Winchester, VA Homes

/79
$494,000 Sold Jun 20, 2025
- 2,480 Sq Ft
- $199/SF
- 23 Days On Market
- 3 Beds
- 4 Baths
- Built 1947
610 S Hayfield Rd, Winchester, VA 22602

''PRICE REDUCED $20K '' DON'T MISS OUT ON THIS NEWLY RENOVATED COUNTRY HOME THAT SIT ON 2.14 ACRE WITH 3 BEDROOM 4 BATH, TRI-LEVEL HOME. WALK-IN TO THE OVERSIZED FAMILY ROOM AND COZY UP AND FEEL THE HEAT FROM THE STONEWALL WOOD STOVE. GENEROUS SIZE SUNROOM WITH AN ELECTRIC FIREPLACE & A POWDER ROOM COMPLETE THIS LEVEL. UP TO THE BRAND-NEW GOURMET KITCHEN WITH GRANITE COUNTER TOPS & STAINLESS

Richard Kozlowski Long & Foster Real Estate, Inc.

610 S Hayfield Rd, Winchester, VA 22602

/51
Est $563,300 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,919 Sq Ft
2628 Windwood Dr, Winchester, VA 22601

2628 Windwood Dr, Winchester, VA 22601

/42
$769,900
- 3 Beds
- 3 Baths
- 2,112 Sq Ft
1049 Laurel Grove Rd, Winchester, VA 22602

Nestled at the end of a peaceful cul-de-sac, this stunning, property offers the perfect blend of seclusion and community living. This custom-designed home offers three bedrooms and three bathrooms, with the convenience of main-level living. Surrounded by lush woodlands and boasting breathtaking views of both trees and mountains, this property is ideal for those seeking a tranquil retreat that

LESLIE WEBB Long & Foster Real Estate, Inc.

1049 Laurel Grove Rd, Winchester, VA 22602
/55
$419,990 Sold Jun 20, 2025
- 1,889 Sq Ft
- $222/SF
- 48 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2025
165 Munsee Cir, Winchester, VA 22602

The Adams townhome design comes complete with 4 bedrooms, 3.5 bathrooms, and a 1 car garage. You will love the granite countertops, stainless steel appliances, and recessed lighting in the kitchen. Create the 4th bedroom of your dreams in the lower level bonus space! Other highlights include: Spacious 9 ft ceilings on the main level, over-sized kitchen island, upgraded cabinets, stainless steel

Tracy Jennings D R Horton Realty of Virginia LLC

165 Munsee Cir, Winchester, VA 22602

/33
Est $504,768 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,976 Sq Ft
621 Bittersweet Ct, Winchester, VA 22601

621 Bittersweet Ct, Winchester, VA 22601

/6
$4,000,000
- Land
- 27 Acres
- $147,059 per Acre
0 N Frederick Pike Unit VAWI2007698, Winchester, VA 22603

Unprecedented Development Opportunity, County of Frederick, 27.2 acres in land use plan for high density rezoning (RP) and development (currently zoned RA, will require rezoning). Ideal townhouse and apartment project. Gateway to downtown Old Town Winchester. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1

Gillian Greenfield Coldwell Banker Premier

0 N Frederick Pike Unit VAWI2007698, Winchester, VA 22603
/30
$350,000 Sold Jun 20, 2025
- 1,105 Sq Ft
- $317/SF
- 27 Days On Market
- 3 Beds
- 1 Bath
- Built 1966
568 Greenwood Rd, Winchester, VA 22602

Welcome to this newly renovated 3-bedroom, 1-bath ranch home on .84 acres located just outside the city of Winchester, VA. Updates include a new roof, windows, water heater, HVAC, composite deck, and upgraded electrical. The updated kitchen includes new quartz countertops, lighting, all new stainless appliances, new tile flooring, and ample cabinet space. Off the kitchen is the dining area and

Jon Fleming Weichert Realtors - Blue Ribbon

568 Greenwood Rd, Winchester, VA 22602

/47
Est $604,641 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,662 Sq Ft
601 Bittersweet Ct, Winchester, VA 22601

601 Bittersweet Ct, Winchester, VA 22601

/6
$4,500,000
- Land
- 11 Acres
- $393,701 per Acre
801 Fairmont Ave, Winchester, VA 22601

Unprecedented Development Opportunity, City of Winchester, 10.34 acres plus 3 SFH fronting Fairmont Ave (additional 1.09 acres). Gateway to downtown Old Town Winchester. Prime location for high density multifamily and mixed use commercial. Public utilities to site. Truly a catalyst development opportunity, located in the fast growing metropolitan area in Virginia. Voted #1 Main Street and Places

Gillian Greenfield Coldwell Banker Premier

801 Fairmont Ave, Winchester, VA 22601
/19
$450,000 Sold Jun 20, 2025
- 1,637 Sq Ft
- $275/SF
- 134 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2025
117 Monacan St, Winchester, VA 22602

The Cabral is a 1,665-square-foot, two-story home with three bedrooms, 2.5 bathrooms, a loft, and a two-car garage. The open-concept main level features a spacious living room, an eat-in kitchen with stainless steel appliances, a walk-in pantry, and a sliding glass door to the backyard. Upstairs, the owner’s suite boasts a large bedroom, walk-in closet, and luxurious bath, complemented by two

Tracy Jennings D R Horton Realty of Virginia LLC

117 Monacan St, Winchester, VA 22602

/58
Est $403,862 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,394 Sq Ft
612 Crestview Terrace, Winchester, VA 22601

612 Crestview Terrace, Winchester, VA 22601

/41
$310,000
- 5 Beds
- 2 Baths
- 1,152 Sq Ft
601 Grove St, Winchester, VA 22601

601 Grove Street, is a single-family home offering a blend of comfort and convenience. Built in 1980, this 1,152 sq ft ranch-style residence features 3 bedrooms and 1 full bath on the main level, complemented by a partially finished basement that includes an additional bathroom and laundry area. The basement also offers versatile spaces that can serve as extra bedrooms, an office, or a recreation

Lilly Triplett Colony Realty

601 Grove St, Winchester, VA 22601
/25
$520,000 Sold Jun 19, 2025
- 2,296 Sq Ft
- $226/SF
- 13 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1963
423 W Monmouth St, Winchester, VA 22601

Welcome to this charming home located in downtown Winchester! Lovingly built and cared for by its original owner for 62 years, this 3-bedroom, 2-bath home is hitting the market for the very first time. While this property is in need of updates, its potential is endless, and is being offered at less than the tax assessment. Situated on a beautiful corner lot, step inside and be greeted by the

Lindsey Richardson ERA Oakcrest Realty, Inc.

423 W Monmouth St, Winchester, VA 22601

/38
Est $627,678 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 4,159 Sq Ft
929 Meadow Ct, Winchester, VA 22601

929 Meadow Ct, Winchester, VA 22601

/72
$699,000
- 4 Beds
- 4.5 Baths
- 4,320 Sq Ft
292 Green Spring Rd, Winchester, VA 22603

Welcome to your dream home! Nestled on just over 5 serene acres, this beautifully maintained 4-bedroom, 4.5-bathroom property offers the perfect blend of comfort, style, and functionality. From the moment you arrive, you’ll be charmed by the picturesque country and mountain views and the orchard-like feel created by numerous fruit trees (peaches, pears, apples, and cherries) lining the front

Katie Landi Jordan Samson Properties

292 Green Spring Rd, Winchester, VA 22603
/33
$799,950 Sold Jun 19, 2025
- 2,650 Sq Ft
- $302/SF
- 21 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2025
2850 Cedar Creek Grade, Winchester, VA 22602

Complete and Ready for New Owners, located on 5 Acres close to Winchester City, Rose Hill Park, The Winchester Medic al Center, Shopping, Marker Miller Orchard, Schools and Historic Downtown Winchester! The Grovemont Floor Plan offers a standard of modern luxury and design. It is a 3-bedroom, Plus a Technology Room/Office, 2.5 Bath home designed to be bright, open, and functional. The interior

LESLIE WEBB Long & Foster Real Estate, Inc.

2850 Cedar Creek Grade, Winchester, VA 22602

/32
Est $479,681 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,332 Sq Ft
2329 Harrison St, Winchester, VA 22601

2329 Harrison St, Winchester, VA 22601

/6
$398,000
- Land
- 0.60 Acre
- $663,333 per Acre
0 Marathon Dr, Winchester, VA 22602

Property Description/Offering: Two parcels .61 and .6 ac to be sold together only. Corner lot with paved streets surrounded by developed parcels just off Valley Pike (Rte 11 South) near DMV. Ground is level and cleared. Fiber-optic cable in ground. Highlights (5):Well-known and easy access off Valley Pike (South) near DMVCorner LotZoned B2 - Business GeneralGround is level and cleared -

Bill Nordman Commercial Specialists

0 Marathon Dr, Winchester, VA 22602
/43
$630,000 Sold Jun 18, 2025
- 1,940 Sq Ft
- $325/SF
- 40 Days On Market
- 3 Beds
- 2 Baths
- Built 1920
4661 Middle Rd, Winchester, VA 22602

Don’t miss a rare opportunity to own this countryside farmette located justfive minutes from downtown Winchester. The completely renovatedfarmhouse shines on 5.9 picturesque acres with sweeping lawns, maturetrees and ample acreage for livestock, gardens and pets. When you stepinside this thoughtfully restored home, you are welcomed by light-filledspaces featuring all-new

Maureen Cunningham Century 21 Redwood Realty

4661 Middle Rd, Winchester, VA 22602

/44
Est $473,750 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,985 Sq Ft
2301 Harrison St, Winchester, VA 22601

2301 Harrison St, Winchester, VA 22601

/81
$689,900
- 4 Beds
- 3.5 Baths
- 4,411 Sq Ft
226 Taggart Dr, Winchester, VA 22602

Welcome to 226 Taggart Drive – a sunlit Colonial in the heart of Winchester's sought-after Raven Pointe community.This spacious 4-bedroom, 3.5 bath home offers over 4,200 square feet of beautifully finished living space across three levels, thoughtfully designed for comfort, functionality, and quiet everyday living. Nestled on a peaceful street just minutes from historic downtown Winchester,

Lilly Triplett Colony Realty

226 Taggart Dr, Winchester, VA 22602
/2
$1,750 Sold Jun 18, 2025
- Land
- 0.25 Acre
- $7,000 per Acre
- 56 Days On Market
614 Opossum Trail, Winchester, VA 22602

Priced to sell. 615 Elk and 614 Opossum are back-to-back and although priced individually, are to be sold together. House numbers are for GPS convenience only. HOA allows stick-built and modular homes, but not camping, or mobile homes. Lots not surveyed and corner markers not there to the best of my knowledge. Each lot is approximately 75 feet wide and 150 feet deep.

David Houghtaling Weichert, REALTORS

614 Opossum Trail, Winchester, VA 22602

/37
Est $298,140 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
2225 Harrison St, Winchester, VA 22601

2225 Harrison St, Winchester, VA 22601

/29
$399,000
- 5 Beds
- 2 Baths
- 2,186 Sq Ft
214 S Braddock St, Winchester, VA 22601

This property is currently zoned as fully commercial but has the potential to be changed to: Mixed Use or Fully Residential with proper city approval. Additional information from city located in documents. This home will need a Kitchen.Situated in Downtown Winchester, 214 S Braddock is waiting for your ideas! Built in 1865, this home features historic charm including exposed brick walls,

Matt Leiva Keller Williams Realty

214 S Braddock St, Winchester, VA 22601
/39
$320,000 Sold Jun 17, 2025
- 1,376 Sq Ft
- $233/SF
- 3 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1960
2938 S Pleasant Valley Rd, Winchester, VA 22601

Welcome to this well-maintained ranch-style home that offers comfort, character, and plenty of room to grow. Built in 1960, this charming 3-bedroom, 1.5-bath property features hardwood floors throughout and a spacious living room complete with a large picture window and a cozy fireplace. Thoughtful built-ins and a dedicated dining area add both charm and functionality.The kitchen is

Danielle Snapp Coldwell Banker Premier

2938 S Pleasant Valley Rd, Winchester, VA 22601

/42
Est $299,313 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,182 Sq Ft
2300 Harrison St, Winchester, VA 22601

2300 Harrison St, Winchester, VA 22601

/35
$665,000
- 3 Beds
- 2.5 Baths
- 1,650 Sq Ft
112 W Germain St, Winchester, VA 22601

100-Year-Old Downtown Winchester Charmer – Brought Back to Life in 2025!This beautifully restored century-old home has been completely reimagined from the ground up, blending timeless character with top-tier modern upgrades. Located in the heart of historic downtown Winchester, this home underwent a full-gut renovation in 2025—everything is new. From the all-new electrical wiring and replaced

Amanda Magana RE/MAX Roots

112 W Germain St, Winchester, VA 22601
/40
$475,000 Sold Jun 17, 2025
- 2,376 Sq Ft
- $200/SF
- 6 Days On Market
- 2 Beds
- 3 Baths
- Built 1989
125 Premier Place, Winchester, VA 22602

Welcome to 125 Premier Place! A beautifully maintained 2 Bedroom/3 Bathroom property located in a prime area of Winchester, VA and could easily be transformed back into a 4 bedroom home. With 2,376 square feet of flexible space and B-2 zoning, this unique opportunity is ideal for both residential or commercial use.Renovated in 2016, Major upgrades included a roof, vinyl siding, HVAC, water

Erin Kavanagh EXP Realty, LLC

125 Premier Place, Winchester, VA 22602

/25
Est $297,909 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,192 Sq Ft
24 Glaize Ave, Winchester, VA 22601

24 Glaize Ave, Winchester, VA 22601

/71
$799,000
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
251 Heather Hill Ln, Winchester, VA 22603

Back on market at NO fault of seller. Have you been looking for peace and serenity, then you've found it. This gorgeous property offers almost 50 acres (there are several different parcels included in this sale. Parcels that are included are: 19-3-7 (house parcel, 5 acres), 19-3-10 (garage, pole barn parcel, 5 acres), 19-3-12 (7.79 acres), 19-A-48 (31.04 acres). The lovely Chalet offers 3

Amber Jenkins Century 21 Redwood Realty

251 Heather Hill Ln, Winchester, VA 22603
/49
$481,000 Sold Jun 17, 2025
- 1,994 Sq Ft
- $241/SF
- 27 Days On Market
- 4 Beds
- 3 Baths
- Built 1973
562 Valley View Dr, Winchester, VA 22603

A rare find in 22603! This property is nestled on a mostly wooded, 3 acre lot, offering a private setting. This is a one owner, one level, solid, brick home with a full walk-out basement. Cozy up to the fireplace or relax in the sunroom and take in the peacefulness and wildlife the forest brings. The main level has mostly hardwood floors, 3 bedrooms and 2 full bathrooms, sunroom and gas fireplace

Cara Wilkins MarketPlace REALTY

562 Valley View Dr, Winchester, VA 22603

/38
Est $303,356 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
20 Glaize Ave, Winchester, VA 22601

20 Glaize Ave, Winchester, VA 22601

/67
$615,000
- Studio
- 4,396 Sq Ft
540 Monticello St, Winchester, VA 22601

Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

Laura King MarketPlace REALTY

540 Monticello St, Winchester, VA 22601
/26
$235,000 Sold Jun 16, 2025
- 1,173 Sq Ft
- $200/SF
- 14 Days On Market
- 2 Beds
- 2 Baths
- Built 2003
164 Brookland Ct Unit 10, Winchester, VA 22602

Fantastic third floor condo available with no footsteps to be heard from above! The living room and dining area feature newer luxury vinal plank flooring, vaulted ceiling with skylights and a gas fireplace. Boasting two generously sized bedrooms and two full bathrooms this is a fantastic opportunity to own a piece of the east side of Winchester. Ideal commuter location near Route 7 and Interstate

Stephanie Ryall Realty ONE Group Old Towne

164 Brookland Ct Unit 10, Winchester, VA 22602

/42
Est $555,663 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,288 Sq Ft
2025 Taylor Grace Ct, Winchester, VA 22601

2025 Taylor Grace Ct, Winchester, VA 22601

/60
$660,000
- 4 Beds
- 2.5 Baths
- 3,165 Sq Ft
109 Aulee Ct, Winchester, VA 22602

If you’re looking for a home that truly checks all the boxes, space, setting, style, and room to grow, this is the one you’ve been waiting for. Perfectly perched on a quiet cul-de-sac in the sought-after Twin Lakes Overlook neighborhood, this Toll Brothers built beauty offers more than curb appeal. It boasts a premium lot backing to the lake, with tranquil views that just might make you forget

Kim Spear Keller Williams Realty

109 Aulee Ct, Winchester, VA 22602
/68
$825,000 Sold Jun 16, 2025
- 4,242 Sq Ft
- $194/SF
- 49 Days On Market
- 5 Beds
- 4 Baths
- Built 1975
501 Princess Ct, Winchester, VA 22601

It's all about spectacular mountain views! Built on one of the highest lots in Winchester by the area's premiere builder, Rhodes Brothers. Wake every morning to the fantastic views from the primary bedroom or enjoy your coffee while gazing at Great North Mountain. But this classic colonial home has a lot more to offer, including remodeled baths and kitchen, comfortable sunroom, five bedrooms, and

John Schroth Colony Realty

501 Princess Ct, Winchester, VA 22601

/46
Est $507,384 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,872 Sq Ft
2012 Taylor Grace Ct, Winchester, VA 22601

2012 Taylor Grace Ct, Winchester, VA 22601

/23
$99,900
- Land
- 16 Acres
- $6,283 per Acre
LOT 11-HOOVER MTN Pack Horse Rd, Winchester, VA 22603

Unique property, great for recreation. Land is all wooded, tall hardwoods, mostly mountainside. There is about 1.5 acres where Little Mountain Run (creek) runs through the property for over 300' so that you have a very flat, wooded area on the other side of the creek which is perfect for hiking, camping, hunting. You will have to visit the property to really appreciate what it has to offer.

Edward Beightol Cedar Creek Real Estate

LOT 11-HOOVER MTN Pack Horse Rd, Winchester, VA 22603
/53
$848,400 Sold Jun 16, 2025
- 4,056 Sq Ft
- $209/SF
- 410 Days On Market
- 5 Beds
- 3 Baths
- Built 2024
279 Fishel Rd, Winchester, VA 22602

10-7-24 Foundation Installed. Getting Ready to Frame! Impressive Home. Very private community (3 lots) can not be seen from road. Close to town with wooded lots setting off of main road with private lane (TO BE PAVED UPON COMPLETION OF HOMES). This home boosts two level living with 3,056 sq. ft. of floor plan with so many features others would call them upgrades! Brick front with cement siding

Jim Thomson Realty ONE Group Old Towne

279 Fishel Rd, Winchester, VA 22602

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