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105 Biscane Ct, Winchester
$420,000
3 Beds ⋅ 4 Baths
Discover a serene retreat that invites you to unwind and embrace the comforts of home. This charming townhome, with its warm ambiance and thoughtful design, is a canvas ready for your personal touch. Imagine cozy evenings spent by the fireplace, where the flickering flames create a welcoming atmosphere for gatherings or quiet nights in. The spacious layout offers endless possibilities for customization, allowing you to create the perfect living space tailored to your lifestyle. Whether you envision a modern open-concept design or a more traditional layout, this property provides the flexibility to bring your vision to life. Natural light floods the interior, enhancing the inviting atmosphere and highlighting the potential for beautiful decor. Step outside to discover a blank canvas for your outdoor oasis. The expansive yard offers ample space for gardening, outdoor dining, or simply enjoying the fresh air. Picture summer barbecues with friends or peaceful mornings sipping coffee on your porch, surrounded by nature's beauty. This property is not just a house; it's a place where memories are made. The fireplace serves as a focal point, perfect for cozy gatherings during chilly evenings, while the overall layout encourages a seamless flow between spaces, making it ideal for both entertaining and everyday living. Located in a tranquil neighborhood, you'll enjoy the peace and privacy that comes with this setting, while still being conveniently close to local amenities. Explore nearby parks, shops, and dining options, all just a short drive away, ensuring that everything you need is within reach. This is more than just a property; it's an opportunity to create a home that reflects your unique style and aspirations. With its inviting features and potential for personalization, this home is ready to welcome you into a life of comfort and joy. The home features new carpet in the basement and fresh paint throughout.

105 Biscane Ct, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

316 Crow Dr, Winchester
$240,000
2 Beds ⋅ 1 Baths
Lovely home offering flexible living space, wooded surroundings, and more room to make everyday life your own. Set within the Wilde Acres/Mountain Falls community, this Winchester property features a split-foyer layout with distinct living areas and a full basement, providing added flexibility for relaxing, entertaining, hobbies, working from home, storage, and more. Beyond the home, enjoy outdoor recreation within the community, spend a day exploring the Shenandoah Valley, or head into historic Old Town Winchester for restaurants, shops, events, and the pedestrian mall. Jim Barnett Park, Apple Blossom Mall, and additional shopping and services provide even more options for recreation and everyday needs. When plans take you farther, I-81, I-66, Route 50, Route 7, and Route 522 provide connections toward Northern Virginia, Front Royal, and destinations throughout the Shenandoah Valley. With adaptable space at home, wooded surroundings, outdoor opportunities, and Winchester conveniences within reach, this property gives you more ways to enjoy where you live. Photos may be virtually staged

316 Crow Dr, Winchester

Listing courtesy of Keller Williams Realty. Contact:

3016 Siler Rd, Winchester
$649,900
2 Beds ⋅ 1 Baths
WILLOW POND. Very difficult to find larger acreage 15 minutes from Winchester. 47+ acres with a very unique cabin. Land is wooded with tall hardwoods, pines. The cabin was constructed in 1966, by the same family that continues to own the property. The cabin is private, located pretty much in the middle of the property, with a long driveway. The home overlooks an acre pond. The cabin was built from a custom kit, utilizing vaulted ceilings and exposed log rafters. The interior walls are tongue-n-groove pine boards. The wood exterior has been covered with aluminum siding. Casement windows and roof shingles (architectural) have been replaced in the recent past. Within the wooded land, there are two open fields of a few acres each. At the back end of the land there is a trail that runs between this and the neighbor's property that is supposedly a part of the Tuscarora Trail. The land has long road frontage (approximately 1800') on state maintained Siler Road. Call for more details. Come take a walk or a ride!

3016 Siler Rd, Winchester

Listing courtesy of Cedar Creek Real Estate. Contact:

2660 Daniel Ter, Winchester
$335,000
2 Beds ⋅ 2 Baths
Well maintained three story, all brick townhome located in the City of Winchester. This home is on a quiet street and conveniently located close to shopping and restaurants. There are hardwood floors throughout the main level consisting of the kitchen/dining area, living room, and half bath. There are two nice sized bedrooms and one full bath on the upper level, along with separate laundry. (Maytag washer and dryer purchased in 2024 convey with property) The lower level has a finished living space with electric baseboard heat and could be comfortably used as a family room, office, or additional bedroom. Directly off the finished lower level are a one car garage and storage area. (The new freezer located in garage also conveys) This townhome comes with plenty of parking, whether it is street parking in front, a private concrete driveway in the rear, or the rear loading garage. (Townhome is being freshly painted throughout.) Townhomes in this subdivision rarely come to market, so don't wait! PROFESSIONAL PHOTOS COMING SOON.

2660 Daniel Ter, Winchester

Listing courtesy of MarketPlace REALTY. Contact:

251 Waterford Ln, Winchester
$279,000
3 Beds ⋅ 2 Baths
Welcome to 251 Waterford Lane, a charming 3-bedroom, 1.5-bath end-unit townhome in Winchester, VA, offering comfortable living in a convenient commuter location. The traditional-style floor plan features a spacious living room and an inviting eat-in kitchen, providing plenty of room for everyday living and entertaining. The end-unit setting offers added privacy, while the fenced backyard and patio create a great outdoor space for relaxing, gardening, or enjoying time with family and friends. Conveniently located for commuters, this Winchester townhome provides easy access to major commuter routes, making travel throughout the Northern Shenandoah Valley, Northern Virginia, West Virginia, Maryland, and surrounding areas convenient. Enjoy proximity to downtown Winchester, Old Town Winchester, Shenandoah University, shopping, restaurants, parks, and a variety of local attractions. Whether you’re looking for a Northern Virginia commuter home, a convenient Winchester townhome, or a home with easy access to local attractions and everyday amenities, 251 Waterford Lane offers a combination of location, comfort, privacy, and convenience. HVAC -2021, Hot Water Heater 2021. Newer appliances, carpet, storm doors, and patio. All sizes are approximate.

251 Waterford Ln, Winchester

Listing courtesy of RE/MAX Roots. Contact:

1308 Commerce, Winchester
$299,900
3 Beds ⋅ 1 Baths
Charming, cheerful, and filled with natural light, this inviting 3-bedroom, 1-bath rancher makes a delightful first impression. Fresh yellow siding, mature trees, blooming hydrangeas, and classic boxwoods create beautiful curb appeal, while convenient main-level living makes the home as practical as it is welcoming. Inside, gleaming hardwood floors and abundant sunlight lend warmth to every room. The beautifully updated bath features a walk-in shower, and the centrally located kitchen offers generous cabinetry and plenty of room for shared meals. Ideally situated between the formal living room and cozy den, the kitchen provides an easy flow for everyday living and entertaining. Rich wood walls and a wood stove give the den its distinctive character. Adding a special piece of Winchester history, the paneling was salvaged from the former Lee-Jackson Hotel banquet room. Downstairs, the climate-controlled, partially finished lower level offers wonderful possibilities for a recreation room, playroom, home gym, or office, along with ample workshop and storage space. A relaxing screened porch overlooks the spacious backyard with peonies and a cherry tree, creating a peaceful spot to enjoy the outdoors. Lovingly cared for by the same family since it was built, this sweet home has been recently painted throughout and features roof (July 2025), new HVAC system (July 2026), update bathroom (2024) and newer 20-year tilt in windows, and updated lighting. Whether you are searching for your first home or looking to downsize, this special property is well worth a visit. Schedule your tour today!

1308 Commerce, Winchester

Listing courtesy of Colony Realty. Contact:

151 Travis Ct, Winchester
$524,900
4 Beds ⋅ 4 Baths
FRESHLY IMPROVED & READY FOR A NEW OWNER! There is even more to love about 151 Travis Court, including a BRAND-NEW ROOF and freshly power-washed exterior! Located on a cul-de-sac in desirable Red Fox Run, this spacious home offers 5 bedrooms, 3.5 baths, three finished levels and the space and flexibility today's buyers are looking for. Step inside to a bright, welcoming floor plan with generous living spaces perfect for everyday life and entertaining. The spacious kitchen offers plenty of room to gather and flows easily into the main living areas. Upstairs, you'll find comfortable bedrooms, including a roomy primary suite, while the finished lower level adds a 5th bedroom, full bath and additional living space - ideal for guests, extended family, a home office, recreation space or whatever fits your lifestyle. Outside, enjoy the deck overlooking the fenced backyard on a .31-acre lot with plenty of room for relaxing, entertaining, pets or play. Additional updates include a newer main HVAC system, upper HVAC serviced in 2026, appliances replaced in 2022, new refrigerator and family room carpet in 2026. With the NEW ROOF now complete, recent exterior improvements, abundant living space and a convenient Winchester location, 151 Travis Court offers a lot of home for the price. If you've seen this home before, it's worth another look - and if you're seeing it for the first time, now is the time to see it! Schedule your showing and come see everything 151 Travis Court has to offer.

151 Travis Ct, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

4208 Apple Pie Ridge Rd, Winchester
$650,000
4 Beds ⋅ 2 Baths
Welcome to peaceful country living on sought-after Apple Pie Ridge. This farmette situated on approximately 6.34 acres, offers the space, privacy, and charm that make Shenandoah Valley living so desirable. The home features four bedrooms, two bathrooms, warm knotty pine flooring, generous living space, and numerous practical improvements that create a comfortable country lifestyle. With one bedroom and bathroom on the main level, the home is conveniently set up for all stages of life. Outside, enjoy open acreage with room for gardening, recreation, or simply taking in the surrounding countryside. A detached garage with a wood stove provides excellent workshop or hobby space, while the basement and attic offer additional storage and flexibility. Whether you're looking for room to spread out, a place to enjoy quiet evenings, or a property that balances rural living with convenient access to Winchester, this home offers a wonderful opportunity. Experience the beauty of Apple Pie Ridge while enjoying the comfort of a well-maintained country home.

4208 Apple Pie Ridge Rd, Winchester

Listing courtesy of Virginia Real Estate. Contact:

Homesite 40 Shuoner Court, Winchester
$399,999
4 Beds ⋅ 4 Baths
🏡 Winter Delivery – St. Paul LAST END UNIT!! 4 Bedrooms | 3.5 Bathrooms | Finished Lower Level | Larger Composite Deck | 🔥 Beautiful wooded homesites are available! Enjoy up to 2,250 sq. ft. of modern, open-concept living. Customize the home to fit your style, or keep the included selections as-is at the advertised price—including the fourth bedroom and full bathroom on the lower level. ✨ Home Highlights 🍽 Open-concept main level—perfect for entertaining 🪨 Granite countertops 🧰 Stainless steel appliances 🪵 Luxury vinyl plank flooring 🛌 Upper-Level Retreat 🚿 Deluxe Silver primary bathroom with rain shower 👕 Spacious walk-in closet 🧺 Bedroom-level laundry 🛏 Two additional bedrooms and a full bathroom 🎬 Finished Lower Level 🛏 Fourth bedroom 🛁 Full bathroom 💼 Ideal for guests, a home office, gym, or media room 🌟 Additional Features 🌳 Townhome landscaping package 🔌 Deako smart light switches and smart-home features 🌅 Larger composite deck 🏦 Special financing programs available 💰 Builder incentives available when using the preferred lender 📅 Projected delivery: WINTER 📲 Contact the listing agent for current pricing and incentives. 📸 Photos are representative and may show optional features.

Homesite 40 Shuoner Court, Winchester

Listing courtesy of New Home Star Virginia, LLC. Contact:

118 Shuoner Ct, Winchester
$374,990
3 Beds ⋅ 3 Baths
🏡 MOVE IN READY NOW ✨ St. Paul Townhome TBB | 3 BR | 2.5 BA | 🚗 1-Car Garage | Finished Lower Level 🔥 Beautiful wooded homesites available! Offering up to 2,000 sq. ft. of modern, open-concept living designed for today's lifestyle. ✨ Home Highlights 🍽 Open-concept main level — perfect for entertaining family and friends 🪨 Granite countertops 🧰 Stainless steel appliances 🪵 Luxury vinyl plank flooring throughout the main level 🛌 Upper Level Retreat 🚿 Deluxe Silver primary bath with spa-inspired rain shower 👕 Spacious walk-in closet 🧺 Convenient bedroom-level laundry 🛏 Two additional bedrooms and a full bath 🎬 Finished Lower Level 🛁 Finished recreation room 🛏 Beautiful 12" x 24" tile in all full bathrooms and laundry room 💼 Perfect space for guests, a home office, gym, media room, or playroom 🌟 Additional Features 🌳 Professionally designed townhome landscaping package 🔌 Deako smart light switches and smart home features 🏡 Energy-efficient construction and modern finishes throughout 🏦 Special financing programs available 💰 Builder incentives available with preferred lender 📅 MOVE IN READY NOW 📲 Contact Jimmy Thomas for current pricing, available homesites, and incentives. 📸 Photos are representative and may show optional features.

118 Shuoner Ct, Winchester

Listing courtesy of New Home Star Virginia, LLC. Contact:

1013 Orchard Hill Dr, Winchester
$299,900
3 Beds ⋅ 2 Baths
Updated, move-in ready, and waiting for you to make it your own! Welcome to 1013 Orchard Hill Dr. Tucked away in a charming, established Winchester neighborhood with no HOA, this inviting townhome combines a clean, comfortable style with many of the big-ticket improvements already taken care of. Outside, you'll find a brand-new roof and vinyl siding, fresh landscaping, and an updated rear deck complete with durable vinyl railing. Step inside to a spacious main level with an easy, open flow between the living and dining areas. The living room is warm and welcoming, centered around a wood-burning fireplace with built-in cabinetry on both sides, the perfect spot to settle in on a cool evening. The adjoining galley-style kitchen offers plenty of functionality with the laundry conveniently located just off the kitchen. Beyond the dining area, the home gets even better with a large bonus sunroom, complete with additional built-ins and an entire wall of pantry storage. Whether you envision it as a casual gathering space, home office, hobby area, or simply a place to enjoy the extra room, this flexible space adds even more versatility to the home. Upstairs, new carpeting runs throughout, complemented by fresh paint in the entire home. The brand-new full bathroom features a tub/shower combination and new vanity, giving the space a crisp, updated feel. The best part? The major exterior work has already been done, the home is clean and move-in ready, and there's still plenty of opportunity to bring your own style to the interior. Priced competitively, 1013 Orchard Hill Dr offers an opportunity to enjoy a desirable Winchester setting, the freedom of no HOA, and a home where the important updates have already been taken care of. Come see it for yourself and imagine what you'll do with the rest!

1013 Orchard Hill Dr, Winchester

Listing courtesy of Realty ONE Group Old Towne. Contact:

121 Elmwood Rd, Winchester
$339,000
2 Beds ⋅ 2 Baths
Welcome to this 2 bedroom, 1.5-bath brick rancher in Bufflick Heights in Winchester, VA. The home features hardwood flooring in the living room and bedrooms, with an inviting living room offering an electric fireplace and plenty of natural light. The kitchen provides ample cabinet and storage space and is equipped with double sinks, a wall oven, and cooktop. The primary bedroom offers two closets plus a convenient makeup desk area. Outside, enjoy a nicely landscaped yard and a brick walkway leading to the front porch, a great spot to sit and enjoy your morning coffee or relax at the end of the day. A covered walkway provides easy access to the attached garage, which includes a walk-up storage area. Several additional storage buildings provide plenty of room for tools, hobbies, and extra storage. An asphalt driveway completes the property, offering comfortable one-level living with plenty of storage and classic brick exterior appeal.

121 Elmwood Rd, Winchester

Listing courtesy of ERA Oakcrest Realty, Inc.. Contact:

140 Swansong Pl, Winchester
$409,990
4 Beds ⋅ 4 Baths
BUILDER OFFERING BELOW MARKET RATE FINANCING OPTION ON THIS QUICK MOVE IN HOME!! Brand-New 4-Bedroom Townhome under construction for Move-In soon! Enjoy stylish, low-maintenance living in Snowden Bridge's newest section. This thoughtfully designed home features a convenient entry-level bedroom, oak stairs with upgraded railings, and luxury vinyl plank flooring throughout the main level. The bright gourmet kitchen showcases elegant cabinetry, quartz countertops, and stainless steel appliances, flowing seamlessly into the open living spaces. Upstairs, the spacious primary suite provides a private retreat. Located in a vibrant community with resort-style amenities including a pool, playgrounds, trails, and more to come. Ask about builder incentives! Photos are of a similar home while construction is ongoing.

140 Swansong Pl, Winchester

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact:

116 E Cork St, Winchester
$389,000
2 Beds ⋅ 1 Baths
A RARE DOWNTOWN GEM IN THE HEART OF HISTORIC WINCHESTER! Discover the charm and convenience of this beautifully restored circa-1900 row house, ideally located just one block from Winchester’s iconic Walking Mall. Enjoy an exceptional walkable lifestyle with an array of restaurants, coffee shops, boutiques, and nightlife right outside your door - all with no HOA! Thoughtfully renovated from top to bottom, this home combines historic character with modern comfort, featuring updated plumbing and electrical systems, beautiful hardwood flooring, and a spacious gourmet kitchen with granite countertops and convenient direct access to the rear deck featuring a relatively new 6' privacy fence—perfect for outdoor dining, entertaining or simply relaxing after a long day. Additional highlights include a front-loading washer and dryer, ceramic tile bath, high-end window treatments, and a generous walk-in closet. The transformation continues outside, where the fully restored and freshly painted exterior has just been completed, including a newly painted metal roof, along with a freshly restained rear deck and front porch. Fresh interior paint throughout adds to the bright, polished presentation. Beautifully updated, exceptionally located, and full of character, this special downtown property is truly move-in ready and a must-see! Enjoy extra storage in the clean & dry cellar space featuring solid concrete floors. Contact the listing agent today for more info or your own private showing.

116 E Cork St, Winchester

Listing courtesy of Keller Williams Realty. Contact:

136 Brookland Ct Unit 9, Winchester
$249,900
2 Beds ⋅ 2 Baths
Welcome to easy, low-maintenance living at 136-9 Brookland Court, a stunning top-level condo located in the highly desirable Parkplace Condominiums of Winchester, VA. Brimming with chic vibes, clean finishes, and an abundance of natural light, this updated home boasts a bright, spacious layout with vaulted ceilings. The sunlit living room serves as a captivating centerpiece, featuring skylights, a cozy gas fireplace, an open dining area, and direct access to a private balcony perfect for relaxing outdoors. In the kitchen, cook with style thanks to the airy architectural height and sleek stainless steel appliances. Down the hall, you'll find a bright, spacious primary bedroom that serves as a true retreat, offering a generous walk-in closet and a beautifully updated ensuite primary bath complete with a modern walk-in shower. A second large bedroom highlights charming bay windows, double closets for extra storage, and is served by another updated full bath. Enjoy the ultimate everyday convenience with an in-unit washer and dryer, off-street parking, and an unbeatable location close to schools, shopping, dining, and major commuter routes. Your monthly condo fee provides total peace of mind by covering water and sewer, along with neatly maintained common areas, professional lawn care, snow removal, and trash services. Offering the ideal combination of comfort, style, and low-maintenance convenience, this top-floor residence represents prime Winchester living at its best.

136 Brookland Ct Unit 9, Winchester

Listing courtesy of Colony Realty. Contact:

440 N Braddock St, Winchester
$529,000
An exceptional multifamily investment opportunity awaits in the heart of historic downtown Winchester! Located at 440 N Braddock St, this turnkey property features a timeless brick exterior, rich historic charm, and beautiful hardwood floors throughout. The property comprises three distinct, light-filled units, each designed with two spacious bedrooms and one full bathroom. Tenants will love the shared outdoor living space in the backyard—ideal for relaxing or entertaining—along with the added convenience of a detached garage. Clean, well-maintained, and ready to lease, this prime asset offers outstanding rental potential just steps from the popular downtown walking mall, local dining, shopping, and everything Winchester has to offer. Whether you are expanding your portfolio or looking for a premium income-producing property, this versatile investment is ready for immediate income generation.

440 N Braddock St, Winchester

Listing courtesy of Colony Realty. Contact:

221 Broad Ave, Winchester
$285,000
3 Beds ⋅ 3 Baths
Welcome home! Nestled in a highly convenient Winchester location just minutes from Route 7 and I-81, this property makes commuting and everyday travel a breeze while keeping you close to local shopping and dining. Step inside to find a fresh, modern feel featuring three updated bathrooms (2026). You can move right in with total peace of mind knowing the home also comes equipped with a brand-new HVAC system (2026), a brand-new water heater (2026), and brand-new washer and dryer units (2026) all completely updated for your convenience. Outside, you will love the expansive 0.37-acre lot featuring a large backyard ideal for outdoor activities, alongside a spacious gravel driveway with room to easily park up to four vehicles.

221 Broad Ave, Winchester

Listing courtesy of Keller Williams Realty. Contact:

Homesite 3 Monteith Dr, Winchester
$376,990
3 Beds ⋅ 4 Baths
***OFFERING UP TO $9,500 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
$357,000
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: