Winchester, VA Homes

/49
$519,900

Pending
- 3 Beds
- 2.5 Baths
- 2,879 Sq Ft
315 Walker St, Winchester, VA 22601

Beautiful brick split-foyer home tucked away on a quiet dead-end street in the desirable Whittier Acres community. This location is one of Winchester’s best kept secrets! 315 Walker St has nearly 2,900 finished square feet, combining space, flexibility, and a peaceful setting just minutes from Old Town Winchester, Winchester Medical Center, and everyday conveniences. The main level features a

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 698-3569

315 Walker St, Winchester, VA 22601
/17
$1,975

Total Monthly Price
- 3 Beds
- 3.5 Baths
- 1,900 Sq Ft
- Townhouse for Rent
200 Tudor Dr, Winchester, VA 22603

Gorgeous 2/3 bedroom, 3 1/2 bath beautiful town home and quiet TUDOR SQUARE TOWNHOUSES. Brand-new kitchen with walnut cabinets and granite countertops. Finished walkout basement with a full bath and plenty of closet space conserve as third bedroom or game room suite. Walk in closets. Brand-new paint job. Very private End unit. Wood floors on the main level. Washer and dryer in laundry room.

200 Tudor Dr, Winchester, VA 22603
/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 $337,702

Last Listing Agent MJ Frazier Serhant

128 Fox Dr, Winchester, VA 22601

/43
Est $638,614

Not Listed For Sale

405 Lynnehaven Dr, Winchester, VA 22602
- 4 Beds
- 3.5 Baths
- 3,729 Sq Ft
- Built 2012
405 Lynnehaven Dr, Winchester, VA 22602

Last Sold Summary
- 183 Days On Market

/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
/12
$1,350 Per Month
- 2 Beds
- 1 Bath
- 720 Sq Ft
- Townhouse for Rent
233 Kern St, Winchester, VA 22601

Downtown Winchester location, full of light and super cute! This 2 bed/1 bath duplex offers a private, fenced in backyard on the north side of town. Completely renovated in 2022. Available for immediate occupancy. Application fee $50 for everyone 18 or older, no pets, monthly income minimum of 3x the monthly rent, security deposit is $1350, no previous evictions, credit score 620+, no

Anna Fox

NextHome Realty Select

(540) 299-2935

233 Kern St, Winchester, VA 22601
/40
$520,000

Sold Jul 30, 2025

116 Lenore Ln, Winchester, VA 22602
- 5 Beds
- 3 Baths
- 2,489 Sq Ft
- Built 2022
Last Sold Summary
- $209/SF
- 34 Days On Market
Current Estimated Value $543,427

Last Listing Agent Christian Davis EXP Realty, LLC

116 Lenore Ln, Winchester, VA 22602

/60
Est $417,697

Not Listed For Sale

152 Solara Dr, Winchester, VA 22602
- 4 Beds
- 3.5 Baths
- 2,300 Sq Ft
- Built 2017
152 Solara Dr, Winchester, VA 22602

Last Sold Summary
- 0 Days On Market

/27
$359,900

Open Sat 1PM - 3PM Coming Soon
- 3 Beds
- 2 Baths
- 1,743 Sq Ft
601 Gray Ave, Winchester, VA 22601

Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a

Walther Vasquez Johnson

Samson Properties

(540) 701-0507

601 Gray Ave, Winchester, VA 22601
/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 Corporate Apartments

(540) 546-5968

548 Brookfield Dr, Winchester, VA 22601
/25
$215,000

Sold May 15, 2026

212 Shawnee Ave, Winchester, VA 22601
- 3 Beds
- 1 Bath
- 985 Sq Ft
- Built 1966
Last Sold Summary
- 14% Below List Price
- $218/SF
- 4 Days On Market
Current Estimated Value $296,548

Last Listing Agent Alexander Bracke Real Broker, LLC

212 Shawnee Ave, Winchester, VA 22601

/34
Est $284,367

Not Listed For Sale

201 Fawn Dr, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 1,104 Sq Ft
- Built 2014
201 Fawn Dr, Winchester, VA 22602

Last Sold Summary
- 43 Days On Market

/14
$125,000

Pending
- Land
- 2.14 Acres
- $58,411 per Acre
TBD Golds Hill Rd, Winchester, VA 22603

Beautiful 2.14 acre parcel in a prime location just 1⁄2 mile off Route 522 and less than 10 minutes from downtown Winchester! Enjoy the perfect balance of privacy and convenience, tucked behind an existing farm for a peaceful, secluded setting. This property offers mountain and pastoral views, creating a scenic backdrop for your future home. Approved for a 4-bedroom conventional septic system,

Bradley Comstock

ERA Oakcrest Realty, Inc.

(540) 583-3522

TBD Golds Hill Rd, Winchester, VA 22603
/8
$1,600 Per Month
- 2 Beds
- 2 Baths
- 10,400 Sq Ft
- Condo for Rent
23 Taft Ave Unit 3, Winchester, VA 22601

One of the largest 2-bedroom, 2-bathroom apartments in Winchester! This spacious second-floor unit offers comfortable living in a convenient location close to shopping, restaurants, and Shenandoah University. The apartment features central air, a full-size washer and dryer, and a generous layout with plenty of living space. Step outside to enjoy a private porch, perfect for relaxing, sitting, or

Frank Armstrong, IV

Colony Realty

(540) 329-2681

23 Taft Ave Unit 3, Winchester, VA 22601
/74
$340,000

Sold May 15, 2026

707 E Cork St, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,680 Sq Ft
- Built 1931
Last Sold Summary
- 7% Below List Price
- $202/SF
- 6 Days On Market
Current Estimated Value $361,812

Last Listing Agent Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

707 E Cork St, Winchester, VA 22601

/141
Est $1,737,269

Not Listed For Sale

210 Rubinette Way, Winchester, VA 22602
- 4 Beds
- 5.5 Baths
- 7,773 Sq Ft
- Built 2004
210 Rubinette Way, Winchester, VA 22602

Last Sold Summary
- 92 Days On Market

/10
$61,900
- Land
- 30,056 Sq Ft
- $89,710 per Acre
Lots 4 & 5 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) 402-9785

Lots 4 & 5 Glen Ridge Rd, Winchester, VA 22602
/20
Starting at $1,685 Plus Fees
- 2 - 3 Beds
2250 Sofia Way, Winchester, VA 22601

Cedar Hill Apartments offers well-appointed accommodations located in a convenient and relaxing environment. Only minutes away from Route 37, Route 11, and Jubal Early Drive, Cedar Hill apartments offers its tenants easy access to the Winchester Medical Center, Shenandoah University, loads of shopping and restaurants. Interior features include vaulted ceilings, gas fireplace, wood vanity

CEDAR HILL APARTMENTS

(540) 502-3991

2250 Sofia Way, Winchester, VA 22601
/24
$327,000

Sold Aug 15, 2025

827 Panther Dr, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 1,217 Sq Ft
- Built 2025
Last Sold Summary
- $269/SF
- 48 Days On Market
Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

827 Panther Dr, Winchester, VA 22602

/83
Est $910,630

Not Listed For Sale

420 N Hayfield Rd, Winchester, VA 22603
- 4 Beds
- 5 Baths
- 4,632 Sq Ft
- Built 1985
420 N Hayfield Rd, Winchester, VA 22603

Last Sold Summary
- 21 Days On Market

/74
$659,900

$9K PRICE DROP
- 4 Beds
- 3.5 Baths
- 4,429 Sq Ft
119 Thompson Ct, Winchester, VA 22602

Welcome to your dream home in the highly sought-after Twin Lakes Overlook community! This stunning 4-bedroom, 3.5-bathroom brick-front colonial offers nearly 4,200 square feet of meticulously designed, finished living space across three expansive levels. The main level welcomes you with sophisticated finishes, including a dedicated study with custom built-in cabinetry and a formal dining room

Jodi Cilley

Realty ONE Group Old Towne

(540) 730-1462

119 Thompson Ct, Winchester, VA 22602
/22
$1,900 Per Month
- 2 Beds
- 1.5 Baths
- 1,024 Sq Ft
- Townhouse for Rent
2662 Limestone Ct, Winchester, VA 22601

Adorable 2 bed, 1.5 bath end unit townhome with unfinished basement, conveniently located in Winchester City ready for move-in August 1. This unit features a private back deck, fenced backyard, charming feature wall in the front bedroom, pantry, central heat & air & the HOA mows! Tenant will pay for utilities, pets considered on a case-by-case basis with applicable fees, no smoking/vaping. Unit

Anna Fox

NextHome Realty Select

(540) 609-2810

2662 Limestone Ct, Winchester, VA 22601
/61
$935,000

Sold Apr 23, 2026

1112 Stony Hill Rd, Winchester, VA 22603
- 3 Beds
- 1.5 Baths
- 1,204 Sq Ft
- Built 1968
Last Sold Summary
- 1% Above List Price
- $777/SF
- 4 Days On Market
Current Estimated Value $766,719

Last Listing Agent Jennifer Watt Century 21 Redwood Realty

1112 Stony Hill Rd, Winchester, VA 22603

/3
Est $264,333

Not Listed For Sale

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

Last Sold Summary
- 1,469 Days On Market

/66
$450,000

Pending
- 3 Beds
- 3 Baths
- 2,530 Sq Ft
229 Garber Ln, Winchester, VA 22602

Welcome to 229 Garber Lane — Where Historic Charm Meets Prime Commercial Opportunity. Classic charm resides in this uniquely positioned B-2 commercially zoned property offering exceptional flexibility for renovation, redevelopment, or continued residential use. Situated on 1.65± prime acres, this property is surrounded by other B-2 zoned parcels and boasts outstanding visibility from I-81, making

Jodi Cilley

Realty ONE Group Old Towne

(540) 515-4991

229 Garber Ln, Winchester, VA 22602
/20
Starting at $1,500 Plus Fees
- 1 - 3 Beds
221 Peppertree Ln, Winchester, VA 22601

Tastefully designed 1, 2 and 3 bedroom floor plans and richly landscaped surroundings make for a welcome sight to call your home. Located in the heart of Winchester, Peppertree offers the conveniences of city living in a park-like setting. Peppertree is in close proximity to shopping, restaurants, schools and Winchester Medical Center.

Peppertree VA

(540) 502-4841

221 Peppertree Ln, Winchester, VA 22601
/66
$601,000

Sold Sep 30, 2025

140 Kinross Dr, Winchester, VA 22602
- 4 Beds
- 2.5 Baths
- 2,926 Sq Ft
- Built 2004
Last Sold Summary
- $205/SF
- 2 Days On Market
Current Estimated Value $614,432

Last Listing Agent Dallas Croft Samson Properties

140 Kinross Dr, Winchester, VA 22602

/43
Est $400,369

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 Days On Market

/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
/24
$2,225 Per Month
- 3 Beds
- 1.5 Baths
- 1,260 Sq Ft
- Townhouse for Rent
312 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 relaxing

Jeanne Mezzatesta

Colony Realty

(540) 516-3301

312 E Piccadilly St, Winchester, VA 22601
/29
$369,990

Sold Apr 28, 2026

213 Monteith Dr, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 1,784 Sq Ft
- Built 2026
Move in Ready Sold Summary
- 3% Below List Price
- $207/SF
- 40 Days On Market
DRB Homes Village at Valor Crossing - Townhomes

213 Monteith Dr, Winchester, VA 22601

/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
- 42 Days On Market

/32
$449,000
- 4 Beds
- 4.5 Baths
- 1,913 Sq Ft
315 National Ave, Winchester, VA 22601

Fully reimagined for modern living while preserving its timeless charm, this stunning 1910 home in the heart of Downtown Winchester offers the perfect blend of character, luxury, and value. Completely renovated from top to bottom, every detail has been thoughtfully updated—delivering the feel of new construction within a classic architectural setting.This spacious residence features 4

Carlos Soares

Samson Properties

(540) 787-2197

315 National Ave, Winchester, VA 22601
/20
Starting at $1,440 Plus Fees
- 2 - 3 Beds
660 Pemberton Dr, Winchester, VA 22601

Pemberton Village Apartments in Winchester VA is located in the prestigious Meadow Branch subdivision near the intersection of Jubal Early Drive and Harvest Drive. It is a ten building, 120 unit community easily assessable from Interstate 81 or Route 37. Conveniently located near the Apple Blossom Mall, fitness centers, John Handley High School, and Valley Health Medical Center; Pemberton Village

PEMBERTON

(540) 502-4138

660 Pemberton Dr, Winchester, VA 22601
/25
$359,990

Sold Feb 17, 2026

230 Monteith Dr, Winchester, VA 22601
- 3 Beds
- 3.5 Baths
- 1,784 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $202/SF
- 86 Days On Market
DRB Homes Village at Valor Crossing - Townhomes

230 Monteith Dr, Winchester, VA 22601

/41
Est $409,294

Not Listed For Sale

160 Solara Dr, Winchester, VA 22602
- 3 Beds
- 3.5 Baths
- 2,281 Sq Ft
- Built 2017
160 Solara Dr, Winchester, VA 22602

Last Sold Summary
- 6 Days On Market

/30
$325,000

Open Sat 10AM - 12PM Coming Soon
- 4 Beds
- 2 Baths
- 1,273 Sq Ft
629 National Ave, Winchester, VA 22601

Beautifully charming and completely move-in ready, this updated 4-bedroom, 2-bath home offers the perfect blend of style, comfort, and functionality. Step inside to find updated flooring and an open-concept main living area designed for today's lifestyle. The heart of the home is the stunning kitchen, featuring granite countertops, white cabinetry, updated fixtures, and a spacious center island

Walther Vasquez Johnson

Samson Properties

(540) 889-0898

629 National Ave, 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 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. A dedicated dining room

Jeanne Mezzatesta

Colony Realty

(540) 251-7132

6 E Cecil St, 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
Current Estimated Value $574,203

Last Listing Agent Dan Whitacre Colony Realty

553 Bellview Ave, Winchester, VA 22601

/49
Est $422,610

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
- 30 Days On Market

Showing Results 81 - 120, Page 3 of 18

Virginia Winchester County Winchester

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Winchester, VA Homes

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