Homes for Sale near The Independent School of Winchester

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  /71

  $1,250,000

  • Studio
  • 8,616 Sq Ft

  202 S Washington St, Winchester, VA 22601

  Back on the market due to NO fault of the Seller! Currently a single family home with a private “guest apartment”, but zoned multi-family with the potential for up to 4 units and potentially $4000.00+ in monthly rental income! Fantastic opportunity! The private guest suite currently has 2 bedrooms. The 3rd floor also has an additional 2 bedrooms, full bathroom and could laundry room that

  

  Lori Bales

  Keller Williams Realty

  (540) 917-5619

  202 S Washington St, Winchester, VA 22601
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• 

  

  

  /71

  $1,250,000

  • 7 Beds
  • 7 Baths
  • 8,616 Sq Ft

  202 S Washington St, Winchester, VA 22601

  Back on the market due to NO fault of the Seller! You have to see this $1M renovation by an architect out of NYC. Currently a single family home with a private “guest apartment”, but zoned multi-family with the potential for up to 4 units and potentially $4000.00+ in monthly rental income! Fantastic opportunity! The private guest suite currently has 2 bedrooms. The 3rd floor also has an

  

  Lori Bales

  Keller Williams Realty

  (540) 660-3543

  202 S Washington St, Winchester, VA 22601
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  /48

  $339,900

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft

  128 Fox Dr, Winchester, VA 22601

  Welcome to 128 Fox Dr — a spacious, move-in ready home nestled in the heart of Winchester, offering three levels spanning over 2,600 square feet of flexible living space, with 4 bedrooms, 3 bathrooms, and unbeatable convenience! This Cape Cod-style home features a thoughtful layout with at least one bedroom and a full bathroom on every level. Step into the main level to discover hardwood floors

  

  MJ Frazier

  Real Broker, LLC

  (540) 513-5877

  128 Fox Dr, Winchester, VA 22601
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  /104

  $869,500

  • 4 Beds
  • 4.5 Baths
  • 4,368 Sq Ft

  1517 Brookdale Ct, Winchester, VA 22601

  Welcome to this stunning and spacious brick Colonial, perfectly situated on one of the best lots in Morlyn Hills, nestled on a quiet cul-de-sac and overlooking a 45-acre protected wetland preserve. Impeccably maintained and offering over 6,500 + of finished square feet of elegant living space, this home features 4 bedrooms, 4.5 baths, and an impressive array of upgrades throughout.From the moment

  

  Brock Harris

  Samson Properties

  (540) 596-5570

  1517 Brookdale Ct, Winchester, VA 22601
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  /2

  $695,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 3,108 Sq Ft

  1950 Melvor Ln, Winchester, VA 22601

  Coming Soon Offered to Investor - Currently Rented NO DRIVEBY SHOWINGS

  

  Kim Kroner

  Washington Dulles Real Estate Group

  (540) 453-8579

  1950 Melvor Ln, Winchester, VA 22601
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  /45

  $500,000

  • 4 Beds
  • 3 Baths
  • 1,881 Sq Ft

  331 Ridge Ave, Winchester, VA 22601

  Assessed at $491K and only asking $500K. One level living on a beautiful corner lot in Whittier Acres - a very desirable neighborhood in Winchester City! Take advantage of the convenience of everything Winchester in this location - Winchester Medical Center, Downtown Winchester, the Museum of the Shenandoah Valley, and all of the popular restaurants. With 3 bedrooms and 2 bathrooms on the

  

  Lori Bales

  Keller Williams Realty

  (540) 253-4577

  331 Ridge Ave, Winchester, VA 22601
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  /23

  $168,000

  • Land
  • 10 Acres
  • $16,800 per Acre

  0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602

  Enjoy rural living and fun on this building lot in the Long Ridge Estates community. This prime building lot is located off of Gough Road in the High View Manor area of the county. This parcel has a septic certification letter on record with the county health department for a four-bedroom septic system. Access is secured via a 50 ft deeded access easement, which has already been installed and

  Chad Pangle Whitetail Properties Real Estate

  0 Gough Rd Unit LotWP002 20612085, Winchester, VA 22602
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  /41

  $489,000

  • 3 Beds
  • 2 Baths
  • 1,744 Sq Ft

  327 Bryarly Rd, Winchester, VA 22603

  Charming Countryside Cape Cod on a Meticulously Maintained 1.25 acres! Welcome to 327 Bryarly Drive, Winchester, VA 22603 – a beautifully updated Cape Cod-style home nestled on a serene and private half-acre lot. Originally built in 1941, this residence exudes countryside charm and character, while offering numerous modern upgrades.Step inside to discover 3 spacious bedrooms and 2 full baths,

  Lisa Behr Coldwell Banker Premier

  327 Bryarly Rd, Winchester, VA 22603
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  /49

  $649,000

  • 4 Beds
  • 3 Baths
  • 3,462 Sq Ft

  101 Morgan St, Winchester, VA 22601

  Downtown Winchester - 2 blocks from the walking mall with in-law suite or lower level rental potential! From the moment you arrive, you’ll be drawn in by this home’s timeless symmetry, classic brick exterior, and welcoming front porch. Thoughtful landscaping and charming details set the stage for what’s inside. With 5 bedrooms and 3 full baths, there’s plenty of space for everyone. The foyer

  Jeanne Mezzatesta Colony Realty

  101 Morgan St, Winchester, VA 22601
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  /56

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 2,581 Sq Ft

  1080 Old Bethel Church Rd, Winchester, VA 22603

  Turnkey Homestead on 5+ Acres | Updated 4BR Home with Farm InfrastructureWelcome to this versatile and well-maintained property located in the pastoral countryside of Frederick County, VA. Situated on 5.07 acres, this 4-bedroom, 3.5-bath home offers modern updates, flexible living spaces, and a fully functional homestead setup—ideal for those seeking rural charm with commuter convenience.The main

  Samantha Armel EXP Realty, LLC

  1080 Old Bethel Church Rd, Winchester, VA 22603
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  /64

  $520,000

  • 4 Beds
  • 4 Baths
  • 1,830 Sq Ft

  1104 Milroy Ct, Winchester, VA 22601

  Step into this beautifully cared-for home featuring gleaming hardwood floors throughout and a spacious, inviting layout. The large kitchen offers plenty of room for meal prep and flows effortlessly into the dining and living rooms — perfect for family gatherings and entertaining.Enjoy the convenience of a sizable laundry room equipped with a front-loading washer and dryer. The finished basement

  Hailey Mooney Real Broker, LLC

  1104 Milroy Ct, Winchester, VA 22601
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  /68

  $700,000

  • 3 Beds
  • 3 Baths
  • 1,664 Sq Ft

  516 Merrimans Ln, Winchester, VA 22601

  Amazing Opportunity--First time on the market, this mid-century Ranch comes with updated bathrooms and custom kitchen. The 1.4 acre property includes an in-ground pool and guest house with full bath and kitchenette. Densely landscaped property provides almost complete privacy on one of the few remaining spacious lots inside the city. A large Lanai complements the property for entertaining or

  Dallas Croft Samson Properties

  516 Merrimans Ln, Winchester, VA 22601
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  /25

  $475,000

  • 4 Beds
  • 2 Baths
  • 1,092 Sq Ft

  1709 Reaves St, Winchester, VA 22601

  Please take off shoes and give feedback. Step into this beautifully cared-for home featuring new roof (2023) New HVAC System (2024) new LVP floors throughout the basement a spacious, inviting layout. The large kitchen offers plenty of room for meal prep and flows effortlessly into the dining and living rooms — perfect for family gatherings and entertaining. The finished basement boasts a

  Alexandra Brown Berkshire Hathaway HomeServices PenFed Realty

  1709 Reaves St, Winchester, VA 22601
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  /50

  $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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  /31

  $625,000

  • 3 Beds
  • 3 Baths
  • 3,078 Sq Ft

  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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  /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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  /28

  $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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  /36

  $354,900

  • 2 Beds
  • 2.5 Baths
  • 1,238 Sq Ft

  1312 S Kent St, Winchester, VA 22601

  Welcome to this beautifully maintained townhouse featuring 2 spacious bedrooms and 2.5 baths. Enjoy the convenience of both driveway parking and additional parking lot spaces. The modern kitchen boasts quartz countertops, a stylish backsplash, electric cooking, bamboo flooring, a pantry, and a reverse osmosis water system—perfect for any home chef. Located in the heart of downtown Winchester,

  Sheila Pack RE/MAX Roots

  1312 S Kent St, Winchester, VA 22601
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  /50

  $470,000

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft

  350 Lanny Dr, Winchester, VA 22601

  This beautifully remodeled 3-bedroom, 2-bathroom all-brick rancher is perfectly situated in the heart of Winchester, providing easy access to schools, downtown, Winchester Medical Center, shopping, dining, entertainment, and parks. With its thoughtful remodel, this home blends timeless charm with modern updates. The eat-in kitchen boasts stainless steel appliances (2023), making it perfect for

  Sheila Pack RE/MAX Roots

  350 Lanny Dr, Winchester, VA 22601
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  /53

  $500,000

  • 4 Beds
  • 2 Baths
  • 2,012 Sq Ft

  669 Dicks Hollow Rd, Winchester, VA 22603

  Welcome to this spacious farmhouse on FIVE acres! NEW TWO ZONE HEAT AND AC BEING INSTALLED ON TUESDAY THE 17TH! NEW hot water heater! NEWER windows throughout. Metal roof - large detached two car garage with large work area. Pole barn and garden shed! Apple trees, peach tree - 15 minutes to town!

  Barbera Clausen EXP Realty, LLC

  669 Dicks Hollow Rd, Winchester, VA 22603
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  /47

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 1,865 Sq Ft

  336 Miller St, Winchester, VA 22601

  This beautiful cottage, nestled on the very sought after Miller St, supplies the utmost convenience for what Winchester has to offer. From walking distance to eateries and Old Town entertainment, a quick drive to supermarkets all around and Handley High School just one street away! Supplying 3 bedrooms 2 1/2 bathrooms across three levels you can appreciate the character of an older home with

  Julie Teets Long & Foster Real Estate, Inc.

  336 Miller St, Winchester, VA 22601
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  /41

  $459,000

  • 5 Beds
  • 2 Baths
  • 2,364 Sq Ft

  707 S Braddock St, Winchester, VA 22601

  Don’t miss your chance to own a Winchester classic in the heart of downtown! This beautifully renovated home boasts a brand-new kitchen with granite counters, stainless steel appliances, and white shaker cabinets. Enjoy modern bathrooms, stylish LVP flooring, and fresh paint throughout. The open-concept layout offers great flow for entertaining. Upstairs features spacious bedrooms and access to a

  Tolga Alper Real Broker, LLC

  707 S Braddock St, Winchester, VA 22601
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  /25

  $519,900

  • 4 Beds
  • 3 Baths
  • 2,312 Sq Ft

  609 Quartzite Cir, Winchester, VA 22601

  Welcome to 609 Quartzite Circle, a meticulously maintained 4-bedroom, 3-bathroom home nestled in the desirable Limestone Terrace subdivision of Winchester, VA. This spacious residence offers 2,312 square feet of comfortable living space, featuring an open floor plan with cathedral ceilings, recessed lighting, and gleaming hardwood floors that enhance its bright and inviting atmosphere.

  Berta Vasquez Samson Properties

  609 Quartzite Cir, Winchester, VA 22601
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  /36

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,328 Sq Ft

  224 Lauck Dr, Winchester, VA 22603

  Custom Home in Historic Star Fort: Timeless Charm Meets modern Comfort for Discerning Buyers.This impeccably designed 3-bedroom, 2.5-bath home is a harmonious blend of classic elegance and contemporary convenience. Boasting cherry wood flooring throughout the main living areas, high-quality tile in the kitchen and bathrooms, and carpeted bedrooms, this home is as stylish as it is practical. Be

  Gidget Smallwood Coldwell Banker Premier

  224 Lauck Dr, Winchester, VA 22603
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  /73

  $525,000

  • 3 Beds
  • 1.5 Baths
  • 2,964 Sq Ft

  306 Burnt Church Rd, Winchester, VA 22603

  Welcome to this charming Circa 1801-Farmette, nestled on approximately 7.5 unrestricted acres just outside the City of Winchester. This property offers the perfect blend of historic character and rural tranquility, with convenient access to shopping, dining, and major commuter routes, including Rt. 37 and I-81. Enjoy the open space for gardening, raising poultry, or embracing a country

  Sue Goodwin Long & Foster Real Estate, Inc.

  306 Burnt Church Rd, Winchester, VA 22603
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  /26

  $535,000

  • 3 Beds
  • 3 Baths
  • 1,809 Sq Ft

  257 Jefferson St, Winchester, VA 22601

  Jonathan Minerick Homecoin.com

  257 Jefferson St, Winchester, VA 22601
• 

  /2

  $399,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,394 Sq Ft

  Bedford II, Winchester, VA 22601

  Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  DRB Homes

  Bedford II, Winchester, VA 22601
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  /2

  $452,539 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  Homesite 20 Monteith Dr, Winchester, VA 22601

  End Of Row Townhome With 1 Car Garage & Gourmet Kitchen! This home has a Gourmet Kitchen: cooktop with chimney style hood, wall microwave, wall oven, upgraded gourmet Energy Star stainless steel appliances, Refrigerator is a French 2 door style, the kitchen island is extended to comfortably seat 4, and a box bay window in the rear of the home for extra lighting located in the kitchen. You are

  DRB Homes

  Bedford II, Winchester, VA 22601
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  /2

  $429,340 New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,630 Sq Ft

  Homesite 114 Monteith Dr, Winchester, VA 22601

  3 Level Townhome With Over 1,600 Finished Sq Ft & 1 Car Garage! Bedford II, 3 level townhome features a partial stone front with 1 car garage. This home features 3 Bedrooms and 3.5 Baths. It is fully finished top to bottom. The front door leads directly into the spacious lower level including 9 ft. ceilings, foyer with a double coat closet, access to the garage with a garage door opener.

  DRB Homes

  Bedford II, Winchester, VA 22601
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  /9

  $375,000 Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,584 Sq Ft

  115 Tanglewood Ln, Winchester, VA 22602

  Welcome to 115 Tanglewood Lane - Located on a quiet, no-through street in one of Winchester’s incredible 55+ communities, this charming home offers the perfect blend of comfort, convenience, and low-maintenance living. Just minutes from historic downtown Winchester and walking distance to Creekside Station, you'll love having shops, restaurants, and local businesses right at your fingertips.Step

  Tiffany Hunter ERA Oakcrest Realty, Inc.

  115 Tanglewood Ln, Winchester, VA 22602
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  /29

  $245,000

  • 2 Beds
  • 1.5 Baths
  • 1,024 Sq Ft

  2635 Limestone Ct, Winchester, VA 22601

  Move right in with no worries! adorable townhome with granite counters plus Lots of news: April 2023 AC replaced inside and outside, Gas Furnace replaced 2022,Roof replaced 2023,Fence installed 2024, New carpet 2025, newer LVP on main level Appliances a couple years old. 2 bedrooms, 1.5 baths ready for a new owner. Winchester city location near bus routes. Looking for investment property this

  Deborah Matthews ERA Oakcrest Realty, Inc.

  2635 Limestone Ct, Winchester, VA 22601
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  /27

  $315,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft

  412 Fairview Ave, Winchester, VA 22601

  Welcome to 412 Fairview Ave. A ranch-style home with a full basement.This house features hardwood floors, a gas fireplace in the living room, and a central vacuum system.On the main level, you'll find three bedrooms and two full bathrooms. The kitchen comes fully equipped with a stove, refrigerator, microwave, and dishwasher, all of which convey along with the window treatments. Enjoy the

  Junue Hernandez Rojas Long & Foster Real Estate, Inc.

  412 Fairview Ave, Winchester, VA 22601
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  /74

  $1,129,000

  • 8 Beds
  • 5.5 Baths
  • 6,174 Sq Ft

  1020 Breckinridge Ln, Winchester, VA 22601

  Exceptional 8 bedroom, 5.5 bath home located in the city of Winchester, offering space, luxury, and thoughtful updates throughout. The 3-car side-entry garage includes a convenient half bath. Enjoy outdoor living with covered front and side porches, a spacious covered rear deck, and a lawn sprinkler system in the front yard. The gourmet kitchen featuring Jenn-Air appliances, upgraded cherry

  Sheila Pack RE/MAX Roots

  1020 Breckinridge Ln, Winchester, VA 22601
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  /12

  $135,000

  • 3 Beds
  • 1 Bath

  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 1,600

  Kevin Rodriguez Weichert, REALTORS

  381 National Ave, Winchester, VA 22601
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  /8

  $175,000

  • Land
  • 0.36 Acre
  • $486,111 per Acre

  2812 Saratoga Dr, Winchester, VA 22601

  A rare find and jewel of a lot! .36 acres in the perfect location on the south side of Winchester city limits. A short walk to Creekside Station with shopping and dining and the Kernstown Battlefield. Enjoy the quiet street with sidewalks and the bonus...water/sewer taps have been paid! Well maintained homes on either side make this a strong investment for a builder or create your custom

  Dave Spence RE/MAX Roots

  2812 Saratoga Dr, Winchester, VA 22601
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  /30

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,431 Sq Ft

  1826 Kershaw Ln, Winchester, VA 22601

  This charming one-level home is perfectly situated in one of Winchester's desirable 55+ senior communities, Willow Lawn Cottages. Great home....first time on the market,featuring two spacious bedrooms, two full bathrooms, hardwood floors & vaulted ceilings. The open and inviting floor plan will make your new home ideal for both daily living and entertaining. The large primary suite offers

  Jeff Webber Long & Foster Real Estate, Inc.

  1826 Kershaw Ln, Winchester, VA 22601
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  /36

  $299,900

  • 2 Beds
  • 1 Bath
  • 813 Sq Ft

  516 Hollingsworth Dr, Winchester, VA 22601

  Location & Lifestyle Highlights for 516 Hollingsworth Drive, Winchester, VANestled in one of Winchester’s most sought-after neighborhoods, 516 Hollingsworth Drive offers more than just a beautiful home; it offers a lifestyle. Enjoy direct access to scenic walking and biking trails, including the popular Green Circle Trail, which winds through town and links several parks and historic districts.

  Chris Zarou Pearson Smith Realty, LLC

  516 Hollingsworth Dr, Winchester, VA 22601
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  /24

  $245,000

  • 2 Beds
  • 2.5 Baths
  • 1,080 Sq Ft

  208 Kimberly Way, Winchester, VA 22601

  Just Listed in Winchester, VA!A beautifully maintained 2-bedroom, 2.5-bath townhome. Offering 1,080 square feet of comfortable living space. This property combines small-town charm with functional features that make everyday living a breeze. Inside, a bright and airy living room and kitchen welcomes you with large windows and an exit door to the deck that allow natural light to pour in, creating

  Janet Smith NextHome Realty Select

  208 Kimberly Way, Winchester, VA 22601
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  /28

  $349,900

  • 3 Beds
  • 1 Bath
  • 1,376 Sq Ft

  230 Allison Ave, Winchester, VA 22601

  Welcome to 230 Allison Avenue, a recently renovated 3-bedroom, 1-bath home on a spacious 0.23-acre lot in Winchester. Ideally located just 1 mile from Winchester Medical Center and only minutes to Walmart Supercenter, shops, restaurants, and vibrant downtown Winchester, this home offers both convenience and charm. Step inside to discover a thoughtfully updated interior featuring luxury vinyl

  Jon Fleming Weichert Realtors - Blue Ribbon

  230 Allison Ave, Winchester, VA 22601
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  /12

  $299,000

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  Welcome home to 711 E. Cork Street! Centrally located in Winchester, VA. Enjoy the ease of access to downtown Winchester, Jim Barnett Park, shopping, and commuter routes. This 2 bedroom 1 1/2 bath detached home with brand new exterior update(new vinyl siding). Deeded right away provides access to rear of the property. Call today for your private showing!

  Jim Stafford ERA Oakcrest Realty, Inc.

  711 E Cork St, Winchester, VA 22601

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