35

Weston, MA Homes for Sale with Acreage

Section Image
  • /36

    $3,450,000

    $800K PRICE DROP
    • 4 Beds
    • 6 Baths
    • 5,018 Sq Ft

    105 Summer St, Weston, MA 02493

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

    Mizner+ Montero Gibson Sotheby's International Realty

    105 Summer St, Weston, MA 02493
  • /35

    $1,945,000

    Open Sat 11:30AM - 12:30PM
    • 3 Beds
    • 3.5 Baths
    • 3,607 Sq Ft

    633 Boston Post Rd, Weston, MA 02493

    Back on market after Seller secured housing! Beautifully sited on 1.16± acres in Weston’s coveted Town Center, this classic Colonial offers timeless appeal, privacy, and exceptional livability. Inside, enjoy 3,607± sq ft of well-designed space including formal living room with fireplace, elegant dining room, and sun-filled family room opening to large deck overlooking pool and landscaped grounds.

    Jonathan Caldwell ACRE Property Advisors LLC

    633 Boston Post Rd, Weston, MA 02493
  • /42

    $9,990,000

    $510K PRICE DROP
    • 5 Beds
    • 10 Baths
    • 11,352 Sq Ft

    70 Possum Rd, Weston, MA 02493

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

    Rose Hall Blue Ocean Realty, LLC

    70 Possum Rd, Weston, MA 02493
  • /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
  • /38

    $4,850,000

    • 4 Beds
    • 3 Baths
    • 6,442 Sq Ft

    80 Doublet Hill Rd, Weston, MA 02493

    Sophisticated extensively renovated ranch-style estate residence in Weston’s coveted South Side Golf Club neighborhood. Privately sited on approximately 2 landscaped acres along a picturesque tree-lined street with direct access to conservation land and walking trails. Designed for luxury living and entertaining, the main level features a grand foyer, raised ceilings, oversized windows, and

    Marjorie Gold Hammond Residential Real Estate

    80 Doublet Hill 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

    • 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
  • /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
  • /27

    $4,995,000

    $255K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 7,100 Sq Ft

    10 Chandler Cir, Weston, MA 02493

    Beautiful custom built Modern Classic home sited in a premier estate location on the south side of Weston. Designed by acclaimed architect Marcus Gleysteen and built by luxury home builder Wellen Construction this property has an absolutely enchanting setting adjacent to 30 acres of conservation land and trails. Reminiscent of a country estate in Vermont it evokes relaxed comfort with finely

    rosemary mccready Compass

    10 Chandler Cir, Weston, MA 02493
  • /31

    $3,095,000

    Open Sat 11AM - 12:30PM $355K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 7,195 Sq Ft

    24 Trailside Rd, Weston, MA 02493

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

    Mizner+ Montero Gibson Sotheby's International Realty

    24 Trailside Rd, Weston, MA 02493
  • /42

    $6,750,000

    Open Sun 1PM - 2:30PM
    • 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
  • /40

    $2,499,900

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

    130 Summer St, Weston, MA 02493

    Welcome to 130 Summer St. This spectacular approx 5181 sqft Contemporary masterpiece is set on 2.67 private acres featuring sprinkler system and backyard sports court. Built for entertaining, the chefs kitchen boasts a large center island, Wolf & Sub-Zero appliance, add'l refrigerator / ice maker built into bar, and a custom fireplace pizza oven. Sliders leading out front, with open flow leading

    David Newbould Results Realty

    130 Summer St, 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

    $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
  • /40

    $1,750,000

    Open Sat 1:30PM - 3PM $140K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,345 Sq Ft

    40 Hobbs Brook Rd, Weston, MA 02493

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

    Mizner+ Montero Gibson Sotheby's International Realty

    40 Hobbs Brook Rd, Weston, MA 02493
  • /30

    $1,795,000

    • 3 Beds
    • 3 Baths
    • 4,705 Sq Ft

    242 Winter St, Weston, MA 02493

    Set on a beautifully landscaped 1.43-acre lot, this contemporary Cape-style home blends spacious living with architectural character and resort-style amenities. Offering 3 bedrooms, including a private primary suite with en suite bath, the home is designed for both everyday comfort and effortless entertaining. The dramatic great room features soaring ceilings, skylights, fireplace, and wet bar,

    Denise Mosher Coldwell Banker Realty - Weston

    242 Winter St, Weston, MA 02493
  • /38

    $3,750,000

    Open Sun 11AM - 12:30PM
    • 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 staircase opens to a front-to-back living room with a fireplace and a formal dining room. The newly renovated kitchen with a breakfast area opens to a sunroom overlooking the idyllic grounds with a waterfall and Koi pond. An inviting family room with a fireplace, mudroom and powder room complete the

    Mizner+ Montero Gibson Sotheby's International Realty

    64 Country Dr, Weston, MA 02493
  • /15

    $2,399,000

    $201K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,395 Sq Ft

    416 Conant Rd, Weston, MA 02493

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

    Derek Greene The Greene Realty Group

    416 Conant Rd, Weston, MA 02493
  • /10

    $5,395,000

    • Land
    • 7.28 Acres
    • $741,071 per Acre

    475 Glen Rd, Weston, MA 02493

    Discover 7.28 acres of pristine land offering exceptional privacy, tranquility, and natural beauty in one of Massachusetts’ most sought-after communities. This remarkable parcel presents a rare opportunity to create a custom luxury estate surrounded by mature trees, open space, and a serene natural landscape. Located in Weston, the property offers the perfect balance of peaceful country living

    Julie Harrison Gibson Sotheby's International Realty

    475 Glen 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
  • /42

    $5,999,000

    • 4 Beds
    • 7 Baths
    • 7,600 Sq Ft

    44 Meadowbrook Rd, Weston, MA 02493

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

    Mizner+ Montero Gibson Sotheby's International Realty

    44 Meadowbrook Rd, Weston, MA 02493
  • /27

    $1,675,000

    • 4 Beds
    • 3 Baths
    • 2,840 Sq Ft

    37 School St, Weston, MA 02493

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

    Denise Mosher Coldwell Banker Realty - Weston

    37 School St, Weston, MA 02493
  • /38

    $9,500,000

    • 6 Beds
    • 9 Baths
    • 12,117 Sq Ft

    43 Pine St, Weston, MA 02493

    One of South Side Weston’s most exceptional estate offerings, privately sited on 2.4 breathtaking resort-like acres. Meticulously maintained and masterfully renovated, this distinguished residence seamlessly blends timeless architecture with sophisticated modern luxury. Sun-drenched interiors and exquisite craftsmanship define every space, highlighted by a spectacular vaulted family room and

    Jill Boudreau eXp Realty LLC - Corporate Office

    43 Pine St, Weston, MA 02493
  • /38

    $4,595,000

    $400K PRICE DROP
    • 6 Beds
    • 7 Baths
    • 7,000 Sq Ft

    21 Westerly Rd, Weston, MA 02493

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

    Melissa Dailey Coldwell Banker Realty - Wellesley

    21 Westerly Rd, Weston, MA 02493
  • /38

    $4,388,000

    $300K PRICE DROP
    • 5 Beds
    • 7 Baths
    • 8,844 Sq Ft

    568 Wellesley St, Weston, MA 02493

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

    Rose Hall Blue Ocean Realty, LLC

    568 Wellesley St, Weston, MA 02493
  • /42

    $1,995,000

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

    5 Summer St, Weston, MA 02493

    Large 5-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

    $6,975,000

    Open Thu 5PM - 7PM
    • 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
  • /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
  • /35

    $3,995,000

    $430K 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
  • /42

    $2,480,000

    $80K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 4,747 Sq Ft

    39 Kings Grant Rd, Weston, MA 02493

    Tucked into Weston’s sought-after Kings Grant neighborhood, this expanded and versatile home offers exceptional flexibility for today’s lifestyle needs. The dramatic living room features soaring ceilings, a wood-burning fireplace, and direct access to a bright sunroom, creating a warm and inviting setting for everyday living and entertaining.The kitchen flows seamlessly into the dining area,

    Keystone Homes Group Keller Williams Realty Boston Northwest

    39 Kings Grant Rd, Weston, MA 02493
  • /36

    $6,750,000

    • 5 Beds
    • 9 Baths
    • 10,819 Sq Ft

    15 Brown St, Weston, MA 02493

    Introducing a timeless European inspired mansion with a private gate and elegant marble fountain. This custom estate is situated on 3 acres. A spectacular pool and spa complemented by a fully equipped pool house with a kitchen adorn the grounds. A beautiful wrought iron fence embraces the entire estate which includes stone patios and tennis court. The grand entry and living and dining rooms boast

    Mizner+ Montero Gibson Sotheby's International Realty

    15 Brown St, Weston, MA 02493

Home Price Trends

Median Sale Price
$2,452,500
Median Single Family Sale Price
$2,647,500
Median Townhouse Sale Price
$881,250
Median 2 Bedroom Sale Price
$844,200
Median 1 Bedroom Sale Price
$441,000
Average Price Per Sq Ft
$614
Number of Homes for Sale
47
Last 12 months Home Sales
138
Months of Supply
4.10
Median List Price
$2,695,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
2%
How to Buy a Home How to Finance a Home How to Sell a Home