Winchester County VA Homes for Sale

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  $2,300,000

  • Land
  • 3.51 Acres
  • $655,271 per Acre

  1721 Amherst St, Winchester, VA 22601

  3.51 AC of premier commercial land. Directly across the street from the main hospital campus on one of Winchester's main commercial corridors. Ideal for banks, medical offices, retail or restaurants.

  Marie DiLorenzo Oakcrest Commercial LLC.

  1721 Amherst St, Winchester, VA 22601
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  $269,900

  • 2 Beds
  • 1.5 Baths
  • 1,251 Sq Ft

  2918 Sorrell Ct, Winchester, VA 22601

  Welcome to your new home! This beautifully maintained 2 -bedroom, 1.5 bath townhome offers comfort, convenience, and style in a great location. On the main level you will find a spacious kitchen with ample cabinetry and a breakfast area, the living room offers plenty of natural light, off the living room is a convenient half bath. Upstairs you will find two generously sized bedrooms with large

  Amber Jenkins Century 21 Redwood Realty

  2918 Sorrell Ct, Winchester, VA 22601
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  /20

  $323,000

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft

  553 Highland Ave, Winchester, VA 22601

  MOTIVATED SELLER - price reduction of $11,000 - bring all offers! One Way street = quiet Gorgeous Rehab - you have to see it! Secure Parking off the alley Efficient HVAC mini splits installed Washer and Dryer included

  Teri Domanski Corcoran McEnearney

  553 Highland Ave, Winchester, VA 22601
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  /19

  $299,500

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  106 W Southwerk St, Winchester, VA 22601

  Charming 3 bedroom, 1.5 bath colonial just blocks from downtown Winchester! Enjoy a covered front porch perfect for relaxing and a spacious rear deck for entertaining. Inside, you’ll find inviting spaces with newer windows throughout. Conveniently located near shopping, restaurants, entertainment, the local library, and Jim Barnett Park—this home offers both comfort and an unbeatable location!

  Sheila Pack RE/MAX Roots

  106 W Southwerk St, Winchester, VA 22601
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  $449,990 New Construction

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

  1819 Reese Ct, Winchester, VA 22601

  1819 Reese Court is a move-in ready 3-level townhome with full brick front in Winchester, VA. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained oak stairs lead you to the main level with LVP flooring. The kitchen is equipped with beautiful quartz countertops, sasparilla cabinets, and stainless-steel appliances. The upper

  D.R. Horton Builder

  1819 Reese Ct, Winchester, VA 22601
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  /17

  $389,990

  • 3 Beds
  • 3.5 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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  /11

  $1,100,000

  • Land
  • 2.83 Acres
  • $388,693 per Acre

  2725 S Pleasant Valley Rd, Winchester, VA 22601

  Location, location, location. Here is your chance to own one of the few commercial/industrial lots located in the highly desirable Winchester City. This cleared, blank slate is ready for your next business endeavor. Currently zoned as CM-1 (Commercial/Industrial), the property offers roughly 465 ft of prime road frontage, perfect for displaying your establishment.Current use regulations

  Kaitlyn Behr RE/MAX Roots

  2725 S Pleasant Valley Rd, Winchester, VA 22601
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  $459,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,920 Sq Ft

  1805 Harvest Dr, Winchester, VA 22601

  1805 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for January move-in. Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel appliances. The

  D.R. Horton Builder

  1805 Harvest Dr, Winchester, VA 22601
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  $635,000

  • 4 Beds
  • 3.5 Baths
  • 4,632 Sq Ft

  930 Wayne Dr, Winchester, VA 22601

  Beautiful brick-front Colonial in a prime location! Nestled in a quiet neighborhood yet just minutes from I-81 and local amenities, this stunning home offers the perfect blend of convenience and tranquility.Step into the grand two-story foyer, flanked by a formal living room and dining room accented with elegant columns and a cozy fireplace. To the right, you’ll find a spectacular

  Elizabeth Flood Keller Williams Realty

  930 Wayne Dr, Winchester, VA 22601
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  /43

  $489,900

  • 3 Beds
  • 4 Baths
  • 3,359 Sq Ft

  227 Miller St, Winchester, VA 22601

  Welcome to 227 Miller Street — a home that instantly feels inviting. Recent improvements include new flooring in both upstairs and downstairs bathrooms (2025), new toilets in all bathrooms (2024), refreshed hardwood floors (2025), a professionally cleaned chimney (2025), a new sump pump (2025), and a fully dug-out and waterproofed basement completed in 2025. The back deck was replaced in 2024,

  Leah Marabella Realty ONE Group Old Towne

  227 Miller St, Winchester, VA 22601
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  /2

  $850,000 Coming Soon

  • 4 Beds
  • 4 Baths
  • 4,417 Sq Ft

  1006 Armistead St, Winchester, VA 22601

  This spacious 4-bedroom, 4-bath home is full of opportunity for buyers ready to make it their own. Priced below tax value, it’s a rare find for those looking to build equity while creating the home of their dreams. Featuring a generous floor plan with a two-story foyer, hardwood floors on the main level, and a large family room with a fireplace, the home provides a solid foundation for future

  Chris Craddock EXP Realty, LLC

  1006 Armistead St, Winchester, VA 22601
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  /2

  $409,990 New Construction

  • 3 Beds
  • 2 Baths
  • 2,060 Sq Ft

  Deep Creek II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

  The Largest New Construction Townhome In Winchester! Attached 1-car garage or flex option. Open concept kitchen with optional island opens to country kitchen, sun room, and living room. Alternative main level option available. Optional choices available include a study and a fireplace. Owner’s suite with a generous walk-in closet, dual vanity, and seated shower. Four-foot rear extension

  DRB Homes Builder

  0 Tbd Weems Ln Unit 38608305, Winchester, VA 22601
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  /21

  $384,880 Open Sat 12PM - 4PM

  • 3 Beds
  • 4 Baths
  • 1,989 Sq Ft

  105 Boone Ct, Winchester, VA 22602

  Move in ready at Rossum Crossing townhome community, conveniently located near shopping and dining options. The St. Paul Townhome features three bedrooms, two and a half baths, and a one-car garage. The main floor boasts an open-concept floor plan, with a spacious family room that flows into a fully equipped kitchen. The kitchen includes an island, a pantry closet, and a breakfast nook. This

  Dorelba Estrada New Home Star Virginia, LLC

  105 Boone Ct, Winchester, VA 22602
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  /41

  $355,000

  • 4 Beds
  • 2.5 Baths
  • 2,804 Sq Ft

  513 van Fossen St, Winchester, VA 22601

  Welcome to 513 Van Fossen St, a beautifully updated 4-bedroom, 2.5-bathroom brick ranch conveniently located just minutes from downtown Winchester. Step inside to discover freshly refinished original red oak hardwood floors (locally sourced from Plumly Lumber) in a warm Golden Pecan finish (2025). The home boasts fresh paint inside and out, a brand-new roof (2025), and newer HVAC. The living room

  Amy Longerbeam RE/MAX Roots

  513 van Fossen St, Winchester, VA 22601
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  $375,900

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  2116 Stoneleigh Dr, Winchester, VA 22601

  New roof and decking make this Orchard Hill town home a great buy—Hardwood floors, a fireplace in the family room, along with built-in cabinets and bookshelves: full walk-out basement and large yard.

  John Schroth Colony Realty

  2116 Stoneleigh Dr, Winchester, VA 22601
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  /2

  $399,000

  • 10 Beds
  • 6 Baths
  • 12,128 Sq Ft

  910 Franklin St, Winchester, VA 22601

  What a remarkable and unique opportunity!Assessed for $571630.00 Brand new roof on entire building, newly demolished warehouse has made way to enormous area for expansion and or parking. SOOO MUCH potential - Upper level has two apartments -However only one is approved for rental unitLower level is ready for its new transformation as residential or allowed commercial use - Conditional use

  Pakeeza Akhtar The KOR Group, Inc.

  910 Franklin St, Winchester, VA 22601
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  /16

  $299,990

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

  405 1/2 Elm St, Winchester, VA 22601

  This is a two level house 3 bedrooms 2 full bathrooms good for fist time buyers or investment property, ready to move in , house is sold as is. Thank you for showing.

  Virgilio & Maria Vasquez The Vasquez Group LLC

  405 1/2 Elm St, Winchester, VA 22601
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  /23

  $279,000

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft

  208 Shenandoah Ave, Winchester, VA 22601

  Welcome home to 208 Shenandoah Ave in Winchester, VA! This updated ranch home offers the coveted simplicity of easy, one-level living and is perfectly situated in a prime, convenient Winchester location. Featuring 3 bedrooms and 1 full bath, the interior is turn-key with newer flooring and fresh paint throughout. The living spaces are bright and inviting with lots of natural light, creating a

  Dan Whitacre Colony Realty

  208 Shenandoah Ave, Winchester, VA 22601
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  $409,990 New Construction

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

  Adams Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

  The Adams I townhome offers 1,889 sq. ft. of thoughtfully designed living space, featuring 4 bedrooms, 3.5 bathrooms, and a convenient 1-car front-load garage. The modern kitchen showcases quartz countertops, stainless steel appliances, a spacious island, recessed lighting, and upgraded cabinets. Enjoy the flexibility of a finished lower-level bonus space—perfect for a rec room, home office, or

  D.R. Horton Builder

  1831 Reese Ct Unit 37025140, Winchester, VA 22601
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  $449,900

  • 4 Beds
  • 1.5 Baths
  • 1,932 Sq Ft

  420 W Cork St, Winchester, VA 22601

  Discover the perfect blend of historic charm and modern convenience at 420 W Cork Street. This captivating four-level brick home offers 4 bedrooms and 1.5 baths, boasting beautiful hardwood floors, gorgeous trim and plenty of space for you and yours. The main level offers a spacious living room, dining room and kitchen. Upstairs you will find 4 sizable bedrooms and a full bath. The top level is a

  Dan Whitacre Colony Realty

  420 W Cork St, Winchester, VA 22601
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  /14

  $441,700

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  421 Superior Ave, Winchester, VA 22601

  Renovated and move in ready! Let's start with the new mailbox, new 16' wide asphalt driveway, new 8'x13' concrete patio for you to enjoy watching the sun sets overlooking the large back yard., The carport even has bolts in ceiling for you to install a swing. Then inside, new heat pump and central a/c system, new appliances with fingerprint resistant stainless-steel exterior, stainless steel liner

  Leo Smith CENTURY 21 New Millennium

  421 Superior Ave, Winchester, VA 22601
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  /24

  $265,000

  • 2 Beds
  • 1 Bath
  • 882 Sq Ft

  204 Shenandoah Ave, Winchester, VA 22601

  Great opportunity to own this 2-bed, 1-bath Winchester City charmer that sits just minutes from Shenandoah University and the Old Town walking mall. Main level living with a bright comfortable living area, an eat-in kitchen home that includes a bonus room providing flexible space for an office, playroom, fitness area, or guest room, central air and the convenience of an in-home washer & dryer

  Janet Flaherty Keller Williams Realty

  204 Shenandoah Ave, Winchester, VA 22601
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  $459,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,905 Sq Ft

  Adams II Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

  The Adams II townhome features 1,905 sq. ft. of stylish and flexible living space, including 4 bedrooms, 3.5 bathrooms, and a 1-car rear-load garage. The gourmet kitchen is equipped with quartz countertops, stainless steel appliances, recessed lighting, a generous island, and sleek Duraform cabinetry. The lower-level bonus room offers endless possibilities—use it as a rec room, home office, or an

  D.R. Horton Builder

  1831 Reese Ct Unit 37025141, Winchester, VA 22601
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  $654,000

  • Studio
  • 3,511 Sq Ft

  1400 Valley Ave, Winchester, VA 22601

  Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both

  Danielle Spriggs Real Broker LLC

  1400 Valley Ave, Winchester, VA 22601
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  /19

  $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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  $396,500

  • 3 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  31 W Whitlock Ave, Winchester, VA 22601

  Charming Home Near Handley High School – Move-In Ready! Welcome to this beautifully updated home in a fantastic downtown location—just a short walk to shops, restaurants, and all that the vibrant city center has to offer. This property features a converted garage that now serves as a versatile studio space, perfect for a home office, art studio, or guest suite. Enjoy a spacious, fenced-in

  Meridee Powars Link Realty Services LLC

  31 W Whitlock Ave, Winchester, VA 22601
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  $299,990

  • 3 Beds
  • 1 Bath
  • 1,205 Sq Ft

  627 Watson Ave, Winchester, VA 22601

  CLASSIC CHARM MEETS CONTEMPORARY COMFORT IN THIS FANTASTIC DUPLEX UNIT! This charming Winchester duplex unit seamlessly blends timeless character with modern conveniences, offering the perfect balance of historic flair and contemporary living. Nestled just minutes from the vibrant heart of downtown Winchester, this inviting property combines an unbeatable location with a thoughtfully-updated

  Kristin Crosby Samson Properties

  627 Watson Ave, Winchester, VA 22601
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  /35

  $459,990 New Construction

  • 4 Beds
  • 3 Baths
  • 1,939 Sq Ft

  1817 Harvest Dr, Winchester, VA 22601

  1817 Harvest Drive is an attractive new 3 level townhome with full brick front in Winchester, VA for January move-in. Our modern Adams II floorplan features a 1-car garage, and a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel appliances. The

  D.R. Horton Builder

  1817 Harvest Dr, Winchester, VA 22601
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  /43

  $849,990

  • 5 Beds
  • 4.5 Baths
  • 5,254 Sq Ft

  1504 Brookdale Ct, Winchester, VA 22601

  This home generates income from solar energy sales averaging over $2k a year! The Solar panels and system are OWNED by the homeowner NOT leased. There are no monthly fees or payments for the system. System is “Grandfathered” with a licensing agreement that allows homeowner to sell excess electricity produced. Lower your energy costs and receive cash earnings! Recent updates over $40k in this

  Julie Shiley Coldwell Banker Realty

  1504 Brookdale Ct, Winchester, VA 22601
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  $500,000

  • 3 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  236 Miller St, Winchester, VA 22601

  Charming 3-Bedroom/ 2.5 Bath Colonial just blocks from Old Town Winchester, offering easy access to dining, entertainment, and shopping! This home offers classic charm and everyday comfort with a covered front porch, fenced backyard, and rear patio—perfect for relaxing or entertaining. A 2-car detached garage (with electric), off-street parking, and attractive landscaping enhance both

  Sheila Pack RE/MAX Roots

  236 Miller St, Winchester, VA 22601
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  $429,990 New Construction

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

  1822 Blythe Way, Winchester, VA 22601

  1822 Blythe Way is an attractive new 3 level end townhome with full brick front in Winchester, VA for January move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, white cabinets, and stainless-steel

  D.R. Horton Builder

  1822 Blythe Way, Winchester, VA 22601
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  /43

  $459,000

  • 3 Beds
  • 2 Baths
  • 2,648 Sq Ft

  1332 Ramseur Ln, Winchester, VA 22601

  Welcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exterior condo offering 3 bedrooms and 2 full baths. Rich hardwood floors flow throughout the home. The primary bedroom includes a cozy fireplace perfect for relaxing evenings. Updated appliances, such as washer, dryer, refrigerator, stove and microwave. Enjoy the ease of your own private elevator within the

  James King RE/MAX Roots

  1332 Ramseur Ln, Winchester, VA 22601
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  $330,000

  • 3 Beds
  • 1 Bath
  • 1,237 Sq Ft

  117 W Oates Ave, Winchester, VA 22601

  This charming bungalow, nestled in the heart of the Arthur C Oates Estate, offers a delightful blend of comfort and community. Built in 1953, this home features 3 cozy bedrooms, 1 full bathrooms, and an upstairs loft perfect for relaxation. The inviting kitchen is equipped with essential appliances, including a single oven and refrigerator, making meal preparation a breeze. The unfinished

  Jeffrey Konrady Realty ONE Group Old Towne

  117 W Oates Ave, Winchester, VA 22601
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  $289,500

  • 4 Beds
  • 1 Bath
  • 1,732 Sq Ft

  1006 S Cameron St, Winchester, VA 22601

  Welcome home to this charming 4-bedroom, 1-bath colonial perfectly situated with walking distance from downtown Winchester. Warm hardwood floors flow throughout the home, complemented by a large covered front porch and a spacious rear deck—ideal for morning coffee or evening gatherings. Recent updates include a new water heater (2025), new water tank (2025), and an updated furnace and bath for

  Laura White ERA Oakcrest Realty, Inc.

  1006 S Cameron St, Winchester, VA 22601
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  $434,990 New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,923 Sq Ft

  1818 Blythe Way, Winchester, VA 22601

  1818 Blythe Way is an attractive new 3-level townhome with full brick front in Winchester, VA scheduled for a November move-in. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained Oak stairs lead you to the main level with LVP Floors. The kitchen is equipped with beautiful quartz countertops, sarsaparilla cabinets, and

  D.R. Horton Builder

  1818 Blythe Way, Winchester, VA 22601
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  /22

  $300,000

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  534 N Kent St, Winchester, VA 22601

  Just minutes from the downtown walking mall, this single family home offers three bedrooms, stainless steel appliances and granite countertops, a great yard, off street parking, and a front porch. The home comes with an electric car charger usable for all brands.

  Katie Landi Jordan Samson Properties

  534 N Kent St, Winchester, VA 22601
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  /29

  $289,900

  • 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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  /25

  $600,000

  • 5 Beds
  • 4 Baths
  • 3,550 Sq Ft

  681 Hillman Dr, Winchester, VA 22601

  No HOA and only two years young, this beautifully designed and meticulously maintained home offers the perfect blend of comfort, style, and modern functionality. A rare main-level bedroom with a full bath provides flexibility and convenience for guests or multi-generational living. Throughout the home, designer finishes and elegant details elevate every space, including a spa-inspired bathroom

  Sarah Reynolds Keller Williams Realty

  681 Hillman Dr, Winchester, VA 22601
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  /11

  $269,000

  • 2 Beds
  • 1.5 Baths
  • 1,116 Sq Ft

  518 Yorktowne Place, Winchester, VA 22601

  This exquisite end-of-row townhouse, underwent a major renovation in 2025, offers a perfect blend of modern luxury and timeless comfort. With two spacious bedrooms and one and a half elegantly appointed bathrooms, this home is designed for both relaxation and entertaining. Step inside to discover a gourmet kitchen that will inspire your culinary adventures. Featuring upgraded granite countertops,

  Brandon Pifer Pifer Realty, LLC

  518 Yorktowne Place, Winchester, VA 22601

Showing Results 41 - 79, Page 2 of 2