Winchester, VA Homes for Sale under $500,000

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  /53

  $497,000

  • 3 Beds
  • 2 Baths
  • 2,302 Sq Ft

  101 Delaware Trail, Winchester, VA 22602

  Price Reduced! Be in before the leaves start to change! You must see this home to believe it. Fabulous remodel using the finest materials. Winchester VA. Outdoor activities are everywhere you turn at this completely renovated home in Winchester. Hiking, swimming, biking, and kayaking are all close by. As you sit on the beautiful deck, you can listen to the birds while you have your coffee. There

  

  Kimberly Pace

  EXP Realty, LLC

  (540) 240-9877

  101 Delaware Trail, Winchester, VA 22602
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  Explore Winchester

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  /49

  $422,000

  • 4 Beds
  • 3.5 Baths
  • 2,783 Sq Ft

  500 Quail Dr, Winchester, VA 22602

  500 Quail Dr, Winchester, VA – Beautifully Maintained 4 BR Home in Scenic VirginiaNestled in one of the most picturesque areas of Virginia, this spacious 4-bedroom, 3.5-bathroom home offers the perfect blend of charm, comfort, and convenience. Located just minutes from Interstate 81, you’ll enjoy easy access to commuting routes while still savoring the peace and beauty of your

  

  Dunia Woodward

  Impact Real Estate, LLC

  (540) 274-2342

  500 Quail Dr, Winchester, VA 22602
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  /57

  $455,000

  • 4 Beds
  • 3.5 Baths
  • 1,676 Sq Ft

  125 Alliance Ct, Winchester, VA 22602

  Welcome to this beautifully maintained home in the highly desirable Freedom Manor subdivision in Winchester, VA—ideally located just minutes from shopping, dining, and everyday conveniences. Offering a perfect blend of comfort, functionality, and location, this property is ready to impress.The main level features durable and stylish luxury vinyl plank (LVP) flooring throughout. The living

  

  Rhonda Shade

  ERA Oakcrest Realty, Inc.

  (540) 619-5307

  125 Alliance Ct, Winchester, VA 22602
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  $433,880 New Construction

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

  0 Homesite 117 Monteith Dr Unit 36422335, Winchester, VA 22601

  3 Level End of Row Townhome With 1 Car Garage & Rear Deck! Beautiful open concept living 3 level town home built on concrete slab with a walk-out lower level. Finished Rec Room - 13 ft. 1 in. x 11 ft. 1 in. with a door to the outside/backyard. The living room area is 15 ft. 3 in. x 17 ft., open kitchen layout with an extended island, a box bay window and 10 ft. x 14 ft. deck in the rear of home.

  

  DRB Homes

  Builder

  0 Homesite 117 Monteith Dr Unit 36422335, Winchester, VA 22601
• 

  $429,340 New Construction

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

  0 Homesite 114 Monteith Dr Unit 36422292, Winchester, VA 22601

  3 Level Townhome With Over 1,600 Finished sq. ft., 1 Car Garage & Rear Deck! 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

  

  DRB Homes

  Builder

  0 Homesite 114 Monteith Dr Unit 36422292, Winchester, VA 22601
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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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  /18

  $464,990 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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  /18

  $459,990 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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  /40

  $496,129 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,195 Sq Ft

  117 Wagtail Ln, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1031 at Hiatt Pointe—a two-car, front-load garage END UNIT VILLA with three bedrooms, two full bathrooms, and one half bathroom will be ready IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small. Be welcomed by 9’ ceilings on both levels, oak main stairs, and expertly selected finishes that make this villa

  Shannon L Bray Pearson Smith Realty, LLC

  117 Wagtail Ln, Winchester, VA 22603
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  /23

  $452,990 New Construction

  • 2 Beds
  • 1 Bath
  • 1,564 Sq Ft

  Hemingway Plan at Hiatt Pointe at Snowden Bridge - 55+ Garden Homes Collection, Winchester, VA 22603

  Welcome to your ideal one-level villa- the Hemingway! This thoughtfully designed home centers around a spacious kitchen, perfect for both daily life and entertaining guests. The main level offers two generous bedrooms, including a primary suite featuring a large walk-in closet and a private en suite bathroom for ultimate comfort. Convenience is key with a laundry room located just off the 2-car

  

  Brookfield Residential

  Builder

  105 Wagtail Ln Unit 36578850, Winchester, VA 22603
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  /24

  $454,990 New Construction

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

  CABRAL Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Cabral, a 1,657 square foot open concept two-story home, offers three bedrooms, two and a half bathrooms, a loft and a two-car garage. As you make your way from the front porch into the foyer you will find a convenient first-floor powder room and coat closet. Past the foyer is the large, open concept living room that flows nicely into the eat-in kitchen that overlooks the casual dining area

  

  D.R. Horton

  Builder

  137 Seminole Dr Unit 36203778, Winchester, VA 22602
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  /13

  $499,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,451 Sq Ft

  3131 Eton Place, Winchester, VA 22601

  End of Group, 4 Level Townhome with Deck and 4 ft. Rear Extension! Stunning Fully Upgraded Model Home – Don’t Miss Out! This gorgeous end of group model home at The Lofts at Creekside is a must-see! The Upton II features a gourmet kitchen with stainless steel appliances, quartz countertops, upgraded cabinets, and lighting. Oak staircases, a spacious fourth-level loft, and nine-foot ceilings add

  

  DRB Homes

  Builder

  3131 Eton Place, Winchester, VA 22601
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  $452,539 New Construction

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

  0 Homesite 20 Monteith Dr Unit 36425637, Winchester, VA 22601

  End Of Row Townhome With 1 Car Garage, Gourmet Kitchen & Rear Deck! 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, a box bay window in the rear of the home for extra lighting, and a 10 ft. x 14 ft. deck.

  

  DRB Homes

  Builder

  0 Homesite 20 Monteith Dr Unit 36425637, Winchester, VA 22601
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  /32

  $479,900

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  703 National Ave, Winchester, VA 22601

  Fully renovated in 2025, this 3-bedroom, 2.5-bath home is ideally located within Winchester city limits—just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment, as well as Jim Barnett Park for outdoor recreation. Thoughtful updates and fresh landscaping enhance its curb appeal. Inside, you’ll find brand-new bathrooms with updated lighting, vanities,

  Jennifer Sacco RE/MAX Roots

  703 National Ave, Winchester, VA 22601
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  /50

  $450,000

  • 5 Beds
  • 3 Baths
  • 2,680 Sq Ft

  25 E Hart St, Winchester, VA 22601

  Welcome to 25 E Hart Street! Nestled in the heart of downtown Winchester, this beautifully updated 5-bedroom, 3-bath home is the perfect mix of charm, space, and convenience. Step inside to a bright, spacious living room where a wood-burning fireplace provides the perfect spot to relax and unwind. The updated kitchen is a dream with quartz countertops, stainless steel appliances, crisp white

  Liz Owings RE/MAX Roots

  25 E Hart St, Winchester, VA 22601
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  /46

  $475,000

  • 3 Beds
  • 2 Baths
  • 2,165 Sq Ft

  327 Bryarly Rd, Winchester, VA 22603

  Location! Location! Location! Back on the Market with Beautiful Renovations – A Must-See!Welcome to 327 Bryarly Drive, Winchester, VA 22603 – This charming countryside Cape Cod is back and better than ever! Nestled on a meticulously maintained 1.25-acre lot, this beautifully updated 1941 home blends timeless character with modern upgrades and thoughtful improvements.

  Lisa Behr Coldwell Banker Premier

  327 Bryarly Rd, Winchester, VA 22603
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  /40

  $450,000

  • 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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  /26

  $479,900

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

  811 Berryville Ave, Winchester, VA 22601

  PRICE REDUCED .....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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  /47

  $450,000

  • 3 Beds
  • 1.5 Baths
  • 1,952 Sq Ft

  164 Bethel Grange Rd, Winchester, VA 22603

  Beautiful brick ranch in a lovely rural setting with mountain views and only minutes to schools and town amenities. Sellers just installed new central air conditioning. 3 bedrooms, 1 1/2 baths with a shower stall in mud room downstairs. Country kitchen with adjoining carport. Large living room front window with nice view of Round Hill. Extra closets. 4 ft hallway with ceiling fan. 5x16 covered

  Cathy Durbin Crum Realty, Inc.

  164 Bethel Grange Rd, Winchester, VA 22603
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  /28

  $475,000

  • 6 Beds
  • 3 Baths
  • 2,736 Sq Ft

  386 Round Hill Rd, Winchester, VA 22602

  ATTENTION INVESTORS - OFFERED AT A NEW PRICE!! *** You will want to check out this fantastic opportunity - with a history of POSITIVE CASH FLOW these two ADJACENT PROPERTIES on a combined total of 1.91-acres in Winchester, just minutes from Valley Health Campus, shopping, restaurants and Rt. 37, may be what you are looking for! *** These two parcels are to be sold TOGETHER; they are not

  Bridget Aikens Colony Realty

  386 Round Hill Rd, Winchester, VA 22602
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  /52

  $475,000

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft

  129 Jalapa Trail, Winchester, VA 22602

  Brand new everything, Roof, appliances, water treatment , bathrooms, deck, Sunroom, flooring Motivated Seller The perfect retreat for everyone, Welcome to your dream home in the heart of the Virginia Mountains , yet only 7 miles to the new Medical Center in Winchester. The property has access to the community lake, picnic grounds, play ground and loads of nature trails

  Leslie Woods-Hulse Century 21 Redwood Realty

  129 Jalapa Trail, Winchester, VA 22602
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  /23

  $449,900

  • 3 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  104 Primrose Place, Winchester, VA 22602

  Moe Gahche Long & Foster Real Estate, Inc.

  104 Primrose Place, Winchester, VA 22602
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  /6

  $432,539 New Construction

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

  HOMESITE 20 Monteith Dr, Winchester, VA 22601

  *OFFERING UP TO 15K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE.*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

  Brittany Newman DRB Group Realty, LLC

  HOMESITE 20 Monteith Dr, Winchester, VA 22601
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  /2

  $450,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,313 Sq Ft

  116 Route 1288, Winchester, VA 22602

  BRAND NEW HOME. ALMOST FULLY FINISHED. No HOA. Discover the charm of this stunning new construction home in the desirable Asbury Terrace community, set to be completed by October 2025. This exquisite Colonial-style residence boasts a thoughtful layout with 3 spacious bedrooms and 2.5 luxurious bathrooms, including a master suite featuring a relaxing soaking tub and walk-in closet. The heart of

  Elcy Pereira Elcy & Co. Realty, LLC.

  116 Route 1288, Winchester, VA 22602
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  /5

  $450,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  113 Whipp Dr, Winchester, VA 22602

  Coming Soon! This sweet 4 bed, 2.5 bath home will be ready to showcase in person mid-September! The moment you enter this charming single-family property you will feel right at home! From the full length front porch step into the open entry and join us in the living area, overlooking the front yard. Beyond that the family room expands right into your eat-in kitchen, all looking out onto your

  Cindy Greenya Keller Williams Realty

  113 Whipp Dr, Winchester, VA 22602
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  /38

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  163 Margaret Ln, Winchester, VA 22603

  (Magnificent Margaret) This home has a lot to offer: All bedrooms and bathrooms on the main level, fully updated kitchen with Stainless Steel Appliances (Fridge, Dishwasher, Stove, Microwave) Quartz counter top, built in pantry, remodeled bathrooms with a double vanity in the primary bathroom and a walk-in tile shower, Central Heating & Air, New windows, Laundry room, large driveway, two car

  Michael Sprague Samson Properties

  163 Margaret Ln, Winchester, VA 22603
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  /69

  $408,900 Open Sat 11AM - 1PM

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

  154 Solara Dr, Winchester, VA 22602

  This lovely modern townhome is better than new! Featuring a fully fenced and level backyard with a deck & custom blinds throughout makes this lovely home ready to move in without the added expense. SOLAR PANELS ARE FULLY PAID FOR- SAVING YOU THOUSANDS IN UTILITY COSTS! (Electric bills are averaging only $20/month). Freshly painted with new luxury vinyl plank flooring, and elegant hardwood floors

  Michele Gibson Samson Properties

  154 Solara Dr, Winchester, VA 22602
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  /41

  $440,000

  • 3 Beds
  • 1 Bath
  • 1,925 Sq Ft

  103 Blue Ridge Ln, Winchester, VA 22602

  Welcome to this beautifully renovated brick rancher on a spacious 0.55-acre lot in a quiet neighborhood just outside Stephens City and Winchester. This move-in-ready 3-bedroom 1-bathroom home offers a perfect blend of modern updates and comfortable living. Step inside to find luxury vinyl plank flooring throughout, fresh lighting fixtures, and a completely updated kitchen featuring quartz

  Jon Fleming Weichert Realtors - Blue Ribbon

  103 Blue Ridge Ln, Winchester, VA 22602
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  /34

  $469,900

  • 3 Beds
  • 3.5 Baths
  • 2,052 Sq Ft

  711 S Braddock St, Winchester, VA 22601

  This well-maintained 3-bedroom, 3.5-bath home offers bright, open living spaces with plenty of natural light. The main level features a spacious living room, an updated kitchen with stainless steel appliances, and a dining area. The back patio features an open area and green space with a fenced backyard—great for relaxing or entertaining. Upstairs, you’ll find a generous primary suite with a full

  Dave Spence RE/MAX Roots

  711 S Braddock St, Winchester, VA 22601
• 

  

  /20

  $499,900

  • Studio
  • 2,376 Sq Ft

  510 N Loudoun St, Winchester, VA 22601

  All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD/1BA with unfinished attic, main floor is 1BR/1BA (Both have rear balcony) and basement unit has access to storage area and includes1BD/1BA. All units have washer/dryer (Basement unit washer/dryer belongs to tenant). Owner/Agent and home inspection report available upon request.

  Dave Spence RE/MAX Roots

  510 N Loudoun St, Winchester, VA 22601
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  /25

  $445,000

  • 4 Beds
  • 3.5 Baths
  • 2,892 Sq Ft

  112 Hites St, Winchester, VA 22602

  No HOA! Discover the expanded comfort of this charming home, featuring a spacious addition completed in 2011. Two master suites: one upstairs and the other one at the main level—it’s ideal for multigenerational living or a private in-law suite. Enjoy a fenced backyard, attached single-car garage, and updates including a newer roof (2015) and HVAC system with heat pump and gas furnace (2011). The

  Rocio Benavides Orus Realty Inc

  112 Hites St, Winchester, VA 22602
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  /39

  $419,900 Open Sun 1PM - 3PM

  • 5 Beds
  • 2 Baths
  • 2,363 Sq Ft

  707 S Braddock St, Winchester, VA 22601

  Welcome to this charming, fully remodeled home located in the heart of Winchester.Experience the timeless appeal of Old Winchester charm, just minutes from the vibrant walking mall, shops, restaurants, and the famous Apple Blossom Parade route. This beautifully remodeled home features LVP flooring throughout and a light-filled open floor plan that seamlessly blends historic character with

  Heloisa Amar Samson Properties

  707 S Braddock St, Winchester, VA 22601
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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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  /49

  $499,870

  • 5 Beds
  • 3 Baths
  • 3,116 Sq Ft

  110 Carter Place, Winchester, VA 22602

  Contract fell through! Extensive Renovations: The home has been fully renovated in 2025, including updates to kitchen, bathrooms, flooring, and fresh paint throughout. Designed to accommodate two families comfortably, featuring large rooms that are flooded with natural light like the entire house. The lower level is equipped with wheelchair-accessible features, enhancing mobility and

  Rodrigo Cruz Long & Foster Real Estate, Inc.

  110 Carter Place, Winchester, VA 22602
• 

  

  /45

  $439,900

  • 3 Beds
  • 3 Baths
  • 1,924 Sq Ft

  275 Greenwood Rd, Winchester, VA 22602

  Charming split-foyer home situated on a generous 13,000 sq. ft. lot with convenient access to Routes 7 and 81. The main level boasts neutral-toned walls and a distinctive dual-sided fireplace, seamlessly connecting the living and dining areas. The dining room and well-appointed kitchen feature elegant hardwood flooring and an abundance of natural light, enhanced by a full-size window and sliding

  Jose Ugaz Gates Smart Realty, LLC

  275 Greenwood Rd, Winchester, VA 22602
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  /32

  $495,000

  • 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

  Cherish Green Coldwell Banker Elite

  201 Parkway St, Winchester, VA 22601
• 

  

  /50

  $429,900

  • 5 Beds
  • 3.5 Baths
  • 1,776 Sq Ft

  103 Fenwick Ct, Winchester, VA 22602

  REDUCED! REDUCED!! REDUCED!!! Don't miss this well cared for home featuring 5 bedrooms and 3.5 bathrooms! It's located in a quiet neighborhood on a cul-de-sac and convenient to route 7 and Route 81 for commuters. NEW Large, private 6 car asphalt driveway so plenty of off-street parking! Whole length of house rear deck for entertaining! Featuring rare main level bedroom with attached full

  Sara Helmke Samson Properties

  103 Fenwick Ct, Winchester, VA 22602
• 

  

  /7

  $499,000

  • Land
  • 18 Acres
  • $27,753 per Acre

  Lot 13 Tavistock Dr, Winchester, VA 22602

  Beautiful 17.98 acre Lot, approved for 3 bedroom perk, Tavistock Estates, one of the last lots remaining! A gorgeous 7 minute drive from town through farmland and full of mountain views. Excellent neighborhood, road access is great, level lot among 'horse country' estates! Build your dream mini equestrian farm or just enjoy peace, quiet, and serenity with the genius of a quick commute into town!

  Gillian Greenfield Coldwell Banker Premier

  Lot 13 Tavistock Dr, Winchester, VA 22602
• 

  

  /3

  $470,335

  • Land
  • 1.37 Acres
  • $343,310 per Acre

  0 Senseny Rd Unit VAFV2009062, Winchester, VA 22602

  PRICE REDUCED!! Owners are looking for reasonable offers. Lot fronts on Senseny road but can be accessed from the shopping center parking lot. Also can be purchased jointly with Lot H. Lot is flat and ready for development. The house adjoining the lot may also be available for purchase.

  John Coontz Commercial Specialists

  0 Senseny Rd Unit VAFV2009062, Winchester, VA 22602
• 

  /2

  $500,000

  • Studio
  • 1,175 Sq Ft

  513 and 525 Monticello St, Winchester, VA 22601

  For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb

  Brett Haynes Oakcrest Commercial LLC.

  513 and 525 Monticello St, Winchester, VA 22601

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