Winchester, VA Homes

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  /56

  $499,000

  • 4 Beds
  • 3.5 Baths
  • 3,982 Sq Ft

  202 Senseny Glen Dr, Winchester, VA 22602

  Located in the sought after neighborhood of Senseny Glen, this meticulously cared for rancher has been thoughtfully maintained by the current owners, going above and beyond to ensure it’s in outstanding condition. Offering over 3,700 square feet of finished living space on a quiet corner lot, it’s also conveniently located near restaurants, shopping, local schools, Route 7, and I-81. Inside,

  Liz Owings RE/MAX Roots

  202 Senseny Glen Dr, Winchester, VA 22602
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  /57

  $1,500 per month

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Townhouse for Rent

  127-A Peyton St, Winchester, VA 22601

  Gorgeous two story apartment with private entrance in the heart of historic downtown Winchester2 bedroom 1.5 bath two floor apartment with beautiful details located in the bottom two levels of a four story house built in the early 1890s.

  127-A Peyton St, Winchester, VA 22601
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  /63

  $391,000 Sold Sep 03, 2025

  • 1,870 Sq Ft
  • $209/SF
  • 7 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1992

  101 Etnam St, Winchester, VA 22602

  Welcome to 101 Etnam Street, where charm, space, and flexibility come together in a beautifully maintained home just minutes from downtown Winchester. Step inside from the inviting covered front porch—perfect for relaxing with your morning coffee, and discover a versatile floor plan with room for everyone. This home was just installed with a BRAND NEW dual zoned HVAC System ( gas furnace for the

  Bailey Cooper RE/MAX Gateway

  101 Etnam St, Winchester, VA 22602
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  /45

  Est $582,256 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,426 Sq Ft

  2040 Taylor Grace Ct, Winchester, VA 22601

  2040 Taylor Grace Ct, Winchester, VA 22601
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  /66

  $510,000

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  580 N Braddock St, Winchester, VA 22601

  Step into the charm of 1920s architecture seamlessly blended with today’s comforts. This beautifully restored 4-bedroom, 2.5-bath home offers over 2,200 sq ft of finished living space across three levels.Inside, you’ll find a bright, open main level with wide-plank flooring, a cozy family room with stacked stone gas fireplace, and a gourmet kitchen featuring a massive island, stainless

  Payton Polychrones Samson Properties

  580 N Braddock St, Winchester, VA 22601
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  /17

  $1,750 per month

  • 3 Beds
  • 1.5 Baths
  • 1,210 Sq Ft
  • Townhouse for Rent

  358 Valley Mill Rd, Winchester, VA 22602

  READY FOR IMMED. OCCUPANCY! * HARDWOOD FLOORS * END UNIT * PLENTY OF PARKING * OWNER WILL CONSIDER PETS ON A CASE BY CASE BASIS * BAY WINDOW * WASHER & DRYER * CONVENIENT TO RT7, 81, Schools & shopping

  Tracy Wenger Samson Properties

  358 Valley Mill Rd, Winchester, VA 22602
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  /31

  $585,000 Sold Sep 03, 2025

  • 3,078 Sq Ft
  • $190/SF
  • 40 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2013

  114 Harvest Ridge Dr, Winchester, VA 22601

  Here is your chance to make the Village at Harvest Ridge your relaxing abode with abundance of open interior space and an true HOA who keeps your lawn in tip top shape. Being 55+ active adult community definitely has its up side for sure, but this immaculate craftsman ranch style has a floor plan where the kitchen has a ton of cabinetry and granite counter tops and the island has the bar seating

  Dave Spence RE/MAX Roots

  114 Harvest Ridge Dr, Winchester, VA 22601
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  /31

  Est $340,126 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 1,740 Sq Ft

  123 Monticello Square, Winchester, VA 22602

  123 Monticello Square, Winchester, VA 22602
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  /46

  $620,000

  • 5 Beds
  • 3.5 Baths
  • 3,494 Sq Ft

  127 Kinross Dr, Winchester, VA 22602

  **New Price**Welcome to 127 Kinross Dr in Winchester, VA! This spacious 5-bedroom, 3.5-bath home offers 3,494 sq. ft. of beautifully updated living space with modern upgrades throughout. Located in the well sought-after RAVEN WING Community due to its perfect location and commuter friendly access to all major highways (Route 50, Route 7, Route 66 & Interstate 81), shopping and other great perks

  Matthew Roberts Redfin Corporation

  127 Kinross Dr, Winchester, VA 22602
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  /30

  $1,525 per month

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Townhouse for Rent

  157 Peyton St, Winchester, VA 22601

  Amazing location downtown Winchester. Fantastic community. Great neighbors whom have been part of our community for a long time.Hardwood floors.

  157 Peyton St, Winchester, VA 22601
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  /17

  $365,000 Sold Sep 03, 2025

  • 880 Sq Ft
  • $415/SF
  • 189 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2019

  482 Diamondback Ln, Winchester, VA 22602

  Nestled on approximately 10 acres of serene land, this peaceful retreat offers minimal restrictions and features a picturesque stream that enhances the natural landscape. The cozy one-level home, approximately 880 sq. ft., was built in 2019 and served as a successful Airbnb, offering the perfect balance of comfort and privacy. Whether you're looking to unwind in nature or create your own private

  Sheila Pack RE/MAX Roots

  482 Diamondback Ln, Winchester, VA 22602
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  /29

  Est $339,262 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  308 Fawn Dr, Winchester, VA 22602

  308 Fawn Dr, Winchester, VA 22602
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  /24

  $400,000

  • 3 Beds
  • 2.5 Baths
  • 1,970 Sq Ft

  158 Tye Ct, Winchester, VA 22602

  Welcome to this end-unit Lancaster Model by Lennar Homes which is only 2 years young and offers the perfect blend of modern style and low-maintenance living. The open-concept main level features durable LVP flooring, granite countertops, stainless steel appliances, and a spacious kitchen island with a deep sink, disposal, and bar seating. A convenient half bath completes the main floor. Just off

  Richie Hanna RE/MAX Gateway

  158 Tye Ct, Winchester, VA 22602
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  /23

  $1,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,488 Sq Ft
  • Townhouse for Rent

  107 Trade Wind Ln, Winchester, VA 22602

  Very nicely maintained 3-Bedroom 2.5 Bath townhome in highly sought Windstone Community! Ready for immediate occupancy, this property features hardwood floors and a gas fireplace in the Living Room, spacious eat-in Kitchen that walks out to back deck. Fantastic commuter location - very close to Rt 7, I-81, schools, restaurants, shopping and other in-town amenities. No Smoking allowed. A pet

  Bridget Aikens Colony Realty

  107 Trade Wind Ln, Winchester, VA 22602
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  /32

  $400,000 Sold Sep 02, 2025

  • 1,548 Sq Ft
  • $258/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  423 Crescent Dr, Winchester, VA 22601

  This charming one-level ranch is tucked away on a quiet cul-de-sac in the City of Winchester, just minutes from shopping, dining, and all the conveniences of town.Inside, updated hickory hardwood flooring flows throughout the home. The kitchen shines with updates, including new fixtures, quartzite countertops, and a fresh kitchen floor. The bathroom features an ADA-compliant shower, and

  Sharon Farinholt Realty ONE Group Old Towne

  423 Crescent Dr, Winchester, VA 22601
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  /30

  Est $339,390 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 1,740 Sq Ft

  117 Monticello Square, Winchester, VA 22602

  117 Monticello Square, Winchester, VA 22602
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  /56

  $589,900 Open Sun 1PM - 3PM

  • 4 Beds
  • 3 Baths
  • 3,259 Sq Ft

  128 Nevermore Dr, Winchester, VA 22602

  Veterans, this home has a 2.75 assumable interest rate. Built in 2021, this home shows like new. You'll love the gourmet kitchen with center island, gas cooktop, double ovens, French door refrigerator, quartz countertops, pendant lighting, light gray cabinets, tile backsplash & stainless steel appliances. The family room is adjacent to the kitchen and dining rooms and features an electric

  Gina Chatham Century 21 Redwood Realty

  128 Nevermore Dr, Winchester, VA 22602
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  /2

  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  382 Woodstock Ln, Winchester, VA 22601

  This property at 382 Woodstock Ln features 2 bedrooms and 1 bathroom within a total living space of 1,000 square feet. The living room offers ample space for relaxation and entertainment. The bathroom includes a tub/shower combination for convenience. Each bedroom is designed to accommodate various furniture arrangements and provides adequate closet space. Additional amenities include storage

  382 Woodstock Ln, Winchester, VA 22601
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  /68

  $445,000 Sold Sep 02, 2025

  • 2,268 Sq Ft
  • $196/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  103 Woodbury Ct, Winchester, VA 22602

  Discover the charm of this beautifully renovated split foyer home nestled in the serene Asbury Terrace community. With a major renovation completed in 2025, this residence seamlessly blends modern comforts with timeless appeal. The inviting layout features three spacious bedrooms and three full bathrooms, ensuring ample space for relaxation and privacy. Step into the heart of the home, where a

  Lane McIntosh Mclntosh Realty Group

  103 Woodbury Ct, Winchester, VA 22602
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  /27

  Est $340,988 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 1,740 Sq Ft

  113 Monticello Square, Winchester, VA 22602

  113 Monticello Square, Winchester, VA 22602
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  /35

  $819,950

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft

  601 Fall Run Ln, Winchester, VA 22602

  What better than a custom-built home on 20+ acres that can be subdivided if you so wish?$50k price drop! Prepare to be captivated by the beauty and tranquility of this exceptional custom-built home, nestled on 20.10 acres with breathtaking mountain views. Offering desirable one-level living, this nearly new (under 3 years old) home boasts a gorgeous covered porch and an expansive deck

  Theo Theologis Slones Real Estate

  601 Fall Run Ln, Winchester, VA 22602
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  /20

  $3,400 per month

  • 2 Beds
  • 2.5 Baths
  • 1,981 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 204, Winchester, VA 22601

  This stunning apartment has nearly 2000 sq ft on one level. Just steps from all of the restaurants, night life and events in Old Town Winchester. The historic Winchester Star building has been renovated for luxury living that includes private parking, a rarity downtown. There are two large bedrooms, each with their own en-suite and walk-in closet, ample living and dining spaces, a separate

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 204, Winchester, VA 22601
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  /47

  $450,000 Sold Sep 02, 2025

  • 2,047 Sq Ft
  • $220/SF
  • 1 Day On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  109 Senseny Glen Dr, Winchester, VA 22602

  Beautiful brick front home in the sought after Senseny Glen community! Perfectly located with easy access to commuter routes and local amenities. You'll find plenty of parking with a large driveway and two car garage. Start your tour at the charming brick paver walkway, which leads to a covered portico entrance. The entry level is bright and airy, with columns to delineate spaces while

  Amanda White Nova Home Hunters Realty

  109 Senseny Glen Dr, Winchester, VA 22602
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  /58

  Est $677,031 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,912 Sq Ft

  730 Old Baltimore Rd, Winchester, VA 22603

  730 Old Baltimore Rd, Winchester, VA 22603
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  /55

  $609,900 Open Sat 10AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,618 Sq Ft

  281 Light Rd, Winchester, VA 22603

  Price Improvement! Motivated Sellers! Bring your offers! Main Level Living! POOL! 5 GARAGE SPACES, POLE BARN & MORE! Appraised for $646,000! Ranch-Style Retreat on almost 8.5 Acres in Frederick County, VA, 20 mins. from Winchester! Calling all Homesteaders - your Farmette awaits! This property offers endless possibilities, any type of hobby, gardening, farmette, horses, workshop,

  Jennifer Watt Century 21 Redwood Realty

  281 Light Rd, Winchester, VA 22603
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  /6

  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  372 Woodstock Ln, Winchester, VA 22601

  This 2-bedroom, 1-bathroom property located at 372 Woodstock Ln offers 1,000 square feet of living space. The living room provides ample room for relaxation and entertainment. The bathroom features a tub/shower combination for convenience. Each bedroom is designed to accommodate various furniture arrangements. Additional amenities include storage space and heating for year-round comfort. The

  372 Woodstock Ln, Winchester, VA 22601
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  /57

  $675,000 Sold Sep 02, 2025

  • 5,201 Sq Ft
  • $130/SF
  • 14 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2005

  105 Braxton Ct, Winchester, VA 22602

  Welcome to 105 Braxton Ct, Winchester VA!This stunning Colonial-style home offers over 3,500 square feet of beautifully updated living space with modern features throughout. Step inside to an inviting open floor plan that seamlessly blends functionality with style, featuring formal living and dining areas, a well-appointed kitchen, and a main-level den, ideal for those of you who work from

  Lisa Behr Coldwell Banker Premier

  105 Braxton Ct, Winchester, VA 22602
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  /32

  Est $330,492 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,488 Sq Ft

  134 Windstone Dr, Winchester, VA 22602

  134 Windstone Dr, Winchester, VA 22602
• 

  

  /18

  $454,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,665 Sq Ft

  226 Munsee Cir, Winchester, VA 22602

  Step into 1,657 square feet of well-designed living space in the Cabral, featuring 3 spacious bedrooms, 2.5 bathrooms, and a flexible loft upstairs—perfect for a home office, playroom, or additional lounge area. This home showcases a charming Linen siding exterior with brick accents, while the interior boasts sleek gray kitchen and bathroom cabinets paired with modern finishes throughout. Enjoy

  

  D.R. Horton

  Builder

  226 Munsee Cir, Winchester, VA 22602
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  /32

  $3,100 per month

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft
  • Condo for Rent

  210 E Boscawen St Unit 202, Winchester, VA 22601

  This stunning apartment features 9 south facing windows for maximum natural light, just steps from all of the restaurants, night life and events in Old Town Winchester. The historic Winchester Star building has been renovated for luxury living that includes private parking, a rarity downtown. Two large bedrooms, each with their own en-suite and walk-in closet are set apart by the open space

  Katie Landi Jordan Samson Properties

  210 E Boscawen St Unit 202, Winchester, VA 22601
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  /14

  $338,955 Sold Aug 29, 2025

  • 1,442 Sq Ft
  • $235/SF

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  629 Laurelwood Cir, Winchester, VA 22601

  Fall Move-In Poplar Available at Laurelwood Commons!This home features 3 bedrooms, 2.5 baths, 1,442 sq. ft., upgraded kitchen with white cabinets, quartz counters, island, LVP throughout the main level & more! Plus, enjoy all closing costs paid with use of NVR Mortgage!*. Learn more!

  Ryan Homes

  629 Laurelwood Cir, Winchester, VA 22601
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  /11

  Est $238,523 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  164 Brookland Ct Unit 11, Winchester, VA 22602

  164 Brookland Ct Unit 11, Winchester, VA 22602
• 

  

  /18

  $449,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft

  216 Munsee Cir, Winchester, VA 22602

  The Cabral offers 1,657 square feet of thoughtfully designed living space, featuring 3 spacious bedrooms, 2.5 bathrooms, and a versatile loft on the bedroom level—perfect for a home office, playroom, or additional lounge area. This home features a beautiful cypress green exterior with stone accents, and inside, you’ll find stylish white kitchen and bathroom cabinets paired with modern finishes

  

  D.R. Horton

  Builder

  216 Munsee Cir, Winchester, VA 22602
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  /6

  $1,400 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  376 Woodstock Ln, Winchester, VA 22601

  This property at 376 Woodstock Ln features 2 bedrooms and 1 bathroom within a total of 1,000 square feet. The living room provides ample space for relaxation and entertainment. The bathroom is equipped with a tub/shower combination, catering to various preferences. Each bedroom offers sufficient room for furniture and personal items. Additional amenities include storage space and heating for

  376 Woodstock Ln, Winchester, VA 22601
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  /2

  $150,000 Sold Aug 29, 2025

  • 1,678 Sq Ft
  • $89/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 1910

  315 National Ave, Winchester, VA 22601

  Colonial with separate lower and upper living units located blocks from downtown Winchester & the local library. Upper level is a 1 Bed/1 Bath with living room & kitchen and laundry hook-ups. Lower level is a 1 Bed/1 Bath with living room & kitchen and no laundry hook-ups.Property sold AS IS.Access from Jolley Lane and parking in rear of property.

  Sheila Pack RE/MAX Roots

  315 National Ave, Winchester, VA 22601
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  /35

  Est $243,239 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  147 Brookland Ct Unit 6, Winchester, VA 22602

  147 Brookland Ct Unit 6, Winchester, VA 22602
• 

  

  /30

  $551,724 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,263 Sq Ft

  108 Webster Ct, Winchester, VA 22603

  Welcome to the Vale 34-F2 – Homesite 1048 at Hiatt Pointe—a two-car, front-load garage villa with three bedrooms, two full bathrooms, and one half bathroom will be ready SEPTEMBER 2025. Open and adaptable, this factory-framed floorplan blends functionality with comfort. Enter through the welcoming front porch and be immediately greeted by 9’ ceilings on both levels, oak main stairs, and expertly

  Shannon L Bray Pearson Smith Realty, LLC

  108 Webster Ct, Winchester, VA 22603
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  /38

  $2,350 per month

  • 4 Beds
  • 3.5 Baths
  • 2,291 Sq Ft
  • Townhouse for Rent

  148 Solara Dr, Winchester, VA 22602

  Check out this immaculately maintained 2,300 square foot end-unit townhome for rent in the highly sought-after Fieldstone community! Featuring 3 spacious bedrooms and 3.5 bathrooms, this home offers the perfect blend of comfort, space, and style.One of our favorite features is the expansive walk-out basement, which opens to a large, level backyard that backs to serene woods—ideal for

  Gayle Bailey Keller Williams Realty

  148 Solara Dr, Winchester, VA 22602
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  /28

  $350,000 Sold Aug 29, 2025

  • 2,075 Sq Ft
  • $169/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  201 Winchester Dr, Winchester, VA 22602

  Welcome to this beautiful 3-bedroom, 2-bathroom split-level home, a brand-new build nestled on a spacious 0.25-acre lot in the Mountain Falls Park community. (All photos similar) Enjoy a warm welcome with a cozy covered porch. Inside, the home features luxury vinyl plank flooring throughout, providing a modern, durable finish. The kitchen is a chef's delight, with stainless steel appliances,

  Sheila Pack RE/MAX Roots

  201 Winchester Dr, Winchester, VA 22602
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  /29

  Est $256,428 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft

  151 Brookland Terrace Unit 12, Winchester, VA 22602

  151 Brookland Terrace Unit 12, Winchester, VA 22602

Showing Results 161 - 200, Page 5 of 18