Homes for Sale in 22601

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  /38

  $319,000 Open House 5/09

  • 2 Beds
  • 2 Baths
  • 1,382 Sq Ft

  31 E Germain St, Winchester, VA 22601

  IMPROVED PRICING! Nestled in the heart of Winchester City’s Historic District and walkable to shops and restaurants, this charming 2-bedroom, 2-bathroom gem is a rare find! The large front porch has great curb appeal and is the perfect place for outdoor lounging. The home is filled with natural light that illuminates the clean white walls and warm hardwood flooring. The living room flows into the

  Sue-Anne DeBergh Compass

  31 E Germain St, Winchester, VA 22601
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• 

  

  

  /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
• 

  

  

  /23

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  514 Cather Ave, Winchester, VA 22601

  Welcome to this beautifully maintained home where classic charm meets modern versatility! Built in 1948, this property offers warmth, character, and flexible living spaces designed to fit today’s lifestyle. Step inside to a spacious main level featuring a bright and inviting family room, a dedicated dining area, and an eat-in kitchen—perfect for everyday living and entertaining. This home offers

  

  Paula Keiper

  EXP Realty, LLC

  (540) 452-9510

  514 Cather Ave, Winchester, VA 22601
• 

  

  

  /30

  $360,000

  • 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
• 

  

  /2

  $400,000 Coming Soon

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

  605 Dunlap St, Winchester, VA 22601

  Perfectly home on a quiet lot embraced by mature, stately trees, this 5-bedroom, 2 full-bathroom home offers both seclusion and incredible proximity to Winchester's finest amenities, schools, shopping, and major commuter routes. This residence has been completely reimagined, blending the enduring strength, high-end modern finishes. The moment you enter, you are greeted by the seamless flow of

  Alexandra Brown Spring Hill Real Estate, LLC.

  605 Dunlap St, Winchester, VA 22601
• 

  

  /45

  $382,500 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  540 Eagle Place, Winchester, VA 22601

  Great opportunity for a rental investment! This well-maintained one-level rancher is tucked away in a quiet cul-de-sac, offering both convenience and long-term potential. With its prime location within walking distance to the university and easy access to Route 81, downtown, and the Apple Blossom Mall, this property is ideal for investors or owner-occupants alike. Inside, you’ll find easy,

  Camryn Jeremiah NextHome Realty Select

  540 Eagle Place, Winchester, VA 22601
• 

  

  /55

  $545,000

  • 3 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  308 Ridge Ave, Winchester, VA 22601

  Charming all-brick ranch offering comfortable one-level living in a highly convenient location! This well-maintained home features 3 bedrooms and 2 baths on the main level, along with a spacious living room highlighted by a cozy fireplace. A formal dining room provides the perfect space for entertaining, while the kitchen offers ample workspace and connects conveniently to the main-level laundry

  John Scully Colony Realty

  308 Ridge Ave, Winchester, VA 22601
• 

  

  /6

  $220,000

  • 2 Beds
  • 1.5 Baths
  • 1,064 Sq Ft

  523 Monticello St, Winchester, VA 22601

  Nice duplex. Needs a little updating. Hardwood floors in living room and throughout the 2nd level. Property at this price doesn't include the lot that is being used as part of the yard now. Property can be bought with the lot for $240k Tax id number 330-02-19.Agent related to seller.

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  (540) 660-7920

  523 Monticello St, Winchester, VA 22601
• 

  

  /21

  $379,990 New Construction

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

  117 Boone Ct, Winchester, VA 22602

  Immediate Move-in at Rossum Crossing! Winchester's newest and most popular 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

  Holly Horne Poole New Home Star Virginia, LLC

  117 Boone Ct, Winchester, VA 22602
• 

  

  /46

  $435,000

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  25 W Southwerk St, Winchester, VA 22601

  Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers the perfect balance of neighborhood tranquility and

  Dan Whitacre Colony Realty

  25 W Southwerk St, Winchester, VA 22601
• 

  

  /32

  $399,000

  • 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
• 

  

  /65

  $389,990

  • 4 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  317 Gray Ave, Winchester, VA 22601

  Welcome to 317 Gray Ave in Winchester, Virginia. This charming Colonial blends historic character with extensive modern updates, creating the perfect balance of vintage appeal and contemporary comfort. The home features 4 bedrooms, 2 full bathrooms, and 1 half bathroom, along with a recently finished attic that offers flexible additional living space. The primary suite includes a beautifully

  

  Matthew Abregu

  Keller Williams Realty

  (540) 701-3590

  317 Gray Ave, Winchester, VA 22601
• 

  

  /25

  $240,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  303 Fox Dr, Winchester, VA 22601

  MOTIVATED SELLER - bring us your offers! Welcome to this beautifully renovated 2-bedroom, 1-bath ranch-style home nestled in the peaceful, private community of Wild Acres. Surrounded by trees, this cozy 960 sq ft retreat offers the perfect blend of modern updates and natural charm. Inside, you’ll find a bright, refreshed interior with thoughtful updates throughout. Major improvements—including a

  Brandy Clem Johnston and Rhodes Real Estate

  303 Fox Dr, Winchester, VA 22601
• 

  

  /43

  $399,900

  • 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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  /36

  $309,900

  • 3 Beds
  • 1 Bath
  • 1,086 Sq Ft

  126 S Euclid Ave, Winchester, VA 22601

  This 3-bedroom, 1 full bath home is ready for you to move right in! Entire inside has been freshly painted. As you enter, you'll see the spacious living room with LVP flooring. Kitchen with new LVP flooring, new stainless-steel stove, new stainless-steel hood vent, new stainless-steel refrigerator and an eating area. Beautiful full bath with tile shower. 3 great sized bedrooms with LVP flooring.

  Matt Kilmer Samson Properties

  126 S Euclid Ave, Winchester, VA 22601
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  /61

  $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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  /97

  $1,200,000

  • 6 Beds
  • 5 Baths
  • 6,682 Sq Ft

  217 W Boscawen St, Winchester, VA 22601

  Historic Water Street Inn a magnificent legacy residence, profitable Bed & Breakfast, or sophisticated professional office opportunity! Located in Winchester's Historic District, two blocks from Old Town Walking Mall! Six large bedrooms and five full baths, this historically significant property is one of a kind, offering private garden spaces, romantic terraces, sunlight filled porches, and

  Gillian Greenfield Coldwell Banker Premier

  217 W Boscawen St, Winchester, VA 22601
• 

  

  /22

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,204 Sq Ft

  625 Watson Ave, Winchester, VA 22601

  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, and vinyl plank flooring. The bathroom includes a new vanity, vanity

  Jennifer Sacco RE/MAX Roots

  625 Watson Ave, Winchester, VA 22601
• 

  

  /56

  $424,000

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  743 Berryville Ave, Winchester, VA 22601

  Welcome to 743 Berryville Ave in the heart of Downtown Winchester! This unique and versatile property offers exceptional space and flexibility with two fully equipped living areas on one lot.The main house features 4 bedrooms, 2 full bathrooms, 2 kitchens, and 2 laundry areas—ideal for multi-generational living or added convenience. Enjoy a spacious layout with plenty of room for everyone to

  Sineenat Sirimas Pearson Smith Realty, LLC

  743 Berryville Ave, Winchester, VA 22601
• 

  

  /28

  $409,000

  • 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
• 

  

  /46

  $550,000

  • 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
• 

  

  /17

  $215,000

  • Land
  • 15,681 Sq Ft
  • $597,222 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
• 

  

  /60

  $642,900

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

  153 Harvest Ridge Dr, Winchester, VA 22601

  Welcome to 153 Harvest Ridge Drive, a beautifully appointed home tucked within the highly desirable Village at Harvest Ridge, a premier 55+ community offering comfort, quality, and ease of living. Designed for effortless main-level living, this home features a well-thought-out open floorplan that connects the living, dining, and kitchen spaces, creating a warm and inviting atmosphere with

  Jonathan Minerick Homecoin.com

  153 Harvest Ridge Dr, Winchester, VA 22601
• 

  

  /29

  $389,990 New Construction

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

  221 Monteith Dr, Winchester, VA 22601

  END OF ROW Luxury 3 level/3-bedroom townhome with 1 car garage located in the heart of Winchester! MOVE-IN READY! Explore Winchester’s new luxury townhome community. This three level end unit home features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended

  DRB Homes Builder

  221 Monteith Dr, Winchester, VA 22601
• 

  

  /27

  $274,900

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  719 Smithfield Ave, Winchester, VA 22601

  Bringing all the bungalow love! . **$8,000 closing cost credit to buyer with acceptable offer!**This 2 bed/1 bath home is move-in ready after a 2025 Refresh+. Fresh paint inside & out, new windows, new kitchen--the works: appliances, countertops, cabinets, sink, faucet; new bathroom, new LVP floors throughout, new light fixtures, baseboards, switches and outlets, new electric service line & fresh

  

  Anna Fox

  NextHome Realty Select

  (540) 590-5180

  719 Smithfield Ave, Winchester, VA 22601
• 

  

  /22

  $949,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,546 Sq Ft

  0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602

  TO BE BUILT: Fauver and Browning Homes proudly presents The Tremont House—a masterfully designed modern residence that blurs the line between architecture and nature. Thoughtfully crafted to harmonize with its surroundings, this home offers a calm, refined living experience. Tucked at the end of a private cul-de-sac in desirable Fairway Estates, overlooking Winchester Country Club, the design

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 698-4119

  0 Oak Ridge Ln Unit VAFV2039728, Winchester, VA 22602
• 

  

  /10

  $273,000

  • 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
• 

  

  /55

  $469,900

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

  620 Crystal Ct, Winchester, VA 22601

  Back and better than EVER! New Sales Price!! Rare Cul-de-Sac Gem in the Heart of Winchester! Now priced nearly $20,000 under appraisal value!! Discover the perfect blend of tranquility and city convenience at 620 Crystal Court. Situated in a sought-after, quiet cul-de-sac right in the center of Winchester, this stunning 4-bedroom, 2.5-bathroom residence has been thoughtfully updated and is ready

  VAIBHAV AGARWAL Realty FC, LLC

  620 Crystal Ct, Winchester, VA 22601
• 

  

  /47

  $265,000

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

  106 W Southwerk St, Winchester, VA 22601

  This charming 3-bedroom, 1.5-bath Colonial is perfectly located just minutes from Old Town Winchester and steps from Handley High School, giving you easy access to local restaurants, shops, and community events. Enjoy slow mornings on the covered front porch with your coffee, or gather with friends and family on the spacious back deck. Inside, you’ll find warm, comfortable living spaces filled

  Laura White ERA Oakcrest Realty, Inc.

  106 W Southwerk St, Winchester, VA 22601
• 

  

  /7

  $1,100,000

  • Land
  • 2.3 Acres
  • $478,261 per Acre

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601

  2.3 Acre Outparcel on Pleasant Valley Road for Sale Neighbors include Walmart, Ross, Target, Panera Bread, Olive Garden, Petco, and the list goes on! Zoned CM1, ideal for auto sales, offices, retail, and flex development. All utilities to site. Outstanding proximity to massive commercial and multifamily growth. VA's fastest growing City in it's fastest growing commercial district. Almost 500'

  Gillian Greenfield Coldwell Banker Premier

  0 S Pleasant Valley Rd Unit VAFV2039602, Winchester, VA 22601
• 

  

  /69

  $605,000

  • Studio
  • 4,396 Sq Ft

  540 Monticello St, Winchester, VA 22601

  Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location!Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers

  Laura King MarketPlace REALTY

  540 Monticello St, Winchester, VA 22601
• 

  

  /21

  $379,990 New Construction

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

  218 Monteith Dr, Winchester, VA 22601

  End of Row Townhome With All Three Finished Levels! This three level end of row townhome features three bedrooms, three and a half baths, and bright box bay window in the rear. An attached one car garage provides easy parking and storage. Inside, the kitchen stands out with an extended island that seats four at counter height. The first level includes a private finished recreation room and

  DRB Homes Builder

  218 Monteith Dr, Winchester, VA 22601
• 

  

  /59

  $889,000

  • 5 Beds
  • 4.5 Baths
  • 4,957 Sq Ft

  1540 Meadow Branch Ave, Winchester, VA 22601

  An exceptional offering of luxury living in the City of Winchester, this stately brick residence presents 4,958 square feet or refined, custom-designed living space. The home features 5 generously sized bedrooms and 4.5 beautifully appointed bathrooms, thoughtfully crafted for both elegant entertaining and everyday comfort. Rich architectural details and custom finishes are showcased throughout,

  John Schroth Colony Realty

  1540 Meadow Branch Ave, Winchester, VA 22601
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  /62

  $884,000 Open Sun 1PM - 3PM

  • 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
• 

  

  /73

  $650,000

  • 4 Beds
  • 3.5 Baths
  • 3,474 Sq Ft

  132 Amherst St, Winchester, VA 22601

  Charming Victorian home in the heart of Winchester’s historic downtown, move-in ready and ideally located just off the Shenandoah Apple Blossom Festival parade route. Rich in character, the foyer, front staircase, living, dining, family room, and main-level bedroom showcase beautiful wood flooring reminiscent of a bygone era. The inviting living room features a bay window and decorative

  Darcy Amburn Colony Realty

  132 Amherst St, Winchester, VA 22601
• 

  

  /12

  $80,000

  • Land
  • 5,662 Sq Ft
  • $615,385 per Acre

  520 Highland Ave, Winchester, VA 22601

  Empty lot ready to build a home one. The lot is fully fenced with front and rear gates. The front of the lot meets the sidewalks and road of Highland Ave. The rear of the lot meets a gravel alley way that could give access to off street parking on this lot. Homes in the city are in demand, so don't miss this opportunity. Zoned HR-1Can only be used for single family dwellingsFront setback:

  Michael Sprague Samson Properties

  520 Highland Ave, Winchester, VA 22601
• 

  

  /11

  $80,000

  • Land
  • 3,484 Sq Ft
  • $1,000,000 per Acre

  24 N Pleasant Valley Rd, Winchester, VA 22601

  Ready for building! Clear open lot that is ready for a home to be built. Winchester City is the fastest growing city in the state and homes are in high demand. Don't miss your opportunity. Property has road front access as well as a gravel alley in the rear that could be used for access to off street parking.Zoned MR - medium density residential districtCan only be used for single family

  Michael Sprague Samson Properties

  24 N Pleasant Valley Rd, Winchester, VA 22601
• 

  

  /45

  $465,000

  • 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
• 

  

  /45

  $479,900 Open Sun 1PM - 3PM

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

  703 S Loudoun St, Winchester, VA 22601

  Location? Check. Beautiful federal-style architecture? Check. A separate dwelling unit? Check. Endless possibilities? Check!!! This amazing property, located within the Historic Winchester District, presents a one-of-a-kind opportunity to own a piece of history - all just minutes from the Old Town mall. The front of the main home dates back to 1856! You will surely fall in love with the wood

  Kristin Crosby Samson Properties

  703 S Loudoun St, 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

  (540) 974-1542

  Lot 7 Cedar Creek Grade, Winchester, VA

Showing Results 41 - 80, Page 2 of 3