Refine Search
Sort by
Homesite 3 Monteith Dr, Winchester
$376,990
3 Beds ⋅ 4 Baths
***OFFERING UP TO $15,000 IN CLOSING COST ASSISTANCE FOR PRIMARY RESIDENCE WITH USE OF APPROVED LENDER AND TITLE!** SPECIAL INTEREST RATES AVAILABLE** CONTACT SALES CONSULTANT FOR DETAILS* The most affordable townhomes in Winchester City! Luxury 3-level, 3-bedroom townhome with 1-car garage located in the heart of Winchester! Home backing to trees for added privacy and peaceful views. Possibility of 4th bedroom or flex space in the finished lower level with private full bath and walk-in shower; ideal for guests, home office, or recreation room. This beautifully upgraded home features an open-concept layout with spacious living areas and a stunning kitchen complete with oversized island seating for four; perfect for entertaining and everyday living. The third level offers conveniently located laundry near the bedrooms for added convenience. Enjoy outdoor living on the 10x16 maintenance-free deck overlooking mature trees. Attached 1-car garage provides additional storage and convenience. New luxury townhomes in Winchester are selling quickly; schedule your tour today before this opportunity is gone! *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

Homesite 3 Monteith Dr, Winchester

Listing courtesy of DRB Group Realty, LLC. Contact:

448 Canyon Rd, Winchester
$529,900
4 Beds ⋅ 4 Baths
Nestled in the charming Sovereign Village, this stunning Colonial home offers a perfect blend of comfort and style. Built in 2009, this spacious residence boasts 2,452 square feet of thoughtfully designed living space, featuring four generous bedrooms and three and a half bathrooms, ensuring ample room for relaxation and privacy. As you step inside, you'll be greeted by an inviting atmosphere that encourages gatherings and cherished moments. The well-appointed kitchen is ready for your culinary adventures, while the cozy living spaces provide the perfect backdrop for creating lasting memories. Outside, the 0.28-acre lot offers a delightful retreat, complete with access to a community pool for those warm summer days. The attached front-entry garage provides convenience and additional storage, making everyday life a breeze. With its prime location in a vibrant community, this home is not just a place to live, but a place to thrive. Enjoy the tranquility of suburban living while being just a short drive from local amenities and recreational opportunities. This is more than just a house; it's a place where you can truly feel at home. Don't miss the chance to make this beautiful property your own!

448 Canyon Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

337 George St, Winchester
$429,900
5 Beds ⋅ 2 Baths
Fantastic location, classic brick charm, and plenty of space! This well-located brick rambler offers easy access to Route 50, Route 37, and I-81, while being just minutes from Valley Health. A long driveway, carport, concrete patio, and large, level backyard provide plenty of outdoor space and convenience. Inside, you’re welcomed by a light and bright living room featuring beautiful hardwood floors and a cozy fireplace. The kitchen opens directly to the dining room, creating a functional layout for everyday living and entertaining. The fully finished basement adds even more versatility, featuring two bedrooms, a spacious den with a second fireplace, and a kitchenette. Whether used for guests, extended living space, a home office, or recreation, the lower level offers plenty of possibilities. With a convenient location, generous yard, multiple living spaces, and a flexible finished basement, this home is ready to make your own!

337 George St, Winchester

Listing courtesy of Samson Properties. Contact:

1400 Gordon Pl, Winchester
$670,000
3 Beds ⋅ 2 Baths
ONE LEVEL LIVING AND BRAND NEW ROOF in The Downs at Meadowbranch, a sought after community convenient to shopping, medical center, and Old Town Winchester. OPEN SATURDAY 10/10 FROM 1-3PM! Expansive all-brick home offers 3 bedrooms, 2 bathrooms, attached 2-car garage and 2450 square feet of living space! What's better than an idyllic 1/5 acre corner lot... how about an idyllic 1/5 acre corner lot you don't have to mow? HOA fees include lawn mowing, mulching, leaf clean up, and tree and shrub maintenance! Hardwood floors run through the living and dining rooms, kitchen, and the 2nd and 3rd bedrooms. Charming country kitchen features granite counters and stainless steel appliances, as well as a cozy breakfast nook, and access to the screened porch with ceiling fan. Large living room with gas fireplace. Formal dining room boasts chair and crown molding. Primary bedroom has walk in closet and en-suite bath with double vanity, jetted tub and separate shower. Bathrooms and bedrooms have been FRESHLY PAINTED. This is a great opportunity to own in a desirable rarely-available City of Winchester community! Schedule your tour today!

1400 Gordon Pl, Winchester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

138 Copeley Cir, Winchester
$419,900
3 Beds ⋅ 4 Baths
Welcome to 138 Copeley Circle! This beautifully maintained 3-bedroom, 3.5-bath home offers spacious, comfortable living with a thoughtfully designed floor plan and plenty of room to entertain. The main level features an inviting living area, a well-appointed kitchen with ample cabinetry and counter space, and a dining area that opens to an extended deck, creating the perfect space for outdoor dining, relaxing, and entertaining. Upstairs, you’ll find generously sized bedrooms, including a comfortable primary suite, while the additional finished living space provides flexibility for a home office, recreation area, or guest space. With 3 full bedrooms, 3.5 bathrooms, an attached 1-car garage, and an extended deck, this home combines functionality with low-maintenance living. Conveniently located in the Winchester area, 138 Copley Circle is close to shopping, dining, schools, commuter routes, and the many amenities Winchester has to offer. Whether you're a first-time buyer, growing household, or looking for a move-in-ready investment, this home is ready to welcome its next owner.

138 Copeley Cir, Winchester

Listing courtesy of Realty FC. Contact:

1 E Hart St, Winchester
$299,900
4 Beds ⋅ 3 Baths
Enjoy downtown Winchester living with plenty of flexibility! This 4-bedroom, 2.5-bath townhome offers a functional layout in a convenient location close to restaurants, shopping, schools, Handley games, and all that downtown Winchester has to offer. The main level features a comfortable living area, kitchen with eat-in space, and access to a beautiful Trex deck overlooking the fully fenced backyard. Upstairs, you'll find three bedrooms and a full bath. The finished walk-out lower level adds even more versatility with a fourth bedroom, full bath, and laundry area. Step outside to a stamped concrete patio and fenced yard with storage shed. With multiple outdoor living spaces, off-street parking, and an incredibly convenient location, this home offers plenty of possibilities inside and out.

1 E Hart St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

5 E Hart St, Winchester
$284,900
2 Beds ⋅ 3 Baths
Enjoy the convenience of downtown Winchester living in this charming 2-bedroom, 2-bath townhome, ideally located within walking distance of restaurants, shopping, school games and more. The main level features a comfortable living area and an eat-in kitchen with doors leading to a beautiful Trex deck, perfect for morning coffee, grilling or relaxing at the end of the day. Upstairs, both bedrooms offer their own en-suite baths, with the primary bedroom also featuring a walk-in closet. The finished basement adds valuable bonus space with plenty of flexibility for a rec room, home gym, office or additional living area. From there, walk out to a beautiful stamped concrete patio and fully fenced backyard with a storage shed. With two great outdoor living spaces, a finished lower level and a location that makes it easy to enjoy everything downtown Winchester has to offer, this townhome packs a lot into a convenient footprint.

5 E Hart St, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

146 Darby Dr, Winchester
$674,900
4 Beds ⋅ 4 Baths
FRESH UPDATES & NEARLY 4,000 FINISHED SQ. FT.—COME TAKE ANOTHER LOOK AT 146 DARBY DRIVE! New flooring has just been installed in the kitchen, family room AND finished lower level, giving this spacious Ravenwing home a fresh new look! With 4 bedrooms, 3.5 baths and THREE finished levels, this home delivers something buyers are always asking for—SPACE! The main level offers multiple living areas, including formal living and dining rooms plus a spacious family room with a cozy gas fireplace. The kitchen flows right into the heart of the home, and the new flooring brings these everyday living spaces together beautifully. Upstairs is where this floor plan really stands apart. TWO PRIVATE SUITES, each with its own full bath, offer incredible flexibility, while two additional generously sized bedrooms and another full bath complete the upper level. And there’s even more downstairs! The newly refreshed finished lower level is ready to become whatever you need it to be. Create an amazing media room, game room, home gym, hobby space, office, or entertaining area. There’s already a bar area, plenty of storage, a rough-in for a future full bath, and the large TV and surround-sound system convey! The updates continue with newer double-hung windows, newer gas furnace, a 2024 tankless gas water heater, water softener, and a low-maintenance Trex deck. Add in a 2-car garage and a convenient east-side Winchester location just off Route 50, and you have a home that offers an impressive amount of space, flexibility, and recent improvements. If you’ve seen 146 Darby Drive online before, IT’S TIME TO TAKE ANOTHER LOOK. The new flooring has given this home a fresh feel—and with nearly 4,000 finished square feet, two private suites and three finished levels, there is SO MUCH HOME to discover! ** AND NOW** 🏡 146 DARBY DRIVE SAVE UP TO $700/MONTH YOUR FIRST YEAR! Seller-Paid 2-1 Buydown Enjoy payments based on a rate 2% lower the first year and 1% lower the second year. Seller pays the buydown and you enjoy the savings (with acceptable offer)

146 Darby Dr, Winchester

Listing courtesy of Samson Properties. Contact:

621 Patterson Ave, Winchester
$349,900
4 Beds ⋅ 3 Baths
Some homes simply feel right the moment you arrive—and this charming Cape Cod in an ideal in‑town Winchester location is one of them. Offering 3–4 bedrooms and 2.5 bathrooms, the layout flows with an easy, everyday comfort. The main level features two convenient bedrooms, a bright and inviting living room, a dedicated dining area, and a renovated kitchen with new cabinets and stainless‑steel appliances. In 2021, the home received a thoughtful refresh, including new vinyl plank flooring throughout, renovated bathrooms, new light fixtures, updated receptacles/switches/covers, a new roof, and updated plumbing for added peace of mind. Upstairs, two additional rooms and a full bathroom provide flexible space—whether you envision a fourth bedroom, office, or bonus retreat. With over 2,000 sq ft of finished living space, the home also includes a finished basement with a full bath and direct walkout access to the backyard, creating an ideal setting for a second living area, guest space, or recreation zone. Outdoors, a spacious deck and fully fenced backyard with privacy fencing offer a comfortable retreat perfect for relaxed evenings, weekend grilling, and easy gatherings. All of this is just moments from downtown Winchester’s shopping, restaurants, and everyday conveniences. Schedule your tour today and experience the feeling for yourself.

621 Patterson Ave, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

245 Glenridge Dr, Winchester
$379,900
4 Beds ⋅ 3 Baths
Nestled in a quiet culdesac in Glenmont Village, this charming Cape Cod boasts a beautifully landscaped front yard and wooded backyard. Enjoy secluded moments on the expansive four-level deck built around a mature oak tree, perfect for entertaining guests or simply unwinding with a good book. Refurbished in 2021, this home boasts four large bedrooms with ample closet space and three full bathrooms, ideal for couples and growing families alike. A spacious living area opens to a cozy country kitchen and dining area overlooking the deck through French doors. Parking is a breeze with a private driveway and on-street accommodations. Situated in eastern Frederick County between routes 7 and 50, minutes from Old Town Winchester, it provides easy access to Northern Virginia and the Metro area. This residence is not just a home, it's a lifestyle. Experience the charm of Glenmont Village where nature meets community and every day feels like a retreat.

245 Glenridge Dr, Winchester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

2682 Wardensville Grade, Winchester
$439,900
3 Beds ⋅ 3 Baths
ONLY TWO YEARS OLD and loaded with thoughtful upgrades! This beautifully maintained 3-bedroom, 3-full-bath home offers the appeal of nearly new construction with added features already completed for you. Inside, you’ll find beautiful hardwood floors throughout the main level, crown molding, granite countertops, and a functional layout designed for comfortable everyday living. The primary suite features a spacious walk-in closet and private bath with a walk-in shower, while the kitchen pantry provides convenient additional storage. The attached two-car garage has been upgraded with a durable epoxy floor, and the home also includes an EcoWater filtration system, water softener, and French drain system around the property. The unfinished basement provides abundant storage today and exciting potential for future finished living space, a recreation room, home office, gym, or more. Conveniently located just minutes from town, this nearly new home combines modern finishes, valuable upgrades, and room to grow. Move in and enjoy — the hard work has already been done!

2682 Wardensville Grade, Winchester

Listing courtesy of Ross Real Estate. Contact:

540 Monticello St, Winchester
$605,000
Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Downtown Winchester Location! Presenting a Triplex in the heart of Downtown Winchester—a rare opportunity for investors seeking strong cash flow in a highly desirable and commuter-friendly location. Just minutes from I-81 and I-66, and less than an hour from Northern Virginia, this property offers convenience, charm, and long-term value. The building features two 2-Bedroom, 1-Bath Units – Each offers large Kitchens, updated finishes, and their own Laundry Rooms. One of the units is ground level, and the other 2nd-Level unit has access to its own deck space. The largest unit of the three features two finished levels, connected with an interior staircase, 5-Bedrooms, 2 Full Baths, 2 Living Rooms, a Full kitchen, Laundry, and access to it's own private patio & deck. It's a unique two-level layout, perfect for multi-tenants and/or premium rental rates. Recent renovations throughout the last few years include: Luxury vinyl plank (LVP) flooring, fresh paint, and updated kitchens and baths Newer appliances in each unit The roof less than 3 years old New HVAC installed (2025) Designated parking for all units With all units currently leased, this is a true turnkey investment with reliable income and minimal immediate maintenance needs. This well-maintained building features three fully occupied units, bringing in a current gross annual rental income of $45,300. Whether you're looking to grow your portfolio or occupy a unit while renting the others, or the potential for a short-term rental, this property checks all the boxes!

540 Monticello St, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

199 Dicks Hollow Rd, Winchester
$340,000
5 Beds ⋅ 1 Baths
Steeped in heartwarming history and beautifully updated, this charming country home sits on nearly 2 acres of serene land with a small stream in the back. Originally the seller’s "grandma’s house" ... he has meticulously preserved some elements and thoughtfully modernized over the last six years, perfectly blending nostalgic character with modern comfort. He has fond memories of good times in this home from the wonderful smells from grandma baking to building boats in the basement with grandpa and floating them in the little creek that runs behind the house. Step inside to find gleaming refinished hardwood floors and a highly flexible layout featuring at least one main-floor bedroom (with the option for a second if you choose to repurpose the formal dining room). The unexpected crown jewel of the home is a massive walk-in dressing room with boundless space for clothes and personal items. Recent high-value updates give you ultimate peace of mind, including a new HVAC system (2024), new windows, updated siding, a painted roof, a highly efficient exterior wood heating system, and freshly upgraded kitchen countertop and bathroom vanity/countertop. Outside, the expansive property offers the perfect canvas for your farmette dreams. Ideally located just off Route 50 and only 10 minutes from the Winchester Medical Center, this home is IDEAL for just about anyone. Come see for yourself all this CUTENESS overload but be careful ... you just might fall in LOVE! Note: Because the seller has meticulously upgraded and maintained the property, it is being sold as-is. Inspections are welcome for buyer informational purposes, but the seller will make no repairs. This home is ready for you to move right in and start building your own lifelong memories.

199 Dicks Hollow Rd, Winchester

Listing courtesy of RE/MAX Roots. Contact:

208 Lauck Dr, Winchester
$378,000
3 Beds ⋅ 2 Baths
STOP THE PRESSES - Great Winchester Location and priced under $380k!! Location, value, and opportunity come together at 208 Lauck Drive in Winchester’s Star Fort neighborhood!<br><br> If location and value are at the top of your list, 208 Lauck Drive deserves a look. With its convenient Winchester location and major updates already completed, this home offers a wonderful opportunity to personalize over time while enjoying everything the area has to offer.<br><br> This well-kept home offers comfortable living space, an attached garage, and a convenient location just minutes from Winchester Medical Center, Old Town Winchester and the Walking Mall, shopping, dining, and major commuter routes.<br><br> Step inside to a spacious family room with plenty of room to gather and relax, highlighted by a fireplace and an abundance of natural light. The adjoining dining room provides generous space for everyday meals or entertaining, while the kitchen offers ample cabinetry, counter space, and a pass-through to the dining area.<br><br> Some of the important updates have already been taken care of, including a new roof, newer HVAC system, and newer water heater—giving the next owner a great starting point to make the home their own.<br><br> Outside, enjoy a nice-sized yard with mature trees, rear deck, and plenty of room for outdoor activities. Add in the attached garage and an established Winchester neighborhood, and there is a lot to appreciate here.<br><br> Come see the possibilities at 208 Lauck Drive—schedule your showing today!

208 Lauck Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact:

107 Little River Dr, Winchester
$260,000
2 Beds ⋅ 1 Baths
Affordable Winchester Townhome with Investment Potential! Welcome to 107 Little River Dr, a conveniently located 2-bedroom, 1-bath townhome offering an excellent opportunity for a first-time buyer, downsizer, or investor. This two-level home provides approximately 900+ square feet of living space with a practical layout and plenty of potential to make it your own. Located in the Brookland Heights community, the property offers easy access to Winchester-area shopping, dining, employment centers, and major commuter routes. The low-maintenance townhome lifestyle makes this an attractive option for buyers looking for affordability and convenience. Whether you're searching for a primary residence, rental property, or value-add investment, 107 Little River Dr is worth a look. Bring your vision and unlock the potential of this Winchester opportunity!

107 Little River Dr, Winchester

Listing courtesy of EXP Realty, LLC. Contact:

151 Nevermore Dr, Winchester
$619,900
4 Beds ⋅ 4 Baths
***Seller has an assumable VA loan with a 4.99% interest rate. Contact listing agent for details!*** Welcome to 151 Nevermore Drive, a home that truly has it all! Built in 2022 but shows like new, this home is located in the highly desirable Raven Oaks community and sits on one of the neighborhood’s premium lots within a cul-de-sac. The private fenced backyard backs to a wooded common area and features a Trex deck. Inside, this 4-bedroom, 3.5-bath home offers an impressive combination of space, features, and functionality. There is nothing left to do but move in and enjoy! The main level features a high-end kitchen with granite countertops, a gas cooktop, double wall ovens, and plenty of space for entertaining. The open living area features an electric fireplace with a stone surround, and a dedicated office provides a great space for working from home. Upstairs, you’ll find a versatile loft, convenient laundry room, and four bedrooms, including the spacious primary suite. The finished lower level offers natural light, a full bath, and walk-up access directly to the backyard. An additional unfinished room with an egress window offers the opportunity to create a legal fifth bedroom, while the large storage room provides plenty of room for everything else. The home also features efficient gas heat, a high-efficiency tankless water heater, and a water softener that is already installed. Raven Oaks offers a fantastic community lifestyle with a neighborhood pool and tot lot, while being less than 10 minutes from downtown Winchester and under an hour from Dulles International Airport. With its private wooded setting, premium lot, fenced backyard, Trex deck, cul-de-sac location, and like-new condition, 151 Nevermore Drive is a home you won’t want to miss. If you’ve been considering new construction, come see what this home has to offer before you build!

151 Nevermore Dr, Winchester

Listing courtesy of Colony Realty. Contact:

103 Elaine Dr, Winchester
$379,900
3 Beds ⋅ 2 Baths
Welcome to this charming 3 bed 2 bath ranch home offering approximately 1500 sq ft of comfortable one level living on the east side of Frederick County. The home features a practical layout for everyday living. Recent improvements include new flooring in the kitchen, new carpet in the bedrooms, new rear patio, and the roof and HVAC have been replaced within the last 3 years. The large lot provides plenty of room for outdoor activities, gardening or future possibilities. Conveniently located near RT7, this home offers an easy commute towards Northern VA while providing the space and value of Frederick County living. Great opportunity for buyers looking for a well-located ranch home with updates and generous outdoor space.

103 Elaine Dr, Winchester

Listing courtesy of Coldwell Banker Premier. Contact:

151 Huron Trl, Winchester
$324,950
3 Beds ⋅ 2 Baths
A view you'll never tire of coming home to! Tucked among mature trees and established landscaping in the desirable Shawneeland community, this charming 3-bedroom, 2-bath home offers a wonderful combination of privacy, natural beauty and comfortable one-level living. Here, the surrounding scenery becomes part of everyday life, changing with the seasons and providing a beautiful backdrop throughout the year. Step onto the deck with your morning coffee and take in the peaceful surroundings and picturesque views across the Winchester landscape. From the colors of fall to the beauty of a setting sun, there is always something new to appreciate. Inside, the home offers 1,248 finished square feet of living space with 3 bedrooms, 2 bathrooms, an open plan kitchen/dining room and a spacious family room which provdes access to the beautiful front deck. The home benefits from fresh paint throughout several areas of the main level adding to the home’s bright, welcoming feel. The practical ranch-style layout provides comfortable everyday living, while the attached one-car garage adds convenience and storage. The home has also benefited from several important updates in recent years, including the HVAC system, water heater, pressure tank, and updated washer and dryer, with the roof replaced in 2021. Beyond the property itself, enjoy the natural surroundings and established character of Shawneeland, with community amenities including fishing, playgrounds, picnic areas and a four-hole golf course. And with NO HOA, homeowners can enjoy an added level of freedom that's increasingly difficult to find. Just beyond the peaceful surroundings of home, the shops, restaurants, coffee houses and historic charm of Winchester are only a short drive away. Spend an afternoon strolling the Old Town Walking Mall, meet friends for dinner, or enjoy one of the many events that bring the area to life throughout the year. Commuters will appreciate easy access to major routes including Routes 50 and 7, as well as I-81, providing convenient connections throughout the Winchester area and beyond. Travel east toward Clarke and Loudoun Counties, including Berryville, Purcellville and Leesburg, or connect with major corridors serving the greater Northern Virginia region. At 151 Huron Trail, the view isn't something you simply notice when you arrive—it becomes part of the way you live. Come experience the privacy, changing seasons and spectacular sunsets for yourself. Enjoy your tour!

151 Huron Trl, Winchester

Listing courtesy of Pearson Smith Realty, LLC. Contact:

409 Fortress Dr, Winchester
$499,900
4 Beds ⋅ 4 Baths
Big, beautiful, and ideally located, this spacious three-level Colonial offers 4 bedrooms, 3.5 baths, over 3,100 finished square feet, a 2-car garage, and a fully finished walkout basement. All situated on a generous half-acre lot. The main level features new LVP flooring, a spacious kitchen with center island, stainless steel appliances, multiple living and entertaining spaces, separate dining and a cozy fireplace. Upstairs, you'll find LVP flooring continued, generously sized bedrooms & closets, including an impressive sized primary suite with a walk-in closet and private bath. The fully finished walkout lower level has a full bath & adds even more living space with plenty of flexibility for a recreation room, home office, gym, guest area, or combination of uses. Outside, enjoy a large half-acre lot backing to mature trees, offering added privacy and plenty of room to enjoy the outdoors or watch your kiddos or fur-babies play. The location is hard to beat. Just minutes from shopping, dining, schools, Winchester Medical Center, and major commuter routes including Route 37, Route 522, and I-81. Best of all, enjoy the convenience of Winchester without city taxes or HOA fees! ** Seller is offering a 1 yr home warranty.**

409 Fortress Dr, Winchester

Listing courtesy of NextHome Realty Select. Contact:

123 Averrell Ave, Winchester
$139,000
3 Beds ⋅ 3 Baths
Welcome to relaxed and comfortable living in the desirable Regency Lakes community of Winchester, where this remarkably large and expansive manufactured home stands out exceptionally from neighboring properties by offering vastly superior square footage, an extended exterior profile, and a deep, generous footprint. Step inside to discover a truly massive, open-concept living area featuring stunning floor-to-ceiling stone accent fireplaces, soaring ceilings, and abundant space for oversized furniture and grand entertaining. A chef-styled kitchen boasts an immense array of rich wooden cabinetry, a brand-new gas cooktop, an expansive center prep island, and a seamless flow into the adjoining dining room. Recent updates further elevate the home, including new carpet (installed in 2023) and new wood floors in the guest room. Combining this unmatched scale with a functional floor plan designed to maximize everyday living, a wide covered front porch, and a private storage shed on a wonderful lot, the home provides quick access to local parks, schools, commuter arteries, and historic downtown Winchester for a lifestyle far bigger than the rest. This residency pays a ground rent of $953 that includes the following community amenities: swimming pool, whirlpool/spa/hot tub, clubhouse, fitness center, tennis courts, basketball and volleyball courts, a playground, picnic areas, horseshoes, fishing, waterfront sites, RV storage, on-site management, pet-friendly spaces, and regular community activities.

123 Averrell Ave, Winchester

Listing courtesy of Spring Hill Real Estate, LLC.. Contact:

187 Village Ct, Winchester
$399,737
4 Beds ⋅ 2 Baths
<b>**WOW!!!** NEW PRICE + EXCEPTIONAL VALUE IN WINCHESTER!</b> Move-In Ready • No HOA • Fantastic Location Across from Winchester Country Club! | Tucked away on a quiet cul-de-sac in the desirable Rolling Fields community, this beautifully updated Split Foyer offers a spacious .38-Acre Lot, peaceful tree-lined backyard & an <b>EXTRA-DEEP OVERSIZED 2-CAR GARAGE!</b> | Freshly Painted throughout with Brand-New Carpet, Gleaming Hardwood Floors & updated Luxury Vinyl Plank Flooring, this home is truly Move-In Ready | The bright & inviting Main Level features a spacious Living Room, Formal Dining Room & Eat-In Kitchen with Granite Countertops & Stainless Steel Appliances | 3 Main-Level Bedrooms & 2 Full Baths include a comfortable Primary Suite with Private Bath | The Finished Lower Level provides even more flexible living space with a Large Recreation Room, 4th Bedroom, Laundry Area & direct access to the Oversized Garage—offering exceptional room for Vehicles, Storage, Hobbies or a Workshop | Relax on the Covered Front Porch or head out back to the <b>FRESHLY STAINED DECK WITH ALL-NEW DECK BOARDS & HANDRAILS</b> overlooking the spacious, tree-lined backyard | <b>NOTABLE RECENT IMPROVEMENTS INCLUDE:</b> Freshly Stained Deck + New Deck Boards & Handrails (Sept. 2026), Fresh Interior Paint (2026), New Carpet (2026), Updated Vanity Lighting in Both Bathrooms (2026), Kitchen & Primary Bath Luxury Vinyl Plank Flooring (2025), Dishwasher (2025), Dryer (2022), Water Heater (2022), Refrigerator (2021), Roof (2017) & Garage Doors (2008) | Conveniently located just minutes from Shopping, Dining, Schools, Commuter Routes & Historic Downtown Winchester | <b>WITH ITS NEW PRICE, NO HOA, .38-ACRE LOT, OVERSIZED GARAGE & EXTENSIVE UPDATES, THIS HOME OFFERS AN EXCEPTIONAL VALUE—DON'T MISS IT!</b>

187 Village Ct, Winchester

Listing courtesy of RE/MAX Distinctive Real Estate, Inc.. Contact:

101 Poe Dr, Winchester
$619,900
4 Beds ⋅ 3 Baths
Welcome 101 Poe Drive! You are going to swoon over this gorgeous, model-quality home located in the desirable Raven Oaks neighborhood. This beauty boasts nearly 2,800 square feet of above-grade living space, complete with four bedrooms, two and a half baths, and an amazing loft area upstairs that is currently being used as an adorable play area. Once you step inside the front door, you’ll instantly notice the elegant finishes throughout the home, such as LVP flooring, stainless steel appliances, quartz countertops, and upgraded light fixtures. The main floor layout makes everyday life – or entertaining guests - a breeze. It offers a home office/flex space, a convenient walk-in pantry, and a large kitchen island. Need lots of natural light? The fabulous sunroom situated off the kitchen was designed just for you – and will not disappoint! Upstairs, four generously sized bedrooms await, as well as the laundry room. The luxurious primary suite will feel like your own private retreat, boasting a spa-inspired bath with an oversized walk-in shower and a massive walk-in closet. In the basement, you will find a finished flex space, while the expansive unfinished area - with a bathroom rough-in and an egress window in place - offers endless possibilities for future expansion. This home sits on a fantastic corner lot at the top of a quiet cul-de-sac. The community offers exceptional amenities, including a clubhouse, pool, tennis and basketball courts, and two playgrounds. Situated close to Rt-50, Rt-7, and I-81, you will find that shopping, dining, and historic downtown Winchester are all just minutes away. Don’t miss your chance to own this exquisite, move-in-ready home. Schedule your tour today!

101 Poe Dr, Winchester

Listing courtesy of Samson Properties. Contact:

138 Wappinger Ter, Winchester
$530,345
5 Beds ⋅ 3 Baths
Located on a desirable cul-de-sac, Lot 48 features the spacious Elm floor plan and is expected to be ready for a November closing! This thoughtfully designed home offers five bedrooms, three full bathrooms, and a two-car garage. The open-concept main level features a modern kitchen with a large center island, quartz countertops, stainless steel appliances, and a walk-in pantry overlooking the dining area and great room. A main-level bedroom and full bathroom provide excellent flexibility for guests or a home office. Upstairs, you’ll find a spacious primary suite with a private bathroom and walk-in closet, three additional bedrooms, a versatile loft, and a conveniently located laundry room. Enjoy the space, comfort, and convenience of a brand-new home in a peaceful cul-de-sac setting. *Photos, 3D tours, and videos are representative of plan only and may vary as built.*

138 Wappinger Ter, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

2817 Papermill Rd, Winchester
$325,000
3 Beds ⋅ 2 Baths
Welcome to 2817 Papermill Road, a beautifully maintained home that reflects true pride of ownership from the moment you arrive. Situated on an impressive approximately 0.35-acre lot, this property offers a wonderful combination of space, comfort, and convenience all while being just minutes from everything Winchester has to offer. The home has been thoughtfully cared for and kept in excellent condition, creating a warm and welcoming atmosphere that is ready for its next owner to enjoy. Outside, the spacious lot provides plenty of room to relax, entertain, garden, play, or simply enjoy having some extra breathing room without sacrificing the convenience of being in the city. One of the property's standout features is the abundance of parking available in front of the home, making it easy to accommodate multiple vehicles and guests. Whether you're hosting family and friends or simply appreciate having extra parking space, this home delivers. Location is another major highlight. Enjoy convenient access to Downtown Winchester, shopping, restaurants, schools, parks, everyday necessities, and major commuter routes, while still coming home to a property with plenty of outdoor space to call your own. With its generous lot, well-cared-for condition, ample parking, and convenient Winchester location, 2817 Papermill Road offers a combination that's increasingly hard to find. Come see what makes this home special—you may just find the space, location, and feeling of home you've been looking for.

2817 Papermill Rd, Winchester

Listing courtesy of Weichert, REALTORS. Contact:

112 Wappinger Ter, Winchester
$599,990
5 Beds ⋅ 5 Baths
Situated on a desirable cul-de-sac homesite backing to community open space, this thoughtfully designed home offers the perfect blend of comfort and functionality. The main level features a spacious owner's suite, formal dining room, laundry room, powder room, and an open-concept kitchen overlooking the living and dining areas. The kitchen includes quartz countertops, an island with seating, pantry, and breakfast nook. Upstairs, you'll find four additional bedrooms, including a private en-suite and a shared full bath. Designer-selected finishes, luxury vinyl plank flooring, whole-house blinds, smart home features, stainless steel appliances, refrigerator, washer, and dryer are all included. *Photos, 3D tours, and videos are representative of plan only and may vary as built.

112 Wappinger Ter, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact:

132 Darby Dr, Winchester
$645,000
4 Beds ⋅ 4 Baths
Welcome to this beautiful single-family home in the sought-after Ravenwing neighborhood of Winchester, Virginia. The sellers are open to offers that include credits toward financing or flooring. Key systems have been updated, featuring a new water heater installed in 2022 and a brand-new roof completed in 2024. Conveniently located near local shopping, downtown Winchester, Costco, I-81, Route 50, and Route 7, this spacious two-story property offers over 3,500 square feet of comfortable living space tailored for modern living. The main level features a large kitchen complete with an island and a generous pantry, seamlessly connecting to a formal dining room, an open living room enhanced by custom built-in shelves, a versatile flex room, and a convenient half bath. Upstairs, the expansive primary bedroom serves as a private retreat with two walk-in closets and a dedicated en suite bathroom. Three additional bedrooms, a second full bathroom, and a conveniently located laundry room round out the upper floor. The finished basement adds over 800 square feet of versatile living space, complete with a third full bath and direct access to the outdoors. Outside, the quarter-acre lot features a fenced yard area and a back deck ideal for morning coffee or casual gatherings. Don't miss this opportunity to live in one of the most sought-after neighborhoods in Winchester!

132 Darby Dr, Winchester

Listing courtesy of Dream Real Estate. Contact:

143 Wappinger Ter, Winchester
$599,990
6 Beds ⋅ 4 Baths
Rare cul-de-sac home! The Hayden offers 6 bedrooms, 4 bathrooms, and over 3,100 square feet of beautifully designed living space. The open-concept main level features a flex room, a bedroom with full bath, and a spacious kitchen that flows seamlessly into the dining and living areas. Upstairs, enjoy a luxurious owner's suite, three additional bedrooms, a loft, and convenient laundry room. The finished walkout basement adds a recreation room, bedroom, and full bath, providing even more room to live and entertain. This home includes designer-selected finishes, quartz countertops, luxury vinyl plank flooring, a whole-house blinds package, laundry appliances, French door refrigerator, and backs to a peaceful setting in desirable Retreat at Winding Creek. October delivery! *Photos, 3D tours, and videos are representative of plan only and may vary as built.

143 Wappinger Ter, Winchester

Listing courtesy of D R Horton Realty of Virginia LLC. Contact: