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20 Foxcroft Road, Winchester
$4,450,000
5 Beds ⋅ 7 Baths ⋅ 73431361 MLS
A rare opportunity to own one of The Flats’ most celebrated homes! This 1930s Colonial Revival w/ classic curb appeal & elegant proportions sits on over ½ acre of estate-like grounds featuring heated pool, patios, pergola & multiple areas for effortless entertaining. Inside, a grand foyer & sweeping staircase introduce gracious rooms w/ exquisite millwork & superb flow, equally suited for relaxed family living or refined gatherings. Highlights include eat-in chef’s kitchen w/ island & timeless finishes, butler’s pantry, stately dining rm, large living & family rms & private study. Upstairs offers a luxurious primary suite w/ marble bath & dressing rm, plus 4 add’l BRs, 3 en suite. Lower level features versatile family/game rms & wine cellar. Carriage house (2007) w/ 4 garage bays, cabana bath & studio/gym offers endless possibilities & ADU potential. Moments to town center, top rated schools & train, this iconic home is where elegance & livability come together in perfect balance.

20 Foxcroft Road, Winchester

Listing courtesy of Listing Agent: Carolyn Walsh from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
12 Ledgewood Road, Winchester
$3,900,000
5 Beds ⋅ 5 Baths ⋅ 73439119 MLS
A rare Winchester offering set on an acre in a wooded enclave of luxury homes near town center. Custom-built, this 5-bedroom, 4.5-bath residence combines timeless design with balanced proportions across four levels. The primary suite includes a private deck, spa-like bath with soaking tub, and gas fireplace. The chef’s kitchen features quarter-sawn oak cabinetry, high-end appliances, large island, pantry, and wet bar, opening to casual and formal spaces. A four-season sunroom leads to an outdoor oasis with extensive landscaping, stonework, patio, outdoor kitchen, built-in fireplace, and private tennis court. High ceilings, crown molding, custom quarter-sawn oak built-ins, and classic finishes are found throughout, thoughtful choices using healthy home materials. Additional highlights include a large mudroom, laundry room, and a finished lower level with family room, bath, exercise area, and ample storage. Truly unique close to town center, top-ranked schools, and easy access to Boston.

12 Ledgewood Road, Winchester

Listing courtesy of Listing Agent: Leigh Ventura from Listing Office: Compass.
29 Ginn Rd, Winchester
$3,799,000
6 Beds ⋅ 8 Baths ⋅ 73534577 MLS
Exceptional new construction offering approximately 6,000 sq ft of thoughtfully designed living space with 6 bedrooms, 7.5 baths, and a 3-car garage. A striking exterior showcases natural stonework, copper roof accents, copper gutters, and a welcoming covered porch. Inside, custom millwork, wide-plank hardwood floors, soaring ceilings, a floating staircase, and designer finishes create a timeless yet modern aesthetic. The chef's kitchen features Wolf & Sub-Zero appliances, custom cabinetry, and an oversized island, flowing seamlessly into the main living spaces. Expansive glass doors open to a covered outdoor patio area with a stunning stone fireplace. The luxurious primary suite offers a spa-inspired marble bath and oversized custom walk-in closet. The finished lower level includes a recreation room, wet bar, media space, home gym, and additional entertaining areas. Just moments away from Winchester's vibrant downtown center and the commuter rail, this home is a must see!

29 Ginn Rd, Winchester

Listing courtesy of Listing Agent: Peter Kasseris from Listing Office: Serhant.
5 Stratford Road, Winchester
$3,599,000
6 Beds ⋅ 5 Baths ⋅ 73420138 MLS
This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf range, paneled appliances, & wine bar. The first floor features generously sized rooms that flow beautifully, offering grand entertaining spaces, 4 fireplaces, & a statement staircase. Upstairs offers 4 bedrooms & 3 updated baths, including a serene primary suite w/ fireplace, marble bath & double closets. The third floor includes 2 add'l. beds, full bath, & room for expansion. Enjoy a private fenced yard w/ lush gardens, patio, & a 2+ car garage. With timeless character and thoughtful updates throughout, this is a rare opportunity just moments from town, train, and top schools!

5 Stratford Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
50 Oxford Street, Winchester
$3,500,000
5 Beds ⋅ 4 Baths ⋅ 73515077 MLS
**OFFER ACCEPTED OPEN HOUSE CANCELED** Set on an oversized lot w/ a stunning in-ground pool, jacuzzi, pool house & expansive level lawn, this exceptional home blends luxury, privacy, & modern living. Expanded & extensively renovated top-to-bottom, the home features an open layout w/ designer kitchen, spacious family room & oversized attached 2-car garage. Walls of windows & French doors overlook the spectacular private yard, creating seamless indoor-outdoor living. The chef’s kitchen offers double islands, custom cabinetry, & high-end Wolfe & Sub-Zero appliances. Flexible 1st flr w/ potential bedrm & adjacent full bath, oversized dining rm, & high ceilings throughout. The beautiful primary suite features vaulted ceilings & full bath. Generously sized secondary bedrooms & large hall bath w/ soaking tub & separate shower complete the second floor. Finished LL w/ gym/media rm, abundant storage & new systems including electrical, plumbing & windows complete this rare Flats offering!

50 Oxford Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
10 Sheffield West, Winchester
$3,470,000
5 Beds ⋅ 6 Baths ⋅ 73472359 MLS
Exceptional Colonial Revival in one of Winchester’s most sought-after Sheffield neighborhoods, known for its tree-lined streets and a shared community green. Timeless architecture meets modern livability across four finished levels. The chef’s kitchen features a large island, walk-in pantry, wet bar, and custom cabinetry, opening to a spacious family room with gas fireplace. Formal living and dining rooms offer hardwood floors, crown molding, and abundant natural light. The primary suite includes walk-in closets and a spa-like bath, with additional generously sized bedrooms and baths. The 3rd floor provides flexible living with bedroom, study, bonus room, and full bath, while the finished lower level adds recreation space. Recent improvements include exterior paint (2024), perimeter fencing with gated driveway, ornamental landscaping, enclosed mudroom storage, and a custom Dutch door. Detached 2-car garage and private yard. Close proximity to Winchester Center and Wedgemere Stations.

10 Sheffield West, Winchester

Listing courtesy of Listing Agent: Jay Noble from Listing Office: Lamacchia Realty, Inc..
40 Foxcroft Rd, Winchester
$3,450,000
6 Beds ⋅ 5 Baths ⋅ 73485774 MLS
40 Foxcroft Road presents exceptional new construction in the highly desirable Flats of Winchester. This 6BR, 4.5BA residence spans 6,460 sqft and showcases thoughtfully curated design with an open concept floor plan ideal for modern living and entertaining. The sun-filled living room features soaring vaulted ceilings with exposed wood beams and a gas fireplace, framed by expansive Pella windows. The chef’s kitchen is appointed with a premium Thermador appliance package and an elegant dry bar with integrated lighting. Custom millwork throughout adds warmth and architectural detail. A home office is located on the main level. The luxurious primary suite offers a custom walk-in closet with built-in lighting and a spa-inspired bath with steam shower. The top level offers two additional bedrooms ideal for guests or play space. The finished lower level includes a media room and home gym. A spacious deck overlooks the backyard, creating the perfect setting for outdoor entertaining.

40 Foxcroft Rd, Winchester

Listing courtesy of Listing Agent: The Boston ONE Team from Listing Office: Serhant.
4 Norwood St, Winchester
$3,242,250
5 Beds ⋅ 5 Baths ⋅ 73397101 MLS
Welcome to 4 Norwood St, a stunning custom-built home by Mark Stephen Development. Just a short walk to Winchester town center with easy access to Boston, this home features exquisite millwork, custom built-ins, and premium finishes throughout. The main home offers 4 bedrooms, 3.5 bathrooms, a living room, dining room, sitting room, pantry, and a bar alcove, along with an expansive second-floor office/flex space. A separate but attached ADU—perfect for extended family or guests—boasts soaring 13’6” ceilings, a grand entertaining area with chandeliers, a full kitchen, and a private guest primary suite. With every imaginable bell and whistle, this home is truly one of a kind.

4 Norwood St, Winchester

Listing courtesy of Listing Agent: Mark Donnellan from Listing Office: Gibson Sotheby's International Realty.
2 Everett Ave, Winchester
$3,230,000
7 Beds ⋅ 6 Baths ⋅ 73488991 MLS
Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end eat-in kitchen with large island & granite countertops as well as a formal dining room with gas fireplace. A living room with custom built-ins & window seat, a family room overlooking the yard, and a bar complete this level. This distinguished residence offers 7 bedrooms and 6 bathrooms, blending timeless architectural details with luxurious modern amenities. Additional highlights include a primary suite with walk-in closet and sitting room, large entertainment room, 3 car garage, and close proximity to downtown and commuter rail. Don’t miss this rare opportunity to own a truly remarkable estate.

2 Everett Ave, Winchester

Listing courtesy of Listing Agent: Joan Francis Sullivan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
39 Town Way, Winchester
$3,200,000
6 Beds ⋅ 7 Baths ⋅ 73442521 MLS
Discover all this gorgeous new construction home in top East Side location will offer! Designed with today’s lifestyle in mind, this home features a flexible open floor plan perfect for entertaining & everyday living / A great opportunity for you to customize the finishes & bring your vision to life! First floor offers a mudroom, half bath, office/living room, bedroom w/ full bath & a stunning high-end kitchen open to the dining room & spacious family room w/ fireplace, leading to a deck & large yard! The second floor features four generous bedrooms & three full baths, including a luxurious primary suite w/ a spa-like bath & walk-in closet, plus a convenient laundry room. The third floor includes an additional bedroom w/ rec/lounge area & oversized full bath! The walk out finished lower level provides a large recreation room, gym & full bath..perfect for family fun or entertaining. Reach out today for a site visit and a tour of this fabulous home to be completed by early spring 2026!

39 Town Way, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
257 High Street, Winchester
$3,150,000
5 Beds ⋅ 7 Baths ⋅ 73499287 MLS
OPEN HOUSE CANCELLED 4/12 **OFFER ACCEPTED** Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck, mudroom, pantry & oversized 2 car garage. The 2nd floor offers a stunning master w sitting area, marble bath & walk in closet. 3 add'l BR's, all generously sized. The expansive lower level features an inviting screened "Florida room" family space that opens to a bluestone patio with fire pit, overlooking expansive meticulously maintained lawn & an outdoor shower! Additionally in the LL, there is a movie theatre, full kitchen, gym, bedroom, game room w fplc, perfect for ADU/ extended family or everyday living & entertaining. Must see this fabulous home~

257 High Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
12 Salisbury Street, Winchester
$3,100,000
6 Beds ⋅ 5 Baths ⋅ 73496654 MLS
Welcome home to this stunning colonial on one of Winchester's most beloved streets. Featuring 6 bedrooms and 4.5 baths, this has been extensively renovated, creating space to spread out and truly live. Rich hardwood floors, 3 fireplaces, and a gracious flow make every room feel warm and inviting. The gourmet kitchen- complete with granite countertops, a large island, butlers pantry, wine chiller, double dishwashers and stainless appliances- is the heart of the home. The primary suite is a true retreat with a fireplace, walk-in closets, and spa bath with soaking tub. A sun room, custom mud room, finished basement, and 3rd-floor bedrooms offer room for everyone and everything. Outside, a bluestone patio, wood burning fireplace, covered deck, enclosed porch, professional landscaping and irrigation system create a beautiful and private setting, while a 2-car detached garage and 6-car paved driveway provide exceptional storage and parking. Surely a highlight of Winchester's spring market!

12 Salisbury Street, Winchester

Listing courtesy of Listing Agent: Karen S. Garrett from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
54 Johnson Rd, Winchester
$3,100,000
5 Beds ⋅ 8 Baths ⋅ 73474290 MLS
This STUNNING newly constructed home facing Old Village Drive redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends style w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master builders commitment to exceptional quality & craftsmanship shines through every detail. Spanning four meticulously finished levels, this home leaves nothing to be desired. Highlights include a chef's kitchen w/ dual islands, vaulted ceilings, wine fridge, coffee bar, charming breakfast nook, butler's & dry pantries, a direct entry first-floor office or in-law suite & full third floor w/ hardwood floors & bath. The expansive lower level offers a family room, movie theatre, game room, gym plus private entry separate living quarters w/full in-law/au-pair suite w/ kitchen, 2nd laundry,BR & bath

54 Johnson Rd, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
25 Myopia Road, Winchester
$3,100,000
4 Beds ⋅ 4 Baths ⋅ 73471735 MLS
A timeless home of exceptional craftsmanship on the coveted slope of Myopia Hill, offering tranquil views of lush gardens and rolling hills. Thoughtful architectural details enrich every space, while multiple patios and wrap-around porch create an effortless flow between indoor& outdoor. The gracious main level unfolds into beautifully connected living spaces, featuring an office, elegant dining room, chef’s kitchen adorned by enchanting breakfast area and an inviting living &family room anchored by a stone fireplace. The upstairs primary suite is a private retreat w/ its own balcony, dressing rooms, cedar closet & a spa-inspired bath. The private backyard—with its historic stone hunter gazebo, fire pit, mature trees and layered plantings—offers both openness and seclusion. Within close proximity to Winchester Country Club and offering a swift commute to Boston & major highways, this exceptional property delivers privacy and prestige in one of Winchester’s most desirable enclave.

25 Myopia Road, Winchester

Listing courtesy of Listing Agent: Wenjun Cao from Listing Office: Engel & Volkers Boston.
27 Everett Ave, Winchester
$3,100,000
6 Beds ⋅ 6 Baths ⋅ 73468691 MLS
This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are beautifully preserved, elevated by the warm glow of restored hardwood floors. Generous, light-filled rooms unfold with grace and scale throughout. A newly designed chef's kitchen, new baths, walk-in pantry w/laundry and a classic butler’s pantry with wine refrigerator are some of the highlights. Anchoring the home is an expansive family room, framed by floor-to-ceiling windows overlooking a park-like lawn. A rare offering where architectural pedigree, thoughtful architecture and renovation, and exceptional land converge.

27 Everett Ave, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
4 Lawrence St, Winchester
$3,070,000
6 Beds ⋅ 8 Baths ⋅ 73524328 MLS
A beautifully renovated and expanded Colonial in the Flats, blending old-world charm with modern living that suits a myriad of needs. The main home features high ceilings, restored original woodwork, and updated systems throughout. The kitchen invites the outdoors in with views of the private, tree-lined backyard with mature plantings, an expansive covered patio, and firepit for cozy evenings. The 2nd floor offers 4 beds and 3 baths, including a stunning primary suite with cathedral ceilings, marble bath, and sun deck access. A third-floor flex space adds a bar and bath. The bi-level in-law/au-pair suite is complete with full bath and kitchenette. Add a detached two-car garage with 2nd-story finished living area, bar, and full bath, and there are multiple offerings for autonomy, extended-stay guests, an au-pair, or teens seeking their own space. A rare opportunity to call this exceptional oasis home in the heart of the Flats, with Winchester Center and the commuter rail close by.

4 Lawrence St, Winchester

Listing courtesy of Listing Agent: Burbs to Boston from Listing Office: Compass.
115 Church St, Winchester
$2,975,000
7 Beds ⋅ 6 Baths ⋅ 73512327 MLS
Distinguished Colonial Revival located in the desirable “Flats" neighborhood offering 5,888 SF with 7 bedrooms and 6 baths across three finished levels. Period details include a quartered oak foyer and staircase, bay windows, pocket doors, and decorative millwork. Chef's kitchen features a Viking gas range, Thermador refrigerator, and granite countertops. Family room has a wood-burning fireplace and built-ins. Formal living and dining rooms offer generous proportions and period character. Second floor hosts a primary with en suite bath, a second en suite bedroom, and two additional bedrooms served by a hall bath. Renovated third floor features wide pine floors, a full bath, and flexible space for offices or bedrooms. Recreation room has a wet bar, half bath, and a balcony. Situated on a .41-acre corner lot that boasts a large flagstone patio, a basketball court and driveway access from Wedgemere Avenue. Minutes to Winchester Center, commuter rail, schools, and conservation trails.

115 Church St, Winchester

Listing courtesy of Listing Agent: Jennifer Ryer from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
26 Swan Road, Winchester
$2,900,000
6 Beds ⋅ 7 Baths ⋅ 73404870 MLS
*Incredible value!* Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with 2 primary & suite options! This magnificent residence boasts expansive living spaces, elevator, indoor pool & 3 car garage! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end appliances leading to adj. family room w/ fireplace. A handsome library w/ fireplace offers a warm and inviting space to relax. The highlight of this extraordinary home is the 16x32 indoor gunite pool & jacuzzi set within a breathtaking atrium room w/soaring vaulted ceilings, perfect for year round exercise and entertainment. Each of the spacious bedrooms provides a retreat-like atmosphere, complete w/ensuite baths for ultimate comfort & privacy. The home also features 4 fireplaces, 2 home offices, a newly finished basement w/ rec room, fplc, BR & full bath!

26 Swan Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
6 Abby Road, Winchester
$2,895,000
5 Beds ⋅ 5 Baths ⋅ 73424449 MLS
Here's a rare opportunity to own a spectacular new construction home by a premier local builder on a BRAND-NEW road. This property stands prominently on its lot, overlooking a lush wooded area with close proximity to “The Fells”. The first floor is designed for both entertaining and everyday living, featuring formal dining, a designer kitchen with a butler's pantry, and a fireplaced family room that exudes warmth and comfort. Each of the bedrooms are found on the second floor, including a versatile space that could seamlessly integrate into the primary. The primary bath is a sanctuary of luxury, accompanied by an opulent dressing room. The lower level offers a walk-out rec room and a dedicated home gym. The HUGE garage is perfect for car enthusiasts who might wish to install a lift, or for sports enthusiasts aiming to create an indoor basketball/golf simulator area! Seize your chance to acquire this exceptional property, where construction and finishes of such caliber are seldom found.

6 Abby Road, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
54 Wedgemere Avenue, Winchester
$2,862,500
6 Beds ⋅ 4 Baths ⋅ 73428556 MLS
Exceptional value, prime living in this stunning home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive backyard featuring gorgeous patio & maintenance free heated POOL w/ in- floor cleaning system & auto cover! Inviting covered rear porch /gazebo for outdoor living complete with movie night projector! Impressive family rm w/ views of yard, gas fireplace & built in bookshelves . Stylish formal dining rm w/ bay window & custom wainscoting, front to back LR w/ fplc; grand rooms, detailed moldings, updated baths, primary suite w/ 2 walk in closets, spa like bath w/oversized shower & soaking tub. Full 3rd floor w/ 3 Beds & full bath, new heating/ cooling, newer roof. 2 car garage w/space above & basement awaits finishing!

54 Wedgemere Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
56 Yale Street, Winchester
$2,830,000
5 Beds ⋅ 4 Baths ⋅ 73491616 MLS
Gracefully appointed in the sought after "Flats" this stunning Colonial has been superbly expanded & transformed into 4 levels of living space, offering a perfect blend of timeless details with well thought-out quality renovations. The front entry makes a striking first impression! Inside every turn is rich w/ detail- fireplace LR, elegant dining rm, crown molding, wainscoting, HW flrs & an exquisite built-in cabinet. The award-winning kitchen is nothing short of spectacular, with 2 walk-in pantries, wet bar & many outstanding features. You'll love the sunken family rm, adjoining mud rm, & bath. French doors extend the living space to a serene outer setting featuring mahogany deck & an alfresco kitchen. The luxurious primary suite is a stunner w/ spa-like marble bath, steam shower, walk-in closet & unique nursery/office. The finished lower level,2c gar, EZ access to the commuter rail & center of town complete this distinctive home. A rare offering & wonderful opportunity!

56 Yale Street, Winchester

Listing courtesy of Listing Agent: Patricia Fitzgerald from Listing Office: Brad Hutchinson Real Estate.
7 Cliff Street, Winchester
$2,800,000
6 Beds ⋅ 4 Baths ⋅ 73509698 MLS
Gracious 1890 colonial on .3 acre lot on dead end overlooking Middlesex Fells. Close to I-93, town center, train, and top Winchester schools (Lincoln Elementary). Welcoming front porch leads to a beautiful foyer. First floor features a living room with wood FP and bookshelves, and a large family room with gas FP accessing a side porch, a back deck and the kitchen. Renovated kitchen has large island, built-in desk and casual eating area. Formal dining room, half bath, mudroom, and pantry at the back staircase complete the 1st floor. Upstairs, the primary suite showcases a tub, shower, double sinks, plus walk-in closet. 3 additional bedrooms share a tiled bath. 3rd floor has another full bath, 2 more bedrooms and an office for a variety of uses. Finished basement houses a large rec room, laundry and mechanical rooms, plus generous storage. Highlights include central air, 2 car garage plus 4 driveway spaces, rear deck, side porch, beautiful landscaping and sprinkler system. Offers 5/5 4p.

7 Cliff Street, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
74 Wedgemere Avenue, Winchester
$2,793,000
5 Beds ⋅ 5 Baths ⋅ 73499151 MLS
The most idyllic setting in town! This beautifully renovated and expanded Colonial blends timeless charm with modern sophistication. Perfectly sited on an 18,000 sq ft lot abutting conservation land, it offers exceptional privacy in one of the town’s most coveted neighborhoods. This stunning home features 5+ bedrooms and 4.5 baths, with new windows, updated systems, an expanded kitchen, and beautifully appointed baths throughout. The elegant kitchen overlooks a large, level backyard with direct access to a bluestone patio—ideal for entertaining—set against acres of serene conservation. The second floor offers a gracious primary suite with bath, plus four additional bedrooms and two full baths. The finished lower level features high ceilings, a fireplace, full bath, sauna, and direct yard access.

74 Wedgemere Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
19 Town Way, Winchester
$2,750,000
5 Beds ⋅ 6 Baths ⋅ 73455886 MLS
Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive kitchen and dining area form the heart of the home—perfectly suited for lively entertaining, relaxed gatherings, and everyday living. Upstairs, the primary suite offers a luxurious retreat, while the spacious third-floor teen suite provides comfort, privacy, and versatility. The finished lower level—with its full bath—adds tremendous bonus space for play, guests, or hobbies. Blending modern craftsmanship with timeless appeal, this home delivers exceptional living just a stone’s throw from the Middlesex Fells Reservation, where nature’s beauty is right at your doorstep.

19 Town Way, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
11 Taft, Winchester
$2,750,000
5 Beds ⋅ 6 Baths ⋅ 73419844 MLS
Open house canceled! Offer accepted! Luxury, location, and lifestyle come together in this beautiful new 5-bed, 5.5-bath home in Winchester’s sought-after Westside. Just steps to Ambrose School, one block from the Alewife bus stop, a short stroll to the commuter rail, and right down the street from the Winchester Boat Club, this home offers unmatched convenience and charm. Inside, enjoy over 4,600 sq. ft. of thoughtfully designed space with white oak floors, imported tile, a chef’s kitchen with Viking appliances and custom cabinetry, and a cozy living room with a natural stone gas fireplace. Dual primary suites—on both the first and second floors—feature spa-like en-suite baths. The finished lower level includes a gym, family room, full bath, and mudroom with direct access to an oversized double-bay garage. This turnkey home is the perfect blend of elegance and everyday ease. A rare opportunity in an exceptional location!

11 Taft, Winchester

Listing courtesy of Listing Agent: Rose Hall from Listing Office: Blue Ocean Realty, LLC.
15 Yale St, Winchester
$2,700,000
7 Beds ⋅ 4 Baths ⋅ 73510619 MLS
Beautifully renovated 5 bedroom, 11 room home w 2 home offices located in the desirable FLATS area of town. An inviting front porch welcomes you into this special home showcasing the charm & character of historic Winchester, with amenities and layout desired today. Magazine worthy kitchen/dining/ family room! Open concept first floor with 3 rooms directly overlooking gorgeous and private rear yard w/ deck, patio, mature landscape and an abundance of privacy. Oversized 2 car garage is a huge bonus and rarely found in this part of town! Second floor includes 3 beds, 2 full baths & laundry room. 3rd level offers 3 sun drenched oversized Bedrooms w/ full ceiling height & full bath. Primary bedroom suite w/ spa like bath; oversized steam shower w/body sprays/bench/surround sound, radiant flooring & towel warmer plus a large newly constructed walk in coset! Close to the center & train to Boston. Ambrose School*

15 Yale St, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
21 Bellevue Avenue, Winchester
$2,650,000
5 Beds ⋅ 4 Baths ⋅ 73506730 MLS
Exquisite home nestled in sought after Winchester neighborhood! This breathtaking home checks all the boxes on the wish list! Welcoming sun-filled entry foyer, soaring ceilings, gleaming hardwood floors & open concept flow. Inviting living room w/gas fireplace. Fabulous gourmet kitchen complete w/ Viking appliances, walk-in-pantry, dining area, coffee/wet bar & wine chiller. Sliding doors open to deck w/ serene wooded views overlooking level fenced in backyard. Elegant dining room, Family room w/stone fireplace adjacent to in-law or home office suite w/lush bath & separate entrance. Second floor offers luxurious master suite featuring spa-like marble bath w/oversized shower & soaking tub, dressing room, office nook & private deck retreat. 3 additional generous sized bedrooms w/ensuite baths & laundry room. Lower level features a spacious media/game room that opens to backyard & mudroom w/ direct access to oversized 2 car garage/work space. Highest quality systems & finishes throughout!

21 Bellevue Avenue, Winchester

Listing courtesy of Listing Agent: Giordana Fioravanti Smith from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
45 Bacon Street, Winchester
$2,650,000
7 Beds ⋅ 8 Baths ⋅ 73479961 MLS
Situated at the corner of Ginn Road neighborhood, this home was custom built by a premier local builder- with its dramatic design, it is a must see! Ideally located near town center w/ easy access to the commuter rail, Mystic lakes trails & beach, Ginn playground & the vibrant town center. This 7000sf, 7 BR home is perfectly designed for todays living w/ au-pair & multi generational options. A dramatic two-story foyer with stunning lit cove ceiling welcomes you into the home & flows into the formal living and dining spaces. The oversized chef’s kitchen features high end cabinetry, top-tier stainless appliances, large granite island w/dining area & fireplace. The inviting family room is just off the kitchen;The primary suite offers a lavish walk-in closet, large bath w/radiant heat & steam shower. Four additional bedrooms include en-suite baths, plus a separate-entry au pair suite. The finished lower level includes a bar, flexible family room/bonus space, gym & storage. Floor plan att'd

45 Bacon Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
2 Priscilla Lane, Winchester
$2,649,000
4 Beds ⋅ 4 Baths ⋅ 73485423 MLS
Under construction / Beautifully crafted 4 bedroom home offering thoughtful design, quality finishes & an ideal layout. The open-concept 1st floor is both spacious & welcoming, perfect for entertaining & everyday living. The chef’s kitchen features quartz countertops, stainless appliances, large center island w/seating & pantry. The kitchen flows seamlessly into the generous family room w/ gas fireplace & sliders leading to a large deck w/ private yard. The main level also includes a formal dining room w/ wainscoting, & a tray ceiling, a functional mudroom w/ bench seating, & a stylish half bath. Upstairs, the expansive primary suite offers 2 walk-in closets a luxurious bath with double vanities, soaking tub, & oversized shower. 3 additional bedrooms, a full hall bath, & convenient laundry room complete the 2nd floor. The finished LL provides a versatile media room,a full bath, & abundant storage. Two-car garage w/ direct entry. Convenient location close to town, train & Boston!

2 Priscilla Lane, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
10 Sheffield Road, Winchester
$2,630,000
7 Beds ⋅ 6 Baths ⋅ 73383662 MLS
This stunning Colonial Revival home, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master suite with walk-in closets and a Jacuzzi bath, along with two additional bedrooms and an updated bathroom. The third floor offers a variety of flexible living spaces: one separate bedroom with an en suite, one study that can share the en suite as a separate bedroom, and one suite/bedroom with a bath, morning kitchen area, and living room. The finished basement is equipped with a wet bar and wine cellar. Outside, a new two-car garage, storage shed, and patio/deck enhance the generous lot. Recent upgrades include kitchen, porch, HVAC, electrical systems, IT wiring, and beautiful wood flooring.

10 Sheffield Road, Winchester

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

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