Winchester, VA Homes for Sale

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  $1,050,000

  • 4 Beds
  • 4 Baths
  • 5,069 Sq Ft

  1460 Pitcock Ln, Winchester, VA 22602

  Escape to Your Private Retreat – Just 10 Minutes from Winchester!Don’t miss the 3D tour attached to this listing! Welcome to a truly one-of-a-kind property offering 27.65 secluded acres across three parcels, complete with towering trees, a tranquil pond, and breathtaking natural surroundings. This charming log home is rich with character and history—originally relocated here in the 1960s,

  Sheila Pack RE/MAX Roots

  1460 Pitcock Ln, Winchester, VA 22602
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  /35

  $459,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 1,905 Sq Ft

  Adams II Plan at Abrams Crossing at Meadow Branch, Winchester, VA 22601

  The Adams II townhome features 1,905 sq. ft. of stylish and flexible living space, including 4 bedrooms, 3.5 bathrooms, and a 1-car rear-load garage. The gourmet kitchen is equipped with quartz countertops, stainless steel appliances, recessed lighting, a generous island, and sleek Duraform cabinetry. The lower-level bonus room offers endless possibilities—use it as a rec room, home office, or an

  D.R. Horton Builder

  1831 Reese Ct Unit 37025141, Winchester, VA 22601
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  /26

  $374,990

  New Construction

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  HOMESITE 8 Monteith Dr, Winchester, VA 22601

  End of Row Townhome with 3 Bedrooms & 3.5 Bathrooms! All Three Levels Finished! 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 island that seats four at counter

  DRB Homes Builder

  HOMESITE 8 Monteith Dr, Winchester, VA 22601
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  /15

  $89,000

  • Land
  • 5.02 Acres
  • $17,729 per Acre

  0 Pack Horse Road Lot B Unit VAFV2042704, Winchester, VA 22603

  The rural America many people desire is available on state maintained Pack Horse Road. There are 3 lots being sold separately and this 5 acre lot B is wooded, has an old cabin (do not enter and at one time had electric), has a Frederick County cert letter (see documents from health department however buyer should do due diligence). Unrestricted and so think about the possibilities for a

  Dave Spence RE/MAX Roots

  0 Pack Horse Road Lot B Unit VAFV2042704, Winchester, VA 22603
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  /29

  $240,000

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

  304 Ash Hollow Dr, Winchester, VA 22602

  **BACK ON MARKET!** No fault of the property/sellers. Why rent when you can own?! This property has 1,148 square feet of finished living space plus a walk-out patio and yard that backs up to trees. The kitchen features newer cabinets, countertops, range hood, and tile backsplash. Enjoy the ease of everyday living with a highly convenient commuter location just minutes from Route 7 and I-81,

  Steph Drahozal Pearson Smith Realty, LLC

  304 Ash Hollow Dr, Winchester, VA 22602
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  /2

  $355,000

  Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  100 Oakmont Cir, Winchester, VA 22602

  **Move-in ready!** Welcome to 100 Oakmont Circle, a beautifully updated 3-bedroom, 1.5-bath home filled with natural light and an open, inviting floor plan. Enjoy an updated kitchen featuring stainless steel appliances, new countertops, and a new oven/range, along with new hardwood floors in the living and dining rooms. Step outside to a spacious, fully fenced backyard with mature trees offering

  Raven Staub Samson Properties

  100 Oakmont Cir, Winchester, VA 22602
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  /83

  $437,750

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,327 Sq Ft

  131 Country Club Cir, Winchester, VA 22602

  Welcome to 131 Country Club Circle, a beautifully appointed all-brick masonry residence offering timeless construction and exceptional living space. This impressive home showcases tall ceilings and real hardwood flooring throughout the main level, creating a warm yet refined atmosphere. The thoughtfully designed layout includes a sunroom on the main level, ideal as a home office or flex space,

  Alexi Faraco Smart Realty, LLC

  131 Country Club Cir, Winchester, VA 22602
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  /15

  $220,000

  • Land
  • 5.39 Acres
  • $40,816 per Acre

  TBD (0) Cather Ln, Winchester, VA 22602

  Searching for the ideal place to build your dream home? This awesome 5.39 acre parcel delivers stunning views and a convenient location just minutes from town. Situated right off Rt 50 with easy access to Rt 37 and Interstate 81, you’ll be close to gas stations, restaurants, shopping, the hospital, and so much more—offering the perfect blend of peaceful country living and everyday convenience.

  Brian Doman Preslee Real Estate

  TBD (0) Cather Ln, Winchester, VA 22602
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  /49

  $320,000

  • 4 Beds
  • 2 Baths
  • 2,034 Sq Ft

  410 S Cameron St, Winchester, VA 22601

  Step into a home where timeless character and modern opportunity come together. This spacious property is filled with antique charm and unique details throughout.Featuring 4 bedrooms, 2 full bathrooms, and several versatile flex spaces, this home can easily adapt to your needs or offer increased income potential with a renovation. Enjoy the outdoor living opportunities with a private

  Heloisa Amar Samson Properties

  410 S Cameron St, Winchester, VA 22601
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  /2

  $249,000

  Coming Soon

  • 2 Beds
  • 2 Baths
  • 1,257 Sq Ft

  1576 Brookland Terrace Unit 6, Winchester, VA 22602

  Coming Soon to the Market! Fantastic location! This spacious second-floor condo offers more square footage than most units in the community and features an open, light-filled layout, and durable flooring throughout with NO carpet. The thoughtfully designed floor plan includes a large living room, separate dining area, two generously sized bedrooms, and two full bathrooms. The primary suite offers

  Kim Hurst MarketPlace REALTY

  1576 Brookland Terrace Unit 6, Winchester, VA 22602
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  /7

  $775,000

  New Construction $10K PRICE INCREASE

  • 4 Beds
  • 2.5 Baths
  • 3,150 Sq Ft

  0 Tumble Leaf Ln, Winchester, VA 22602

  CARRINGTON HOMES AT FALL RIDGE ESTATES- 5 Acre Wooded LOTS WITH MOUNTAIN VIEWS. Choose from 7 different floorplans including our Chestnut model with standard 10' Main Level Ceilings Model Home Open on Weekends from 11-5 at 156 Covey Lane Winchester Va

  Daniel Boris Pearson Smith Realty, LLC

  0 Tumble Leaf Ln, Winchester, VA 22602
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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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  /24

  $359,990

  New Construction $5K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 1,756 Sq Ft

  12 Monteith Dr, Winchester, VA 22601

  Open House Saturday & Sunday 12-3pm!3 Level Townhome with 3 Bedrooms! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. This beautifully upgraded home features an open-concept layout with

  DRB Homes Builder

  12 Monteith Dr, Winchester, VA 22601
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  /28

  $420,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  775 Pack Horse Rd, Winchester, VA 22603

  Completely remodeled and move-in ready, this charming property at 775 Pack Horse Road in Frederick County, VA offers the perfect blend of modern updates and peaceful country living. Situated on a picturesque setting, the home has been thoughtfully renovated throughout, featuring updated finishes, refreshed interiors, and attention to detail in every room. Enjoy the convenience of a detached

  Amanda Slate Keller Williams Realty

  775 Pack Horse Rd, Winchester, VA 22603
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  /41

  $598,990

  New Construction

  • 3 Beds
  • 2 - 3 Baths
  • 3,213 Sq Ft

  Drexel Plan at Abrams Pointe, Winchester, VA 22602

  The Drexel home design is a spacious and versatile single-family home designed to suit a variety of lifestyles. With 3,213 finished square feet, the Drexel offers generous living space that can be customized to meet your needs. It features main-level living with three bedrooms, including a private master suite with a walk-in closet and en-suite bathroom, along with two full bathrooms and a 2-car

  Maronda Homes Builder

  161 Williamson Rd Unit 38167756, Winchester, VA 22602
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  /55

  $365,000

  • 3 Beds
  • 2 Baths
  • 2,280 Sq Ft

  617 Fox Trail, Winchester, VA 22602

  Looking for a mountain top getaway? This adorable rancher is it with 3 bedrooms, 2 full baths. Updated kitchen w/stainless appliances and tons of light. Back deck is an oasis with a gazebo and a place to sip morning coffee and overlook the incredible wooded lot. This home has an extra building lot as well (lot is to the left of the home)! Full basement with family room, rec room w/pool table and

  Traci Shoberg Samson Properties

  617 Fox Trail, Winchester, VA 22602
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  /27

  $509,990

  New Construction $17K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,168 Sq Ft

  122 Trellis View Ln, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Freeport floorplan is a thoughtfully designed villa, blending style and functionality in a single-level open layout and finished loft, complete with a 2-car garage. This stunning 1,492 sq. ft. residence features three bedrooms and two baths on the main level, with the finished loft offering an additional 676 sq ft of

  D.R. Horton Builder

  122 Trellis View Ln, Winchester, VA 22602
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  /32

  $599,990

  New Construction $7K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,865 Sq Ft

  117 Scented Rose Way, Winchester, VA 22602

  Experience effortless living in our Willow Run Active Adult community! Our Clifton floorplan is a thoughtfully designed 1,865 sq.ft. ranch home, blending style and functionality in a single-level open layout.The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The kitchen opens to a large great room with four windows that let in

  D.R. Horton Builder

  117 Scented Rose Way, Winchester, VA 22602
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  /13

  $199,000

  • Land
  • 20.05 Acres
  • $9,925 per Acre

  951 Bobcat Trail, Winchester, VA 22602

  Breathtaking Views and Endless Possibilities! Discover your own slice of paradise on this stunning 20.05-acre property! With a 3-bedroom perc already in place, drainfield and distribution box installed, and electric at the property, you're just a septic tank away from breaking ground. Part of the lot is already cleared, making it the perfect spot to build your dream home, weekend getaway, or cozy

  Sharon Farinholt Realty ONE Group Old Towne

  951 Bobcat Trail, Winchester, VA 22602
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  /2

  $12,800

  • Land
  • 17,424 Sq Ft
  • $32,000 per Acre

  0 Budwood Trail Unit 11620368, Winchester, VA 22602

  Nice level corner wooded lot. Corner of Budwood and Rockwood Follow your GPS to the corner point. All measurements are taken from government sources. Such as the actual .4. acres is actually .398 acres rounded up.

  John Holsinger JOHN S HOLSINGER REAL ESTATE BROKER LLC

  0 Budwood Trail Unit 11620368, Winchester, VA 22602
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  /59

  $1,150,000

  New Construction $50K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 5,425 Sq Ft

  Lot 1 Keval Gyan Way, Winchester, VA 22603

  Foundation dug and construction to begin soon. To have finished basement. Seize a rare opportunity to own one of just fifteen premier lots within the prestigious, upper-scale Keplinger Estates near the Apple Pie Ridge area. This is not just a house; it is a bespoke sanctuary offering a sophisticated lifestyle with the ultimate convenience of being close to town, yet free from the constraints of

  Jim Thomson Realty ONE Group Old Towne

  Lot 1 Keval Gyan Way, Winchester, VA 22603
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  /6

  $12,900

  • Land
  • 10,890 Sq Ft
  • $51,600 per Acre

  Lot 17 Fox Trail, Winchester, VA 22602

  Are you looking for an affordable approved building lot under 20 minutes to Winchester Medical Center I 81 or I 66 and an overwhelming sense of nature with unparalleled mountain views? Look no further! Mountain Falls Park is known for its close proximity to town, waterfalls, views for miles and a quiet community. This lot is very buildable it is level, has a current survey, recorded plat and a

  Nadeem Helfer Samson Properties

  Lot 17 Fox Trail, Winchester, VA 22602
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  /28

  $482,990

  New Construction $17K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,216 Sq Ft

  GLENDALE Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  The Glendale is a new construction home plan featuring 2,216 square feet of living space, 4 bedrooms, 3.5 baths and a 2-car garage. The Glendale gives you the features you’re looking for at the price you want! You’ll immediately feel at home as you enter into the spacious family room. This living space flows nicely into the eat-in kitchen which highlights a peninsula island overlooking the family

  D.R. Horton Builder

  137 Seminole Dr Unit 39403232, Winchester, VA 22602
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  /41

  $489,990

  New Construction $45K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,284 Sq Ft

  100 Brockham Ct, Winchester, VA 22602

  This move-in-ready home includes pre-selected upgrades and a new-construction warranty. Welcome to this beautifully crafted new home by a respected local builder, offering almost 2,300 square feet of thoughtfully designed living space in the desirable Sovereign Village community. The inviting, open-concept main level features a spacious kitchen with a large island, perfect for gathering and

  Marisa Varley ERA Oakcrest Realty, Inc.

  100 Brockham Ct, Winchester, VA 22602
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  /66

  $975,000

  • 4 Beds
  • 3 Baths
  • 3,202 Sq Ft

  165 Carroll Ridge Ln, Winchester, VA 22602

  Modern farmhouse living meets peaceful acreage on 2.75 acres right on Cedar Creek Grade. Built just two years ago by owner/builder Stephen Carroll, this thoughtfully designed home offers main-level living, scenic hilltop views, a walkout basement, high-speed fiber-optic internet, and a peaceful outdoor setting complete with a koi pond, wildflower meadow, and 275+ trees planted around the

  Bailey Cooper RE/MAX Gateway

  165 Carroll Ridge Ln, Winchester, VA 22602
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  /3

  $275,000

  • Land
  • 5.79 Acres
  • $47,496 per Acre

  LOT 1 - Handley Dr, Winchester, VA 22603

  Spring Valley Estates. A rare opportunity to find a 5-Acre lots within 5 minutes of downtown Winchester and the Valley Health Medical Center. James Wood High School and Apple Pie Elementary within a mile of this lot. Fully built lot with approved perc on file. Buyer can buy the lot and build their dream house or for future investment purposes. This corner lot is cleared with existing road

  JP Carr Merrifield Realty, LLC

  LOT 1 - Handley Dr, Winchester, VA 22603
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  /22

  $389,990

  New Construction $10K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,026 Sq Ft

  116 Swansong Place, Winchester, VA 22603

  Exceptional Value – Brand-New 3-Bedroom Townhome for Summer Move-In!Don’t miss this incredible opportunity to own a beautifully crafted new construction townhome in the newest section of Snowden Bridge.Designed for modern living, this home features oak stairs with upgraded railings and durable luxury vinyl plank flooring throughout the main level. The bright, stylish kitchen boasts white

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  116 Swansong Place, Winchester, VA 22603
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  /62

  $799,000

  • 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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  /40

  $540,000

  • 4 Beds
  • 2.5 Baths
  • 2,463 Sq Ft

  124 Lenore Ln, Winchester, VA 22602

  Welcome to 124 Lenore Lane, a beautifully appointed home in Winchester that blends modern upgrades, thoughtful design, and everyday comfort. This spacious residence offers a layout that works effortlessly for a wide range of lifestyles, with quality finishes throughout, all in a highly desirable community with outstanding amenities. The upper level features four generously sized bedrooms and two

  Sergio Vitela EXP Realty, LLC

  124 Lenore Ln, Winchester, VA 22602
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  /33

  $415,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  104 Lloyds Rd, Winchester, VA 22602

  This charming ranch-style home is filled with warmth and sophistication. Step inside to discover an inviting atmosphere, accentuated by exquisite interior features such as chair railings and crown moldings. The thoughtfully designed space features three spacious bedrooms and two luxurious baths, including a primary suite with a whirlpool tub and separate shower. Rich wood floors create a cozy

  Val Nicole Clark Realty FC, LLC

  104 Lloyds Rd, Winchester, VA 22602
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  /17

  $475,000

  • Land
  • 89.87 Acres
  • $5,285 per Acre

  0 Shockeysville Rd Unit VAFV2041652, Winchester, VA 22603

  Approximately 90-acre wooded parcel offering abundant space for recreation, hunting, and enjoying nature, with Little Brush Creek bordering the property. This private retreat features approximately 2,500 feet of creek frontage and has been recently surveyed. The property is accessed by frontage on Shockyeville Road or established easement and offers a peaceful, remote setting while still being

  Brandi Marcum Pearson Smith Realty, LLC

  0 Shockeysville Rd Unit VAFV2041652, Winchester, VA 22603
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  /22

  $369,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,000 Sq Ft

  HOMESITE 44 Shuoner Ct, Winchester, VA 22602

  110 SHUONER Ct – Model Home | We Have spec homes Summer 2026 Delivery AvailableSt. Paul TBB | 4 BR | 3.5 BA | 1-Car Garage | Finished Lower Level + Larger Deck Beautiful wooded homesites available!Offering up to 2,000 sq. ft. of modern, open-concept living — customize your home the way you like, or keep everything as-is at this price, including a 4th bedroom. Home Highlights Open-concept

  Jimmy Thomas New Home Star Virginia, LLC

  HOMESITE 44 Shuoner Ct, Winchester, VA 22602
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  /2

  $1,800,000

  • Land
  • 4.93 Acres
  • $365,112 per Acre

  0 Sulky Dr, Winchester, VA 22602

  4.93 acres with great interstate exposure. End of cul de sac. Owners have proposed platt showing parcel subdivided into 4 parcels

  Jeff Webber Long & Foster Real Estate, Inc.

  0 Sulky Dr, Winchester, VA 22602
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  /11

  $90,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  107 Cutshaws Ct Unit C345, Winchester, VA 22603

  Welcome to Regency Lakes a all age active and vibrant community, where you can find yourself close to all the action, while maintaining that country feel. We have a 2002 3 bed, 2 bath home for sale featuring 1568.00 sq ft of beautifully designed living space. Located in/near Winchester, this property offers the perfect blend of modern amenities and timeless charm. Step inside to find a large

  Kristina Kelly Regency Lakes

  107 Cutshaws Ct Unit C345, Winchester, VA 22603
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  /47

  $542,990

  New Construction

  • 5 Beds
  • 3.5 Baths
  • 2,618 Sq Ft

  SALEM Plan at Retreat at Winding Creek - Single Family, Winchester, VA 22602

  Welcome to the Salem floor plan, available at Retreat at Winding Creek, VA. This is one of our most popular floorplans. On the main floor, you will find a formal dining room, laundry room, and powder room. The open-concept kitchen and living areas are perfect for entertaining. The kitchen boasts a breakfast nook, a pantry, and an island with countertop seating. From the breakfast nook, you can

  D.R. Horton Builder

  137 Seminole Dr Unit 36203783, Winchester, VA 22602
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  /17

  $525,990

  New Construction

  • 5 Beds
  • 3 Baths
  • 2,415 Sq Ft

  130 Wappinger Terrace, Winchester, VA 22602

  Discover the perfect blend of space, function, and style in the Elm—a thoughtfully designed 2,415 sq. ft. two-story home featuring 5 bedrooms, 3 full bathrooms, a versatile loft, and a 2-car garage. Step into a welcoming foyer that opens to a bright, open-concept living area. The heart of the home is the spacious kitchen, complete with stainless steel appliances, generous cabinet storage, a

  D.R. Horton Builder

  130 Wappinger Terrace, Winchester, VA 22602
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  /2

  $215,000

  • Land
  • 40,075 Sq Ft
  • $233,696 per Acre

  0 7 Building Lots In Shawneeland Unit VAFV2032844, Winchester, VA 22602

  REDUCED by $20k! CALLING ALL BUILDERS!! 7 BUILDING LOTS for $215,000 (being sold as a bundle) located in Shawneeland in Frederick County, VA. . Perc approved certification letter, plat and sewer docs on file for each lot. The lots range in size from 0.40-0.92 acres. Potential home sites for permanent home or weekends and vacations. Enjoy hiking, fishing, swimming in the lake, nature walks and

  Caroline W. Barb, REALTOR Jim Barb Realty, Inc.

  0 7 Building Lots In Shawneeland Unit VAFV2032844, Winchester, VA 22602
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  /11

  $249,900

  • Land
  • 7.1 Acres
  • $35,197 per Acre

  384 Frog Hollow Rd, Winchester, VA 22603

  7 scenic acres with no restrictions and endless potential. Offering over 450' feet of road frontage, this beautiful parcel features a gentle slope and a thoughtfully prepared layout for future development. A partially cleared area is ready for a potential homesite, with an additional cleared septic location already in place. Current owner is in the process of obtaining well and septic

  Jennifer Sacco RE/MAX Roots

  384 Frog Hollow Rd, Winchester, VA 22603
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  /7

  $139,800

  • Land
  • 2.03 Acres
  • $68,867 per Acre

  0 Wardensville Grade Unit VAFV2042390, Winchester, VA 22602

  Build your dream home on this beautiful 2.03-acre wooded parcel in a desirable Winchester location! Enjoy the perfect combination of privacy and convenience, with easy access to Valley Health, schools, shopping, and Route 37.The current owner has already completed much of the groundwork, making this property ready for your building plans. The lot features an approved 4-bedroom/8-person sewage

  Sandra Brookman RE/MAX Real Estate Connections

  0 Wardensville Grade Unit VAFV2042390, Winchester, VA 22602
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  /49

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  1355 Perry Rd, Winchester, VA 22602

  This beautifully remodeled home showcases quality and attention to detail from the moment you step inside. The kitchen has been completely transformed with abundant cabinetry, generous counter space, and brand-new stainless steel appliances, creating both style and functionality. Throughout the home, you will find new flooring, doors, trim, and fresh paint, giving every room a clean, modern feel.

  Roxane Morrison NextHome Realty Select

  1355 Perry Rd, Winchester, VA 22602

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