Winchester County, VA Homes

/51
$499,900
- 3 Beds
- 3 Baths
- 1,564 Sq Ft
510 S Cameron St, Winchester, VA 22601

Step into a piece of Winchester history, thoughtfully restored and completely renovated in 2025 while preserving the character and craftsmanship that make this historic home so special.Originally built in 1865, this downtown Winchester property has been extensively updated from top to bottom, blending modern comfort with carefully preserved historic details. The kitchen was returned to

Brock Harris

Samson Properties

510 S Cameron St, Winchester, VA 22601
/50
Starting at $1,700 Plus Fees
- 1 - 2 Beds
2351 Quinn Ct, Winchester, VA 22601

This new mixed-use community is centrally located in Winchester with quick access to Routes 522 and I-81. Designed for modern, convenient living, Carl's Corner features three residential buildings and a standalone commercial complex.The community offers 18 one-bedroom and 60 two-bedroom apartments, all within walking distance of shopping centers and just minutes from restaurants and

CARLS CORNER RESIDENTIAL

2351 Quinn Ct, Winchester, VA 22601
/37
$420,000

Sold Jun 30, 2026

17 E Leicester St, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 2,100 Sq Ft
- Built 1928
Last Sold Summary
- $200/SF
- 196 Days On Market
Current Estimated Value $411,410

Last Listing Agent Roger Lamborne MarketPlace REALTY

17 E Leicester St, Winchester, VA 22601

/2
Est $288,643

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
- 3 Days On Market
Last Listing Agent Ned Stock Berkshire Hathaway HomeServices PenFed Realty

/22
$949,000

New Construction Under Contract
- 4 Beds
- 3.5 Baths
- 2,546 Sq Ft
0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602

TO BE BUILT: Fauver and Browning Homes proudly presents The Tremont House—a masterfully designed modern residence that blurs the line between architecture and nature. Thoughtfully crafted to harmonize with its surroundings, this home offers a calm, refined living experience. Tucked at the end of a private cul-de-sac in desirable Fairway Estates, overlooking Winchester Country Club, the design

Jeanne Mezzatesta

Colony Realty

0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602
/22
$1,800 Per Month
- 3 Beds
- 1.5 Baths
- 1,260 Sq Ft
- Townhouse for Rent
314 E Piccadilly St, Winchester, VA 22601

Freshly updated and just two blocks from the Old Town Pedestrian Mall — this charming downtown duplex is the perfect blend of historic character and modern comfort. Recently renovated, this 3-bedroom, 1.5-bath home features gleaming hardwood floors, beautifully updated tile bathrooms, stainless steel appliances, abundant natural light, and timeless architectural details throughout.Enjoy

Jeanne Mezzatesta

Colony Realty

314 E Piccadilly St, 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 $294,882

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

209 S Braddock St, Winchester, VA 22601

/19
Est $436,128

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
- 49 Days On Market
Last Listing Agent Jason Aikens RE/MAX Roots

/40
$370,000
- 4 Beds
- 1.5 Baths
- 1,588 Sq Ft
1008 S Cameron St, Winchester, VA 22601

Live just minutes from historic Old Town Winchester, where charming boutiques, local restaurants, and picturesque streets are all close at hand. This beautifully maintained two-story home seamlessly blends the timeless character of the 1930s with the modern updates today’s buyers appreciate.A classic covered front porch welcomes you home and offers the perfect place to enjoy your morning

Nikola Tadie Redfin Corporation

1008 S Cameron St, Winchester, VA 22601
/22
Starting at $1,495

Total Monthly Price
- 2 - 4 Beds
2260 Wilson Blvd, Winchester, VA 22601

Discover the perfect blend of comfort and convenience at Blue Ridge Apartments in Winchester, VA. Our recently updated homes feature a variety of floor plans. Nestled in a pet-friendly community, you're just minutes away from Winchester's scenic spots, historic downtown, Apple Blossom Mall, and major employers. With easy access to I-81 and Route 7, the best of Winchester is always within reach.

Blue Ridge Apartments

2260 Wilson Blvd, Winchester, VA 22601
/47
$335,000

Sold Jul 28, 2026

517 Dunlap St, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 1,366 Sq Ft
- Built 1941
Last Sold Summary
- 9% Below List Price
- $245/SF
- 45 Days On Market
Current Estimated Value $336,466

Last Listing Agent Carolyn Young Samson Properties

517 Dunlap St, Winchester, VA 22601

/37
Not Listed For Sale

216 E Piccadilly St, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 2,052 Sq Ft
- Built 2022
216 E Piccadilly St, Winchester, VA 22601

Last Sold Summary
- 651 Days On Market
Last Listing Agent Jason Aikens RE/MAX Roots

/19
$329,990

New Construction
- 3 Beds
- 2.5 Baths
- 1,576 Sq Ft
Juniper Plan at Old Town Green, Winchester, VA 22601

Welcome to Ryan Homes at Old Town Green, experience life in Old Town Winchester with the city's lowest priced garage townhomes, just a short walk to shops, dining and recreation.The Juniper townhome combines all the amenities of single-family living with total convenience. The main level is highlighted by a gourmet kitchen that's open to the living area so you'll never miss a moment. The

Ryan Homes Builder

306 Smalts Cir Unit 41303475, Winchester, VA 22601
/10
$1,700 Per Month
- 1 Bed
- 1 Bath
- 9,518 Sq Ft
- Condo for Rent
44 S Loudoun St Unit 12, Winchester, VA 22601

Charming one-bedroom apartment in the heart of historic downtown Winchester! Located right on the Walking Mall, you’ll be surrounded by local shops, restaurants, and entertainment. This inviting apartment features a spacious living room, an updated kitchen with newer cabinets and stainless steel appliances, convenient in-unit laundry, and one assigned parking space in a private lot. Enjoy

Brock Harris

Samson Properties

44 S Loudoun St Unit 12, Winchester, VA 22601
/47
$512,000

Sold Feb 27, 2026

216 Fairmont Ave, Winchester, VA 22601
- 3 Beds
- 1.5 Baths
- 2,177 Sq Ft
- Built 1911
Last Sold Summary
- $235/SF
- 81 Days On Market
Current Estimated Value $545,213

Last Listing Agent Dave Spence RE/MAX Roots

216 Fairmont Ave, Winchester, VA 22601

/5
Not Listed For Sale

378 National Ave, Winchester, VA 22601
- Studio
- 3,032 Sq Ft
- Built 1910
378 National Ave, Winchester, VA 22601

Last Sold Summary
- 17 Days On Market
Last Listing Agent Bill Nordman Commercial Specialists

/23
$127,750
- Land
- 8.11 Acres
- $15,752 per Acre
0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602

Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by, making for easy

Chad Pangle Whitetail Properties Real Estate

0 Wolf Spring Trail Unit LotWP001, Winchester, VA 22602
/17
Starting at $500 Plus Fees
- 1 - 2 Beds
548 Brookfield Dr, Winchester, VA 22601

We are excited to share that we are under new ownership and management, and we're eager to welcome new guests to our community.Located at 500 Brookfield Drive, Winchester, VA 22601, Brookfield Corporate Apartments offers spacious, fully furnished one and two-bedroom apartments. Each apartment is designed with your comfort in mind and comes equipped with linens, kitchenware, two TVs with

Brookfield Extended Stay Apartments

548 Brookfield Dr, Winchester, VA 22601
/13
$325,000

Sold Aug 25, 2026

632 Watson Ave, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 1,465 Sq Ft
- Built 1940
Last Sold Summary
- $222/SF
- 51 Days On Market
Current Estimated Value $314,565

Last Listing Agent Jennifer Sacco RE/MAX Roots

632 Watson Ave, Winchester, VA 22601

/37
Est $404,697

Not Listed For Sale

204 E Piccadilly St, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 2,052 Sq Ft
- Built 2022
204 E Piccadilly St, Winchester, VA 22601

Last Sold Summary
- 741 Days On Market
Last Listing Agent Jason Aikens RE/MAX Roots

/29
$369,999
- 3 Beds
- 2 Baths
- 1,387 Sq Ft
2919 S Pleasant Valley Rd, Winchester, VA 22601

Home Warranty for the Buyer + Bonus for the Buyer’s Agent with a Ratified Contract in September! Welcome to this adorable and beautifully refreshed Cape Cod, ideally located on a quiet street in Winchester City with no HOA! This move-in-ready home offers a comfortable and versatile floor plan, featuring a primary suite on the main level, plus two spacious bedrooms and a second full bathroom

Patricia Rivas Plata Keller Williams Realty Dulles

2919 S Pleasant Valley Rd, Winchester, VA 22601
/7
$1,800 Per Month
- 1 Bed
- 1 Bath
- 2,124 Sq Ft
- Condo for Rent
619 S Cameron St Unit 2, Winchester, VA 22601

Charming apartment located in 2 family unit, walking distance to Old Town Winchester. Original hardwood floors, light and bright unit with washer and dryer in unit. Landlord pays water and sewer and tenant pays electric. Shared yard.

Brock Harris

Samson Properties

619 S Cameron St Unit 2, Winchester, VA 22601
/29
$374,990

Sold Jun 02, 2026

221 Monteith Dr, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 1,784 Sq Ft
- Built 2026
Move in Ready Sold Summary
- 9% Below List Price
- $210/SF
- 87 Days On Market
DRB Homes Village at Valor Crossing - Townhomes

221 Monteith Dr, Winchester, VA 22601

/14
Not Listed For Sale

611 Laurelwood Cir, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,442 Sq Ft
611 Laurelwood Cir, Winchester, VA 22601

Last Sold Summary
- 28 Days On Market

/22
$269,000
- Land
- 42,253 Sq Ft
- $277,320 per Acre
823 Armistead St, Winchester, VA 22601

*** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plandesigned by Seller customized for this lot and optimized for cost effective construction. Closingon the lot may occur upon issuance of the Building Permit in Buyer’s name by the City ofWinchester. ***This modern farmhouse style home includes 5,630 square feet of living space

Janet Flaherty Keller Williams Realty

823 Armistead St, Winchester, VA 22601
/16
$1,500 Per Month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
115 S Loudoun St Unit 1, Winchester, VA 22601

1 Bedroom/1 Bath. 2nd Floor apartment. Newly remodeled. Great location. Downtown Winchester Walking Mall. Baseboard heat. Window cooling unit. Stackable washer and dryer in unit. Laminate flooring. No pets. No smoking. Rent includes water/sewer and trash.

115 S Loudoun St Unit 1, Winchester, VA 22601
/43
$410,000

Sold Apr 20, 2026

1332 Ramseur Ln, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 2,648 Sq Ft
- Built 1994
Last Sold Summary
- 4% Below List Price
- $155/SF
- 16 Days On Market
Current Estimated Value $432,251

Last Listing Agent James King RE/MAX Roots

1332 Ramseur Ln, Winchester, VA 22601

/14
Not Listed For Sale

629 Laurelwood Cir, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,442 Sq Ft
629 Laurelwood Cir, Winchester, VA 22601

Last Sold Summary
- 8 Days On Market

/33
$447,000

$3K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,540 Sq Ft
310 Longview Ave, Winchester, VA 22601

Discover a stunning blend of Colonial and Contemporary architecture in this exquisite 3-bedroom, 2.5-bathroom residence, built in 2024. Step inside to find luxurious vinyl plank flooring and plush carpeting that exude warmth and sophistication. The gourmet kitchen is a chef's dream, equipped with high-end appliances including a sleek wall oven, cooktop, and energy-efficient refrigerator, ensuring

Dave Milburn Coldwell Banker Realty

310 Longview Ave, Winchester, VA 22601
/8
$1,450 Per Month
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
- Townhouse for Rent
2256 Roosevelt Blvd, Winchester, VA 22601

Very spacious 2-bedroom, 1-bathroom townhouse offering comfortable living in a well-maintained setting. Features include a rear entrance leading to a private porch area and convenient parking. Shared laundry facilities are located within the complex. Ideally situated near shopping, restaurants, and Shenandoah University. Tenant pays all utilities. No smoking, no pets, and no vaping permitted.

Frank Armstrong, IV

Colony Realty

2256 Roosevelt Blvd, Winchester, VA 22601
/56
$425,000

Sold Jun 15, 2026

743 Berryville Ave, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 1,400 Sq Ft
- Built 1934
Last Sold Summary
- 3% Below List Price
- $304/SF
- 56 Days On Market
Current Estimated Value $417,010

Last Listing Agent Sineenat Sirimas Pearson Smith Realty, LLC

743 Berryville Ave, Winchester, VA 22601

/10
Not Listed For Sale

0 Oak Ridge Ln Unit VAFV2035504, Winchester, VA 22602
0 Oak Ridge Ln Unit VAFV2035504, Winchester, VA 22602

Last Sold Summary
- 15 Days On Market
Last Listing Agent Sarah Abderrazzaq Realty ONE Group Old Towne

/13
$419,000

Under Contract
- 3 Beds
- 3 Baths
- 1,453 Sq Ft
131 Shirley St, Winchester, VA 22601

Back on Market!!!A full bathroom was added to the property and it appraised for $435k when it had 2.5 bathrooms and now it has 3 full bathrooms.This exquisite Cape Cod residence, originally built in 1929 and set to undergo a stunning renovation in 2026, seamlessly blends timeless charm with modern luxury. Nestled in a desirable neighborhood, this home invites you into a warm and

Brandon Pifer Pifer Realty, LLC

131 Shirley St, Winchester, VA 22601
/13
$1,700 Plus Fees
- 2 Beds
- 1 Bath
- 1,200 Sq Ft
- House for Rent
223 Baker St, Winchester, VA 22601

Property Id: 1770094 Available October 1st. This well-maintained 2-bedroom, 1-bath home offers approximately 1,200 sq. ft. of living space plus a spacious upstairs bonus/flex room that works well as a home office, den, additional living area, or other flexible-use space. The home features hardwood flooring and updated LVP, abundant natural light, an updated kitchen with stainless

223 Baker St, Winchester, VA 22601
/60
$529,000

Sold Dec 04, 2025

121 N Washington St, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 3,100 Sq Ft
- Built 1807
Last Sold Summary
- $171/SF
- 69 Days On Market
Current Estimated Value $558,822

Last Listing Agent M. Kelly Walker RE/MAX Roots

121 N Washington St, Winchester, VA 22601

/13
Not Listed For Sale

LOT B 4661 Middle Rd, Winchester, VA 22602
LOT B 4661 Middle Rd, Winchester, VA 22602

Last Sold Summary
- 34 Days On Market
Last Listing Agent Maureen Cunningham Century 21 Redwood Realty

/19
$395,990

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

648 Arden Court is an attractive new 3 level townhome backing to trees with brick 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, grey cabinets, and stainless-steel appliances.

D.R. Horton Builder

648 Arden Ct, Winchester, VA 22601
/40
$1,600 Per Month
- 2 Beds
- 1 Bath
- 1,250 Sq Ft
- Condo for Rent
21 N Braddock St Unit 3, Winchester, VA 22601

Located in Historic Downtown Winchester on North Braddock Street- 1 block west of Walking Mall. Restaurants, shops, transportation all within walking distance.Hardwood floors throughout historic property, large open rooms, 9' ceilings. 1 of 4 units total in building. Second Floor. No Pets/No Smoking. Large Kitchen features Stove, Microwave, Oven, Full size Fridge -AND a large walk-in

21 N Braddock St Unit 3, Winchester, VA 22601
/49
$675,000

Sold Apr 20, 2026

200 & 210 W Fairfax Ln, Winchester, VA 22601
- 5 Beds
- 3.5 Baths
- 3,294 Sq Ft
- Built 1928
Last Sold Summary
- $205/SF
- 3 Days On Market
Last Listing Agent John Schroth Colony Realty

200 & 210 W Fairfax Ln, Winchester, VA 22601

/39
Not Listed For Sale

320 Russellcroft Rd, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,833 Sq Ft
- Built 1964
320 Russellcroft Rd, Winchester, VA 22601

Last Sold Summary
- 3 Days On Market
Last Listing Agent Jeanne Mezzatesta Colony Realty

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