Winchester, VA Homes for Sale under $500,000

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  /39

  $434,000

  • 3 Beds
  • 2.5 Baths
  • 2,277 Sq Ft

  422 S Loudoun St, Winchester, VA 22601

  Priced at recent appraised value. Welcome home to this beautifully maintained historic log home in the heart of Winchester. Thoughtfully updated while maintaining the charm of yesteryear this home offers the conveniences of modern living. Traditionally appointed, the main level of the home provides the perfect separation of spaces with a large formal living room, dining room, gourmet kitchen,

  Dana Cloud Realty ONE Group Old Towne

  422 S Loudoun St, Winchester, VA 22601
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  /9

  $308,000

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft

  2519 Hockman Ave, Winchester, VA 22601

  This charming cottage in the heart of the City of Winchester is poised for a remarkable transformation with major renovations slated for 2026. Built in 1950, this detached home offers a unique opportunity for investors seeking to capitalize on a revitalized property in a desirable location. With two spacious bedrooms and two full bathrooms, the layout is perfect for modern living. The full

  Meridee Powars Link Realty Services LLC

  2519 Hockman Ave, Winchester, VA 22601
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  /44

  $319,900

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  12 N Purcell Ave, Winchester, VA 22601

  Welcome to 12 N Purcell Ave, a classic white bungalow offering standout curb appeal, a well-kept lawn and landscaping, and an unbeatable central location. Relax on the covered front porch before stepping inside to a bright and inviting main level featuring rich hardwood floors and a spacious eat-in kitchen with plentiful cabinet space. Two sizable bedrooms and a full bath round out the main floor

  Dan Whitacre Colony Realty

  12 N Purcell Ave, Winchester, VA 22601
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  /31

  $379,900

  $19K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,909 Sq Ft

  527 Grouse Dr, Winchester, VA 22602

  Welcome to 527 Grouse Drive—almost new construction offering the perfect blend of modern finishes, functional living space, and peaceful mountain surroundings. This beautifully updated split foyer home features 3 bedrooms, 2.5 bathrooms, and over 1,900 finished square feet situated on a spacious lot.Open-concept layout filled with natural light, fresh paint throughout, updated light fixtures,

  Amanda Magana RE/MAX Roots

  527 Grouse Dr, Winchester, VA 22602
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  /2

  $385,000

  Coming Soon Sep 23

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  108 Williamson Rd, Winchester, VA 22602

  Coming soon in Winchester! Welcome to this beautifully maintained 3-bedroom, 2-bath brick rambler in a convenient location. This move-in-ready home offers comfortable one-level living and features an updated kitchen with quartz countertops and stainless steel appliances, updated bathrooms, attractive flooring throughout, and a detached side-entry garage. The current owner has carefully maintained

  Nathalie Acosta Spring Hill Real Estate, LLC.

  108 Williamson Rd, Winchester, VA 22602
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  /52

  $399,000

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,799 Sq Ft

  437 Beechcroft Rd, Winchester, VA 22601

  PRICE REDUCED! BRICK BEAUTY ON A CORNER LOT WITH AN ATTACHED CARPORT AND A FULL BASEMENT. This remodeled and freshly painted 2-bedroom, 2-bath rancher with newly refinished hardwood floors is move-in ready. In-town convenience with nearby shopping, restaurants and services. A short drive to commuter routes 81, 37 and 50, downtown and Winchester Medical Center. Perfect for those who are downsizing

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  437 Beechcroft Rd, Winchester, VA 22601
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  /26

  $359,000

  New Construction $14K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  600 Winchester Dr, Winchester, VA 22602

  Blue Ocean Modulars introduces The Laurel, a three-bedroom, two-full-bath ranch home to be built in the Wilde Acres subdivision of Frederick County. Nestled against a forested backdrop and built with high-quality workmanship, this residence showcases modern construction designed for durability, comfort, and long-term value. The home features Insul-Stud framing, a cutting-edge system that enhances

  Rebecca McTavish Long & Foster Real Estate, Inc.

  600 Winchester Dr, Winchester, VA 22602
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  /18

  $499,990

  New Construction $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,050 Sq Ft

  108 Zinnia Ln, Winchester, VA 22603

  This stunning twin/semi‑detached home is ready for move in and located within the desirable 55+ gated community, Hiatt Pointe at Snowden Bridge. Designed for effortless main‑level living, the home features both a primary and secondary bedroom on the first floor—perfect for comfort and convenience.An open floor plan seamlessly connects the family room and kitchen, creating an inviting space

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  108 Zinnia Ln, Winchester, VA 22603
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  /28

  $399,000

  • 2 Beds
  • 2 Baths
  • 2,094 Sq Ft

  101 Delaware Trail, Winchester, VA 22602

  Welcome to 101 Delaware Trail, a beautifully reimagined retreat in the Shawneeland community of Winchester. This distinctive home combines extensive updates and elevated finishes with a peaceful, wooded setting.Inside, the open-concept design is highlighted by abundant windows bringing in natural light and framing the views of the surrounding landscape. The extensively renovated interior

  Katie Landi Jordan Samson Properties

  101 Delaware Trail, Winchester, VA 22602
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  /64

  $495,000

  $20K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,814 Sq Ft

  516 Deer Creek Rd, Winchester, VA 22602

  Nestled on a private 2-acre lot in the desirable Hogue Creek subdivision, this charming 3-bedroom, 2.5-bath home offers the perfect combination of comfort, character, and space. Surrounded by mature trees and featuring a convenient horseshoe driveway, the property provides a peaceful retreat while remaining close to everyday conveniences.Inside, the inviting family room showcases hardwood

  Laura White ERA Oakcrest Realty, Inc.

  516 Deer Creek Rd, Winchester, VA 22602
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  /91

  $429,900

  $15K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,703 Sq Ft

  104 Kapok Cir, Winchester, VA 22602

  Welcome to the neighborhood of Apple Ridge in Eastern Frederick County. You won't find a nicer home or more quiet cul-d-sac anywhere let alone one that has been more tastefully remodeled. The owners have completed so much updating here, including a brand new tub, faucet annd surround in the primary bedroom. It has a transferable lifetime warranty. This 3 bedroom 2.5 bath home has a welcoming

  Lisette Turner Century 21 Redwood Realty

  104 Kapok Cir, Winchester, VA 22602
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  /26

  $364,990

  New Construction $3K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  11 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with Lower Level Bathroom! This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free

  DRB Homes Builder

  11 Monteith Dr, Winchester, VA 22601
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  /35

  $350,000

  New Construction $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  302 Pheasant Dr, Winchester, VA 22602

  NEW CONSTRUCTION — PRICED TO SELL AT $350,000! If you’ve been waiting for new construction that offers more than just fresh finishes, 302 Pheasant Drive deserves a look. Built by a local builder with more than 20 years of experience, this 3-bedroom, 2-bath ranch combines quality craftsmanship, one-level living, and a full walkout basement that gives you room to grow.The main level offers

  Tyler Hazelwood Virginia Real Estate

  302 Pheasant Dr, Winchester, VA 22602
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  /20

  $459,990

  New Construction $18K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,564 Sq Ft

  107 Lawford Way, 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

  107 Lawford Way, Winchester, VA 22603
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  /47

  $395,000

  $10K PRICE DROP

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

  135 Tye Ct, Winchester, VA 22602

  PRICE IMPROVEMENT! This wonderful home is now offered at a new price. Come see all it has to offer!Welcome to this beautifully designed end-unit townhome featuring three finished levels, a 1-car garage, and an open, light-filled floor plan that perfectly blends style and functionality. The main living areas are enhanced with durable luxury vinyl plank flooring, while the gourmet kitchen

  Leah Clowser RE/MAX Roots

  135 Tye Ct, Winchester, VA 22602
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  /33

  $300,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,281 Sq Ft

  115 S Purcell Ave, Winchester, VA 22601

  Price Improvement!!! Don't miss this 3-bedroom, 3 full-bath bungalow in a prime location! Just minutes from vibrant downtown shopping and dining, and a short walk to Jim Barnett Park. The park includes a dog park, swimming pool, and pickleball courts. This home offers the ideal combination of convenience, charm, and access to outdoor amenities. New roof installed in 2018.

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
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  /79

  $409,900

  • 4 Beds
  • 3 Baths
  • 2,228 Sq Ft

  117 Old Dominion Dr, Winchester, VA 22603

  Well-maintained split foyer in a spectacular commuter location, just minutes from I-81 and a short drive to Old Town Winchester. This inviting home features hardwood floors throughout the main living areas, an open-concept floor plan, a cozy fireplace in the living room, and a spacious kitchen with a center island.The main level offers new carpet in the bedrooms, including a generous primary

  Heloisa Amar Samson Properties

  117 Old Dominion Dr, Winchester, VA 22603
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  /27

  $429,990

  New Construction $38K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,461 Sq Ft

  125 Trellis View Ln, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa, blending style and functionality in a single-level open layout and finished loft, complete with a 2-car garage. This stunning 1,492 sq. ft. residence features three bedrooms and two baths on the main level, with the finished loft offering an additional 676 sq ft of

  D.R. Horton Builder

  125 Trellis View Ln, Winchester, VA 22602
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  /64

  $439,000

  • 3 Beds
  • 2 Baths
  • 1,822 Sq Ft

  109 Keswick Ct, Winchester, VA 22602

  Some homes have a screened porch. This one has a screened porch you may never want to leave. You could sit on your front porch and enjoy a rain shower, but you might be happier on your large, screened-in porch overlooking a wooded view and your gorgeous backyard. Wood floors welcome you into the home and you're immediately drawn to the recently remodeled kitchen. The large kitchen island,

  Natalie Langford ERA Oakcrest Realty, Inc.

  109 Keswick Ct, Winchester, VA 22602
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  /42

  $400,000

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

  116 Cloverdale Ct, Winchester, VA 22602

  Located in the Brentwood Terrace Subdivision Near Greenwood Drive & Valley Mill Rd This Spectacular Three Level 3 Bedroom 2.5 Bathroom Single Family Home is Situated on a Beautifully Manicured Private Cul-De-Sac Lot Surrounded by Trees, Inviting Front Porch, Fenced-In Back Yard, Deck, & Newly Paved Driveway! The Sellers Pride of Ownership Includes 2 Brand New Upgraded Dual HVAC Systems (2026),

  Bill Fritz RE/MAX Executives

  116 Cloverdale Ct, Winchester, VA 22602
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  /36

  $397,990

  New Construction

  • 3 Beds
  • 2.5 - 3.5 Baths
  • 1,966+ Sq Ft

  St Paul Plan at Winchester Ridge Townhomes, Winchester, VA 22602

  Introducing the St. Paul, one of Maronda’s latest townhome designs.The St. Paul offers a range of 1,966 to 1,989 square feet of living space, including 3 to 4 bedrooms, 2.5 to 3.5 bathrooms, and a spacious 1-car garage. This new design offers plenty of personalization opportunities to fit your family’s unique needs.On the first floor of the home, you will find a spacious, open-concept floor plan.

  Maronda Homes Builder

  161 Williamson Rd Unit 37409245, Winchester, VA 22602
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  /46

  $499,999

  • 4 Beds
  • 3.5 Baths
  • 2,524 Sq Ft

  2643 Middle Rd, Winchester, VA 22601

  Location, Location, Location! NO HOA!!! Priced below assessed value! Hardwood floors on the main level. Formal living and dining room leads to the Family room with stone fireplace, breakfast nook and kitchen. Step out on to the deck to enjoy the views. Large fenced level backyard. Large Primary suite with sitting room and luxury bath. Good sized bedrooms, one with an attached bath. Lower level

  Lorraine Arora Berkshire Hathaway HomeServices PenFed Realty

  2643 Middle Rd, Winchester, VA 22601
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  /21

  $210,000

  • Land
  • 5 Acres
  • $42,000 per Acre

  0 Off of Mount Olive Rd Unit VAFV2044302, Winchester, VA 22603

  Prime building lot conveniently located less than 10 minutes west of Winchester with immediate access to US-50 - Northwestern Pike. Part of what was once the well known Rotz Farm and now part of the brand new Ridgeview Glen community. This land is ideally positioned between scenic Flint Ridge and flowing Hogue Creek. This tract features a 4 bedroom septic certification letter which is already on

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Off of Mount Olive Rd Unit VAFV2044302, Winchester, VA 22603
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  /29

  $369,999

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

  120 Maury Way, Winchester, VA 22602

  Welcome to this beautifully upgraded townhome in the highly sought-after Winchester Landing active adult community! Built in 2023, this move-in-ready home offers the perfect blend of modern style, comfort, and convenience. Designed with true main-level living in mind, the spacious first floor features a desirable primary suite, full bath, and laundry room, making everyday living effortless. The

  Samiirah Ruhomutally Pearson Smith Realty, LLC

  120 Maury Way, Winchester, VA 22602
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  /36

  $355,500

  $4K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,644 Sq Ft

  423 Panther Dr, Winchester, VA 22602

  Welcome to 423 Panther Dr in Winchester, VA! This spacious split-level home offers 4 bedrooms, 3 full bathrooms, a 2-car front-entry garage, gravel driveway, and a storage shed, all situated in a convenient and peaceful setting.The upper level features 3 bedrooms and 2 full bathrooms. The kitchen and living areas showcase beautiful hardwood flooring, with new carpet throughout the

  Caleb Fowler Samson Properties

  423 Panther Dr, Winchester, VA 22602
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  /22

  $459,990

  New Construction

  • 2 - 3 Beds
  • 1 Bath
  • 1,670+ Sq Ft

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

  Welcome to your dream one-level villa, the Fitzgerald! This beautifully designed home features a central kitchen that serves as the heart of the house, perfect for both everyday living and entertaining. The main level includes two spacious bedrooms, including a luxurious primary suite with an expansive walk-in closet and an en suite bathroom for your comfort and privacy. Additionally, you'll find

  Brookfield Residential Builder

  105 Wagtail Ln Unit 36578849, Winchester, VA 22603
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  /15

  $375,990

  New Construction $16K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,752 Sq Ft

  105 Heirloom Way, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  Brookfield Residential Builder

  105 Heirloom Way, Winchester, VA 22603
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  /2

  $439,000

  Coming Soon Sep 10

  • 5 Beds
  • 3 Baths
  • 2,508 Sq Ft

  300 Pembridge Dr, Winchester, VA 22602

  Welcome to this newly renovated and thoughtfully designed 5-bedroom, 3-full-bath home offering exceptional flexibility for modern living, rental income, or multigenerational living.Featuring two full kitchens, two dining areas, and potentially two separate living spaces, this home provides a unique opportunity to create two distinct living areas under one roof. Bottom level has two

  Magnolia Halkowitz ERA Oakcrest Realty, Inc.

  300 Pembridge Dr, Winchester, VA 22602
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  /14

  $495,990

  New Construction $14K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,216 Sq Ft

  101 Seminole Dr, Winchester, VA 22602

  The Glendale is a 2,216 square foot corner homesite, open concept two-story home with a finished basement that offers four bedrooms, three and a half bathrooms with a two-car garage. You will immediately feel at home as you enter the foyer and make your way into the spacious family room. This living space flows nicely into the eat-in kitchen with plenty of cabinets and island overlooking the

  D.R. Horton Builder

  101 Seminole Dr, Winchester, VA 22602
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  /7

  $499,000

  • Land
  • 17.98 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
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  /22

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft

  452 Valley Mill Rd, Winchester, VA 22602

  SOLD AS IS, CASH ONLY! Investor special on this great home that is on .55 Acre lot (2 lots make this up). Outbuildings, wood floors, fireplace, 3 generous size bedrooms, laundry room, eat in kitchen and dining room. Home needs to be hooked up to county water, current well not working properly. Call for details.

  Deborah Matthews ERA Oakcrest Realty, Inc.

  452 Valley Mill Rd, Winchester, VA 22602
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  /96

  $459,999

  $30K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 1,887 Sq Ft

  419 Summit Ave, Winchester, VA 22601

  Welcome Home! This beautifully renovated single-family home offers everything you need and more. Featuring hardwood floors throughout the main level, custom cabinets, and granite countertops in the kitchen, this home combines style and functionality. A new roof adds peace of mind, and the fully finished lower level provides additional living space for relaxation or entertainment. With 5 spacious

  Waqas Abbasi Lifestyle Realty, LLC.

  419 Summit Ave, Winchester, VA 22601
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  /17

  $385,690

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  660 Arden Ct, Winchester, VA 22601

  660 Arden Court is an attractive new 3 level townhome with brick backing to trees in Winchester's premier Meadow Branch community for September move-in. Our modern Adams floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. The main level with LVP Floors features a kitchen equipped with beautiful Quartz countertops, white cabinets, and stainless-steel appliances.

  D.R. Horton Builder

  660 Arden Ct, Winchester, VA 22601
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  /18

  $290,000

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  132 Geronimo Trail, Winchester, VA 22602

  Professional photos coming soon. Welcome home to 132 Geronimo Trail! Situated in a quiet and highly desirable neighborhood, this charming single-family home is perfect for first-time buyers, downsizers, or anyone seeking a peaceful retreat. This 1,232 square-foot rancher features 3 bedrooms, 2 full bathrooms, eat-in kitchen, living room, a brick fireplace with highly a efficient wood-burning

  Shane Price Long & Foster Real Estate, Inc.

  132 Geronimo Trail, Winchester, VA 22602
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  /28

  $400,000

  $29K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,432 Sq Ft

  115 E Monmouth St, Winchester, VA 22601

  Welcome to this 2 level house, the spacious patio backyard will be the perfect spot to relax and enjoy a relaxing day. Located near multiple stores and parks. Schedule your showing today!

  Mafe Zambrano Inmobiliaria De Las Casas LLC

  115 E Monmouth St, Winchester, VA 22601
• 

  

  /18

  $402,160

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft

  169 Sioux Loop, Winchester, VA 22602

  Move into your new home this September/October and enjoy the best of fall in this stunning Adams end-unit townhome! Featuring a classic white siding exterior and bright, timeless white cabinetry, this home offers 4 bedrooms, 3.5 baths, a 1-car garage, and 1,889 square feet of thoughtfully designed living space across three levels. The main level showcases 9-foot ceilings, luxury vinyl plank

  D.R. Horton Builder

  169 Sioux Loop, Winchester, VA 22602
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  /10

  $399,000

  • Land
  • 3,920 Sq Ft
  • $4,433,333 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
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  /34

  $350,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  411 Cardinal Dr, Winchester, VA 22602

  $5,000 BUYER INCENTIVE with an acceptable offer! Newly completed and move-in ready, 411 Cardinal Dr. offers 3 bedrooms, 2 full bathrooms, and easy one-level living in Winchester.Step inside to a bright, open layout with durable LVP flooring throughout the home. The kitchen features granite countertops, upgraded stainless steel appliances, ample cabinetry, and a spacious island overlooking

  Abby Walters Preslee Real Estate

  411 Cardinal Dr, Winchester, VA 22602
• 

  

  /30

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft

  540 Bellview Ave, Winchester, VA 22601

  Attention investors! Charming rambler just minutes from historic Old Town Winchester with convenient access to I-81, making commuting simple and stress-free. This inviting home features beautiful hardwood floors, a spacious living room with a cozy fireplace, and a formal dining room perfect for hosting family and friends. The kitchen offers easy access to the backyard, creating a seamless flow

  Heloisa Amar Samson Properties

  540 Bellview Ave, Winchester, VA 22601
• 

  

  /31

  $499,900

  $60K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,068 Sq Ft

  110 Russelcroft Rd, Winchester, VA 22601

  Nestled in the established Cedarmeade community, this beautifully updated 4-bedroom, 3-bath ranch home offers the perfect combination of comfort, style, and functionality. With over 2,000 square feet of finished living space, this home is designed to accommodate both everyday living and effortless entertaining.Step inside to find warm hardwood flooring, abundant natural light, and

  Grace Mooney Coldwell Banker Premier

  110 Russelcroft Rd, Winchester, VA 22601

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