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$3,299,000
7 Beds ⋅ 8 Baths ⋅ 73498293 MLS
Ideally situated in one of Winchester's most desirable neighborhoods, 1 Plymouth offers the rare combination of exceptional living space and unmatched convenience just minutes to Winchester Center, top-rated schools, commuter rail access, country clubs, and local amenities.Thoughtfully expanded and rebuilt, this impressive residence features 7 bedrooms, 7 full baths, and 1 half bath, designed to accommodate today's evolving lifestyle. At the heart of the home is a stunning chef's kitchen that flows seamlessly into a fireplaced family room with soaring cathedral ceilings, creating an inviting space for both everyday living and entertaining.What truly sets this property apart is its versatility. A private two-bedroom au pair offers its own living area, office, wet bar, and full bath ideal for extended family, guests, or live-in support. A finished lower level provides valuable additional living and recreation space.Just moments from Mullen Field, and everything Winchester has to offer

1 Plymouth Rd, Winchester

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.
$3,200,000
6 Beds ⋅ 6 Baths ⋅ 73482275 MLS
Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer kitchen w/vaulted ceilings, skylights, oversized island, sliders to large deck & a fire-placed family room, along with formal living and dining rooms & a FIRST FLOOR bedroom suite! The 2nd floor offers 4 generous BR's including a luxurious primary suite, 2 additional full baths & convenient second floor laundry. The above grade/ walk-out lower level adds exceptional flexibility w/ *Au- pair or In-law suite* media room, home office, exercise room, bedroom & full bath Enjoy all the area has to offer including restaurants, shops, schools, train to Boston, Bike-paths & more! 7 miles from Boston

9 Albamont Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$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

Listing courtesy of Listing Agent: Karima Alami from Listing Office: Compass.
$3,179,000
7 Beds ⋅ 8 Baths ⋅ 73502853 MLS
Magnificent newer sun filled colonial w/oversized rooms offering over 8,000 sq ft of beautifully finished living space featuring 7 grand BR's, 7.5 BA across 4 levels w/a 3-car direct entry garage. This expansive home showcases exceptional craftsmanship including custom built-ins, fine cabinetry, decorative moldings, 4 fplc & a great layout. The newly renovated kitchen features sleek quartz countertops, oversized island, 2 dishwashers & butler’s pantry w/ice maker & wine fridge flowing into formal DR & LR plus a fireplaced FMRM overlooking a meticulously maintained yard. Each oversized bedroom offers an en-suite bath, sitting area & walk-in closet, providing comfort & privacy throughout. The 1st flr includes a private office w/wet bar plus a lavish bedroom wing ideal for guests or multi-generational living. The 3rd floor suite features a full BA & 2 closets, while the finished lower level adds media/game/gym areas w/access to stunning heated pool, complimented by lush outdoor landscape

37 Mayflower Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,149,000
5 Beds ⋅ 6 Baths ⋅ 73513501 MLS
Truly one of a kind new construction blending timeless design with modern luxury, 8 Priscilla Ln offers 6,500± sq ft of thoughtfully designed living space. Elegant archways and a dramatic two-story living room create an immediate sense of scale and character. The chef's kitchen features custom cabinetry, Thermador appliances, and an oversized island, flowing seamlessly into the main living and dining areas, while the oversized pantry completes the space. Three bedrooms including the primary suite feature en suite baths, with two offering spacious walk-in closets. The primary suite provides a spa-inspired bath and a generous walk-in closet. The expansive lower level, with ceiling heights over 10 ft, offers flexible space for an au pair, media room, gym, or additional living area. Designed by Salt and Stone Co., with a two-car garage. Seller is offering a backyard improvement credit at closing toward landscaping, hardscape, or outdoor living features of the buyer's choice. Prime location

8 Priscilla Ln, Winchester

Listing courtesy of Listing Agent: The Pezzano Group from Listing Office: Rise Signature Homes.
$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

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,799,000
6 Beds ⋅ 7 Baths ⋅ 73500890 MLS
Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England Colonial style. Curved front stair case add one more layer of beauty. Second floor and third floor offer total 6 bedrooms, suites and walk-in closets. Master bedroom is with cathedral ceilings, a sprawling master closet and an office/sitting area. Smooth flow of the spacious and walk out lower level enables rich life style with billiard room, media room, art room and exercise room -- all designed for a modern lifestyle, with an open layout that is perfect for entertaining. State of the art systems with total 6 heating and cooling zones and central vacuum system.

14 Nassau Drive, Winchester

Listing courtesy of Listing Agent: Weidong Li from Listing Office: WINN Real Estate & Consulting.
$2,795,000
4 Beds ⋅ 5 Baths ⋅ 73518621 MLS
This European-inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the home is a designer chef’s kitchen w/ bespoke cabinetry, lux appliances, and an adjoining mudroom. Outside, the property transforms into a private resort-like retreat with granite-columned loggia, heated saltwater pool, landscaped grounds w/ irrigation, and multiple entertaining areas. The spa-like primary suite, ensuite guest bedrooms, finished lower level with flexible bonus spaces, and heated driveway/walkways complete this estate. A lifestyle of luxury/convenience steps away from town, commuter rail, school and walking trails.

18 Middlesex St, Winchester

Listing courtesy of Listing Agent: Tina Natale from Listing Office: Luxury Living Real Estate.
$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

Listing courtesy of Listing Agent: Steph Crawford Group from Listing Office: Real Broker MA, LLC.
$2,499,000
5 Beds ⋅ 4 Baths ⋅ 73526460 MLS
Must see this completely renovated & expanded stately brick home located just outside the town center offering the perfect blend of timeless charm & modern living. Thoughtfully re-designed with an open concept layout, the home features a custom high end kitchen that flows into a gorgeous oversized family room addition* w/ walls of windows overlooking a stunning private backyard. Formal LR and DR, mudroom, stylish 1/2 bath & home office/sunroom complete this floor. Upstairs you'll find five spacious bedrooms and two full baths including the most perfect primary suite w/gorgeous bath plus a sitting room. Many updates include new hardwood floors, new high end Pella windows, updated electrical, heating and cooling systems finished lower level offers excellent recreation Enjoy the great landscaped yard with patio, lawn and sports court! For sure a favorite gathering spot for family and friends.

78 Bacon Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,399,000
5 Beds ⋅ 4 Baths ⋅ 73525195 MLS
Stunning new construction in highly sought-after Winchester! This thoughtfully designed home blends modern style with everyday functionality. The first floor features an open-concept kitchen, dining area, and sun-filled living and family rooms with soaring ceilings open to the second floor and a cozy fireplace, perfect for entertaining or relaxing. A first-floor bedroom, full bath, and convenient laundry add flexibility for guests or multigenerational living. Upstairs, the luxurious master retreat boasts a cozy gas fireplace, expansive walk-in closet, and spa-like bath, followed by another bedroom with an ensuite bath, and two additional bedrooms sharing a Jack and Jill bath. A finished basement provides versatile space for a gym, media room, or playroom. Enjoy a charming front porch, private back deck, durable Hardy Plank exterior, and attached two-car garage. Exceptional craftsmanship and timeless curb appeal make this a must-see home! Located within the Winchester School District

53 Winford Way, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$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

Listing courtesy of Listing Agent: Rebecca Huang from Listing Office: William Raveis R.E. & Home Services.
$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

Listing courtesy of Listing Agent: Gretchen Papineau from Listing Office: Coldwell Banker Realty - Andovers/Readings Regional.
$2,195,000
5 Beds ⋅ 4 Baths ⋅ 73496396 MLS
Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!

276 High Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$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

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
$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

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$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

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
$1,899,000
6 Beds ⋅ 5 Baths ⋅ 73507137 MLS
Must see! sprawling 2-3 family beautifully renovated & expanded home offering flexibility for multigenerational living, complete w/ a legal unit over the garage ideal for in-laws, nanny, guests, or rental income. Thoughtfully designed w/ a seamless blend of private & communal spaces, the main home features an updated kitchen w/ mudroom, laundry & pantry, a spacious living room w/ gas fireplace, dining room, 1st flr bedrm & full bath, plus a flexible suite w/ kitchenette, sitting room & full bath. Upstairs offers 3 add' bedrooms & a full bath. The finished lower level includes a family room, office, exercise space, bonus room w/ walkout, workshop, storage & cedar closet. Additional highlights include an oversized 2-car garage with EV charger, elevator lift, solar array, & direct access to the apartment featuring vaulted ceilings, gas fireplace, full kitchen, laundry & private deck. Set on an oversized level lot with mature landscaping, deck, patio & gazebo on a quiet cul-de-sac!

16 & 16A Glenwood Ave, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,825,000
5 Beds ⋅ 4 Baths ⋅ 73522773 MLS
Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees. The open-concept living and dining area provides a seamless flow, ideal for hosting gatherings or simply relaxing with guests. Family room w/window seat and built-ins, leads to a sunny deck. Next level, you enter an en-suite bedroom and two large additional Bdrms with an updated bath. Two more Bdrms on the upper level can be utilized for a guest or family member w/ultimate flexibility. Lower level, there are Power Rm, Laundry Rm, Dog Spa & Study. This residence provides the ideal blend of functionality and style. Close to Vinson Owen School. This dream home provides easy access to everything!

8 Hawthorne Road, Winchester

Listing courtesy of Listing Agent: H. Elaine Song from Listing Office: Coldwell Banker Realty - Lexington.
$1,750,000
3 Beds ⋅ 3 Baths ⋅ 73551306 MLS ⋅ ['Graystone At Winchester'] BLDG.
OFFER ACCEPTED-OH CANCELLED!Discover luxury & convenience in this impeccably maintained 2-3 bed, 2.5-baths unit in desirable Graystone!! A high end townhome community located just outside Winchester center offering a 1st floor primary suite! The gourmet kitchen showcases custom cabinetry, granite countertops, top-of-the-line stainless appliances w/new gas stove. The open-concept living & dining area w/ a gas fireplace, gleaming hardwood floors & soaring cathedral ceilings w/ skylights, leading to a private, deck & yard—perfect for outdoor relaxation. The spacious first-floor primary suite offers a marble bathroom w/ a custom walk-in shower & generous closet space. Upstairs, the spacious second bedroom, full bath plus an oversized loft family room area w/ potential to wall off a portion for 3rd bedroom, & a cozy a den/ office The walkout LL has high ceilings & offers opportunity to finish 1440SF for gym/rec room, media room, storage or anything you desire!

18 Graystone Circle Unit 18, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$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

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$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

Listing courtesy of Listing Agent: Dara Singleton from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$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

Listing courtesy of Listing Agent: Team Lillian Montalto from Listing Office: Lillian Montalto Signature Properties.
$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

Listing courtesy of Listing Agent: Danielle Fleming from Listing Office: MA Properties.
$1,299,000
3 Beds ⋅ 3 Baths ⋅ 73534894 MLS ⋅ ['The Ledges'] BLDG.
Waiting for you to enjoy: your carefree home with cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, adjacent den/3rd bedroom, and kitchen with breakfast area! This "A" style Ledges condominium on a private cul-de-sac includes a FIRST FLOOR PRIMARY SUITE with generous bedroom, large closets and primary bath with double sinks, shower and tub. Spacious single floor living! Plus an upper floor with a loft office space overlooking the living room, and an attractive 2d bedroom suite. The unfinished walk-out basement offers significant room to expand. Landscaping, exterior maintenance, snow removal all 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 Road Unit 47, Winchester

Listing courtesy of Listing Agent: Felicity F. Tuttle from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,199,000
3 Beds ⋅ 3 Baths ⋅ 73519082 MLS
Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

53 Lake Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,195,000
4 Beds ⋅ 3 Baths ⋅ 73546076 MLS ⋅ ['50-52 Middlesex St Townhomes'] BLDG.
Newly renovated 4-bedroom, 3-bath townhome offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy new white oak hardwood floors, a stunning chef's kitchen with quartz countertops and full-height quartz backsplash, Bosch stainless steel appliances, and beautifully designed bathrooms with custom tile and premium Kohler fixtures. Additional upgrades include a new roof, new central A/C and heat, recessed lighting, and all-new systems throughout. Winchester is renowned for its award-winning schools, charming New England downtown filled with shops, restaurants, and cafés, easy commuter rail access to Boston, and convenient proximity to major highways—offering the perfect blend of suburban tranquility and city convenience.

52 Middlesex Street Unit 52, Winchester

Listing courtesy of Listing Agent: The North Star Group from Listing Office: Keller Williams Realty Evolution.
$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

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$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

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 73549484 MLS
Completely renovated in 2021, this stunning 3-bedroom, 2.5-bath townhouse offers the comfort and feel of a single-family home with three levels of beautifully finished living space. The open and inviting floor plan features hardwood floors throughout, modern finishes, and abundant natural light. The spacious third-floor primary suite provides a private retreat with spacious walk in closet and its own full bath. Second floor features 2 ample sized bedrooms, full bath and laundry. Step outside through the sliding glass doors to a newly installed stone patio and backyard—perfect for relaxing, entertaining, or outdoor dining. Additional highlights include two off-street parking spaces and thoughtful updates throughout. Ideally located just moments from the Winchester Center commuter rail station, vibrant downtown shops and restaurants, Winchester High School, and the brand-new Lynch Elementary School, this move-in ready home offers the perfect combination of style, space, and convenience.

52 Salem Street Unit 52, Winchester

Listing courtesy of Listing Agent: Michael Rauseo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

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