Homes for Sale near Weston High School

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  /34

  $4,950,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 7,547 Sq Ft

  51 Willard Rd, Weston, MA 02493

  Looking to move in the summer of 2026 and add your own touches to your dream home? Set on a private road and nestled at the end of a quiet cul de sac, 51 Willard sits on 1.25 acres surrounded by natural beauty and luxury new construction. This rare offering invites you to craft a legacy estate defined by privacy, sophistication, and timeless design. Inside, over 7,500 square feet of living space

  

  Yassien Youssef

  Compass

  (339) 218-4223

  51 Willard Rd, Weston, MA 02493
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  Explore Weston High School

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  /28

  $5,150,000

  • 5 Beds
  • 4.5 Baths
  • 4,340 Sq Ft

  135 Orchard Ave, Weston, MA 02493

  Welcome to 135 Orchard Avenue, a rare and exceptional property in Weston. Set on over 2.5 acres of peaceful land with expansive views of untouched meadows, this historic home—originally part of the 1900 Hubbard Estate—has been masterfully restored by the renowned firm Dewing Schmid Kearns. The result is a harmonious blend of timeless character and modern elegance, just minutes from Boston. The

  Dean Poritzky Engel & Völkers Wellesley

  135 Orchard Ave, Weston, MA 02493
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  /38

  $4,995,000

  • 6 Beds
  • 7 Baths
  • 7,000 Sq Ft

  21 Westerly Rd, Weston, MA 02493

  Stunning shingle and stone 6 bedroom Colonial in coveted Weston Estates! 1.38 acres of flat land with 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
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  /42

  $4,680,000

  • 5 Beds
  • 6.5 Baths
  • 8,500 Sq Ft

  11 Winthrop Cir, Weston, MA 02493

  This stunning contemporary home, designed by Marcus Gleysteen Architects and completed in 2017, blends modern sophistication with mid-century inspiration. Situated on a peaceful cul-de-sac, the residence spans over 1.5 acres and is thoughtfully positioned along a crescent drive, offering two distinct architectural perspectives. Expansive windows seamlessly integrate natural surroundings with

  Dream Team Dreamega International Realty LLC

  11 Winthrop Cir, Weston, MA 02493
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  /42

  $8,295,000 Open Thu 11:30AM - 1PM

  • 6 Beds
  • 7.5 Baths
  • 8,421 Sq Ft

  286 Country Dr, Weston, MA 02493

  This exceptional estate, set in one of Weston’s most coveted neighborhoods, blends modern architecture, bespoke luxury & state-of-the-art technology. Perched atop a 1.42-acre corner lot, it spans approx. 8,421sf across 3 levels w/ 6 ensuite beds & 7.5 baths. A sprawling entry opens to a soaring foyer, sculptural staircase & statement pendant, while sunlit living spaces feature floor-to-ceiling

  Ricardo Rodriguez Coldwell Banker Realty - Boston

  286 Country Dr, Weston, MA 02493
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  /27

  $4,695,000

  • 5 Beds
  • 8 Baths
  • 7,369 Sq Ft

  168 Beaver Rd, Weston, MA 02493

  Once in a while, a home comes along that draws you in and takes your breath away. Situated on a 1.98 acre lot on a serene cul-de-sac in Southside Weston, this young shingled residence will win your heart. Enter into the foyer with 28 foot ceilings & immediately notice the thoughtful layout, incredible attention to detail and finely crafted finishes at every turn. The superbly designed kitchen

  The Shulkin Wilk Group Compass

  168 Beaver Rd, Weston, MA 02493
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  /36

  $7,850,000

  • 6 Beds
  • 9 Baths
  • 11,929 Sq Ft

  448 & 454 Concord Rd, Weston, MA 02493

  Rare Weston Estate – Set on over 2 acres of manicured grounds abutting miles of conservation land and trails, this extraordinary 12000 sq ft residence offers unmatched privacy with easy access to Boston and Cambridge. Built by premier builder Sanford Custom Homes and meticulously maintained, the estate features 6 ensuite bedrooms and exceptional craftsmanship throughout. Grand entertaining spaces

  Dean Poritzky Engel & Völkers Wellesley

  448 & 454 Concord Rd, Weston, MA 02493
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  /37

  $4,725,000

  • 6 Beds
  • 6.5 Baths
  • 9,038 Sq Ft

  100 Westcliff Rd, Weston, MA 02493

  Experience the best of both Wellesley and Weston at 100 Westcliff. Ideally located right on Wellesley/Weston line, this exquisite 9,000 sq. ft. multi-level custom home in Southside Weston offers tranquil pond views, a modern flexible floor plan, and a private setting amidst lush landscaping. Enjoy stunning, sun-drenched rooms with vaulted ceilings, Palladian windows, five fireplaces, and artisan

  Donahue Maley & Burns Team Compass

  100 Westcliff Rd, Weston, MA 02493
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  /30

  $4,390,000

  • 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
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  /42

  $7,598,000

  • 6 Beds
  • 10 Baths
  • 9,000 Sq Ft

  56 Cart Path Rd, Weston, MA 02493

  Exquisite colonial estate in Weston’s golf club area. Perfect location on 2.85 acres in Weston's best 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
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  /42

  $4,090,000

  • 6 Beds
  • 6.5 Baths
  • 9,064 Sq Ft

  42 Westerly Rd, Weston, MA 02493

  Exceptional 6-bed, 6.5-bath French-inspired estate with signature Mansard roof, set on 1.42 acres in Weston Estates. With 9000+ sq ft above grade plus a finished walk-out lower level, this home features a grand foyer with double doors, sweeping staircase, and custom aquarium. Coffered ceilings, triple windows, and hardwood floors accentuate the opulent living spaces. The chef’s kitchen offers

  Chorr-Kin Chin Vetra Estates, LLC

  42 Westerly Rd, Weston, MA 02493
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  /42

  $8,999,999

  • 5 Beds
  • 9 Baths
  • 7,382 Sq Ft

  8 Conant Rd, Weston, MA 02493

  8 Conant Road is a grand estate that offers the perfect balance of ultimate privacy and the convenience of living in the heart of Weston’s center. This completely remodeled Tudor Revival sits on 3.05 acres, surrounded by magnificent gardens and mature landscaping, and perfectly placed at the end of a quiet street. The detached carriage house, also fully remodeled, features an apartment, 2

  George Sarkis Douglas Elliman Real Estate - The Sarkis Team

  8 Conant Rd, Weston, MA 02493
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  /33

  $3,785,000

  • 3 Beds
  • 4.5 Baths
  • 4,985 Sq Ft

  1 Pine Summit Cir, Weston, MA 02493

  Curated style and luxury to be found at 1 Pine Summit Circle This spacious stand alone condo features spacious rooms, open floor plan, first floor private primary suite with luxurious spa bath and study. Great room open to cook's kitchen, breakfast area and family room with marble surround gas fireplace, private three season porch and deck. Gorgeous sitting room and entertainment size dining

  Leeann Yolin Coldwell Banker Realty - Weston

  1 Pine Summit Cir, Weston, MA 02493
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  /21

  $1,375,000

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  48 Golden Ball Rd, Weston, MA 02493

  Charming Colonial Farmhouse- Nestled on a quiet cul-de-sac just moments from Weston’s town center. Introducing 48 Golden Ball, an inviting home with timeless charm and modern updates. thoughtfully renovated blending both character and comfort, this home features 3 bedrooms and 2.5 baths. The stunning kitchen is the heart of this special home and features a stone topped island, stainless steel

  Sheryl Simon Gibson Sotheby's International Realty

  48 Golden Ball Rd, Weston, MA 02493
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  /25

  $859,000

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft

  52 Jericho Rd Unit 52, Weston, MA 02493

  Nestled in the serene and prestigious town of Weston, this beautiful townhouse gives you single-family feel and perfectly blends modern comfort with timeless charm. The open-concept kitchen, equipped with high-end appliances and a spacious island, is ideal for both everyday living and entertaining. Spacious bedrooms and en-suite primary suite for ultimate comfort. Thoughtfully designed

  Shasha Chang Peace of Mind Realty

  52 Jericho Rd Unit 52, Weston, MA 02493
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  /27

  $1,459,000

  • 3 Beds
  • 2.5 Baths
  • 3,240 Sq Ft

  5 Upham Way Unit 5, Weston, MA 02493

  This expansive meticulously updated Winter Garden Townhouse features high-end finishes and thoughtful details throughout. A spectacular kitchen features handcrafted Kennebec cabinetry, soapstone countertops, Miele appliances, a center island, and dining area that opens to a private garden patio. The main level offers an inviting flow beginning with a refined living room that transitions

  Mizner+ Montero Gibson Sotheby's International Realty

  5 Upham Way Unit 5, Weston, MA 02493
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  /15

  $2,600,000

  • 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
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  /42

  $10,950,000

  • 6 Beds
  • 8 Baths
  • 10,845 Sq Ft

  8 Hidden Rd, Weston, MA 02493

  Significant turnkey custom residence in prime Weston Golf Club neighborhood with expansive yard. 6-bedroom shingle-and-stone manor with copper accents and refined finishes, privately set above Hidden Road. Tucked behind mature landscaping, a winding drive leads to a flat motor court with generous parking. Foyer opens to living room with fireplace and backyard access. Dining room served by

  Chaplin Partners Compass

  8 Hidden Rd, Weston, MA 02493
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  /34

  $12,500,000

  • 6 Beds
  • 11 Baths
  • 14,620 Sq Ft

  3 Idlewile Ln, Weston, MA 02493

  A world-class estate unlike any other—this gated 8+ acre sanctuary in Weston’s most prestigious south side enclave redefines luxury living. Encompassing over 14,000 sq. ft. of show-stopping design and craftsmanship, this architectural marvel is a symphony of soaring domes, hand-carved millwork, imported stone, and Venetian plaster. Every inch radiates grandeur, from the richly appointed living

  Jamie Genser Coldwell Banker Realty - Brookline

  3 Idlewile Ln, Weston, MA 02493
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  /28

  $1,539,000

  • 4 Beds
  • 4 Baths
  • 2,250 Sq Ft

  1 Aberdeen Rd, Weston, MA 02493

  This inviting Cotswold style home is sited beautifully on app. .6 acres of land with mature plantings and lots of open grass and seating areas and a detached 2 car garage. The first floor offers: beamed ceilings, a fireplace with delft tile surround, a living area with seating and dining opens to a chef's kitchen with Brazilian granite, maple cabinets and stainless appliances. Additionally on

  Paige Yates Coldwell Banker Realty - Weston

  1 Aberdeen Rd, Weston, MA 02493
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  /26

  $2,900,000

  • 6 Beds
  • 5.5 Baths
  • 6,226 Sq Ft

  30 Page Rd, Weston, MA 02493

  Stately brick Colonial located in a desirable cul-de-sac neighborhood on a beautifully landscaped lot with sprawling backyard. This spacious & sun-filled home offers the perfect blend of traditional charm & modern comfort. Designed for entertaining & everyday living, the 1st floor features a bedroom & full bath ideal for guests or multigenerational living. Enjoy entertaining in the formal DR, LR

  Sheryl Simon Gibson Sotheby's International Realty

  30 Page Rd, Weston, MA 02493
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  /22

  $2,495,000

  • 4 Beds
  • 4 Baths
  • 3,566 Sq Ft

  16 Pinecroft Rd, Weston, MA 02493

  Expertly renovated in 2017 and meticulously maintained, this 4-bedroom farmhouse Cape features high-end finishes throughout and striking views of the picturesque landscape. This beautiful home is surrounded by rolling lawns, perennial gardens, stone retaining walls, and a serene patio with a lovely fountain. Upon entering, one is welcomed into an elegant and spacious front-to-back foyer. There

  Dean Poritzky Engel & Völkers Wellesley

  16 Pinecroft Rd, Weston, MA 02493
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  /28

  $1,795,000 Open Sun 2:30PM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft

  75 Westland Rd, Weston, MA 02493

  Welcome home to this beautifully expanded and updated 4-bedroom, 3-full-bath Cape, ideally situated on just over an acre of wooded privacy in a popular neighborhood. The eat-in kitchen, complete with newer stainless appliances, opens effortlessly to a sun-drenched sunroom and inviting family room with built-ins and a wood-burning fireplace—perfect for everyday living and entertaining. A spacious

  Denise Mosher Coldwell Banker Realty - Weston

  75 Westland Rd, Weston, MA 02493
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  /20

  $2,350,000

  • 5 Beds
  • 5.5 Baths
  • 3,713 Sq Ft

  103 Loring Rd, Weston, MA 02493

  This historic Colonial in Weston’s coveted south side location combines timeless charm with thoughtful modern updates. Beautiful stone walls enhance its classic New England character. Inside, the inviting eat-in kitchen opens to a cathedral-ceiling family room with a fireplace, while a formal living room, private office, and optional first-floor bedroom provide flexibility for today’s lifestyle.

  Mizner+ Montero Gibson Sotheby's International Realty

  103 Loring Rd, Weston, MA 02493
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  /37

  $2,695,000

  • 4 Beds
  • 3.5 Baths
  • 4,130 Sq Ft

  54 Woodchester Dr, Weston, MA 02493

  Stunning Colonial set on over an acre of beautifully landscaped grounds in one of Weston’s most desirable South Side neighborhoods is beautifully designed with an open and inviting layout. The expansive kitchen seamlessly flows into the sun filled family room, a fabulous space, defined by its impressive vaulted ceiling and skylight, allowing natural light to cascade into the room creating the

  The Lara & Chelsea Collaborative Coldwell Banker Realty - Wellesley

  54 Woodchester Dr, Weston, MA 02493
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  /36

  $789,990 Open Sat 11AM - 12:30PM

  • 2 Beds
  • 1.5 Baths
  • 1,360 Sq Ft

  24 Jericho Rd Unit 24, Weston, MA 02493

  Welcome to this sunny, meticulously maintained townhouse nestled in Weston—just 15 miles west of Boston, ideal for commuters and city escape-seekers alike. Set in a tranquil, well-managed community, the home boasts a functional layout with bright living spaces, recessed lighting, hardwood floors, a modern kitchen, cozy bedrooms, and in-unit laundry. Outside, a private patio opens to lush grounds

  The WP Group Smith and Oak Real Estate Co.

  24 Jericho Rd Unit 24, Weston, MA 02493
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  /41

  $1,499,900

  • 4 Beds
  • 5 Baths
  • 3,651 Sq Ft

  426 Conant Rd, Weston, MA 02493

  Nestled on a generous lot in Weston, the single-family residence at 426 Conant Rd. presents an attractive opportunity for discerning homeowners, offering a blend of classic charm and comfortable living. The property is bright and inviting. The living room is a focal point, showcasing a gas fireplace and hardwood floors. A vaulted ceiling in the adjacent great room amplifies the sense of space,

  Dana Ingram Ingram Realty Co.

  426 Conant Rd, Weston, MA 02493
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  /25

  $2,299,000

  • 4 Beds
  • 5 Baths
  • 4,041 Sq Ft

  620 South Ave, Weston, MA 02493

  Recently completed and beautifully renovated,this 4,000+ sq ft Contemporary sits on 2.61 acres, offering a striking first impression with landscaped circular drive.A dramatic foyer showcases soaring ceilings,crisp white finishes, and walls of glass flooding the home with natural light.The first floor is designed for both everyday living and entertaining, featuring a formal dining room, living

  Cynthia Tamburro Advisors Living - Weston

  620 South Ave, Weston, MA 02493
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  /39

  $10,900,000

  • 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 its own 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

  Rose Hall Blue Ocean Realty, LLC

  70 Possum Rd, Weston, MA 02493
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  /39

  $2,890,000

  • 4 Beds
  • 7 Baths
  • 5,181 Sq Ft

  130 Summer St, Weston, MA 02493

  One of a kind! Stunning customized luxury home, nested in private lot. The chef’s kitchen features an oversized center island with seating, Wolf and Sub-Zero appliances, and a custom stone pizza oven. Bar cabinet has built-in sub-zero refrigerator and ice maker. Charming kitchen with French slide door presents you tree view for all seasons. It seamlessly flows into the dining area and a grand

  Soyeon Yang Spark Real Estate

  130 Summer St, Weston, MA 02493
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  /10

  $7,500,000

  • Land
  • 6.88 Acres
  • $1,090,116 per Acre

  0 Wellesley St, Weston, MA 02493

  Unique opportunity to own a pristine 6.88 acre retreat lot, surrounded partially by conservation land. The property features two parcels of land being sold together. Come walk this stunning property, located south of Rte 20, near historic Chestnut Street. Build your dream estate, 15 miles from Boston, minutes to the highway. Existing 4 bedroom house is likely a tear down. View attached land

  Margaret Rogers Compass

  0 Wellesley St, Weston, MA 02493
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  /11

  $1,099,000

  • 3 Beds
  • 1.5 Baths
  • 1,390 Sq Ft

  6 Overlook Dr, Weston, MA 02493

  Great opportunity to get into Weston, this 6 room 3 bed 1.5 bath ranch with finished lower level and two car garage sits on over a 40k sqft lot. Great for an end user trying to get into the top Weston school district and great commuter location Or builders bring your vision to life on this large corner lot. Close to parks major routes and more. Come see the potential for yourself!

  Jaime Venezia Real Estate Pros Inc.

  6 Overlook Dr, Weston, MA 02493
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  /42

  $34,000,000

  • 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,

  Mizner+ Montero Gibson Sotheby's International Realty

  4 Willow Rd, Weston, MA 02493
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  /38

  $29,000,000

  • 6 Beds
  • 8 Baths
  • 17,067 Sq Ft

  9 Atlas Ln, Weston, MA 02493

  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

  Mizner+ Montero Gibson Sotheby's International Realty

  9 Atlas Ln, Weston, MA 02493
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  /26

  $2,650,000

  • 4 Beds
  • 4.5 Baths
  • 4,379 Sq Ft

  156 Cherry Brook Rd, Weston, MA 02493

  Extensively renovated & expanded Cape set on 3+ acres in highly desirable Weston neighborhood. 4,300+ sf of living space - inc. 4 Beds, 2 Offices, & 4.5 Baths - this home offers luxury & livability. Oversized windows, skylights, & French doors fill the home w/ natural light while 3 fireplaces add warmth & charm. Chef’s Kitchen w/ vaulted ceiling, oversized island, wine chiller, & brick-accented

  Elizabeth Crampton Coldwell Banker Realty - Lexington

  156 Cherry Brook Rd, Weston, MA 02493
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  /28

  $1,980,000

  • 3 Beds
  • 3 Baths
  • 3,252 Sq Ft

  120 Church St, Weston, MA 02493

  Super unique opportunity to live in this great house, designed by famed architect, Ernest Flagg, with a fabulous heated indoor pool for year around water fun. Three beds, three bath stone Villa with two car garage parking, professional landscaped yard, tucked away behind trees from view. Oversized quartz waterfall island and beautiful white cabinetry, with tons of storage tucked away discretely.

  Yuan Huang NextGen Realty, Inc.

  120 Church St, Weston, MA 02493
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  /26

  $2,780,000

  • 5 Beds
  • 4.5 Baths
  • 4,885 Sq Ft

  183 Kings Grant Rd, Weston, MA 02493

  Move-in elegant colonial house sits on a cul-de-sac in the sought-after Kings Grant neighborhood. Professional landscaped 2+ acre land provides space for a potential pool or/and tennis court. Lots of recent upgrades with roof, kitchen, bathrooms, hardwood floor, lighting, exterior and interior painting. On the 1st floor: white kitchen with beautiful island, open dining room, farmhouse style

  Mai Luo Kendall Realty, LLC

  183 Kings Grant Rd, Weston, MA 02493
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  /30

  $2,800,000

  • 5 Beds
  • 3 Baths
  • 5,328 Sq Ft

  169 Hickory Rd, Weston, MA 02493

  Rarely available, this stunning contemporary home has been expertly renovated and is nestled on over 1.4 acres in one of Weston’s most beloved South Side neighborhoods. Bathed in natural light, the home offers privacy and serves as a true oasis, surrounded by lush gardens, a spectacular pool, fieldstone walls, and serene patios. Designed with the finest finishes and impeccable attention to

  Dean Poritzky Engel & Völkers Wellesley

  169 Hickory Rd, Weston, MA 02493
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  /39

  $38,000,000

  • 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
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  /29

  $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

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