Winchester, VA Homes for Sale under $500,000

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  /47

  $379,990

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 2,102 Sq Ft

  519 Fairmont Ave, Winchester, VA 22601

  Expect a long love affair with this home.Some homes feel like they were built with patience, pride, and a sense of permanence—and this historic Winchester beauty has that feeling the moment you step inside. Set near Old Town Winchester and positioned right next to the approved Cider Hill Neighborhood Design District, it offers something rare: preserved historic character today, with a

  Hannah Won Samson Properties

  519 Fairmont Ave, Winchester, VA 22601
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  /30

  $399,000

  • 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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  /52

  $425,000

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

  437 Beechcroft Rd, Winchester, VA 22601

  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 or just

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  437 Beechcroft Rd, Winchester, VA 22601
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  /21

  $384,990

  New Construction

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

  422 Granite Ridge Dr, 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

  422 Granite Ridge Dr, Winchester, VA 22603
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  /45

  $374,900

  Open Sun 2PM - 4PM

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

  106 Hardy Way, Winchester, VA 22602

  Why wait for new construction when you can move right into a home that still feels brand new? Built in 2024 and used only as a second home for a combined total of approximately two months, this beautifully maintained townhome offers all the benefits of new construction without the wait. Designed for easy living, the open floor plan features a spacious kitchen with granite countertops, stainless

  Lori Oaks MarketPlace REALTY

  106 Hardy Way, 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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  /7

  $200,000

  • Land
  • 5 Acres
  • $40,000 per Acre

  Lot A Cather Ln, Winchester, VA 22602

  Looking for the perfect spot to build your dream home? This 5-acre parcel of pasture land offers stunning views and an unbeatable location just minutes from town. With a 4-bedroom alternative septic certification letter already in place and minimal covenants and restrictions, you’ll have the freedom to create the home and lifestyle you’ve been envisioning. Local builder recommendations available.

  Kaitlyn Behr Samson Properties

  Lot A Cather Ln, Winchester, VA 22602
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  /49

  $399,500

  $50K PRICE DROP

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

  155 Royal Ave, Winchester, VA 22602

  Two lots in this listing for sale. The home on Royal Avenue with a buildable lot adjoining and fronting Front Street. Super location in Winchester, VA. This property is located just past Costco off of Rte. 522S. Situated on a quiet street this Cape Cod has a wonderful covered front porch with the addition of a rear closed in porch. The main and upstairs have hardwood flooring. The main floor

  Jim Stafford ERA Oakcrest Realty, Inc.

  155 Royal Ave, Winchester, VA 22602
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  /41

  $379,900

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,405 Sq Ft

  1851 Melvor Ln, Winchester, VA 22601

  Extremely well-maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+ community. This main-level living home features an open floor plan, vaulted ceiling, solar tubes for natural light, and a cozy gas fireplace in the living room. The primary suite offers a private bath, while a bright Florida room provides additional space for relaxing or entertaining. Step outside to

  RoxAnn Grimes RE/MAX Roots

  1851 Melvor Ln, Winchester, VA 22601
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  /73

  $439,900

  • 3 Beds
  • 1.5 Baths
  • 2,560 Sq Ft

  170 Mountain View Ct, Winchester, VA 22603

  Charming 3-bedroom, 1.5-bath colonial home on 5 acres, with an additional 7 acres available. Nestled in nature, it features a detached 2-car garage with power and lights, run-in shed, large gazebo with a chandelier for evening ambiance, and a metal carport for 2 cars. Enjoy the outdoors from the spacious front porch. This home features 4 heat sources so each room will feel comfortable during

  Pamela Foltz Realty ONE Group Old Towne

  170 Mountain View Ct, Winchester, VA 22603
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  /3

  $425,000

  • 4 Beds
  • 3 Baths
  • 2,157 Sq Ft

  1709 Brandon Dr, Winchester, VA 22601

  Spacious Home in a Prime Location! Discover the potential of this well-built Cape Cod offering generous living spaces and timeless charm. The welcoming living and dining area features a cozy fireplace, creating the perfect setting for gatherings and everyday living. The main level includes a desirable primary suite with a private full bath, an additional bedroom, and a hall bath for added

  Darcy Amburn Colony Realty

  1709 Brandon Dr, Winchester, VA 22601
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  /62

  $325,000

  $125K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,585 Sq Ft

  139 Bryarly Rd, Winchester, VA 22603

  Back on the market at no fault of seller. Seller is motivated and offering $5000 in closing costs assistance!! Seller is moving out of state. Welcome home to timeless charm with this beautiful 3-bedroom, 2–full-bath home, featuring stunning original woodwork that has been exceptionally well preserved. From the moment you enter, you’ll appreciate the character and craftsmanship that make this home

  Hailey Mooney Real Broker, LLC

  139 Bryarly Rd, Winchester, VA 22603
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  /2

  $409,900

  Coming Soon

  • 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

  $459,990

  New Construction $8K 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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  /25

  $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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  /18

  $382,990

  New Construction $25K PRICE DROP

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

  112 Sioux Loop, Winchester, VA 22602

  This Adams interior unit features 4 bedrooms, 3.5 baths, and a 1-car garage. With a total of 1,889 sq ft, there is plenty of space to entertain and live comfortably. Enjoy 9' ceilings and luxury vinyl plank flooring on the main level. The kitchen features white cabinets with quartz countertops along with stainless steel appliances by Whirlpool. Relax on your 8'x14' rear deck and take advantage of

  D.R. Horton Builder

  112 Sioux Loop, Winchester, VA 22602
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  /22

  $469,990

  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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  /45

  $220,000

  • 1 Bed
  • 1 Bath
  • 637 Sq Ft

  106 Blackfeet Trail, Winchester, VA 22602

  Charming mountain retreat nestled on a full acre in Shawneeland! This cozy 1-bedroom, 1-bath cabin offers the perfect blend of privacy, nature, and modern comfort. Situated on two combined lots totaling approximately 1 acre, the property provides plenty of space to enjoy the peaceful wooded setting.Recent improvements include a newer architectural shingle roof, gutter, vinyl clad double

  Tiffany Feathers-Brown MarketPlace REALTY

  106 Blackfeet Trail, Winchester, VA 22602
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  /36

  $385,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,601 Sq Ft

  13 E Leicester St, Winchester, VA 22601

  Incredible location, incredible home! Relax on the elevated front porch overlooking Leicester St, or retreat to the private back yard. Inside, gleaming wood floors and original trim compliment the new kitchen and bathrooms. HVAC, wiring, plumbing, windows, roofing, and siding have been lovingly replaced/updated in the last 5 years. This home is walkable to everything, and sits on a calm side

  William Steinmetz RE/MAX Roots

  13 E Leicester St, Winchester, VA 22601
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  /15

  $391,990

  New Construction

  • 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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  /16

  $390,790

  New Construction

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

  2435 Coriander Dr, Winchester, VA 22603

  Brand-New 4-Bedroom End Unit—Late Summer Move-In!Step into modern living with this stylish new-construction end-unit townhome, ideally located just steps from Snowden Bridge’s newest amenities. An entry-level bedroom with full bath offers the perfect setup for guests, multigenerational living, or added flexibility.Upstairs, light-filled open-concept living shines, with a sleek kitchen

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  2435 Coriander Dr, Winchester, VA 22603
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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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  /96

  $489,900

  • 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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  /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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  /23

  $319,900

  Open Sat 1PM - 3PM $5K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,154 Sq Ft

  151 Mccormick Cir Unit 105, Winchester, VA 22602

  Welcome to refined 55+ living in the highly sought-after Winchester Landing Commons. This exceptional ground-floor residence offers two bedrooms and two full baths, showcasing model-quality finishes and sun-drenched interiors with beautiful views. Designed for both comfort and convenience, this unit features a rare private entrance in addition to the main building access. The thoughtfully

  Mike Campbell EXP Realty, LLC

  151 Mccormick Cir Unit 105, Winchester, VA 22602
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  /24

  $324,900

  New Construction $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,152 Sq Ft

  212 Falcon Trail, Winchester, VA 22602

  Nearing completion! 1/3 Acre – No Carpet!This affordable 2-bed, 2.5-bath home offers high-end finishes and incredible growth potential.Premium Finishes: Hardwood floors throughout (including all bedrooms), tile in all baths, and granite kitchen countertops.Open Layout: Bright family room and a spacious kitchen/dining area perfect for entertaining.Owner’s Suite: Large master

  Jim Thomson Realty ONE Group Old Towne

  212 Falcon Trail, Winchester, VA 22602
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  /40

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft

  167 Falcon Trail, Winchester, VA 22602

  Discover the perfect blend of comfort and charm of this contemporary home nestled on a large 0.69-acre lot in Shawneeland! Built in 2007, this inviting residence features 1,470 finished square feet of thoughtfully designed living space, plus a spacious unfinished walk-out basement ready for your imagination and finishing touches! Step inside to find a warm and welcoming atmosphere within this

  Bridget Aikens Colony Realty

  167 Falcon 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
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  /33

  $399,000

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  1025 S Loudoun St, Winchester, VA 22601

  TONS OF UPGRADES! This home has been updated top to bottom. From the roof, windows, kitchen, bathrooms, light fixtures, HVAC, and so on. Located just 1 block from Handley High School, this home and all of its high end improvements make it a treasure waiting to be discovered. As you walk through this home you'll notice that a ton of care and thoughtfulness was put into what it is today. The

  Michael Sprague Samson Properties

  1025 S Loudoun St, Winchester, VA 22601
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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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  /65

  $365,000

  New Construction

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

  805 Pheasant Dr, Winchester, VA 22602

  Welcome to this newly built (2026) ranch in Wilde Acres situated on .50-acre lot nestled among the trees Upon entry, enjoy the open living area and luxury Vinyl plank floor which make the space warm and comfortable. The galley kitchen offers ample counterspace and new stainless-steel appliances. The convenient main level. Upstairs there are three spacious bedrooms and a two full bath. Outside the

  Alexandra Brown Spring Hill Real Estate, LLC.

  805 Pheasant Dr, Winchester, VA 22602
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  /30

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,280 Sq Ft

  540 Bellview Ave, Winchester, VA 22601

  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 for indoor-outdoor

  Heloisa Amar Samson Properties

  540 Bellview Ave, Winchester, VA 22601
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  /45

  $449,000

  $56K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft

  3137 Eton Place, Winchester, VA 22601

  Welcome to The Lofts at Creekside! Better than new and absolutely breathtaking, this four-level interior townhome delivers style, space, and an unbeatable lifestyle—all within walking distance to top-rated restaurants, shopping, and the historic Kernstown Battlefield. Offering 3 bedrooms and 2.5 baths, the home features a chic upper-level loft that opens to a stunning private terrace, perfect for

  Laura White ERA Oakcrest Realty, Inc.

  3137 Eton Place, Winchester, VA 22601
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  /10

  $255,000

  $10K PRICE INCREASE

  • 2 Beds
  • 2.5 Baths
  • 1,280 Sq Ft

  2967 Sorrell Ct, Winchester, VA 22601

  This diamond in the rough has solid bones and plenty of potential for the right buyer. The HVAC system is only two years old, the water heater is brand new, and both full bathrooms have already been updated. The home could use some fresh paint, and the dishwasher is currently not working, but the major systems are in great shape—making this an excellent opportunity for a starter home or

  Jamie Cook Treck Realty LLC

  2967 Sorrell Ct, Winchester, VA 22601
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  /46

  $369,900

  • 4 Beds
  • 3 Baths
  • 2,362 Sq Ft

  300 Elk Trail, Winchester, VA 22602

  Looking for a newer home with room to spread out and a peaceful wooded setting? Welcome to 300 Elk Trail. Built in 2021 and tucked among the trees in the Mountain Falls/Wilde Acres area, this 4-bedroom, 3-bath home offers the perfect blend of modern convenience and country living. The open main level creates a welcoming space for gathering with family and friends, while the finished lower level

  Abby Walters Preslee Real Estate

  300 Elk Trail, Winchester, VA 22602
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  /32

  $389,900

  $9K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,842 Sq Ft

  3138 Eton Place, Winchester, VA 22601

  Beautiful, just like brand new, 3 bedroom 2.5 bath end unit townhome located in The Lofts at Creekside! Walking distance to local restaurants and shopping here in Creekside. Home features large kitchen island, stainless steel appliances, and luxury vinyl plank flooring, private balcony, surrounded by open floor plan which provides for great entertainment. Nice upgrades all throughout the house!

  Christopher Hild Realty FC, LLC

  3138 Eton Place, Winchester, VA 22601
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  /78

  $425,000

  $70K PRICE DROP

  • Land
  • 20 Acres
  • $21,250 per Acre

  000 Light Rd, Winchester, VA 22603

  Gentle stretches of open meadow roll into quiet, wooded groves where sunlight filters through the trees. Hidden among them, peaceful little ponds shimmer like jewels, inviting you to pause and simply breathe. Imagine sundrenched mornings, afternoons exploring your own private trails, and evenings watching the sky glow across wide open fields. Whether you long to build a cozy retreat, a forever

  Melissa Johnston ERA Oakcrest Realty, Inc.

  000 Light Rd, Winchester, VA 22603
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  /2

  $275,000

  • Land
  • 5 Acres
  • $55,000 per Acre

  341 Laurel Grove Rd, Winchester, VA 22602

  THERE ARE 2 -5 ACRE BUILDING LOTS W/4 BR CONVENTIONAL PERKS APPROVED. LOTS 3 AND 4. THESE LOTS ARE CREATED FROM A LARGER PARCEL BY WAY OF A BOUNDRY LINE ADJUSTMENT. NEW DEEDS WILL BE ISSUED AT CLOSING. SEPERATE TAX ASSESSMENTS ARE UNAVAILABLE BUT APPRAISALS ARE AVAILABLE FOR BOTH LOTS. LISTING PRICE IS PER LOT. WILL BUILD TO SUIT.

  Barbara Singhas Crum Realty, Inc.

  341 Laurel Grove Rd, Winchester, VA 22602
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  /31

  $398,000

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft

  103 Elaine Dr, Winchester, VA 22602

  This is the one you’ve been waiting for — a beautifully maintained ranch‐style home with thoughtful updates and a bright, comfortable layout throughout. A newer roof, updated HVAC, and fresh carpet provide peace of mind and move‐in readiness from day one.The primary ensuite serves as a true retreat, featuring a spa‐like bath and a walk‐in closet. Two additional bedrooms offer flexible living

  LESLIE WEBB Long & Foster Real Estate, Inc.

  103 Elaine Dr, Winchester, VA 22602
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  /37

  $399,900

  • 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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