Winchester County, VA Homes

/5
$250,000
- 3 Beds
- 2 Baths
- 1,682 Sq Ft
21 E Germain St, Winchester, VA 22601

Charming 3-Bedroom Home in Historic Winchester, Virginia Discover this beautifully located 3-bedroom, 2-full bath home nestled in the heart of Historic Winchester. This residence boasts an exceptional location, just a short stroll away from the Old Town Mall, allowing you to enjoy local shops and dining. Positioned along the scenic Apple Blossom parade route, this home is perfect for anyone

Corey Morgan

CENTURY 21 Envision

(540) 802-5749

21 E Germain St, Winchester, VA 22601
/34
$2,100 per month
- 2 Beds
- 1.5 Baths
- 1,369 Sq Ft
- Townhouse for Rent
6 E Cecil St, Winchester, VA 22601

Charming Furnished Historic 2-Bedroom Rental Just Two Blocks from the Loudoun Street Walking Mall! Live steps from downtown in this beautifully appointed duplex featuring 2-bedrooms and an additional small office/den upstairs. The home is full of historic character and modern comfort, boasting original hardwood floors, soaring ceilings, and timeless architectural charm throughout. Home can be

Jeanne Mezzatesta

Colony Realty

(540) 269-5654

6 E Cecil St, Winchester, VA 22601
/80
$415,000 Sold May 08, 2025

526 N Braddock St, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,375 Sq Ft
- Built 1927
Last Sold Summary
- $175/SF
- 5 Days On Market
Current Estimated Value $445,664

Last Listing Agent Leah Clowser RE/MAX Roots

526 N Braddock St, Winchester, VA 22601

/37
Est $398,731 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
429 Beechcroft Rd, Winchester, VA 22601

429 Beechcroft Rd, Winchester, VA 22601

/55
$649,000 Under Contract
- 5 Beds
- 2.5 Baths
- 3,420 Sq Ft
501 Jefferson St, Winchester, VA 22601

Welcome Home!If you’ve been searching for an updated home in a PRIME location, this is it! This stunning 5BR/3BA property has been COMPLETELY RENOVATED from top to bottom—and it shows. Step inside to an open floor plan where natural light fills the gorgeous kitchen, featuring quartz countertops, stainless steel appliances, and plenty of space to gather. The adjoining family room opens to a

Jeanne Mezzatesta

Colony Realty

(540) 516-3824

501 Jefferson St, Winchester, VA 22601
/18
$2,050 per month
- 3 Beds
- 1.5 Baths
- 1,344 Sq Ft
- House for Rent
341 Fairview Ave, Winchester, VA 22601

Welcome to this charming single-family home featuring 3 bedrooms and 1.5 baths in a prime Winchester location. The home offers durable LVP flooring throughout and a modern kitchen equipped with stainless steel appliances. Enjoy the convenience of both rear parking and ample street parking. Ideally located with easy access to Routes 7 and 81 and just minutes from downtown Winchester, shopping,

David Peña

Corcoran McEnearney

(540) 253-1608

341 Fairview Ave, Winchester, VA 22601
/73
$1,400,000 Sold Feb 28, 2025

778 Johnston Ct, Winchester, VA 22601
- 6 Beds
- 8 Baths
- 10,500 Sq Ft
- Built 1998
Last Sold Summary
- $133/SF
- 34 Days On Market
Current Estimated Value $1,542,669

Last Listing Agent Carolyn Young Samson Properties

778 Johnston Ct, Winchester, VA 22601

/36
Est $393,933 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,887 Sq Ft
1016 Opequon Ave, Winchester, VA 22601

1016 Opequon Ave, Winchester, VA 22601

/42
$529,000 Pending
- 3 Beds
- 2 Baths
- 1,820 Sq Ft
330 W Cecil St, Winchester, VA 22601

The perfect Downtown Winchester location! Welcome to this charming brick Colonial in the heart of Winchester, within walking distance from the vibrant Old Town shops and restaurants. This home is filled with historic character, featuring hardwood floors, classic built-ins, and beautiful crown molding .The light-filled kitchen has been updated and offers wood cabinetry, stainless steel appliances,

Lori Bales

Keller Williams Realty

(540) 358-8597

330 W Cecil St, Winchester, VA 22601
/8
$1,150 per month
- 1 Bed
- 1 Bath
- 420 Sq Ft
- Condo for Rent
452 N Loudoun St Unit 102, Winchester, VA 22601

452 N Loudoun St Unit 102 is a 1 bed, 1 bath first floor apartment in Downtown Winchester just 4 blocks from the Walking Mall. Limited off street parking is available. The property has central heat and air. One pet is considered on a case-by-case basis. Pet deposit is $300. Monthly pet rent is $50 Landlord pays water, sewer, trash.Qualified tenants will have no previous evictions, no

Anna Fox

NextHome Realty Select

(540) 358-5938

452 N Loudoun St Unit 102, 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 $638,144

Last Listing Agent Lisa Alberti Pearson Smith Realty, LLC

716 S Washington St, Winchester, VA 22601

/62
Est $792,123 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,432 Sq Ft
1500 Brookdale Ct, Winchester, VA 22601

1500 Brookdale Ct, Winchester, VA 22601

/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
$1,700 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
$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
Last Listing Agent Mark Francis Real Broker LLC

509 Marion St, Winchester, VA 22601

/27
Est $362,449 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,575 Sq Ft
958 Kinzel Dr, Winchester, VA 22601

958 Kinzel Dr, Winchester, VA 22601

/12
$549,900 Open Sat 1PM - 3PM
- 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
/7
$1,200 per month
- 2 Beds
- 1 Bath
- 800 Sq Ft
- Condo for Rent
24 W Cecil St, Winchester, VA 22601

Charming Old Town location! Nestled in the heart of historic Old Town, this refreshed two-bedroom apartment offers an ideal urban living experience. The spacious layout is filled with natural light, with large windows creating a bright and airy atmosphere throughout. Conveniently located near shops, dining, and entertainment. Lease Requirements:Good credit and clean background check required.

Frank Armstrong, IV

Colony Realty

(540) 701-4871

24 W Cecil St, 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 $446,260

Last Listing Agent Lori Bales Keller Williams Realty

716 Frederick Ave, Winchester, VA 22601

/38
Est $284,194 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,440 Sq Ft
3 S Euclid Ave, Winchester, VA 22601

3 S Euclid Ave, Winchester, VA 22601

/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
/5
$1,000 per month
- 1 Bed
- 1 Bath
- 800 Sq Ft
- Condo for Rent
318 S Braddock St Unit 3, Winchester, VA 22601

Large 1-bedroom, 1-bathroom apartment located in the heart of Downtown Winchester, just steps from the Old Town Mall. This unit has been newly refreshed and is move-in ready. Convenient walkable location near shopping, dining, and entertainment. Rental Requirements:Tenant must have good credit and pass a clean background check. Restrictions:No smoking. No pets. No vaping.

Frank Armstrong, IV

Colony Realty

(540) 924-1612

318 S Braddock St Unit 3, Winchester, VA 22601
/48
$335,200 Sold Jul 25, 2025

128 Fox Dr, Winchester, VA 22601
- 4 Beds
- 3 Baths
- 2,606 Sq Ft
- Built 1961
Last Sold Summary
- $129/SF
- 25 Days On Market
Current Estimated Value $334,690

Last Listing Agent MJ Frazier Serhant

128 Fox Dr, Winchester, VA 22601

/87
Est $1,513,422 Not Listed For Sale
- 6 Beds
- 5.5 Baths
- 6,474 Sq Ft
407 S Washington St, Winchester, VA 22601

407 S Washington St, Winchester, VA 22601

/23
$320,000
- 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
/8
$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
/61
$580,000 Sold Dec 09, 2025

553 Bellview Ave, Winchester, VA 22601
- 5 Beds
- 2.5 Baths
- 2,386 Sq Ft
- Built 1978
Last Sold Summary
- $243/SF
- 2 Days On Market
Last Listing Agent Dan Whitacre Colony Realty

553 Bellview Ave, Winchester, VA 22601

/55
Est $406,159 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,468 Sq Ft
135 Morningside Dr, Winchester, VA 22601

135 Morningside Dr, Winchester, VA 22601

/36
$365,000 Under Contract
- 4 Beds
- 2 Baths
- 1,780 Sq Ft
127 Shirley St, Winchester, VA 22601

Comfortable living at this split-foyer home located in the heart of the City of Winchester. On the main level, you’ll find three bedrooms and a full bath. The lower level features a fourth bedroom plus a second full bath — ideal for guests, or a home office. Location is a standout. You’re just minutes from downtown dining, shopping, and community events, and enjoy easy access to schools, parks,

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 802-5087

127 Shirley St, Winchester, VA 22601
/11
$2,500 per month
- 2 Beds
- 1 Bath
- 2,500 Sq Ft
- House for Rent
23 S Stewart St, Winchester, VA 22601

About 2500 sqft. of completely updated DOWNSTAIRS apartment space in Downtown Winchester. All newer appliances, repainted, refinished wood floors. Sun Room, Porch, Dining room, Living room. even has some cedar closets! What more could you ask for in the heart of downtown Winchester. Landlord pays water, sewer, and all landscaping. Tenants must have minimum 650 Credit score. NO SMOKING.. NO PETS..

Frank Armstrong, IV

Colony Realty

(540) 698-5153

23 S Stewart St, Winchester, VA 22601
/63
$489,900 Sold Mar 19, 2025

327 Russellcroft Rd, Winchester, VA 22601
- 3 Beds
- 3 Baths
- 3,873 Sq Ft
- Built 1968
Last Sold Summary
- $126/SF
- 5 Days On Market
Last Listing Agent Matt Kilmer Samson Properties

327 Russellcroft Rd, Winchester, VA 22601

/37
Est $479,319 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,052 Sq Ft
222 E Piccadilly St, Winchester, VA 22601

222 E Piccadilly St, Winchester, VA 22601

/41
$345,000
- 3 Beds
- 2 Baths
- 1,066 Sq Ft
105 W Oates Ave, Winchester, VA 22601

This beautifully updated and lovingly maintained home is located in the much loved heart of Winchester. Gleaming hardwood floors welcome you as soon as you enter and that is only the beginning! This sweet home is light filled and happy. Spacious living and dining areas with new recessed lights. The kitchen shines as well with updated lighting, new quartz countertops, sink, coffee bar and

Layne Jensen

CENTURY 21 New Millennium

(540) 781-1560

105 W Oates Ave, Winchester, VA 22601
/7
$1,500 per month
- 2 Beds
- 1 Bath
- 3,150 Sq Ft
- Townhouse for Rent
121 Taft Ave, Winchester, VA 22601

Charming 2-Bedroom Apartment – Prime Location Near Shenandoah University! This well-maintained 1-level apartment features 2 bedrooms and 1 full bathroom. Enjoy the convenience of a great location—just minutes from Shenandoah University, shopping, dining, and more! WASHER and Dryer in the unit!

Frank Armstrong, IV

Colony Realty

(540) 755-3946

121 Taft Ave, Winchester, VA 22601
/73
$497,000 Sold Aug 25, 2025

903 Crestview Terrace, Winchester, VA 22601
- 4 Beds
- 3.5 Baths
- 3,204 Sq Ft
- Built 2006
Last Sold Summary
- $155/SF
- 64 Days On Market
Current Estimated Value $537,697

Last Listing Agent MARIA STRIBLING CENTURY 21 New Millennium

903 Crestview Terrace, Winchester, VA 22601

/20
Est $438,706 Not Listed For Sale
- 2 Beds
- 4 Baths
- 2,160 Sq Ft
206 N Kent St, Winchester, VA 22601

206 N Kent St, Winchester, VA 22601

/25
$359,990 New Construction
- 3 Beds
- 3.5 Baths
- 1,784 Sq Ft
230 Monteith Dr, Winchester, VA 22601

OPEN HOUSE: Saturday - Sunday 1pm - 3pm 3 Level Home with Deck! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. The main level includes a private finished recreation room and possible 4th bedroom with its own

DRB Homes Builder

230 Monteith 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
/23
$270,000 Sold Sep 24, 2025

209 S Braddock St, Winchester, VA 22601
- 2 Beds
- 2 Baths
- 1,446 Sq Ft
- Built 1900
Last Sold Summary
- $187/SF
- 52 Days On Market
Current Estimated Value $281,732

Last Listing Agent Manuela Moyer Long & Foster Real Estate, Inc.

209 S Braddock St, Winchester, VA 22601

/17
Est $290,108 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 734 Sq Ft
228 Weems Ln, Winchester, VA 22601

228 Weems Ln, Winchester, VA 22601

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