Winchester, VA Homes

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  /37

  $399,000

  • 3 Beds
  • 3.5 Baths
  • 2,083 Sq Ft

  104 Metcalf Terrace, Winchester, VA 22602

  Nestled in the charming Freedom Manor community, this beautifully designed Colonial townhouse offers a perfect blend of comfort and modern living. Built in 2021, the home features an inviting open floor plan that seamlessly connects the family room, dining area, and a stylish kitchen equipped with upgraded countertops and stainless steel appliances, including a built-in microwave and

  Wendy Conner Coldwell Banker Premier

  104 Metcalf Terrace, Winchester, VA 22602
• 

  

  

  /19

  $1,500 per month

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  926 Armistead St, Winchester, VA 22601

  926 Armistead St, Winchester, VA 22601
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  /34

  $412,000 Sold Jul 23, 2025

  • 1,762 Sq Ft
  • $234/SF
  • 136 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2006

  2320 Tower Ave, Winchester, VA 22601

  Seller is offering $10,000 closing cost assistance!!!Don't drag your feet before this one disappear!!! Welcome to 2320 Tower Ave , Two Car garages ,4 legal bedrooms , 2 full bathrooms single family in quiet cul-de-sac is what you are waiting for is finally here to make it yours, the entire house just came out of renovations from freshly painted , Master Bathroom/Quartz, High

  Alex Adomako-Acheampong Samson Properties

  2320 Tower Ave, Winchester, VA 22601
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  /30

  Est $338,961 Not Listed For Sale

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

  117 Monticello Square, Winchester, VA 22602

  117 Monticello Square, Winchester, VA 22602
• 

  

  

  /50

  $699,000

  • 4 Beds
  • 3.5 Baths
  • 4,167 Sq Ft

  132 Cahille Dr, Winchester, VA 22602

  Elegant Colonial with Theater Room, Stone Water Features & Luxury Upgrades in Raven Pointe Welcome to your dream home in the highly sought-after Raven Pointe neighborhood! This beautifully maintained 4-bedroom, 3.5-bath colonial, built in 2005, offers nearly 4,000 sq ft of luxurious living space on a serene 0.28-acre lot. Thoughtfully designed for both entertaining and everyday comfort, this home

  Jonathan Minerick Homecoin.com

  132 Cahille Dr, Winchester, VA 22602
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  /58

  $3,500 per month

  • 4 Beds
  • 3 Baths
  • 3,060 Sq Ft
  • House for Rent

  209 N Washington St, Winchester, VA 22601

  Live in the heart of historic Winchester! This beautifully maintained 1853 home on Washington Street offers more than just a place to live—it’s a lifestyle. With over 3,000 square feet of finished space, this one-of-a-kind rental blends timeless character with modern updates just blocks from the Old Town Walking Mall and steps from the Apple Blossom Parade Route.Inside, you’ll find

  Chris Roszko Colony Realty

  209 N Washington St, Winchester, VA 22601
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  /25

  $360,000 Sold Jul 22, 2025

  • 1,344 Sq Ft
  • $268/SF
  • 4 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1986

  108 Oakmont Cir, Winchester, VA 22602

  A Commuter’s Dream! Discover your perfect sanctuary in this beautifully maintained home located in a serene cul-de-sac in Winchester, VA. This inviting property features 3 Bedrooms, 1.5 Baths with Spacious Living Room, Open Kitchen and a beautiful spacious Backyard. Backyard has a Gazebo, Large deck and fenced in back yard. There is ample storage with 2 sheds that convey with the property.

  Stacey Mullins ERA Oakcrest Realty, Inc.

  108 Oakmont Cir, Winchester, VA 22602
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  /27

  Est $340,215 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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  /40

  $490,000

  • 5 Beds
  • 2 Baths
  • 1,956 Sq Ft

  116 S Pleasant Valley Rd, Winchester, VA 22601

  Welcome to 116 South Pleasant Valley Road! This fully-renovated gem has been meticulously transformed to offer a truly luxurious and modern living experience. You'll immediately appreciate the high-end finishes that grace every corner, making it feel brand new. The updated kitchen is a chef's delight, featuring new porcelain tile floors, sleek modern cabinetry, and stunning quartz countertops.

  Dan Whitacre Colony Realty

  116 S Pleasant Valley Rd, Winchester, VA 22601
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  /5

  $1,400 per month

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

  374 Woodstock Ln, Winchester, VA 22601

  This 2 bedroom 1 bathroom townhouse is located near the heart of Winchester. New renovations include flooring, cabinets, and paint.

  374 Woodstock Ln, Winchester, VA 22601
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  /37

  $268,000 Sold Jul 22, 2025

  • 1,214 Sq Ft
  • $221/SF
  • 13 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1996

  104 Braeburn Dr, Winchester, VA 22601

  Turnkey and full of charm, this brick-front townhome offers an ideal location near Route 7 and I-81. Inside, enjoy an open flow, warm natural light, and fresh updates throughout. The family room features hardwood floors and a bay window, while the kitchen boasts ceramic tile and gas cooking. A laundry room with washer and dryer on the main level adds convenience. Upstairs, the spacious primary

  Steph Mitchell Samson Properties

  104 Braeburn Dr, Winchester, VA 22601
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  /47

  Est $514,014 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,238 Sq Ft

  292 Fortress Dr, Winchester, VA 22603

  292 Fortress Dr, Winchester, VA 22603
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  /114

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 1,798 Sq Ft

  720 S Kent St, Winchester, VA 22601

  Welcome to the beautifully preserved American Foursquare where music legend Patsy Cline once lived with her mother—and later, with her husband, Charlie Dick. Built in 1931, this four-bedroom, one-and-a-half-bath home blends timeless character with thoughtful updates, all wrapped in the charm of one of Winchester’s most historic neighborhoods.Inside, you’ll find nearly 1,800 square feet of

  Krissy Cruse Pearson Smith Realty, LLC

  720 S Kent St, Winchester, VA 22601
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  /11

  $1,850 per month

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  307 Willowbrook Ct, Winchester, VA 22602

  Well maintained 3 bedroom, 1 1/2 bath townhouse end unit conveniently located close to Rt. 7 on the East end of Winchester . Nice size kitchen and living room area with attractive wood floors with 1/2 bath located on the main floor. Tenant to pay $ 1850.00 security deposit, $250 water/sewer hookup deposit and $ 30 mailbox deposit at the signing of the lease . Washer/Dryer hook up

  Jeff Boppe Long & Foster Real Estate, Inc.

  307 Willowbrook Ct, Winchester, VA 22602
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  /12

  $145,000 Sold Jul 21, 2025

  • 7 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1941

  381 National Ave, Winchester, VA 22601

  ***OFFER DEADLINE: SUNDAY JUNE 22ND AT 8PM!***Calling all investors, builders, and renovation enthusiasts—this is the opportunity you've been waiting for! This property is a true blank canvas with tons of potential. The home has been completely gutted and is ready for your vision—whether you're planning to renovate, rebuild, or start from scratch, the possibilities are wide open! With over

  Kevin Rodriguez Weichert, REALTORS

  381 National Ave, Winchester, VA 22601
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  /58

  Est $655,350 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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  /29

  $409,900

  • 3 Beds
  • 2.5 Baths
  • 1,962 Sq Ft

  117 Tye Ct, Winchester, VA 22602

  Modern, Move-In Ready Townhome with Premium UpgradesIdeally located just outside the bustle of Winchester with an easy commute to the DC Metro area, this 2023-built townhome offers the perfect balance of comfort, convenience, and style.Freshly and professionally painted throughout, the home features an open-concept main level with durable LVP flooring, granite countertops,

  Rick Cockrill Keller Williams Realty

  117 Tye Ct, Winchester, VA 22602
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  /10

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  316 Russelcroft Rd, Winchester, VA 22601

  Relax with the whole family at this peaceful place to stay.Discover your perfect family home-away-from-home! This charming 3-bed, 2-bath house offers stress-free living. Children will love the loft bed! Bikes, scooters, and a piano are available. Enjoy security and privacy in our pet-friendly, fenced-in backyard. Fully furnished for comfort and privacy. Located in a quiet, convenient

  316 Russelcroft Rd, Winchester, VA 22601
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  /23

  $365,000 Sold Jul 21, 2025

  • 1,680 Sq Ft
  • $217/SF
  • 12 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2022

  116 Copeley Cir, Winchester, VA 22602

  Beautifully appointed garage townhome available now in Freedom Manor. Less than 3 years old and ideally located on one of the best lots in the neighborhood! Fantastic floor plan offering that highly desirable main level entry making this the home you want for easy living and minimal stairs. Just a few of the interior upgrades include warm luxury vinyl plank flooring spanning the entire main level

  Mike Casto Weichert, REALTORS

  116 Copeley Cir, Winchester, VA 22602
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  /32

  Est $327,693 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
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  /48

  $574,900

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  1629 Pondview Dr, Winchester, VA 22601

  Discover tranquility and spacious living in this exceptional 4-bedroom, 3.5-bath home, with a main-level primary suite, ideally situated on one half of an acre backing to picturesque trees and wide-open fields. From the moment you step inside, you'll appreciate the meticulously maintained interior and inviting open floor plan. The living room features a cathedral ceiling and a cozy gas fireplace,

  Kerry & Ed Stinson Berkshire Hathaway HomeServices PenFed Realty

  1629 Pondview Dr, Winchester, VA 22601
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  /24

  $2,495 per month

  • 3 Beds
  • 2.5 Baths
  • Townhouse for Rent

  613 Laurelwood Dr, Winchester, VA 22602

  Brand new end-unit townhouse in Laurelwood Commons Community, located just minutes from the heart of downtown. This stylish two-story townhouse features a welcoming foyer that leads into a bright, open-concept great room, perfect for relaxing or entertaining. The gourmet kitchen is equipped with stainless steel appliances, ample cabinetry, and a spacious island that flows seamlessly into

  Dev Patel Samson Properties

  613 Laurelwood Dr, Winchester, VA 22602
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  /67

  $690,000 Sold Jul 21, 2025

  • 3,426 Sq Ft
  • $201/SF
  • 9 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2001

  960 Laurel Grove Rd, Winchester, VA 22602

  Interior photos to come!Welcome to 960 Laurel Grove Road — a peaceful retreat nestled in the scenic countryside of Winchester, VA. This charming property offers the perfect blend of comfort, space, and privacy, making it an ideal home for those seeking a quiet lifestyle without sacrificing convenience.Set on a generous lot surrounded by mature trees and natural beauty, this home

  Matt Leiva Keller Williams Realty

  960 Laurel Grove Rd, Winchester, VA 22602
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  /11

  Est $232,654 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
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  /32

  $499,900

  • 4 Beds
  • 4 Baths
  • 1,627 Sq Ft

  201 Parkway St, Winchester, VA 22601

  Freshly Renovated Charmer in Winchester!Welcome to 201 Parkway Street, a freshly updated home in the heart of Winchester! Previously tenant-occupied, this property has been thoughtfully refreshed and is ready for new owners. Recent Updates Include:Fresh interior paint throughoutRenovated kitchen and bathUpdated fixtures and finishesClean, move-in ready conditionThis home offers the perfect blend

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
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  /26

  $1,700 per month

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • Condo for Rent

  21 N Braddock St Unit 4, Winchester, VA 22601

  Located in Historic Downtown Winchester, 1 block over from the Loudoun Street Mall. Restaurants, shops, transportation all within walking distance. Hardwood floors throughout historic property. 1 of 4 units total in building. Third Floor. No Pets/No Smoking. Kitchen features Stove, Microwave, Oven, Full size Fridge -AND a large walk-in pantry. Electronic keyed door entry, security

  21 N Braddock St Unit 4, Winchester, VA 22601
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  /61

  $525,000 Sold Jul 21, 2025

  • 3,440 Sq Ft
  • $153/SF
  • 17 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  3296 Apple Pie Ridge Rd, Winchester, VA 22603

  Tucked away on 1.66 scenic acres, this beautifully updated ranch-style home blends the serenity of country living with unbeatable convenience—just 10 minutes from downtown Winchester. Ideally located off Apple Pie Ridge Road, you’re within 15 minutes of the hospital and major highways, yet a world away from the hustle. Step inside and soak in over 3,400 sqft of freshly renovated living space,

  Christian Davis RE/MAX Executives

  3296 Apple Pie Ridge Rd, Winchester, VA 22603
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  /35

  Est $241,892 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
• 

  

  /33

  $408,000

  • 3 Beds
  • 2.5 Baths
  • 2,281 Sq Ft

  154 Solara Dr, Winchester, VA 22602

  PRICE ADJUSTMENT! PAID-OFF SOLAR PANELS MAKE THIS A STEAL!Charming Townhome with Solar Savings in a Prime Location!Welcome to this beautifully updated townhome nestled in a highly sought-after neighborhood just minutes from Rt 7! This move-in ready home boasts paid-off solar panels, keeping your electric bills at an incredible $20/month on average—a rare and valuable

  Kandi McKenzie Realty ONE Group Old Towne

  154 Solara Dr, Winchester, VA 22602
• 

  

  /18

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Condo for Rent

  11 Brookland Terrace, Winchester, VA 22602

  Do I need to say it? Location, location, location! This lovely 3rd-floor condo is nestled in a quiet neighborhood just minutes from downtown. A commuter's dream, located directly off I-81 and Rt. 7. Tons of extras - vaulted ceilings, walk-in closet in the master, new skylights, new HVAC, brand new stove, and hardwoods in the primary suite (will be installed prior to your move in). Whether you

  Sarah Abderrazzaq Realty ONE Group Old Towne

  11 Brookland Terrace, Winchester, VA 22602
• 

  

  /22

  $350,000 Sold Jul 21, 2025

  • 1,060 Sq Ft
  • $330/SF
  • 66 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  601 Fairview Ave, Winchester, VA 22601

  Fully Renovated Gem in the Heart of Winchester! Welcome to 601 Fairview Ave, where modern upgrades meet timeless charm! This beautifully remodeled 3-bedroom, 2-bathroom rambler offers the perfect blend of comfort and convenience in one of Winchester’s most desirable locations.Step inside to discover a brand-new kitchen featuring stylish finishes, sleek countertops, and modern

  Jorge Najarro Samson Properties

  601 Fairview Ave, Winchester, VA 22601
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  /29

  Est $253,747 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
• 

  

  /26

  $499,900

  • 6 Beds
  • 3 Baths
  • 3,900 Sq Ft

  811 Berryville Ave, Winchester, VA 22601

  DO YOU HAVE A LARGE FAMILY AND NEED YOUR OWN SPACE. HERE IS A 6 BEDROOMS 3 BATHROOMS WITH A IN-LAW SUITE. OVER 3900+ SQ. FT FINISHED. OFF STREET PARKING FOR 6 CARS. SHED AND STILL ROOM TO RELAX OUTBACK.

  Richard Kozlowski Long & Foster Real Estate, Inc.

  811 Berryville Ave, Winchester, VA 22601
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  /133

  $1,700 per month

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601

  COMPLETELY FURNISHED RENTALPerfect for traveling professionals or students.Furnished one bedroom located behind the beautiful Handley library. This quaint one bedroom apartment is on the 3rd floor of a historic home facing Fairmont Ave. It has terrific views and a spectacular view of fireworks on Apple Blossom, July 4th and New Years Eve. Beautiful details and wainscotting, built in

  342 Fairmont Ave Unit 5 FULLY FURNISHED RENTAL Retro Loves Company, Winchester, VA 22601
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  /28

  $488,990 Sold Jul 21, 2025

  • 1,953 Sq Ft
  • $250/SF
  • 114 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2025

  101 Monacan St, Winchester, VA 22602

  The Pine is a popular floorplan for all the right reasons! 4 bedrooms, 2.5 bathrooms, and a 2-car garage. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for seating, an impressive corner pantry, plenty of cabinet space and stainless-steel appliances that

  Tracy Jennings D R Horton Realty of Virginia LLC

  101 Monacan St, Winchester, VA 22602
• 

  

  /17

  Est $239,827 Not Listed For Sale

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

  157 Brookland Terrace Unit 10, Winchester, VA 22602

  157 Brookland Terrace Unit 10, Winchester, VA 22602
• 

  

  /56

  $549,900

  • 4 Beds
  • 3 Baths
  • 3,998 Sq Ft

  419 Westside Station Dr, Winchester, VA 22601

  “Classic and Contemporary” - Welcome to this beautifully maintained contemporary home nestled in one of Winchester's most hidden but premium neighborhoods. Offering nearly 4,000 square feet of finished living space across three thoughtfully designed levels, this 4-bedroom, 3-bath residence combines stylish updates with unique architectural details. Step inside to discover a warm and

  Mark Francis ICON Real Estate, LLC

  419 Westside Station Dr, Winchester, VA 22601
• 

  

  /16

  $1,550 per month

  • 2 Beds
  • 1 Bath
  • 999 Sq Ft
  • House for Rent

  1455 Senseny Rd, Winchester, VA 22602

  Cute cottage home on 1+ acres. Home has 2 bedrooms/1 bath and nice sized backyard. Hardwood floors throughout the home all on one level living. Cat(s) case-by-case-basis with non-refundable deposit. Positively no smoking anywhere on the property. All utilities to be connected and paid by tenant and tenant is responsible for their own snow removal. Tenants are to get renters insurance

  Rhonda Shade ERA Oakcrest Realty, Inc.

  1455 Senseny Rd, Winchester, VA 22602
• 

  

  /19

  $457,990 Sold Jul 21, 2025

  • 1,637 Sq Ft
  • $280/SF
  • 111 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  105 Monacan St, Winchester, VA 22602

  The Cabral is a thoughtfully designed, 1,665-square-foot open-concept two-story home, featuring three bedrooms, two and a half bathrooms, a versatile loft, and a two-car garage. As you step onto the welcoming front porch and enter the foyer, you’ll find a convenient coat closet and powder room. Moving further inside, the spacious living room seamlessly connects to the kitchen and casual dining

  Tracy Jennings D R Horton Realty of Virginia LLC

  105 Monacan St, Winchester, VA 22602
• 

  

  /18

  Est $247,655 Not Listed For Sale

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

  115 Brookland Terrace, Winchester, VA 22602

  115 Brookland Terrace, Winchester, VA 22602

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