Winchester, VA Homes

/7
$200,000
- Land
- 5 Acres
- $40,000 per Acre
Lot A Cather Ln, Winchester, VA 22602

Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

Kaitlyn Behr Samson Properties

Lot A Cather Ln, Winchester, VA 22602
/16
$1,450 Per Month
- 3 Beds
- 1 Bath
- 900 Sq Ft
- Townhouse for Rent
222 E Whitlock Ave, Winchester, VA 22601

Conveniently located near Downtown Winchester, Shenandoah University, shopping, restaurants, and other everyday amenities, this well-maintained 3-bedroom, 1-bath townhome offers comfortable living with plenty of functional space. The main and upper levels feature hardwood flooring, while the eat-in kitchen has durable vinyl flooring. Exceptional closet space throughout the home provides abundant

Meghan Pachas MAP Property Solutions, LLC.

222 E Whitlock Ave, Winchester, VA 22601
/9
$160,000

Sold May 22, 2026

0 Tomahawk Trail Unit VAFV2033070, Winchester, VA 22602
- Land
- 59.93 Acres
- $2,670 per Acre
Last Sold Summary
- 296 Days On Market
Last Listing Agent Wayne Wilson Thomas and Talbot Estate Properties, Inc.

0 Tomahawk Trail Unit VAFV2033070, Winchester, VA 22602

/11
Not Listed For Sale

LOTS 36 & 37 Meadow Way, Winchester, VA 22602
LOTS 36 & 37 Meadow Way, Winchester, VA 22602

Last Sold Summary
Last Listing Agent Bradley Comstock ERA Oakcrest Realty, Inc.

/52
$365,000

Under Contract
- 3 Beds
- 3 Baths
- 2,052 Sq Ft
824 Appleseed Ct, Winchester, VA 22601

Welcome home to this charming 3-bedroom duplex nestled in the highly desirable Orchard Hill neighborhood of Winchester City. Enjoy the convenience of tree-lined sidewalks, street lights, and an easy walk to Park Place Park, making this location perfect for outdoor recreation and neighborhood strolls. Inside, you'll find three finished levels designed for comfortable living. The inviting living

Laura White ERA Oakcrest Realty, Inc.

824 Appleseed Ct, Winchester, VA 22601
/21
$2,195 Per Month
- 4 Beds
- 3.5 Baths
- 1,889 Sq Ft
- Townhouse for Rent
174 Sequoia Dr, Winchester, VA 22602

Vijaya Rallabandi Partners Real Estate

174 Sequoia Dr, Winchester, VA 22602
/36
$525,000

Sold Nov 14, 2025

2723 Windwood Dr, Winchester, VA 22601
- 3 Beds
- 3 Baths
- 2,726 Sq Ft
- Built 1999
Last Sold Summary
- $193/SF
- 38 Days On Market
Current Estimated Value $555,126

Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.

2723 Windwood Dr, Winchester, VA 22601

/35
Not Listed For Sale

620 Cardinal Dr, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 1,217 Sq Ft
- Built 2024
620 Cardinal Dr, Winchester, VA 22602

Last Sold Summary
- 55 Days On Market
Last Listing Agent Sheila Pack RE/MAX Roots

/2
$489,900

New Construction
- 4 Beds
- 2.5 Baths
- 2,300 Sq Ft
181 Manor Dr, Winchester, VA 22602

Welcome to this beautiful new construction home offering over 2300 square feet of living space, This spacious home features 4 bedrooms, 2 1/2 bathrooms, and an attached garage with automatic garage door openers. The main level showcases hardwood flooring throughout, elegant crown molding, and an open inviting layout ideal for everyday living and entertaining. The kitchen is highlighted by granite

Pamela Russell CENTURY 21 New Millennium

181 Manor Dr, Winchester, VA 22602
/10
$2,100 Per Month
- 3 Beds
- 2.5 Baths
- 1,564 Sq Ft
- Townhouse for Rent
2043 Stoneleigh Dr, Winchester, VA 22601

Immaculate and well maintained 3 BR 2.5BA townhome in sought after Orchard Hill community. Conveniently located within city limits. This fabulous end unit townhome offers a spacious floor plan . Upon entering the main level, you step up to an inviting light filled family room that flows into a large kitchen w/ island and dining area. Upper level includes a spacious master bedroom with ensuite

Misty Miller OliveTree Property Group, LLC

2043 Stoneleigh Dr, Winchester, VA 22601
/35
$750,000

Sold Jun 22, 2026

236 Rebecca Dr, Winchester, VA 22602
- 5 Beds
- 3.5 Baths
- 4,010 Sq Ft
- Built 2005
Last Sold Summary
- 3% Above List Price
- $187/SF
- 1 Day On Market
Current Estimated Value $735,698

Last Listing Agent Nadia Sadrzadeh Samson Properties

236 Rebecca Dr, Winchester, VA 22602

/35
Est $593,851

Not Listed For Sale

440 Cattail, Winchester, VA 22603
- 3 Beds
- 2 Baths
- 1,616 Sq Ft
- Built 2013
440 Cattail, Winchester, VA 22603

Last Sold Summary
- 14 Days On Market
Last Listing Agent Katherine (Kat) Wetzel Century 21 Redwood Realty

/73
$439,900
- 3 Beds
- 1.5 Baths
- 2,560 Sq Ft
170 Mountain View Ct, Winchester, VA 22603

Charming 3-bedroom, 1.5-bath colonial home on 5 acres, with an additional 7 acres available. Nestled in nature, it features a detached 2-car garage with power and lights, run-in shed, large gazebo with a chandelier for evening ambiance, and a metal carport for 2 cars. Enjoy the outdoors from the spacious front porch. This home features 4 heat sources so each room will feel comfortable during

Pamela Foltz Realty ONE Group Old Towne

170 Mountain View Ct, Winchester, VA 22603
/44
$3,000 Per Month
- 5 Beds
- 3.5 Baths
- 3,135 Sq Ft
- House for Rent
131 Thornton Way, Winchester, VA 22602

One of the great houses with a great price, don't miss it!Welcome to this beautiful family house in desirable Senseny Village Community! This house condition like new. Built in 2024, this beautiful family house offers five bedrooms and four bathrooms with perfect blend of modern design. Very open space in the front and back of the house, Inside, you'll find a bright, open-concept floor plan

Ram Mishra Spring Hill Real Estate, LLC.

131 Thornton Way, Winchester, VA 22602
/47
$555,000

Sold Dec 22, 2025

2307 Stoneridge Rd, Winchester, VA 22601
- 5 Beds
- 3.5 Baths
- 3,280 Sq Ft
- Built 2016
Last Sold Summary
- $169/SF
- 5 Days On Market
Current Estimated Value $592,540

Last Listing Agent Dave Spence RE/MAX Roots

2307 Stoneridge Rd, Winchester, VA 22601

/15
Not Listed For Sale

3136 Eton Place, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- 1,918 Sq Ft
- Built 2024
3136 Eton Place, Winchester, VA 22601

Last Sold Summary
- 148 Days On Market
Last Listing Agent Brittany Newman DRB Group Realty, LLC

/15
$49,900
- Land
- 3 Acres
- $16,633 per Acre
0 0 Henry Dr, Winchester, VA 22602

"Build Your Home On Henry" This beautiful 3-Acre lot is located in Mountain Falls Park. With mature trees you can enjoy your privacy. Enjoy the community lake, common area, playground and picnic area! Has a 3-bedroom perc. Bring your vision to life!

Matt Kilmer Samson Properties

0 0 Henry Dr, Winchester, VA 22602
/22
$272,000

Sold Mar 20, 2026

105 Parkside Dr, Winchester, VA 22602
- 2 Beds
- 1.5 Baths
- 1,385 Sq Ft
- Built 1989
Last Sold Summary
- 1% Above List Price
- $196/SF
- 4 Days On Market
Current Estimated Value $271,029

Last Listing Agent LESLIE WEBB Long & Foster Real Estate, Inc.

105 Parkside Dr, Winchester, VA 22602

/7
Not Listed For Sale

Lot 12 Mountain Falls Blvd, Winchester, VA 22602
Lot 12 Mountain Falls Blvd, Winchester, VA 22602

Last Sold Summary
- 4 Days On Market
Last Listing Agent Nadeem Helfer Samson Properties

/79
$959,000

New Construction
- 3 Beds
- 2.5 Baths
- 2,000 Sq Ft
0 Light Rd, Winchester, VA 22603

Your Dream Home in the Woods – To Be Built on 20 Unrestricted Acres! Create your own family compound, farm, hobbies, your choice. Imagine coming home to this stunning modern farmhouse nestled on twenty wooded and open acres with pleasant peaceful views. This thoughtfully designed home features spacious living areas, modern finishes, exterior that blends beautifully with its natural surroundings.

Melissa Johnston ERA Oakcrest Realty, Inc.

0 Light Rd, Winchester, VA 22603
/47
$579,990

Sold Apr 30, 2026

123 Wappinger Terrace, Winchester, VA 22602
- 6 Beds
- 4.5 Baths
- 2,632 Sq Ft
- Built 2026
Move in Ready Sold Summary
- 9% Below List Price
- $220/SF
- 38 Days On Market
D.R. Horton Retreat at Winding Creek - Single Family

123 Wappinger Terrace, Winchester, VA 22602

/10
Not Listed For Sale

0 Stagg Trail Unit VAFV2022602, Winchester, VA 22602
0 Stagg Trail Unit VAFV2022602, Winchester, VA 22602

Last Sold Summary
- 123 Days On Market
Last Listing Agent Wendy Conner Coldwell Banker Premier

/45
$375,000
- 3 Beds
- 1 Bath
- 1,225 Sq Ft
1480 Chestnut Grove Rd, Winchester, VA 22603

Enjoy one-level living with 6.44 partly wooded acres. All-brick 3-bedroom, 1-bath home offering a peaceful country setting with plenty of room to enjoy the outdoors. Relax on the covered rear porch overlooking the property. The home features a paved driveway and a full unfinished basement, providing excellent storage or future expansion potential. New water heater installed in 2022, roof

Sheila Pack RE/MAX Roots

1480 Chestnut Grove Rd, Winchester, VA 22603
/18
$454,990

Sold Aug 13, 2025

106 Manasquan Way, Winchester, VA 22602
- 3 Beds
- 2.5 Baths
- 1,665 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $273/SF
- 13 Days On Market
D.R. Horton Retreat at Winding Creek - Single Family

106 Manasquan Way, Winchester, VA 22602

/17
Not Listed For Sale

101 Nootka Way, Winchester, VA 22602
- 3 Beds
- 2.5 Baths
- 1,509 Sq Ft
- Built 2024
101 Nootka Way, Winchester, VA 22602

Last Sold Summary
- 45 Days On Market
Last Listing Agent Tracy Jennings D R Horton Realty of Virginia LLC

/93
$999,990

$250K PRICE DROP Under Contract
- 5 Beds
- 3.5 Baths
- 4,880 Sq Ft
199 Laurel Grove Rd, Winchester, VA 22602

Nestled in the scenic countryside of Winchester, this impressive custom built home offers space, privacy, and beautiful Shenandoah Valley surroundings. Located in Frederick County, the property combines peaceful rural living with convenient access to shopping, dining, and commuter routes.Custom built in 2020, this spacious residence offers approximately 4,800+ square feet of living space on

RoxAnn Grimes RE/MAX Roots

199 Laurel Grove Rd, Winchester, VA 22602
/53
$553,847

Sold Jun 18, 2026

111 Old Wagon Rd, Winchester, VA 22602
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
- Built 1997
Last Sold Summary
- 5% Above List Price
- $231/SF
- 2 Days On Market
Current Estimated Value $546,397

Last Listing Agent RoxAnn Grimes RE/MAX Roots

111 Old Wagon Rd, Winchester, VA 22602

/17
Not Listed For Sale

107 Nootka Way, Winchester, VA 22602
- 3 Beds
- 2.5 Baths
- 1,509 Sq Ft
- Built 2024
107 Nootka Way, Winchester, VA 22602

Last Sold Summary
- 114 Days On Market
Last Listing Agent Tracy Jennings D R Horton Realty of Virginia LLC

/46
$1,150,000
- 5 Beds
- 5 Baths
- 5,695 Sq Ft
801 Armistead St, Winchester, VA 22601

This home has a 2.25% VA Assumable Loan. There are homes that simply provide shelter. And then there are homes like this—homes that make you slow down, take a deep breath, and picture the life you've been working so hard to create. Nestled in one of Winchester's most beloved neighborhoods, this stately residence blends timeless elegance with the confidence that comes from knowing the important

Donna Chong Samson Properties

801 Armistead St, Winchester, VA 22601
/36
$390,000

Sold Aug 22, 2025

103 Sequoia Dr, Winchester, VA 22602
- 3 Beds
- 3.5 Baths
- 2,238 Sq Ft
- Built 2016
Last Sold Summary
- $174/SF
- 3 Days On Market
Current Estimated Value $404,134

Last Listing Agent Barton Chasler Realty ONE Group Old Towne

103 Sequoia Dr, Winchester, VA 22602

/17
Not Listed For Sale

105 Nootka Way, Winchester, VA 22602
- 3 Beds
- 2.5 Baths
- 1,509 Sq Ft
- Built 2024
105 Nootka Way, Winchester, VA 22602

Last Sold Summary
- 160 Days On Market
Last Listing Agent Tracy Jennings D R Horton Realty of Virginia LLC

/24
$155,000

$10K PRICE DROP
- 2 Beds
- 1 Bath
- 652 Sq Ft
616 Opossum Trail, Winchester, VA 22602

Escape to the peace and privacy of Wilde Acres with this charming 2-bedroom, 1-bath cabin situated on four lots for a total of 1 acre, offering extra space and the possibility of potential expansion. This property is being sold As-Is and is in need of some cosmetic work. It presents a great opportunity for a weekend retreat, investment property, or full-time residence with a little TLC. Recent

Dona Shiley ERA Oakcrest Realty, Inc.

616 Opossum Trail, Winchester, VA 22602
/9
$95,000

Sold Aug 22, 2025

1114 Cedar Grove Rd, Winchester, VA 22603
- 1 Bed
- 1 Bath
- Built 1957
Last Sold Summary
- 84 Days On Market
Current Estimated Value $94,099

Last Listing Agent Dave Spence RE/MAX Roots

1114 Cedar Grove Rd, Winchester, VA 22603

/16
Not Listed For Sale

109 Pawn Ct, Winchester, VA 22602
- 4 Beds
- 3 Baths
- 3,100 Sq Ft
- Built 2025
109 Pawn Ct, Winchester, VA 22602

Last Sold Summary
- 127 Days On Market
Last Listing Agent Jay Day LPT Realty, LLC

/37
$360,000

New Construction Open Sat 1PM - 3PM
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
302 Pheasant Dr, Winchester, VA 22602

NEW CONSTRUCTION built by a trusted local builder with over 20 years of experience! This beautifully crafted 3-bedroom, 2-bath ranch home offers the perfect blend of quality construction and modern finishes. Built using the ZIP System® exterior sheathing for enhanced weather protection and durability, this home was designed with attention to detail from the ground up. Inside, you’ll find an

Tyler Hazelwood Virginia Real Estate

302 Pheasant Dr, Winchester, VA 22602
/2
$346,900

Sold Oct 14, 2025

111 Comanche Trail, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 1,422 Sq Ft
- Built 1992
Last Sold Summary
- $244/SF
- 2 Days On Market
Current Estimated Value $342,840

Last Listing Agent George Glaize George W. Glaize, Jr., Inc. REALTOR

111 Comanche Trail, Winchester, VA 22602

/22
Est $342,466

Not Listed For Sale

821 Pheasant Dr, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 1,545 Sq Ft
- Built 2024
821 Pheasant Dr, Winchester, VA 22602

Last Sold Summary
- 20 Days On Market
Last Listing Agent Paige Ulevich Dream Real Estate

/7
$1,100,000

Under Contract
- Land
- 2.3 Acres
- $478,261 per Acre
0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601

2.3 Acre Outparcel on Pleasant Valley Road for Sale Neighbors include Walmart, Ross, Target, Panera Bread, Olive Garden, Petco, and the list goes on! Zoned CM1, ideal for auto sales, offices, retail, and flex development. All utilities to site. Outstanding proximity to massive commercial and multifamily growth. VA's fastest growing City in it's fastest growing commercial district. Almost 500'

Gillian Greenfield Coldwell Banker Premier

0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601
/27
$127,000

Sold Jul 20, 2026

0 Bass Ln Unit VAFV2043092, Winchester, VA 22603
- Land
- 3.43 Acres
- $37,026 per Acre
Last Sold Summary
- 2% Below List Price
- 3 Days On Market
Last Listing Agent Cara Wilkins MarketPlace REALTY

0 Bass Ln Unit VAFV2043092, Winchester, VA 22603

/26
Est $342,621

Not Listed For Sale

114 Mountain Lodge Dr, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
- Built 2025
114 Mountain Lodge Dr, Winchester, VA 22602

Last Sold Summary
- 50 Days On Market
Last Listing Agent Abby Walters Preslee Real Estate

Showing Results 561 - 600, Page 15 of 18

Virginia Winchester County

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