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100 Westcliff Rd, Weston
$3,500,000
6 Beds ⋅ 7 Baths ⋅ 73480059 MLS
Private waterfront estate on the Wellesley/Weston line! Enjoy nearly 9,000 sq ft of elegant, sun-filled living with breathtaking views of Pierce Pond from almost every room. This custom Southside Weston home blends sophisticated architectural detail with modern updates and a flexible layout ideal for today’s lifestyle. Features include a dramatic foyer, gourmet chef’s kitchen with Wolf & Sub-Zero appliances, and six en suite bedrooms including a serene primary suite with spa-like bath and dual walk-in closets. Multiple rooms offer options for offices, gym, or guest space. Expansive terraces and decks overlook lush landscaping and the tranquil pond. With five fireplaces, artisan millwork, and a three-car garage, this property offers a rare combination of privacy, beauty, and convenience just minutes to Wellesley, Weston Center, and Boston.

100 Westcliff Rd, Weston

Listing courtesy of Listing Agent: Donahue Maley and Burns Team from Listing Office: Compass.
19 Old Road, Weston
$2,160,000
4 Beds ⋅ 5 Baths ⋅ 73505150 MLS
Beautifully renovated contemporary in one of Weston’s most sought-after neighborhoods, just moments from the town center and scenic trails. The sun-drenched open-concept main level features a stunning updated kitchen with quartz countertops and backsplash, an oversized island, and sleek cabinetry, flowing seamlessly into a three-season screened porch and expansive decks overlooking a private, tree-lined yard. A fireplaced living room, flexible first-floor bedroom, and full bath complete the main level. Upstairs offers three generously sized bedrooms, including a luxurious primary suite with cathedral ceilings, a spa-like bath, walk-in closet, private deck access, and a dedicated office alcove. The finished walk-out lower level, anchored by a fireplaced family room. Additional highlights include a heated two-car garage plus an additional covered parking space, central air, hardwood floors, and abundant storage. Enjoy Weston schools with easy access to major routes & commuter rail.

19 Old Road, Weston

Listing courtesy of Listing Agent: Wei Wenny Fu from Listing Office: Phoenix Real Estate.
16 Livermore Lane Unit 16, Weston
$1,750,000
3 Beds ⋅ 4 Baths ⋅ 73482620 MLS ⋅ ['Dickson Meadow'] BLDG.
Rarely available freestanding townhouse showcasing a spacious, thoughtfully designed floor plan, sweeping views, and an unbeatable location just moments from Weston Center and miles of hiking trails. Designed for everyday living and effortless entertaining, the chef’s kitchen flows seamlessly into a dramatic cathedral-ceiling family room anchored by a gas fireplace. Sliding doors open to an expansive deck, creating exceptional indoor-outdoor living. The luxurious first-floor primary is a private retreat, complete with a full bath and two walk-in closets. Upstairs, two generously sized bedrooms and another full bath provide comfortable accommodations for family or guests. Hardwood floors, central air, a whole house generator and an EV outlet in the garage add modern convenience. The finished walk-out lower level offers an expansive game room, half bath, and abundant storage. A screened porch offers protected outdoor enjoyment. An exceptional opportunity to enjoy low-maintenance living!

16 Livermore Lane Unit 16, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
27 Silver Hill, Weston
$2,499,000
5 Beds ⋅ 5 Baths ⋅ 73499783 MLS
Fabulous colonial in a coveted Weston neighborhood, this beautifully maintained home offers the perfect blend of timeless charm and modern convenience. Thoughtfully updated in 2020, the kitchen and bathrooms showcase stylish finishes, quality craftsmanship, and today’s most sought-after features. The light-filled interior features a functional and inviting layout with generous living spaces, seamlessly connecting indoors and out. The updated kitchen serves as the heart of the home with adjoining family room and spacious screened in porch. Sited on a picturesque acre, this property provides both privacy and accessibility, just moments to Weston Center, top-rated schools, and major commuting routes. A turnkey opportunity to enjoy one of Weston’s most desirable locations.

27 Silver Hill, Weston

Listing courtesy of Listing Agent: Deena Powell from Listing Office: Gibson Sotheby's International Realty.
55 Forest Ridge Road, Weston
$2,600,000
4 Beds ⋅ 4 Baths ⋅ 73486160 MLS
Turnkey Colonial blending luxury, comfort, and convenience with thoughtfully designed interiors, set on a sought-after cul-de-sac. A grand foyer leads to an updated kitchen featuring quartz countertops, stainless appliances, abundant cabinetry and a large island, opening seamlessly to a family room with soaring ceiling and direct access to an expansive patio. A formal living room with fireplace and a gracious dining room provide elegant spaces for gatherings. Upstairs, the impressive primary offers a vaulted ceiling, spa bath and walk-in closet, plus three additional bedrooms, a full bath, and convenient 2nd floor laundry. The finished 3rd floor adds a versatile bonus room with full bath, ideal for guests, office or playroom. All 4 baths are marble. An unfinished basement w/12’ ceilings offers excellent potential. The private, level backyard with charming gazebo creates a peaceful outdoor retreat. Ideally located near top schools, the commuter rail, bike path, shopping, & major routes.

55 Forest Ridge Road, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
169 Hickory Rd, Weston
$2,695,000
5 Beds ⋅ 3 Baths ⋅ 73478053 MLS
Rarely available, this beautifully updated contemporary home is set on over 1.4 acres in one of Weston’s premier South Side neighborhoods. Bathed in natural light and offering exceptional privacy, the property is surrounded by mature landscaping, gardens, a pool, fieldstone walls, and inviting patios that create a peaceful setting. Thoughtfully renovated with quality finishes throughout, the interior spaces are ideal for both entertaining and comfortable everyday living. The kitchen features European cabinetry, a generous center island, and premium appliances, and opens seamlessly to spacious living, dining, and family rooms. The home offers five well-proportioned bedrooms, including a serene primary suite with views of the landscaped grounds, a spa-like bath, and a walk-in closet. A fabulous walkout lower level provides outstanding additional space for recreation, gatherings, or a home gym, adding versatility to this special property.

169 Hickory Rd, Weston

Listing courtesy of Listing Agent: Dean Poritzky from Listing Office: Engel & Volkers Wellesley.
680 South Ave Unit 7, Weston
$1,560,000
3 Beds ⋅ 4 Baths ⋅ 73533030 MLS
Newbury-style townhouse tucked away in a private cul-de-sac setting, offering an exceptional blend of luxury, privacy, and convenience. The open floor plan features soaring ceilings, hardwood floors, a dramatic cathedral-ceiling living room with a gas fireplace, a sun-filled breakfast area, private office, and a desirable first-floor primary suite with a walk-in closet and spa-inspired marble bath. An expansive deck overlooks conservation land, creating a peaceful setting for outdoor enjoyment. The second level offers a versatile loft, three spacious rooms, and a full bath, providing flexibility for family, guests, or home office needs. The finished lower level adds over 1,000 square feet of living space with a full bathroom, ideal for recreation, media, fitness or entertaining. Thoughtfully updated throughout with a renovated kitchen, remodeled bathrooms, custom closets, and designer lighting. Conveniently located near top rated Weston public schoos, commuter rail, and the Mass Pik

680 South Ave Unit 7, Weston

Listing courtesy of Listing Agent: Yang Liu from Listing Office: Weston Realty LLC.
12 Fillmore Place Unit 12, Weston
$2,480,000
4 Beds ⋅ 4 Baths ⋅ 73510367 MLS ⋅ ['Highland Meadows'] BLDG.
Weston’s premier 55+ community offers luxury living with a maintenance-free lifestyle. This beautifully crafted home features 4 bedrooms, 3.5 baths, and approximately 3,250 sq ft across three finished levels designed for comfort and style. A welcoming two story foyer, a private home office and an open-concept living and dining room with custom built-ins, a gas fireplace, and sliders to a deck and patio. The cook’s kitchen boasts stainless steel appliances, abundant cabinetry, and a sunlit breakfast area with access to a deck showcasing scenic views. The first-floor primary with tray ceiling is a serene retreat with a luxe bath, walk-in closet, and private fenced patio. A half bath, laundry, and 2-car garage complete the main level. Upstairs offers a spacious bedroom, full bath, and versatile loft. The finished, walk out lower level includes a family room with fireplace, two additional bedrooms, a full bath, and generous storage. Enjoy a clubhouse, gym, tennis courts, and nearby trails.

12 Fillmore Place Unit 12, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
153 Ridgeway Rd, Weston
$3,750,000
5 Beds ⋅ 6 Baths ⋅ 73519385 MLS
Weston charm meets modern-day amenities at 153 Ridgeway Rd, a beautifully renovated historic residence set on 2.24 acres abutting conservation land & trails. Located in one of Weston’s most convenient location, this 5-bed home has been extensively renovated blending timeless character with modern updates.The reimagined & gracious floor plan features elegant entertaining spaces, updated kitchen, a great room with fireplace & wet-bar, playroom, mudroom with built-ins & finished lower-level gym. Add'l improvements include updated systems & baths, new windows & doors, refinished floors, interior & exterior painting & extensive landscaping.The primary suite with 2 walk-in closets features a fireplace & spectacular bath with octagon ceiling overlooking the park-like grounds.4 additional bedrooms and 3 updated baths complete the 2nd & 3rd floors.Outdoor spaces include a bluestone patio, deck, stone walls, gardens, fruit trees, treehouse, playground & an expansive yard! A rare Weston treasure!

153 Ridgeway Rd, Weston

Listing courtesy of Listing Agent: Felicia Captain from Listing Office: Coldwell Banker Realty - Wellesley.
76 Robin Rd, Weston
$9,290,000
5 Beds ⋅ 9 Baths ⋅ 73483740 MLS
Magnificently sited on over two acres with breathtaking views of Weston Golf Club, this young Shingle and Stone estate blends timeless architecture with modern sophistication. Designed by award-winning architect Patrick Ahearn, this custom beauty offers over 8,600 square feet of freshly updated, Architectural Digest–worthy interiors filled with natural light. Highlights include a dazzling chef's kitchen with an oversized island, a fireplaced office, four ensuite bedrooms plus a luxurious primary suite with a beautiful spa bathroom, and an adjacent sun deck. The lower level has tall ceilings, a fireplaced entertainment lounge, a gym, wine cellar, wet bar, playroom, and space for a golf simulator. Surrounded by rolling lawns, stone terraces, and long views over the 7th fairway, this exceptional property offers a rare opportunity to live in one of Greater Boston’s most coveted estate locations.

76 Robin Rd, Weston

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.
183 Conant Rd, Weston
$3,075,000
4 Beds ⋅ 5 Baths ⋅ 73489268 MLS
Stunning custom new construction in a prime Weston location offering 5,400+ sqft of thoughtfully designed living space. This gorgeous home features a flexible open floor plan with option for a 1st-floor bedroom or office. The chef’s kitchen boasts premium appliances, gas cooktop, custom cabinetry, and a large center island perfect for entertaining. The 2nd level includes 3 spacious bedrooms, den w/closet & 2 baths, highlighted by a luxurious primary suite with spa-like bath and walk-in closets. A bright walk-out lower level with full bath provides ideal space for a media room, gym, or guest suite. Enjoy a private backyard with patio, deck, and serene conservation views. Conveniently located close to town, top-rated schools, shopping, and major routes!

183 Conant Rd, Weston

Listing courtesy of Listing Agent: Gabby Cefalo from Listing Office: Coldwell Banker Realty - Wellesley.
40 Bakers Hill Rd, Weston
$1,620,000
3 Beds ⋅ 3 Baths ⋅ 73485991 MLS
Set on a spectacular, level lot in one of Weston’s most popular neighborhoods, this beautifully maintained home offers exceptional space, comfort, and versatility. The sun-filled main level features an updated kitchen with granite countertops and stainless steel appliances, seamlessly connecting to an elegant dining room, expansive living room with picture window, and inviting sunroom. The private sleeping wing includes three generously sized bedrooms and two full baths, ideal for relaxation and functionality. The finished lower level adds valuable bonus space with a spacious playroom, private home office, laundry and full bath. An exceptional indoor pool elevates this home to the next level! Additional highlights include a two-car garage, abundant storage, central air, and hardwood floors. Ideally located with sidewalks to the commuter rail, close to miles of conservation trails, and offering access to top-rated Weston schools, this special property is a wonderful place to call home.

40 Bakers Hill Rd, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
1 Pine Summit Unit 1, Weston
$3,475,000
3 Beds ⋅ 4 Baths ⋅ 73472907 MLS ⋅ ['Highland Meadows'] BLDG.
Curated style and luxury to be found at 1 Pine Summit Circle. This spacious, stand alone condominium features an open floor plan, fabulous great room, private first floor primary suite with luxurious bath, study, and two walk in closets. The great room opens to a true cook's kitchen and is the heart of the home. A gas fireplace with marble surround, generous breakfast area, access to a private deck and screen porch are just a few of the many elegant features of this home. Utility/laundry, pantry and closet create a mud room that leads to the garage.Extensive millwork and high end finishes are found throughout.Two guest bedrooms ensuite on 2nd floor, and lower level is walkout with a large family room, office, flex room and extensive storage. Full house generator. Highland Meadows is located in a serene country environment and affords community enjoyment with a clubhouse,exercise facility, yoga studio,tennis and pickleball courts. Walking distance to charming Weston Center

1 Pine Summit Unit 1, Weston

Listing courtesy of Listing Agent: Leeann Yolin from Listing Office: Coldwell Banker Realty - Weston.
41 Skating Pond Road, Weston
$6,225,000
5 Beds ⋅ 9 Baths ⋅ 73512781 MLS
Privately set on 2.42 acres in Weston’s highly coveted South Side Country Club area, 41 Skating Pond Road offers over 11,000 sf of exceptional living space, recently renovated to the highest standard of fit & finish. The residence features 5 en suite bedrooms, 7 full baths, 2 half baths & attached 3 car garage. A dramatic 2 story foyer fills the home with natural light, while refined interiors include a sun filled solarium with windows on 3 sides. The award winning Christopher Peacock kitchen anchors the home, complemented by bespoke interiors by acclaimed designer Eric Roseff. A separate entry, commercial grade caterer's kitchen enables effortless entertaining on a grand scale. Additional amenities include private office, gym, sauna, steam room & climate controlled wine room. Ideally located near top Weston schools with convenient access to Rte. 128, the Mass Pike, Hanscom Field, downtown Boston & Logan Airport, this meticulously maintained estate offers a rare, turnkey opportunity.

41 Skating Pond Road, Weston

Listing courtesy of Listing Agent: Collin Sullivan from Listing Office: William Raveis R.E. & Home Services.
48 Sunset Rd, Weston
$2,850,000
5 Beds ⋅ 4 Baths ⋅ 73491547 MLS
48 Sunset Road — a beautifully updated home, in one of Weston’s most coveted neighborhoods. The open-concept layout is filled with natural light and designed for refined modern living. The chef’s kitchen features high-end appliances, including a Thermador gas range, Sub-Zero refrigerator, and oversized quartzite island, flowing seamlessly to the family and dining rooms. First floor also includes an expansive mudroom, office, full bath, and formal living room. Upstairs are four bedrooms, including a primary suite with a newly updated en-suite bath. The lower level offers additional flexible space for recreation. Finished living space above the garage is ideal for an in-law or au pair suite, home office, or private gym. The fenced backyard, with multiple decks and patios, provides privacy and serene views. Located near top-rated schools, town amenities and trails, this move-in-ready home combines elegance and comfort in an unbeatable neighborhood.

48 Sunset Rd, Weston

Listing courtesy of Listing Agent: Jonathan Caldwell from Listing Office: ACRE Property Advisors LLC.
286 Country Dr, Weston
$7,180,000
6 Beds ⋅ 8 Baths ⋅ 73474235 MLS
This custom-built modern estate sits prominently on a 1.42-acre corner lot and pairs striking architectural design with uncompromising craftsmanship across ~8,421 SF and 3 curated levels. A dramatic entry welcomes you into a soaring foyer anchored by a sculptural staircase and statement lighting, setting the tone for the home’s sophisticated aesthetic. Expansive floor-to-ceiling glass floods each room with natural light, revealing serene garden views, multiple lounge and entertaining spaces, and seamless indoor–outdoor flow. Every detail designed for both elevated hosting and effortless everyday living: 6 ensuite bedrooms, custom closet systems, dedicated office spaces, a gaming room, gym, sauna, and expansive family + bonus rooms provide unmatched flexibility. Outdoor amenities include a roof-deck terrace, private tennis court, lush gardens, and full plans in hand for a future pool. A 3-car garage, solar integration, and a complete Savant smart-home system further elevate this home!

286 Country Dr, Weston

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.
77 Brook Rd, Weston
$1,525,000
3 Beds ⋅ 3 Baths ⋅ 73514045 MLS
Introducing this charming 1891 farmhouse, offering comfortable and stylish living across three thoughtfully designed floors. A welcoming farmer’s porch sets the tone, inviting you into this warm and character-filled home. Located on a quiet street in one of Weston’s most beloved neighborhoods, the property perfectly blends historic charm with everyday comfort. Inside, the home features inviting living spaces, rich character, and a lovely three-season porch perfect for relaxing or entertaining. The second floor is comprised of a spacious primary suite and two additional bedrooms. The third-floor bonus room features custom built-in beds and a private balcony overlooking the backyard, creating an ideal retreat for guests, a playroom, or additional living space.An additional barn offers tremendous potential for storage, studio space, hobbies, or future expansion. Adding to the home’s unique setting is an open field located directly across the street, enhancing the sense of space.

77 Brook Rd, Weston

Listing courtesy of Listing Agent: Karen Kirk from Listing Office: Engel & Volkers Wellesley.
51 Wellesley Street, Weston
$1,650,000
4 Beds ⋅ 3 Baths ⋅ 73508588 MLS
This lovingly maintained single-family home is set on a 0.31-acre lot in one of Weston’s most desirable locations. This 4-bedroom, 2.5-bath residence offers 2,152 square feet of light-filled living space with a thoughtful, easy flow that suits both daily living and entertaining. Sunlight fills the home, highlighting warm hardwood floors and inviting, well-proportioned rooms. The main level features a spacious formal living room, formal dining area, and a well-appointed kitchen that connects seamlessly to another living area and out to the patio. Upstairs, four comfortable bedrooms and two full baths offer flexibility for family, guests, or a home office. Outside, the private backyard provides a peaceful setting for dining, play, or quiet afternoons, while a detached two-car garage adds convenience and storage. Ideally located near Weston’s schools, conservation land, and town center, with easy access to commuting routes, this home offers a wonderful balance of comfort and setting.

51 Wellesley Street, Weston

Listing courtesy of Listing Agent: Adams & Co. Team from Listing Office: Real Broker MA, LLC.
157 Oak Street, Weston
$3,100,000
4 Beds ⋅ 3 Baths ⋅ 73501674 MLS
Experience Vermont-style craftsmanship in this unique post-and-beam home on a nearly 3 acre, wooded Weston estate. Step inside to find light-filled living spaces framed by rich woodwork, vaulted ceilings & floor-to-ceiling windows. The open-concept main level features wide-board pine floors & a dramatic 2-story great room anchored by an ornate gas stove. A spacious kitchen with a stone island leads to a dining room for entertaining. The first-floor primary suite is a retreat with an en-suite bath and dual walk-in closets. This level also has a guest bedroom, office, mudroom & 2-car attached garage. Upstairs, find 2 oversized bedrooms & a sun-drenched family room. Enjoy the farmer’s porch, rear deck & path to the Norumbega Resevoir. A show-stopping barn offers oversized 3 garage parking & a versatile second-floor apartment with full bathroom. This private escape is minutes from top schools, Route 128 & Mass Pike. A unique, warm & quintessential New England gem close to Boston.

157 Oak Street, Weston

Listing courtesy of Listing Agent: Chris Vietor Homes from Listing Office: eXp Realty LLC.
199 Country Rd, Weston
$2,480,000
6 Beds ⋅ 4 Baths ⋅ 73499437 MLS
This modern Cape offers exceptional space and style. The home's design is enhanced with a saltwater pool, a large finished basement and adjoining pool house. The open floor plan is filled with natural light from oversized windows and showcases gleaming hardwood floors throughout. The newer kitchen is a chef’s dream, equipped with Sub-Zero, Miele, and Wolf appliances, a large island, breakfast bar, and spacious eat-in area. The grand living room is perfect for entertaining and family gatherings. The first floor also includes three generously sized bedrooms and a formal dining room that opens to a deck overlooking the private, expansive yard and pool. A sophisticated and luxurious primary suite and two additional bedroom with bath are located upstairs. This contemporary home is situated in Weston Estates, one of the town's most desirable neighborhoods. Convenient access to walking trails, top-ranked Weston schools, and all major transportation routes to Boston.

199 Country Rd, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.
7 Longmeadow Road, Weston
$1,330,000
3 Beds ⋅ 3 Baths ⋅ 73514364 MLS
Located in a highly desirable Northside neighborhood in Weston, this charming ranch-style home offers exceptional potential.Featuring threebedrooms and a four-bedroom septic system,the property presents a wonderful opportunity to expand or enjoy as is. The home boasts a bright, open living and dining area centered around a striking two-sided fireplace ideal for both everyday living and entertaining. A newer, generously sized primary suite includes access to a private deck, creating a private retreat. The lower level offers versatile additional space perfect for a playroom, gym, or abundant storage. Ideally situated close to Weston Town Center, top-rated schools, and major commuting routes, this home combines comfort, convenience, and future potential.

7 Longmeadow Road, Weston

Listing courtesy of Listing Agent: Deena Powell from Listing Office: Gibson Sotheby's International Realty.
9 Sanderson Ln, Weston
$4,900,000
5 Beds ⋅ 8 Baths ⋅ 73472249 MLS
Tucked away on one of Weston’s most coveted culdesacs, this stunning 5 bedroom Colonial will steal your heart. Renovated both inside and out in the last few years including a new roof and heating system, the home offers soaring ceilings, grand proportions. A formal two story entry flanked by entertainment sized dining room with butler pantry and fire placed livingroom large enough for a crowd leads to a handsome fireplaced library and music room which can double as a second office. The stunning eat in chef’s kitchen leads to a screened in porch and family room with majestic stone fireplace and walls of windows all overlooking the newly landscaped grounds. Upstairs, there are four good sized ensuite bedrooms, including a luxurious primary suite and spa bath. The fully finished basement features a gym, media room, recreation room and bath. All of this sited on a level private lot with its own magical in ground pool oasis complete with fully equipped pool house and jacuzzi.

9 Sanderson Ln, Weston

Listing courtesy of Listing Agent: Donahue Maley and Burns Team from Listing Office: Compass.
43 Sherburn Cir, Weston
$1,700,000
3 Beds ⋅ 3 Baths ⋅ 73510763 MLS
Sited in a terrific South Side neighborhood and set way back off an idyllic residential street at the crest of a hill, you'll find this attractive home built in 1961. Highlighting the main level is the updated, bright kitchen with vaulted ceilings and 2 oversized skylights. There is plenty of room for your sit down breakfast table, and there is direct access outside to a lovely flagstone patio for those warmer nights. Overlook the deep back yard from the picture window in the dining room, which opens to a bonus sitting room or den, also with an outdoor view. The oversized 21' LR overlooks the cherry tree & Dogwood by the front entry. 3 generous bedrooms and 2 1/2 tiled baths complete the main level. The lower level features a huge family room with fireplace, recessed lights & nicely laid ceramic plank flooring. There is a bonus office nearby, as well as a half bath and direct access to the 2 car gar. The expansive grounds offer options to expand.

43 Sherburn Cir, Weston

Listing courtesy of Listing Agent: Ed Lyon from Listing Office: Preservation Properties.
419 Wellesley St, Weston
$3,560,000
5 Beds ⋅ 5 Baths ⋅ 73515393 MLS
A classic Tudor Colonial gracefully set on 5 private acres,offering 5 bedrooms, 4 full & 3 half baths, and 5,372 sqft across two expansive levels. Ideally sited at the end of a cul-de-sac in one of the area’s most desirable locations,the home is designed for both everyday living and elegant entertaining, featuring formal living and dining rooms, a private office,a gracious, inviting front staircase, and a kitchen that opens to a spacious family room, along with access to a screened porch. The primary suite offers a private sitting area,creating a peaceful retreat, while four additional bedrooms are complemented by two Jack-and-Jill baths on the second floor. A walk-up third floor provides excellent potential for additional living space. An oversized 3-bay garage provides direct access to the lower level. The grounds unfold into a private backyard oasis with a large, beautifully landscaped yard, sports court,fire pit, & hot tub—all in close proximity to Weston’s top rated schools.

419 Wellesley St, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.
823 Boston Post Road, Weston
$1,972,500
5 Beds ⋅ 3 Baths ⋅ 73475182 MLS
Hayfields, a charming country estate, offers thoughtfully restored 1750's farmhouse, 5 stall barn with attached 2 car garage, heated 19x12 exercise/art studio, and additional 2 car garage with extra farm equipment storage bay all set on 2.21 acres. Updated for modern living, this 5 bedroom home offers formal living room, dining room with vaulted ceilings, bar, fieldstone fireplace looking out over patio and English Gardens. Country Kitchen with island, stainless steel appliances, pantry and eat-in-area, connects to family room.1st floor Bd. with fireplace. Home office. Primary suite with walk in closet/dressing room & luxurious bath. 3 additional Bds, one with balcony, and laundry complete the 2nd floor. Basement with 700 bottle barreled ceiling wine cellar and 2nd laundry. Hardwood floors. Generator, Cedar roof. Abutting miles of trail corridors on town conservation land. Great commuter location. Top Rated Weston Schools.

823 Boston Post Road, Weston

Listing courtesy of Listing Agent: Chaplin Partners from Listing Office: Compass.
9 Atlas Lane, Weston
$25,825,000
6 Beds ⋅ 8 Baths ⋅ 73400433 MLS
Introducing this Frank Llyod Wright inspired one-of-a-kind gem designed by award winning AD 100 architect, Thomas Catalano. Ultimate privacy on a 6+ acre property, adjacent to the Weston Reservoir, this estate cultivates the symmetry of nature with meticulously curated interiors. Galvanized steel finishes fuse the interior rooms with the exterior heated courtyards. Each space pays homage to its analogous setting from the glass window encased hallway to the elegant "El Grotto" which serves as the pool house. It is complemented by a fitness center, massage room, sauna, wine and game rooms. A luxurious primary suite has a sitting room with a fireplace, crafted marble bathroom and balcony with outdoor shower that has views of rolling meadows.The remarkable grounds are a backdrop for an infinity pool, hot tub and waterfall. This unique residence transports you to a faraway place, but in reality is located just minutes from Boston in one of New England's most exclusive towns.

9 Atlas Lane, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.
24 Sears Road, Weston
$3,750,000
5 Beds ⋅ 5 Baths ⋅ 73501865 MLS
Set in a coveted estate neighborhood, this exceptional custom Colonial seamlessly blends timeless elegance with modern living. The home is anchored by a chef’s kitchen with an expansive island that flows seamlessly into the family room with a vaulted ceiling and fireplace. Formal living and dining rooms provide the perfect backdrop for hosting. Upstairs are five generously sized bedrooms, including a primary retreat with spa bath and impressive walk-in closet. There are also two home office options, a screened-in porch and a finished third floor with skylight and playroom. The lower level offers exceptional versatility with a game room, gym, full bath and abundant storage. Recent updates, including a new roof (2025) and heating system (2023), ensure peace of mind. Outside, the beautifully landscaped, fenced grounds feature a pool, deck, and patio. A three-car garage completes this distinguished offering. Enjoy top Weston schools, easy commuting, miles of trails, and sidewalks to town!

24 Sears Road, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
64 Oak Street, Weston
$2,750,000
4 Beds ⋅ 6 Baths ⋅ 73491863 MLS
Exceptional young Colonial ideally set in a premier South Side neighborhood, offering a seamless blend of luxury, comfort, and everyday convenience. The open floor plan showcases soaring ceilings, custom millwork, and rich hardwood floors, creating a warm yet elegant atmosphere. The chef’s kitchen is the heart of the home, featuring a sunlit breakfast area, butler’s pantry, and effortless flow into the inviting family room with custom cabinetry. A formal living room with fireplace and coffered ceiling, and an elegant dining room, provide refined spaces for entertaining. A private home office is ideal for remote work or study. Upstairs offers four ensuite bedrooms, including a luxurious primary suite with spa bath and walk-in closet, plus a versatile third-floor bonus room. The finished lower level includes a spacious playroom with fireplace, gym, and full bath. Walls of windows overlook picturesque grounds with a terraced patio. Convenient to highways, commuter rail, and town centers.

64 Oak Street, Weston

Listing courtesy of Listing Agent: Denise Mosher from Listing Office: Coldwell Banker Realty - Weston.
3 Idlewile Lane, Weston
$9,739,680
6 Beds ⋅ 11 Baths ⋅ 73506302 MLS
Set behind gates on more than 8 acres in Weston’s prestigious south side, this extraordinary estate abuts protected conservation land, offering rare privacy and natural seclusion. Spanning over 14,000 square feet, the residence is distinguished by soaring ceilings, finely detailed custom millwork, Venetian plaster, and imported stone—crafted to exacting standards throughout. Gracious yet functional interiors include an expansive chef’s kitchen, elegant formal living and entertaining spaces, executive office, and a banquet-scale dining room. The upper level features a serene primary suite with dual dressing rooms and spa bath, along with five additional ensuite bedrooms. A resort-style lower level delivers world-class amenities, including an indoor lap pool, half basketball court, theater, spa, gym, and bunk room. An elevator, whole-house generator, and 7-car heated garage with four EV chargers complete this private legacy estate of enduring distinction.

3 Idlewile Lane, Weston

Listing courtesy of Listing Agent: Collin Sullivan from Listing Office: William Raveis R.E. & Home Services.
556 Wellesley Street, Weston
$1,710,000
4 Beds ⋅ 3 Baths ⋅ 73489556 MLS
Iconic front porch welcomes you into this charming circa-1901 farmhouse. The front foyer opens to gracious living and dining rooms with a fireplace. Updated kitchen and family room with plenty of storage and easy access to a deck overlooking a flat backyard with patio and play area. The second floor offers a primary suite with vaulted ceilings and an en suite bath, three additional bedrooms, and access to a finished bonus room on the third floor. Newly refinished hardwood floors throughout all formal first-floor areas. Lower level features space for an exercise area, a storage closet, and easy access to the backyard. Two-car garage with loft. Top-rated Weston Schools.

556 Wellesley Street, Weston

Listing courtesy of Listing Agent: Chaplin Partners from Listing Office: Compass.

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