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$1,599,000
5 Beds ⋅ 3 Baths ⋅ 73575069 MLS
Set on a generous lot in one of Winchester’s most highly sought-after locations, this stately brick colonial presents a rare opportunity to create your dream home. Offering 2,944 square feet of living space, with high ceilings & oak hardwood flooring. This classic residence has been lovingly enjoyed & maintained by one family and proudly showcases timeless architectural character, generously proportioned rooms, and an abundance of natural light. The inviting front to back living room features a fireplace and serves as a wonderful gathering space, along with formal dining room, eat in kitchen, 1/2 bath plus a sunroom/den and a home office! The upper floors offer 5 spacious bedrooms & provide exceptional flexibility for family, guests, office space, or future customization. Enjoy the rear deck and the vast lot with lush grass, gorgeous perennial gardens and flowering trees offering plenty of space for outdoor entertaining, gardening or expansion. With this home's beautiful brick exterior, classic charm, substantial lot, and premier location, it offers an exceptional opportunity to renovate, reimagine, and create your dream home!

143 Arlington Street, Winchester
$4,299,000
5 Beds ⋅ 6 Baths ⋅ 73574948 MLS
Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully renovated, maintained and updated, blending classic architecture with modern comfort. This 5-bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and relaxed daily living. Water views serve as a serene backdrop to the large modern kitchen, where the natural light dapples and shines all day. It's what everyone craves: the bright, sunny, warm inviting hub of the home. There is an attached mudroom with custom lockers/cabinets, and radiant heat floors. A large family room is attached and is highlighted by a gas-burning fireplace. The expansive living and dining rooms offer plenty of space for more formal entertaining and big groups. One of our favorite features is the study, tucked off the living room and connected to a divine screened-in porch. The natural woodwork and handsome architecture harken to yesteryear while providing the perfect home office and a place to unwind when done working. A generous primary suite is a private retreat with a spacious bath and ample walk-in closets. There are 4 other ample bedrooms, 3 of which are connected to baths, and a second-floor laundry complete this floor. The basement has a huge media and game room, sauna, gym, wine cellar and direct access through a mudroom to a covered patio. Several curated outdoor dining and gathering areas invite entertaining, sunset dinners or quiet reading, overlooking the pond. There is also a full walk-up attic with great ceiling height, unfinished and waiting for your inspiration. An oversized two-car garage with soaring ceilings complete the must-haves. Kayak, skate, go fishing and enjoy life on the water in one of Winchester's most prized, quiet neighborhoods!

4 Dartmouth, Winchester
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 73574928 MLS
Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street, Winchester
$1,299,000
4 Beds ⋅ 2 Baths ⋅ 73574477 MLS
Custom-built and thoughtfully designed for comfortable one-level living, this spacious ranch offers a flexible floor plan, ample living spaces, and convenient access to the walking trails and recreational amenities of nearby Horn Pond. The main level features a gracious formal living room with a wood-burning fireplace, an elegant dining room with custom paneling, and an updated eat-in kitchen with direct access to the picturesque backyard. Three generously sized bedrooms and a full bath complete the main level. Upstairs, a fourth bedroom is complemented by an unfinished storage room with excellent potential for a fifth bedroom, home office, or additional living space.The walkout lower level adds even more flexibility with a family room featuring a second fireplace, half bath, dedicated laundry room, mudroom, and direct access to the oversized two-car garage. Two additional storage areas provide the opportunity to create a home office, gym, playroom, workshop, or finished living space. With substantial square footage throughout, there is plenty of room to adapt the home to your needs. Beautiful custom moldings, well-proportioned rooms, abundant natural light, and a well-designed floor plan add warmth and character throughout. Recent improvements include a new roof, spray foam insulation, updated windows, and newer appliances. Outside, the park-like backyard is a true retreat, highlighted by a spectacular 20' x 40' in-ground pool, patio area, and exceptional privacy while abutting the Lynch School fields. Just moments from the Horn Pond Recreation Area, enjoy convenient access to walking trails, scenic views, playgrounds, fishing, and year-round outdoor recreation. With the newly constructed Lynch Elementary School nearby, along with shopping and major commuting routes, this home offers an ideal blend of privacy, recreation, and everyday convenience.

253 Pond St, Winchester
$2,995,000
5 Beds ⋅ 6 Baths ⋅ 73574330 MLS
A distinctive new construction home where exceptional scale, thoughtful design, and refined finishes come together. Offering approximately 6,500 sq ft of beautifully finished living space, 8 Priscilla Ln was designed to feel impressive yet inviting. Soaring ceilings, graceful archways, and a dramatic two-story living room establish the home's architectural character, while an open, flowing layout is equally suited for everyday living and entertaining. At the heart of the home, the chef's kitchen features custom cabinetry, Thermador appliances, an oversized island, and a spacious walk-in pantry. The primary suite is a true retreat with a spa-inspired bath and generous walk-in closet, while multiple additional bedrooms offer the privacy of en suite baths. Downstairs, ceilings exceeding 10 feet elevate an expansive finished lower level with tremendous flexibility for a media room, gym, au pair or guest accommodations, or additional living space. Designed by Salt and Stone Co. and complete with a two-car garage, this is a home defined by craftsmanship, presence, and details rarely found in new construction.

8 Priscilla Lane, Winchester
$3,149,000
7 Beds ⋅ 8 Baths ⋅ 73573670 MLS
Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by custom built-ins, fine cabinetry and beautiful millwork throughout. The newly renovated chef’s kitchen showcases quartz countertops, an oversized center island, two dishwashers and a butler’s pantry with wine fridge and ice maker, flowing seamlessly into the elegant dining room, living room and fireplaced family room overlooking the meticulously maintained grounds. A dedicated first-floor wing offers incredible flexibility for extended family, au pair or guests, while a private office with custom wet bar and additional spaces can easily accommodate two executive home offices. Upstairs, the grand primary suite is joined by four additional bedroom suites, each offering a private bath, sitting area and generous closet space. The third floor provides a completely private guest or teen suite with a full bath and two closets.The finished lower-level offers media, game and gym areas with a full bath and direct access to the inviting heated pool and lush landscaped grounds. Unmatched in scale and versatility with resort-like amenities, exceptional craftsmanship and a coveted West Side location, this remarkable home offers luxury living at its finest.

37 Mayflower Road, Winchester
$1,650,000
5 Beds ⋅ 4 Baths ⋅ 73573887 MLS
Expansive living and unparalleled curb appeal define this exceptional five-bedroom garrison colonial, ideally positioned near the natural beauty and extensive trails of the Fells Reservation. Set in the highly regarded Muraco Elementary School district, this spacious home offers an inviting blend of timeless architecture, thoughtful updates, and remarkable flexibility for today’s lifestyle. The sun-filled first floor features an open, seamless flow designed for both everyday living and effortless entertaining. A thoughtfully appointed eat-in kitchen with premium Sub-Zero and Fisher & Paykel appliances opens to the dining space, creating an ideal setting for gathering. A wood-burning fireplace anchors the living room where you can watch the world go by from the gorgeous picture window. A home office, mudroom, and powder room add functionality to this level. Upstairs, the generous primary suite includes a full bath and convenient laundry, with tree-top views from the Juliet balcony, complemented by four additional bedrooms and a family bath. A finished walk-up attic provides valuable storage and flexible bonus space, while the finished lower level adds a generous family room and several bonus spaces ideal for a second home office, playroom, media space, or additional recreation area, with kitchenette and full bath allowing for ADU possibilities. Outside, enjoy a truly private retreat with a fully fenced yard and pristine in-ground pool, offering exceptional space for outdoor living, entertaining, and relaxation. A two-car attached garage adds everyday convenience. With generous proportions throughout, multiple flexible spaces, an inviting open floor plan, and close proximity to the Fells Reservation, this Winchester Highlands property offers a rare opportunity to enjoy space, privacy, and sophisticated everyday living in one of Winchester’s desirable neighborhoods.

117 Highland, Winchester
$2,249,000
5 Beds ⋅ 4 Baths ⋅ 73574117 MLS
Built in 2021, this stunning home is ready for its next owners to enjoy. Its elevated setting provides a peaceful retreat with multiple areas for outdoor living, including a charming front porch. Inside, thoughtful design and exceptional attention to detail are evident throughout. The expansive open-concept kitchen, living and dining areas offer an ideal setting for entertaining, complemented by two gas fireplaces and central air. The luxurious primary suite features soaring ceilings, a walk-in closet, spa-like bath and private balcony. Three additional bedrooms offer generous proportions and ample closet space, while a conveniently located laundry room completes the second level. The ground floor provides a flexible living space ideal for guests, an au pair suite, or a recreation room. A whole-house generator offers added peace of mind. Ideally located approximately an equal distance to both Winchester and Arlington centers.

11 Locke St, Winchester
$479,900
3 Beds ⋅ 2 Baths ⋅ 5108720 MLS
Welcome HOME and move right in to this lovely 3 year old 2 story Colonial home!!! New Englander style featuring 3 bedrooms, 2 bathrooms and room for everyone! Enter into the home from your charming farmer's porch into a spacious living room; room for entertaining, movie or game nights and so much more!!! Expansive open concept kitchen and dining boasts fully applianced kitchen, granite countertops, large kitchen island and pantry. Sliders to your 16x12 deck off the dining room lead you to your level back yard where BBQs, yard games and gardening can take place. On the second level of the home you will find your spacious primary bedroom with walk in closet and large full bathroom. 2 additional ample sized bedrooms and laundry area complete the second floor. Close to town and amenities, walk to the town beach and boat launch, easy commute to Keene, Brattleboro and I91. This home is efficient, well built and ready for you. Don't miss the opportunity to make this wonderful home yours!!!

366 Keene Rd, Winchester
$2,199,000
4 Beds ⋅ 4 Baths ⋅ 73572955 MLS
Welcome to 19 Hancock Street, a stunning transformation where timeless New England character meets sophisticated modern living. Completely reimagined through an extensive renovation, this exceptional Winchester residence preserves the charm and presence of a classic home while delivering the design, finishes and functionality expected for today’s lifestyle. The beautifully designed first floor features a bright, open layout with an effortless flow from room to room, creating an ideal setting for both elegant entertaining and comfortable everyday living. Thoughtful details throughout include a spacious pantry and dedicated mudroom, blending style with exceptional functionality. Upstairs, four bedrooms include a luxurious primary suite designed as a private retreat, complete with a beautifully appointed bath and oversized walk-in shower. Convenient second-floor laundry and well-designed secondary bedrooms make this level as practical as it is polished. The finished lower level offers another impressive dimension of living space, perfect for a media room, home gym, playroom, office or guest retreat. With 3.5 beautifully finished baths, a two-car garage, and a rear deck ideal for outdoor dining and entertaining, every level of the home has been thoughtfully considered. All of this is set in one of Winchester’s most convenient locations—just minutes from Winchester Center, the commuter rail, shops, dining and schools. Classic character, completely renewed. Modern luxury without sacrificing warmth. 19 Hancock Street is a rare opportunity to enjoy the best of Winchester living in a home that feels both established and entirely new.

19 Hancock Street, Winchester
$1,749,000
5 Beds ⋅ 4 Baths ⋅ 73572890 MLS
A rare offering in one of Winchester's most desirable neighborhoods, this spacious mid-century contemporary spans approximately 3,500 square feet with 5 bedrooms and 3.5 baths on a private 0.24-acre lot. The open main level flows from a light-filled living room with a cathedral ceiling, stained-glass accents, and a fireplace into the dining room, family room, and a renovated kitchen with Silestone quartz countertops, upgraded cabinetry, and direct deck access. Upstairs, two ensuite bedrooms anchor the floor plan, including a generous primary suite with a large jetted soaking tub, vanity, and walk-in closet. Three additional bedrooms and a family bath complete the level. Hardwood floors run throughout, a second fireplace warms the lower-level bonus room, and ductless mini-splits deliver year-round comfort throughout the house. The walk-out lower level offers a versatile bonus room with its own exterior entrance, ideal for a home office, gym, media room, playroom, or guest suite. Three decks extend the living space outdoors for entertaining and dining above the private backyard, and an attached two-car garage adds everyday ease. Set on a quiet street with easy access to commuter rail, downtown Winchester, parks, and bike or jog trails, this is a rare chance to live in your dream home in a community that has it all.

17 Churchill Rd, Winchester
$1,679,900
3 Beds ⋅ 2 Baths ⋅ 73572791 MLS
Distinctive in both design and craftsmanship, this custom expanded Ranch combines balanced architectural proportions, generous living space, and everyday comfort in Winchester’s highly sought-after East Hill neighborhood. A welcoming foyer with built-in bench opens to warm, light-filled interiors curated to feel both connected and intimate. At the heart of the home, the expansive mahogany kitchen features a substantial wood center island, handmade pocket plantation shutters that disappear seamlessly behind custom cabinetry, updated countertops and backsplash, a concealed illuminated bar cabinet, beverage fridge, and dual-zone wine fridge. Paned-glass pocket doors can separate the kitchen or open it to the adjoining dining and family rooms, where radiant-heated floors create a warm, inviting setting and a wall of windows connects the interior space beautifully to the surrounding landscape. The family room’s custom cherry entertainment center, finished with copper paneling and ebony inlays, reflects the extraordinary attention to detail found throughout. A formal living room with fireplace and custom millwork provides a separate space to gather or unwind. Tucked into a private wing are three well-proportioned bedrooms with hardwood floors and generous closets, along with a renovated full bath featuring a double vanity, deep soaking tub, and radiant-heated floor. The finished lower level offers remarkable flexibility with a media room wired for surround sound, exercise room, second full bath, laundry, mudroom area, abundant temperature-controlled storage, and direct access to an oversized two-car garage with workspace. Outside, the backyard and stone patio provide an equally peaceful and private extension of the interior living space. Mature plantings, stone walls, a potting shed, and an irrigation system complete this wide, one-third-acre lot. Central air, central vacuum, extensive built-ins and storage, plus new interior doors and crown molding throughout the bedroom wing add comfort and convenience. Polished, distinctive, and genuinely inviting, 5 Willowdale Road is a home of enduring quality that feels every bit as special as it looks. NO OPEN HOUSES, shown By Private Appointment only.

5 Willowdale Rd, Winchester
$2,049,000
4 Beds ⋅ 4 Baths ⋅ 73572687 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
$1,699,000
3 Beds ⋅ 2 Baths ⋅ 73572661 MLS
Extensively rebuilt and expanded, this impeccably maintained 3/4 Bed 2 BA home offers a spacious and versatile floor plan. The impressive 28’ x 20’ great room features vaulted ceilings, bay window, and a gas fireplace which flows nicely from the updated kitchen. Step outside to a new oversized Azek deck with plenty of room for grilling, dining, and relaxing. The main level also includes formal living and dining rooms, plus a bedroom & full bath. The formal dining room offers flexibility to serve as a fourth bedroom, if desired. Upstairs are two generously sized bedrooms with hardwood floors and ample closet space, along with a spacious hall bath featuring a skylight. Additional highlights include a finished lower level, laundry and storage areas, and direct access to a two-car garage. Beautifully landscaped grounds feature perennial gardens, flowering trees, natural stone walls, and exceptional privacy—nestled into one of Winchester’s most desired neighborhoods, all just 7 miles from Boston with convenient access to the town center, Fells trails, major routes and highways. Please see feature/ update list attached.

4 Churchill Road, Winchester
$619,000
3 Beds ⋅ 4 Baths ⋅ 73571573 MLS
Great opportunity to live on a quiet side street conveniently located near the town center and Elizabeth C. McDonald Field, featuring tennis courts, ball fields, basketball courts, and a playground. This well-maintained 3-bedroom, 3.5-bath townhouse offers 1,225 sq. ft. of comfortable living space. The charming home features high ceilings and a functional multi-level layout with a bright living area, spacious kitchen, two generously sized bedrooms, and a large office. Numerous updates were completed in 2023, including hardwood flooring, a finished attic, five ductless mini-split AC units, and renovated bathrooms. A new roof was installed in 2024. Additional updates include a high-efficiency gas boiler and hot water system installed in 2019. Conveniently located within walking distance to the newly built Lynch Elementary School and Winchester High School, with easy access to local shops, restaurants, and major routes. A wonderful opportunity to enjoy comfortable living in highly desirable Winchester!

23 Shepard Ct Unit 23, Winchester
$1,099,000
4 Beds ⋅ 3 Baths ⋅ 73571480 MLS
Tucked on a quiet side street just north of Main Street, this circa-1853 antique pairs the character of a classic Winchester home with the space of a beautiful, sun-filled addition (completed in 2003): A lovely farmer's porch welcomes you and, once inside, hardwood and tile floors run through the main living spaces. Front rooms include a quaint sitting room and private office. A gas fireplace adds warmth in the family room off the kitchen, which has a slider out to a generous sized deck overlooking the serene back yard. Fresh paint throughout means there is nothing to do but move in. The same addition brought two bedrooms (primary with en suite bath), a walk-in closet, and updated kitchen cabinetry. Out back, a wood deck steps down to a spacious fenced yard with a built-in tree house, a garden area, storage shed, and in-ground sprinkler system. Central air conditioning, gas heat, town water and sewer, a one-year-old hot water tank, a partially finished, heated basement, a walk-up attic, and a four-car driveway. The location is the real headline: walk to the commuter rail, the bus, and Winchester Center's shops and restaurants, with the park, bikeway, and conservation trails minutes away. Newly renovated Lynch Elementary, McCall Middle and Winchester High School.

24 Richardson St, Winchester
$1,050,000
5 Beds ⋅ 3 Baths ⋅ 73571418 MLS
Situated on a large,10k+ level corner lot with frontage on both Cross Street and Verplast Avenue! The upper level features a fireplaced living room w picture window, updated kitchen, three bedrooms, 1.5 baths, and a large sunroom overlooking the expansive backyard. The first level offers additional flexible living space with a kitchenette, living area, two bedrooms, laundry, and a full bath, providing great potential for an in-law setup, guest space, home offices, or extended living. The generous lot and existing footprint create an ideal opportunity to modernize the home, expand the living space, or explore future possibilities. Put your personal touch on this home and build some great equity! This property is full of potential and ready for its next chapter!

257 Cross Street, Winchester
$325,000
3 Beds ⋅ 1 Baths ⋅ 5107206 MLS
Welcome to this beautifully renovated single-family home featuring 3 bedrooms and thoughtful new updates throughout. This move-in-ready property offers a comfortable and inviting layout, making it an excellent choice for a first-time homebuyer or anyone looking for a great starter home. With its fresh updates and welcoming atmosphere, this home is ready for its next owner to make it their own. Situated across the road from the Ashuelot River come take a look for yourself.

73 Ashuelot Main St, Winchester
$99,000
4 Beds ⋅ 2 Baths ⋅ 5107063 MLS
Opportunity awaits on this .30 acre lot. Currently home to a double wide mobile home that has been completely gutted inside, this property is a blank canvas ready for extensive rehabilitation. Bring your vision and make it your own. A wide variety of possibilities exist here, making it a fantastic option for investors or anyone looking to take on a rewarding project. Location is everything, and this one delivers. Directly across the street, the Ashuelot River offers great kayaking right at your doorstep. The property also backs up to Pisgah State Park, home to thousands of miles of trails across both private and state managed lands, perfect for hiking, biking, and exploring right from your backyard. Outdoor recreation enthusiasts will also love the convenience of the OHRV staging area just down the street, offering easy access for off road adventures. property has a shared well with neighboring property. Seller has never occupied the property. Property is being sold AS IS. This property includes a camper and pickup truck, along with various items left on site, all to be conveyed with the sale at no additional cost. Buyer assumes full responsibility for removal and disposal of these items, which are included strictly on as is basis. no warranties expressed or implied. Buyers are responsible for conducting their own due diligence regarding zoning,shared well, and all other aspects of the property. Don't miss this chance to create something special in a location that offers unbeatable access to nature and recreation.

357 Ashuolet Main St, Winchester
$1,699,000
5 Beds ⋅ 4 Baths ⋅ 73568493 MLS
Built in 2019 and perfectly positioned near downtown Winchester and the commuter rail, this 5 bed, 3.5 bath Colonial offers a bright, open layout with oversized windows, newly installed custom interior shutters and great natural light throughout. The large living room flows into the dining room, making the first floor great for everyday living and entertaining. The kitchen features a 2025 Thermador appliance package and oversized breakfast nook, with access to the deck, patio and fully fenced yard. Exterior work and fencing were completed in 2022, with mature evergreens and the newer fence creating a private and serene outdoor setting. Upstairs, the spacious primary suite includes a walk-in closet and en-suite bath with soaking tub and standing shower. Two additional bedrooms, a Jack-and-Jill bathroom and laundry room complete the second floor, with two more bedrooms and a full bath on the third. Ample storage throughout the home, including custom closets and additional storage tucked under the eaves on the third floor. Solar panels with Tesla Powerwalls and a HEATED DRIVEWAY are great added features. The unfinished basement with 8'+ ceilings offers excellent potential for future living space.

30 Farrow St, Winchester
$650,000
2 Beds ⋅ 2 Baths ⋅ 5106346 MLS
Bring your dreams to life on this sprawling 17.8-acre Winchester property, offering endless opportunities to create the homestead you’ve been waiting for! The 1.75-story log cabin features two bedrooms, two full baths, and a bonus room that could serve as a third bedroom. Vaulted ceilings and a stone fireplace create a warm and inviting living space, while multiple porches spanning three sides of the home provide plenty of room to relax and enjoy the peaceful surroundings. The updated kitchen and first-floor bathroom, first-floor laundry, and full basement are additional features of this well-maintained home. This property offers so much more than just a home. A three-car garage (24x28) with a rear lean-to provides additional storage, while the six-bay shop (22x36) offers plenty of room for vehicles, equipment, and projects, complete with workbench areas and more rear lean-to storage. The two-story barn (30x52) features water and electricity, stalls, and a tack room. Outside, fruit trees are scattered on the front lawn and gardens can be found across landscaped grounds. Up on a knoll behind the house, you’ll find a self-proclaimed “campground,” complete with an RV pole barn (20x36), water access, and multiple electrical hookups. A screen house, wood shed, and fire pit create a perfect gathering space overlooking the field and pond. Whether you’re looking for space for your hobbies, animals, equipment, family, or a private place to make your own, this property offers the space and flexibility to do so. Conveniently located in Winchester, NH, just 20 minutes from Keene, 30 minutes from Brattleboro, VT, and 10 minutes from the Massachusetts border. Realtor is a relative of the seller. Seller has never occupied the property. Buyers to do their own due diligence. Please do not access the property without being accompanied by a licensed agent.

60 Forest Lake Rd, Winchester
$1,098,000
3 Beds ⋅ 2 Baths ⋅ 73566405 MLS
Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a dining area with sliders to a private deck and fully-fenced, tree-lined yard. Upstairs features three bedrooms, including a impressive primary suite with a stunning walk-in closet, and a full bath. Major upgrades include deleading (2018), basement asbestos removal (2019), a newer furnace, and a brand-new water heater (2024). Ideally located just 1 mile from Winchester Center, top schools, dining, and the MBTA commuter rail to Boston! Conveniently located near local schools, with easy access for families.

17 Russell Rd, Winchester
$1,999,000
4 Beds ⋅ 3 Baths ⋅ 73565817 MLS
Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

85 High St, Winchester
$367,500
3 Beds ⋅ 2 Baths ⋅ 5105670 MLS
Step inside this comfortable and thoughtfully updated ranch. With 3 bedrooms, including the primary suite, and 2 baths, this home is designed for easy, enjoyable living with space for all. Enjoy the outdoors from the huge screened-in porch, perfect for relaxing, entertaining, or simply taking in the peaceful surroundings. An additional enclosed porch provides even more flexible living space. The home has been modified for added accessibility, and features newer flooring throughout, along with central A/C for year-round comfort. Peace of mind comes easy with an automatic standby generator, while the vinyl siding and metal roof provide durable, low-maintenance exterior protection. The fenced-in backyard offers a great space for pets, gardening, recreation, or simply enjoying the outdoors. For those who like to tinker, create, or tackle projects, the basement workshop provides valuable dedicated workspace and storage. With its accessible features, comfortable living spaces, durable improvements, and outdoor amenities, this is low-maintenance living at its best. A home where you can spend less time on upkeep and more time enjoying life. Refresh the interior with your own paint colors. Schedule your showing now or visit at your convenience, one of our upcoming open houses 8/22/26 and 8/23/26 from 11:00 A.M. to 2:00 P.M.

10 Burt Hill Rd, Winchester
$349,900
3 Beds ⋅ 2 Baths ⋅ 5105078 MLS
Set along a tranquil road with seamless access to Route 91, Vermont, Massachusetts, and Keene, this inviting single-story ranch rests on an expansive lot, offering an ideal setup for first-time buyers or anyone seeking an easier, simplified lifestyle. Inside, sun-drenched living areas feature classic hardwood floors, rich pine paneling, and broad windows that fill the space with warmth and pleasant scenery. The spacious kitchen is well-equipped with abundant cabinetry, two bright windows, and a multi-functional island peninsula featuring extra prep space on one side and casual seating on the other, while the adjacent dining nook includes a cozy window seat perfect for dining or relaxing with a book. A generously sized full bathroom thoughtfully incorporates laundry facilities alongside custom built-in drawers and storage. For seasonal outdoor enjoyment, the home extends out to a screened porch and a private patio enclosed by brick and stone walls that evoke a hidden garden retreat. Complete with a wood stove connection, an attached two-car garage, and a paved driveway, this charming home is a wonderful opportunity!

88 Back Ashuelot Rd, Winchester
$3,295,000
6 Beds ⋅ 7 Baths ⋅ 73563095 MLS
Introducing 2 Atherton Road, an exceptional new construction residence offering over 6,100 sq. ft. of beautifully designed living space with 6 bedrooms, 6.5 baths, and a 3-car garage. A dramatic entry with soaring ceilings and a striking staircase sets the tone for the home’s sophisticated interiors. Designed for both everyday living and entertaining, the open-concept main level showcases an impressive oversized living and dining space that flows seamlessly into the chef’s kitchen, featuring a Thermador appliance package, wine chiller, wet bar, and custom finishes. The adjoining family room is anchored by an electric fireplace, while a private home office and first-floor guest suite add versatility to the floor plan. Upstairs, four bedrooms each feature private en-suite baths, including a spacious primary retreat with a beautifully appointed bath and oversized custom walk-in closet. The finished lower level expands the living space with a media room ideal for movie nights, an additional bedroom, and full bath. Outdoors, a private fenced backyard and patio create the perfect setting for relaxing and entertaining. Pella windows and thoughtfully selected finishes can be found throughout. Ideally situated in a desirable Winchester neighborhood just down the street from Ambrose Elementary School and moments from downtown Winchester’s restaurants, shops, cafés, and commuter rail service to Boston’s North Station. A sophisticated new construction offering that combines space, style, and an exceptional Winchester location.

2 Atherton Rd, Winchester
$1,329,000
3 Beds ⋅ 3 Baths ⋅ 73562273 MLS
110 Thornberry Road. Strong west side location near Vinson-Owen Elementary School and the Winchester Swim & Tennis Club. An exceptional opportunity to establish roots in Winchester. 2021 Natural Gas Brute FT Floor Standing Boiler. Replacement windows. Central cooling. 200 amp electric. Updated Kitchen w Double oven. Prefinished hardwood floors. Therma-Tru French doors flow from the dining room to a window-lined bonus room off the dining room provides flexible year-round living space. In-ground swimming pool.

110 Thornberry Road, Winchester
$2,499,000
4 Beds ⋅ 5 Baths ⋅ 73555666 MLS
Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with custom built-ins and entertaining bar,formal dining with butler’s pantry, private office,and luxurious primary suite with vaulted ceilings, walk-in closets,and spa bath.Expanded outdoor living features a custom outdoor kitchen,fire pit,and multiple patios designed for exceptional entertaining.The finished lower level offers a bonus room, home gym, mudroom, and oversized 2-car garage.Professionally landscaped with exceptional privacy, yet just moments to the Vinson-Owen School,steps to the Swim & Tennis Club,and major commuter routes.A rare opportunity to own one of Winchester’s finest newer homes. See Video: https://player.vimeo.com/progressive_redirect/playback/1217669935/rendition/1080p/file.mp4%20%281080p%29.mp4?loc=external&log_user=0&signature=65fb6c1e2692e9ac8d5b781ceed13c02239d5128d88af87ce725ce6cd7907704

54 Squire Road, Winchester
$949,999
4 Beds ⋅ 2 Baths ⋅ 73561829 MLS
Discover a rare opportunity to own a versatile ranch in sought-after Winchester, offering flexible living with a two-bedroom main level and a full two-bedroom in-law suite below. The gracious first floor welcomes you with gleaming hardwood floors and a handsome fireplace anchoring the living room. A generously proportioned dining room, complete with a classic built-in china cabinet, opens effortlessly into a bright eat-in kitchen — an inviting space for both everyday living and entertaining. Two well-sized bedrooms with ample closet space and a full bath complete the main level, kept comfortable year-round by central air-conditioning.The lower level offers exceptional flexibility with its own private in-law suite, featuring a warm, fireplaced living room, two bedrooms with plush wall-to-wall carpeting, and a full bath — ideal for extended family, guests, or additional living space.Outside, enjoy a level, easy-to-maintain backyard, convenient off-street parking, and a one-car garage. Ideally located just minutes from Skillings Field and McDonald Field, this home offers wonderful access to local recreation, with Lynch Elementary only 0.8 miles away and the scenic Horn Pond Recreation Area close at hand. Enjoy the convenience of nearby Winchester Hospital, easy access to Route 3, and commuter rail service for a smooth trip into Boston. A home that blends comfort, versatility, and an unbeatable location — a must-see that won't last long. Showings begin 8/22 @ Open House 1:30-3PM

96 Loring Ave, Winchester
$3,450,000
6 Beds ⋅ 5 Baths ⋅ 73561703 MLS
Situated on a generous18,000SF level lot! Must see this custom built spectacular masterpiece by some of winchester's finest builders, offering unique architectural design and dramatic finishes showcasing a fabulous dining room w/ a custom wine wall cabinet, gorgeous kitchen, with high end 48 inch gas range w/double ovens, 48"paneled fridge, 10' island w/ seating & a walk in pantry! Enter from the oversized three car garage into the stunning mudroom & into the most fabulous home that has hit the market in quite some time. Wide plank oak flooring, high ceilings & tasteful finishes throughout. The family room feature wall has custom arched inset bookshelves & cabinetry with led lighting, gas fireplace & plenty of windows to enjoy views of the gorgeous yard. Enjoy conversations & cocktails in the stylish lounge featuring elegant arched details, a custom wet bar & wine fridge. Oversized sliders to spacious deck draw you to the gorgeous 1/2 acre level lot with **room for pool ** pool shown is virtual image*. The first floor also offers a bedroom or home office option; The second floor features 5 large bedrooms & 3 full baths w/ soaring ceilings in every room; the primary being a dreamy retreat showcasing a spa like porcelain bath w 10' shower & 2 shower heads with soaking tub, bidet toilet & walk in closet! Second floor laundry w/sink & custom cabinetry make doing laundry a joy. The lower level offers plenty of space for media room, game room plus space for a home gym & full bath! This exceptional home is a must see ~the top quality finishes and stunning design will not disappoint!

7 Hutchinson Road, Winchester

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