, Winchester, VA 22601

Completely renovated and move-in ready, this charming 3 bedroom, 1 bath home is ideally located just minutes from downtown Winchester's shops, dining, and entertainment. Inside, you'll find beautiful hardwood floors throughout and a brand new kitchen and fully renovated bathroom. Major updates to the home include a new roof, new windows, new HVAC system, new hot water heater and new electric all

Mikiala Whitacre

ERA Oakcrest Realty, Inc.

(540) 590-5591

27 Jackson Ave, Winchester, VA 22601
/50

$1,843 - $3,374 per month

The Lofts at Jubal Square

1 - 3 Beds

1864 Old Jube Square, Winchester, VA 22601

Weve got it all at the Lofts at Jubal Square, the newest addition to the charming andhistoric Winchester cityscape. We offer a total commitment to better living, boasting largeapartments with loft and garage options, as well as amenities ideal for all those seeking anexceptional apartment lifestyle. Discover the Lofts at Jubal Square and discover what itmeans to live the good life.

1864 Old Jube Square, Winchester, VA 22601
/26
$235,000 Sold Jun 16, 2025

164 Brookland Ct Unit 10, Winchester, VA 22602
- 2 Beds
- 2 Baths
- 1,173 Sq Ft
- Built 2003
Last Sold Summary
- $200/SF
- 14 Days On Market
Current Estimated Value $236,338

Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne

164 Brookland Ct Unit 10, Winchester, VA 22602

/49
Est $484,508 Not Listed For Sale

401 Briarmont Dr, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 2,504 Sq Ft
- Built 1963
401 Briarmont Dr, Winchester, VA 22601

Last Sold Summary
- 4% Above List Price
- $186/SF
- 2 Days On Market
Last Sold Price $465,000

Last Listing Agent Dallas Croft Samson Properties

/29
$255,000 Pending
- 1 Bed
- 1 Bath
- 660 Sq Ft
1208 Rockwood Trail, Winchester, VA 22602

* All offers must be made by 2/21 by 430pm. * Escape to your private mountain retreat in the heart of the Shenandoah Valley. This 1-bedroom, 1-bath cabin sits atop the mountain just minutes from Winchester, offering panoramic views, crisp Blue Ridge air, and some of the darkest skies in the region—perfect for stargazing.Enjoy easy access to hiking, wildlife, and scenic beauty throughout the

Kimberly Schroeder

Long & Foster Real Estate, Inc.

(540) 269-5294

1208 Rockwood Trail, Winchester, VA 22602
/41
$2,395 per month
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
- Townhouse for Rent
3141 Eton Place, Winchester, VA 22601

NEWER END UNIT, 2-CAR GARAGE LUXURY TOWNHOUSE! 3 BR 2.5 BA w/ over 2,100 sq ft and 9-ft ceilings on three levels with HIGH end finishes throughout and a 4 foot extension on all levels! The main level features a center gourmet kitchen with upgraded cabinets, stainless steel appliances, quartz countertops, oversized island, luxury vinyl plank flooring and upgrades throughout. Kitchen opens to a

Susie Kontzias Suburban Homes Realty, Inc.

3141 Eton Place, Winchester, VA 22601
/33
$421,000 Sold Mar 07, 2025

716 Frederick Ave, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 1,732 Sq Ft
- Built 1941
Last Sold Summary
- $243/SF
- 3 Days On Market
Current Estimated Value $434,497

Last Listing Agent Lori Bales Keller Williams Realty

716 Frederick Ave, Winchester, VA 22601

/47
Est $576,428 Not Listed For Sale

412 W Cecil St, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 2,196 Sq Ft
- Built 1945
412 W Cecil St, Winchester, VA 22601

Last Sold Summary
- 3% Above List Price
- $255/SF
- 3 Days On Market
Last Sold Price $560,000

Last Listing Agent Jeanne Mezzatesta Colony Realty

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