Homes for Sale near Weston High School

/40
$3,985,000

Open Sat 1PM - 2PM $265K PRICE DROP
- 4 Beds
- 6 Baths
- 5,018 Sq Ft
105 Summer St, Weston, MA 02493

Unmatched quality and craftsmanship define this architecturally inspired new home. Maple wood floors, cherry paneled walls and expansive German triple-glazed windows create its curated aesthetic. An expertly designed kitchen with a huge island, custom window seat, and generous dining area open seamlessly to the family room anchored by a striking marble fireplace. The first floor primary suite

Mizner+ Montero Gibson Sotheby's International Realty

105 Summer St, Weston, MA 02493
Explore Weston High School
/40
$4,680,000
- 6 Beds
- 6.5 Baths
- 7,658 Sq Ft
83 Brown St, Weston, MA 02493

This recently built custom home presents a modern design and refined detail. A dramatic two-story foyer and the open family room make an immediate statement. The dining room complements the open and airy floor plan with beautiful hardwood floors and soaring ceilings The stylish kitchen features a large center island, wet bar, and spacious dining area opening to a sun-filled family room accented

Mizner+ Montero Gibson Sotheby's International Realty

83 Brown St, Weston, MA 02493
/34
$4,995,000

$255K PRICE DROP
- 5 Beds
- 8 Baths
- 6,338 Sq Ft
9 Skating Pond Rd, Weston, MA 02493

Reimagined & redesigned stunning custom home on over 1 acre in Weston's prestigious Golf Club neighborhood. New layout, new floors, new custom built-ins, new kitchen, new butler pantry, new bathrooms, new moudings, white oak door trim, new furnaces, new AC condensers, new Marvin windows, new stone walls & landscaping...... Kitchen family room w/ breakfast nook opens to large family room w/

Melissa Dailey Coldwell Banker Realty - Wellesley

9 Skating Pond Rd, Weston, MA 02493
/37
$3,850,000
- 5 Beds
- 5.5 Baths
- 6,700 Sq Ft
21 Bemis St, Weston, MA 02493

Incredible combination of stunning home with incredible land. Custom 5 bedroom home with over 6700 sq of living space with 12 ft ceilings! Designer kitchen with exposed beams create a unique and warm feeling. Open concept kitchen family room is filled with sunlight. Huge walk-in pantry. Large living room and dining room perfect for entertaining. Incredible cypress wood home office with floor to

Melissa Dailey Coldwell Banker Realty - Wellesley

21 Bemis St, Weston, MA 02493
/42
$6,495,000

Open Sat 11AM - 12:30PM
- 5 Beds
- 7.5 Baths
- 8,329 Sq Ft
82 Deer Path Ln, Weston, MA 02493

Set privately on 2.08 acres with a graceful, tree-lined approach, 82 Deer Path Lane offers a fully reimagined home where natural light, timeless detailing, and expansive indoor-outdoor living shine. Beautiful millwork and refined molding enhance the main living spaces, including a dramatic great room with soaring ceilings and panoramic views of the large, flat backyard, with patios and deck—ideal

Jonathan Caldwell ACRE Property Advisors LLC

82 Deer Path Ln, Weston, MA 02493
/41
$6,750,000
- 6 Beds
- 9 Baths
- 11,330 Sq Ft
448 & 454 Concord Rd, Weston, MA 02493

A rare and exceptional six bedroom estate is complemented by a 3 bedroom shingle style guest cottage. With timeless architectural appeal, the home showcases unsurpassed craftsmanship, meticulous attention to detail and curated finishes throughout. The first floor welcomes you with the grand foyer's dramatic staircase, a richly appointed mahogany-paneled library, and elegant formal living and

Mizner+ Montero Gibson Sotheby's International Realty

448 & 454 Concord Rd, Weston, MA 02493
/28
$4,800,000
- 5 Beds
- 6.5 Baths
- 12,144 Sq Ft
451 Wellesley St, Weston, MA 02493

Set on 5.6 private acres on Weston’s highly desirable south side, this impressive estate offers exceptional privacy and timeless appeal. Tucked at the end of a long, winding driveway, this Federal Colonial blends classic architecture with comfortable living, featuring sun-filled interiors, a dramatic two-story family room with fireplace, a bright sunroom, and a stylish home office. The flexible

Yang Liu Weston Realty LLC

451 Wellesley St, Weston, MA 02493
/42
$6,999,000

$599K PRICE DROP
- 6 Beds
- 10 Baths
- 9,000 Sq Ft
56 Cart Path Rd, Weston, MA 02493

Exquisite cape colonial estate in Weston’s golf club area. Perfect location on 2.85 acres in Weston's top neighborhood. Two floor grand foyer opens to the coffered great room, drenched in light from the floor to ceiling windows and the patio doors, which open out to the massive deck overlooking the large, flat, private back yard, while the grand fireplace and custom millwork impress. Large chef’s

Rose Hall Blue Ocean Realty, LLC

56 Cart Path Rd, Weston, MA 02493
/42
$3,750,000

Open Sun 12PM - 2PM
- 5 Beds
- 6 Baths
- 5,387 Sq Ft
153 Ridgeway Rd, Weston, MA 02493

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

Felicia Captain Coldwell Banker Realty - Wellesley

153 Ridgeway Rd, Weston, MA 02493
/39
$3,750,000

Open Sat 11AM - 12PM
- 7 Beds
- 7 Baths
- 6,710 Sq Ft
64 Country Dr, Weston, MA 02493

Stately brick-front Colonial in Weston Estates set on a spectacular 2.45 acres. A foyer with a gracious staircase opens to a front-to-back living room with a fireplace and a formal dining room. The newly renovated kitchen with a bright breakfast area opens to a sun-drenched sunroom overlooking the idyllic grounds with a waterfall and Koi pond. An inviting family room with a fireplace, mudroom and

Mizner+ Montero Gibson Sotheby's International Realty

64 Country Dr, Weston, MA 02493
/42
$3,795,000

Open Sat 11AM - 12:30PM
- 4 Beds
- 5.5 Baths
- 5,126 Sq Ft
55 Oakdale Ave, Weston, MA 02493

Architecturally designed, this 2024 modern farmhouse is beautifully sited on a level lot in the coveted south side of Weston. This thoughtfully 4 bed/5.5 bath Single Family is crafted with custom finishes across three levels, the sun-drenched open floor plan features 9' ceilings, crown moldings, and seamless flow. The chef’s kitchen offers custom cabinetry, Quartz “Blue Savoi” countertops, and a

Christman Johnsson Group Hammond Residential Real Estate

55 Oakdale Ave, Weston, MA 02493
/38
$4,595,000

$400K PRICE DROP
- 6 Beds
- 7 Baths
- 7,000 Sq Ft
21 Westerly Rd, Weston, MA 02493

1.38 acres of flat land in coveted Weston Estates! Stunning shingle and stone 6 bedroom Colonial. Extraordinary outdoor space featuring a pavilion with kitchen plus stone fireplace perfect for outdoor living and entertaining. Large kitchen with oversized island and seating area opens to double storeyed family room along with beautiful floor to ceiling stone fireplace, wet bar and incredible

Melissa Dailey Coldwell Banker Realty - Wellesley

21 Westerly Rd, Weston, MA 02493
/38
$4,388,000

$300K PRICE DROP
- 5 Beds
- 7 Baths
- 8,844 Sq Ft
568 Wellesley St, Weston, MA 02493

Elegant Custom Estate on 1.8 Acres in Weston! This stunning 8,000+ sq ft Colonial sits on a beautifully landscaped, level 1.8-acre lot with a private drive and circular entry. Inside, a grand foyer with a sweeping staircase opens to formal living and dining rooms with soaring ceilings, crown moldings, and French doors. The gourmet kitchen with marble countertops, super high-end & branded

Rose Hall Blue Ocean Realty, LLC

568 Wellesley St, Weston, MA 02493
/34
$4,150,000

Open Sun 3PM - 4:30PM $275K PRICE DROP
- 5 Beds
- 6.5 Baths
- 8,500 Sq Ft
11 Winthrop Cir, Weston, MA 02493

An award-winning architect brings sophisticated modern design to Weston at 11 Winthrop Circle. This extraordinary home offers 8,500 sq. ft. of sun-filled living space with an open floor plan, expansive windows, and beautiful contemporary mill work. The Poggenpohl kitchen flows seamlessly into a stunning family room with fireplace, perfect for everyday living and entertaining. Elegant living and

Sheryl Simon Gibson Sotheby's International Realty

11 Winthrop Cir, Weston, MA 02493
/31
$1,849,000

Open Sun 11AM - 1PM $401K PRICE DROP
- 4 Beds
- 3.5 Baths
- 3,013 Sq Ft
302 Concord Rd, Weston, MA 02493

Exceptional Victorian elegance on 1.42 picturesque acres abutting the Jericho Town Forest. This architecturally significant home is defined by stunning period details, dual staircases, and a sun-filled conservatory. A rare highlight is the separate, heated carriage house with a kitchenette and full bath—whether you envision a private guest wing, a sophisticated home office, or a creative studio,

Betsy Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

302 Concord Rd, Weston, MA 02493
/32
$1,475,000

$24K PRICE DROP
- 3 Beds
- 3 Baths
- 2,950 Sq Ft
786 Boston Post Rd, Weston, MA 02493

Opportunity knocks! Don't miss this classic, updated 1940's colonial on almost an acre of land w/separate attached office space, perfect for potential first floor primary renovation or your at-home business! The sun-filled main home has a classic center entrance, front to back living room w/wood burning fireplace, formal dining room w/built in hutch, a bright, updated kitchen open to family room

The Allain Group Compass

786 Boston Post Rd, Weston, MA 02493
/42
$9,990,000

$510K PRICE DROP
- 5 Beds
- 10 Baths
- 11,352 Sq Ft
70 Possum Rd, Weston, MA 02493

This peerless modern 2-acre estate is located in a highly desired private neighborhood in Weston. Exterior features a beautiful, flat landscaped yard, patio w/grill, and a full sports court. The luxurious 5 bed, 7f/3h bath interior features lofty 12’ high ceilings with walls and ceilings of glass, opening the space to the exterior and drenching this home in sunlight. Smart home features include

Rose Hall Blue Ocean Realty, LLC

70 Possum Rd, Weston, MA 02493
/33
$2,495,000

Open Sat 12PM - 2PM
- 4 Beds
- 2.5 Baths
- 4,157 Sq Ft
23 Stony Brook Rd, Weston, MA 02493

Pristine 4-bedroom Sweidler Colonial offers an open floor plan, enhanced by beautiful built-ins and millwork throughout. Custom cherry kitchen with large center island, opens to a vaulted, fireplaced family room - truly the heart of this home! The main level also features a dining room, fireplaced living room, two versatile home offices, half bath, and laundry. The second floor includes a primary

Jeanne Fleming Gibson Sotheby's International Realty

23 Stony Brook Rd, Weston, MA 02493
/42
$3,650,000

Open Sat 1PM - 2PM $345K PRICE DROP
- 5 Beds
- 3.5 Baths
- 5,285 Sq Ft
11 Hillcrest Rd, Weston, MA 02493

Stunning 5-bedroom, 3.5-bath contemporary multi-level home, thoughtfully gut renovated and expanded in 2008, offering impressive space, craftsmanship, and design. The gourmet eat-in kitchen opens seamlessly to a generous family room with fireplace and custom built-ins, creating an ideal setting for everyday living. An elegant formal living room and dining room with fireplace and built-ins add

Denise Mosher Coldwell Banker Realty - Weston

11 Hillcrest Rd, Weston, MA 02493
/12
$1,375,000

Open Sat 11AM - 12PM
- 3 Beds
- 3 Baths
- 2,357 Sq Ft
7 Longmeadow Rd, Weston, MA 02493

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

Deena Powell Gibson Sotheby's International Realty

7 Longmeadow Rd, Weston, MA 02493
/42
$2,695,000

Open Sat 11AM - 12:30PM $255K PRICE DROP
- 4 Beds
- 3.5 Baths
- 5,095 Sq Ft
55 Forest Ridge Rd, Weston, MA 02493

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

Denise Mosher Coldwell Banker Realty - Weston

55 Forest Ridge Rd, Weston, MA 02493
/31
$3,295,000

Open Sat 11:30AM - 12:30PM $155K PRICE DROP
- 4 Beds
- 4.5 Baths
- 7,195 Sq Ft
24 Trailside Rd, Weston, MA 02493

Experience where nature and tranquility converge. This unique home has direct access to town trails leading to the Weston Reservoir. Its striking stone and wood exterior enhanced by a gorgeous new cedar roof sets the tone for its warm and sophisticated interior. The living room stuns with soaring ceilings, exposed wood beams, and glass doors that open to a stone patio and exquisitely landscaped

Mizner+ Montero Gibson Sotheby's International Realty

24 Trailside Rd, Weston, MA 02493
/42
$29,000,000

$5M PRICE DROP
- 6 Beds
- 8 Baths
- 12,714 Sq Ft
4 Willow Rd, Weston, MA 02493

Step into a world of timeless elegance in this iconic English Revival Tudor. Prominently set high on a ridge abutting a tranquil pond and the lands surrounding the Weston Golf Club. The gated entry and winding approach reveal the commanding terraced property comprising over 6 secluded acres. The 1928 estate was originally designed by architect Eric Kibbon. A balance between modern comfort, beauty

Mizner+ Montero Gibson Sotheby's International Realty

4 Willow Rd, Weston, MA 02493
/41
$2,289,000

Open Sat 12PM - 1:30PM $100K PRICE DROP
- 4 Beds
- 4.5 Baths
- 3,784 Sq Ft
19 Old Rd, Weston, MA 02493

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,

Wei Wenny Fu Phoenix Real Estate

19 Old Rd, Weston, MA 02493
/39
$3,350,000

$145K PRICE DROP
- 5 Beds
- 7 Baths
- 5,023 Sq Ft
172 Country Dr, Weston, MA 02493

Incredible renovations to this stately brick colonial on a professionally landscaped 1.58 acres. Private views and wooded paths in the back yet nestled in one of Weston's favorite Southside neighborhoods. This 5/6 bedroom home has been transformed. Extensive improvements with new appliances in the kitchen that opens into a breakfast area with wetbar. Walk- in food pantry. Family room with

Melissa Dailey Coldwell Banker Realty - Wellesley

172 Country Dr, Weston, MA 02493
/40
$3,250,000

Open Sat 12PM - 1:30PM
- 4 Beds
- 5.5 Baths
- 6,419 Sq Ft
1 Graystone Ln, Weston, MA 02493

This sophisticated, contemporary Colonial, custom built in 1995, offers over 6,400 sq ft of beautifully updated living space with high-end finishes throughout. Ideally sited on a private Southside cul-de-sac, it’s surrounded by meticulously maintained, English garden–style grounds, creating a serene setting.Featuring 4 bedrooms, 5 full baths, and 1 half bath, the home blends timeless elegance

Dean Poritzky Engel & Völkers Wellesley

1 Graystone Ln, Weston, MA 02493
/42
$14,850,000
- 7 Beds
- 12 Baths
- 18,725 Sq Ft
67 Byron Rd, Weston, MA 02493

Timeless elegance meets modern luxury in this extraordinary Weston estate, situated on 5.3 stunning acres just minutes from Boston. Built by a renowned local builder and reimagined with Leslie Fine Interiors, this home blends superior craftsmanship, global influences and design. Bright, inviting spaces include a newly renovated kitchen, luxurious primary suite, soaring ceilings, and dramatic

Maggie Gold Seelig MGS Group Real Estate LTD

67 Byron Rd, Weston, MA 02493
/39
$31,500,000

$7M PRICE DROP
- 6 Beds
- 12 Baths
- 21,000 Sq Ft
180 Ash St, Weston, MA 02493

This extraordinary estate is set on one of Weston’s most prestigious enclaves and blends grand architecture with modern luxury, impeccable craftsmanship and state of the art systems. High ceilings, intricate moldings, and sun-drenched rooms create an atmosphere of timeless elegance. The main level is designed for both grand entertaining and comfortable living, featuring an expansive chef's

Maggie Gold Seelig MGS Group Real Estate LTD

180 Ash St, Weston, MA 02493
/39
$1,885,000

Open Sat 12PM - 2PM
- 5 Beds
- 3 Baths
- 3,485 Sq Ft
14 October Ln, Weston, MA 02493

Situated at 14 October Ln in Weston, MA, this single-family residence, constructed in 1960, offers 3485 square feet of meticulously maintained living space. This attractive property, in great condition, presents an exceptional opportunity for refined living within a distinguished community. The kitchen serves as a central gathering space, distinguished by its high ceiling, elegant stone counters,

Steven In RE/MAX Culture

14 October Ln, Weston, MA 02493
/39
$7,590,000

Open Sat 11AM - 12:30PM $205K PRICE DROP
- 6 Beds
- 7.5 Baths
- 8,421 Sq Ft
286 Country Dr, Weston, MA 02493

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

George Sarkis Douglas Elliman Real Estate - The Sarkis Team

286 Country Dr, Weston, MA 02493
/42
$1,750,000

$140K PRICE DROP
- 3 Beds
- 6 Baths
- 3,345 Sq Ft
40 Hobbs Brook Rd, Weston, MA 02493

Introducing a sophisticated contemporary retreat offering exceptional privacy, tranquil surroundings, and a seamless connection to nature. The open, versatile layout blends indoor and outdoor living for an elevated entertaining experience.The well-appointed kitchen flows into a spacious dining area and multiple inviting sitting spaces. Three beautifully designed bedrooms, including a bright and

Mizner+ Montero Gibson Sotheby's International Realty

40 Hobbs Brook Rd, Weston, MA 02493
/35
$2,325,000

Open Sat 2PM - 3:30PM
- 4 Beds
- 5 Baths
- 5,212 Sq Ft
20 Old Rd, Weston, MA 02493

Built in 1985 and set on a private 60,000 sq ft lot near Weston Town Center, this expansive contemporary Colonial offers more than 5,200 sq ft of light-filled living space in a highly desirable neighborhood. Designed for comfortable living and entertaining, the home features spacious sunfilled rooms throughout, including a dramatic front-to-back living room with fireplace and formal dining room.

Dean Poritzky Engel & Völkers Wellesley

20 Old Rd, Weston, MA 02493
/31
$7,295,000

Open Sat 11AM - 12:30PM
- 6 Beds
- 7.5 Baths
- 8,773 Sq Ft
5 Deer Path Ln, Weston, MA 02493

This newly-constructed, Contemporary offers the pinnacle of luxury living on Weston’s coveted Southside. The dramatic, 2-story foyer flows seamlessly into both formal & informal spaces. The dining/living room is optimal for family gatherings & entertaining, and the custom kitchen w/an exceptional quartz island, high-end appliances & wet bar adjoins a generous eat-in area & fireplaced family room

Beyond Boston Properties Group Compass

5 Deer Path Ln, Weston, MA 02493
/15
$2,399,000

$201K PRICE DROP
- 4 Beds
- 4.5 Baths
- 3,395 Sq Ft
416 Conant Rd, Weston, MA 02493

Built in 2022 with a blend on modern and traditional. Excellent open floorplan with 4 bedrooms, each with ensuite bathroom. 9' ceilings with large windows on the first and second floors make this smaller house spacious. Large deck that overlooks a private backyard. The home is heated with a 95% efficient Viessmann gas boiler, and has foam insulation throughout. Finished walk out basement and

Derek Greene The Greene Realty Group

416 Conant Rd, Weston, MA 02493
/19
$7,550,000
- 6 Beds
- 9 Baths
- 8,863 Sq Ft
132 Country Dr, Weston, MA 02493

Designed for elevated everyday living and effortless entertaining, this exceptional residence at 132 Country Drive in Weston offers the perfect blend of luxury, comfort, and convenience. Set in one of Weston’s most desirable neighborhoods—known for its top-ranked schools and peaceful surroundings—the home is just minutes from Boston and major commuter routes. Inside, an oversized chef’s kitchen

Sheryl Simon Gibson Sotheby's International Realty

132 Country Dr, Weston, MA 02493
/40
$5,245,000

Open Sat 12:30PM - 2PM $550K PRICE DROP
- 5 Beds
- 8 Baths
- 9,200 Sq Ft
300 Glen Rd, Weston, MA 02493

Stunning shingle style 5 bedroom home on Weston's South side. Completely renovated kitchen & baths giving this home the ideal layout, style & convenient location. Light filled kitchen w/ large picture window overlooks the 2.68 acres plus abutting conservation land w/ trails. Huge center island & high end appliances w/ working fireplace in kitchen. Adjacent family room w/ coffered ceilings,

Melissa Dailey Coldwell Banker Realty - Wellesley

300 Glen Rd, Weston, MA 02493
/22
$3,075,000

Open Sun 11:30AM - 1PM $120K PRICE DROP
- 4 Beds
- 4.5 Baths
- 5,438 Sq Ft
183 Conant Rd, Weston, MA 02493

Stunning custom new construction in a prime Weston location offering 5,500+ 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

Gabby Cefalo Coldwell Banker Realty - Wellesley

183 Conant Rd, Weston, MA 02493
/42
$5,999,000
- 4 Beds
- 7 Baths
- 7,600 Sq Ft
44 Meadowbrook Rd, Weston, MA 02493

This California Contemporary defines sophisticated living at its finest. Majestically nestled on 2 private, stunning acres in the coveted Weston Country Club neighborhood.The terraced grounds are accented with stone patios, a salt water pool and cabana. Soaring ceilings and an abundance of sunlight flood the multiple levels of thoughtfully designed living spaces. A dramatic family room has

Mizner+ Montero Gibson Sotheby's International Realty

44 Meadowbrook Rd, Weston, MA 02493
/27
$1,675,000
- 4 Beds
- 3 Baths
- 2,840 Sq Ft
37 School St, Weston, MA 02493

Beautifully sited on over 2 private acres, this 8-room, 4-bed, 3-bath home offers comfort, charm, and room to grow. The spacious living room features a fireplace and hardwood floors, flowing into a formal dining room with two classic corner cabinets and a sun-filled kitchen with white cabinetry, stainless appliances, and center island. Two generous bedrooms and a full bath complete the first

Denise Mosher Coldwell Banker Realty - Weston

37 School St, Weston, MA 02493
/25
$2,499,000

$396K PRICE DROP
- 5 Beds
- 4.5 Baths
- 4,590 Sq Ft
27 Silver Hill Rd, Weston, MA 02493

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,

Deena Powell Gibson Sotheby's International Realty

27 Silver Hill Rd, Weston, MA 02493

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