Winchester County VA Homes for Sale

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  /86

  $559,900

  Open House 8/16

  • 2 Beds
  • 2.5 Baths
  • 2,031 Sq Ft

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601

  Experience a rare opportunity to own a piece of Winchester history at The Fort, one of Old Town's most distinctive residential communities. Located just blocks from the vibrant Walking Mall, this beautifully renovated 2-bedroom, 2.5-bath condominium seamlessly blends historic character with modern luxury. Unit 105 features an open-concept floor plan with soaring ceilings, rich architectural

  Jen Richards MarketPlace REALTY

  411-U105 N Loudoun St Unit 105, Winchester, VA 22601
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  /33

  $348,000

  $12K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  302 Wentworth Dr, Winchester, VA 22601

  Enjoy one-level living in this spectacularly located brick rambler, nestled in a quiet residential neighborhood while remaining conveniently close to Route 11 with easy access to I-81. The property currently has a long term month-to-month tenant paying under market value, offering flexibility for an owner-occupant or an investor seeking rental income with potential for increased rent. Situated on

  Heloisa Amar Samson Properties

  302 Wentworth Dr, Winchester, VA 22601
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  /5

  $295,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 913 Sq Ft

  405 Shenandoah Ave, Winchester, VA 22601

  Ideally situated just minutes from I-81 and a short drive to historic Old Town Winchester, this centrally located rambler offers both convenience and investment potential. Situated on a desirable corner lot, the property features a fenced yard and a storage shed for added functionality. The home has been recently refreshed with new paint and landscaping, providing excellent curb appeal and a

  Heloisa Amar Samson Properties

  405 Shenandoah Ave, Winchester, VA 22601
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  /26

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,737 Sq Ft

  614 Sherlock Trace, Winchester, VA 22601

  **Excellent Opportunity in the Heart of Winchester!** Don't miss the chance to own a well-located home in one of Winchester's most convenient areas. Situated on a quiet street, this property offers easy access to shopping, dining, schools, parks, and major commuter routes—everything that matters is just minutes away. Featuring **3 bedrooms** plus **two additional versatile rooms**, this home

  

  Carlos Soares

  Samson Properties

  614 Sherlock Trace, Winchester, VA 22601
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  /46

  $1,150,000

  • 5 Beds
  • 5 Baths
  • 5,695 Sq Ft

  801 Armistead St, Winchester, VA 22601

  This home has a 2.25% VA Assumable Loan. There are homes that simply provide shelter. And then there are homes like this—homes that make you slow down, take a deep breath, and picture the life you've been working so hard to create. Nestled in one of Winchester's most beloved neighborhoods, this stately residence blends timeless elegance with the confidence that comes from knowing the important

  Donna Chong Samson Properties

  801 Armistead St, Winchester, VA 22601
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  /27

  $359,900

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  601 Gray Ave, Winchester, VA 22601

  Welcome to Gray Avenue! This beautifully updated 3-bedroom, 2-bath home offers over 1,700 square feet of stylish living space, blending timeless charm with modern finishes throughout. Rich hardwood floors flow throughout the home, creating warmth and character from the moment you step inside. The sun-filled living room feels bright and inviting, highlighted by a custom light fixture and a

  

  Walther Vasquez Johnson

  Samson Properties

  601 Gray Ave, Winchester, VA 22601
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  /34

  $359,900

  $5K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  621 Patterson Ave, Winchester, VA 22601

  Enchanting Cape Cod in an ideal in‐town location, this home has a welcoming ease to it, offering 3–4 bedrooms and 2.5 bathrooms with a layout that adapts beautifully to everyday living. The main level includes two convenient bedrooms, a comfortable, light‐filled living room, a separate dining area, and a renovated kitchen featuring new cabinets and stainless‐steel appliances.In 2021, the home

  LESLIE WEBB Long & Foster Real Estate, Inc.

  621 Patterson Ave, Winchester, VA 22601
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  /42

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft

  703 S Loudoun St, Winchester, VA 22601

  ***4.25% INTEREST RATE AVAILABLE*** Located in the heart of Winchester’s Historic District, this remarkable property offers a rare opportunity to own a piece of the city’s rich architectural heritage just moments from vibrant Old Town Winchester. Blending timeless character with flexible living options, the home showcases classic historic charm paired with thoughtful updates that support today’s

  John Ginty Samson Properties

  703 S Loudoun St, Winchester, VA 22601
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  /6

  $370,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1845 Rosser Ln, Winchester, VA 22601

  Beautifully maintained 2-bedroom, 2-bath Ranch home in the desirable Willow Lawn Cottages 55+Community. The main-level features an open floor plan, vaulted ceiling, ceiling fan, gas fireplace, largeconcrete patio, and 1-car garage. 2026 updates include a new HVAC system. The primary suite offers awalk-in closet, private full bath, and laundry. Low maintenance living includes lawn and

  Derek Greene The Greene Realty Group

  1845 Rosser Ln, Winchester, VA 22601
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  /32

  $399,900

  $29K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,419 Sq Ft

  118 1/2 E Cork St, Winchester, VA 22601

  Seeking the perfect blend of historic character and modern urban living? This exceptional Urban Lofts Condominium is just one and a half blocks from Old Town Winchester Walking Mall, offering easy access to restaurants, boutiques, entertainment, and vibrant downtown living. Originally built in the early 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural

  Janet Flaherty Keller Williams Realty

  118 1/2 E Cork St, Winchester, VA 22601
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  /29

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,734 Sq Ft

  11 W Germain St, Winchester, VA 22601

  Back on the Market!...Beautifully located in the heart of Historic Winchester, this charming home offers 2 bedrooms, 1 full bath, and a versatile bonus room on the second floor-perfect for an office, guest space, or hobby room. Enjoy the convenience of being within walking distance to downtown Winchester's shops, restaurants, entertainment, and the famous Apple Blossom Festival festivities.

  Magnolia Halkowitz ERA Oakcrest Realty, Inc.

  11 W Germain St, Winchester, VA 22601
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  /46

  $339,000

  $21K PRICE DROP

  • 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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  /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
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  /34

  $359,900

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,219 Sq Ft

  1856 Melvor Ln, Winchester, VA 22601

  Welcome to easy living at 1856 Melvor Lane! Perfectly positioned on a desirable corner lot in a welcoming 55+ community, this beautifully updated one-level home offers the ideal combination of comfort, style, and low-maintenance living. Step inside to discover an airy open floor plan enhanced by soaring cathedral ceilings and abundant natural light. Thoughtful updates—including luxury vinyl plank

  Natasha Roberts Realty ONE Group Old Towne

  1856 Melvor Ln, Winchester, VA 22601
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  /10

  $268,000

  $22K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 817 Sq Ft

  580 York Ave, Winchester, VA 22601

  **PRICE REDUCTION**Please contact Maria Vasquez for inquiries as the co-listing agent. (571)334-5118. This charming bungalow in the heart of the City of Winchester has already been beautifully renovated, offering the perfect blend of classic charm and modern living. Featuring 2 cozy bedrooms and a full bathroom, the home is designed with comfort and functionality in mind. Enjoy an updated

  Yoselin Mejia The Vasquez Group LLC

  580 York Ave, Winchester, VA 22601
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  /21

  $262,000

  $7K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  321 N Kent St, Winchester, VA 22601

  Attention investors...24 month lease in place and new HVAC! Wonderful opportunity to own in downtown Winchester! Walking distance to the Old Town Mall restaurants, shopping, the library and more. Easy access to Rt. 7 and 81. The main level has a nice open floor plan, consisting of kitchen, dining and living areas. The main level also features a half bath and bonus room, perfect for an office or

  Amy Capitano MarketPlace REALTY

  321 N Kent St, Winchester, VA 22601
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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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  /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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  /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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  /50

  $1,179,000

  • 4 Beds
  • 5 Baths
  • 4,970 Sq Ft

  1004 Heth Place, Winchester, VA 22601

  Stepping onto the Southern style covered front porc.h you enter the large foyer with a Schoenbek chandelier. There is a living room to the left which opens to a separate dining room with a hand painted blue and gold ceiling. The kitchen is eating size with granite counter and large island. Double doors lead to a small back porch and stairs to the patio. The first floor family room has a gas

  Kathryn Hallett Long & Foster Real Estate, Inc.

  1004 Heth Place, Winchester, VA 22601
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  /22

  $269,000

  • Land
  • 42,253 Sq Ft
  • $277,320 per Acre

  823 Armistead St, Winchester, VA 22601

  *** Price shown is for lot only. Seller is willing to assist Buyer in building this beautiful home plandesigned by Seller customized for this lot and optimized for cost effective construction. Closingon the lot may occur upon issuance of the Building Permit in Buyer’s name by the City ofWinchester. ***This modern farmhouse style home includes 5,630 square feet of living space

  Janet Flaherty Keller Williams Realty

  823 Armistead St, Winchester, VA 22601
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  /34

  $359,000

  $30K PRICE DROP

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

  328 Longview Ave, Winchester, VA 22601

  Price Reduced $15,000! Highly Motivated Seller! Welcome to this meticulously maintained, 3 bedroom, move-in-ready ranch home located within Winchester City limits. Perfectly situated on a premium, near-half-acre lot (.46 acres) off Papermill Road, this property offers the ultimate blend of city convenience and peaceful privacy with no backyard neighbors. Kitchen and downstairs bathroom to be

  Kelly Bauer Coldwell Banker Premier

  328 Longview Ave, Winchester, VA 22601
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  /59

  $539,900

  $35K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  660 Beehive Way, Winchester, VA 22601

  Enjoy city living in this spacious and light-filled home featuring 5 bedrooms and 3.5 baths. Fresh new carpeting has been installed on the upper level and in the family room, complemented by hardwood floors throughout the main living areas. The kitchen is equipped with stainless steel appliances, double ovens, and a center island—perfect for cooking and entertaining. Formal living and dining

  Traci Shoberg Samson Properties

  660 Beehive Way, Winchester, VA 22601
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  /34

  $339,900

  $10K 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
• 

  

  /23

  $419,990

  New Construction

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

  126 Swansong Place, Winchester, VA 22603

  Exceptional value for a 4‐bedroom END‐UNIT townhome is ready for move‐in! Brand‐new construction offers modern style and comfort with oak stairs with upgraded railings and durable LVP flooring throughout the main level. Backing to open space in the newest section of Snowden Bridge, this spacious home includes a flexible entry‐level bedroom with full bath, a bright open‐concept main living area,

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  126 Swansong Place, Winchester, VA 22603
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  /51

  $390,000

  $10K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,011 Sq Ft

  605 Dunlap St, Winchester, VA 22601

  Priced to reflect the need for some updating, this home offers opportunities and personalization while remaining move-in ready 1011sf total living space.This home is in very good shape. The sellers are selling this property completely As-IS. NO HOA Perfectly home on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2 full-bathroom home offers both seclusion and incredible

  Alexandra Brown Spring Hill Real Estate, LLC.

  605 Dunlap St, Winchester, VA 22601
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  /30

  $379,900

  • 2 Beds
  • 1.5 Baths
  • 1,186 Sq Ft

  711 E Cork St, Winchester, VA 22601

  This stunning property boasts a brand-new kitchen with quartz countertops, new appliances (refrigerator, microwave, stove) and a fresh new look. The laundry room got an upgrade too, with brand-new appliances. Newly installed waterproof vinyl flooring that's been laid down throughout, perfect for any occasion. Also, with a fresh coat of paint on the walls including the garage along with the door.

  Marco Novillo Spring Hill Real Estate, LLC.

  711 E Cork St, Winchester, VA 22601
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  /36

  $320,000

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

  115 S Purcell Ave, Winchester, VA 22601

  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. Open House on Sunday, August 16th from 1-4pm.

  Matthew Berry MarketPlace REALTY

  115 S Purcell Ave, Winchester, VA 22601
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  /33

  $447,000

  Open Sun 1PM - 4PM $3K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  310 Longview Ave, Winchester, VA 22601

  Discover a stunning blend of Colonial and Contemporary architecture in this exquisite 3-bedroom, 2.5-bathroom residence, built in 2024. Step inside to find luxurious vinyl plank flooring and plush carpeting that exude warmth and sophistication. The gourmet kitchen is a chef's dream, equipped with high-end appliances including a sleek wall oven, cooktop, and energy-efficient refrigerator, ensuring

  Dave Milburn Coldwell Banker Realty

  310 Longview Ave, Winchester, VA 22601
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  /62

  $760,000

  $39K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 4,438 Sq Ft

  769 Seldon Dr, Winchester, VA 22601

  Welcome to 769 Seldon Drive—an elegant brick-front colonial situated on nearly half an acre in one of Winchester’s most desirable neighborhoods. Offering over 4,500 finished square feet, this spacious 5-bedroom, 4.5-bath home is designed for comfort, flexibility, and multi-generational living. The main level features a generously sized primary suite with a walk-in closet and en-suite bath, along

  Amanda Slate Keller Williams Realty

  769 Seldon Dr, Winchester, VA 22601
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  /31

  $328,500

  $31K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  608 Dunlap St, Winchester, VA 22601

  Charming 3-bedroom, 1-bath ranch-style home in a highly convenient Winchester location! This well-maintained home is in great condition and has been freshly painted, offering a clean, move-in ready feel. Featuring beautiful hardwood floors throughout and a fully fenced backyard—perfect for pets, entertaining, or relaxing evenings. Central heating and air conditioning for year-round comfort.

  Richard Butcher Coldwell Banker Premier

  608 Dunlap St, Winchester, VA 22601
• 

  

  /22

  $599,950

  $25K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,948 Sq Ft

  446 N Loudoun St, Winchester, VA 22601

  Fully renovated in 2022, this upgraded duplex near Winchester's historic Walking Mall features all new electrical, HVAC, plumbing, windows, insulation, and appliances. The downstairs is a 3-bed/1-bath unit, and the upstairs is a 2-bed/1-bath unit. Separate utilities, with landlord covering water/sewer. Gross income: $44,640 annually, including shed rental. Quality tenants and off-street parking

  Lawrence Lessin Homes By Owner, Inc.

  446 N Loudoun St, Winchester, VA 22601
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  /65

  $575,000

  $25K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 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 original hardwood floors, tall ceilings, fireplace, 4 season 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

  Danielle Spriggs Samson Properties

  1400 Valley Ave, 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
• 

  

  /11

  $1,499,000

  • Land
  • 2.45 Acres
  • $611,837 per Acre

  821,829,839, and 851 Fox Dr, Winchester, VA 22603

  Location Location Location! 2.45 Acres comprised of 4 Lots with 3 income producing dwellings. Site falls withing the Frederick County Comprehensive Plan for Commercial Uses. Located just off the Route 37 and Route 522 Interchange next to Sheetz and KFC. All Dwellings and Outbuildings are strictly as-is.

  

  Jim Shebest

  Coldwell Banker Realty

  821,829,839, and 851 Fox Dr, Winchester, VA 22603
• 

  

  /35

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  112 W Germain St, Winchester, VA 22601

  100-Year-Old Downtown Winchester Charmer – Fully Reimagined in 2025!This stunning, fully restored century-old home seamlessly blends historic charm with high-end modern upgrades in the heart of downtown Winchester. Completely taken down to the studs and rebuilt in 2025, every detail was thoughtfully executed—nothing was overlooked. Proudly recognized with the 2025 Preservation of Historic

  Amanda Magana RE/MAX Roots

  112 W Germain St, Winchester, VA 22601
• 

  

  /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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  /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
• 

  

  /17

  $199,900

  $15K PRICE DROP

  • Land
  • 15,681 Sq Ft
  • $555,278 per Acre

  506 Fairmont Ave, Winchester, VA 22601

  NEW CITY LOT! This newly configured lot in the heart of downtown Winchester has been expanded and is ready for you to build your dream home. Featuring a width of approximately 100 feet, you have plenty of space to accommodate nearly any home of your choice. As a bonus, the driveway will be on the neighboring lot, which allows even more buildable space. Additionally, you do not have to worry about

  Dan Whitacre Colony Realty

  506 Fairmont Ave, Winchester, VA 22601
• 

  

  /9

  $1,300,000

  • Land
  • 64.91 Acres
  • $20,028 per Acre

  Lot 7 Cedar Creek Grade, Winchester, VA

  Rare opportunity to own 64+ scenic acres on the desirable west side of Winchester, VA. This preservation parcel offers one building right and features a beautiful mix of open land and partial woodland, providing both usability and privacy. Formerly an apple orchard, the property is well suited for a small farm, specialty crops, or vineyard, with potential for additional uses with an approved

  

  Lori Bales

  Keller Williams Realty

  Lot 7 Cedar Creek Grade, Winchester, VA

Showing Results 41 - 80, Page 2 of 3