Winchester, VA Homes

/21
$250,000

$35K PRICE DROP Under Contract
- 3 Beds
- 1 Bath
- 1,094 Sq Ft
143 Dowell J Cir, Winchester, VA 22602

Prime Location and Endless Potential! This well-built, single-level rancher offers 3 bedrooms and 1 full bath across 1,000 square feet of smartly designed living space. Nestled on a quiet street just outside Winchester city limits, this home falls within the Frederick County school district and combines peaceful surroundings with unbeatable convenience—just one minute to Rt. 7, I-81, Martins

Sarah Hott Realty ONE Group Old Towne

143 Dowell J Cir, Winchester, VA 22602
/14
$2,195 Per Month
- 4 Beds
- 3.5 Baths
- 1,889 Sq Ft
- Townhouse for Rent
176 Sequoia Dr, Winchester, VA 22602

Brand-New Townhome for Rent in Retreat at Winding Creek!Welcome to this beautifully designed 3-level townhome offering 3 bedrooms, 2.5 bathrooms, and an attached one-car garage in the desirable Retreat at Winding Creek community. This never-lived-in home features an open floor plan with 9-foot ceilings, luxury vinyl plank flooring, and plenty of natural light throughout.The modern kitchen

Vijaya Rallabandi Partners Real Estate

176 Sequoia Dr, Winchester, VA 22602
/41
$318,000

Sold Jan 09, 2026

206 Eastside Ln, Winchester, VA 22602
- 3 Beds
- 3.5 Baths
- 1,886 Sq Ft
- Built 2006
Last Sold Summary
- $169/SF
- 68 Days On Market
Current Estimated Value $318,069

Last Listing Agent Adam Brand Pearson Smith Realty, LLC

206 Eastside Ln, Winchester, VA 22602

/60
Est $921,471

Not Listed For Sale

172 Winding Hill Rd, Winchester, VA 22603
- 4 Beds
- 3.5 Baths
- 3,107 Sq Ft
- Built 2021
172 Winding Hill Rd, Winchester, VA 22603

Last Sold Summary
- 8 Days On Market
Last Listing Agent Dave Spence RE/MAX Roots

/5
$10,000

Under Contract
- Land
- 11,325 Sq Ft
- $38,462 per Acre
Lot 11 Pheasant Dr, Winchester, VA 22602

Discover a serene 0.26-acre lot nestled in Winchester's Wilde Acres / Mountain Falls Subdivision, where nature meets tranquility. This beautifully wooded parcel offers a perfect canvas for your dream home, surrounded by lush trees that provide both privacy and a picturesque backdrop. With convenient road frontage, access to your future home or cozy weekend retreat is effortless.

Bridget Aikens Colony Realty

Lot 11 Pheasant Dr, Winchester, VA 22602
/15
$1,400

Total Monthly Price
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
- House for Rent
1001 S Cameron St, Winchester, VA 22601

•Built in 1930. ••3 Bedroom - 1 Bath Duplex. ••Convenient in-town location. Close to Valley Ave, Pleasant Valley Rd., Rt.522 S. and I-81. ••Refrigerator / Stove. • •Hardwood floors / Vinyl in kitchen and bath ••Gas Furnace Heat. / No AC ••Dirt Floor Cellar• •On Street Parking. ••Quarterly Preventive Pest Service. ••Sorry No Pets•• Tenant

1001 S Cameron St, Winchester, VA 22601
/35
$359,641

Sold Nov 14, 2025

153 Denny, Winchester, VA 22603
- 3 Beds
- 3 Baths
- 1,644 Sq Ft
- Built 2010
Last Sold Summary
- $219/SF
- 14 Days On Market
Current Estimated Value $360,523

Last Listing Agent Stephanie Ryall Realty ONE Group Old Towne

153 Denny, Winchester, VA 22603

/4
Not Listed For Sale

0 Bluebird Trail Unit VAFV2024304, Winchester, VA 22602
0 Bluebird Trail Unit VAFV2024304, Winchester, VA 22602

Last Sold Summary
- 54 Days On Market
Last Listing Agent Jeffrey Konrady Realty ONE Group Old Towne

/42
$445,000

$45K PRICE DROP Under Contract
- 3 Beds
- 2.5 Baths
- 1,745 Sq Ft
430 Babbs Mountain Rd, Winchester, VA 22603

Desirable location off of Apple Pie Ridge. With some TLC, this 3-bedroom, 2.5-bath home set on 2.68 wooded acres just minutes from Winchester Medical Center, offering a private, peaceful setting with everyday convenience. Enjoy the outdoors from the covered front porch or rear deck—perfect for relaxing or entertaining. Inside, the spacious kitchen features a center island, stainless steel

Sheila Pack RE/MAX Roots

430 Babbs Mountain Rd, Winchester, VA 22603
/19
$1,500 Per Month
- 2 Beds
- 1.5 Baths
- 1,106 Sq Ft
- Townhouse for Rent
544 Allston Cir, Winchester, VA 22601

NO PETS. 2bedroom 1.5 bath townhouse located minutes to shops and dining in Winchester. Central heating and AC. Large primary bedroom. Unfinished walkout basement. Requirements: (1) Minium household annual income $67k, (2) Good Credit, (3) Good Landlord Reference. $47 application fee per applicant. Contact listing agent for application

Courtney Spaid Crum Realty, Inc.

544 Allston Cir, Winchester, VA 22601
/91
$685,000

Sold Mar 31, 2026

225 Lehigh Dr, Winchester, VA 22602
- 7 Beds
- 3.5 Baths
- 4,276 Sq Ft
- Built 2023
Last Sold Summary
- 2% Below List Price
- $160/SF
- 46 Days On Market
Current Estimated Value $677,972

Last Listing Agent RAFIQUE JAMAL Pi Realty Group, Inc.

225 Lehigh Dr, Winchester, VA 22602

/55
Not Listed For Sale

169 Munsee Cir, Winchester, VA 22602
- 4 Beds
- 3.5 Baths
- 1,889 Sq Ft
- Built 2025
169 Munsee Cir, Winchester, VA 22602

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

/69
$529,900

$10K PRICE DROP Under Contract
- 4 Beds
- 4 Baths
- 4,055 Sq Ft
110 Grindstone Dr, Winchester, VA 22602

Private pool, half-acre homesite, main-level living, and a fully finished lower-level living suite make this one of Winchester's most unique opportunities. Situated on a .53-acre lot established before the development of Red Fox Run, this property offers a level of privacy, outdoor space, and flexibility rarely found in today's subdivision homes.The main level features three bedrooms and

Daune Zook Samson Properties

110 Grindstone Dr, Winchester, VA 22602
/10
$1,895

Total Monthly Price
- 3 Beds
- 2.5 Baths
- 1,308 Sq Ft
- Townhouse for Rent
304 Emily Ln, Winchester, VA 22602

Wonderful townhome on the eastern part of Frederick County near route 7. Fresh paint, new upgraded flooring, carpet, and large deck in rear! Private extra FULL bathroom in primary bedroom upstairs. Two FULL baths will make morning routines much better for all! Newer carpet and flooring. Home is ready for Loving tenants. Washer Dryer are not guaranteed or warranted

304 Emily Ln, Winchester, VA 22602
/72
$700,000

Sold Oct 29, 2025

292 Green Spring Rd, Winchester, VA 22603
- 4 Beds
- 4.5 Baths
- 4,320 Sq Ft
- Built 1990
Last Sold Summary
- $162/SF
- 87 Days On Market
Current Estimated Value $771,952

Last Listing Agent Katie Landi Jordan Samson Properties

292 Green Spring Rd, Winchester, VA 22603

/55
Not Listed For Sale

167 Munsee Cir, Winchester, VA 22602
- 4 Beds
- 3.5 Baths
- 1,889 Sq Ft
- Built 2025
167 Munsee Cir, Winchester, VA 22602

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

/72
$619,900

$30K PRICE DROP Pending
- 4 Beds
- 2.5 Baths
- 3,157 Sq Ft
153 Harvest Ridge Dr, Winchester, VA 22601

Welcome to 153 Harvest Ridge Drive, 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

Jonathan Minerick Homecoin.com

153 Harvest Ridge Dr, Winchester, VA 22601
/21
$1,550 Per Month
- 2 Beds
- 1 Bath
- 800 Sq Ft
- Condo for Rent
443 N Loudoun St Unit 2, Winchester, VA 22601

Beautiful 2 bedroom apartment just blocks from Old Town walking mall! Hardwood floors throughout, beautiful woodwork, nice size kitchen with stainless appliances, huge bathroom, and washer/dryer in unit! Upstairs are two bedrooms with wood floors, and parking is included in the rear! MUST have at least $3875 in monthly income and GOOD credit! One pet, case by case, must be up to date on vaccines

Misty Weaver Samson Properties

443 N Loudoun St Unit 2, Winchester, VA 22601
/2
$800,000

Sold Oct 29, 2025

601 Fall Run Ln, Winchester, VA 22602
- 3 Beds
- 2 Baths
- 2,175 Sq Ft
- Built 2022
Last Sold Summary
- $368/SF
- 75 Days On Market
Current Estimated Value $804,588

Last Listing Agent Theo Theologis Slones Real Estate

601 Fall Run Ln, Winchester, VA 22602

/55
Not Listed For Sale

165 Munsee Cir, Winchester, VA 22602
- 4 Beds
- 3.5 Baths
- 1,889 Sq Ft
- Built 2025
165 Munsee Cir, Winchester, VA 22602

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

/74
$650,000

$25K PRICE DROP Pending
- 7 Beds
- 3.5 Baths
- 4,116 Sq Ft
256 Skylar Lanes Way, Winchester, VA 22603

Welcome to this beautifully maintained home in the highly sought-after Walnut Springs Estates subdivision, offering exceptional space,comfort, and versatility on a private 2-acre lot. With up to 7 bedrooms and 3.5 bathrooms, this property is ideal for growing families, multi-generationalliving, or those who simply desire room to spread out. The inviting living room features a cozy electric

Brian Ratliff Old Dominion Realty

256 Skylar Lanes Way, Winchester, VA 22603
/24
$1,600 Per Month
- 2 Beds
- 1.5 Baths
- 2,202 Sq Ft
- Townhouse for Rent
235 Millwood Ave, Winchester, VA 22601

Beautiful apt right in Old Town - grab your coffee across the street each morning, and relax on your patio each evening! This 2 bedroom 1.5 bath duplex is well cared for, with a welcoming front porch that leads into the open living room and kitchen with bar seating area. The kitchen is fully stocked with stainless appliances and tons of cabinetry and counter space. There is even storage space

Misty Weaver Samson Properties

235 Millwood Ave, Winchester, VA 22601
/32
$400,000

Sold Oct 09, 2025

225 Parkway St, Winchester, VA 22601
- 4 Beds
- 2 Baths
- 2,256 Sq Ft
- Built 1928
Last Sold Summary
- $177/SF
- 13 Days On Market
Current Estimated Value $418,635

Last Listing Agent Tracy Jewell Samson Properties

225 Parkway St, Winchester, VA 22601

/55
Not Listed For Sale

163 Munsee Cir, Winchester, VA 22602
- 4 Beds
- 3.5 Baths
- 1,889 Sq Ft
- Built 2025
163 Munsee Cir, Winchester, VA 22602

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

/75
$515,000

Under Contract
- 4 Beds
- 3.5 Baths
- 2,995 Sq Ft
121 Fortress Dr, Winchester, VA 22603

Welcome home to this spacious 4-bedroom, 3.5-bath Colonial in the conveniently located Star Fort subdivision. Offering three finished levels of comfortable living space, this home combines functionality, charm, and an ideal location. The main level features beautiful hardwood floors, a formal dining room, and a large family room with a cozy gas fireplace that flows into the spacious kitchen,

Laura White ERA Oakcrest Realty, Inc.

121 Fortress Dr, Winchester, VA 22603
/23
$2,300 Per Month
- 4 Beds
- 3.5 Baths
- 2,094 Sq Ft
- Townhouse for Rent
124 Swansong Place, Winchester, VA 22603

Welcome to 124 Swansong Place in sought-after Snowden Bridge - a brand new Brookfield Residential Skyline townhome offering 4 bedrooms, 3.5 baths, and three finished levels of stylish living. The open main level is anchored by a huge center island kitchen with quartz countertops, stainless steel appliances, abundant prep space, and a separate dining area that flows easily into the living space.

Sarah Brown RE/MAX Gateway

124 Swansong Place, Winchester, VA 22603
/21
$485,000

Sold May 26, 2026

107 Sunflower Way, Winchester, VA 22603
- 3 Beds
- 3 Baths
- 2,050 Sq Ft
- Built 2026
Last Sold Summary
- 7% Below List Price
- $237/SF
- 60 Days On Market
Last Listing Agent Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

107 Sunflower Way, Winchester, VA 22603

/28
Not Listed For Sale

126 Manasquan Way, Winchester, VA 22602
- 4 Beds
- 2.5 Baths
- 1,953 Sq Ft
- Built 2025
126 Manasquan Way, Winchester, VA 22602

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

/40
$329,000

Under Contract
- 3 Beds
- 1.5 Baths
- 2,203 Sq Ft
912 Allen Dr, Winchester, VA 22601

Charming, meticulously maintained brick rancher in the heart of Winchester City! This move-in-ready home features 3 spacious bedrooms, 1 full bath, and a convenient half bath. Step inside to find gorgeous hard wood floors and several rooms boasting fresh, modern paint. The fully finished basement ( with radon system installed) offers incredible bonus square footage, perfect for a family room,

Karen O'Hare Colony Realty

912 Allen Dr, Winchester, VA 22601
/6
$1,350 Per Month
- 1 Bed
- 1 Bath
- 400 Sq Ft
- Condo for Rent
4 W Cork St Unit 1, Winchester, VA 22601

Welcome to Apt. 1 at 4 W. Cork Street, a beautifully located residence in the heart of historic downtown Winchester. This inviting apartment offers the perfect blend of character, convenience, and city living. Enjoy easy access to local restaurants, coffee shops, boutiques, entertainment, and the vibrant Old Town walking mall—all just steps from your front door.

Patrick Slate Keller Williams Realty

4 W Cork St Unit 1, Winchester, VA 22601
/52
$410,000

Sold Jul 09, 2026

1115 Opequon Ave, Winchester, VA 22601
- 3 Beds
- 2 Baths
- 2,067 Sq Ft
- Built 1971
Last Sold Summary
- 2% Below List Price
- $198/SF
- 16 Days On Market
Current Estimated Value $414,147

Last Listing Agent Sheila Pack RE/MAX Roots

1115 Opequon Ave, Winchester, VA 22601

/28
Not Listed For Sale

101 Monacan St, Winchester, VA 22602
- 4 Beds
- 2.5 Baths
- 1,953 Sq Ft
- Built 2025
101 Monacan St, Winchester, VA 22602

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

/8
$785,000

New Construction Pending
- 3 Beds
- 3 Baths
- 2,548 Sq Ft
0 Apple Pie Ridge Rd Unit VAFV2039276, Winchester, VA 22603

Dogwood - One Story Living Carrington Homes Western Loudoun’sPremiere Home builder introduces its newWinchester Collection of single familyHomes on a private 2 acre lot.Custom style homes designedBy James McDonald Architects One story and two story plans withFirst floor multi generational options available DECORATED MODELS located at 156 Covey Lane Winchester

Daniel Boris Pearson Smith Realty, LLC

0 Apple Pie Ridge Rd Unit VAFV2039276, Winchester, VA 22603
/14
$1,350 Per Month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Townhouse for Rent
220 E Whitlock Ave, Winchester, VA 22601

Conveniently located near Downtown Winchester, Shenandoah University, shopping, restaurants, and other everyday amenities, this well-maintained 2-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.

220 E Whitlock Ave, Winchester, VA 22601
/24
$370,000

Sold Nov 14, 2025

613 Laurelwood Cir, Winchester, VA 22601
- 3 Beds
- 2.5 Baths
- Built 2025
Last Sold Summary
- 35 Days On Market
Last Listing Agent Dev Patel Samson Properties

613 Laurelwood Cir, Winchester, VA 22601

/31
Not Listed For Sale

0 Bear Trail Unit VAFV2023242, Winchester, VA 22602
0 Bear Trail Unit VAFV2023242, Winchester, VA 22602

Last Sold Summary
- 137 Days On Market
Last Listing Agent Chad Pangle Whitetail Properties Real Estate, LLC

/15
$89,000
- Land
- 6.11 Acres
- $14,566 per Acre
0 Pack Horse Road Lot A Unit VAFV2042702, Winchester, VA 22603

The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 6.11 lot A is wooded, has a Frederick County cert letter (see documents from health department however buyer should do due diligence). Unrestricted and so think about the possibilities for a homestead, simple get away to enjoy quiet and tranquility, and/or the new

Dave Spence RE/MAX Roots

0 Pack Horse Road Lot A Unit VAFV2042702, Winchester, VA 22603
/21
$1,350 Per Month
- 1 Bed
- 1 Bath
- 450 Sq Ft
- Condo for Rent
116 N Indian Aly Unit 102, Winchester, VA 22601

Live, work, and play in the heart of Historic Downtown Winchester! Be the first to enjoy this beautifully renovated lower-level 1-bedroom, 1-bathroom apartment, ideally located on Indian Alley directly across from the Braddock Street Parking Garage and just steps from the Old Town Walking Mall's shops, restaurants, breweries, and entertainment. Freshly updated throughout, this apartment features

Chris Roszko Colony Realty

116 N Indian Aly Unit 102, Winchester, VA 22601
/51
$725,000

Sold Mar 23, 2026

806 Mahone Dr, Winchester, VA 22601
- 4 Beds
- 2.5 Baths
- 2,442 Sq Ft
- Built 1999
Last Sold Summary
- 2% Below List Price
- $297/SF
- 1 Day On Market
Current Estimated Value $744,660

Last Listing Agent Tiffany Hunter ERA Oakcrest Realty, Inc.

806 Mahone Dr, Winchester, VA 22601

/32
Not Listed For Sale

124 Manasquan Way, Winchester, VA 22602
- 5 Beds
- 3 Baths
- 2,415 Sq Ft
- Built 2025
124 Manasquan Way, Winchester, VA 22602

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

Showing Results 361 - 400, Page 10 of 18

Virginia Winchester County

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