Homes for Sale near Weston High School

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  /42

  $4,290,000

  • 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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• 

  

  

  /39

  $3,900,000

  • 5 Beds
  • 5.5 Baths
  • 6,700 Sq Ft

  21 Bemis St, Weston, MA 02493

  Stunning 5BR, 6BA home offering over 6,700sqft. of luxurious living space across two levels, plus a 3000sqft.+ unfinished lower level, ready for your vision. A harmonious blend of modern and rustic design elements featuring exposed beams,12ft ceilings throughout, dramatic 8ft high French doors that flank the front & back of the home & incredible cypress wood home office with floor to ceiling

  Tori MacDowell Advisors Living - Weston

  21 Bemis St, Weston, MA 02493
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  /41

  $6,495,000

  • 5 Beds
  • 7 Baths
  • 8,210 Sq Ft

  72 Love Ln, Weston, MA 02493

  Quality construction and fine finishes define this sophisticated residence tranquilly sited on one of Weston’s most coveted streets. This exceptional home offers over 8200 sqft of luxurious living space w/soaring ceilings throughout. Expansive foyer opens into airy floor plan including formal living w/fireplace, spacious dining room, private office, gourmet kitchen w/custom cabinetry & large

  Deena Powell Advisors Living - Weston

  72 Love Ln, Weston, MA 02493
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  /42

  $3,895,000 Open Sun 12PM - 2PM

  • 5 Beds
  • 7 Baths
  • 6,797 Sq Ft

  4 Prescott Ln, Weston, MA 02493

  Meticulously maintained & updated home combines grand living, timeless design & quality construction. Commuter's dream w/ easy highway access tucked into a 1.94 acre suburban oasis. The layout allows for spacious living, entertaining, & room for generations of family. Main floor features open concept family room & state-of-the-art kitchen w/ Viking appliances, ample cabinetry, & coveted butlers

  Nicoline Lomas William Raveis R.E. & Home Services

  4 Prescott Ln, Weston, MA 02493
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  /42

  $4,695,000

  • 5 Beds
  • 9 Baths
  • 8,625 Sq Ft

  15 Rockport Rd, Weston, MA 02493

  Exquisite Southside estate with nearly 2 level acres blending timeless elegance with modern luxury. Custom millwork, soaring ceilings, and abundant light define this thoughtfully designed home. A grand foyer opens to a formal living room with gas fireplace, private office, and refined dining room. The chefs eat-in kitchen, with premium appliances, large island and butler's pantry, flows into an

  Denise Mosher Coldwell Banker Realty - Weston

  15 Rockport Rd, Weston, MA 02493
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  /15

  $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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  /29

  $7,498,000

  • 5 Beds
  • 9 Baths
  • 8,086 Sq Ft

  180 Highland St, Weston, MA 02493

  This custom-built estate exudes timeless elegance and unparalleled craftsmanship. Set on three sprawling acres of level land, the private setting makes it the ideal retreat for those seeking luxury and comfort. The home’s classic Shingle style blends seamlessly with the lush surrounding landscape. Once inside, the rich, intricate wood trim throughout the home sets the tone for the design

  Teri Adler MGS Group Real Estate LTD - Wellesley

  180 Highland St, Weston, MA 02493
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  /42

  $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

  $4,850,000

  • 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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  /38

  $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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  /36

  $4,395,000

  • 4 Beds
  • 6 Baths
  • 7,045 Sq Ft

  15 Evergreen Ave, Weston, MA 02493

  Situated in a highly desirable South Side neighborhood, this unique custom home provides an unparalleled living experience with top-notch amenities and finishes, seamlessly blending indoor and outdoor living. As you enter, the exceptional main floor layout impresses with a spectacular living room, a chef's kitchen with large island and pantry, an informal dining area with banquette, and a cozy

  The Shulkin Wilk Group Compass

  15 Evergreen Ave, Weston, MA 02493
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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

  51 Willard Rd, Weston, MA 02493
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  /15

  $484,900 Open Sun 1PM - 2:30PM

  • 1 Bed
  • 1 Bath
  • 728 Sq Ft

  53 Jericho Rd Unit A, Weston, MA 02493

  Beautiful and bright one bedroom condo in quiet Stonegate neighborhood in Weston. Open living room/dining room, fireplace, sliding glass door to patio. Hardwood floors. Four closets plus extra storage unit. Washer/dryer. Newer appliances. One assigned off-street parking space (#144) plus extra guest spaces. Near Weston Center, Routes 20 and 128, Commuter rail station, Walk/Bike Trail, Regis

  Daphne Romanoff New England Home Realty

  53 Jericho Rd Unit A, Weston, MA 02493
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  /42

  $3,500,000

  • 4 Beds
  • 6 Baths
  • 5,656 Sq Ft

  130 Hickory Rd, Weston, MA 02493

  Set on a knoll, this classic colonial is updated in all the best ways. Stylish design, bright, cheery spaces blended with gorgeous views of meticulously landscaped yard. This 4bd home offers fresh, spacious kitchen/family room with fireplace, eat-in-area and butler’s pantry. Formal dining and living rooms. Home Office. Splendid sunroom. Newly finished lower level. Guest house with all amenities

  Chaplin Partners Compass

  130 Hickory Rd, Weston, MA 02493
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  /39

  $3,388,000 Open Sun 12PM - 1PM

  • 6 Beds
  • 4 Baths
  • 4,350 Sq Ft

  86 Myles Standish Rd, Weston, MA 02493

  Modern Weston retreat on 2.3+ private acres at the end of a cul-de-sac. The main home is a sun-filled contemporary with 5 spacious bedrooms, 3 full baths, and an open layout featuring soaring ceilings, walls of glass, and tranquil garden views. The renovated, sleek kitchen with abundant cabinet and counter space, a Sub-Zero fridge, Miele oven, and induction cooktop, flowing into a spacious dining

  Denise Mosher Coldwell Banker Realty - Weston

  86 Myles Standish Rd, Weston, MA 02493
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  /42

  $10,950,000

  • 5 Beds
  • 7 Baths
  • 9,295 Sq Ft

  8 Hidden Rd, Weston, MA 02493

  Significant turnkey custom residence on prime Weston Golf Club street with expansive yard. Shingle-and-stone manor with copper accents and refined finishes privately set above Hidden Road. Tucked behind extensive mature landscaping, winding drive leads to flat motor court with generous parking. Foyer opens to living room with fireplace and welcoming backyard views. Dining room connects to chef’s

  Chaplin Partners Compass

  8 Hidden Rd, Weston, MA 02493
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  /26

  $2,859,000

  • 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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  /42

  $2,695,000

  • 4 Beds
  • 3.5 Baths
  • 3,811 Sq Ft

  338 Highland St, Weston, MA 02493

  Picture perfect Colonial conveniently located on the south side with sidewalks to the public schools. Completely renovated 4 bedroom home with covered front porch. Formal dining and living room is perfect for entertaining. Modern kitchen with stainless steel appliances, and quartz countertops with eat-in-kitchen to family room. Sunroom opens to patio that looks out over sunny landscaped backyard.

  Chaplin Partners Compass

  338 Highland St, Weston, MA 02493
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  /28

  $3,250,000

  • 4 Beds
  • 2.5 Baths
  • 3,332 Sq Ft

  12 Meadowbrook Rd, Weston, MA 02493

  This timeless, light-filled home in the country club neighborhood of Weston is not to be missed. The property offers a main house, separate out-building, garage, and tennis court. The main home is a classic brick colonial and has been fully renovated from top to bottom offering a thoughtful and welcoming layout. The spacious living room boasts beautiful original details, and the bright family

  Jamie Ovadia MGS Group Real Estate LTD

  12 Meadowbrook Rd, Weston, MA 02493
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  /30

  $3,095,000 Open Sun 12PM - 1:30PM

  • 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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  /37

  $1,925,000 Open Sun 1PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 3,650 Sq Ft

  64 Bakers Hill Rd, Weston, MA 02493

  Set on a beautifully landscaped acre in one of Weston's most popular neighborhoods, this expansive multi-level contemporary offers the ideal combination of comfort, elegance, and versatile living. With 10 thoughtfully designed rooms, including 4 generous bedrooms and 2.5 baths, the home effortlessly accommodates both daily life and memorable entertaining. The living room features a dramatic wall

  Denise Mosher Coldwell Banker Realty - Weston

  64 Bakers Hill Rd, Weston, MA 02493
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  /30

  $2,495,000

  • 4 Beds
  • 3.5 Baths
  • 4,418 Sq Ft

  51 Summer St, Weston, MA 02493

  The Clarence “Fleetwood” Mosher House at 51 Summer Street in Weston, Massachusetts, was built in 1910 and has been thoughtfully expanded and remodeled. Offering over 4,400 square feet of sun-filled living space, this farmhouse-style home is perfect for comfortable living and entertaining. The stunning gourmet kitchen features custom cabinetry, a farm sink, two dishwashers, and a pantry, and flows

  Dean Poritzky Engel & Völkers Wellesley

  51 Summer St, 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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  /39

  $2,395,000 Open Sun 1:30PM - 3PM

  • 4 Beds
  • 4.5 Baths
  • 4,465 Sq Ft

  56 Arrowhead Rd, Weston, MA 02493

  Move in ready 10-room, 4-bedroom Colonial nestled in a highly desirable neighborhood. The gracious dining room and formal living room with wood-burning fireplace offer timeless elegance, perfect for entertaining or relaxed evenings. A chef’s eat-in kitchen features stainless appliances, a walk-in pantry, and an expansive island, flowing seamlessly into a sunlit family room with access to a large

  Denise Mosher Coldwell Banker Realty - Weston

  56 Arrowhead Rd, Weston, MA 02493
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  /42

  $1,699,000

  • 4 Beds
  • 2.5 Baths
  • 2,938 Sq Ft

  254 Conant Rd, Weston, MA 02493

  Iconic Jesse Sumner Viles House, circa 1847, blends classic Greek Revival architecture with modern updates. This sunlit 4-bed antique sits on .79 acres of level meadow, upland. A farmer’s porch opens to a welcoming main hall, oversized great room with fireplace, and formal dining room. The updated country kitchen with farmers sink, custom cabinets, quartz countertops and stainless steel

  Chaplin Partners Compass

  254 Conant Rd, Weston, MA 02493
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  /28

  $1,875,000

  • 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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  /36

  $3,090,000

  • 5 Beds
  • 3.5 Baths
  • 4,800 Sq Ft

  3 Conant Rd, Weston, MA 02493

  Beyond Stunning!!!!! Have the best of both worlds! Incredible 1 acre flat lot in the heart of Weston Center w/ the urban suburban lifestyle in this fully renovated home! Extensive recent renovations gives this home the classic feel but it is all NEW! High ceilings, filled w/ sunlight & gorgeous millwork throughout. Spacious foyer with gorgeous staircase is flanked by the large dining room &

  Melissa Dailey Coldwell Banker Realty - Wellesley

  3 Conant 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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  /35

  $2,895,000

  • 5 Beds
  • 3.5 Baths
  • 5,100 Sq Ft

  137 Wellesley St, Weston, MA 02493

  Set on a picturesque 1.38 acre lot with sweeping views of open fields and mature trees, this stunning Greek Revival home built in 1847 and part of the historic Case Estates has been beautifully transformed with a modern aesthetic. Located in the heart of Weston Center and surrounded by 42 acres formerly owned by Harvard’s Arnold Arboretum, it offers privacy with unbeatable convenience. A classic

  Dean Poritzky Engel & Völkers Wellesley

  137 Wellesley St, Weston, MA 02493
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  /23

  $1,625,000 Open Sun 1:30PM - 2:30PM

  • 4 Beds
  • 3.5 Baths
  • 2,700 Sq Ft

  23 Old Coach Rd, Weston, MA 02493

  Tucked away at the end of a quiet dead-end street in highly desirable Weston, MA, this charming 1963 Colonial offers rare privacy and direct access to scenic conservation trails. Just minutes from the Kendall Green commuter rail, it’s perfectly located for both peaceful living and easy city access. Inside, the home features 4 bedrooms, 3.5 baths, a spacious living room with a dramatic

  Taylor Yates Coldwell Banker Realty - Weston

  23 Old Coach Rd, Weston, MA 02493
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  /23

  $1,850,000 Open Sun 2:30PM - 3:30PM

  • 3 Beds
  • 2.5 Baths
  • 3,090 Sq Ft

  167 Conant Rd, Weston, MA 02493

  Welcome to this much-admired, quintessential New England home, set back from the road on a scenic knoll with stone walls and a circular drive. Inside, a gracious foyer opens to a fireplaced family room and a front-to-back living room with another fireplace. Rich in timeless detail, this 1940s gem features a formal dining room with built ins, eat in kitchen with gas range, home office with

  Denise Mosher Coldwell Banker Realty - Weston

  167 Conant Rd, Weston, MA 02493
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  /40

  $8,495,000

  • 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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  /15

  $1,795,000

  • Land
  • 1.01 Acres
  • $1,777,228 per Acre

  217 Summer St, Weston, MA 02493

  Great opportunity to finish your dream home. Scenic tree-filled lot complete with a picturesque creek for a serene, natural setting. This single family home has been gutted and is awaiting a homeowner ready-to-build, offering the perfect foundation to craft your custom house. Only a foundation and frame exists. Near top schools in the state. Exceptional access to both I-95 and I-90, making

  Eric Glassoff Coldwell Banker Realty - Brookline

  217 Summer St, Weston, MA 02493
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  /27

  $1,795,000

  217 Summer St, Weston, MA 02493

  Great opportunity to finish your dream home. Scenic tree-filled lot complete with a picturesque creek for a serene, natural setting. This single family home has been gutted and is awaiting a homeowner ready-to-build, offering the perfect foundation to craft your custom house. Only a foundation and frame exists. Near top schools in the state. Exceptional access to both I-95 and I-90, making

  Eric Glassoff Coldwell Banker Realty - Brookline

  217 Summer St, Weston, MA 02493
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  /34

  $13,850,000

  • 7 Beds
  • 11 Baths
  • 12,120 Sq Ft

  21 Chestnut St, Weston, MA 02493

  This modern estate is a seamless blend of striking architecture and luxurious design. A grand 2 story foyer with soaring ceilings and a dramatic staircase creates a stunning first impression, while walls of glass connect the home’s interior to the scenic outdoors. The main level features a gourmet kitchen with a hidden pantry, chef’s kitchen, and office nook, flowing into a spacious family room

  Maggie Gold Seelig MGS Group Real Estate LTD

  21 Chestnut St, Weston, MA 02493
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  /28

  $2,750,000

  • 5 Beds
  • 4.5 Baths
  • 6,423 Sq Ft

  423 Concord Rd, Weston, MA 02493

  This striking five-bedroom contemporary home, set on more than 1.8 acres, seamlessly blends modern design with the natural beauty of its surroundings. With 6,400 square feet of living space, it’s ideally located next to miles of conservation land and trails—perfect for those seeking a private retreat in nature. Upon entering, you're greeted by a spacious foyer bathed in natural light from

  Dean Poritzky Engel & Völkers Wellesley

  423 Concord Rd, Weston, MA 02493
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  /42

  $3,249,000

  • 4 Beds
  • 5 Baths
  • 4,836 Sq Ft

  29 Willard Rd, Weston, MA 02493

  Sophisticated, sleek modern home. 2025 year built with one year builders warranty on cul-de-sac. Oversized floor-to-ceiling windows flood interiors with natural light. Open concept family and dining rooms flow with modern show-kitchen enhanced by light oak prep kitchen. Family room features statement gas fireplace and sliding door access to covered patio w/ outdoor kitchen accented by creative

  Chaplin Partners Compass

  29 Willard Rd, Weston, MA 02493
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  /31

  $3,595,000 Open Sun 12PM - 1PM

  • 5 Beds
  • 6 Baths
  • 6,252 Sq Ft

  22 Chadwick Rd, Weston, MA 02493

  Situated in a coveted Southside neighborhood on an ended way, this sophisticated Colonial has been meticulously updated & expanded, offering perfect spaces for entertaining & family enjoyment. The inviting foyer flows seamlessly into a library w/custom built-ins & a fireplaced living room overlooking the private grounds. The kitchen has an adjoining eat-in area, opening to a family room w/access

  Beyond Boston Properties Group Compass

  22 Chadwick Rd, Weston, MA 02493
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  /36

  $3,450,000

  • 3 Beds
  • 3.5 Baths
  • 4,438 Sq Ft

  23 Pine Summit Cir Unit 23, Weston, MA 02493

  Luxurious home with all the amenities. Prime location in Highland Meadows premier 55+ community. Newly renovated in 2022, this 4,438 sq ft home has an open floor plan and large windows giving a very light and warm feeling. First floor with large kitchen plus island opens to family room with gas fireplace. Walk in food pantry plus new Thermador/ SubZero appliances. Banquet size dining room with

  Melissa Dailey Coldwell Banker Realty - Wellesley

  23 Pine Summit Cir Unit 23, Weston, MA 02493
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  /39

  $3,200,000 Open Sun 11:30AM - 1PM

  • 5 Beds
  • 7 Baths
  • 6,096 Sq Ft

  7 Rockport Rd, Weston, MA 02493

  Elegant & Spacious Weston Estate on a Quiet StreetNestled on a peaceful street in Weston, this stunning estate offers over 6,000 sqft of luxurious living space on 1.39 acres of beautifully maintained land. With 13 rooms, 5 bedrooms, and 7 bathrooms, this home is perfect for a large family or an au pair arrangement.Step inside to be greeted by soaring ceilings and an abundance of natural light,

  Vito Capraro Aluxety

  7 Rockport Rd, Weston, MA 02493

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