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Weston, MA Homes for Sale with Pool

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  • /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 Sun 2:30PM - 3:30PM
    • 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
  • /29

    $925,000

    Open Sun 1PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    130 Viles St, Weston, MA 02493

    Enjoy the feel of single-family living in this bright townhome-style home with no condo fee, separately metered utilities, a separate water meter, and an exclusive fenced yard. The open main level offers warm wood floors, recessed lighting, a modern white kitchen with island seating and stainless steel appliances, plus easy flow to the dining and living areas. A private deck overlooks the fenced

    Yuan Li Yuan's Team Realty

    130 Viles St, 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
  • /33

    $2,295,000

    $200K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,157 Sq Ft

    23 Stony Brook Rd, Weston, MA 02493

    Pristine 4-bedroom Sweidler Colonial offers an open floor plan, enhanced by beautiful built-ins and millwork throughout. Custom cherry kitchen with large center island, opens to a vaulted, fireplaced family room - truly the heart of this home! The main level also features a dining room, fireplaced living room, two versatile home offices, half bath, and laundry. The second floor includes a primary

    Jeanne Fleming Gibson Sotheby's International Realty

    23 Stony Brook 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
  • /33

    $1,795,000

    • 3 Beds
    • 3 Baths
    • 3,264 Sq Ft

    44 Old Rd, Weston, MA 02493

    Contemporary and expanded 3-bedroom Cape set on a beautifully landscaped one-acre lot just minutes from Weston town center. Thoughtfully designed, this elegant home blends timeless appeal with modern comfort, offering exceptional craftsmanship, generous storage, and well-designed living spaces. The well-appointed kitchen features high-end appliances, custom cabinetry, ample workspace, and opens

    Karen Kirk Engel & Völkers Wellesley

    44 Old Rd, 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
  • /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
  • /27

    $5,250,000

    • 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

    $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

    • 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
  • /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
  • /40

    $3,250,000

    • 4 Beds
    • 5.5 Baths
    • 6,419 Sq Ft

    1 Graystone Ln, Weston, MA 02493

    This sophisticated, contemporary Colonial, custom built in 1995, offers over 6,400 sq ft of beautifully updated living space with high-end finishes throughout. Ideally sited on a private Southside cul-de-sac, it’s surrounded by meticulously maintained, English garden–style grounds, creating a serene setting.Featuring 4 bedrooms, 5 full baths, and 1 half bath, the home blends timeless elegance

    Dean Poritzky Engel & Völkers Wellesley

    1 Graystone Ln, 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
  • /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
  • /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

    $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

    $4,388,000

    $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

    $6,950,000

    $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
  • /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
$2,490,000
Median Single Family Sale Price
$2,650,000
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
$615
Number of Homes for Sale
49
Last 12 months Home Sales
140
Months of Supply
4.20
Median List Price
$2,695,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
4%
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