Winchester, VA Homes

/46
$489,000 Under Contract
- 3 Beds
- 1.5 Baths
- 1,698 Sq Ft
312 W Cecil St, Winchester, VA 22601

Don’t miss your chance to live on sought-after W. Cecil in this charming, beautifully maintained historic home, just a few blocks from the walking mall. Light-filled and inviting, this home welcomes you with a classic covered front porch and warm hardwood floors that set the tone for the character throughout. The cozy living room features a recently converted gas fireplace, lovely built-ins, and

Jeanne Mezzatesta

Colony Realty

(540) 405-6463

312 W Cecil St, Winchester, VA 22601
/11
$1,400 per month
- 1 Bed
- 1 Bath
- 700 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
/43
$355,000 Sold Aug 04, 2025

120 Seabreeze Ln, Winchester, VA 22602
- 3 Beds
- 3.5 Baths
- 1,941 Sq Ft
- Built 2003
Last Sold Summary
- $183/SF
- 7 Days On Market
Current Estimated Value $361,206

Last Listing Agent Bill Fritz RE/MAX Executives

120 Seabreeze Ln, Winchester, VA 22602

/3
Est $247,000 Not Listed For Sale

403 Panther Dr, Winchester, VA 22602
403 Panther Dr, Winchester, VA 22602

Last Sold Summary
- 6,075% Above List Price
- 1,469 Days On Market
- Last Sold Price $4,000
- Oct 09, 2023
Last Listing Agent David Houghtaling Weichert Corporate

/30
$285,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
704 Watson Ave, Winchester, VA 22601

Beautifully Maintained Bungalow in a Prime Location! SELLER MOTIVATED! This home offers 2 bedrooms and 1 full bath on the main level, showcasing pride of ownership throughout. Ideally located just blocks from shopping, coffee shops, and all the conveniences the city has to offer, this property combines comfort with unbeatable accessibility. Enjoy a spacious eat-in kitchen with plenty of room for

Carlos Soares

Samson Properties

(540) 530-4023

704 Watson Ave, Winchester, VA 22601
/14
$2,200 per month
- 2 Beds
- 2 Baths
- 1,150 Sq Ft
- Condo for Rent
104 S Loudoun St Unit 2, Winchester, VA 22601

Charming downtown living at it s best! Perfectly located directly on the Historic Downtown Walking Mall. This spacious 2 bedroom 2 bathroom condo features very own washer and dryer, stainless steel appliances, 2 assigned parking spots, HVAC and more. Shops, restaurants, museums, and more only steps from your front door. Check out convenient chic living today!

Brock Harris

Samson Properties

(540) 596-5993

104 S Loudoun St Unit 2, 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 $751,460

Last Listing Agent Kira Grubb Realty ONE Group Old Towne

170 Green Spring Rd, Winchester, VA 22603

/43
Est $391,732 Not Listed For Sale

230 Chestnut St, Winchester, VA 22601
- Studio
- 1,238 Sq Ft
- Built 1951
230 Chestnut St, Winchester, VA 22601

Last Sold Summary
- 4% Below List Price
- $330/SF
- 4 Days On Market
- Last Sold Price $409,000
- Jan 03, 2025
Last Listing Agent Jeff Boppe Long & Foster Real Estate, Inc.

/11
$1,499,000
- Land
- 2.45 Acres
- $611,837 per Acre
821,829,839, and 851 Fox Dr, Winchester, VA 22603

Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

Jim Shebest

Coldwell Banker Realty

(540) 530-3068

821,829,839, and 851 Fox Dr, Winchester, VA 22603
/12
$1,600 per month
- 2 Beds
- 1 Bath
- 1,300 Sq Ft
- House for Rent
228 Opequon Ave, Winchester, VA 22601

coming soon- pictures will be up later today

Frank Armstrong, IV

Colony Realty

(540) 766-5892

228 Opequon Ave, Winchester, VA 22601
/56
$612,225 Sold Mar 25, 2026

119 Hydrangea Way, Winchester, VA 22602
- 4 Beds
- 3 Baths
- 2,865 Sq Ft
- Built 2025
Last Sold Summary
- $214/SF
- 210 Days On Market
Last Listing Agent Brooks Sears D R Horton Realty of Virginia LLC

119 Hydrangea Way, Winchester, VA 22602

/36
Not Listed For Sale

912 S Braddock St, Winchester, VA 22601
- Studio
- 3,790 Sq Ft
- Built 1946
912 S Braddock St, Winchester, VA 22601

Last Sold Summary
- $190/SF
- 42 Days On Market
- Last Sold Price $720,000
- Oct 26, 2023
Last Listing Agent Daniel Langberg Washington International Service Executives, LLC

/38
$349,900 Under Contract
- 3 Beds
- 1.5 Baths
- 1,890 Sq Ft
113 Christopher Dr, Winchester, VA 22601

Meticulously maintained 3 bedroom, 1.5 bath home in a convenient in-town Winchester location! This home shows beautifully and features hardwood floors that add warmth and character throughout the main living areas. Spacious bedrooms and updates made over the years make this home functional and livable, while still providing an opportunity to personalize as desired. The partially finished basement

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 318-0527

113 Christopher Dr, Winchester, VA 22601
/16
$2,400 per month
- 4 Beds
- 3.5 Baths
- 1,960 Sq Ft
- Townhouse for Rent
1801 Harvest Dr, Winchester, VA 22601

Brand new and move-in ready, this attractive three-level end-unit townhome at 1801 Harvest Drive offers modern living in a fantastic Winchester location. Featuring a full brick front and additional sound insulation, this end unit provides both style and comfort. The entry level includes a one-car garage, a private bedroom, and a full bathroom, perfect for guests, a home office, or flexible living

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 619-5461

1801 Harvest Dr, 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 $626,532

Last Listing Agent Lisa Alberti Pearson Smith Realty, LLC

716 S Washington St, Winchester, VA 22601

/49
Est $426,137 Not Listed For Sale

110 W Monmouth St, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,728 Sq Ft
- Built 1900
110 W Monmouth St, Winchester, VA 22601

Last Sold Summary
- 5% Above List Price
- $234/SF
- 30 Days On Market
- Last Sold Price $405,000
- Jun 19, 2023
Last Listing Agent Angela Duncan MarketPlace REALTY

/40
$640,000 Under Contract
- 6 Beds
- 3.5 Baths
- 3,192 Sq Ft
162 Omps Dr, Winchester, VA 22601

This exceptional residence is nestled in a popular neighborhood in Winchester, just moments from Winchester Medical Center. With almost 4,000 square feet of refined living space, this 6-bedroom, 3.5-bath home delivers the scale, comfort, and location today’s discerning buyer expects.Designed for both elegant entertaining and everyday ease, the home features expansive living areas filled with

Kimberly Schroeder

Long & Foster Real Estate, Inc.

(540) 274-1014

162 Omps Dr, Winchester, VA 22601
/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
/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 $651,485

Last Listing Agent Kaitlyn Behr Samson Properties

521 Hidden Valley Ln, Winchester, VA 22603

/75
Est $657,522 Not Listed For Sale

103 Renee Ln, Winchester, VA 22602
- 5 Beds
- 3.5 Baths
- 4,700 Sq Ft
- Built 2010
103 Renee Ln, Winchester, VA 22602

Last Sold Summary
- 4% Below List Price
- $146/SF
- 40 Days On Market
- Last Sold Price $685,000
- Jan 30, 2025
Last Listing Agent Traci Shoberg Samson Properties

/11
$61,900
- Land
- 30,056 Sq Ft
- $89,710 per Acre
Lots 14 & 15 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) 712-6303

Lots 14 & 15 Glen Ridge Rd, Winchester, VA 22602
/74

$1,700 - $3,900 plus fees

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
/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 $637,017

Last Listing Agent Michael Elias Century 21 Redwood Realty

162 Darby Dr, Winchester, VA 22602

/2
Est $253,183 Not Listed For Sale

127 S Euclid Ave, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 1,120 Sq Ft
- Built 1920
127 S Euclid Ave, Winchester, VA 22601

Last Sold Summary
- 33% Above List Price
- $170/SF
- 3 Days On Market
- Last Sold Price $190,000
- Jul 15, 2024
Last Listing Agent Carolina Mosquera Weichert Corporate

/11
$51,900
- Land
- 14,810 Sq Ft
- $152,647 per Acre
Lot 10 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) 732-7734

Lot 10 Glen Ridge Rd, Winchester, VA 22602
/14
$1,500 per month
- 2 Beds
- 1.5 Baths
- 23,305 Sq Ft
- Condo for Rent
443 Millwood Ave Unit 5, Winchester, VA 22601

Clean and updated 2-bedroom, 2-bath apartment ideally located near Shenandoah University and downtown Winchester. Features include a functional floor plan, in-unit washer and dryer, and two full bathrooms for added convenience. One assigned parking space conveys, plus street parking options nearby. Situated above commercial space with close proximity to local restaurants, shops, and major

Rachel Olsen Keller Williams Realty

443 Millwood Ave Unit 5, Winchester, VA 22601
/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 $494,459

Last Listing Agent Gina Chatham Century 21 Redwood Realty

151 Morning Glory Dr, Winchester, VA 22602

/72
Est $970,478 Not Listed For Sale

2101 Cedar Grove Rd, Winchester, VA 22603
- 3 Beds
- 2 Baths
- 2,340 Sq Ft
- Built 1993
2101 Cedar Grove Rd, Winchester, VA 22603

Last Sold Summary
- 3% Below List Price
- $427/SF
- 11 Days On Market
- Last Sold Price $1,000,000
- Jun 03, 2024
Last Listing Agent Anna Bergey Nest Realty Harrisonburg

/32
$389,900
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
151 Mccormick Cir Unit 201, Winchester, VA 22602

Price improvement!! Experience Effortless 55+ Living at Winchester Landing – The Sapphire by Ryan Homes Discover the perfect blend of comfort and convenience in the Sapphire model, a spacious single-level condo offering over 1,500 sq. ft. of thoughtfully designed living space. The open-concept layout seamlessly connects a modern kitchen, large island, and bright great room, creating an inviting

Rhonda Shade

ERA Oakcrest Realty, Inc.

(540) 787-2320

151 Mccormick Cir Unit 201, Winchester, VA 22602
/38

$1,873 - $2,574 plus fees

Denstock Meadow Branch LLC

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 conveniently located adjacent to Winchester Medical Center and 2 miles from Old Town Winchester.

424 Ridgewood Ln, 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

/19
Est $434,950 Not Listed For Sale

204 N Kent St, Winchester, VA 22601
- 2 Beds
- 4 Baths
- 2,052 Sq Ft
- Built 2022
204 N Kent St, Winchester, VA 22601

Last Sold Summary
- 3% Above List Price
- $206/SF
- 49 Days On Market
- Last Sold Price $423,345
- Sep 20, 2023
Last Listing Agent Jason Aikens RE/MAX

/60
$644,900 Under Contract
- 4 Beds
- 3.5 Baths
- 3,490 Sq Ft
128 Poe Dr, Winchester, VA 22602

128 Poe Drive presents one of the largest models offered in the neighborhood, ideally positioned on a desirable corner lot with an expansive side yard in addition to the backyard. Built in 2023 and filled with upgrades, get ready to see one of the best homes in Winchester. Offering over 3,500 square feet with 4 bedrooms plus loft upstairs, including a finished basement, this home provides

MJ Frazier

Serhant

(540) 515-5588

128 Poe Dr, Winchester, VA 22602
/30
$2,400 per month
- 3 Beds
- 3.5 Baths
- 2,228 Sq Ft
- Townhouse for Rent
121 Sequoia Dr, Winchester, VA 22602

This beautifully maintained 3-bedroom, 3.5-bath end unit townhouse offers a perfect blend of comfort and convenience. With an open floor plan, plenty of natural light, and high-end finishes throughout, this home is ideal for modern living. Main Level: Open-concept eat-in kitchen with lots of cabinet space and modern appliances. Spacious family room and convenient half bathroom.Upper Level:

Liz Rutherford ERA Oakcrest Realty, Inc.

121 Sequoia 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 $549,774

Last Listing Agent Mark Francis Real Broker LLC

509 Marion St, Winchester, VA 22601

/45
Est $359,950 Not Listed For Sale

121 W Virginia Pkwy, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,470 Sq Ft
- Built 2017
121 W Virginia Pkwy, Winchester, VA 22601

Last Sold Summary
- $245/SF
- 7 Days On Market
- Last Sold Price $360,000
- Sep 30, 2024
Last Listing Agent Jen Kitner Pearson Smith Realty, LLC

/18
$270,000 Pending
- 2 Beds
- 1.5 Baths
- 1,024 Sq Ft
2640 Limestone Ct, Winchester, VA 22601

Discover this charming Colonial-style townhouse nestled in the desirable Limestone Court community. Built in 1994, this end-unit home offers a perfect blend of comfort and convenience. With 2 spacious bedrooms and 1.5 bathrooms, it's ideal for those seeking a cozy yet functional living space. The brick exterior exudes timeless appeal, while the efficient layout maximizes every square foot. Enjoy

Ned Stock

Berkshire Hathaway HomeServices PenFed Realty

(540) 329-1991

2640 Limestone Ct, Winchester, VA 22601
/46

$1,585 - $2,695 plus fees

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
/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 $243,153

Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne

164 Brookland Ct Unit 10, Winchester, VA 22602

/66
Est $583,058 Not Listed For Sale

3392 Back Mountain Rd, Winchester, VA 22602
- 3 Beds
- 3 Baths
- 2,930 Sq Ft
- Built 1994
3392 Back Mountain Rd, Winchester, VA 22602

Last Sold Summary
- 17% Above List Price
- $171/SF
- 151 Days On Market
- Last Sold Price $500,000
- Nov 08, 2023
Last Listing Agent Alexandra Brown Spring Hill Real Estate, LLC.

Showing Results 41 - 80, Page 2 of 18

Virginia Winchester County Winchester

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