Winchester, VA Homes

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  $1,999,999 Under Contract

  • 5 Beds
  • 6 Baths
  • 5,590 Sq Ft

  821 Apple Pie Ridge Rd, Winchester, VA 22603

  This extraordinary 5-bedroom, 6-bathroom estate sits on 14.44 acres across two parcels—5.0 acres on the front lot and 9.44 acres with the residence—just minutes from Winchester, Virginia. Designed for both everyday living and elegant entertaining, this home combines timeless style with modern luxury. Inside, hardwood floors and soaring ceilings enhance open, light-filled spaces. The recently

  Jason Saphire HomeZu.com of Virginia

  821 Apple Pie Ridge Rd, Winchester, VA 22603
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  /47

  $555,000 Sold Dec 22, 2025

  2307 Stoneridge Rd, Winchester, VA 22601

  • 5 Beds
  • 3.5 Baths
  • 3,280 Sq Ft
  • Built 2016

  Last Sold Summary

  • $169/SF
  • 5 Days On Market

  Last Listing Agent Dave Spence RE/MAX Roots

  2307 Stoneridge Rd, Winchester, VA 22601
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  /73

  Est $456,688 Not Listed For Sale

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

  212 W Cedarmeade Ave, Winchester, VA 22601

  212 W Cedarmeade Ave, Winchester, VA 22601
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  /83

  $650,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,552 Sq Ft

  2708 Cassidy Ct, Winchester, VA 22601

  Rolling Hills Estates located in the Winchester City area, this beautifully maintained 5-bedroom, 3.5-bath home offers 3,552 sq ft of finished living space on a .35-acre cul-de-sac lot. Featuring a 3-car garage w/220 Car Charger, fully fenced backyard, covered front porch, and a rear Trex deck with lighting and stairs to the yard, this home is built for comfortable living and entertaining.

  Geri Deane Hunt Country Sotheby's International Realty

  2708 Cassidy Ct, Winchester, VA 22601
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  /18

  $454,990 Sold Aug 13, 2025

  106 Manasquan Way, Winchester, VA 22602

  • 3 Beds
  • 2.5 Baths
  • 1,665 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $273/SF
  • 13 Days On Market

  D.R. Horton Retreat at Winding Creek - Single Family

  106 Manasquan Way, Winchester, VA 22602
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  /41

  Est $333,674 Not Listed For Sale

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

  309 Wentworth Dr, Winchester, VA 22601

  309 Wentworth Dr, Winchester, VA 22601
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  /27

  $364,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  DELMAR Plan at Retreat at Winding Creek - Townhomes, Winchester, VA 22602

  The Delmar by D.R. Horton is a stunning new construction 2 story townhome plan featuring 1,500 square feet of living space including 3 bedrooms, 2.5 baths and a 1-car garage. The convenience of townhome living meets the amenities of a single-family home with the Delmar. The main level eat-in kitchen with large pantry and modern island opens up to an airy, bright dining and living room. The upper

  D.R. Horton Builder

  137 Seminole Dr Unit 36203785, Winchester, VA 22602
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  /36

  $390,000 Sold Aug 22, 2025

  103 Sequoia Dr, Winchester, VA 22602

  • 3 Beds
  • 3.5 Baths
  • 2,238 Sq Ft
  • Built 2016

  Last Sold Summary

  • $174/SF
  • 3 Days On Market

  Current Estimated Value $395,329

  Last Listing Agent Barton Chasler Realty ONE Group Old Towne

  103 Sequoia Dr, Winchester, VA 22602
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  /33

  Est $377,352 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,211 Sq Ft

  430 Wentworth Dr, Winchester, VA 22601

  430 Wentworth Dr, Winchester, VA 22601
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  /2

  $500,000

  • Studio
  • 1,175 Sq Ft

  513 and 525 Monticello St, Winchester, VA 22601

  For Sale – 1.89 + Acres Redevelopment Site located just off Valley Avenue in southern Winchester. Property consists of 2 parcels and includes a single family detached rental and one unimproved lot. Lot is zoned MR and Improved parcel is zoned B-2. Property is ideally suited for multi-family development. All properties are leased. Call listing broker for additional information. Do not disturb

  Brett Haynes Oakcrest Commercial LLC.

  513 and 525 Monticello St, Winchester, VA 22601
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  /36

  $370,000 Sold May 13, 2025

  520 N Loudoun St, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 1,459 Sq Ft
  • Built 1930

  Last Sold Summary

  • $254/SF
  • 32 Days On Market

  Current Estimated Value $374,648

  Last Listing Agent Dan Whitacre Colony Realty

  520 N Loudoun St, Winchester, VA 22601
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  /27

  Est $346,033 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,328 Sq Ft

  433 Beechcroft Rd, Winchester, VA 22601

  433 Beechcroft Rd, Winchester, VA 22601
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  /37

  $252,900 Under Contract

  • 3 Beds
  • 2 Baths
  • 931 Sq Ft

  309 Raccoon Dr, Winchester, VA 22602

  Move in ready 3 bedroom 2 full baths home nestled in the woods that comes with additional lots(2) that can be built on or kept as a privacy buffer and equates to an acre or so. House features hardwood flooring and lots of knotty pine for that rustic look. Living room features a wood burning fireplace that is capable of heating the entire house and there is plenty of free down wood on the lot

  James Amick RE/MAX Roots

  309 Raccoon Dr, Winchester, VA 22602
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  /9

  $95,000 Sold Aug 22, 2025

  1114 Cedar Grove Rd, Winchester, VA 22603

  • 1 Bed
  • 1 Bath
  • Built 1957

  Last Sold Summary

  • 84 Days On Market

  Current Estimated Value $91,500

  Last Listing Agent Dave Spence RE/MAX Roots

  1114 Cedar Grove Rd, Winchester, VA 22603
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  /22

  Est $356,963 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,427 Sq Ft

  314 Beechcroft Rd, Winchester, VA 22601

  314 Beechcroft Rd, Winchester, VA 22601
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  /17

  $169,900

  • Land
  • 49.61 Acres
  • $3,425 per Acre

  0 Rockwood Trail Unit 49.61 ACRES, Winchester, VA 22602

  A great many buyers are looking for decent acreage, views, the ability to hunt and shoot, the opportunity to get away on the weekends with privacy and with potential for a family retreat and maybe even future retirement. This listing clicks all the boxes. This one is on top the mountain with hard surfaced roads all the way to the top. The name of the subdivision is Great Mountain Wilderness.

  Edward Beightol Cedar Creek Real Estate

  0 Rockwood Trail Unit 49.61 ACRES, Winchester, VA 22602
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  /2

  $346,900 Sold Oct 14, 2025

  111 Comanche Trail, Winchester, VA 22602

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft
  • Built 1992

  Last Sold Summary

  • $244/SF
  • 2 Days On Market

  Current Estimated Value $344,640

  Last Listing Agent George Glaize George W. Glaize, Jr., Inc. REALTOR

  111 Comanche Trail, Winchester, VA 22602
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  /34

  Est $385,921 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,847 Sq Ft

  523 Applecroft Rd, Winchester, VA 22601

  523 Applecroft Rd, Winchester, VA 22601
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  /10

  $370,000

  • 4 Beds
  • 3 Baths
  • 1,868 Sq Ft

  126 N Euclid Ave, Winchester, VA 22601

  Discover this charming brick home that offers a perfect blend of classic character and modern convenience. This detached home features 4 spacious bedrooms and 3 full bathrooms, providing ample space for relaxation and privacy. The inviting living area boasts a cozy fireplace, ideal for creating warm memories during chilly evenings and on this level, you'll also have 2 bedrooms and a full bath.

  Marta Bingham Real Broker, LLC

  126 N Euclid Ave, Winchester, VA 22601
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  /60

  $825,000 Sold Mar 19, 2025

  105 Sundial Ct, Winchester, VA 22602

  • 5 Beds
  • 4.5 Baths
  • 4,464 Sq Ft
  • Built 2022

  Last Sold Summary

  • $185/SF
  • 71 Days On Market

  Current Estimated Value $839,211

  Last Listing Agent Dana Jensen Realty Connect

  105 Sundial Ct, Winchester, VA 22602
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  /54

  Est $545,693 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,495 Sq Ft

  604 Kernstown Ct, Winchester, VA 22601

  604 Kernstown Ct, Winchester, VA 22601
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  /16

  $279,900

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

  2901 Sorrell Ct, Winchester, VA 22601

  *Investor Opportunity, current tenants have a lease until May of 2027* Welcome to your new home! This beautifully maintained 3 -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

  Amber Jenkins Century 21 Redwood Realty

  2901 Sorrell Ct, Winchester, VA 22601
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  /50

  $465,000 Sold Jul 10, 2025

  350 Lanny Dr, Winchester, VA 22601

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft
  • Built 1967

  Last Sold Summary

  • $196/SF
  • 22 Days On Market

  Current Estimated Value $472,568

  Last Listing Agent Sheila Pack RE/MAX Roots

  350 Lanny Dr, Winchester, VA 22601
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  /90

  Est $540,623 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,632 Sq Ft

  627 Pritchards Hill Ct, Winchester, VA 22601

  627 Pritchards Hill Ct, Winchester, VA 22601
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  /16

  $450,000

  • Land
  • 77 Acres
  • $5,844 per Acre

  92 Bobcat Trail, Winchester, VA 22602

  Calling all hunters or just someone who wants seclusion! This property has amazing views and already has a structure perfect to finish your way! Perfect for getting away from it all or long hunting trips. No septic or power to structure yet. Gate to enter property. Property has 2 pink flags at the beginning of property and runs all the way to the power lines.

  Daryl Stout RE/MAX Real Estate Connections

  92 Bobcat Trail, Winchester, VA 22602
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  /55

  $419,990 Sold Jun 20, 2025

  165 Munsee Cir, Winchester, VA 22602

  • 4 Beds
  • 3.5 Baths
  • 1,889 Sq Ft
  • Built 2025

  Last Sold Summary

  • $222/SF
  • 48 Days On Market

  Last Listing Agent Tracy Jennings D R Horton Realty of Virginia LLC

  165 Munsee Cir, Winchester, VA 22602
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  /49

  Est $554,572 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,424 Sq Ft

  2833 Saratoga Dr, Winchester, VA 22601

  2833 Saratoga Dr, Winchester, VA 22601
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  /6

  $40,000

  • Land
  • 1.38 Acres
  • $28,986 per Acre

  105 Arum Trail, Winchester, VA 22602

  Welcome to your buildable, oversized 1.38 acre lot in Duck Run. Ready for your forever home? Come check this property out! No utilities on property. Blank slate ready for all your design ideas.

  Cat Haines Cedar Creek Real Estate

  105 Arum Trail, Winchester, VA 22602
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  /21

  $519,000 Sold Dec 09, 2025

  160 Country Squire Ln, Winchester, VA 22603

  • 3 Beds
  • 3 Baths
  • 1,624 Sq Ft
  • Built 1998

  Last Sold Summary

  • $320/SF
  • 1 Day On Market

  Last Listing Agent Natalie Dalecky ERA Oakcrest Realty, Inc.

  160 Country Squire Ln, Winchester, VA 22603
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  /55

  Est $551,160 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,742 Sq Ft

  2821 Saratoga Dr, Winchester, VA 22601

  2821 Saratoga Dr, Winchester, VA 22601
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  /58

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,585 Sq Ft

  139 Bryarly Rd, Winchester, VA 22603

  Step into timeless charm with this beautiful 3-bedroom, 2–full-bath home, featuring stunning original woodwork that has been exceptionally well preserved. From the moment you enter, you’ll appreciate the character and craftsmanship that make this home truly special. While leaving the character of the home, it has been well cared for. New roof within five years, windows were replaced and updated

  Hailey Mooney Real Broker, LLC

  139 Bryarly Rd, Winchester, VA 22603
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  /8

  $100,000 Sold Jan 24, 2025

  Lot 1A Fishel Rd, Winchester, VA 22602

  • Land
  • 5 Acres
  • $20,000 per Acre

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent RoxAnn Grimes RE/MAX Roots

  Lot 1A Fishel Rd, Winchester, VA 22602
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  /5

  Est $440,951 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft

  605 Dulles Cir, Winchester, VA 22601

  605 Dulles Cir, Winchester, VA 22601
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  /43

  $424,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,251 Sq Ft

  713 Ross St, Winchester, VA 22601

  ALMOST COMPLETED!!!BRAND NEW 3 BEDROOM, 2.5 BATH COLONIAL! NO HOA FEES AND NO SUBDIVISION RULES!Be the first to call this beautiful new construction yours. Conveniently located just outside the City of Winchester and close to shopping, this home offers an open layout designed for entertaining. The great room leads into the spacious kitchen featuring an oversized island, granite

  Donna Anderson Samson Properties

  713 Ross St, Winchester, VA 22601
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  /14

  $460,000 Sold Aug 07, 2025

  2620 Stonegate Dr, Winchester, VA 22601

  • 5 Beds
  • 3 Baths
  • 2,974 Sq Ft
  • Built 1995

  Last Sold Summary

  • $155/SF
  • 10 Days On Market

  Current Estimated Value $471,776

  Last Listing Agent Anthony Adamovich Key Move Properties, LLC.

  2620 Stonegate Dr, Winchester, VA 22601
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  /50

  Est $467,527 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,968 Sq Ft

  2612 Stonegate Dr, Winchester, VA 22601

  2612 Stonegate Dr, Winchester, VA 22601
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  /25

  $235,000

  • 2 Beds
  • 2 Baths
  • 1,566 Sq Ft

  114 Inca Trail, Winchester, VA 22602

  This home includes two bedrooms, each with an attached bathroom, and is over 1,500 square feet. It features an open floor plan with cathedral ceilings, exposed beams, and hardwood floors. The front family room boasts winter mountain views. The rear sunroom is perfect for enjoying the backyard wildlife. Shawneeland offers a private community beach, lake, playgrounds, and trails. If the property

  Marisa Varley ERA Oakcrest Realty, Inc.

  114 Inca Trail, Winchester, VA 22602
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  /15

  $159,900 Sold Jul 29, 2025

  236 Doe Trail, Winchester, VA 22602

  • 1 Bed
  • 1 Bath
  • 861 Sq Ft
  • Built 1971

  Last Sold Summary

  • $186/SF
  • 222 Days On Market

  Current Estimated Value $178,058

  Last Listing Agent Liz McDonald Dandridge Realty Group, LLC

  236 Doe Trail, Winchester, VA 22602
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  /47

  Est $479,807 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,722 Sq Ft

  2628 Stonegate Dr, Winchester, VA 22601

  2628 Stonegate Dr, Winchester, VA 22601
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  /34

  $584,990 Pending

  • 6 Beds
  • 4 Baths
  • 3,127 Sq Ft

  121 Mascouten St, Winchester, VA 22602

  “Builder is offering special buyer incentives as part of the current Red Tag Sale period. Incentives may be available to purchasers of this home.”The Hayden is a spacious two-story home featuring 6 bedrooms and 4 bathrooms across more than 3,100 square feet. The main level includes a versatile flex room off the foyer—perfect for a formal dining area or home office. The gourmet kitchen boasts

  Brooks Sears D R Horton Realty of Virginia LLC

  121 Mascouten St, Winchester, VA 22602

Showing Results 561 - 600, Page 15 of 18