Winchester, VA 2-Story Homes for Sale

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  $579,900

  • 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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  $649,999

  • 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
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  $735,000

  • 4 Beds
  • 3 Baths
  • 3,482 Sq Ft

  1419 Ramseur Ln, Winchester, VA 22601

  This property is NOT in a 55+ community. A rare opportunity for one-level living with over 3,400 finished sq ft in Early’s Green at Meadowbranch. This 4 bedroom, 3 bath brick-front rancher offers a fully finished basement with a custom built bar, a chef’s kitchen, and major upgrades including a Generac whole-house generator and new HVAC (2024). The finished lower level functions as an ideal guest

  Sheila Pack RE/MAX Roots

  1419 Ramseur Ln, Winchester, VA 22601
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  $749,000 Open Sat 2PM - 4PM

  • 5 Beds
  • 3.5 Baths
  • 4,008 Sq Ft

  174 Williamson Rd, Winchester, VA 22602

  OPEN HOUSE CANCELLED. If you want more space and are priced out of Northern Virginia, come to Winchester! If you don't want to wait 6-9 months, this home is ready now and better than new! No wait, no extra costly upgrades needed. Move into this fully finished 2023 built main level living home with space, style, and flexibility already built in. Why wait for new construction when this home is

  Joyce Santiago Century 21 Redwood Realty

  174 Williamson Rd, Winchester, VA 22602
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  $884,000

  • 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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  $549,990

  • 4 Beds
  • 3.5 Baths
  • 3,132 Sq Ft

  308 Lehigh Dr, Winchester, VA 22602

  Welcome to 308 Lehigh Drive, a beautifully updated and move-in ready home offering the perfect blend of space, style, and comfort. Built in 2023 - this modern, open-concept floor plan is filled with natural light and designed for effortless everyday living and impressive entertaining. The heart of the home is the chef’s kitchen, complete with a gas cooktop, built-in wall oven and microwave,

  Sean Smith Real Broker, LLC

  308 Lehigh Dr, Winchester, VA 22602
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  $456,500

  • 3 Beds
  • 2 Baths
  • 2,094 Sq Ft

  101 Delaware Trail, Winchester, VA 22602

  Welcome to 101 Delaware Trail, a thoughtfully updated home nestled in the highly desirable Shawneeland community of Winchester, VA. Nearly the entire home has been updated, both inside and out, creating a fresh and modern living experience. Interior improvements include new flooring throughout (excluding existing wood flooring), an updated kitchen featuring Taj Mahal quartzite countertops, a

  Michael Putnam EXP Realty, LLC

  101 Delaware Trail, Winchester, VA 22602
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  $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
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  $395,000

  • 3 Beds
  • 2.5 Baths
  • 1,630 Sq Ft

  116 Maury Way, Winchester, VA 22602

  Welcome home! This lovely and charming end-unit townhome is nestled in the sought-after active adult community of Winchester Landing. Why wait for the builders when you can have a better than new home right now?! Perfectly located on the east side of Winchester, everything you need is conveniently close by; shopping, restaurants, amenities, and all the commuter routes. This spacious home is

  Amanda White Nova Home Hunters Realty

  116 Maury Way, Winchester, VA 22602
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  $479,900 Open Sat 11:30AM - 1:30PM

  • 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
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  $424,990

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft

  110 Elaine Dr, Winchester, VA 22602

  Just signing a lease Friday 3/27/2026, house will be removed final signature is done.

  JoAnn Walker Century 21 Redwood Realty

  110 Elaine Dr, Winchester, VA 22602
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  $299,000

  • 1,249 Sq Ft

  45 and 45 1/2 Race St, Winchester, VA 22601

  Time to sell - buyer get s deal - $36,000 rental income, low maintenance, tenants in place. This is a great starter property for those looking to build a real estate portfolio or add to an existing one. Both apartments were completely rehabbed last year - new wiring and plumbing, new appliances, including washer and dryer, new carpet and vinyl plank flooring installed and fenced backyards.

  Teri Domanski Corcoran McEnearney

  45 and 45 1/2 Race St, Winchester, VA 22601
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  $525,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,280 Sq Ft

  157 Oak Dr, Winchester, VA 22603

  STOP THE PRESSES!! This PRICE ADJUSTMENT is not a typo! The weather is warmer and Spring is in the air.... This home is ready for YOU! Welcome home to 157 Oak Dr. in Winchester, VA—an inviting property offering comfort, thoughtful updates, and a peaceful setting. This home has been refreshed with luxury vinyl plank flooring throughout most of the home and fresh paint, creating a clean,

  Phyllis Guthrie Keller Williams Realty

  157 Oak Dr, Winchester, VA 22603
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  $450,000

  • 4 Beds
  • 2.5 Baths
  • 2,072 Sq Ft

  129 Doonbeg Ct, Winchester, VA 22602

  ENJOY YOUR RETIREMENT! Newer, beautifully maintained 4-bedroom home with open floor plan and upgrades. On a pleasant cul-de-sac in Cottage Glen, an age 55-plus community that's convenient to I-81 and Rt. 37 and near restaurants, shopping, services, regional Medical Center and historic downtown Winchester. National publications and TV have hailed Winchester as a prime location for retirement.

  Teresa Strohmeyer ERA Oakcrest Realty, Inc.

  129 Doonbeg Ct, Winchester, VA 22602
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  $489,999

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

  3466 Middle Rd, Winchester, VA 22602

  Welcome to a private retreat where timeless charm meets peaceful mountain beauty. Set on 0.59 acres of fully fenced, professionally landscaped grounds, this all-brick hillside home offers breathtaking views of the Blue Ridge Mountains along a quiet stretch of Middle Road. Inside, sunlight pours through expansive living spaces, creating a warm and inviting atmosphere. The open-concept design flows

  LESLIE WEBB Long & Foster Real Estate, Inc.

  3466 Middle Rd, Winchester, VA 22602
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  $384,900

  • 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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  $550,000

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft

  289 Westview Dr, Winchester, VA 22603

  Welcome to your private contemporary retreat at 289 Westview Drive in Winchester, VA! This truly exceptional property offers the ultimate escape, situated on over 13 magnificent acres with gorgeous mature trees, stunning views, and unparalleled peace and quiet. Step inside the sun-filled main level, featuring an open layout that seamlessly connects the living room, dining room, and kitchen.

  Dan Whitacre Colony Realty

  289 Westview Dr, Winchester, VA 22603
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  $414,999

  • 3 Beds
  • 2 Baths
  • 2,131 Sq Ft

  204 Ridge Rd, Winchester, VA 22602

  Well maintained brick Rancher(upgraded vinyl clad tilt windows,newer architectural roof) on a full basement on the east side of Winchester featuring over 2100 sqft of finished living space that offers true hardwood flooring on the main level with 3 bedrooms and 1 full bath. Spacious living room that features a gas log fireplace that has a woodstove insert included. Basement is 90% finished with a

  James Amick RE/MAX Roots

  204 Ridge Rd, Winchester, VA 22602
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  $2,125,000

  • 5 Beds
  • 4 Baths
  • 4,166 Sq Ft

  1631 Back Mountain Rd, Winchester, VA 22602

  This unique property is the definition of an oasis in the woods. Surrounded by 180 glorious private acres, this home dazzles with grandeur while blending natural elements that mesh with the environment. The handsome hunter green standing seam metal roof with matching accents against wood siding is the ideal look for this 4,166 square foot architectural marvel. Indoors, there’s a thoughtful

  Dan Whitacre Colony Realty

  1631 Back Mountain Rd, Winchester, VA 22602
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  /20

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft

  553 Highland Ave, Winchester, VA 22601

  Don't miss taking a LOOK at this property with the new low price of $319K. One Way street = quiet Gorgeous Rehab - you have to see it! Secure Parking off the alley Efficient HVAC mini splits installed Washer and Dryer included

  Teri Domanski Corcoran McEnearney

  553 Highland Ave, Winchester, VA 22601
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  $654,000

  • 6 Beds
  • 4 Baths
  • 3,511 Sq Ft

  1400 Valley Ave, Winchester, VA 22601

  Versatile on Valley! So many possibilities! This versatile duplex is full of charm and opportunity! The original 1936 home features beautiful wood floors, tall ceilings, fireplace, sunroom, and a stunning staircase that adds timeless character. The front unit is perfect for an owner-occupant who wants to enjoy historic charm while generating income from the back unit, or you can rent out both

  Danielle Spriggs Real Broker LLC

  1400 Valley Ave, Winchester, VA 22601
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  $767,900

  • 3 Beds
  • 3 Baths
  • 2,112 Sq Ft

  1049 Laurel Grove Rd, Winchester, VA 22602

  This custom-built 3-bedroom, 3-bath home is perfectly positioned on a private, wooded lot with sweeping mountain views and a sense of seclusion. The setting feels like a peaceful retreat, offering a serene, park-like atmosphere while still providing convenient access to everyday amenities. The main-level primary suite is a standout, featuring an elegant bathroom with a walk-in shower and a

  LESLIE WEBB Long & Foster Real Estate, Inc.

  1049 Laurel Grove Rd, Winchester, VA 22602
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  $335,000

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

  1004 S Cameron St, Winchester, VA 22601

  Renovated 3-bedroom detached home for just $335,000!- -Tucked away on a private 7,840 sq. ft. lot in Winchester. This charming single home gives you the one thing that condos and townhouses can’t; freedom. No shared walls, no stairs, and absolutely no HOA telling you what color your door can be.- -Step inside and you’ll instantly feel it, the calm of a bright,

  Patricia Salgado Metas Realty Group, LLC

  1004 S Cameron St, Winchester, VA 22601
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  $370,000

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  2431 Cedar Creek Grade, Winchester, VA 22602

  This is a unique opportunity to purchase a piece of history. The Glass Mill (Glass/Rinker/Cooper Mill) is available. The Mill was constructed during the years 1812-1815. At the base, the structure has stone walls that are 3' thick, tapering to about half that at the gable ends. The Mill has a "mechanics level", the lower level with dirt floor and water source when the Grist wheel was in place.

  Edward Beightol Cedar Creek Real Estate

  2431 Cedar Creek Grade, Winchester, VA 22602
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  $239,900

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  139 Little River Dr, Winchester, VA 22602

  Rebecca Sims Century 21 Redwood Realty

  139 Little River Dr, Winchester, VA 22602
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  $374,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 1,752 Sq Ft

  115 Castaway Place, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  Brookfield Residential Builder

  115 Castaway Place, Winchester, VA 22603
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  $579,990 New Construction

  • 5 Beds
  • 4 Baths
  • 2,511 Sq Ft

  119 Wappinger Terrace, Winchester, VA 22602

  The Hayden is a spacious two-story home featuring 6 bedrooms and 4 bathrooms across more than 3200 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 an oversized island with seating, a large pantry, and opens to the dining area and expansive living room. A main-level bedroom with a full bathroom

  D.R. Horton Builder

  119 Wappinger Terrace, Winchester, VA 22602
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  $584,990 New Construction

  • 5 Beds
  • 4 Baths
  • 2,511 Sq Ft

  121 Wappinger Terrace, Winchester, VA 22602

  The Hayden is a spacious two-story home featuring 6 bedrooms and 4 bathrooms across more than 3200 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 an oversized island with seating, a large pantry, and opens to the dining area and expansive living room. A main-level bedroom with a full bathroom

  D.R. Horton Builder

  121 Wappinger Terrace, Winchester, VA 22602
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  $519,990 New Construction

  • 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

  Brooks Sears D R Horton Realty of Virginia LLC

  122 Trellis View Ln, Winchester, VA 22602
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  /19

  $658,490 New Construction

  • 4 Beds
  • 3 Baths
  • 2,712 Sq Ft

  249 Hydrangea Way, Winchester, VA 22602

  he Dover by D.R. Horton offers 1,958 square feet of thoughtfully designed, single-level living with 3 bedrooms, 2 full baths, and a 2-car garage. A private flex room with LVP flooring sits just off the foyer – ideal for a home office or craft room.9-foot ceilings lead into the open-concept kitchen, dining, and family room. The kitchen features quartz countertops, soft-close cabinet doors, a

  Brooks Sears D R Horton Realty of Virginia LLC

  249 Hydrangea Way, Winchester, VA 22602
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  $521,490 New Construction

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

  116 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

  Brooks Sears D R Horton Realty of Virginia LLC

  116 Trellis View Ln, Winchester, VA 22602
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  /42

  $526,490 New Construction

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

  120 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

  Brooks Sears D R Horton Realty of Virginia LLC

  120 Trellis View Ln, Winchester, VA 22602
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  $679,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,850 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 Main Level Living Evergreene model with standard 13' Family Rm 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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  $799,900 New Construction

  • 3 Beds
  • 2 Baths
  • 2,139 Sq Ft

  169 Cather Ln, Winchester, VA 22602

  Estimated completion August 2026. Photos shown are of a similar home previously constructed by the builder. Finishes and features may vary. Welcome to 169 Cather Lane, a spacious rancher situated on 5 beautiful pastoral acres with stunning views and an unbeatable location just minutes from town. Built by local builder Scott & Scott Construction, this home offers the perfect blend of quality

  Kaitlyn Behr Samson Properties

  169 Cather Ln, Winchester, VA 22602
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  $579,990 New Construction

  • 6 Beds
  • 4.5 Baths
  • 2,632 Sq Ft

  123 Wappinger Terrace, Winchester, VA 22602

  Quick Move-In Salem! This spacious 6 bedroom, 4.5 bath home offers 2,686 sq ft on the top two floors with a first-floor primary suite for easy main-level living. The open-concept design is perfect for entertaining, and the stone front elevation adds timeless curb appeal. Enjoy the added space of a finished recreation room with an additional bedroom—ideal for guests or a home office. Ask about

  D.R. Horton Builder

  123 Wappinger Terrace, Winchester, VA 22602
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  $509,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,953 Sq Ft

  124 Wappinger Terrace, Winchester, VA 22602

  The Pine offers 1,964 square feet of modern living space - perfect for growing families or those who love to entertain. This well-designed single family home includes four spacious bedrooms, two and a half bathrooms, and a two-car garage on slab foundation. The open-concept design showcases a contemporary kitchen with stainless steel appliances, quartz countertops, and white cabinetry - combining

  D.R. Horton Builder

  124 Wappinger Terrace, Winchester, VA 22602
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  $699,990 New Construction

  • 6 Beds
  • 4 Baths
  • 2,511 Sq Ft

  104 Wappinger Terrace, Winchester, VA 22602

  The Hayden is a spacious two-story home featuring 6 bedrooms and 4 bathrooms across more than 6,000 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 an oversized island with seating, a large pantry, and opens to the dining area and expansive living room. A main-level bedroom with a full bathroom

  D.R. Horton Builder

  104 Wappinger Terrace, Winchester, VA 22602
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  /20

  $399,900 New Construction

  • 3 Beds
  • 3 Baths
  • 1,914 Sq Ft

  208 Beaver Trail, Winchester, VA 22602

  3-22-26 foundation going in this week and 60 days to complete. Stunning 3BR/3BA home on 0.33+ acre lot with public water & available Xfinity internet. Easy entrance access. Open floor plan features vaulted family room & kitchen. Upgraded kitchen boasts Bonus Granite Island & premium cabinets. Luxury finishes include hardwood throughout the entire main floor, stairs & bedrooms, plus tile in all

  Jim Thomson Realty ONE Group Old Towne

  208 Beaver Trail, Winchester, VA 22602
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  /24

  $549,990 New Construction

  • 2,050 Sq Ft

  112 Zinnia Ln, Winchester, VA 22603

  This stunning twin/semi-detached home, set to be completed this spring6, embodies the perfect blend of elegance and comfort, offering a warm and inviting atmosphere. Step inside to experience an open floor plan that seamlessly connects the family room and kitchen, ideal for entertaining or enjoying quiet evenings at home. The kitchen features a spacious island, perfect for culinary creations,

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  112 Zinnia Ln, Winchester, VA 22603
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  /16

  $379,990 New Construction

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  106 Heirloom Way, Winchester, VA 22603

  This stunning two-level villa boasts a modern open concept design that seamlessly connects living spaces for an inviting and spacious feel. The main level features a living room that opens effortlessly to the dining area, creating a perfect space for entertaining and family gatherings. The expansive rear kitchen includes an L-shaped layout with an eating bar and an island with additional bar

  Brookfield Residential Builder

  106 Heirloom Way, Winchester, VA 22603

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