Winchester, VA Homes

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  /52

  $556,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,192 Sq Ft

  109 Murphy Ct, Winchester, VA 22602

  ****Project My Home Approved Listing, special financing available, call agent for details.******Charming Brick 4-Bedroom Rancher in Sought-After Sovereign Village – Winchester, VAWelcome to your new home in the desirable Sovereign Village neighborhood! This beautifully maintained detached ranch-style home is nestled on a large cul-de-sac lot, offering privacy, space, and comfort both

  Kathrin Donovan Keller Williams Realty

  109 Murphy Ct, Winchester, VA 22602
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  /58

  $3,500 per month

  • 4 Beds
  • 3 Baths
  • 3,060 Sq Ft
  • House for Rent

  209 N Washington St, Winchester, VA 22601

  Live in the heart of historic Winchester! This beautifully maintained 1853 home on Washington Street offers more than just a place to live—it’s a lifestyle. With over 3,000 square feet of finished space, this one-of-a-kind rental blends timeless character with modern updates just blocks from the Old Town Walking Mall and steps from the Apple Blossom Parade Route.Inside, you’ll find

  Chris Roszko Colony Realty

  209 N Washington St, Winchester, VA 22601
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  /42

  $180,000 Sold Aug 22, 2025

  • 775 Sq Ft
  • $232/SF
  • 97 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1971

  117 Miller Rd, Winchester, VA 22602

  Welcome to 117 Miller Rd—your chance to own a hidden gem in one of Frederick County’s most historic and picturesque settings. Nestled on a beautiful, flat, and cleared 1-acre lot, this property is just minutes from downtown Winchester and less than 4 miles down Cedar Creek Grade. Tucked beside the Opequon Historic District—home to some of the area’s earliest settlements—you’ll be surrounded by

  Kaitlyn Behr RE/MAX Roots

  117 Miller Rd, Winchester, VA 22602
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  /33

  Est $412,219 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft

  417 Circle Dr, Winchester, VA 22601

  417 Circle Dr, Winchester, VA 22601
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  /14

  $1,499,000

  • Land
  • 2 Acres
  • $749,500 per Acre

  1625 Amherst St, Winchester, VA 22601

  Introducing a fantastic development opportunity! This parcel features 2 flat acres of commercial land in a prime location. Located on a major thoroughfare into downtown Winchester and a half mile from Winchester Medical Center, this lot is ideal for your commercial venture. The lot offers excellent road frontage and good topography. Ideal for medical/dental office, office space, restaurant, or

  Dan Whitacre Colony Realty

  1625 Amherst St, Winchester, VA 22601
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  /11

  $1,850 per month

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  307 Willowbrook Ct, Winchester, VA 22602

  Well maintained 3 bedroom, 1 1/2 bath townhouse end unit conveniently located close to Rt. 7 on the East end of Winchester . Nice size kitchen and living room area with attractive wood floors with 1/2 bath located on the main floor. Tenant to pay $ 1850.00 security deposit, $250 water/sewer hookup deposit and $ 30 mailbox deposit at the signing of the lease . Washer/Dryer hook up

  Jeff Boppe Long & Foster Real Estate, Inc.

  307 Willowbrook Ct, Winchester, VA 22602
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  /38

  $260,000 Sold Aug 21, 2025

  • 1,200 Sq Ft
  • $217/SF
  • 1 Day On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1989

  128 Parkside Dr, Winchester, VA 22602

  REMODELED and MOVE-IN READY! This Bright & Sunny Townhome is Nearly New Again! NEW Windows, NEW LVP Flooring Throughout Main Level, NEW Kitchen Cabinets, Countertops, & Stainless-Steel Appliances, NEW Carpet on Stairs & All Bedrooms, and Fresh Neutral Paint Throughout Home! Spacious Living Room with Triple Window Allows for Abundant Natural Light. The NEW Kitchen is Beautiful! White Cabinets,

  Bob Caines RE/MAX Distinctive Real Estate, Inc.

  128 Parkside Dr, Winchester, VA 22602
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  /36

  Est $501,602 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,600 Sq Ft

  2816 Baldwin St, Winchester, VA 22601

  2816 Baldwin St, Winchester, VA 22601
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  /71

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft

  1576 Old Bethel Church Rd, Winchester, VA 22603

  Step back in time with this 1931 farmhouse set on 5 acres, blending historic character with thoughtful modern updates—all just minutes from Winchester. This property offers convenient access to main roads while maintaining the space and feel of country living.The home features 3 bedrooms, 2 updated baths, hardwood floors, and an oversized two-car garage with workshop space. Recent

  Natasha Roberts Realty ONE Group Old Towne

  1576 Old Bethel Church Rd, Winchester, VA 22603
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  /24

  $2,295 per month

  • 3 Beds
  • 2.5 Baths
  • Townhouse for Rent

  613 Laurelwood Dr, Winchester, VA 22602

  Brand new end-unit townhouse in Laurelwood Commons Community, located just minutes from the heart of downtown. This stylish two-story townhouse features a welcoming foyer that leads into a bright, open-concept great room, perfect for relaxing or entertaining. The gourmet kitchen is equipped with stainless steel appliances, ample cabinetry, and a spacious island that flows seamlessly into

  Dev Patel Samson Properties

  613 Laurelwood Dr, Winchester, VA 22602
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  /73

  $860,000 Sold Aug 21, 2025

  • 3,793 Sq Ft
  • $227/SF
  • 397 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2006

  1321 Vanceright Cir, Winchester, VA 22601

  Rare and unique opportunity! Be just the second owner of this modern, custom, architect designed, home unlike any other! This one-of a kind contemporary home sits on the slope of one of the highest points in Winchester. It was designed by renowned local architects, Reader and Swartz, and built in 2006 by Ritter Construction. The Handley Heights location, next to an old Winchester neighborhood,

  John Scully Colony Realty

  1321 Vanceright Cir, Winchester, VA 22601
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  /52

  Est $415,167 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,702 Sq Ft

  209 W Cedarmeade Ave, Winchester, VA 22601

  209 W Cedarmeade Ave, Winchester, VA 22601
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  /40

  $337,000

  • 2 Beds
  • 2.5 Baths
  • 1,376 Sq Ft

  101 Maloy Dr, Winchester, VA 22602

  101 Maloy Dr, Winchester, VAWelcome to 101 Maloy Drive, a well-maintained single-family home on a 0.43-acre lot in Winchester. Built in 1988, this property offers 2 bedrooms, 2.5 baths, and approximately 1,376 finished square feet with a practical layout. The main level includes a spacious living area, functional kitchen, and primary suite with a walk-in closet. A bonus room provides

  Steve Bingham Realty ONE Group Capital

  101 Maloy Dr, Winchester, VA 22602
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  /23

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • Condo for Rent

  11 Brookland Terrace, Winchester, VA 22602

  Do I need to say it? Location, location, location! This lovely 3rd-floor condo is nestled in a quiet neighborhood just minutes from downtown. A commuter's dream, located directly off I-81 and Rt. 7. Tons of extras - vaulted ceilings, walk-in closet in the master, new skylights, new HVAC, brand new stove, and hardwoods in the primary suite (will be installed prior to your move in). Whether you

  Sarah Abderrazzaq Realty ONE Group Old Towne

  11 Brookland Terrace, Winchester, VA 22602
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  /38

  $296,574 Sold Aug 20, 2025

  • 1,232 Sq Ft
  • $241/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  109 Lake Sever Dr, Winchester, VA 22603

  LOCATION! LOCATION! LOCATION! This is your chance to own your own home!! This turnkey rancher with 3 bedrooms and 2 full bathrooms sits on a quiet 1/4 acre fenced lot in Regency Heights! The first "wow" moment occurs when you pull in to see a spacious covered front porch with hanging baskets and a front porch swing ready for morning coffee and evening relaxation! Through the front door, the

  Tracey Scott Path Realty

  109 Lake Sever Dr, Winchester, VA 22603
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  /33

  Est $461,262 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,518 Sq Ft

  102 Russelcroft Rd, Winchester, VA 22601

  102 Russelcroft Rd, Winchester, VA 22601
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  /43

  $415,000 Open Sat 2PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,048 Sq Ft

  128 Pioneers Rd, Winchester, VA 22602

  Charming Colonial-Cape Cod Home in Prime Winchester Location Close To Old Town.Welcome home to comfort, style, and convenience all wrapped into one! This beautifully upgraded 4-bedroom, 2-bathroom colonial-cape cod residence is ideally situated just minutes from major commuter routes and the heart of downtown Winchester, offering the perfect blend of small-town charm and peaceful serenity

  Kevin Richards Keller Williams Realty

  128 Pioneers Rd, Winchester, VA 22602
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  /50

  $2,700 per month

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • House for Rent

  709 Dicks Hollow Rd, Winchester, VA 22603

  Welcome to this private gem nestled on a corner lot in beautiful Winchester, VA! This stunning 3-bedroom, 2-bath home offers the perfect balance of modern upgrades, comfort, and peace of mind.Step inside to find a fully remodeled primary bathroom featuring a luxurious walk-in shower — a spa-like retreat in the comfort of your own home. The entire house benefits from a state-of-the-art

  Fehiber Rosario NBI Realty, LLC

  709 Dicks Hollow Rd, Winchester, VA 22603
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  /29

  $200,000 Sold Aug 20, 2025

  • 1,142 Sq Ft
  • $175/SF
  • 4 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1952

  2531 Hockman Ave, Winchester, VA 22601

  Charming Cape Cod with Tons of Potential – Ideal for Handyman or Contractor! This is an excellent opportunity to restore this classic Cape Cod home to its former glory. Perfect for a seasoned handyman, contractor, or savvy investor, this property offers incredible potential as a residential rental or flip project.Step inside to find original hardwood floors throughout, just waiting to be

  Nadeem Helfer Corcoran McEnearney

  2531 Hockman Ave, Winchester, VA 22601
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  /27

  Est $327,383 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2939 S Pleasant Valley Rd, Winchester, VA 22601

  2939 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /33

  $329,000

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

  147 Falcon Trail, Winchester, VA 22602

  Welcome to this charming home offering 3 bedrooms, 2 full bathrooms, and over 1,300 sq. ft. of finished living space (sqft is estimated). Step inside to find a warm and inviting layout with hardwood floors and new carpet throughout. The bright living area features a cozy propane fireplace, perfect for relaxing evenings. The kitchen offers easy access to the spacious back deck with brand-new

  Anthony Constable RE/MAX Gateway

  147 Falcon Trail, Winchester, VA 22602
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  /20

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,337 Sq Ft
  • House for Rent

  202 Doe Trail, Winchester, VA 22602

  Welcome home to 202 Doe Trail! This lovely ranch is on lease with more than 0.30 acres of space and comfort, simply awaiting for your gardening skills! Walk into the lovely, very well maintained home, with a freshly painted kitchen, open floor plan and three well sized bedrooms. The sellers added a slider door and beautiful deck to the home in 2022 and it's simply begging for a BBQ, company and a

  Yuri Freddy Gomez Flores Oasys Realty

  202 Doe Trail, Winchester, VA 22602
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  /10

  $110,000 Sold Aug 20, 2025

  • Land
  • 0.65 Acre
  • $169,231 per Acre

  • 15 Days On Market

  0 Oak Ridge Ln Unit VAFV2035504, Winchester, VA 22602

  Scenic .65-Acre Lot with Winchester Country Club Views – No HOAPerched above the Winchester Country Club, this .65-acre lot offers a rare chance to build in an established neighborhood with no HOA. Enjoy sweeping views, mature trees, and a peaceful setting just minutes from town. The land is raw and will require clearing and utility installation, but with electric, city water & sewer at the

  Sarah Abderrazzaq Realty ONE Group Old Towne

  0 Oak Ridge Ln Unit VAFV2035504, Winchester, VA 22602
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  /22

  Est $334,095 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2935 S Pleasant Valley Rd, Winchester, VA 22601

  2935 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /31

  $235,000

  • 3 Beds
  • 1 Bath
  • 925 Sq Ft

  205 Shenandoah Ave, Winchester, VA 22601

  LOCATION LOCATION LOCATION!!!!!!! INVESTORS DREAM. HOUSE NEEDS SOME WORK AND IS SOLD AS IS CONDITION.

  Ismael Carino MarketPlace REALTY

  205 Shenandoah Ave, Winchester, VA 22601
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  /33

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,173 Sq Ft
  • House for Rent

  136 1 Brookland Ct, Winchester, VA 22602

  ALL ON ONE LEVEL! COMMUTER CONVENIENT MAIN-FLOOR CONDO THAT'S MOVE-IN READY! EAST OF WINCHESTER, ABOUT AN HOUR FROM DULLES AIRPORT AND NEAR ROUTE 7, I-81 AND DOWNTOWN WINCHESTER. Great for those who are downsizing or just starting out or who just don't want to mow the grass anymore! Enjoy morning coffee on the 12x5 covered patio. Cozy up to the natural gas fireplace in the living room on chilly

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  136 1 Brookland Ct, Winchester, VA 22602
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  /74

  $440,000 Sold Aug 18, 2025

  • 1,432 Sq Ft
  • $307/SF
  • 7 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  300 Graywolf Trail, Winchester, VA 22602

  CAR ENTHUSIASTS - TAKE NOTICE! This lovely, well-cared-for home is perfectly situated on one lot and includes a 2nd lot that comes complete with a 40'x30', 3-bay garage with electricity and a concrete floor. The outdoor wood furnace sits inside a run-in shed to help with heating and hot water efficiency in the home! This 3-BR, 2.5-BA home offers a separate laundry room/mud room on the main floor.

  Pamela Foltz Realty ONE Group Old Towne

  300 Graywolf Trail, Winchester, VA 22602
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  /19

  Est $325,460 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2927 S Pleasant Valley Rd, Winchester, VA 22601

  2927 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /65

  $450,000

  • 4 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  113 Whipp Dr, Winchester, VA 22602

  This Is It! This sweet 4 bed, 2.5 bath home is ready for You! The moment you enter this charming single-family property you will feel right at home! From the full length front porch step into the open entry and join us in the living area, overlooking the front yard. Beyond that the family room expands right into your eat-in kitchen, all looking out onto your great deck and expansive backyard! The

  Cindy Greenya Keller Williams Realty

  113 Whipp Dr, Winchester, VA 22602
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  /39

  $1,600 per month

  • 2 Beds
  • 1.5 Baths
  • 920 Sq Ft
  • Townhouse for Rent

  527 Gray Ave Unit 2, Winchester, VA 22601

  Unit fully renovated, professionally cleaned and ready for immediate move in. Washer/dryer hook ups in unit, Pets allowed on a case by case basis, Trash, water, sewer and all exterior maintenance included in rent. Owner looking for 640 credit score or better.

  Joshua Jenkins Samson Properties

  527 Gray Ave Unit 2, Winchester, VA 22601
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  /12

  $100,000 Sold Aug 15, 2025

  • 882 Sq Ft
  • $113/SF
  • 12 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1961

  222 Liberty Ave, Winchester, VA 22601

  **OFFER DEADLINE OF 2PM ON 8/1**Investor, builder, or renovation enthusiast—this is the opportunity you’ve been waiting for!This 2-bedroom, 1-bath home is a true fixer-upper with serious potential. Whether you’re looking to take on a full gut renovation or tear it down and start from scratch, this property is a blank canvas ready for your vision. With 882 square feet of interior

  Chris Craddock EXP Realty, LLC

  222 Liberty Ave, Winchester, VA 22601
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  /21

  Est $330,011 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,060 Sq Ft

  2922 S Pleasant Valley Rd, Winchester, VA 22601

  2922 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /38

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,947 Sq Ft

  266 Pond View Ln, Winchester, VA 22603

  Discover peace and privacy at 266 Pond View Lane. Nestled on 5 scenic acres, this property offers the perfect retreat from the hustle and bustle— A wrap-around gravel driveway welcomes you home, providing plenty of space for parking and easy access to the attached garage! Step inside to find 3 spacious bedrooms, 1 full bathroom, formal dining & 3 spacious living areas! The kitchen offers

  Lisa Behr Coldwell Banker Premier

  266 Pond View Ln, Winchester, VA 22603
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  /31

  $1,499 per month

  • 2 Beds
  • 3 Baths
  • 1,148 Sq Ft
  • Townhouse for Rent

  1113 Franklin St, Winchester, VA 22601

  Ready to Move In now, Cute Town-home, Complete house hardwood floor with 2 huge bedroom and walking closet on upper floor with one full bathroom and one bedroom has its own 1/2 bathroom,On Main Floor large living room and eat in kitchen dining combo with one half bathroom and laundry hook up ,House is located at end of the street right side of CUL-DE-SAC and next to I-81 exit 315 Rt.7 ,

  Ram Beladia First American Real Estate

  1113 Franklin St, Winchester, VA 22601
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  /26

  $349,900 Sold Aug 15, 2025

  • 1,532 Sq Ft
  • $228/SF
  • 14 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2022

  116 Coralyrose Ct, Winchester, VA 22602

  **Open House is cancelled** Better than new and full of character! Welcome to 116 Coralyrose Ct – a thoughtfully upgraded townhome built in 2022 by a local custom builder, offering quality and charm that truly stand out from today’s cookie-cutter new construction. Nestled in an 15-home community just off Senseny Road, this East-side Winchester gem offers the perfect blend of convenience,

  Kaitlyn Behr RE/MAX Roots

  116 Coralyrose Ct, Winchester, VA 22602
• 

  

  /23

  Est $354,407 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  2919 S Pleasant Valley Rd, Winchester, VA 22601

  2919 S Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /14

  $469,700

  • 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, and carport with bolts in ceiling for your swing to overlook the large back yard. Then inside, new heat pump and central a/c system, new appliances with fingerprint resistant stainless-steel exterior, stainless steel liner inside the dishwasher, large cu ft counter depth

  Leo Smith CENTURY 21 New Millennium

  421 Superior Ave, Winchester, VA 22601
• 

  

  /18

  $2,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,780 Sq Ft
  • House for Rent

  433 Highland Ave, Winchester, VA 22601

  Totally updated and refreshed! Adorable 3 bedroom, 1 and a half bath single family home, ready for occupancy 6/1/25. Large home with spacious addition in the back, which could be used as a fourth bedroom. Big kitchen with loads of cabinet and counter space, two living areas, huge dining room, and a cute half bath on the main level. Tenants pay all utilities. Pets considered on a case-by-case

  Amanda White Nova Home Hunters Realty

  433 Highland Ave, Winchester, VA 22601
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  /36

  $284,900 Sold Aug 15, 2025

  • 813 Sq Ft
  • $350/SF
  • 28 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1956

  516 Hollingsworth Dr, Winchester, VA 22601

  Location & Lifestyle Highlights for 516 Hollingsworth Drive, Winchester, VANestled in one of Winchester’s most sought-after neighborhoods, 516 Hollingsworth Drive offers more than just a beautiful home; it offers a lifestyle. Enjoy direct access to scenic walking and biking trails, including the popular Green Circle Trail, which winds through town and links several parks and historic

  Chris Zarou Pearson Smith Realty, LLC

  516 Hollingsworth Dr, Winchester, VA 22601
• 

  

  /19

  Est $341,844 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  2951 S Pleasant Valley Rd, Winchester, VA 22601

  2951 S Pleasant Valley Rd, Winchester, VA 22601

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