Winchester, VA Homes under $400,000

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  /42

  $344,900

  • 3 Beds
  • 1.5 Baths
  • 1,178 Sq Ft

  107 E Monmouth St, Winchester, VA 22601

  Price Reduction!! Charming Historic Home in Downtown Winchester – Move-In Ready!If you love timeless craftsmanship—think original wood floors, custom built-ins, and vintage doors—but still want the ease of modern living, this beautifully updated downtown Winchester home is calling your name!From the moment you step onto the inviting covered porch and through the front door, you’ll

  

  Jeanne Mezzatesta

  Colony Realty

  (540) 619-5037

  107 E Monmouth St, Winchester, VA 22601
• 

  Explore Winchester

• 

  

  

  /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
• 

  

  /2

  $399,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,394+ Sq Ft

  Bedford II Plan at Village at Valor Crossing - Townhomes, Winchester, VA 22601

  Covered front porch leads into the foyer. Attached 1 car garage or optional flex room or study. Open concept kitchen located next to the country kitchen and living room. Box bay rear window and 10' x 14' deck. Owner’s suite with large walk-in closet, dual vanity, and oversized seated shower in owner’s bath. Fireplace option available in select homes.

  

  DRB Homes

  Builder

  0 Tbd Weems Ln Unit 36470375, Winchester, VA 22601
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  /3

  $370,000

  • 4 Beds
  • 3 Baths
  • 1,797 Sq Ft

  807 Butler Ave, Winchester, VA 22601

  Charming 4-bedroom, 3-bath split foyer in Hampton Chase with 1,797 sq. ft. of living space. Main level offers 3 bedrooms, 2 baths, and a bright living area, while the lower level adds a 4th bedroom, full bath, and spacious family room. With a little TLC, this home could truly shine! Enjoy central air, driveway parking, and a low-maintenance yard. Conveniently located near Route 7 and I-81 for

  Israel Brooks Dream Real Estate

  807 Butler Ave, Winchester, VA 22601
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  /38

  $355,000

  • 3 Beds
  • 3 Baths
  • 2,668 Sq Ft

  109 Arrowhead Trail, Winchester, VA 22602

  Have you been waiting for the perfect home in Shawneeland? Look no further. This fantastic split-foyer has been recently renovated and is ready for you! Upgrades include a brand new asphalt shingle roof, new vinyl plank flooring throughout, fresh paint, and a total overhaul of the laundry room. The home boasts three spacious bedrooms, a large family room, an enormous basement rec room, and two

  Kristin Crosby Samson Properties

  109 Arrowhead Trail, Winchester, VA 22602
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  /33

  $379,999

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  107 Fay St, Winchester, VA 22602

  This beauty will be available mid august or earlier has exceptional renovation and superb location off Rt.11 and great proximity to I-81/Rt.37 corridor. They have done all the big ticket items like installing a new roof, upgrading the baths, BRAND NEW WINDOWS (we all love those!), and considered the most important..newly installed HVAC for keeping your home cool during the summer and warm

  Dave Spence RE/MAX Roots

  107 Fay St, Winchester, VA 22602
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  /30

  $370,000

  • 4 Beds
  • 2 Baths
  • 1,534 Sq Ft

  323 Russelcroft Rd, Winchester, VA 22601

  Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living space. Beautiful cared for by the homeowners. 3 bedrooms 2 full baths detached home .Beautiful Detached home with 3 bedrooms and 2 full baths + bonus room on the basement isfull finished with a family room. Looking for a home in amazing shape for your buyers? You've found it. 2108sf total living

  Alexandra Brown Berkshire Hathaway HomeServices PenFed Realty

  323 Russelcroft Rd, Winchester, VA 22601
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  /22

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  1399 Chestnut Grove Rd, Winchester, VA 22603

  One Level home on a private 5 acre lot. Bring your horses, goats, chickens - this is the perfect farmette! Absolutely beautiful setting that includes a paddock and a barn/shed. New roof April 2025. New Laminate flooring in kitchen. Only 10 minutes from downtown Winchester and convenient to grocery, farmers’ markets, and the hospital. House is full of character and has an open floor plan! The

  Emma Kerns MarketPlace REALTY

  1399 Chestnut Grove Rd, Winchester, VA 22603
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  /41

  $355,000

  • 3 Beds
  • 2.5 Baths
  • 1,719 Sq Ft

  415 Quail Dr, Winchester, VA 22602

  Welcome to this beautiful 4 years young, 3-bedroom, 2 1/2-bath split foyer home, perfectly nestled on a peaceful dead-end road. Set on a spacious 1/2-acre lot with serene, wooded views, this home offers the perfect blend of comfort, privacy, and modern style.Step inside to discover luxury vinyl plank flooring throughout the entire home—durable, stylish, and low-maintenance. The heart of the

  Kerry Wysong Long & Foster Real Estate, Inc.

  415 Quail Dr, Winchester, VA 22602
• 

  

  /41

  $399,900

  • 4 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  115 Etnam St, Winchester, VA 22602

  Well maintained colonial in a mature neighborhood. Take a look at the curb appeal as you pull up to the large front porch. Walk through the front door to find a generous sized dining room. The kitchen is a welcoming place to cook all of your favorite meals. There is great counterspace for easy food prep. Off the kitchen you will find 2 living spaces, great for spreading out and having your own

  Dave Spence RE/MAX Roots

  115 Etnam St, Winchester, VA 22602
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  /26

  $375,000

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

  1004 S Cameron St, Winchester, VA 22601

  PRICE REDUCED***Renovated Home in Winchester neighborhood.*** You’ll enter the house and find a spacious living room. As you continue walking, you’ll be led to the fully renovated kitchen. The kitchen features stainless steel appliances, including a new refrigerator, stove, microwave, dishwasher, new cabinets, and a granite countertop. The laundry room, located conveniently on the main level,

  Patricia Salgado Metas Realty Group, LLC

  1004 S Cameron St, Winchester, VA 22601
• 

  

  /25

  $359,900

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

  553 Highland Ave, Winchester, VA 22601

  Completely remodeled! Come enjoy ALL new everything, new electric, new windows, luxury floors, freshlypainted walls and brand-new custom kitchen and bathrooms, and all new plumbing and electricthroughout, nothing has been left untouched! New Mini Split HVAC system. Large living room opens into a gorgeous wrap aroundpeninsula kitchen with brand new Samsung appliances, granite

  Lawrence Lessin Homes By Owner, Inc.

  553 Highland Ave, Winchester, VA 22601
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  /45

  $399,900

  • 4 Beds
  • 1.5 Baths
  • 2,860 Sq Ft

  684 Berryville Ave, Winchester, VA 22601

  Come check out this 4-bedroom 1.5 bath 4 level Brick Colonial with a Detached Garage all on a double lot, updated roof, windows, new plumbing & water heater, updated electric & panel box. There is plenty of room to grow and put your flavor in the walk-up attic and basement. Home has the original Hardwood floors & Beautiful Woodworking that has never been painted on the main level. Large, Covered

  Richard Kozlowski Long & Foster Real Estate, Inc.

  684 Berryville Ave, Winchester, VA 22601
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  /18

  $355,000

  • 3 Beds
  • 1 Bath
  • 936 Sq Ft

  2940 Grace St, Winchester, VA 22601

  Welcome to your charming Cape Cod retreat! Built in 1955, this delightful 3-bedroom, 1-bath home offers a warm and inviting atmosphere—perfect for anyone looking for a cozy and welcoming place to call home. --- Step inside to a thoughtfully designed layout that makes the most of the 936 square feet of finished living space. --- Home is equipped with energy-efficient solar panels to help reduce

  Lauren Smith-Washbourne Coldwell Banker Premier

  2940 Grace St, Winchester, VA 22601
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  /27

  $369,990 New Construction

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

  104 Pomo Ln, Winchester, VA 22602

  Discover the Delmar by D.R. Horton—a thoughtfully designed interior townhome that combines comfort, style, and convenience. With 1,500 square feet of living space, this two-story home features 3 bedrooms, 2.5 bathrooms, and a 1-car garage, perfectly suited for low-maintenance living without sacrificing space. The main level offers an open-concept layout where the modern kitchen seamlessly

  

  D.R. Horton

  Builder

  104 Pomo Ln, Winchester, VA 22602
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  /27

  $369,990 New Construction

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

  102 Pomo Ln, Winchester, VA 22602

  Introducing the Delmar by D.R. Horton—a spacious and stylish interior townhome designed for easy, low-maintenance living. This two-story home offers 1,500 square feet of well-planned space with 3 bedrooms, 2.5 bathrooms, and a 1-car garage. The open-concept main level features a modern kitchen with a large island, plenty of cabinet space, and an oversized pantry—all flowing seamlessly into the

  

  D.R. Horton

  Builder

  102 Pomo Ln, Winchester, VA 22602
• 

  

  /27

  $369,990 New Construction

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

  106 Pomo Ln, Winchester, VA 22602

  Welcome to the Delmar by D.R. Horton—a beautifully crafted interior townhome offering the low-maintenance lifestyle you want with the space you need. This two-story home features 3 bedrooms, 2.5 bathrooms, a 1-car garage, and 1,500 square feet of smartly designed living space. Step inside to an open main level where the stylish kitchen flows effortlessly into the dining and living areas. You’ll

  

  D.R. Horton

  Builder

  106 Pomo Ln, Winchester, VA 22602
• 

  

  /3

  $369,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  207 Otter Trail, Winchester, VA 22602

  This beautifully designed 3-bedroom, 2-bathroom home offers the perfect combination of modern comfort, single-level living, and thoughtful details—ideal for both growing families and retirees looking to downsize without compromise. With 1,560 sq. ft. of well-planned space, this home delivers everything you need in a manageable, low-maintenance package.As you step through the front door,

  Babak Taghavi Venture Realty

  207 Otter Trail, Winchester, VA 22602
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  /28

  $374,990 New Construction

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

  0 Heirloom Way Unit VAFV2021776, Winchester, VA 22603

  Build this Brand New Northgate villa in Brookfield Residential's newest Active Adult community, Hiatt Pointe at Snowden Bridge, a gated community for those persons 55 or better for 2025 move in!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

  Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

  0 Heirloom Way Unit VAFV2021776, Winchester, VA 22603
• 

  

  /19

  $359,900 New Construction

  • 3 Beds
  • 3 Baths
  • 1,850 Sq Ft

  1619 Tomahawk Trail, Winchester, VA 22602

  Brand New! Done! Top of the world views! Private. Over 1/2 acre lot private, stunning views of valley and mountains. Side load garage with garage windows across front. 3 bed, 3 full baths, 2 car garage, open floor plan, family rm and kitchen with vault. HW floors entire main floor and stairs, tile floors in all baths, upgraded cabinets. BUILDER BONUS HARDWOOD IN BEDROOMS, BUILDER BONUS

  Jim Thomson Realty ONE Group Old Towne

  1619 Tomahawk Trail, Winchester, VA 22602
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  /2

  $369,900 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  301 Liberty Ave, Winchester, VA 22601

  Welcome to this charming all - brick colonial residence situated in the heart of downtown Winchester. Just blocks away from the scenic walking mall you’ll discover an array of quaint shops, restaurants and the renowned Apple Blossom Parade route. This meticulously fully remodeled home boasts three spacious bedrooms and two luxurious bathrooms and is ready for a new family to create memories in.

  John Ashton Equity Realty

  301 Liberty Ave, Winchester, VA 22601
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  /45

  $365,000

  • Land
  • 15 Acres
  • $24,333 per Acre

  000 Light Rd, Winchester, VA 22603

  Gentle stretches of open meadow roll into quiet, wooded groves where sunlight filters through the trees. Hidden among them, peaceful little ponds shimmer like jewels, inviting you to pause and simply breathe. Imagine mornings filled with birdsong, afternoons exploring your own private trails, and evenings watching the sky glow across wide open fields. Whether you long to build a cozy retreat, a

  Melissa Johnston ERA Oakcrest Realty, Inc.

  000 Light Rd, Winchester, VA 22603
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  /2

  $325,000

  • 4 Beds
  • 1.5 Baths
  • 1,199 Sq Ft

  118 E Monmouth St, Winchester, VA 22601

  Charming Remodeled Colonial in Historic Old Town WinchesterYou’ll fall in love with this beautifully updated Colonial located in the heart of Winchester’s Historic District. Just steps from the Downtown Pedestrian Mall, Handley High School, and local shops and restaurants, this home blends timeless character with modern convenience.• 4 Bedrooms 1.5 Bathrooms• Restored original

  Scott Dawson Oakcrest Commercial LLC.

  118 E Monmouth St, Winchester, VA 22601
• 

  

  /39

  $324,900

  • 4 Beds
  • 3 Baths
  • 2,369 Sq Ft

  102 Elk Trail, Winchester, VA 22602

  Split Foyer with plenty of space and a heck of a view in the private community of Wilde Acres. From your breakfast room you will pan out to see the Shenandoah valley and your private backyard is set with a wooded backdrop. this 4 bedroom abode adopts the sense of open space along with traditional bedroom layout on the main floor with your entertaining room both off the kitchen and in the

  Dave Spence RE/MAX Roots

  102 Elk Trail, Winchester, VA 22602
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  /41

  $349,900

  • 3 Beds
  • 1 Bath
  • 1,192 Sq Ft

  316 Virginia Ave, Winchester, VA 22601

  Well maintained Colonial offering timeless character and modern potential in the heart of Winchester. This 3-bedroom, 1 1/2 bath home features beautiful hardwood floors, a spacious living area, formal dining room, and a well-sized kitchen with ample pantry storage. Finished basement with lots of space and also huge attic space with room for storage or play room. 15 Year old roof, new

  Berta Vasquez Samson Properties

  316 Virginia Ave, Winchester, VA 22601
• 

  

  /25

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,710 Sq Ft

  428 Imperial St, Winchester, VA 22601

  Enjoy the ease of one-level living in the heart of Winchester City thats ready for your personal touches! Ideally located just minutes from shopping, dining, and local conveniences, this charming all-brick rancher with a full walk-up basement offers both comfort and functionality. The kitchen features space for a dining table, while the inviting living room boasts a cozy fireplace with a lovely

  Leah Clowser RE/MAX Roots

  428 Imperial St, Winchester, VA 22601
• 

  

  /35

  $349,990

  • 3 Beds
  • 2 Baths
  • 2,302 Sq Ft

  1005 Pennsylvania Ave, Winchester, VA 22601

  A classic brick ranch in Winchester, VA, has three bedrooms and two full bathrooms. The basement includes a separate entrance, a laundry area, a full bathroom, and an additional bonus room. Recent updates include: finished basement, new HVAC system, complete renovations of both bathrooms, new hardwood flooring, and an updated kitchen with new cabinets and countertops. No HOA restrictions.

  Nathalie Acosta Spring Hill Real Estate, LLC.

  1005 Pennsylvania Ave, Winchester, VA 22601
• 

  

  /50

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  416 Bluebird Trail, Winchester, VA 22602

  Just Listed – Beautifully Remodeled 3 Bedroom, 2 Bath Rambler! Step into comfort and style with this newly remodeled rambler featuring 3 spacious bedrooms and 2 modern bathrooms. Every inch of this home has been updated – including brand-new appliances, luxury flooring throughout, and fresh finishes that make it move-in ready. Enjoy peaceful wooded views from your private back deck, perfect for

  Lisa Blansett Mountains Edge Realty LLC

  416 Bluebird Trail, Winchester, VA 22602
• 

  

  /63

  $323,000

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft

  151 Mccormick Cir Unit 203, Winchester, VA 22602

  55+ Condo Community, this charming 2-bedroom, 2-bathroom unit offers a perfect blend of comfort and style, featuring a Craftsman architectural design that welcomes you home. Step inside to find a thoughtfully designed interior with a combination kitchen and dining area, ideal for entertaining or enjoying quiet meals. The spacious family room off the kitchen is perfect for relaxation, while the

  Wanda Garris Miller Century 21 Redwood Realty

  151 Mccormick Cir Unit 203, Winchester, VA 22602
• 

  

  /13

  $349,999

  • 5 Beds
  • 2 Baths
  • 1,584 Sq Ft

  505 Green St, Winchester, VA 22601

  Charming 3-Level Split Home in the Heart of Winchester!This split level home could be your forever home! Surrounded by parks, top-rated schools, and everyday amenities. Quick access to Route 7 and Interstate 81 commuting is breeze! Upstairs, you’ll find three generously sized bedrooms and a full bathroom, offering a peaceful seperate area. The main level boasts a warm and

  Julissa Rodriguez Vaze Realty

  505 Green St, Winchester, VA 22601
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  /34

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  216 Monticello Square, Winchester, VA 22602

  Seller is offering $5,000 toward purchasers closing cost with acceptable offer! Step into this beautifully designed 3-level townhome that offers both space and sophistication. With 3 bedrooms, 2.5 baths, and a 1-car garage, this home balances comfort and functionality perfectly. Interior Highlights:An upgraded kitchen featuring modern appliances, stylish cabinetry, and ample counter

  LESLIE WEBB Long & Foster Real Estate, Inc.

  216 Monticello Square, Winchester, VA 22602
• 

  

  /19

  $308,000

  • 2 Beds
  • 1 Bath
  • 1,027 Sq Ft

  104 Redwood Ln, Winchester, VA 22603

  Charming 2bedroom 1bath house located minutes from downtown Winchester in Frederick County. House features a large kitchen, mudroom, attic, basement and large fenced in back yard. This house has the potential to become a four bedroom as the current owner has started framing in the upstairs for two additional bedrooms along with electrical hookup. Water heater is 2 years old and HVAC system is

  Courtney Spaid Crum Realty, Inc.

  104 Redwood Ln, Winchester, VA 22603
• 

  

  /22

  $334,900

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft

  140 Mccormick Cir Unit 403, Winchester, VA 22602

  Nearly-new 55+ condominium located in Winchester Landing, offering comfort, convenience, and style just minutes from town. Step inside to an open floor plan filled with natural light, featuring a bright and modern kitchen with quartz countertops, a center island with sink, and sleek lighting that makes entertaining a breeze.The oversized primary suite is a true retreat, complete with a

  Sharon Farinholt Realty ONE Group Old Towne

  140 Mccormick Cir Unit 403, Winchester, VA 22602
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  /28

  $339,900

  • 3 Beds
  • 1 Bath
  • 1,376 Sq Ft

  230 Allison Ave, Winchester, VA 22601

  Welcome to 230 Allison Avenue, a recently renovated 3-bedroom, 1-bath home on a spacious 0.23-acre lot in Winchester. Ideally located just 1 mile from Winchester Medical Center and only minutes to Walmart Supercenter, shops, restaurants, and vibrant downtown Winchester, this home offers both convenience and charm. Step inside to discover a thoughtfully updated interior featuring luxury vinyl

  Jon Fleming Weichert Realtors - Blue Ribbon

  230 Allison Ave, Winchester, VA 22601
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  /52

  $300,000

  • 2 Beds
  • 4 Baths
  • 2,438 Sq Ft

  102 Duwamish Trail, Winchester, VA 22602

  If you are looking for a home with privacy and a peaceful rural feel but only 15 minutes to Winchester then this home is for you! Set in a natural habitat, 102 Duwamish Trail has a vintage feel and could be a weekend getaway or your primary residence away from the city. No HOA! There is an open feel to the main level which has a versatile floor plan. There is a sunroom, a family room & a

  Dorothy Beach Samson Properties

  102 Duwamish Trail, Winchester, VA 22602
• 

  

  /27

  $339,000

  • 4 Beds
  • 3 Baths
  • 2,056 Sq Ft

  425 Beechcroft Rd, Winchester, VA 22601

  Open House Saturday 16th only. 1-3. One level living in a sturdy, large (over 2000+/- SF) brick rancher close to all amenities? Restaurants and stores all within a couple of miles including Jim Barnett Park. Easy access to major commuter routes. Relax on the huge front porch or rear covered patio in the private, fully fenced backyard. Semi-open floor plan in the main area bracket the kitchen

  Laurel Murray Samson Properties

  425 Beechcroft Rd, Winchester, VA 22601
• 

  

  /22

  $317,500

  • 3 Beds
  • 1.5 Baths
  • 1,634 Sq Ft

  102 Zephyr Ln, Winchester, VA 22602

  Motivated Sellers! Carpet allowance and Professional Cleaning will be provided prior to closing. Don’t miss this opportunity for a Beautifully Updated 3-Bedroom Town home in Prime Location!Welcome to this charming 3-bedroom, 1.5-bath town home located in a highly sought-after neighborhood. Featuring a cozy fireplace in the living room and a stylishly remodeled kitchen with modern finishes,

  Kandi McKenzie Realty ONE Group Old Towne

  102 Zephyr Ln, Winchester, VA 22602
• 

  

  /50

  $345,000

  • Land
  • 40 Acres
  • $8,582 per Acre

  0 Easter Ridge Lot 8 Ln, Winchester, VA 22603

  Own a piece of the beautiful Siler Heights community in Cross Junction. Located just minutes northwest of Winchester near Lake Holiday. Access is secured via extensive road frontage on Easter Ridge Lane. Features a fully functional hunting cabin with a wood stove and propane used for heating and cooking. The cabin has an open layout and separate sleeping quarters via a loft. Experience exciting

  Chad Pangle Whitetail Properties Real Estate, LLC

  0 Easter Ridge Lot 8 Ln, Winchester, VA 22603
• 

  

  /30

  $314,900

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft

  140 Mccormick Cir Unit 302, Winchester, VA 22602

  Welcome home to this gorgeous, like-new condo! This stunning unit was constructed last year and offers the perfect blend of modern elegance and comfort. Enjoy top-tier finishes like quartz countertops, stainless steel appliances, and beautiful LVP flooring throughout.Relax and unwind in the meticulously manicured common grounds, take a stroll on the walking path, or enjoy the convenience of

  Karl Achstetter Keller Williams Realty

  140 Mccormick Cir Unit 302, Winchester, VA 22602
• 

  

  /37

  $389,000

  • 3 Beds
  • 1.5 Baths
  • 1,416 Sq Ft

  31 W Whitlock Ave, Winchester, VA 22601

  Charming Home Near Handley High School – Move-In Ready!Welcome to this beautifully updated home in a fantastic downtown location—just a short walk to shops, restaurants, and all that the vibrant city center has to offer. This property features a converted garage that now serves as a versatile studio space, perfect for a home office, art studio, or guest suite.Enjoy a spacious,

  Meridee Powars Link Realty Services LLC

  31 W Whitlock Ave, Winchester, VA 22601

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