Winchester, VA Homes for Sale under $300,000

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  /45

  $260,000

  • 2 Beds
  • 1 Bath
  • 997 Sq Ft

  108 Martin Dr, Winchester, VA 22602

  Attention investors! Charming brick rambler situated on a spacious corner lot, just minutes from Route 7 and I-81—an ideal location for commuters. The property offers a driveway and a carport, perfect for convenient parking or doubling as a shaded outdoor space for entertaining, along with generous storage space. Inside, you’ll find an open-concept living room and eat-in kitchen with large

  Heloisa Amar Samson Properties

  108 Martin Dr, Winchester, VA 22602
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  /17

  $289,000

  $6K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  1314 S Braddock St, Winchester, VA 22601

  1314 S Braddock St is a one-story Winchester single-family home with a functional single-level layout. The kitchen is equipped with stainless steel appliances for everyday cooking and cleanup. The bathroom includes a tub and shower for daily use, and a dedicated laundry area with a stacked washer and dryer keeps utility tasks out of the main living space. Multiple bedrooms provide flexible room

  Jacqueline Moore Open Door Brokerage, LLC

  1314 S Braddock St, Winchester, VA 22601
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  /51

  $224,900

  $34K PRICE DROP

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

  8 Brookland Ct Unit 8, Winchester, VA 22602

  2 Bed, 2 bath condominium. New appliances, including water heater and heat pump. Gas fireplace, open concept with separate dining room. Patio/ porch with french doors and skylights in living room allow tons of natural light. Primary suite includes walk-in closet. Conveniently located off rt 7 and 81.

  Vicki Broy RE/MAX Roots

  8 Brookland Ct Unit 8, Winchester, VA 22602
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  /19

  $141,500

  • Land
  • 11.1 Acres
  • $12,748 per Acre

  0 Hodges Lot 14 Ln, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Hodges Lot 14 Ln, Winchester, VA 22603
• 

  

  

  /23

  $127,750

  • Land
  • 8.11 Acres
  • $15,752 per Acre

  0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602

  Rare opportunity to own three adjoining fully wooded parcels in the quiet and peaceful Shawneeland community. Numerous residential and recreational possibilities exist with ownership of these tracts. Located just a few miles west of Winchester in the Rosenberger area of the county. Access is secured via extensive road frontage on paved Wolf Spring Trail. Utilities are close by making for easy and

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Wolf Spring Trail Unit VAFV2043748, Winchester, VA 22602
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  /2

  $175,000

  $25K PRICE DROP

  • 1 Bed
  • 1 Bath

  5737 N Frederick Pike, Winchester, VA 22603

  4.2 Acres, Sold As-Is, Flat Usable Lot, Partially Wooded, Well and Septic Exists, Just Outside of Winchester VA, No HOA, Unrestricted. Well and septic on property . Well is located in back of old mobile home at water pump. Septic located further back behind old mobile home marked wirh red sparay paint. Health department docs are in bright. Neither house nor mobile home livable.Sold As Is With

  Tracy Link Coldwell Banker Premier

  5737 N Frederick Pike, Winchester, VA 22603
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  /39

  $290,000

  $25K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,170 Sq Ft

  126 Marple Rd, Winchester, VA 22603

  Charming Cape Cod-style home located at 126 Marple Rd in the desirable north end of Winchester! This well-maintained 3-bedroom, 1.5-bath home offers timeless character, functional living space, and a convenient commuter-friendly location. The main level features a bedroom with a 1/2 bath, a living room, a dining room, and a kitchen. Upstairs, you’ll find additional bedrooms with a shared

  RoxAnn Grimes RE/MAX Roots

  126 Marple Rd, Winchester, VA 22603
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  /5

  $10,000

  • Land
  • 0 Sq Ft

  Lot 13 Tomahawk Trai 0, Winchester, VA 22602

  Welcome to Shawneeland! This mountain community is tucked away in a rural setting and a short distance to shopping, restaurants and Winchester's Historic Downtown. Utilize this 0.48 acre lot as a potential building lot, recreational space or enjoy the amenities such as Lake Cherokee with a beach area, fishing and picnic areas. Purchaser to verify location of boundary lines.

  Kim Hurst MarketPlace REALTY

  Lot 13 Tomahawk Trai 0, Winchester, VA 22602
• 

  /2

  $4,500

  $1K PRICE INCREASE

  • Land
  • 10,890 Sq Ft
  • $18,000 per Acre

  107 Fox Trail, Winchester, VA 22602

  Lot 109 is also available for sale but not listed.

  Babak Taghavi Venture Realty

  107 Fox Trail, Winchester, VA 22602
• 

  

  /24

  $25,000

  • Land
  • 1.43 Acres
  • $17,483 per Acre

  LOT 5A Fox Trail, Winchester, VA 22602

  Beautiful building lot located in Mountain Falls Park – Wilde Acres. This is the last lot on the right on Fox Trail, offering excellent privacy and seclusion. The property backs to permanent open space, providing a peaceful setting with mountain views and abundant wildlife. Approved for a 3-bedroom septic system with a certification letter on file. A current survey is also available. This is an

  Nadeem Helfer Samson Properties

  LOT 5A Fox Trail, Winchester, VA 22602
• 

  

  /23

  $49,500

  • Land
  • 1.45 Acres
  • $34,138 per Acre

  0 Tomahawk Trail Unit VAFV2043562, Winchester, VA 22602

  Don't miss this rare opportunity in Shawneeland! This beautiful L-shaped wooded hillside lot offers nearly 1.5 acres of mountain serenity and flexibility for your future home.Nestle your residence along Willow Trail, surrounded by mature trees and natural beauty, or build near the top of the property on Tomahawk Trail, where you'll enjoy breathtaking views of the Shenandoah Valley and the

  Rebecca McTavish Long & Foster Real Estate, Inc.

  0 Tomahawk Trail Unit VAFV2043562, Winchester, VA 22602
• 

  /2

  $89,900

  • Land
  • 20.33 Acres
  • $4,422 per Acre

  0 Outback Trail Unit 25B1, Winchester, VA 22602

  Rugged piece of the Great North Mountain which is quite near the WV & VA state line and there is a small dwelling. NO Septic & NO Water. Wear rugged footwear and operate a rugged 4X4 or All Wheel Drive vehicle. Listing Agent will have to open the access gate... Should you access this area be forewarned without Listing Agent, you are at your risk. Picture was taken quite close but you get the

  John Holsinger JOHN S HOLSINGER REAL ESTATE BROKER LLC

  0 Outback Trail Unit 25B1, Winchester, VA 22602
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  /5

  $4,000

  • Land
  • 13,503 Sq Ft
  • $12,903 per Acre

  0 Fox Trail Unit VAFV2042734, Winchester, VA 22602

  .31 acre wooded lot on an incline. No septic or well tests have been done. Seller doesn't know if it's buildable. Drive by any time to show.

  Tanner Pack RE/MAX Roots

  0 Fox Trail Unit VAFV2042734, Winchester, VA 22602
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  /9

  $17,000

  • Land
  • 21,780 Sq Ft
  • $34,000 per Acre

  Lot 111 Cub Trail, Winchester, VA 22602

  Tired of the bustle of city life? Visit Shawneeland in northwestern Frederick County, Virginia. Visit for a day and stay for a lifetime. This mountaintop lot on the western slope is just the place to build a home. Enjoy Shawneeland's amenities: a spring-fed lake perfect for swimming and fishing, a playground for the children, and hiking trails for the entire family.Love the country but want

  Rebecca McTavish Long & Foster Real Estate, Inc.

  Lot 111 Cub Trail, Winchester, VA 22602
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  /8

  $289,900

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

  2640 Limestone Ct, Winchester, VA 22601

  Nestled in the charming City of Winchester, this exquisite end-of-row townhouse has undergone a remarkable transformation, with major renovations completed in 2026 that elevate it to a new standard of luxury living. The timeless Colonial architectural style, complemented by a classic brick exterior, exudes elegance and warmth, inviting you to experience a lifestyle of comfort and sophistication.

  Meridee Powars Link Realty Services LLC

  2640 Limestone Ct, Winchester, VA 22601
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  /21

  $262,000

  $7K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  321 N Kent St, Winchester, VA 22601

  Attention investors...24 month lease in place and new HVAC! Wonderful opportunity to own in downtown Winchester! Walking distance to the Old Town Mall restaurants, shopping, the library and more. Easy access to Rt. 7 and 81. The main level has a nice open floor plan, consisting of kitchen, dining and living areas. The main level also features a half bath and bonus room, perfect for an office or

  Amy Capitano MarketPlace REALTY

  321 N Kent St, Winchester, VA 22601
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  /57

  $115,000

  • 528 Sq Ft

  403 Stag Trail, Winchester, VA 22602

  Ever dreamed of owning your own private A-frame cabin in the woods? Whether you're searching for the perfect weekend retreat, a unique short-term rental opportunity, or a peaceful getaway to enjoy with family, friends, or clients, this charming mountain cabin is full of potential. Tucked away in a quiet, wooded setting with easy year-round access, this hidden gem offers the perfect balance of

  Chris Roszko Colony Realty

  403 Stag Trail, Winchester, VA 22602
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  /9

  $17,000

  • Land
  • 18,295 Sq Ft
  • $40,476 per Acre

  Lot 76 Bear Trail, Winchester, VA 22602

  Looking for a lot in a quiet, rural development where you can enjoy the beauty of nature, listen to the birds, and view an occasional wild turkey or deer? This undeveloped lot in Shawneeland may be just the place for you. With its spring-fed lake, great for fishing or swimming, and mountain trails, Shawneeland is the perfect place to build a getaway retreat or a full-time residence. Located

  Rebecca McTavish Long & Foster Real Estate, Inc.

  Lot 76 Bear Trail, Winchester, VA 22602
• 

  

  /40

  $289,000

  $11K PRICE DROP

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

  110 Brookland Ct Unit 10, Winchester, VA 22602

  Welcome home to this one-of-a-kind, fully renovated penthouse condo that has been transformed right down to the studs! Offering luxury finishes rarely found at this price point, this stunning residence is unlike anything else available in Frederick County under $300,000.Every detail has been thoughtfully updated, including a new gas furnace, new HVAC system, new flooring throughout,

  Traci Shoberg Samson Properties

  110 Brookland Ct Unit 10, Winchester, VA 22602
• 

  

  /20

  $154,650

  • Land
  • 12.9 Acres
  • $11,988 per Acre

  0 Hodges Lot 11 Ln, Winchester, VA 22603

  Own a piece of the beautiful Back Creek Heights community in Cross Junction. Located just minutes north of Winchester in the Dehaven part of the county. Access is secured via road frontage on Hodges Lane. Experience exciting hunting as many types of wildlife call this property home including deer, turkey, and many small game species. This tract is currently being used for recreation and hunting.

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Hodges Lot 11 Ln, Winchester, VA 22603
• 

  

  /13

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 1,161 Sq Ft

  519 Virginia Ave, Winchester, VA 22601

  This charming house has great potential. It is located directly across from the Virginia Avenue School campus, close to downtown Winchester. The exterior was recently painted and a new roof installed in 2025. This home would be great "Handyman's Delight" as the interior needs quite a bit of attention as the bath and kitchen are outdated. The 100 amp electric service was updated in 1993, water

  Katherine Solenberger Colony Realty

  519 Virginia Ave, Winchester, VA 22601
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  /15

  $289,000

  $41K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  211 Fair Ln, Winchester, VA 22603

  Beautifully newly remodeled ranch-style home set on a spacious 0.62-acre flat lot. This move-in ready residence features a fully updated interior with a modern kitchen complete with granite countertops, brand-new stainless steel appliances, and all-new cabinetry. The home showcases rich hardwood flooring throughout and has been thoughtfully upgraded with new windows and a newer metal roof for

  Kenny Ritenour Samson Properties

  211 Fair Ln, Winchester, VA 22603
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  /9

  $9,500

  • Land
  • 23,958 Sq Ft
  • $17,273 per Acre

  LOTS 8 & 9 Elk Trail, Winchester, VA 22602

  Great opportunity to own two beautiful wooded lots full of mature trees and plenty of privacy! These adjoining parcels offer a wonderful chance to connect with nature and enjoy peaceful surroundings. Located just about 30 minutes from downtown Winchester, you get the perfect mix of country calm and town convenience. Whether you’re thinking about outdoor fun, future plans, or simply an investment,

  Kristin Crosby Samson Properties

  LOTS 8 & 9 Elk Trail, Winchester, VA 22602
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  /2

  $299,000

  $66K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,678 Sq Ft

  719 National Ave, Winchester, VA 22601

  Priced to sell! A true Federal‑style gem, this solid brick home offers the chance to restore a piece of architectural history. Rich with original craftsmanship, it features high ceilings, original hardwood floors, solid wood doors and trim, and a beautiful covered front porch—timeless details that showcase the home’s enduring character. Designed with good bones and a layout that adapts to many

  Windy Harris Hunt Country Sotheby's International Realty

  719 National Ave, Winchester, VA 22601
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  /38

  $139,900

  • Land
  • 20 Acres
  • $6,995 per Acre

  TWO LOTS ON Siler Rd, Winchester, VA 22603

  In the Gainesboro area of Frederick County, VA, offered here are (2) 10 acre lots with unique characteristics. The land is within the Rhine Forest Estates "subdivision" with NO COVENANTS or RESTRICTIONS. First thought is for recreation. The first lot borders Siler Road (hard surfaced state road) and also extends over Bucksaw Ln, running to the banks of Isaac Creek. The 2nd lot is right next door,

  Edward Beightol Cedar Creek Real Estate

  TWO LOTS ON Siler Rd, Winchester, VA 22603
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  /28

  $244,900

  $10K PRICE DROP

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

  1366 Brookland Terrace Unit 6, Winchester, VA 22602

  Discover the charm of Parkplace Condominiums, where comfort meets convenience in a vibrant community. This inviting 2-bedroom, 2-bathroom unit features modern stainless steel appliances, including a built-in microwave, dishwasher, and electric oven, making meal prep a delight. Enjoy the ease of in-unit laundry with washer and dryer hookups, ensuring your daily routines are seamless. Nestled in a

  Jeffrey Konrady Realty ONE Group Old Towne

  1366 Brookland Terrace Unit 6, Winchester, VA 22602
• 

  

  /54

  $295,000

  $20K PRICE INCREASE

  • 2 Beds
  • 2.5 Baths
  • 2,148 Sq Ft

  159 Aspen Trail, Winchester, VA 22602

  **Investor & Fixer-Upper Special Endless Potential on Nearly 1 Acre!** Calling all visionaries, weekend warriors, and Airbnb hosts! This secluded retreat in Shawneeland is your chance to create the mountain getaway, rental, or private homestead you've been dreaming of customized entirely to your style. Offering an estimated 2,000+ sq ft of finished living space with the potential for over 2,400

  Kimberly Baggett EXP Realty, LLC

  159 Aspen Trail, Winchester, VA 22602
• 

  

  /37

  $280,000

  • 3 Beds
  • 1 Bath
  • 1,058 Sq Ft

  2810 N Frederick Pike, Winchester, VA 22603

  Recently renovated and move-in ready! This updated 3-bedroom, 1-bath home offers the perfect combination of modern finishes and worry-free living with major upgrades already completed. Enjoy peace of mind with a new roof, new windows, new siding, and a brand-new HVAC system, providing comfort and energy efficiency for years to come. Inside, you'll find stylish luxury vinyl plank (LVP) flooring

  Jonathan Fleming Weichert Realtors - Blue Ribbon

  2810 N Frederick Pike, Winchester, VA 22603
• 

  /2

  $39,900

  $10K PRICE INCREASE

  • Land
  • 19,602 Sq Ft
  • $88,667 per Acre

  Lot 205 Rockwood Trail, Winchester, VA 22602

  Offers the best views of the valley. Beautiful lot (almost 1/2 acre) with valley views of Shenandoah waiting for your clients to build your new home on or buy and hold. Perfect for those who want privacy and view. Great for primary home or weekend retreat. Cert Letter 3 bedroom perk..

  Jim Thomson Realty ONE Group Old Towne

  Lot 205 Rockwood Trail, Winchester, VA 22602
• 

  

  /25

  $250,000

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Welcome to 1125 Conway Ave, a charming bungalow in Winchester City that's move-in ready and full of character! This cozy 2-bedroom, 1-bath home features beautiful hardwood floors and numerous recent updates, including a new roof, fresh interior paint, kitchen remodel, hallway and bathroom flooring, and a new stainless steel refrigerator. The deck has also been restored, providing a great spot to

  Curtis Siever NextHome Realty Select

  1125 Conway St, Winchester, VA 22601
• 

  

  /13

  $300,000

  • Land
  • 20.51 Acres
  • $14,627 per Acre

  0 Brush Creek Rd Unit VAFV2043700, Winchester, VA 22603

  Discover the possibilities with this beautiful 20.2-acre property offering the perfect blend of privacy, natural beauty, and opportunity. Featuring a mix of mature woods and a spacious open field, this versatile parcel is ideal for outdoor recreation, hunting, or creating your own private retreat.With a recorded dominant easement for ingress and egress, you’ll enjoy convenient access

  Caitlyn Sions Realty ONE Group Old Towne

  0 Brush Creek Rd Unit VAFV2043700, Winchester, VA 22603
• 

  /2

  $199,900

  $50K PRICE DROP

  • Land
  • 5 Acres
  • $39,980 per Acre

  181 Oak Dr, Winchester, VA 22603

  Build Your Vision at the End of the Lane Discover a rare opportunity to create a custom estate in an established community of luxury homes (up to 4,000 sq. ft.). Located at the quiet end of the street, this lot offers the perfect blend of privacy and prestige. Enjoy the peace of a secluded setting without sacrificing convenience—you are minutes from town with effortless access to Route 50. With a

  Jim Thomson Realty ONE Group Old Towne

  181 Oak Dr, Winchester, VA 22603
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  /16

  $229,900

  $20K PRICE DROP

  • Land
  • 1 Acre
  • $229,900 per Acre

  Lot 36 Lake Serene Dr, Winchester, VA 22603

  Lake Serene Winchester Va. Don’t miss this rare opportunity to own the last available build-able lot in peaceful, secluded Lake Serene, a private, established lake community quietly tucked away, yet only 10 minutes from Old Town Winchester! You will never find an opportunity like this to enjoy the peace and tranquility of waterfront living with the added bonus of being only a few miles from

  Mark Jenkins Rappahannock Real Estate, LLC.

  Lot 36 Lake Serene Dr, Winchester, VA 22603
• 

  /2

  $8,500

  • Land
  • 0 Sq Ft

  0 0 Unit VAFV2036674, Winchester, VA 22602

  Kelly Hayes Samson Properties

  0 0 Unit VAFV2036674, Winchester, VA 22602
• 

  

  /26

  $295,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft

  110 Duwamish Trail, Winchester, VA 22602

  Charming and Move-In Ready Ranch in a Peaceful Setting!Welcome home to this beautifully refreshed single-level ranch nestled on a spacious, tree-lined lot. This inviting home features a bright and functional layout with updated finishes throughout. The kitchen offers grey cabinetry, granite countertops, and stainless steel appliances, creating a clean and modern space perfect for everyday

  Tina Jacobin Main Street Realty

  110 Duwamish Trail, Winchester, VA 22602
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  /27

  $249,900

  $5K PRICE DROP

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

  8 Brookland Ct Unit 8, Winchester, VA 22602

  Fully Renovated 2026 | Turnkey 2BR/2BA Condo in Park PlaceWelcome to 136-8 Brookland Ct—where style, comfort, and convenience come together. This stunning second-floor condo has been completely renovated in 2026, offering a like-new feel without the wait!Step inside to discover all-new flooring, appliances, lighting, fixtures, vanities, doors, and countertops—every detail

  Amy Longerbeam RE/MAX Roots

  8 Brookland Ct Unit 8, Winchester, VA 22602
• 

  

  /15

  $89,000

  • Land
  • 5.02 Acres
  • $17,729 per Acre

  0 Pack Horse Road Lot B Unit VAFV2042704, 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 5 acre lot B is wooded, has an old cabin (do not enter and at one time had electric), 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

  Dave Spence RE/MAX Roots

  0 Pack Horse Road Lot B Unit VAFV2042704, Winchester, VA 22603
• 

  

  /15

  $210,000

  $10K PRICE DROP

  • Land
  • 5.39 Acres
  • $38,961 per Acre

  TBD (0) Cather Ln, Winchester, VA 22602

  Searching for the ideal place to build your dream home? This awesome 5.39 acre parcel delivers stunning views and a convenient location just minutes from town. Situated right off Rt 50 with easy access to Rt 37 and Interstate 81, you’ll be close to gas stations, restaurants, shopping, the hospital, and so much more—offering the perfect blend of peaceful country living and everyday convenience.

  Brian Doman Preslee Real Estate

  TBD (0) Cather Ln, Winchester, VA 22602
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  /32

  $239,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,257 Sq Ft

  1576 Brookland Terrace Unit 6, Winchester, VA 22602

  Fantastic location! This spacious second-floor condo offers more square footage than most units in the community and features an open, light-filled layout, and durable flooring throughout with NO carpet. The thoughtfully designed floor plan includes a large living room, separate dining area, two generously sized bedrooms, and two full bathrooms. The primary suite offers a private bath, a large

  Kim Hurst MarketPlace REALTY

  1576 Brookland Terrace Unit 6, Winchester, VA 22602
• 

  

  /29

  $265,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,734 Sq Ft

  11 W Germain St, Winchester, VA 22601

  Step inside this historic home in the heart of Winchester and discover a home that offers far more than you might expect. Generously sized rooms provide plenty of space to relax, or enjoy your favorite hobbies, while a light-filled sunroom creates the perfect spot for morning coffee, reading, plants, or simply slowing down and enjoying the day.Inside, you'll find two comfortable bedrooms, a

  Magnolia Halkowitz ERA Oakcrest Realty, Inc.

  11 W Germain St, Winchester, VA 22601

Showing Results 41 - 80, Page 2 of 3