Winchester Real Estate

**Discover Winchester: A Gem in the Heart of Virginia**

Nestled in the picturesque Shenandoah Valley, Winchester, Virginia, is a charming city that beautifully blends rich history with modern living. Known as the "Apple Capital of Virginia," this vibrant community is not only renowned for its bountiful orchards but also for its stunning landscapes, historic architecture, and welcoming atmosphere.

Winchester's history dates back to the 18th century, and the city played a significant role during the Civil War, with many historical sites and museums, including the Museum of the Shenandoah Valley and the historic Old Town, where cobblestone streets are lined with boutique shops, cafes, and art galleries. The lively atmosphere of Old Town Winchester is perfect for leisurely strolls, dining, and enjoying local events, such as the weekly farmer's market and various festivals throughout the year.

The city’s location is ideal for those who enjoy outdoor activities, with nearby access to the Appalachian Trail and the breathtaking Blue Ridge Mountains. Whether you prefer hiking, biking, or simply soaking in the natural beauty, Winchester offers a myriad of recreational opportunities.

Families will appreciate the excellent schools and community programs, while professionals will find that Winchester’s strategic location provides easy access to both Washington D.C. and Northern Virginia, making it a desirable spot for commuters.

With its unique blend of history, culture, and community spirit, Winchester is more than just a place to live; it's a place to thrive. Come experience the warmth and charm of this extraordinary city, where every day feels like a step back in time yet is infused with the energy of modern life. Your dream home awaits in Winchester!

Newest Listings in Winchester

$1,125,000

5 Beds ⋅ 3 Baths ⋅ 73555245 MLS

Elegantly updated, two-family home offers flexibility for multi-generational living, rental income, or as a spacious single-family. Thoughtful renovations preserve the home's original character while adding modern comforts. A charming farmer's porch leads to an inviting patio. The larger side, 8 Oak, features 8 rooms, 4 beds, 1.5 baths, a 2024 eat-in kitchen with timeless cabinetry, quartz countertops, butcher block island, blue-and-white tile backsplash, exterior-vented gas range, and direct access to a 2024 TimberTech deck. Highlights include an inviting living room with embossed tin ceiling, a first-floor bedroom or office with floor-to-ceiling windows, wide-plank floors, a lower level family room that has a full walk-out to back yard, and 3 second-floor bedrooms. The full bath was beautifully renovated in 2020 with vintage-inspired washstand sinks. The unfinished basement includes laundry and ample storage. The apartment, 10 Oak, is a bright 3 rooms, 1 bed, 1 bath featuring original pine floors, a living room with access to deck, an eat-in kitchen, and a second-floor bedroom suite. Both sides feature mini-split heat and A/C. 8 Oak also offers gas baseboard and radiator heat and 10 Oak also has radiator heat. Three off-street parking spaces. Enjoy an unbeatable location just a short walk to Winchester Center, two MBTA Commuter Rail stations (only two stops to North Station), restaurants, cafés, and shops. Located in the sought-after Lynch Elementary School district and Winchester's top-rated school system. This special property blends timeless charm, modern updates, and exceptional versatility.

8-10 Oak St, Winchester

$259,900

3 Beds ⋅ 2 Baths ⋅ 5101665 MLS

TIMELESS FARMHOUSE CHARM: This intimate New England town of Winchester, NH is in the Southwestern corner of NH bordering Massachusetts, Vermont and Interstate 91. It's only a 20 minute ride to the neighboring city of Keene, NH, a 20 minute drive to the town of Brattleboro, VT and 18 miles to Athol, MA. The local recreation can be enjoyed at Pisgah State Park, Forest Lake, the Ashuelot River and the Rail Trail where you will find kayaking, fishing, hiking, ATVing, hunting and plenty more outdoor activities. The Winchester Speedpark, for the racing enthusiast, is a fun attraction along with the Annual Pickle Festival, Music in the Park and The Community Center's events which are enjoyed by All. The previous owners of 65 Mechanic St. resided in their home as a spacious single family but is also configured as a multi-family, multigenerational living or for investors. Inside, generous rooms, handsome flooring, pantries, 3 to possibly 5 bedrooms, 2 attractive updated bathrooms and painting throughout, an enclosed porch and decking create a comfortable and inviting atmosphere. An attached barn/2 car garage, ample parking, plenty of storage and attractive landscaping add character and appeal to this proud home. Located within walking distance to Winchester's town center adds convenience and versatility on its 1.2 acres. This intriguing farmhouse has so many possibilities!! It's waiting to be SOLD and is waiting for you to welcome its next chapter!!

65 Mechanic St, Winchester

$499,900

2 Beds ⋅ 2 Baths ⋅ 5101659 MLS

Set well off the road at the end of a private driveway sits this adorable waterfront home with gorgeous views over Forest Lake! The property features an open concept kitchen/dining/living area overlooking the water, a large deck, screened in porch, 2 ample sized bedrooms plus a full bath to complete the first level. Downstairs offers a bonus bunk room, sitting area, plus bath and laundry. Add in the handy storage shed, plenty of available parking spaces, large .40 acre lot, private dock and beach area on your 103 feet of lake frontage, and you have the total package!

418 Forest Lake Rd, Winchester

$599,000

3 Beds ⋅ 2 Baths ⋅ 5101558 MLS

Rustic charm, warm wood accents and lovely beam ceilings make this true log house feel like HOME. The outdoor space is a dream; situated on 6.32 acres, this property features a charming front porch, large back deck to relax on warm summer nights, spacious yard with fire pit for cold winter nights & smores, walking and ATV trails and your very own Christmas trees growing! Well landscaped with many perennials to enjoy throughout all of the seasons. Inside timeless log home charm meets all of the modern updates and amenities throughout. This 3 bedroom home has so much to offer; the main floor living boasts a spacious living room featuring a stunning fireplace, wide plank pine floors and wood beam ceilings; fully applianced kitchen with brand new appliances, woodburning Crawford cookstove as well as gas stove, plenty of cabinets and a breakfast bar. A first floor office or bedroom, lovely tiled full bathroom and a large sunroom displaying tiled floors and woodstove offer access to the expansive yard through the sliding glass doors. Enjoy access to the attached two car garage complete with a large bonus room; perfect for guests, a game or movie room and so much more! On the second story of the home you will find the primary bedroom presenting a walk in closet and tiled bathroom with walk in shower. Additionally there are 2 more bedrooms that complete the upstairs. Fine quality throughout and attention to detail make this home a true retreat!! Private yet minutes to amenities!

484 Scofield Mountain Rd, Winchester

$2,225,000

4 Beds ⋅ 4 Baths ⋅ 73554545 MLS

Rarely available in one of Winchester’s most desirable neighborhoods, this beautifully maintained Colonial offers the perfect blend of modern comfort and convenience. Set on a quiet cul-de-sac surrounded by historic homes, this late 1990s residence provides newer construction, a thoughtfully designed floor plan and an exceptional location just minutes from Winchester Center, commuter rail, Lincoln Elementary School and the Middlesex Fells Reservation with miles of trails, hiking, running and The Sheepfold dog park. The traditional yet open layout features an updated kitchen, spacious living and dining areas, refreshed baths, fresh paint and updated mechanical systems. A versatile bonus room with a private staircase offers endless possibilities as a home office, media room, guest space, playroom or fitness area. The finished lower level with half bath adds valuable living space. Enjoy outdoor living on the wraparound deck overlooking a private backyard with mature landscaping.

6 Davey Ln, Winchester

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 73554139 MLS

Classic center-entrance Colonial set on a cul-de-sac with a wonderful sense of flow and everyday function. The main level offers formal living and dining rooms, a spacious front-to-back fireplaced family room with first-floor laundry and half bath, plus a bright kitchen with island, dining area, and direct access to the deck. Upstairs, the primary suite includes a walk-in closet and private bath, complemented by three additional bedrooms and a full bath. A two-car under garage connects to the unfinished basement, offering excellent storage and future possibilities. Central air, gas heat, hardwood floors, and a level lot complete this inviting home.

11 Williams Cir, Winchester

$1,599,000

4 Beds ⋅ 4 Baths ⋅ 73554036 MLS

New roof and fresh exterior paint just completed! This move-in-ready 4-bedroom, 2 full bath, 2 half bath home has been thoughtfully updated and meticulously maintained, offering the perfect blend of timeless charm, modern updates, and exceptional outdoor living in one of Winchester's most sought-after neighborhoods. Recent improvements include a brand-new roof, freshly painted exterior, all-new deck railings, a freshly painted finished lower level with brand-new carpeting, and the seller will replace the second-floor HVAC system, providing valuable peace of mind for the next owner. Inside, you'll find sun-filled living spaces, an updated kitchen, generously sized bedrooms, and a versatile finished lower level ideal for a family room, home office, gym, or playroom. The true showstopper is the spectacular backyard retreat. Designed for entertaining and everyday enjoyment, the private outdoor oasis features a heated saltwater pool with a beautiful waterfall, an expansive patio, mature landscaping, and an outdoor entertaining area rough-plumbed for a future outdoor kitchen—making it easy to create the backyard you've always envisioned. Ideally located just minutes from Winchester Center, top-rated schools, shopping, dining, parks, and commuter routes, this is a rare opportunity to own a turnkey home with outstanding updates, exceptional outdoor amenities, and an unbeatable Winchester location.

241 Ridge St, Winchester

$849,000

3 Beds ⋅ 2 Baths ⋅ 73553626 MLS

Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and effortless entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or a dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester Center commuter rail, and major routes, this home embodies the very best of Winchester living. No HOA fee.

15 Clark St Unit 15, Winchester

$700,000

2 Beds ⋅ 2 Baths ⋅ 73553517 MLS ⋅ ['Wedgewood Place'] BLDG.

Great layout and numerous recent improvements make this a wonderful opportunity! Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER for improved energy efficiency and beauty. Kitchen features updated appliances, granite counters with an eating bar and pantry closet; open to living room with fireplace and dining room with new chandelier. Spacious primary bedroom has LARGE WALK-IN CLOSET plus a sink and linen closet before the entry to the water closet where you'll find a large tub. Second bedroom/office has double closet and is across hall from IN-UNIT LAUNDRY and SECOND BATH with shower. Throughout, enjoy CENTRAL AIR and find NEW LIGHT FIXTURES, FRESH PAINT THROUGHOUT, NEW VINYL "WOOD" FLOORING (all recently done in 2026), NEW WASHER AND DRYER 2025 and NEW HOT WATER HEATER (2024). Love the COVERED PARKING in the garage below the building, association POOL, two ELEVATORS plus the convenience of being only one flight of stairs up from the street level. Location near town center, TRAIN, shopping, restaurants, schools and library is superb.

666 Main Unit 211, Winchester

$1,099,000

5 Beds ⋅ 3 Baths ⋅ 73553083 MLS

Exceptional two-family opportunity with incredible potential to renovate/expand! Situated on a large, level corner lot with frontage on both Cross Street and Verplast Avenue, this property offers endless possibilities for investors, builders, or owner-occupants. The first-floor unit features a fireplaced living room, an updated kitchen, three bedrooms, 1.5 baths and sunroom overlooking the expansive backyard. The second unit offers a spacious and flexible layout with a living room, kitchen, 2 bedrooms, laundry room and full bath. The generous lot, separate entrances, and existing footprint create an ideal opportunity to modernize the current two-family, expand the living space, or explore redevelopment possibilities. Whether you're looking for a strong income property or your next renovation project, this property is full of potential and ready for its next chapter!

257 Cross St, Winchester

$1,750,000

3 Beds ⋅ 3 Baths ⋅ 73551306 MLS ⋅ ['Graystone At Winchester'] BLDG.

OFFER ACCEPTED-OH CANCELLED!Discover luxury & convenience in this impeccably maintained 2-3 bed, 2.5-baths unit in desirable Graystone!! A high end townhome community located just outside Winchester center offering a 1st floor primary suite! The gourmet kitchen showcases custom cabinetry, granite countertops, top-of-the-line stainless appliances w/new gas stove. The open-concept living & dining area w/ a gas fireplace, gleaming hardwood floors & soaring cathedral ceilings w/ skylights, leading to a private, deck & yard—perfect for outdoor relaxation. The spacious first-floor primary suite offers a marble bathroom w/ a custom walk-in shower & generous closet space. Upstairs, the spacious second bedroom, full bath plus an oversized loft family room area w/ potential to wall off a portion for 3rd bedroom, & a cozy a den/ office The walkout LL has high ceilings & offers opportunity to finish 1440SF for gym/rec room, media room, storage or anything you desire!

18 Graystone Circle Unit 18, Winchester

$120,000

2 Beds ⋅ 2 Baths ⋅ 5100353 MLS

Discover comfortable, easy living in this well-maintained mobile home, perfectly situated at the end of a peaceful, low-traffic street. With a thoughtful layout, appealing outdoor space. Two Spacious Bedrooms, are both generously sized, with the primary suite featuring its own full bathroom for added privacy and convenience. The kitchen, dining, and living room flow together seamlessly, creating a bright, comfortable space that’s perfect for both daily living and entertaining. The fenced-In yard is ideal for pets, gardening, or simply enjoying a private outdoor area. Step outside onto your deck a great spot for morning coffee, evening gatherings, or unwinding in the fresh air.

12 Wetherby Dr, Winchester

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