Winchester, VA 2-Story Homes for Sale

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  $749,990 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,614 Sq Ft

  154 Williamson Rd, Winchester, VA 22602

  The Carlisle home design by Maronda Homes offers the perfect balance of style, space, and flexibility—designed to meet the needs of modern families and active lifestyles. Featuring 4 to 6 bedrooms, 2.5 to 5 bathrooms, and 3,614 square feet of living space, the Carlisle provides room to grow without sacrificing comfort or function.From the welcoming front entry to the spacious open-concept layout,

  

  Maronda Homes

  Builder

  154 Williamson Rd, Winchester, VA 22602
• Explore Winchester

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  $875,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,957 Sq Ft

  1681 Airport Rd, Winchester, VA 22602

  Professional photos coming soon**Tucked away on a quiet drive in Winchester, VA, this stunning Colonial-style home blends timeless charm with modern comfort on over 18 acres of serene, private land. Perfect for anyone seeking peace, space, and a true connection to nature, this property offers an exceptional lifestyle both inside and out. Step inside to a warm, inviting interior featuring rich

  

  Kimberly Teska

  Coldwell Banker Premier

  (540) 701-7447

  1681 Airport Rd, Winchester, VA 22602
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  /45

  $549,000

  • 4 Beds
  • 3 Baths
  • 2,652 Sq Ft

  112 Westwood Cir, Winchester, VA 22602

  NO HOA! ALL brick rambler nestled on a corner 1/2 an acre of mature trees lot in Winchester right off Route 522 and 2 miles to I-81! This spacious home (over 2,600 square feet of finished living space on ONE LEVEL) features 4 generously sized bedrooms and 3 full bathrooms, offering comfort and flexibility for any lifestyle. The heart of the home is an oversized kitchen with updates—stainless

  

  Christine Dean

  Hunt Country Sotheby's International Realty

  (540) 503-3289

  112 Westwood Cir, Winchester, VA 22602
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  /2

  $250,000

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

  523 Monticello St, Winchester, VA 22601

  Sold "As-IS" Nice investment or starter property. Needs a little updating. Hardwoods throughout upstairs and living room downstairs. This price includes 525 Monticello lot. Tax ID #330-02-19. If any questions call listing agent. Agent related to seller.

  

  Ned Stock

  Berkshire Hathaway HomeServices PenFed Realty

  (540) 305-3611

  523 Monticello St, Winchester, VA 22601
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  $1,200,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,284 Sq Ft

  80 Gough Rd, Winchester, VA 22602

  Dreaming of your own farmette, private estate, or peaceful country retreat?This is a rare opportunity to create what you're searching for on a premium 8-acre lot offering gorgeous mountain views, usable acreage, and a truly scenic setting. The elevated homesite sits approximately 800 feet off Cedar Creek Grade with frontage on Gough Road, providing privacy while still offering easy access to

  

  Bradley Comstock

  ERA Oakcrest Realty, Inc.

  (540) 781-0968

  80 Gough Rd, Winchester, VA 22602
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  /2

  $799,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,331 Sq Ft

  123 Stetson St, Winchester, VA 22603

  Don’t miss this incredible opportunity to own a brand-new ranch home set on 2.66 beautiful acres, conveniently located near shopping and commuter routes to Winchester, Martinsburg, and Northern Virginia and approximately 10 minutes from the Winchester Medical Center. This thoughtfully designed home features an open-concept layout with a desirable split-bedroom design, offering both comfort and

  

  Brett Sowder

  RE/MAX Roots

  (540) 619-5465

  123 Stetson St, Winchester, VA 22603
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  /13

  $674,990 New Construction

  • 3 Beds
  • 3 Baths
  • 3,056 Sq Ft

  156 Williamson Rd, Winchester, VA 22602

  *****INVESTMENT OPPORTUNITY****** The DREXEL MODEL HOME with leaseback-great investment opportunity! All the upgrades! With 3,213 finished square feet, the Drexel offers generous living space, Must see ranch home with 3 Bedrooms & 3 baths! It features main-level living, including a private master suite with a walk-in closet and en-suite bathroom, along with two full bathrooms on the main level

  Holly Horne Poole

  New Home Star Virginia, LLC

  (540) 306-5271

  156 Williamson Rd, Winchester, VA 22602
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  /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
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  /33

  $595,990 New Construction

  • 4 Beds
  • 2.5 - 3.5 Baths
  • 3,383 Sq Ft

  Birmingham Plan at Abrams Pointe, Winchester, VA 22602

  The Birmingham home design offers a harmonious blend of space, comfort, and elegance, perfect for families who value both form and function. With 4 bedrooms, 2.5 to 3.5 bathrooms, and 3,383 square feet of thoughtfully designed living space, the Birmingham is a home that adapts to your lifestyle.Step through the welcoming foyer into a bright, open-concept layout that includes a flex space for a

  Maronda Homes Builder

  161 Williamson Rd Unit 37110033, Winchester, VA 22602
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  /56

  $605,990 New Construction

  • 4 - 6 Beds
  • 2.5 - 5.5 Baths
  • 3,614 Sq Ft

  Carlisle Plan at Abrams Pointe, Winchester, VA 22602

  The Carlisle home design by Maronda Homes offers the perfect balance of style, space, and flexibility—designed to meet the needs of modern families and active lifestyles. Featuring 4 to 6 bedrooms, 2.5 to 5 bathrooms, and 3,614 square feet of living space, the Carlisle provides room to grow without sacrificing comfort or function.From the welcoming front entry to the spacious open-concept layout,

  Maronda Homes Builder

  161 Williamson Rd Unit 37110558, Winchester, VA 22602
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  /23

  $374,990 New Construction

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

  Northgate Plan at Hiatt Pointe at Snowden Bridge - 55+ Villas Collection, 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

  105 Wagtail Ln Unit 36578847, Winchester, VA 22603
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  /41

  $619,959 New Construction

  • 3 Beds
  • 3 Baths
  • 3,203 Sq Ft

  112 Magpie Ln Unit HOMESITE 1036, Winchester, VA 22603

  Discover the Sierra 39-F2 – Homesite 1036 at Hiatt Pointe 55+ by Van Metre Homes in Winchester, VA—a two-car, front-load garage SINGLE FAMILY HOME with three bedrooms and three full bathrooms, ready for you to move in IMMEDIATELY. Designed for ease and everyday function, this floorplan has everything you need! This residence welcomes you with a spacious covered front porch and 9’ ceilings on all

  Shannon L Bray Pearson Smith Realty, LLC

  112 Magpie Ln Unit HOMESITE 1036, Winchester, VA 22603
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  $460,290 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,257 Sq Ft

  0 Wagtail Ln Unit VALE 34-F2, Winchester, VA 22603

  Find a new 55+ VILLA HOME by Van Metre Homes at Hiatt Pointe (55+) in Winchester, VA that will be ready for you to move in 2026. Welcome to the Vale 34-F2 at Hiatt Pointe—a two-car, front-load garage villa with three bedrooms, two full bathrooms, and one half bathroom. Open and adaptable, this floorplan is centered around the gourmet kitchen that brings connection to the heart of the home. The

  Shannon L Bray Pearson Smith Realty, LLC

  0 Wagtail Ln Unit VALE 34-F2, Winchester, VA 22603
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  $448,119 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,181 Sq Ft

  108 Keystone Unit HOMESITE 1094, Winchester, VA 22603

  Embrace the Vera 30-F2 – Homesite 1094 at Hiatt Pointe in Winchester by Van Metre Homes—a two-car, front-load garage END VILLA HOME with three bedrooms, two full bathrooms, and one half bathroom ready for you to move in IMMEDIATELY. Built for the way you live, this factory-framed floorplan makes room for moments big and small with its natural flow. Be welcomed by 9’ ceilings on both levels,

  Shannon L Bray Pearson Smith Realty, LLC

  108 Keystone Unit HOMESITE 1094, Winchester, VA 22603
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  $397,990 New Construction

  • 3 Beds
  • 2.5 - 3.5 Baths
  • 1,966+ Sq Ft

  St Paul Plan at Winchester Ridge Townhomes, Winchester, VA 22602

  Introducing the St. Paul, one of Maronda’s latest townhome designs.The St. Paul offers a range of 1,966 to 1,989 square feet of living space, including 3 to 4 bedrooms, 2.5 to 3.5 bathrooms, and a spacious 1-car garage. This new design offers plenty of personalization opportunities to fit your family’s unique needs.On the first floor of the home, you will find a spacious, open-concept floor plan.

  Maronda Homes Builder

  161 Williamson Rd Unit 37409245, Winchester, VA 22602
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  $585,990 New Construction

  • 4 Beds
  • 2.5 - 3.5 Baths
  • 3,194 Sq Ft

  Somerset Plan at Abrams Pointe, Winchester, VA 22602

  The Somerset home design by Maronda Homes is designed with today’s lifestyle in mind—blending open-concept living, functional spaces, and refined details into one beautifully crafted home. With 4 bedrooms, 2 to 4 bathrooms, and 3,194 square feet of living space, the Somerset offers flexibility for families at every stage of life.The heart of the home is the expansive great room, which opens to a

  Maronda Homes Builder

  161 Williamson Rd Unit 37110563, Winchester, VA 22602
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  /56

  $564,990 New Construction

  • 4 Beds
  • 2.5 - 3.5 Baths
  • 2,533 Sq Ft

  Rockford Plan at Abrams Pointe, Winchester, VA 22602

  The Rockford home design offers a thoughtful blend of modern functionality and classic comfort, perfect for homeowners who value both style and efficiency. With 4 bedrooms, 2 to 3 bathrooms, and 2,533 square feet of living space, the Rockford is an ideal choice for first-time buyers, growing families, or anyone looking to right-size their lifestyle.Step inside to find an inviting open-concept

  Maronda Homes Builder

  161 Williamson Rd Unit 37110038, Winchester, VA 22602
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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
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  $509,000

  • 4 Beds
  • 3 Baths
  • 1,935 Sq Ft

  4494 Cedar Creek Grade, Winchester, VA 22602

  Escape to Your Private Almost 3-Acre Oasis: The Ultimate Modern Homestead!Rarely does a property offer the perfect synergy of a high-end interior renovation and a fully functional hobby farm. Nestled on a lush, 2.87-acre lot, this stunning 4-bedroom, 3-full bath home has been reimagined from top to bottom. As you enter the circular driveway lined with budding spring trees, you’ll feel the

  Jaclyn Michelle Berkshire Hathaway HomeServices PenFed Realty

  4494 Cedar Creek Grade, Winchester, VA 22602
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  /17

  $255,000 Open Sat 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  136 Parkside Dr, Winchester, VA 22602

  Great Investment property or 1st home! Charming and spacious 2 bedroom, 1.5 baths Townhouse. Extra large living room has hardwood floors, lots of natural light, Eat in Kitchen with full size washer & dryer and powder room on the main level. Back door opens to fenced backyard with small storage area. Upstairs has two XL large bedrooms (can fit a king & queen bed), both with hardwood floors, 2

  Nancy Tessman EXP Realty, LLC

  136 Parkside Dr, Winchester, VA 22602
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  $585,000

  • 4 Beds
  • 2.5 Baths
  • 2,909 Sq Ft

  328 Sheridan Ave, Winchester, VA 22601

  Timeless charm meets thoughtful updates in this beautifully maintained all-brick 1958 home, offering effortless one-level living with a warm retro vibe. Freshly painted throughout and enhanced with new quartz countertops, classic subway tile backsplash, updated sink and faucet, and stylish new lighting, this home blends character with modern comfort. The main level is inviting and functional,

  Mary Casselano Dream Real Estate

  328 Sheridan Ave, Winchester, VA 22601
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  $360,000

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  16 S Pleasant Valley Rd, Winchester, VA 22601

  Welcome to this one-of-a-kind property offering a unique and inviting layout designed with a seamless flow from front to back, filled with natural light throughout. Start your mornings on the rear patio enjoying peaceful sunrise views, and unwind in the evenings on the welcoming front porch with beautiful sunsets — the best of both worlds right at home.This home has been thoughtfully updated

  Vanessa Couture Samson Properties

  16 S Pleasant Valley Rd, Winchester, VA 22601
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  $425,000 Open House 4/11

  • 4 Beds
  • 2.5 Baths
  • 2,353 Sq Ft

  111 Asbury Rd, Winchester, VA 22602

  Located on the east side of Winchester, this split-level home offers both comfort and convenience with easy access to Route 7 for commuting to Northern Virginia, I-81, and nearby shopping and dining.The home features a functional layout with additional finished living space on the lower level, including a bedroom and half bath, making it ideal for guests, a home office, or a private

  Sharon Farinholt Realty ONE Group Old Towne

  111 Asbury Rd, Winchester, VA 22602
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  $649,900

  • 4 Beds
  • 3.5 Baths
  • 4,419 Sq Ft

  151 Darby Dr, Winchester, VA 22602

  Lovely contemporary home in the established Ravenwing subdivision, featuring a highly desirable main-level primary suite and a layout you’ll instantly fall in love with. The well-designed floor plan offers spacious second-floor bedrooms, a finished basement complete with a kitchenette, and a screened rear porch overlooking a fenced yard. Enjoy peaceful views of the picturesque common area and

  Dave Spence RE/MAX Roots

  151 Darby Dr, Winchester, VA 22602
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  /94

  $795,000

  • 5 Beds
  • 4 Baths
  • 4,075 Sq Ft

  274 Woodside Ln, Winchester, VA 22603

  Welcome to 274 Woodside - a secluded house on 5.06 acres with tons of storage! This 4,310 SF rambler style home has 2 masters (one up and one down), 4 bathrooms (2 on the main floor have heated floors), a huge kitchen with tons of cabinets, a large island with a 5 burner propane cooktop, and a pantry cabinet with pull-out shelves for storage, two fireplaces - one propane and one wood-burning

  Cindy Butler Virginia Property Group, Inc.

  274 Woodside Ln, Winchester, VA 22603
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  $450,000

  • 3 Beds
  • 3 Baths
  • 2,860 Sq Ft

  320 Shawnee Trail, Winchester, VA 22602

  Located in Emerald Lake Subdivision-NO HOA . Welcome to your very own treehouse retreat surrounded by mature trees, mountain views, and exceptional privacy on 1.86 acres with a Private POOL! This property is designed for outdoor living, featuring a covered front porch, a large back deck with scenic views, and a beautifully crafted stone patio with a fire pit—perfect for entertaining or relaxing

  Stacey Mullins ERA Oakcrest Realty, Inc.

  320 Shawnee Trail, Winchester, VA 22602
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  /55

  $585,000

  • 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
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  /22

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 1,296 Sq Ft

  407 Emily Ln, Winchester, VA 22602

  Don't miss your opportunity to own this turn key, meticulously maintained 3 bedroom/2.5 bath townhome in sought after Carlisle Heights! The main level is the heart of the home and features gleaming hardwood flooring throughout, a large living room, gourmet updated kitchen with white cabinetry, stainless steel appliances, quartz counters and a modern sink that opens to an oversized dining room.

  Paul Thistle Take 2 Real Estate LLC

  407 Emily Ln, Winchester, VA 22602
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  $255,000

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  138 Parkside Dr, Winchester, VA 22602

  Great investment opportunity! This tenant-occupied property is currently rented for $1,650/month with a lease in place through January 2027, offering immediate income. Ideal for investors looking for a turnkey rental. Seller is motivated, don’t miss this opportunity! Welcome to 138 Parkside Drive, a charming 3-bedroom, 1.5-bath townhome in a quiet, convenient Winchester neighborhood! This home

  Jas Kaur Prime Properties DMV, LLC.

  138 Parkside Dr, Winchester, VA 22602
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  /63

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,999 Sq Ft

  520 N Braddock St, Winchester, VA 22601

  Welcome to this charming home in the heart of Winchester offering character, natural light, and a highly walkable location.This home features 3 bedrooms and 2 full bathrooms, with all bedrooms located on the upper level. At the top of the stairs you’ll find a spacious primary bedroom filled with natural light, creating a bright and inviting retreat. Large windows throughout the home allow

  Angela Duncan MarketPlace REALTY

  520 N Braddock St, Winchester, VA 22601
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  /30

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  616 Cardinal Dr, Winchester, VA 22602

  Nestled in the serene Wilde Acres community, this exquisite split foyer home, built in 2024, offers a harmonious blend of modern luxury and inviting comfort. With three spacious bedrooms and two full bathrooms, this residence is designed for both relaxation and entertaining, making it the perfect sanctuary for those who appreciate the finer things in life. Step inside to discover a thoughtfully

  Brett Shankle Samson Properties

  616 Cardinal Dr, Winchester, VA 22602
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  /3

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,505 Sq Ft

  101 Maury Way, Winchester, VA 22602

  Winchester Landing, 55+ End-Unit Townhome with GarageA private main level bedroom and two upstairs. Kitchen walks out to back patio and landscaping is very nice.Lots of light and open space, in great condition.Stainless appliances, walk-out to spacious back patio, full size washer & dryer.Active-adult community, lawn maintenance included, Great Location.

  Anita Hartke National Realty, LLC

  101 Maury Way, Winchester, VA 22602
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  /36

  $429,000

  • 3 Beds
  • 2.5 Baths
  • 1,528 Sq Ft

  209 Wood Ave, Winchester, VA 22601

  Welcome to this beautifully-updated brick rancher, a masterclass in blending timeless character with high-end, modern sophistication. From the moment you arrive, the covered front porch and classic silhouette command attention, offering undeniable curb appeal in one of Winchester’s most sought-after locations. Step inside to find a main level bathed in natural light, showcasing gleaming hardwood

  Dan Whitacre Colony Realty

  209 Wood Ave, Winchester, VA 22601
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  /56

  $349,900

  • 4 Beds
  • 2.5 Baths
  • 2,058 Sq Ft

  224 Doe Trail, Winchester, VA 22602

  Welcome home to this spacious 4-bedroom, 2.5-bath ranch nestled on two wooded lots in Shawneeland - which has a lake, playground, beach and more! Situated on over half an acre, this property offers privacy, beautiful natural surroundings, and an abundance of flowers and mature plantings that create a peaceful setting. Inside, you'll find finished living space on both levels, offering flexibility

  Traci Shoberg Samson Properties

  224 Doe Trail, Winchester, VA 22602
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  /97

  $1,250,000 Open House 4/12

  • 4 Beds
  • 3.5 Baths
  • 4,880 Sq Ft

  199 Laurel Grove Rd, Winchester, VA 22602

  Nestled in the scenic countryside of Winchester, this impressive custom built home offers space, privacy, and beautiful Shenandoah Valley surroundings. Located in Frederick County, the property combines peaceful rural living with convenient access to shopping, dining, and commuter routes.Custom built in 2020, this spacious residence offers approximately 4,800+ square feet of living space on

  RoxAnn Grimes RE/MAX Roots

  199 Laurel Grove Rd, Winchester, VA 22602
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  /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
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  /28

  $419,000

  • 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
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  /46

  $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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  /60

  $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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  /60

  $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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