Winchester County, VA Homes

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  $354,999

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

  16 S Pleasant Valley Rd, Winchester, VA 22601

  Welcome to 16 S Pleasant Valley Rd — a beautifully updated home just minutes from the heart of Winchester!Enjoy the perfect blend of convenience and comfort, with an easy walk to the Walking Mall, historic downtown, restaurants, shops, and the Museum of the Shenandoah Valley—plus quick access to major commuter routes.Inside, you’ll find a bright, inviting layout with natural light flowing

  Vanessa Couture Samson Properties

  16 S Pleasant Valley Rd, Winchester, VA 22601
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  $1,400 Per Month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Townhouse for Rent

  2 E Germain St, Winchester, VA 22601

  Location! Walking distance from downtown walking mall and public transportation. 2 bedroom 1 bath apartment with hardwood flooring throughout living room and bedrooms. Property features a front porch, wash/dryer hookup and off street parking. Yard maintenance is included in rent. Requirements to qualify: 1) Minium annual household income $63K, 2) Good credit, and 3) Good landlord reference. $47

  Courtney Spaid Crum Realty, Inc.

  2 E Germain St, Winchester, VA 22601
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  /52

  $347,500 Sold Apr 09, 2026

  217 Myrtle Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 907 Sq Ft
  • Built 1961

  Last Sold Summary

  • 7% Below List Price
  • $383/SF
  • 50 Days On Market

  Current Estimated Value $347,371

  Last Listing Agent Pamela Foltz Realty ONE Group Old Towne

  217 Myrtle Ave, Winchester, VA 22601
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  Est $267,655 Not Listed For Sale

  2945 Sorrell Ct, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,332 Sq Ft
  • Built 2000

  2945 Sorrell Ct, Winchester, VA 22601

  Last Sold Summary

  • 5% Above List Price
  • $191/SF
  • 4 Days On Market

  • Last Sold Price $255,000
  • May 24, 2024

  Last Listing Agent Carolyn Waymack Crum Realty, Inc.
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  $299,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,204 Sq Ft

  625 Watson Ave, Winchester, VA 22601

  * Now offering added value with $7500 seller concessions available.* Nestled in Orchard Terrace, this beautifully updated Colonial home is ideally located within Winchester city limits, just a short walk to the vibrant downtown walking mall with its shops, dining, and entertainment. The updated kitchen features new cabinets, granite countertops, stainless steel appliances, a new sink and faucet,

  Jennifer Sacco RE/MAX Roots

  625 Watson Ave, Winchester, VA 22601
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  /15

  $1,650 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,438 Sq Ft
  • Townhouse for Rent

  313 N Kent St, Winchester, VA 22601

  Welcome to this charming home ideally located within walking distance of Winchester’s Historic Downtown Walking Mall, where you’ll enjoy easy access to restaurants, shopping, and local parks. You’re also just a short drive to Winchester Medical Center and Shenandoah University. Inside, the home offers a functional and inviting layout with a spacious living room, dining area, and a kitchen

  James King RE/MAX Roots

  313 N Kent St, Winchester, VA 22601
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  /40

  $632,500 Sold Apr 24, 2026

  162 Omps Dr, Winchester, VA 22601

  • 6 Beds
  • 3.5 Baths
  • 3,192 Sq Ft
  • Built 1990

  Last Sold Summary

  • 1% Below List Price
  • $198/SF
  • 13 Days On Market

  Current Estimated Value $631,004

  Last Listing Agent Kimberly Schroeder Long & Foster Real Estate, Inc.

  162 Omps Dr, Winchester, VA 22601
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  /18

  Est $286,767 Not Listed For Sale

  2947 Sorrell Ct, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,332 Sq Ft
  • Built 2001

  2947 Sorrell Ct, Winchester, VA 22601

  Last Sold Summary

  • 6% Above List Price
  • $203/SF
  • 4 Days On Market

  • Last Sold Price $270,000
  • Jun 03, 2024

  Last Listing Agent Laura White ERA Oakcrest Realty, Inc.
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  $445,000 Open House 5/17

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

  2250 Roosevelt Blvd, Winchester, VA 22601

  Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main

  Heloisa Amar Samson Properties

  2250 Roosevelt Blvd, Winchester, VA 22601
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  $1,050 Per Month

  • 1 Bed
  • 1 Bath
  • 10,710 Sq Ft
  • House for Rent

  2264 Papermill Rd Unit C, Winchester, VA 22601

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  2264 Papermill Rd Unit C, Winchester, VA 22601
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  $284,900 Sold Aug 15, 2025

  516 Hollingsworth Dr, Winchester, VA 22601

  • 2 Beds
  • 1 Bath
  • 813 Sq Ft
  • Built 1956

  Last Sold Summary

  • $350/SF
  • 28 Days On Market

  Current Estimated Value $277,352

  Last Listing Agent Chris Zarou Pearson Smith Realty, LLC

  516 Hollingsworth Dr, Winchester, VA 22601
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  /30

  Est $282,353 Not Listed For Sale

  2955 Sorrell Ct, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,332 Sq Ft
  • Built 2001

  2955 Sorrell Ct, Winchester, VA 22601

  Last Sold Summary

  • 9% Above List Price
  • $195/SF
  • 5 Days On Market

  • Last Sold Price $260,000
  • Jun 30, 2023

  Last Listing Agent James Amick RE/MAX
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  $429,000 Coming Soon

  • 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 Winchester’s historic downtown walking mall, offering easy access to restaurants, bars, boutiques, and entertainment. Originally built in the 1900s, this beautifully updated home showcases exposed brick walls, timeless architectural charm, and

  Janet Flaherty Keller Williams Realty

  118 1/2 E Cork St, Winchester, VA 22601
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  /15

  $2,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft
  • Townhouse for Rent

  2066 Honeysuckle Ln, Winchester, VA 22601

  Spacious duplex in sought after ORCHARD HILL SUBDIVISION will be AVAILABLE July 1, 2026 for a new tenant to move in! 3 spacious bedrooms, ample storage space with several walk in closets, all appliances convey including washer/dryer. Sun room with cathedral ceilings and atrium doors to exit onto the rear brick patio, storage shed, small garden, and so much more! VAR or NVAR rental application

  Misty Miller OliveTree Property Group, LLC

  2066 Honeysuckle Ln, Winchester, VA 22601
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  $490,000 Sold Jun 09, 2025

  435 Mosby St, Winchester, VA 22601

  • 4 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Built 1956

  Last Sold Summary

  • $305/SF
  • 0 Days On Market

  Current Estimated Value $489,848

  Last Listing Agent Angela Duncan MarketPlace REALTY

  435 Mosby St, Winchester, VA 22601
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  /16

  Est $290,849 Not Listed For Sale

  2975 Sorrell Ct, Winchester, VA 22601

  • 2 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • Built 1990

  2975 Sorrell Ct, Winchester, VA 22601

  Last Sold Summary

  • 12% Above List Price
  • $138/SF

  • Last Sold Price $260,000
  • Aug 25, 2023

  Last Listing Agent Amanda White Nova Home Hunters Realty
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  $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—almost ready for summer 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

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  126 Swansong Place, Winchester, VA 22603
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  $1,200 Per Month

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Condo for Rent

  208 W Boscawen St Unit 12, Winchester, VA 22601

  This apartment is conveniently located to downtown Winchester. Coin Op Washer & Dryer on the main level. Rear deck access. Water & Sewer, weekly trash service and monthly pest treatment included in rent. Cat considered, no dogs. Minimum credit score of 650 and income equaled to 3X the rent required to apply. No Prior evictions.

  Marisa Varley ERA Oakcrest Realty, Inc.

  208 W Boscawen St Unit 12, Winchester, VA 22601
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  $125,000 Sold Mar 26, 2026

  222 Liberty Ave, Winchester, VA 22601

  • 3 Beds
  • 1 Bath
  • 882 Sq Ft
  • Built 1961

  Last Sold Summary

  • 17% Below List Price
  • $142/SF
  • 7 Days On Market

  Current Estimated Value $185,261

  Last Listing Agent Kandi McKenzie Realty ONE Group Old Towne

  222 Liberty Ave, Winchester, VA 22601
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  /23

  Est $289,964 Not Listed For Sale

  2950 Sorrell Ct, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 1,280 Sq Ft
  • Built 1990

  2950 Sorrell Ct, Winchester, VA 22601

  Last Sold Summary

  • $226/SF
  • 34 Days On Market

  • Last Sold Price $289,000
  • Oct 23, 2024

  Last Listing Agent Maria Jaimes Millennium Realty Group Inc.
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  $915,000

  • 4 Beds
  • 3.5 Baths
  • 4,330 Sq Ft

  512 S Loudoun St, Winchester, VA 22601

  Distinctive home on the historic register, Winchester walking tour, this property has been featured on the Winchester homes tour ---Walk two blocks into the heart of Winchester; restaurants, festivals, shopping! Gorgeous inside and out. Fully renovated, 4 levels with a two-story log cabin (the blue building) likely built with timber from Fort Loudoun) , gourmet emodeled kitchen with gas cooking,

  Roxanne Watts Coldwell Banker Realty

  512 S Loudoun St, Winchester, VA 22601
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  $1,395 Per Month

  • 2 Beds
  • 1 Bath
  • 6,578 Sq Ft
  • Townhouse for Rent

  207 E Whitlock Ave, Winchester, VA 22601

  Charming Townhome in the Heart of Downtown Winchester!This beautifully updated 3-bedroom, 1-bath townhome offers the perfect blend of historic charm and modern convenience. Featuring a fresh renovation throughout, the home boasts a stylish kitchen with new appliances, updated cabinetry, and a bright, open living space. Upstairs, you'll find two spacious bedrooms and a modern full bath.

  Amy Emerson-Kerns Cambridge Premier Realty, LLC.

  207 E Whitlock Ave, Winchester, VA 22601
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  $385,000 Sold Nov 24, 2025

  1823 Kershaw Ln, Winchester, VA 22601

  • 2 Beds
  • 2 Baths
  • 1,591 Sq Ft
  • Built 2003

  Last Sold Summary

  • $242/SF
  • 9 Days On Market

  Current Estimated Value $389,036

  Last Listing Agent Natalie Langford ERA Oakcrest Realty, Inc.

  1823 Kershaw Ln, Winchester, VA 22601
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  Est $253,882 Not Listed For Sale

  503 Yorktowne Place, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,116 Sq Ft
  • Built 1984

  503 Yorktowne Place, Winchester, VA 22601

  Last Sold Summary

  • 6% Above List Price
  • $214/SF
  • 3 Days On Market

  • Last Sold Price $239,000
  • May 16, 2023

  Last Listing Agent Jennifer Sacco RE/MAX
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  /21

  $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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  /20

  $1,600 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,316 Sq Ft
  • Townhouse for Rent

  8 W Monmouth St, Winchester, VA 22601

  Charming 2-Story Townhouse for Rent in Winchester City Welcome to this well-maintained 2-story townhouse located in the heart of Winchester! This comfortable home offers a functional layout with 1 full bath and 1 half bath, perfect for convenient everyday living. The main level features a bright living area, a spacious kitchen with ample cabinet space, and a dining area ideal for entertaining. A

  Ruby Miller Samson Properties

  8 W Monmouth St, Winchester, VA 22601
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  $357,000 Sold Aug 07, 2025

  205 Parkway St, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 1,008 Sq Ft
  • Built 1971

  Last Sold Summary

  • $354/SF
  • 86 Days On Market

  Current Estimated Value $355,843

  Last Listing Agent Agustin Martinez Spring Hill Real Estate, LLC.

  205 Parkway St, Winchester, VA 22601
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  Est $472,252 Not Listed For Sale

  2894 Packer St, Winchester, VA 22601

  • 4 Beds
  • 2.5 Baths
  • 2,460 Sq Ft
  • Built 2006

  2894 Packer St, Winchester, VA 22601

  Last Sold Summary

  • 11% Above List Price
  • $173/SF
  • 7 Days On Market

  • Last Sold Price $425,000
  • Nov 08, 2024

  Last Listing Agent Renzo Falla RE/MAX
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  /22

  $625,000

  • 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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  $1,100 Per Month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  702 S Braddock St Unit 2, Winchester, VA 22601

  Gorgeous one-bedroom apartment in Historic Winchester, VA. Convenient distance to the Old Town Winchester Walking Mall and beautiful John Handley High School. Enjoy the amenities that Winchester offers in entertainment and dining with a short walk from your front door. This apartment comes with a large kitchen with full-size appliances featuring a new microwave, spacious living room, and a

  Mr. Nate Crandell HoneyWay

  702 S Braddock St Unit 2, Winchester, VA 22601
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  /2

  $335,000 Sold Apr 13, 2026

  601 Hollingsworth Dr, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,684 Sq Ft
  • Built 1961

  Last Sold Summary

  • $199/SF
  • 12 Days On Market

  Current Estimated Value $314,614

  Last Listing Agent Craig Alexander Coldwell Banker Premier

  601 Hollingsworth Dr, Winchester, VA 22601
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  Est $439,257 Not Listed For Sale

  201 Russelcroft Rd, Winchester, VA 22601

  • 3 Beds
  • 2.5 Baths
  • 3,066 Sq Ft
  • Built 1970

  201 Russelcroft Rd, Winchester, VA 22601

  Last Sold Summary

  • 3% Above List Price
  • $139/SF
  • 10 Days On Market

  • Last Sold Price $425,000
  • Jun 25, 2024

  Last Listing Agent Dorothy Vance The KW Collective
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  $539,900

  • 4 Beds
  • 2 Baths
  • 2,837 Sq Ft

  1317 Caroline St, Winchester, VA 22601

  Welcome to 1317 Caroline Street, a well-appointed brick rancher in a fantastic Winchester location that perfectly balances professional convenience with residential comfort. Situated just minutes from Winchester Medical Center and major commuter routes, this home offers an effortless transition from a busy day to a relaxing evening. This sense of ease begins the moment you step inside the main

  Dan Whitacre Colony Realty

  1317 Caroline St, Winchester, VA 22601
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  $2,200 Per Month

  • 3 Beds
  • 1 Bath
  • 1,194 Sq Ft
  • House for Rent

  123 Bellview Ave, Winchester, VA 22601

  Available June 8, this updated 3-bedroom home in Winchester City offers a functional layout with two bedrooms on the main level and a finished loft upstairs. The kitchen features granite countertops, stainless steel appliances, and a bright morning room filled with natural light. The living room includes hardwood floors and a fireplace, and the fully fenced backyard offers a patio and pergola for

  Rachel Olsen Keller Williams Realty

  123 Bellview Ave, Winchester, VA 22601
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  /20

  $310,000 Sold Jul 10, 2025

  213 West St, Winchester, VA 22601

  • 2 Beds
  • 1.5 Baths
  • 1,281 Sq Ft
  • Built 1946

  Last Sold Summary

  • $242/SF
  • 0 Days On Market

  Current Estimated Value $303,343

  Last Listing Agent Mandy Barnes RE/MAX Gateway, LLC

  213 West St, Winchester, VA 22601
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  Est $484,174 Not Listed For Sale

  212 W Cedarmeade Ave, Winchester, VA 22601

  • 5 Beds
  • 2.5 Baths
  • 2,899 Sq Ft
  • Built 1967

  212 W Cedarmeade Ave, Winchester, VA 22601

  Last Sold Summary

  • 18% Above List Price
  • $141/SF
  • 91 Days On Market

  • Last Sold Price $410,000
  • Dec 27, 2023

  Last Listing Agent Gina Chatham Century 21 Redwood Realty
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  $320,000 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  2912 2nd St, Winchester, VA 22601

  2912 2nd Street — a cozy 3-bedroom, 1-bath ranch-style home offering comfortable single-level living in Winchester. The home opens to a light-filled living area with hardwood floors that add warmth and character, creating an inviting space to relax or gather. The eat-in kitchen provides practical workspace, with an easy flow that keeps everything connected. Both bedrooms are located on the main

  Sabrina Priest Preslee Real Estate

  2912 2nd St, Winchester, VA 22601
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  /26

  $399,990 Sold Mar 18, 2026

  234 Monteith Dr, Winchester, VA 22601

  • 3 Beds
  • 3.5 Baths
  • 1,784 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $224/SF
  • 29 Days On Market

  DRB Homes Village at Valor Crossing - Townhomes

  234 Monteith Dr, Winchester, VA 22601
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  Est $332,174 Not Listed For Sale

  309 Wentworth Dr, Winchester, VA 22601

  • 3 Beds
  • 1.5 Baths
  • 1,148 Sq Ft
  • Built 1966

  309 Wentworth Dr, Winchester, VA 22601

  Last Sold Summary

  • 15% Above List Price
  • $253/SF
  • 4 Days On Market

  • Last Sold Price $290,000
  • Aug 08, 2023

  Last Listing Agent Julie Teets ERA Oakcrest Realty, Inc.
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  $549,900

  • 3 Beds
  • 2.5 Baths
  • 3,083 Sq Ft

  3013 Saratoga Dr, Winchester, VA 22601

  Nestled in the prestigious Battle Park Estates, this exquisite residence embodies the perfect blend of luxury and comfort. Built in 2001, this detached home showcases a timeless design with high-end finishes that create an inviting atmosphere throughout. Step inside to discover a spacious open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for both entertaining

  Michelle Donovan Long & Foster Real Estate, Inc.

  3013 Saratoga Dr, Winchester, VA 22601

Showing Results 361 - 400, Page 10 of 18