Winchester, VA Homes for Sale under $400,000

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  $240,000

  Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,148 Sq Ft

  304 Ash Hollow Dr, Winchester, VA 22602

  Why rent when you can own a townhouse?! This property has 1,148 square feet of finished living space plus a walk-out patio and yard that backs up to trees. You will find the interior of the townhome freshly painted, and the kitchen featuring new cabinets and countertops, a new range hood, and new tile backsplash. Enjoy the ease of everyday living with a highly convenient commuter location just

  Steph Drahozal Pearson Smith Realty, LLC

  304 Ash Hollow Dr, Winchester, VA 22602
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  /15

  $220,000

  • Land
  • 5.39 Acres
  • $40,816 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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  /17

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft

  369 Charles St, Winchester, VA 22601

  This two-story home offers classic charm with a covered front porch, fenced backyard, and upper-level balcony. Located just minutes from downtown, 369 Charles Street features a recently updated kitchen with modern cabinetry, granite countertops, and stainless steel appliances. The main level features updated flooring, while the upstairs level provides access to a private, covered balcony. Two

  Marisa Varley ERA Oakcrest Realty, Inc.

  369 Charles St, Winchester, VA 22601
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  /24

  $359,990

  New Construction $5K PRICE DROP

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

  12 Monteith Dr, Winchester, VA 22601

  3 Level Townhome with 3 Bedrooms! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen

  DRB Homes Builder

  12 Monteith Dr, Winchester, VA 22601
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  /55

  $365,000

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  617 Fox Trail, Winchester, VA 22602

  Looking for a mountain top getaway? This adorable rancher is it with 3 bedrooms, 2 full baths. Updated kitchen w/stainless appliances and tons of light. Back deck is an oasis with a gazebo and a place to sip morning coffee and overlook the incredible wooded lot. This home has an extra building lot as well (lot is to the left of the home)! Full basement with family room, rec room w/pool table and

  Traci Shoberg Samson Properties

  617 Fox Trail, Winchester, VA 22602
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  /13

  $199,000

  • Land
  • 20.05 Acres
  • $9,925 per Acre

  951 Bobcat Trail, Winchester, VA 22602

  Breathtaking Views and Endless Possibilities! Discover your own slice of paradise on this stunning 20.05-acre property! With a 3-bedroom perc already in place, drainfield and distribution box installed, and electric at the property, you're just a septic tank away from breaking ground. Part of the lot is already cleared, making it the perfect spot to build your dream home, weekend getaway, or cozy

  Sharon Farinholt Realty ONE Group Old Towne

  951 Bobcat Trail, Winchester, VA 22602
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  /3

  $275,000

  • Land
  • 5.79 Acres
  • $47,496 per Acre

  LOT 1 - Handley Dr, Winchester, VA 22603

  Spring Valley Estates. A rare opportunity to find a 5-Acre lots within 5 minutes of downtown Winchester and the Valley Health Medical Center. James Wood High School and Apple Pie Elementary within a mile of this lot. Fully built lot with approved perc on file. Buyer can buy the lot and build their dream house or for future investment purposes. This corner lot is cleared with existing road

  JP Carr Merrifield Realty, LLC

  LOT 1 - Handley Dr, Winchester, VA 22603
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  /26

  $399,990

  New Construction

  • 3 Beds
  • 4 Baths
  • 2,026 Sq Ft

  116 Swansong Place, Winchester, VA 22603

  Exceptional Value – Brand-New 3-Bedroom Townhome for Summer Move-In!Don’t miss this incredible opportunity to own a beautifully crafted new construction townhome in the newest section of Snowden Bridge.Designed for modern living, this home features oak stairs with upgraded railings and durable luxury vinyl plank flooring throughout the main level. The bright, stylish kitchen boasts white

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  116 Swansong Place, Winchester, VA 22603
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  /41

  $365,000

  $34K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,328 Sq Ft

  433 Beechcroft Rd, Winchester, VA 22601

  Buyers financing fell through. No fault of sellers. HUGE PRICE CUT!. Seller is motivated and open to offers.Explore 433 Beechcroft Road, located in the desirable Cedarmeade community. This lovely one-level ranch home features hardwood flooring throughout and offers 4 bedrooms, 2 full baths, and a spacious combined living and dining area.The kitchen is equipped with custom cabinetry,

  Mohammad Ali United Real Estate Premier

  433 Beechcroft Rd, Winchester, VA 22601
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  /22

  $369,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  HOMESITE 44 Shuoner Ct, Winchester, VA 22602

  110 SHUONER Ct – Model Home | We Have spec homes Summer 2026 Delivery AvailableSt. Paul TBB | 4 BR | 3.5 BA | 1-Car Garage | Finished Lower Level + Larger Deck Beautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living — customize your home the way you like, or keep everything as-is at this price, including a 4th bedroom. Home Highlights Open-concept

  Jimmy Thomas New Home Star Virginia, LLC

  HOMESITE 44 Shuoner Ct, Winchester, VA 22602
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  /2

  $215,000

  • Land
  • 40,075 Sq Ft
  • $233,696 per Acre

  0 7 Building Lots In Shawneeland Unit VAFV2032844, Winchester, VA 22602

  REDUCED by $20k! CALLING ALL BUILDERS!! 7 BUILDING LOTS for $215,000 (being sold as a bundle) located in Shawneeland in Frederick County, VA. . Perc approved certification letter, plat and sewer docs on file for each lot. The lots range in size from 0.40-0.92 acres. Potential home sites for permanent home or weekends and vacations. Enjoy hiking, fishing, swimming in the lake, nature walks and

  Caroline W. Barb, REALTOR Jim Barb Realty, Inc.

  0 7 Building Lots In Shawneeland Unit VAFV2032844, Winchester, VA 22602
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  $249,900

  • Land
  • 7.1 Acres
  • $35,197 per Acre

  384 Frog Hollow Rd, Winchester, VA 22603

  7 scenic acres with no restrictions and endless potential. Offering over 450' feet of road frontage, this beautiful parcel features a gentle slope and a thoughtfully prepared layout for future development. A partially cleared area is ready for a potential homesite, with an additional cleared septic location already in place. Current owner is in the process of obtaining well and septic

  Jennifer Sacco RE/MAX Roots

  384 Frog Hollow Rd, Winchester, VA 22603
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  /7

  $139,800

  • Land
  • 2.03 Acres
  • $68,867 per Acre

  0 Wardensville Grade Unit VAFV2042390, Winchester, VA 22602

  Build your dream home on this beautiful 2.03-acre wooded parcel in a desirable Winchester location! Enjoy the perfect combination of privacy and convenience, with easy access to Valley Health, schools, shopping, and Route 37.The current owner has already completed much of the groundwork, making this property ready for your building plans. The lot features an approved 4-bedroom/8-person sewage

  Sandra Brookman RE/MAX Real Estate Connections

  0 Wardensville Grade Unit VAFV2042390, Winchester, VA 22602
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  /24

  $399,900

  New Construction

  • 3 Beds
  • 3 Baths
  • 1,914 Sq Ft

  210 Beaver Trail, Winchester, VA 22602

  6-2-26 almost compleCurrent Shawneeland Inventory107 Pinto Trail (split foyer)208 Beaver Trail (split foyer)210 Beaver Trail (split foyer)212 Falcon Trail (coloinail)211 Inca Trail (colonial)103 Tonto Trail (split foyer)123 Killbuck Trail (colonial)Stunning 3BR/3BA home on 0.33+ acre lot with public water & available Xfinity internet. Easy entrance access. Open

  Jim Thomson Realty ONE Group Old Towne

  210 Beaver Trail, Winchester, VA 22602
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  /17

  $349,990

  New Construction $40K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601

  ***OFFERING UP TO $7K IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS*Featuring Bedford II in Valor Crossing! Open concept kitchen located next to the country kitchen and living room. Optional features include box bay rear window and 10' x 14' deck. Primary suite with large

  Brittany Newman DRB Group Realty, LLC

  TBB Monteith Dr Unit BEDFORD II, Winchester, VA 22601
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  /40

  $315,000

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  406 Raccoon Dr, Winchester, VA 22602

  Back on market, no fault of seller! Seller has replaced main beam and has replaced several logs. Tucked away in the peaceful Wilde Acres neighborhood, this beautiful home offers the perfect balance of privacy, character, and comfort. Inside, you’re welcomed by stunning wide-plank heart pine flooring that brings warmth and timeless character to the living space. A newly updated shower adds a

  STEVEN REESE EXP REALTY LLC - STAFFORD

  406 Raccoon Dr, Winchester, VA 22602
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  /35

  $368,000

  $27K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,656 Sq Ft

  330 Wardensville Grade, Winchester, VA 22602

  MOTIVATED SELLER! Experience the perfect blend of peaceful country charm and modern convenience in this beautifully remodeled 3-bedroom, 1.5-bath home offering comfortable two-level living and true move-in-ready appeal. Thoughtfully updated throughout, this home features all new windows, siding, and roof installed in 2022, along with a HVAC system installed in 2021 with warranty coverage for

  Stacey Rowe Real Broker LLC

  330 Wardensville Grade, Winchester, VA 22602
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  /46

  $359,999

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  307 1/2 E Piccadilly St, Winchester, VA 22601

  Welcome to 307 1/2 E Piccadilly Street, a charming detached home offering comfort, convenience, and character in the heart of Winchester. Ideally located just minutes from Old Town Winchester, the Walking Mall, local restaurants, shopping, parks, and commuter routes, this property places you close to downtown amenities while still offering the privacy and feel of a standalone home. Inside, you’ll

  Nate Crandell HoneyWay

  307 1/2 E Piccadilly St, Winchester, VA 22601
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  /24

  $349,900

  • 3 Beds
  • 1 Bath
  • 1,360 Sq Ft

  104 Hilltop Terrace, Winchester, VA 22602

  THIS HOME IS A MUST SEE! THIS WELL CARED FOR MOVE IN READY HOME HAS NEW UPDATED STAINLESS APPLIANCES, NEW FLOORING THROUGHOUT AND NEWLY REFINISHED ORIGINAL HARDWOOD FLOORS. THIS 3 BEDROOM 1 BATHROOM HOME WITH 2 LIVING ROOMS HAS THE SPACE FOR GROWTH FOR THE NEXT FAMILY IN THIS SOUGHT AFTER COMMUNITY IN THE MIDDLE OF THE CITY BUT IN COUNTY LIMITS. BREATHE TAKING VIEWS FROM THE FRONT PORCH. BRAND

  Richard Kozlowski Real Broker, LLC

  104 Hilltop Terrace, Winchester, VA 22602
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  $259,900

  • 2 Beds
  • 1 Bath
  • 870 Sq Ft

  1125 Conway St, Winchester, VA 22601

  Check out this Very Cute Bungalow in Winchester City! It has a Brand NEW Roof, Freshly Painted throughout, NEW kitchen/hall/bath flooring, NEW Stainless Steel Refrigerator, Restored deck, and Lovely Hardwood! Cozy with 2 Bedrooms and 1 Bath. Surely to be perfect for the first time Home Buyer! Great Location close to shopping & restaurants. Great for commuters as well as it's on the East side of

  Jodi Costello ERA Oakcrest Realty, Inc.

  1125 Conway St, Winchester, VA 22601
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  /12

  $369,900

  • Land
  • 11.49 Acres
  • $32,193 per Acre

  Lot 1 Tavistock Dr, Winchester, VA 22602

  Beautiful 11.49 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 1 Tavistock Dr, Winchester, VA 22602
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  $389,000

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

  328 Longview Ave, Winchester, VA 22601

  This ranch home in Winchester City has been meticulously maintained. Beautiful hardwood floors. Dining room can be converted back to a third bedroom, simply install doors that are being stored in the basement. Basement is 75% finished and offers endless possibilities. The remaining 25% provides room for ample storage and/or a workshop. Note: toilet in workshop area is NOT functional. New HVAC

  Kelly Bauer Coldwell Banker Premier

  328 Longview Ave, Winchester, VA 22601
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  $380,000

  Open Sat 1PM - 4PM $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft

  108 Wild Rose Cir, Winchester, VA 22602

  Welcome home to this beautifully renovated 4-bedroom, 2 full-bath rancher situated on a spacious 0.23-acre lot in the heart of Winchester. Thoughtfully updated from top (New Roof) to bottom, this move-in-ready home offers the perfect blend of modern finishes and comfortable living. The main level has newly installed LVP flooring, 3 bedrooms, a full bath, and a wood-burning fireplace. The fully

  Jon Fleming Weichert Realtors - Blue Ribbon

  108 Wild Rose Cir, Winchester, VA 22602
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  /19

  $399,900

  New Construction $10K PRICE INCREASE

  • 3 Beds
  • 3 Baths
  • 1,914 Sq Ft

  107 Pinto Trail, Winchester, VA 22602

  I AM DONE AND READY! Split foyer low in community and flat lot with easy access out of subdivision. Other inventory of new homes in community208 Beaver Trail210 Beaver Trail212 Falcon Trail211 Inca Trail123 Killbuck Trail103 Tonto

  Jim Thomson Realty ONE Group Old Towne

  107 Pinto Trail, Winchester, VA 22602
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  /30

  $370,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  2294 Welltown Rd, Winchester, VA 22603

  Charming, full of character, and ready for its next chapter! This one-level home sits on a beautiful 1.55-acre lot in Winchester, offering plenty of space to spread out and enjoy country living while still being conveniently located. Inside, you'll find original hardwood floors, a functional layout, and the kind of solid craftsmanship that's hard to find in newer homes. Whether you're looking for

  Meghan Pachas Realty ONE Group Old Towne

  2294 Welltown Rd, Winchester, VA 22603
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  /29

  $374,900

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,263 Sq Ft

  224 Hawk Trail, Winchester, VA 22602

  BACK ON THE MARKET AFTER WELL AND SEPTIC UPDATES. Work just completed for your peace of mind: Septic - tank parged and resealed, new line to new D-box and new header installed. Well - new vertical well pressure tank and assosciated fittings and hardware installed, new submersible pump wire installed with new proper grounding conductor installed, new whole-house water filtration system installed.

  Joelle Graham Weichert, REALTORS

  224 Hawk Trail, Winchester, VA 22602
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  /2

  $199,900

  $50K PRICE DROP

  • Land
  • 5.01 Acres
  • $39,900 per Acre

  Lot 7 Oak, Winchester, VA 22603

  Build Your Vision at the End of the LaneDiscover 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.

  Jim Thomson Realty ONE Group Old Towne

  Lot 7 Oak, Winchester, VA 22603
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  $350,000

  New Construction $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  513 Pheasant Dr, Winchester, VA 22602

  Welcome to this newly built colonial in Wilde Acres situated on 1/4 acre lot nestled among the trees and surrounded by a wall made of native stone. Upon entry, enjoy the open living area and wood floors which make the space warm and comfortable. The galley kitchen offers ample counterspace and new stainless steel appliances. The convenient main level full bath also has hookup for stackable washer

  Ismael Carino MarketPlace REALTY

  513 Pheasant Dr, Winchester, VA 22602
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  /22

  $319,950

  $180K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 1,310 Sq Ft

  593 N Kent St, Winchester, VA 22601

  This charming home, a short walk from historic Winchester, underwent a complete studs up renovation a few years ago. With all new insulation, roof, energy efficient double pane windows, and updated systems, it offers efficiency and ease. The open floor plan flows into a kitchen with a dedicated pantry closet. Three appropriately sized bedrooms include a master with its own bath. Plus, enjoy

  Lawrence Lessin Homes By Owner, Inc.

  593 N Kent St, Winchester, VA 22601
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  /30

  $235,000

  • 2 Beds
  • 1 Bath
  • 783 Sq Ft

  1129 Purcell Ln, Winchester, VA 22603

  This wonderful cape cod is so charming with its covered, front porch, and it's located just outside Winchester city limits, yet before you get to the Sunnyside shopping area. It's tucked away in a community away from the hustle and bustle of town, and yet easy access to commuter routes. Remodeled in 2023, and then further improved. Recent upgrades include a new metal roof, vapor barrier, new

  Natalie Langford ERA Oakcrest Realty, Inc.

  1129 Purcell Ln, Winchester, VA 22603
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  $344,900

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,395 Sq Ft

  420 E Pall Mall St, Winchester, VA 22601

  "Beautifully Renovated On Pall Mall St." This 2-bedroom, 2-full bath ranch style home is ready for you to move right in! Home has been completely painted on the inside, and the outside brick/concrete, side handrails, outside/inside of doors have been freshly painted. The kitchen has new granite counters, new sink & faucet, new LVP flooring and new stainless-steel appliances. Huge family room with

  Matt Kilmer Samson Properties

  420 E Pall Mall St, Winchester, VA 22601
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  $139,900

  • 2 Beds
  • 1 Bath
  • 796 Sq Ft

  1124 Conway St, Winchester, VA 22601

  2 Level Rambler Featuring Spacious Bedrooms and a Functional Layout Perfect for Comfortable Living. Enjoy Quiet Mornings or Evening Relaxation on the Inviting Covered Front Porch, and Take Advantage of the Rear Deck for Outdoor Dining and Entertaining. The Property Also Includes a Walk Out Basement and Storage Shed Providing Extra Space For Tools, Equipment, or Seasonal Items. Situated on a

  Matthew Altizer ANR Realty, LLC

  1124 Conway St, Winchester, VA 22601
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  /7

  $195,000

  • Land
  • 17.8 Acres
  • $10,955 per Acre

  Lot 5 Snake Dr, Winchester, VA 22603

  Build Your Ultimate Private Sanctuary on Hoover Mountain Retreat!Escape the noise and embrace the serene beauty of the Virginia countryside on this magnificent 17.8-acre wooded lot in Northern Frederick County. Boasting an ideal blend of flat clearing areas and scenic rolling hills, this expansive parcel gives you total creative freedom to build your custom estate completely hidden from the

  Andrew Hensley Samson Properties

  Lot 5 Snake Dr, Winchester, VA 22603
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  /41

  $380,000

  • 3 Beds
  • 3 Baths
  • 1,276 Sq Ft

  112 Cornstalk Trail, Winchester, VA 22602

  COME TO THE COUNTRY! WELCOME TO THE GOOD LIFE IN THIS RUSTIC MOUNTAIN-LAKE COMMUNITY WITH A BEACH. A short drive to downtown, Winchester Medical Center, restaurants, shopping and services. Lovely and affordable split foyer with 3 bedrooms, 3 full baths, a finished basement and a 2-car garage. Open floor plan. Large living room with vaulted ceiling. Kitchen with breakfast bar, newer stainless

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  112 Cornstalk Trail, Winchester, VA 22602
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  /45

  $399,990

  New Construction

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

  190 Sioux Loop, Winchester, VA 22602

  Don't miss this fantastic Adams townhome with 4 bedrooms, 3.5 baths, and a 1-car garage spread across three levels with a total of 1,889 square feet. The main level features 9-foot ceilings, luxury vinyl plank flooring, white cabinets with granite countertops, and stainless steel appliances by Whirlpool. With all the smart home features included, monitor your home from 500 miles away! *Photos, 3D

  D.R. Horton Builder

  190 Sioux Loop, Winchester, VA 22602

Showing Results 121 - 155, Page 4 of 4