Refine Search
Map
Sort by
25 Arlington St, Winchester
$1,400,000
4 Beds ⋅ 4 Baths ⋅ 73584817 MLS
An exceptional opportunity in one of Winchester’s most desirable neighborhoods, directly across from the Winchester Country Club. Set on a beautiful .39-acre lot, this distinctive 4-bedroom, 3.5-bath Colonial offers approximately 2,709 sq. ft. of living space, a 2-cargarage, generous room proportions, and a flexible floor plan ready for its next chapter. Offering wonderful possibilities with its generous proportions, flexible floor plan, and impressive setting, the property presents an ideal canvas for buyers looking to renovate and personalize a home to their exact vision. Reimagine the existing spaces with sophisticated modern finishes, create a timeless renovation that complements the home’s character, or explore the possibilities for a more extensive transformation. The spacious lot also provides plenty of room to enhance the outdoor experience with thoughtfully designed landscaping, gardens, patios, entertaining areas, or other outdoor amenities. Beyond the property itself, the location stands out, with the Winchester Country Club just across the street and downtown Winchester conveniently nearby, offering restaurants, cafés, shops, services, and commuter rail access to Boston. Convenient access to Winchester public schools, major routes, and nearby public transportation makes commuting and exploring the Greater Boston area easy. Bring your architect, contractor, and creativity and transform this property into something truly special. With its substantial lot, desirable neighborhood setting, proximity to downtown, and access to everything Winchester has to offer, 25 Arlington Street presents a rare chance to create a home that reflects your own style in an exceptional location.

25 Arlington St, Winchester

Listing courtesy of Listing Agent: Domingo Medina from Listing Office: Coldwell Banker Realty - Lexington.
200 Swanton St Unit 630, Winchester
$2,100
1 Beds ⋅ 1 Baths ⋅ 73584254 MLS
Sunny, freshly painted one-bedroom condo in Winchester’s Parkview community with a renovated bathroom and all utilities included! Enjoy a bright living area, private balcony, and one bedroom with a full bath. This sixth-floor unit offers convenient elevator access. Community amenities include a swimming pool, two on-site laundry rooms, and visitor parking. Parking for one car is included, with an additional parking pass available for purchase through the HOA. Conveniently located near Winchester Center’s shops, restaurants, cafés, and commuter rail, with easy access to major highways.

200 Swanton St Unit 630, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.
666 Main Street Unit 210, Winchester
$3,200
2 Beds ⋅ 2 Baths ⋅ 73579895 MLS
Welcome to 666 Main Street, offering comfortable, low-maintenance living in a convenient Winchester location! This spacious 2-bedroom, 2-bath residence features hardwood floors, newly updated bathrooms, and a bright, well-designed layout. The primary bedroom offers a generous walk-in closet and private bath, while the living room opens directly to a private patio—perfect for morning coffee or relaxing at the end of the day. Additional conveniences include an in-unit washer and dryer and two parking spaces—one assigned garage space (#2) plus one outdoor space, fireplace, extra storage. Residents also enjoy access to the association’s swimming pool. Rent includes HOA fees, grounds maintenance, snow removal, and trash removal. Centrally located with easy access to grocery shopping, public transportation, schools, downtown Winchester, restaurants, shops, and the commuter rail. A wonderful opportunity to enjoy Winchester living with everyday conveniences close by!

666 Main Street Unit 210, Winchester

Listing courtesy of Listing Agent: Robert Ellington from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
200 Swanton St Unit T14, Winchester
$315,000
1 Beds ⋅ 1 Baths ⋅ 73580409 MLS ⋅ ['Parkview'] BLDG.
Best Price 1 Bedroom at The Parkview in Winchester! An exceptional opportunity to own in Winchester at an accessible price point! This first-floor, one-bedroom Terrace level at The Parkview offers an unbeatable combination of convenience, affordability, and practical living. Positioned on the ground level for easy direct access, the unit features peaceful views of the scenic duck ponds and mature, green landscaping. Step inside to an efficient open-concept layout where the kitchen features a functional peninsula and brand-new, never-used stainless steel appliances. All inclusive monthly HOA fee. Perfect for budget-conscious buyers, investors, or downsizers, completely covers your major monthly utility expenses: heat, hot water, electricity, water/sewer, and central air conditioning. In an era of rising utility costs, this structure provides total peace of mind and simplified monthly budgeting. Residents also enjoy access to the community pool, outdoor picnic grounds, and ample open parking. The location provides premium convenience, situated just minutes from vibrant Winchester Center with its local shops, cafes, highly rated restaurants, and two MBTA commuter rail stations for a straightforward commute. Enjoy everything Winchester has to offer, from the acclaimed public school system to the nearby trails of the Middlesex Fells Reservation, alongside quick access to Route 3 and I-93. If you have been searching for a smart entry into a high-demand market or a turn-key rental property with highly predictable expenses, this unit delivers outstanding utility and location for the price. ~DIRECTIONS TO UNIT~ park in lot to the right and walk to the rear of the building (the part with the duck ponds) it is a terrace level with its own door unit T-14

200 Swanton St Unit T14, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
11 Locke St, Winchester
$2,266,000
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

Listing courtesy of Listing Agent: Lesley Smith from Listing Office: Barrett Sotheby's International Realty.
2 Atherton Rd, Winchester
$3,000,000
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

Listing courtesy of Listing Agent: Peter Kasseris from Listing Office: Serhant.
20 Sargent Rd, Winchester
$1,430,000
3 Beds ⋅ 3 Baths ⋅ 73562422 MLS
Classic East Hill center-entrance Colonial offered for the first time in decades, blending timeless character with gracious everyday living. The front-to-back living room features a beamed ceiling and gas fireplace, creating a warm and inviting gathering space. The dining room is accented by built-in china cabinets, while the eat-in kitchen offers stone counters, stainless steel appliances, recessed lighting, and access to a delightful three-season enclosed porch with cathedral ceiling, skylights, and jalousie windows. A main-level office with windows on three sides and a half bath add flexibility. Upstairs, the primary suite includes a private bath, sitting room, and laundry, complemented by two additional bedrooms and a full bath. A large deck, beautifully maintained yard, central air, and two-car detached garage complete this special East Hill home.

20 Sargent Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
84 Oak Street, Winchester
$760,000
4 Beds ⋅ 2 Baths ⋅ 73542597 MLS
$5000 Closing Costs Credit to Buyer closing by Oct. 31st. Best Value in Winchester! Charming and Spacious Custom Built Mid-Century Bungalow offers a terrific opportunity to live in Winchester! Do you want to send your children to the award-winning public schools? Need an in-law apt.? Generously sized, sun-drenched, freshly painted rooms with high ceilings and hardwood floors, beautiful architectural details, and two fireplaces. A private, 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 Boston Commuter Rail and all picturesque downtown Winchester offers. Come See this sweet, unspoiled Mid-Century home on a dead-end street!

84 Oak Street, Winchester

Listing courtesy of Listing Agent: John E. Magazzu from Listing Office: Charlesgate Realty Group LLC.
23 Stone Ave., Winchester
$1,135,000
3 Beds ⋅ 1 Baths ⋅ 73581744 MLS
Storybook charm meets relaxed, easy living in this inviting Winchester Colonial, ideally located near the natural beauty of the Fells Reservation, Muraco Elementary, and convenient commuter routes. Set on a lovely lot with mature plantings, the property offers a private-feeling outdoor setting, a detached two-car garage, and pretty, original architectural details throughout. Inside, natural light fills the freshly painted interior. The fireplaced living room with wood stove flows seamlessly into the updated kitchen and dining room, creating an easy connection for everyday living and entertaining. The dining room opens to a bright, welcoming sunroom - an ideal spot for morning coffee, reading, or enjoying views of the surrounding yard. Upstairs, two generously sized bedrooms are joined by a third bedroom with a walk-up to additional attic storage, and a charming full bath. The lower level provides even more versatility with a finished bonus room, laundry, plentiful storage and exterior access. Thoughtfully maintained and move-in ready, this home combines timeless architectural character with smart updates and practical spaces designed for today’s lifestyle.

23 Stone Ave., Winchester

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
79 Grove St, Winchester
$1,820,000
5 Beds ⋅ 4 Baths ⋅ 73545952 MLS
Space where you need it, flexibility where you want it. This extensively renovated 5-bedroom Colonial offers a rare combination of a first-floor bedroom, two upstairs suites, finished lower level, attached 2-car garage, and nearly 1/3 acre, all just minutes from Winchester Center. Sophisticated and comfortable, the home features beautifully scaled living spaces and a versatile floor plan designed for everyday living and entertaining alike. The sun-filled main level offers hardwood floors and thoughtful architectural details, with a spacious eat-in kitchen featuring an island, abundant prep space, and seamless access to the patio and private backyard. A formal dining room, oversized fireplaced living room, mudroom, half bath, and first-floor bedroom provide exceptional flexibility. Upstairs are two impressive suites with cathedral ceilings, walk-in closets, and private baths, along with two additional bedrooms, a full bath, and laundry. The finished lower level offers a spacious family room with fireplace and ample storage. An attached 2-car garage completes this exceptional home, conveniently located near Winchester Center’s shops, restaurants, commuter rail, and major routes.

79 Grove St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
666 Main Street Unit 207, Winchester
$829,000
2 Beds ⋅ 2 Baths ⋅ 73559598 MLS
Sunlit, pristine and perfectly located in the center of town ! This second floor unit features a fully renovated white kitchen (2019) with new appliances, seamlessly flowing into an open, inviting living space. Step directly out onto your private roof deck overlooking tranquil views of Wedge Pond...the ultimate spot for morning coffee or evening relaxing. The two bedroom, two bath unit also offers your own washer dryer for your convenience. Enjoy this turn-key convenience with a covered deeded parking space, an additional storage unit, and access to a beautiful in-ground pool. Close to shopping, local dining, schools, commuter rail and highways. Move in living doesn't get better than this. Schedule a showing now and don't miss out.Complete with Anderson windows and doors, mirrored dining room wall which reflects the view of the deck, custom molding and fireplaced living room.

666 Main Street Unit 207, Winchester

Listing courtesy of Listing Agent: Carolyn Vernaglia from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
42 Everett Ave, Winchester
$1,950,000
6 Beds ⋅ 5 Baths ⋅ 73588192 MLS
This distinguished residence on one of Winchester's most notable streets is a celebration of grand proportions, exquisite period craftsmanship, and timeless architectural beauty. High ceilings, four fireplaces, original hardwood floors, and beautifully scaled rooms create a sense of elegance that is increasingly difficult to find. The grand dining room is full of original details, anchored by a large fireplace and a big picture window that fills the room with natural light. A gracious living room offers another fireplace, beautiful hardwood floors, and impressive ceiling height, providing an elegant setting equally suited to intimate evenings and large-scale entertaining. A handsome first-floor study and south-facing sunroom offer quieter retreats, while the original butler’s pantry, complete with its own marble sink and original cabinets, speaks to the home’s history and the gracious way in which it was designed to be lived in. Six bedrooms + three full baths provide exceptional flexibility across the upper levels, with generous proportions and architectural details continuing throughout the home. Bonus space on the top floor and in the partially-finished basement provides room for a second home office, media room, gym or in-law space. The large patio offers privacy and entertaining space, while the grassy backyard has ample room to play. A rare three-story garage, originally designed with both chauffeur's quarters and a greenhouse, presents intriguing possibilities for the next owner. Set along prestigious Everett Avenue, in the Ambrose School District, it's a quick stroll to the town center, bus to Alewife, or Wedgemere Train Station. This residence offers an opportunity to become the next steward of a home whose craftsmanship, scale, and character simply cannot be replicated today.

42 Everett Ave, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
17 Trinity Road, Winchester
$8,000
4 Beds ⋅ 3 Baths ⋅ 73586862 MLS
**Furnished or Unfurnished** Flexible lease terms~ Fantastic opportunity to lease a spacious custom designed home on Winchester’s highly desirable West Side! Set at the end of a cul de sac on a large level fenced lot, this beautifully maintained home offers stunning space and a flexible floor plan ideal for everyday living and entertaining. The main level features a spacious living room, formal dining room, kitchen with adjoining breakfast area, plus a first-floor bedroom ideal for guests or a home office. Upstairs you’ll find a generous primary suite with walk-in closet and private bath, plus 2 additional bedrooms and a family room offering even more flexible living space. The finished lower level features a large recreation room, perfect for a playroom, gym or media space. walk out to the beautiful fenced yard; Ideally located in a wonderful neighborhood close to Winchester Center, schools, commuter rail, conservation trails, shops, restaurants and everything Winchester has to offer. A rare opportunity to enjoy space, comfort and an exceptional location in one of Winchester’s most sought-after neighborhoods!

17 Trinity Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
30 Allen Road, Winchester
$1,800,000
4 Beds ⋅ 3 Baths ⋅ 73577229 MLS
Welcome to 30 Allen Road, a beautifully situated Colonial in one of Winchester’s most desirable and walkable neighborhoods. Ideally located within easy reach of top-rated schools, shops, restaurants, and the commuter rail, this inviting home offers the space, character, and flexibility today’s buyers are looking for. The first floor features a spacious kitchen equipped with a Sub-Zero refrigerator and GE Monogram range top, opening directly to a wonderful family room with vaulted ceilings, skylights, and a gas fireplace. A bright sunroom with radiant heat provides an inviting space for year-round enjoyment, while the elegant living room offers a classic wood-burning fireplace. A formal dining room and convenient half bath complete the main level. Upstairs, the second floor offers three bedrooms, including a private primary suite, along with one additional full bath. The top floor provides two additional rooms, including a fourth bedroom and a versatile bonus space ideal for a recreation room, home office, guest space, or playroom. Outside, the property enjoys a peaceful, wooded setting with a fenced yard offering privacy and plenty of room for outdoor enjoyment. A single-car garage adds convenience and valuable storage. With its exceptional location, generous bedroom count, flexible living spaces, and charming combination of classic and modern amenities, 30 Allen Road offers a wonderful opportunity to enjoy all that Winchester has to offer.

30 Allen Road, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
7 Wainwright Rd. Unit #47, Winchester
$1,287,000
3 Beds ⋅ 3 Baths ⋅ 73580454 MLS ⋅ ['The Ledges'] BLDG.
This Ledges "A" Style townhouse condo offers extensive single floor living with a spacious first floor primary suite as well as a separate second floor suite and loft area. The main bedroom is truly vast. The first floor den can be used as a third bedroom. The home is move-in ready with all new oak hardwood floors throughout the finished areas! Entirely freshly painted in Moore's attractive Simply White. With cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, den/3rd bedroom, and kitchen with breakfast area, the home offers a lovely balance of airy open living and generous private spaces. Only bathrooms and kitchen are tiled. The home is located on a private cul-de-sac, with attached two-car garage offering convenient safety in snowy and icy weather! Enormous walk-out basement with high ceilings should you wish to expand your domain! Except for the front garden, all landscaping, exterior maintenance, snow removal done for you while you enjoy the association clubhouse, outdoor pool, tennis court and walking trails in the adjacent Sucker Brook Conservation area. Just minutes from Boston via car or train from charming Winchester Center with its coffee shops, restaurants and outdoor summer dining, pharmacies, and Whole Foods Market all near.

7 Wainwright Rd. Unit #47, Winchester

Listing courtesy of Listing Agent: Felicity F. Tuttle from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
253 Pond St, Winchester
$1,375,000
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

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
30 Farrow St, Winchester
$1,750,000
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

Listing courtesy of Listing Agent: Carlisle Group from Listing Office: Compass.
199 Washington Street Unit 199, Winchester
$948,000
4 Beds ⋅ 3 Baths ⋅ 73573734 MLS
Enjoy being just a few blocks from Winchester Center in this spacious condo with unique separate guest suite or home office. This single family alternative features 3 bedrooms on the main level and a fourth tucked away in the back of the second floor along with a 3rd bath and kitchenette. Come in the back door from the 1-car garage, or 3 parkings spaces in the driveway, straight into the large, remodeled kitchen with dining area. Appreciate the large windows in the living room. Charming details complement modern improvements. The primary suite is large enough to have an office setup within the space. Primary and hall bath have been updated. Looking for outdoor space? Whether you love the Middlesex Fells, want to have friends over for al fresco dining or do a little gardening, this is the home for you. Condo expenses are split between the 2 units. Town Center, schools, commuter rail, restaurants, shopping and the farmers market are all just a few blocks away. Boston and Cambridge are less than 9 miles away from this spot conveniently located to 93 and 95.

199 Washington Street Unit 199, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
488 Washington Street, Winchester
$4,250
4 Beds ⋅ 2 Baths ⋅ 73582959 MLS
Charming, updated Colonial filled with character. This beautiful home features an updated kitchen that is bright and open and offers granite counter tops, stainless steel appliances, frameless maple cabinets & recessed lights. Updated bathrooms. Hardwood floors throughout the 1st & 2nd floors. Access the stone and granite patio through French doors in the dining room. The patio is fenced in and there is professionally landscaped yard with stone walls. The sunny 3rd floor features skylights. Off street parking for 3-4 cars. Added bonus is a garage office space - which is a remote workers dream, with heat/ac...and already set up for remote working! Located a 2-4 minute walk from the much sought after Muraco Elementary school. Directly adjacent to the Leonard Field which offers a playground, tennis & basketball courts and soccer field. Enjoy easy access to Rte 93 & 95, commuter rail, Winchester Center, Middlesex Fells Reservation, High school & Middle school and shopping

488 Washington Street, Winchester

Listing courtesy of Listing Agent: Matthew Pierce from Listing Office: True North Realty.
10 Dartmouth Street, Winchester
$2,500,000
5 Beds ⋅ 4 Baths ⋅ 73548103 MLS
Capture the seasons from the stunning rear porch! Must see this 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

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
11 Bonad Road, Winchester
$2,000,000
4 Beds ⋅ 4 Baths ⋅ 73577339 MLS
STUNNING newer construction 4 BR, 3.5 BA home offering a wonderful blend of luxury, style & functionality in a sought-after Muraco School neighborhood near the Fells! The heart of the home is the gorgeous oversized sun-filled kitchen featuring an impressive 10' island, quartz countertops, state-of-the-art appliances & spacious dining area overlooking the gorgeous private patio filled with lush gardens & a beautifully landscaped fenced yard. An inviting living room w/gas fireplace, elegant dining room w/adjacent dry bar & custom cabinetry, and sliders to the patio create a seamless flow for everyday living & entertaining. Private 1st floor office w/french doors provides the perfect work-from-home space. Upstairs, the breathtaking primary suite boasts soaring 10'+ ceilings, dramatic double-stacked windows, walk-in closet & spa-like tiled bath w/oversized dream shower. Three additional generous bedrooms, including an en-suite, additional full bath & convenient 2nd floor laundry complete this level. The finished lower level offers a spacious family room, mudroom, ample storage & direct access to the 2-car attached garage; majority of home wired for ethernet, wifi light switches. A truly special home combining beautiful finishes, a fabulous layout & an ideal location close to schools, Winchester Center, commuter routes & the Fells!

11 Bonad Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
7 Viking Rd, Winchester
$3,000,000
5 Beds ⋅ 5 Baths ⋅ 73569252 MLS
Tucked on a quiet cul-de-sac in the sought-after Vinson Owen school district, this completely renovated 5-bedroom, 4.5-bath Colonial offers an exceptional blend of comfort and elevated design. Massive columns in classic revival style create stunning curb appeal, offering a striking introduction to the transformation inside. A spectacular chef's kitchen anchors the main level, featuring an oversized island finished in quartzite, custom cabinetry, and a full suite of professional-grade appliances —ideal for entertaining. First floor also offers a formal dining room, office, living room anchored by a fireplace as well as a private bedroom with an en suite bath. 4 generous upstairs bedrooms include a primary suite with a walk-in closet and a separate bath. Outside, the fully updated pool area creates a private resort-like setting, complemented by a professionally landscaped, fenced backyard with a generous patio for effortless summer gatherings.The fully renovated lower level extends the home's living space with an oversized media room, exercise room, additional bonus space, and another full bath—offering exceptional flexibility. Every major system has been addressed, including a new roof, heating system and central air, making this home truly move-in ready. Within walking distance of Wright-Locke Farm, Mullen Field, and the Whipple Hill hiking trails, A commuter's delight with easy access to Route 2, I-95 north and south, and Route 93. Note:Previous Assessment does not reflect the current renovated property value.

7 Viking Rd, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
7 Park Ave Unit 7, Winchester
$4,000
4 Beds ⋅ 2 Baths ⋅ 73563763 MLS
Best Deal in Town! This luxurious townhome is now available for immediate occupancy. Spanning two floors, it boasts an exceptional layout. The main floor is particularly impressive, featuring a primary bedroom, an additional bedroom, Open Concept living room and dining area, and a bright, inviting eat-in kitchen. The kitchen is equipped with ample cabinets, counter space, and stainless steel appliances. Natural light floods the home, highlighting the beautiful hardwood floors throughout. The property also includes two full bathrooms, unique spots for multiple work stations or an office, and much more. The Town of Winchester is a commuters dream with easy access to downtown Boston. Either drive or take the MBTA Bus of Commuter Rail Train. Additional amenities include two driveway parking spots, common use of the backyard plus limited basement storage. All applicants must be 18 years of age or older and complete a Rental Application. EXCELLENT credit, income, and references are required. The lease signing requires First month's rent $4,000 and a Security deposit of $4,000.

7 Park Ave Unit 7, Winchester

Listing courtesy of Listing Agent: Christopher L. Barnard from Listing Office: Barnard Real Estate Advisors, LLC.
241 Ridge St, Winchester
$1,480,000
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

Listing courtesy of Listing Agent: Team Lillian Montalto from Listing Office: Lillian Montalto Signature Properties.
200 Swanton St Unit 705, Winchester
$2,800
2 Beds ⋅ 1 Baths ⋅ 73557966 MLS
All utilities included (heat, hot water, and electricity) in this top-floor 2-bedroom, 1-bath condo with stunning views over the treetops and duck pond. Its 7th-floor perch offers exceptional privacy, quiet, and floor-to-ceiling, south-facing windows that fill the home with natural light. One cat allowed. The kitchen and bath were fully renovated several years ago, and the entire unit has been freshly painted. This elevator building features a swimming pool, newly renovated laundry rooms with convenient app-operated machines, and one parking space (additional parking available for a fee). Less than a mile to Winchester Center's cafés, restaurants, shops, and the MBTA commuter rail into Boston. The newly built Lynch Elementary School and grocery store are both approximately ½ mile away. Enjoy quick access to I-93, as well as the scenic trails and natural beauty of Middlesex Fells Reservation and Horn Pond. Available for immediate occupancy. No dogs permitted.

200 Swanton St Unit 705, Winchester

Listing courtesy of Listing Agent: Noha Soliman from Listing Office: Leading Edge Real Estate.
5 Willowdale Rd, Winchester
$1,649,900
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

Listing courtesy of Listing Agent: Erica Carson from Listing Office: Coldwell Banker Realty - Lexington.
115 Washington Unit 1B, Winchester
$2,700
1 Beds ⋅ 1 Baths ⋅ 73562666 MLS
Best rental on the market in Winchester! This Beautifully updated one bedroom and one bathroom condo is avaiable for rent. The enter island kitchen opens up to a bright living and dining room area. This home boasts of all new kitchen appliances, heat pump (heat and AC), efinished hardwood floors, & recessed dimmable lighting. California closets in both closets in the bedroom, laundry room with washer dryer in unit and entryway to provide ample storage. Walk in laundry room with extra storage is a bonus! Enjoy the convenient location to the commuter rail, library, town restaurants, & shops.

115 Washington Unit 1B, Winchester

Listing courtesy of Listing Agent: Leah Polacke from Listing Office: Gamut Group LLC.
60 Graystone Unit 60, Winchester
$6,500
3 Beds ⋅ 3 Baths ⋅ 73558912 MLS
Meticulously maintained, 2/3-bedroom, 2.5-bath townhome with 2 car garage. The kitchen features custom cabinets, granite countertops, high-end stainless steel appliances and gleaming hardwood floors. The living/dining room combo features hardwood floors, gas fireplace, cathedral ceilings along with french doors that open to a private patio with gas grill. Spacious first floor primary suite boasts a full bath with a walk-in custom shower and large walk-in closet and first floor laundry area, just outside the kitchen. Second floor offers a spacious loft family room, perfect for office or sitting area and a large second bedroom with full bath and walk-in closet. Large unfinished basement with high ceilings excellent space for storage or home gym.

60 Graystone Unit 60, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
150 Cambridge Street, Winchester
$990,000
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

150 Cambridge Street, Winchester

Listing courtesy of Listing Agent: Diane Plunkett from Listing Office: Plunkett Properties.
52 North Border Rd., Winchester
$13,000
6 Beds ⋅ 6 Baths ⋅ 73473111 MLS
Grand and masterfully crafted, this exceptional residence sits on a private road abutting the Fells conservation land, offering rare privacy and natural surroundings. The spacious home features 6 bedrooms and 6 bathrooms, beginning with a stunning foyer that opens to a sprawling first floor. Sun-filled rooms showcase exquisite custom craftsmanship throughout. The gourmet kitchen is equipped with top-of-the-line appliances and flows seamlessly into generously sized living and entertaining spaces. A private home office with custom built-ins provides the ideal work-from-home setting. Five bedrooms and a convenient laundry room are located on the second floor. The third floor offers a perfect in-law or au pair suite with generous living space, a large bedroom, and a private full bath. The recently finished basement adds approximately 1,400 square feet, including open recreation space, a full bath, and an exercise room.

52 North Border Rd., Winchester

Listing courtesy of Listing Agent: Dylan Archambault from Listing Office: The Archambault Group.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

How much is your home worth?

Get instant property value now!