Winchester, VA Homes for Sale under $500,000

• 

  

  

  /49

  $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
• Explore Winchester

• 

  

  

  /52

  $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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  /37

  $423,900

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft

  1033 Sunnyside Dr, Winchester, VA 22603

  Welcome to 1033 Sunnyside Drive, a beautifully renovated bungalow tucked away on a quiet street just minutes from historic downtown Winchester. This charming home blends classic character with modern upgrades, creating a warm and inviting place to call home.Start your day on the inviting 9’ x 11’ tiled front porch, complete with new railings and stairs, the perfect spot for morning coffee or

  Tien Dao Redfin Corporation

  1033 Sunnyside Dr, Winchester, VA 22603
• 

  

  

  /23

  $459,990 New Construction

  • 2 - 3 Beds
  • 1 Bath
  • 1,564+ Sq Ft

  Hemingway Plan at Hiatt Pointe at Snowden Bridge - 55+ Garden Homes Collection, Winchester, VA 22603

  Welcome to your ideal one-level villa- the Hemingway! This thoughtfully designed home centers around a spacious kitchen, perfect for both daily life and entertaining guests. The main level offers two generous bedrooms, including a primary suite featuring a large walk-in closet and a private en suite bathroom for ultimate comfort. Convenience is key with a laundry room located just off the 2-car

  Brookfield Residential Builder

  105 Wagtail Ln Unit 36578850, Winchester, VA 22603
• 

  

  

  /57

  $465,525

  • Land
  • 64.21 Acres
  • $7,250 per Acre

  0 Trojan Ln Unit LotWP001, Winchester, VA 22603

  This pristine piece of land is located just minutes north of Winchester in the Green Spring area of the county. The entrance is gated, and access to this parcel is secured via a 20 ft-wide deeded right-of-way off Cattail Road named Trojan Lane. An additional 60 ft-wide deeded right-of-way off Cattail Road is also included. Discover potential building sites throughout this tract as you navigate

  Chad Pangle Whitetail Properties Real Estate

  0 Trojan Ln Unit LotWP001, Winchester, VA 22603
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  /49

  $422,999

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  709 Dicks Hollow Rd, Winchester, VA 22603

  Welcome to this private gem nestled on a corner lot in beautiful Winchester, VA! This stunning 3-bedroom, 2-bath home offers the perfect balance of modern upgrades, comfort, and peace of mind. Step inside to find a fully remodeled primary bathroom featuring a luxurious walk-in shower — a spa-like retreat in the comfort of your own home. Enjoy the confidence of a brand-new roof with a 30-year

  Fehiber Rosario NBI Realty, LLC

  709 Dicks Hollow Rd, Winchester, VA 22603
• 

  

  /37

  $430,000

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

  17 E Leicester St, Winchester, VA 22601

  LOWER INTEREST RATE FOR YOU.....Sellers are offering you 2 percent of sales price so you can buy down your interest rate with an initial 2/1 interest rate buydown OR use the 2% seller concession for your closing costs on this classic brick “American Foursquare” house in Winchester’s historic district. This very well maintained 1928 home was designed and built by “ole time” craftsmen who had an

  Roger Lamborne MarketPlace REALTY

  17 E Leicester St, Winchester, VA 22601
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  /56

  $439,000

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

  743 Berryville Ave, Winchester, VA 22601

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

  Sineenat Sirimas Pearson Smith Realty, LLC

  743 Berryville Ave, Winchester, VA 22601
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  /74

  $450,000

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

  320 Shawnee Trail, Winchester, VA 22602

  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 under the stars. The private pool area offers

  Stacey Mullins ERA Oakcrest Realty, Inc.

  320 Shawnee Trail, Winchester, VA 22602
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  /44

  $424,500

  • 4 Beds
  • 2.5 Baths
  • 1,805 Sq Ft

  21 W Pall Mall St, Winchester, VA 22601

  Timeless soul with modern spirit. Step into a piece of Winchester history, reimagined for the way you live today. From the iconic front porch—perfect for your morning coffee or evening wind-down—to the private, fenced-in backyard, this home is designed for seamless indoor-outdoor living. Renovated top to bottom with classic features such as crown moulding, thick wood banisters, and columns

  Allyson Lenz Compass

  21 W Pall Mall St, Winchester, VA 22601
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  /32

  $467,590 New Construction

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  125 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. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen, ideal for

  Brooks Sears D R Horton Realty of Virginia LLC

  125 Trellis View Ln, Winchester, VA 22602
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  /46

  $449,000

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

  25 W Southwerk St, Winchester, VA 22601

  **OPEN HOUSE THIS SUNDAY, MARCH 29th, FROM 11-1pm!!**Welcome to this beautifully updated gem in the heart of Winchester! From the moment you arrive, the expansive front porch invites you to sit back and enjoy the charm of one of the city's most sought-after locations. Situated just moments from Handley High School, vibrant downtown shops, local restaurants, and scenic parks, this home offers

  Dan Whitacre Colony Realty

  25 W Southwerk St, Winchester, VA 22601
• 

  

  /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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  /43

  $414,900 New Construction

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

  713 Ross St, Winchester, VA 22601

  NEW AND READY TO MOVE IN!!!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
• 

  

  /23

  $449,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  124 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. The moment you step inside the home; you will be greeted by an inviting foyer leading you into the heart of the home. The dining room seamlessly connects with the living room and kitchen, ideal for

  D.R. Horton Builder

  124 Trellis View Ln, Winchester, VA 22602
• 

  

  /22

  $469,990 New Construction

  • 2 - 3 Beds
  • 1 Bath
  • 1,670+ Sq Ft

  Fitzgerald Plan at Hiatt Pointe at Snowden Bridge - 55+ Garden Homes Collection, Winchester, VA 22603

  Welcome to your dream one-level villa, the Fitzgerald! This beautifully designed home features a central kitchen that serves as the heart of the house, perfect for both everyday living and entertaining. The main level includes two spacious bedrooms, including a luxurious primary suite with an expansive walk-in closet and an en suite bathroom for your comfort and privacy. Additionally, you'll find

  Brookfield Residential Builder

  105 Wagtail Ln Unit 36578849, Winchester, VA 22603
• 

  

  /57

  $465,525

  • Land
  • 64.21 Acres
  • $7,250 per Acre

  0 Trojan Ln, Winchester, VA 22603

  This pristine piece of land is located just minutes north of Winchester in the Green Spring area of the county. The entrance is gated and access into this parcel is secured via a 20 ft wide deeded right of way off of Cattail Road named Trojan Lane. An additional 60 ft wide deeded right of way off of Cattail Road is also included. Discover potential building sites throughout this tract as you

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Trojan Ln, Winchester, VA 22603
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  /7

  $499,000

  • Land
  • 17.98 Acres
  • $27,753 per Acre

  Lot 13 Tavistock Dr, Winchester, VA 22602

  Beautiful 17.98 acre Lot, approved for 3 bedroom perk, Tavistock Estates, one of the last lots remaining! A gorgeous 7 minute drive from town through farmland and full of mountain views. Excellent neighborhood, road access is great, level lot among 'horse country' estates! Build your dream mini equestrian farm or just enjoy peace, quiet, and serenity with the genius of a quick commute into town!

  Gillian Greenfield Coldwell Banker Premier

  Lot 13 Tavistock Dr, Winchester, VA 22602
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  /31

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,158 Sq Ft

  112 Grindstone Dr, Winchester, VA 22602

  Beautifully maintained 4-bedroom, 2.5-bath colonial home in the desirable Red Fox Run community. Built in 2002 and situated on a spacious 0.29-acre lot, this property offers the perfect blend of comfort, space, and offers tons of potential! The main level flows effortlessly, including both formal dining & living, with a bright eat-in style kitchen that opens to a large deck—ideal for

  Lisa Behr Hunt Country Sotheby's International Realty

  112 Grindstone Dr, Winchester, VA 22602
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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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  /10

  $449,000

  • Land
  • 0.09 Acre
  • $4,988,889 per Acre

  1 N Braddock St, Winchester, VA 22601

  Make Offer! Excellent Development Opportunity! Downtown Winchester, VA! APPROVED (!) Mixed Use site plan for multi-story building consisting of 1st floor commercial space (1,340 SF) with 6x spacious luxury condos/apartments (potential for seven) with rooftop patio above (for total of 8 rental units)! Legacy development opportunity! One North is located in the second historical district and

  Gillian Greenfield Coldwell Banker Premier

  1 N Braddock St, Winchester, VA 22601
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  /45

  $465,000

  • 3 Beds
  • 2.5 Baths
  • 2,293 Sq Ft

  3137 Eton Place, Winchester, VA 22601

  Welcome to The Lofts at Creekside! Better than new and absolutely breathtaking, this four-level interior townhome delivers style, space, and an unbeatable lifestyle—all within walking distance to top-rated restaurants, shopping, and the historic Kernstown Battlefield. Offering 3 bedrooms and 2.5 baths, the home features a chic upper-level loft that opens to a stunning private terrace, perfect for

  Laura White ERA Oakcrest Realty, Inc.

  3137 Eton Place, Winchester, VA 22601
• 

  

  /20

  $449,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,657+ Sq Ft

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

  The Cabral, a 1,657 square foot two-story home, offers an open-concept design perfect for modern living. Featuring three bedrooms, two and a half bathrooms, a versatile loft, and a two-car garage, this home is ideal for families seeking both space and functionality. Upon entering through the front porch, you'll find a convenient first-floor powder room and coat closet in the foyer. The spacious

  D.R. Horton Builder

  137 Seminole Dr Unit 36203778, Winchester, VA 22602
• 

  

  /28

  $485,990 New Construction

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

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

  The Pine is a 1,953 square foot open concept home, offering four bedrooms, two and a half bathrooms and a two-car garage. A foyer with a powder room and coat closet greets you as you enter this home. The open floorplan allows you and your loved ones to spend quality time together while in the living room, casual dining area and kitchen. The spacious kitchen has a large island with room for

  D.R. Horton Builder

  137 Seminole Dr Unit 36203779, Winchester, VA 22602
• 

  

  /17

  $449,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,657 Sq Ft

  136 Wappinger Terrace, Winchester, VA 22602

  Step into 1,657 square feet of well-designed living space in the Cabral, featuring 3 spacious bedrooms, 2.5 bathrooms, and a flexible loft upstairs—perfect for a home office, playroom, or additional lounge area. This home showcases a charming white siding exterior with stone accents, while the interior boasts sleek white kitchen and bathroom cabinets paired with modern finishes throughout. Enjoy

  D.R. Horton Builder

  136 Wappinger Terrace, Winchester, VA 22602
• 

  

  /54

  $449,990

  • 3 Beds
  • 3.5 Baths
  • 2,239 Sq Ft

  142 Sequoia Dr, Winchester, VA 22602

  Some homes check the boxes. Others quietly stand apart the moment you pull up. This one does that. Not because it tries to impress, but because the setting, the layout, and the way the house sits on the land just make sense. Start with the lot. It’s a premium double-sized end-unit lot, something you simply don’t see often in townhouse communities. The home sits at the edge of the

  Alexander Bracke Real Broker, LLC

  142 Sequoia Dr, Winchester, VA 22602
• 

  

  /17

  $435,000

  • 5 Beds
  • 4 Baths
  • 2,014 Sq Ft

  122 Cherry Hill Cir, Winchester, VA 22602

  Nestled in the charming Green Acres subdivision, this delightful split-level home offers a perfect blend of comfort and functionality. With five spacious bedrooms and four full bathrooms, there's ample room for everyone to unwind and thrive. The heart of the home features a cozy fireplace, inviting you to gather with loved ones during chilly evenings. The fully finished basement, complete with

  Jen Moore ERA Oakcrest Realty, Inc.

  122 Cherry Hill Cir, Winchester, VA 22602
• 

  

  /40

  $414,900 New Construction

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

  709 Ross St, Winchester, VA 22601

  NEW AND READY TO MOVE IN!!!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

  709 Ross St, Winchester, VA 22601
• 

  

  /28

  $415,000

  • 3 Beds
  • 1 Bath
  • 2,683 Sq Ft

  307 Fox Run Ln, Winchester, VA 22602

  Wake up to breathtaking views of the Shenandoah Valley every day in this peaceful, beautifully renovated cottage. Completely updated in 2024, the home blends modern amenities with warm, inviting charm.The bright, open living space features a vaulted ceiling and abundant natural light, creating an airy, welcoming atmosphere. The living room showcases large windows, custom built-ins, and a

  Karen Sparks Corcoran McEnearney

  307 Fox Run Ln, Winchester, VA 22602
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  /51

  $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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  /27

  $449,990 New Construction

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

  FREEPORT DUPLEX Plan at Willow Run - Duplexes, Winchester, VA 22601

  Looking for a beautiful home that meets all your needs? Look no further than the Freeport! This stunning 1,492 square foot residence features three bedrooms, two baths, and a convenient two-car garage, all designed with your active adult lifestyle in mind. As you step into the foyer, you are greeted by the open-concept kitchen and living area with plenty of space for cooking, dining, and

  D.R. Horton Builder

  105 Trellis View Ln Unit 36406838, Winchester, VA 22601
• 

  

  /20

  $474,990 New Construction

  • 2 Beds
  • 1 Bath
  • 1,564 Sq Ft

  110 Carnation Way, Winchester, VA 22603

  Welcome to your ideal one-level villa- the Hemingway! This thoughtfully designed home centers around a spacious kitchen, perfect for both daily life and entertaining guests. The main level offers two generous bedrooms, including a primary suite featuring a large walk-in closet and a private en suite bathroom for ultimate comfort. Convenience is key with a laundry room located just off the 2-car

  Brookfield Residential Builder

  110 Carnation Way, Winchester, VA 22603
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  /38

  $449,990 New Construction

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

  1819 Reese Ct, Winchester, VA 22601

  1819 Reese Court is a move-in ready 3-level townhome with full brick front in Winchester, VA. Our modern Adams floorplan features a 1-car garage, and along with a bedroom and full bathroom on the first floor. Stained oak stairs lead you to the main level with LVP flooring. The kitchen is equipped with beautiful quartz countertops, sasparilla cabinets, and stainless-steel appliances. The upper

  D.R. Horton Builder

  1819 Reese Ct, Winchester, VA 22601
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  /57

  $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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  /61

  $459,000 Open Sat 1PM - 3PM

  • 6 Beds
  • 3 Baths
  • 1,552 Sq Ft

  2250 Roosevelt Blvd, Winchester, VA 22601

  Charming Cape Cod nestled in a quiet residential neighborhood, just minutes from Route 11 and I-81 for easy commuting. This light-filled home welcomes you with a bright living room featuring a stunning stone fireplace as its centerpiece. The cabinet-packed kitchen is the heart of the home and offers granite countertops and a bar-height peninsula that opens seamlessly to the living room . The main

  Heloisa Amar Samson Properties

  2250 Roosevelt Blvd, Winchester, VA 22601
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  /34

  $429,000

  • 4 Beds
  • 3 Baths
  • 1,783 Sq Ft

  570 Welltown Rd, Winchester, VA 22603

  Built to last but updated and move in ready! This charming brick home has a lot to offer. The location is perfect with quick access to I-81 for commuting, is only minutes away from restaurants, shopping and other amenities, and maybe best of all, it has a separate in-law suite on the lower level (tenant is currently on a month to month lease and is happy to stay if new owner allows)! The basement

  Marielle Thoburn Keller Williams Realty

  570 Welltown Rd, Winchester, VA 22603
• 

  

  /81

  $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
• 

  

  /43

  $444,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,195 Sq Ft

  117 Wagtail Ln, Winchester, VA 22603

  Welcome to 117 Wagtail Lane, a brand-new Van Metre townhome located in the sought-after 55+ community of Hiatt Point at Snowden Bridge. Designed for low-maintenance living, this thoughtfully crafted home features an open-concept main level filled with natural light and a modern kitchen with stylish finishes—ideal for everyday living and entertaining. The spacious primary suite is located on the

  Lindsay Potter Real Broker, LLC

  117 Wagtail Ln, Winchester, VA 22603
• 

  

  /52

  $434,999

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  1105 Henry Dr, Winchester, VA 22602

  Home offers nearly 3000 sqft of finished living space that has Luxury Vinyl flooring through out both levels (absolutely no carpet) that features 4 bedrooms and 2.5 baths situated on over a 1/2 acre (.61) of ground. Upon entering you will find an open floor plan that encompasses a large living room and dining room with canned lighting then pours into the large eat in kitchen (new appliances) that

  James Amick RE/MAX Roots

  1105 Henry Dr, Winchester, VA 22602
• 

  

  /50

  $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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