32

5-Bedroom Homes for Sale in Weston, MA

Section Image Section Image
  • /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

    Agent Photo

    Yassien Youssef

    Compass

    (339) 218-4223

    51 Willard Rd, Weston, MA 02493
  • /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
  • /42

    $6,200,000

    • 5 Beds
    • 7 Baths
    • 11,300 Sq Ft

    741 Boston Post Rd, Weston, MA 02493

    A modern masterpiece born from a dramatic barn conversion, this one-of-a-kind home completed in 2023 blends rustic charm with contemporary luxury. The residence offers soaring ceilings, a 20' high wall of windows, exposed beams, and sun-drenched living spaces.The kitchen features sleek cabinetry, Miele appliances, and a huge quartz-wrapped island. The expansive living areas flow to outdoor

    Amy Rutkowski A. Rutkowski Realty, Inc.

    741 Boston Post Rd, Weston, MA 02493
  • /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
  • /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
  • /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
  • /29

    $7,498,000

    • 5 Beds
    • 9 Baths
    • 11,300 Sq Ft

    180 Highland St, Weston, MA 02493

    This gated custom-built estate exudes elegance and unparalleled craftsmanship. Set on three sprawling acres and surrounded by conservation 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

    Teri Adler MGS Group Real Estate LTD - Wellesley

    180 Highland St, Weston, MA 02493
  • /38

    $7,850,000

    • 6 Beds
    • 6.5 Baths
    • 8,800 Sq Ft

    12 Robin Rd, Weston, MA 02493

    This Contemporary designed by a prominent architect and located in the Country Club neighborhood is inspired by the Japandi style which combines the serenity of Japanese architecture with the organic nature of Scandinavian design. A father/son collaboration, this home’s sophisticated details abound from the illuminated floating staircase to a semi-enclosed courtyard with a deck and sunken patio.

    Mizner+ Montero Gibson Sotheby's International Realty

    12 Robin Rd, Weston, MA 02493
  • /7

    $6,488,000 New Construction

    • 6 Beds
    • 8 Baths
    • 7,501 Sq Ft

    15 Whitney Tavern Rd, Weston, MA 02493

    New construction meets timeless design at this striking estate in Weston. Set on a beautifully landscaped lot, this home blends classic architecture with sleek modern finishes. Sun-bathed rooms, high ceilings, and seamless indoor-outdoor flow define the main level, which includes a guest or first-floor primary suite, 2 powder rooms, and a chef’s kitchen with Wolf/Sub-Zero appliances. The second

    Maggie Gold Seelig MGS Group Real Estate LTD

    15 Whitney Tavern Rd, Weston, MA 02493
  • /33

    $5,350,000

    • 7 Beds
    • 7 Baths
    • 7,262 Sq Ft

    200 Cliff Rd, Wellesley Hills, MA 02481

    Much admired 7 bedroom, 7000+sf estate home on an acre of manicured lawns on famed Cliff Road. Built and re designed by two of New England’s most acclaimed architects, this home boasts the grandeur of stately proportions and sumptuous millwork with a newly renovated and superbly equipped chef’s Kitchen and butler’s pantry with adjacent family room. A banquet sized dining room and gracious living

    Donahue Maley & Burns Team Compass

    200 Cliff Rd, Wellesley Hills, MA 02481
  • /28

    $3,350,000

    • 5 Beds
    • 7.5 Baths
    • 7,000 Sq Ft

    50 Fairview Rd, Weston, MA 02493

    This elegant Colonial estate offers over 7,000 square feet of sun-filled living space, privately sited on nearly an acre in a sought-after neighborhood near conservation land and trails. With five bedrooms and seven full baths, the home features an open floor plan ideal for modern living and entertaining. A dramatic two-story foyer leads to beautifully detailed living and dining rooms. The chef’s

    Dean Poritzky Engel & Völkers Wellesley

    50 Fairview Rd, Weston, MA 02493
  • /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
  • /31

    $1,750,000

    • 5 Beds
    • 3 Baths
    • 3,265 Sq Ft

    19 Bakers Hill Rd, Weston, MA 02493

    Set on a serene, flat lot with sidewalks to Weston center, access to top schools, miles of trails, and all major commuting routes, this spacious 10 room, 4-5 bedroom, 3 bath raised ranch offers the perfect blend of comfort and convenience. The sun-filled main level features gleaming hardwood floors, a large living room with a picture window and fireplace, a formal dining room, an updated eat-in

    Denise Mosher Coldwell Banker Realty - Weston

    19 Bakers Hill Rd, Weston, MA 02493
  • /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
  • /38

    $4,200,000

    • 6 Beds
    • 6.5 Baths
    • 9,383 Sq Ft

    48 Myles Standish Rd, Weston, MA 02493

    This extraordinary home seamlessly blends timeless elegance with modern Scandinavian aesthetics. The open design features an expansive kitchen with a soaring beamed cathedral ceiling accented with multiple skylights. Graceful archways lead to the living and dining rooms enhanced with a striking double-sided fireplace. A rich wood-paneled office is privately situated. A spacious family room with

    Mizner+ Montero Gibson Sotheby's International Realty

    48 Myles Standish Rd, Weston, MA 02493
  • /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
  • /30

    $2,900,000

    • 5 Beds
    • 2.5 Baths
    • 4,403 Sq Ft

    117 Deer Path Ln, Weston, MA 02493

    This timeless Colonial home has been beautifully updated and meticulously maintained, offering exceptional indoor-outdoor living and entertaining. Ideally sited on 1.4 acres in one of Weston's most coveted south side neighborhoods, this five-bedroom home provides privacy yet is close to town, schools, and the Mass Pike. More than $800,000 was invested in renovations include stunning landscaping

    Dean Poritzky Engel & Völkers Wellesley

    117 Deer Path Ln, Weston, MA 02493
  • /26

    $2,780,000 Open Sat 1:30PM - 3:30PM

    • 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
  • /30

    $3,095,000

    • 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
  • /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
  • /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
  • /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
  • /42

    $4,495,000

    • 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
  • /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
  • /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
  • /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
  • /42

    $19,850,000

    • 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
  • /2

    $3,199,900

    • 5 Beds
    • 6 Baths
    • 6,300 Sq Ft

    2 Clifford Ln, Weston, MA 02493

    Trails End Subdivision! We are proud to present our 4th offering in this exclusive private dead-end cul-de-sac. This colonial/farmhouse design is unique and luxurious featuring 6,300 sq. ft., 12 rooms and 6 baths. This home is complete and ready to move in.

    Gary Litchfield Mass. Real Estate Solutions, LLC

    2 Clifford Ln, Weston, MA 02493
  • /31

    $13,955,000

    • 7 Beds
    • 8.5 Baths
    • 13,555 Sq Ft

    15 Claridge Dr, Weston, MA 02493

    Enter through gates and arrive at an extraordinary English Country Manor sited on 3.75 acres on a private road in a premier estate neighborhood on the south side of Weston. Designed by a legendary architect and featured in major magazines, this one of a kind custom built residence offers 20 rooms of jaw dropping beauty including a spectacular two story grand entrance hall. This rare property is

    rosemary mccready Compass

    15 Claridge Dr, Weston, MA 02493
  • /42

    $6,888,000 New Construction

    • 7 Beds
    • 11 Baths
    • 10,642 Sq Ft

    154 Newton St, Weston, MA 02493

    Custom modern new construction on 2.26 acres overlooking the Weston Golf Club. Generous spaces with 3 primary-sized suites, 33' x 44' indoor court, and unusual ceiling height on all four levels: 11’ 1st floor, 10’10” 2nd floor, 11’5” fitness / golf sim area, and 20’11” recreation court. 6+ garage bays. Steel beam construction. Walnut kitchen with 16’ island, large pantry, and oversized back deck.

    Chaplin Partners Compass

    154 Newton St, Weston, MA 02493
  • /41

    $3,349,900 New Construction

    • 5 Beds
    • 6.5 Baths
    • 7,317 Sq Ft

    6 Clifford Ln, Weston, MA 02493

    Welcome to Trails End! A luxury subdivision of 6 lots on a private dead-end street. This is our third offering and is a spectacular 14 room modern farmhouse style. Enter into a welcoming foyer and open floor plan featuring a chefs kitchen and oversize island Breakfast area opens up to a large family room showcasing a large gas fireplace, a guest suite, home office and mudroom round out the 1st

    Gary Litchfield Mass. Real Estate Solutions, LLC

    6 Clifford Ln, Weston, MA 02493
  • /7

    $7,295,000 New Construction

    • 5 Beds
    • 7.5 Baths
    • 8,200 Sq Ft

    5 Deer Path Ln, Weston, MA 02493

    Welcome to the pinnacle of luxury living in the heart of Weston's coveted Southside. This extraordinary opportunity invites you to work with a highly-respected builder and acclaimed architect to bring your dream home to life. Situated on a lushly-landscaped, generous lot, this custom masterpiece will offer unparalleled privacy and sophistication. Upon completion, this exquisite residence will

    Beyond Boston Properties Group Compass

    5 Deer Path Ln, Weston, MA 02493

Home Trends in Weston, MA

Housing Trends

Median Sale Price
$2,450,000
Median Single Family Sale Price
$2,750,000
Median Townhouse Sale Price
$1,550,500
Median 2 Bedroom Sale Price
$826,000
Median 1 Bedroom Sale Price
$553,000
Average Price Per Sq Ft
$628
Number of Homes for Sale
43
Last 12 months Home Sales
123
Months of Supply
4.20
Median List Price
$2,732,500
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
17%
How to Buy a Home How to Finance a Home How to Sell a Home