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$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
$950,000
3 Beds ⋅ 1 Baths ⋅ 73549935 MLS
Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds convenience and additional storage, and a half bath is located in the unfinished basement. Just 1 mile from Winchester Center, enjoy easy access to restaurants, coffee shops, boutiques, the public library, and commuter options with close proximity to Boston. The recently built elementary school and renovated high school feature state-of-the-art facilities. Nearby Horn Pond offers scenic walking trails, kayaking, birdwatching, and waterfront views.

47 Water Street, Winchester
$1,699,000
3 Beds ⋅ 4 Baths ⋅ 73549106 MLS
Beautifully updated & impeccably maintained 3 BR, 3.5 bath home on a sought-after cul-de-sac w/lovely front & side yards, abutting conservation land for exceptional privacy. The main level features a spacious living room, updated sunroom, granite kitchen w/newer SS appliances, abundant cabinetry, peninsula seating, & dining room w/ access to an inviting deck. Two 1st floor bedrooms & two full baths, including an en-suite, offer exceptional flexibility. The 2nd floor primary suite is a private retreat w/ a vaulted ceiling, oversized walk-in closet, spacious bath w/ double vanity. This level offers an additional storage closet & unfinished room w/expansion potential. En-suite bedrooms on both the 1st & 2nd floors provide a versatile floor plan. The bright walk-out lower level includes a large family room w/ access to an expansive deck, mudroom, laundry room, half bath, & bonus room ideal for overnight guests. Replacement windows & beautiful storage shed complete this move in ready home.

2 Olde Lyme Road, Winchester
$2,999,000
5 Beds ⋅ 4 Baths ⋅ 73548103 MLS
Must see this stunning move in ready waterfront gem! Perfectly sited at the end of Wedgemere on Winter Pond, offering over 80 feet of direct water frontage w/ expansive yard and breathtaking views from nearly every room. Located in the exclusive Flats neighborhood, this home presents a rare opportunity to enjoy water activities such as kayaking, paddle-boarding, fishing, ice skating and hockey all while being just minutes from Winchester Center and the train to Boston; homes like this rarely come to market. Custom designed and lovingly owned by the original family, this home is now ready for its next chapter. Offering a beautiful flowing layout w/ gleaming hardwood floors, large rooms, featuring floor-to-ceiling bay windows with stunning views, 5 bedrooms, 2 full & 2 half baths, 4 fireplaces, a walk-out lower level rec room, & a gorgeous fenced yard with steps to the water. Truly a special setting that seamlessly combines privacy, views & accessibility in Winchesters TOP neighborhood!

10 Dartmouth Street, Winchester
$1,064,000
4 Beds ⋅ 2 Baths ⋅ 73547513 MLS
Welcome to this meticulously renovated four-bedroom Colonial, ideally situated on a quiet dead-end street just steps from downtown Winchester, the commuter rail, and the newly built Lynch Elementary School. The sun-filled first floor features gorgeous floors, a charming living room, a dining room that opens to a spacious deck, a stunning updated kitchen with new countertops and appliances, as well as a mudroom and a full bath. The fenced backyard is perfect for entertaining. Upstairs, four bedrooms each offer generous closet space. The lower level--with new half bath, new carpet, laundry and storage--is ideal for a media space or playroom. Newer roof, tankless water heater, and a new 200-amp electrical panel provide peace of mind. Close proximity to Horn Pond Reservation, trails, and parks, and easy access to Boston via rail and bus. A rare chance to own a fully updated home in a truly special neighborhood.

46 Clark St, Winchester
$1,899,000
5 Beds ⋅ 4 Baths ⋅ 73545952 MLS
Sophisticated and comfortable, this updated Colonial offers beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level features hardwood floors, elegant architectural details and thoughtfully updated spaces. At the center of the home is a spacious eat-in kitchen with island, abundant prep space, and seamless access to the patio and private backyard. A formal dining room, oversized fireplaced living room, first-floor bedroom, mudroom, and half bath provide both functionality and flexibility. Upstairs are two impressive primary suites with cathedral ceilings, walk-in closets, and private baths, along with two additional bedrooms, full bath, and laundry room. The finished lower level includes a spacious family room with fireplace and ample storage. An attached 2-car garage and a convenient location just minutes to Winchester Center’s vibrant shops, restaurants, commuter rail, and major routes.

79 Grove St, Winchester
$324,900
2 Beds ⋅ 1 Baths ⋅ 5098523 MLS
Welcome home to Ashuelot Road! Enjoy your quiet, extremely well-maintained river front home for many years to come. Just steps from the Ashuelot river and rail trail, this home is perfect for anyone seeking rest and relaxation from the busy days life brings. Featuring a brand new metal roof, as well as a brand new composite back deck and front entry way, you will never have to worry about exterior maintenance again. Inside you'll find a bright open concept living room and eat-in kitchen, along with one full bathroom and 2 spacious bedrooms. Many of the windows are also brand new, including the slider that leads to the new back deck. The dry walkout basement and framed walkup attic are ready for your dreams and design, which will allow for easy expansion of the living space in this beautiful cape. Don't miss out on your chance to own a TURN KEY riverfront home today!

229 Back Ashuelot Rd, Winchester
$2,500,000
5 Beds ⋅ 3 Baths ⋅ 73544924 MLS
Welcome to 9 Plymouth Rd — a classic 1959 single-family home tucked at the end of a private road on a dead-end street, set on a private 0.52-acre lot abutting conservation land in one of Winchester's most sought-after neighborhoods. This well-appointed 11-room residence offers 5 bedrooms, 3 full baths, and 1 half bath, giving your family room to spread out and settle in. Thoughtfully updated for year-round comfort, the home features central AC, central humidification, and an air exchanger. Outside, enjoy beautifully landscaped gardens, a spacious deck overlooking the private yard, lush irrigated grounds with an invisible dog fence, and a hot tub for unwinding after a long day. A wood-burning fireplace adds warmth and character to the living space. Located just minutes from top-rated schools, Winchester Center, and convenient commuter access to Boston, this is a rare opportunity to enjoy privacy, nature, and timeless New England living in an exceptional location.

9 Plymouth Rd, Winchester
$888,000
4 Beds ⋅ 2 Baths ⋅ 73542597 MLS
Charming and Spacious Custom Built Mid-Century Bungalow offers a wonderful opportunity to live in Winchester ! Do you want to send your children to the award-winning public schools? Need an in-law? Generously sized, sun-drenched, freshly painted rooms with hardwood floors and beautiful architectural details, and two fireplaces. A terrific, flat backyard perfect for growing gardens and outdoor fun. A fully finished lower-level creates excellent 2nd living space for your needs. In-town location convenient to the Commuter Rail and all picturesque downtown Winchester offers. Come see all this sweet, unspoiled Mid-Century home on a dead-end street!

84 Oak Street, Winchester
$445,000
3 Beds ⋅ 2 Baths ⋅ 5096976 MLS
This year-round lakefront retreat offers 100 feet of shoreline on Forest Lake and combines comfort, character, and stunning water views. Relax on the enclosed porch or one of several decks while enjoying the peaceful lakeside setting. The open-concept living and dining area features a pellet stove and abundant windows that capture beautiful lake views throughout the seasons. Outdoor living takes center stage, whether you're enjoying your morning coffee on the porch, entertaining on the decks, or spending the day on the water. A separate mobile home that has not been used for some time and could potentially serve as a guest cottage or private accommodation for family and visitors. It includes a living room, kitchen with pantry, bedroom, bathroom, attached shed, its own septic system, and a wood stove ready for hookup. Whether you're seeking a year-round residence, vacation getaway, or a property with space for extended family and guests, this unique waterfront offering provides the perfect blend of tranquility, recreation, and lakeside living.

71 Headlands Rd, Winchester
$1,350,000
4 Beds ⋅ 3 Baths ⋅ 73541775 MLS
Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The inviting living room is enhanced by a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast bar island, laundry, and steps out to the deck and fully fenced, private backyard. A versatile main level bedroom provides direct access to the first of three full bathrooms, while the primary suite on the second level offers a walk-in closet and an updated bathroom with a dual sink vanity and tiled shower. French doors open to the inviting family room with a bay window. Set on a large corner lot with two driveways and a detached two-car garage accessed from quiet Englewood Road, this home offers a prime location moments from the Fells Reservation, the town center, commuter rail, and Muraco ES.

423 Washington St, Winchester
$999,900
4 Beds ⋅ 2 Baths ⋅ 73541288 MLS
A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown

258 Cross Street, Winchester
$2,300,000
4 Beds ⋅ 5 Baths ⋅ 73541163 MLS
Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living & dinning area with a family room. 2nd floor featuring (3) main bedroom with full baths suites. The stunning finished lower level includes a custom wine cellar and recreation area, and flexible rooms perfect for a home office, gym, media room, or guest accommodations.. Ideally located just minutes from Winchester's highly rated schools, town center, parks, dining, and commuter routes. Move-in ready and thoughtfully redesigned for modern living—this is a rare opportunity in one of Winchester's most sought-after neighborhoods.

14 Hillside Ave, Winchester
$1,099,000
3 Beds ⋅ 2 Baths ⋅ 73530959 MLS
Charming colonial with lots of character! Step into a welcoming foyer that leads into an open concept kitchen and dining room area. Kitchen is fully equipped along with gas cooking and breakfast bar,front to back living room with a cozy fireplace surrounded by built-ins and slider out to a big sunny deck and crown moldings, french doors from living room lead out to a 4 season sun room perfect for den, home office or playroom area. First floor half bath. Upstairs features 3 well proportioned bedrooms and a full bath, hardwood floors throughout, partially finished basement with bonus room, 2 car garage and ample driveway parking, sunny back yard. Freshly painted exterior,Showings delayed until Tenant moves out. Please schedule starting July 2nd.

150 Cambridge Street, Winchester
$1,675,000
5 Beds ⋅ 4 Baths ⋅ 73538393 MLS
Excellent New Price! Classic curb appeal abounds at this expansive five-bedroom colonial in the desirable Winchester Highlands neighborhood. The sun-filled first floor features a gracious floor plan with a thoughtfully designed eat-in kitchen showcasing premium appliances including a Sub-Zero refrigerator and Fisher & Paykel DishDrawer. A dining room, living room with wood-burning fireplace, office, mudroom and powder room complete this level. Upstairs, the generous primary suite includes full bath and convenient laundry and is complemented by four additional bedrooms and a family bath. A walk-up attic provides flexible bonus space and storage, while the finished lower level offers a spacious family room, bonus room, and kitchenette with ADU potential. Enjoy the private backyard retreat complete with a fully fenced yard and pristine in-ground pool, plus two-car attached garage. An extraordinary opportunity to enjoy space, comfort, and refined living in one of Winchester’s most sought-after neighborhoods, a short stroll to the incredible nature at the Fells Reservation.

117 Highland Ave, Winchester
$2,099,000
4 Beds ⋅ 4 Baths ⋅ 73538052 MLS
Thoughtfully reimagined with a designer’s eye, this beautifully renovated 4 bed, 3.5 bath home delivers refined living across 3 finished levels. Elevated finishes, including custom tile work, white oak flooring, & curated lighting set this home apart from the typical renovation. The heart of the home is a beautifully designed kitchen with an oversized island & seamless connection to the surrounding living spaces. A formal living room with fireplace, spacious den, sun-filled dining area, & inviting sunroom create an ideal layout for both everyday living & entertaining, while a first-floor bedroom & full bath offer flexibility for guests, or home office. Upstairs includes three spacious bedrooms, including a serene primary suite with spa-like bath & dual walk-in closets, plus second-floor laundry. The finished lower level expands your living space with room for a gym, playroom, or media retreat, complete with a half bath & mudroom. A turnkey home designed to fit the way you live today

26 N Gateway, Winchester
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 73537786 MLS
Lovingly maintained by the same family for more than 50 years, 38 Robinhood is filled with warmth and ready for its next chapter. This versatile home offers a flexible layout with a fireplaced family room, playroom, bedroom, or home office on the entry level, along with a half bath, laundry area, and direct access to the two-car garage. Upstairs, the sun-drenched living room flows into the open dining area with direct access to the oversized screened porch—perfect for relaxing or entertaining. The eat-in kitchen provides access to the patio and backyard, ideal for summer cookouts. The top floor also features three bedrooms with hardwood floors, a full bath, and a half bath. Conveniently located with easy access to all that Winchester has to offer, this cherished home is not to be missed.

38 Robinhood Rd, Winchester
$1,925,000
4 Beds ⋅ 4 Baths ⋅ 73537676 MLS
Set back on a private, serene lot, this contemporary home offers peaceful nature views from nearly every window and a bright, open layout designed for effortless indoor-outdoor living. Cathedral ceilings, hardwood floors, two fireplaces, and French doors create inviting living and dining spaces that extend to decks and patios. The kitchen features teak cabinetry, stone counters, stainless appliances, an island, and a sunny window seat. A main-level primary suite with deck access, two walk-in closets, and a spa-like bath provides a calm retreat. Additional bedrooms offer flexibility for rest, work, or guests, while the full walk-out unfinished lower level—with abundant windows and slider—adds exceptional potential for an ADU, future living area, studio, or recreation space. Updated efficient heat pump heating and cooling, an oversized attached garage, professional landscaping, stone walls, sprinklers, and a cul-de-sac setting complete this distinctive property.

15 Fieldstone Dr, Winchester
$425,000
1 Beds ⋅ 1 Baths ⋅ 5095024 MLS
Presently a contractor who has experience with caring for log homes is applying a special power wash to the main home here. Are you a company boss, family or a fun loving person or one who just wants to relax and enjoy your own RIVERFRONT? These 2 buildings & the open yard can provide room for MANY to stay overnight & enjoy dinners & indoor & outdoor fun. You have been putting in key words as you search for a special property. "log home, my own river waterfront, kayaking, fishing, privacy, guest house or art studio, garage, garden areas, nearby hiking and snowmobiling,year round fun" ...Well here you are! This delightful log home has an open concept first floor with many windows to the yard , beautiful pine floors, a spacious bathroom with a large shower a large bedroom on the second floor. the water view side of the first floor could be enclosed for a bedroom. It has BBHW oil heat. NH Fish and Game stocks the river with fish. Close by are hiking and snowmobile trails (Ashuelot) bridge . Pisgah Park is nearby. You can kayak to Town from your yard along the Ashuelot River.. Enjoy the pavilion picnic place overlooking the river. Across the lawn is the guest house (cabin or art studio) built in 2012. The first floor is open concept and the second floor has a bathroom, the walls have been insulated, there is electric heat but one might add a mini-split for winter use. You can sit on the deck and relish the river view. The river side front yard gets lots of afternoon sun on a good day. The paved driveway leads to the 2 car garage for vehicles and boat storage, a newer roof and just a few steps to the 8x6 mudroom into the kitchen/living area. If you want privacy but still want a few friendly area neighbors the Back Ashuelot Rd. area is for you! Just off Rte.10 it is a short drive to Rte. 91 and picturesque routes to Eastern Massachusetts, and sbout 30 minutes to Keene,NH or Brattleboro,Vt. less than a half hour to Keene and to Brattleboro.

253 Back Ashuelot Rd, Winchester
$3,199,000
5 Beds ⋅ 5 Baths ⋅ 73535697 MLS
Exceptionally rare 1911 property, fully renovated on prestigious Rangeley Road, steps to town. Set on what is widely regarded as the most iconic street in Winchester, this 5 bedroom, 4.5 bath home captures the essence of the coveted Rangeley Estates lifestyle. Over 7,300 sq ft of total space & architectural character, blending classic design with modern luxury. Grand, sun drenched interiors & a beautifully scaled layout offer multiple living spaces, including a 1st floor office. The Chef’s kitchen opens to a dramatic family room with soaring ceilings and French doors leading to outdoor living. The large finished lower level features a spa style bathroom & a beautiful custom wine cellar. An elegant porch & stone paved half moon driveway, enhance the home’s presence, complemented by a 2-car garage and expansive driveway. Moments to Winchester center, Commuter rail, boutiques, dining and Top-rated schools. Private, discreet, an ideal home setting for an exceptional family living!

10 Rangeley Road, Winchester
$129,000
3 Beds ⋅ 1 Baths ⋅ 5094108 MLS
Calling all renovators, dreamers, and HGTV enthusiasts! If you've been looking for a project with great bones and an even better location, 190 Ashuelot Street might be the one. Nestled on 1.4 acres and directly abutting the Ashuelot Rail Trail, this 3-bedroom, 1-bath home is ready for its next chapter. Inside you'll find a large country kitchen, plenty of space to reimagine, and loads of potential. Outside, mature flowering and fruit trees add charm to the yard, while the detached 2-car garage provides room for vehicles, toys, or your next workshop project. Love the outdoors? Step right onto the Rail Trail for walking, biking, snowmobiling, and year-round adventure. Bring your vision, your toolbox, and a little elbow grease—this diamond in the rough is waiting to shine again! Property is being sold as-is. Cash Buyers Only.

190 Ashuelot St, Winchester
$425,000
1 Beds ⋅ 2 Baths ⋅ 5093714 MLS
2007 EXPANDABLE CAPE! A lovely, lovely home to begin with, plus the entire 2nd floor open to expansion, already plumbed and wired with layout for 2BR's and full bath with full shed dormer. On 7.5 acres with privacy and views to distant hills, you will not want to leave this serene home. It is a sanctuary. Plenty of wildlife viewing in your front yard. Inside is a welcoming single level layout with 2 baths, open concept LR/DR/KIT area and a main bedroom with walk-in closet. Hickory cabinetry in the cooks kitchen with a Viking gas range anchoring the space is ready for all your cooking adventures. A walk-in pantry makes meal prep easy and has plenty of room for canned goods and your seldom used appliances. The full basement is high and dry with ample room for workshop, family room or storage. There really is nothing not to like about this home! Close to state park, snow mobile and walking trails.

152 Old Chesterfield Rd, Winchester
$599,000
3 Beds ⋅ 2 Baths ⋅ 5093291 MLS
Brand-new construction offering the perfect blend of modern design, comfort, and future potential. Set on 1.16 acres on a town-maintained dead-end road, this thoughtfully designed 3-bedroom, 2-bath ranch provides easy one-level living with room to grow. Inside, you'll find a bright open-concept layout featuring durable flooring, recessed lighting, and abundant natural light. The spacious kitchen is the heart of the home, complete with an oversized center island, stainless steel appliances, ample cabinetry, and generous counter space. It flows seamlessly into the dining and living areas, creating an ideal space for everyday living and entertaining. The primary suite offers a private retreat with a double vanity, step-in shower, and ample closet space. Two additional bedrooms and a second full bath provide flexibility for family, guests, or a home office. A dedicated laundry room with built-in cabinetry adds convenience and extra storage. One of the home's standout features is the expansive covered rear deck, perfect for morning coffee, outdoor dining, entertaining, or simply enjoying the peaceful hillside setting. The attached two-car garage provides direct access and additional storage. The full walkout lower level offers outstanding expansion potential. With excellent ceiling height, natural light, exterior access, and framing already in place, it presents the opportunity to nearly double the home's usable living space. Whether you envision a family room, gym, guest suite, workshop, or recreation area, the possibilities are endless. Modern mechanical systems, quality craftsmanship, and the peace of mind that comes with new construction make this a low-maintenance home for years to come. Whether you're a first-time buyer, seeking one-level living, or looking for future expansion opportunities, this move-in-ready home delivers exceptional value without the wait.

49 Old Mtn Turnpike Rd, Winchester
$479,900
3 Beds ⋅ 2 Baths ⋅ 5092617 MLS
** OPEN HOUSE SATURDAY, JULY 25 FROM 10AM-12PM** Welcome to 166 Keene Road in Winchester, a charming 3-bedroom, 1.5-bath New Englander that combines classic character with thoughtful modern updates. This inviting home offers comfortable living spaces, abundant natural light, and a warm atmosphere that immediately feels like home. Recent improvements include an updated roof, solar panels for enhanced energy efficiency, a spacious back deck ideal for entertaining and outdoor enjoyment, fresh paint throughout the interior, updated light fixtures, and a new dishwasher, allowing the next owner to move in with confidence. The functional floor plan provides flexibility for everyday living, whether you're gathering with family, working from home, or hosting friends. Outside, enjoy the benefits of outdoor living from the rear deck or wrap around front porch, perfect for summer barbecues, morning coffee, or simply relaxing while taking in the surroundings. The solar system helps reduce energy costs while adding long-term value and sustainability. 465' of frontage on Ashuelot River. Conveniently located with easy access to local amenities, schools, shopping, dining, and recreational opportunities, this property offers the perfect balance of small-town New Hampshire living and modern convenience. Easy commute to Keene, Mass, Brattleboro and Interstate 91.

166 Keene Rd, Winchester

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