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Homes for Sale in Weston, MA with 5-Bedrooms

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  • /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
  • /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
  • /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
  • /42

    $3,650,000

    $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
  • /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 12PM - 1PM
    • 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
  • /5

    $7,295,000

    • 5 Beds
    • 6.5 Baths
    • 8,889 Sq Ft

    50 Laurel Rd, Weston, MA 02493

    Exceptional new home in one of Weston's most coveted neighborhoods. Spectacular naturally screened & private fully level lot with sports court and options for pool & accessory pool house with two car garage. The main house features 8889 sq ft with 5-6 bedrooms & en-suite bathrooms, and was thoughtfully designed by acclaimed architect Greg Legault featuring an open floor plan with an abundance of

    P. Matthew Harkins Walden Realty Group LLC

    50 Laurel Rd, Weston, MA 02493
  • /42

    $5,995,000

    • 5 Beds
    • 7 Baths
    • 8,860 Sq Ft

    10 Hitching Post Ln, Weston, MA 02493

    New construction in one of Weston’s most exclusive neighborhoods, blending transitional design, exceptional craftsmanship, and state-of-the-art systems. This sun-filled home offers 5 bedrooms, 5 full and 2 half baths, 10’ ceilings, oversized windows, and curated finishes that offer scale and warmth. The chef’s kitchen features 36" refrigerator and a 36” freezer, double ovens, wine tower, and

    Denise Mosher Coldwell Banker Realty - Weston

    10 Hitching Post 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
  • /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
  • /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
  • /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

    $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

    • 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
  • /41

    $7,590,000

    $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
  • /39

    $3,750,000

    • 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
  • /32

    $7,295,000

    • 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
  • /42

    $2,395,000

    Open Thu 11AM - 12:30PM
    • 5 Beds
    • 4.5 Baths
    • 3,739 Sq Ft

    55 Coburn Rd, Weston, MA 02493

    Discover timeless elegance at 55 Coburn Road, a beautifully preserved 1896 Colonial Revival home nestled in Weston's historic estate neighborhood. Set on nearly one acre of serene, tree-lined grounds, the home offers 3,739 square feet of living space with 5 bedrooms and 4.5 bathrooms. The sellers have meticulously updated the home from top to bottom, blending historic charm with modern comfort

    Jonathan Russell Columbus and Over Group, LLC

    55 Coburn Rd, Weston, MA 02493
  • /30

    $2,995,000

    • 5 Beds
    • 5.5 Baths
    • 5,000 Sq Ft

    27 Wood Ridge Rd, Weston, MA 02493

    Modern accents and timeless Colonial warmth come together in this inviting home bordering Weston’s treasured conservation land and trail network. Tucked away at the end of a quiet street and surrounded by mature woods, the landscaped property offers exceptional privacy and a peaceful natural setting. The home features a classic library with custom millwork, fireplace and coffered ceiling,

    Wendy Reservitz William Raveis R.E. & Home Services

    27 Wood Ridge 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

    $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
  • /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
  • /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
  • /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
  • /42

    $1,995,000

    $100K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 4,338 Sq Ft

    5 Summer St, Weston, MA 02493

    Large 6-bedroom Cape offering one-floor living in an excellent commuter location with mature specimen trees. Separate entrance foyer with 2 home offices and half bath connects to the main house through a paneled study, ideal for an in-law suite or home business. Sited privately above the road, the 1.26-acre lot is a gardener’s paradise featuring a remarkable collection of mature exotic trees and

    Chaplin Partners Compass

    5 Summer St, Weston, MA 02493
  • /36

    $6,950,000

    $500K PRICE DROP
    • 5 Beds
    • 7 Baths
    • 8,451 Sq Ft

    15 Myles Standish Rd, Weston, MA 02493

    Architecturally striking Prairie-style contemporary custom built with a refined focus on nature, craftsmanship, and simplicity. South-facing open layout with walls of glass overlooking professionally designed grounds and serene private setting. Heated pool with automatic cover and integrated jacuzzi, with pool and landscape irrigation supplied by a private well. German-engineered windows offer

    Alptug Kantar Boston Brokerage Group

    15 Myles Standish Rd, Weston, MA 02493
  • /34

    $4,150,000

    Open Sun 2:30PM - 3:30PM $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
  • /36

    $6,500,000

    • 5 Beds
    • 9 Baths
    • 11,820 Sq Ft

    41 Skating Pond Rd, Weston, MA 02493

    Privately set on 2.42 acres in Weston’s highly coveted South Side Country Club area, 41 Skating Pond Road offers over 11,000 sf of exceptional living space, recently renovated to the highest standard of fit & finish. The residence features 5 en suite bedrooms, 7 full baths, 2 half baths & attached 3 car garage. A dramatic 2 story foyer fills the home with natural light, while refined interiors

    Collin Sullivan William Raveis R.E. & Home Services

    41 Skating Pond Rd, Weston, MA 02493
  • /41

    $3,139,900

    New Construction Open Sat 12PM - 2PM $455K PRICE DROP
    • 5 Beds
    • 6.5 Baths
    • 7,317 Sq Ft

    6 Clifford Ln, Weston, MA 02493

    Welcome to Trails End! A luxury subdivision on a private dead-end street. Compare the value, this home is offered at $437 psf vs the average new home in Weston is over $700 psf. 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

    Gary Litchfield Mass. Real Estate Solutions, LLC

    6 Clifford Ln, Weston, MA 02493
  • /28

    $5,900,000

    $300K PRICE DROP
    • 5 Beds
    • 7 Baths
    • 11,300 Sq Ft

    741 Boston Post Rd, Weston, MA 02493

    A modern masterpiece born of a dramatic barn conversion, completed in 2023. This one-of-a-kind residence blends rustic charm & contemporary luxury. Featuring soaring ceilings, a 20' high wall of windows, exposed beams, and sun-drenched living spaces. The dreamy kitchen includes modern cabinetry, Miele appliances and an enormous quartz-wrapped island. The living areas flow effortlessly to outdoor

    Amy Rutkowski A. Rutkowski Realty, Inc.

    741 Boston Post Rd, Weston, MA 02493
  • /40

    $11,750,000

    • 7 Beds
    • 8.5 Baths
    • 16,369 Sq Ft

    15 Claridge Dr, Weston, MA 02493

    Set on 3.75 acres of beautifully landscaped grounds, this extraordinary Country Manor was designed by architect Thomas Catalano with landscape design by Morgan Wheelock. Positioned on a gentle slope overlooking sweeping lawns, the home offers a peaceful and private setting. The exterior blends finely finished stucco with Dolomitic limestone and Chelmsford granite, topped with a Vermont slate roof

    Dean Poritzky Engel & Völkers Wellesley

    15 Claridge Dr, Weston, MA 02493
  • /2

    $1,700,000

    • 7 Beds
    • 3.5 Baths
    • 4,158 Sq Ft

    126 Charles St (Aub), Newton, MA 02466

    For Sale - Auburndale/ Newton 3 Family Home.Existing, legal three family (non-conforming with special permit) on a large parcel (8,960 SF) of land in Auburndale (Newton) MA.Great location with a view of the Charles River.Building definitely needs renovation work.Complete teardown and rebuild of three large units may be the play with this property.The property next to this (132 Charles Street) is

    Tom Slayton CRG Commercial

    126 Charles St (Aub), Newton, MA 02466
  • /39

    $5,200,000

    $295K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 7,345 Sq Ft

    48 Scotch Pine Rd, Wellesley Hills, MA 02481

    Incredible custom renovated 5 bedroom home that has undergone significant upgrades making this one of Wellelsey's sought after properties. White washed brick face exterior with pea stone drive and parking court all trimmed in cobblestone creates a gorgeous approach. Stunning 2 story foyer with herring bone floors greets you into this welcoming 7300 sq ft space on nearly one acre of flat and

    Melissa Dailey Coldwell Banker Realty - Wellesley

    48 Scotch Pine Rd, Wellesley Hills, MA 02481
  • /37

    $3,285,000

    $195K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 5,073 Sq Ft

    8 Oakdale Ave, Wellesley, MA 02482

    Experience the epitome of luxury in this stunning new Colonial masterpiece in Wellesley, nestled on a serene dead-end street. With 5 bedrooms and 5 baths sprawled over 5,000 sq. ft., every inch exudes elegance. Experience gleaming hardwood floors beneath soaring 9’ ceilings, embraced by sunlit spaces. The first floor boasts refined living and dining areas, a chef’s eat-in kitchen with bespoke

    Donahue Maley & Burns Team Compass

    8 Oakdale Ave, Wellesley, MA 02482
  • /41

    $5,100,000

    $495K PRICE DROP
    • 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

5-Bedroom Home Prices in Weston, MA

5-Bedroom Price Trends

Median 5-Bedroom Home Price
$3,200,000
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