5,493

Westwood, MA Homes

Section Image
  • /30

    $5,999,000

    $1M PRICE DROP
    • 6 Beds
    • 6.5 Baths
    • 9,342 Sq Ft

    429 Summer St, Westwood, MA 02090

    This magnificent Georgian Colonial, set on 12+ acres in the heart of Westwood’s estate area, was designed by Johnson, Craven & Gibson and inspired by William Lawrence Bottomley’s Milburne in Richmond, VA. The stunning entry hall with its sweeping staircase is flanked by exquisite formal living and dining rooms, a classic library, and a wonderful breakfast room, all overlooking the south-facing

    John Boyle LandVest, Inc.

    429 Summer St, Westwood, MA 02090
  • /35

    $1,095,500

    Sold Dec 15, 2025

    130 Cobleigh St, Westwood, MA 02090

    • 3 Beds
    • 2.5 Baths
    • 1,920 Sq Ft
    • Built 1952

    Last Sold Summary

    • 10% Above List Price
    • $571/SF
    • 7 Days On Market

    Current Estimated Value $1,092,785

    Last Listing Agent Elena Price Coldwell Banker Realty - Westwood

    130 Cobleigh St, Westwood, MA 02090
    • /16

      Est $1,921,368

      Not Listed For Sale

      5 Fox Meadow Dr, Westwood, MA 02090

      5 Fox Meadow Dr, Westwood, MA 02090

      Last Sold Summary

      • 129 Days On Market

  • /32

    $4,000,000

    • 5 Beds
    • 4 Baths
    • 5,090 Sq Ft

    157 Grove St, Westwood, MA 02090

    A private estate on 11 spectacular acres, this distinguished 1912 residence offers timeless character, exceptional privacy and resort-like living in one of the Boston area's most desirable settings. The 5-bedroom home features 4,500+ square feet of beautifully maintained living space, blending classic architectural details with modern comfort. Grand living, dining and sunrooms, an intimate

    Bell Property Partners Compass

    157 Grove St, Westwood, MA 02090
  • /30

    $1,010,000

    Sold Jun 15, 2026

    70 Cobleigh St, Westwood, MA 02090

    • 3 Beds
    • 1.5 Baths
    • 2,264 Sq Ft
    • Built 1953

    Last Sold Summary

    • 2% Above List Price
    • $446/SF
    • 6 Days On Market

    Current Estimated Value $1,001,484

    Last Listing Agent Tom Aaron Coldwell Banker Realty - Wellesley

    70 Cobleigh St, Westwood, MA 02090
    • /42

      Est $1,227,687

      Not Listed For Sale

      14 Dean St, Westwood, MA 02090

      • 4 Beds
      • 3.5 Baths
      • 2,340 Sq Ft
      • Built 2012
      14 Dean St, Westwood, MA 02090

      Last Sold Summary

      • 6 Days On Market

  • /27

    $945,000

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    13-15 Gay St, Westwood, MA 02090

    Rare opportunity to own a two family duplex style home in Westwood center. Ideal for owner occupant or investor. Potential to expand or condo conversion pending town approvals. One unit currently rented and the other side is now vacant. The yard is spacious allowing room for enjoyment. There is a fenced area with an inground, heated, salt-water pool. Each unit shares a front porch and back deck.

    Elena Price Coldwell Banker Realty - Westwood

    13-15 Gay St, Westwood, MA 02090
  • /24

    $9,700,000

    Sold Dec 12, 2025

    300 Summer St, Westwood, MA 02090

    • 6 Beds
    • 9 Baths
    • 10,309 Sq Ft
    • Built 2017

    Last Sold Summary

    • 22% Below List Price
    • $941/SF
    • 513 Days On Market

    Current Estimated Value $9,499,164

    Last Listing Agent John Boyle LandVest, Inc.

    300 Summer St, Westwood, MA 02090
    • /31

      Est $1,106,492

      Not Listed For Sale

      548 Oak St, Westwood, MA 02090

      • 3 Beds
      • 2.5 Baths
      • 2,000 Sq Ft
      • Built 1963
      548 Oak St, Westwood, MA 02090

      Last Sold Summary

      • 26 Days On Market

  • /41

    $995,000

    Pending
    • 3 Beds
    • 2 Baths
    • 2,057 Sq Ft

    5 Stanford Dr, Westwood, MA 02090

    Spacious and bright, 5 Stanford Drive sits on a .96-acre fenced-in corner lot in a sought-after Westwood neighborhood. Inside, hardwood floors and abundant natural light highlight a layout designed for easy living. The kitchen opens to the main living area, and the living room features a newly installed wood-burning stove with a stone mantel. The main level includes 3 generous bedrooms, a primary

    Amanda Rosen Real Broker MA, LLC

    5 Stanford Dr, Westwood, MA 02090
  • /41

    $2,650,000

    Sold Jun 01, 2026

    39 Westbrook Ln, Westwood, MA 02090

    • 5 Beds
    • 4.5 Baths
    • 5,266 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Below List Price
    • $503/SF
    • 65 Days On Market

    Current Estimated Value $2,680,995

    Last Listing Agent Elena Price Coldwell Banker Realty - Westwood

    39 Westbrook Ln, Westwood, MA 02090
    • /39

      Est $1,199,609

      Not Listed For Sale

      215 Briar Ln, Westwood, MA 02090

      • 3 Beds
      • 2.5 Baths
      • 2,383 Sq Ft
      • Built 1964
      215 Briar Ln, Westwood, MA 02090

      Last Sold Summary

      • 6 Days On Market

  • /30

    $2,795,000

    $60K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 5,700 Sq Ft

    36 Kingswood Rd, Westwood, MA 02090

    Beautifully crafted NEW CONSTRUCTION home offering over 5,700 sf of finished living space, including a newly completed lower level. Privately situated on a cul-de-sac and abutting Hale Reservation, this exceptional property combines luxury, comfort, and thoughtful design. A dramatic central staircase anchors the open floor plan, while the chef’s kitchen features premium appliances, custom

    Roula Gallis Bakis Artemis Realty

    36 Kingswood Rd, Westwood, MA 02090
  • /26

    $1,190,000

    Sold Oct 09, 2025

    40 Weatherbee Dr, Westwood, MA 02090

    • 4 Beds
    • 3 Baths
    • 2,563 Sq Ft
    • Built 1976

    Last Sold Summary

    • 3% Below List Price
    • $464/SF
    • 207 Days On Market

    Current Estimated Value $1,234,455

    Last Listing Agent Anna Federico Bel Air Properties

    40 Weatherbee Dr, Westwood, MA 02090
    • /42

      Est $1,602,180

      Not Listed For Sale

      121 Magnolia Dr, Westwood, MA 02090

      • 4 Beds
      • 2.5 Baths
      • 4,241 Sq Ft
      • Built 1968
      121 Magnolia Dr, Westwood, MA 02090

      Last Sold Summary

      • 2 Days On Market

  • /42

    $1,895,000

    $204K PRICE DROP
    • 4 Beds
    • 6 Baths
    • 5,263 Sq Ft

    10 Peartree Dr, Westwood, MA 02090

    Gorgeous, spacious colonial set on an acre in one of Westwood’s most coveted, quiet, picturesque neighborhoods. Main level offers open kitchen, dining and family room plus formal living room with fireplace. Family room is a true showstopper with soaring ceilings and exceptional natural light. Main-level makes entertaining easy w/ wet bar and seamless indoor-outdoor flow to a large patio, hot tub,

    Michael Tinsley Longwood Residential, LLC

    10 Peartree Dr, Westwood, MA 02090
  • /38

    $1,150,000

    Sold May 29, 2026

    829 Gay St, Westwood, MA 02090

    • 4 Beds
    • 2 Baths
    • 2,360 Sq Ft
    • Built 1953

    Last Sold Summary

    • $487/SF
    • 7 Days On Market

    Current Estimated Value $1,122,351

    Last Listing Agent Denise Connell Donahue Real Estate Co.

    829 Gay St, Westwood, MA 02090
    • /35

      Est $1,007,378

      Not Listed For Sale

      51 Saxon Rd, Westwood, MA 02090

      • 3 Beds
      • 2.5 Baths
      • 1,786 Sq Ft
      • Built 1966
      51 Saxon Rd, Westwood, MA 02090

      Last Sold Summary

      • 1 Day On Market

  • /27

    $7,250,000

    • 6 Beds
    • 7.5 Baths
    • 10,765 Sq Ft

    111 Summer St, Westwood, MA 02090

    Set on four beautifully landscaped acres in one of Westwood’s most desirable neighborhoods, this exceptional custom shingle-style residence offers over 10,000 square feet of thoughtfully designed living space. Built in 2016 and designed by acclaimed architect Christopher Hall, the home seamlessly blends architectural sophistication with everyday functionality. The open floor plan features a

    The Shulkin Wilk Group Compass

    111 Summer St, Westwood, MA 02090
  • /2

    $4,300,000

    Sold Jun 19, 2026

    77 Fox Hill St, Westwood, MA 02090

    • 5 Beds
    • 6.5 Baths
    • 7,200 Sq Ft
    • Built 2026

    Last Sold Summary

    • 6% Below List Price
    • $597/SF
    • 1 Day On Market

    Current Estimated Value $1,252,118

    Last Listing Agent Roula Gallis Bakis Artemis Realty

    77 Fox Hill St, Westwood, MA 02090
    • /37

      Est $1,527,546

      Not Listed For Sale

      31 Magnolia Dr, Westwood, MA 02090

      • 3 Beds
      • 3 Baths
      • 3,847 Sq Ft
      • Built 1968
      31 Magnolia Dr, Westwood, MA 02090

      Last Sold Summary

      • 14 Days On Market

  • /42

    $1,399,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,730 Sq Ft

    42 Birchtree Dr, Westwood, MA 02090

    Beautifully maintained and updated 4-bed, 2.5-bath Colonial, on picturesque Birchtree Dr., offers a serene wooded backdrop and layout designed for entertaining and every day life. Hardwood flooring extends throughout the home. Spacious living/dining room with traditional fireplace is adjacent to home office serving as a quiet workspace. Central kitchen appointed with custom cabinetry, quartz and

    The Jowdy Group RE/MAX Distinct Advantage

    42 Birchtree Dr, Westwood, MA 02090
  • /38

    $960,000

    Sold Apr 01, 2026

    21 Birch St, Westwood, MA 02090

    • 4 Beds
    • 2 Baths
    • 2,235 Sq Ft
    • Built 1952

    Last Sold Summary

    • 1% Below List Price
    • $430/SF
    • 11 Days On Market

    Current Estimated Value $953,883

    Last Listing Agent Michael Tinsley Longwood Residential, LLC

    21 Birch St, Westwood, MA 02090
    • /19

      Est $1,364,646

      Not Listed For Sale

      58 Alder Rd, Westwood, MA 02090

      • 4 Beds
      • 3 Baths
      • 3,085 Sq Ft
      • Built 1963
      58 Alder Rd, Westwood, MA 02090

      Last Sold Summary

      • 5 Days On Market

  • /42

    $1,449,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,779 Sq Ft

    37 Salisbury Dr, Westwood, MA 02090

    Beautifully maintained 4 bedroom Cape set on a meticulously landscaped lot in one of Westwood’s most sought after neighborhoods. Light-filled and inviting throughout, this charming home offers the perfect blend of comfort, character, & everyday functionality. Stunning kitchen features marble countertops & direct access to a patio, creating seamless indoor/outdoor living. Thoughtfully designed

    The Atwood Scannell Team Dover Country Properties Inc.

    37 Salisbury Dr, Westwood, MA 02090
  • /40

    $1,050,000

    Sold May 22, 2026

    60 Warwick Dr, Westwood, MA 02090

    • 3 Beds
    • 2.5 Baths
    • 1,461 Sq Ft
    • Built 1941

    Last Sold Summary

    • 3% Below List Price
    • $719/SF
    • 9 Days On Market

    Current Estimated Value $1,088,509

    Last Listing Agent Sam Zhu Keller Williams Realty

    60 Warwick Dr, Westwood, MA 02090
    • /36

      Est $1,250,086

      Not Listed For Sale

      105 Tamarack Rd, Westwood, MA 02090

      • 4 Beds
      • 3.5 Baths
      • 3,200 Sq Ft
      • Built 1966
      105 Tamarack Rd, Westwood, MA 02090

      Last Sold Summary

      • 44 Days On Market

  • /42

    $2,049,000

    Pending
    • 5 Beds
    • 5 Baths
    • 3,574 Sq Ft

    243 Weatherbee Dr, Westwood, MA 02090

    Your opportunity awaits for this first for sale offering of this glamorous colonial in the highly coveted Weatherbee Estates. This well-appointed home emits a great atmosphere, especially for entertaining and large gatherings. This home boasts an open floor plan of very sizable rooms, 4 bedrooms on the upper floor, high ceilings, hardwood floors, and plenty of natural lighting. The lower level is

    Anna Federico Bel Air Properties

    243 Weatherbee Dr, Westwood, MA 02090
  • /15

    $1,395,000

    Sold Oct 31, 2025

    300 Nahatan St, Westwood, MA 02090

    • Land
    • 1.84 Acres
    • $758,152 per Acre

    Last Sold Summary

    • 7% Below List Price
    • 60 Days On Market

    Current Estimated Value $1,476,612

    Last Listing Agent Barbara Shea Shea Realty Group

    300 Nahatan St, Westwood, MA 02090
    • /41

      Est $1,378,237

      Not Listed For Sale

      48 Tamarack Rd, Westwood, MA 02090

      • 4 Beds
      • 4 Baths
      • 2,656 Sq Ft
      • Built 1965
      48 Tamarack Rd, Westwood, MA 02090

      Last Sold Summary

      • 3 Days On Market

  • /34

    $2,250,000

    • 5 Beds
    • 4.5 Baths
    • 4,387 Sq Ft

    583 Gay St, Westwood, MA 02090

    Welcome to this spacious and inviting 3-bedroom in the desirable area of Westwood. 583 Gay St is a sun-filled home with over 3+ acres of privacy yet minutes to Islington Center, Rt 128 and Legacy Place. The main home boasts ample living space, including a living room, a generously sized modern kitchen with updated appliances, an office and 3 generous sized bedrooms. The property also features a

    The Shulkin Wilk Group Compass

    583 Gay St, Westwood, MA 02090
  • /40

    $875,000

    Sold Jun 26, 2026

    53 Dean St, Westwood, MA 02090

    • 4 Beds
    • 1.5 Baths
    • 1,440 Sq Ft
    • Built 1922

    Last Sold Summary

    • 8% Below List Price
    • $608/SF
    • 45 Days On Market

    Current Estimated Value $812,711

    Last Listing Agent Ronald Oliveira RE/MAX Vantage

    53 Dean St, Westwood, MA 02090
    • /42

      Est $1,992,143

      Not Listed For Sale

      12 Pettees Pond Ln, Westwood, MA 02090

      • 4 Beds
      • 3.5 Baths
      • 4,548 Sq Ft
      • Built 1997
      12 Pettees Pond Ln, Westwood, MA 02090

      Last Sold Summary

      • 3 Days On Market

  • /15

    $1,415,000

    $85K PRICE DROP Pending
    • 2 Beds
    • 3 Baths
    • 1,989 Sq Ft

    69 Abbey Rd Unit 69, Westwood, MA 02090

    69 Abbey Road offers the freedom to simply close the door and go. The main level flows effortlessly — sun-drenched living room with fireplace and hardwood floors, chef's kitchen with entertainer's island, bright dining area, primary suite, second full bath, office/den, and laundry. Everything you need, all on one floor.Upstairs, guests enjoy their own private retreat: bedroom, full bath, and loft

    Brooke Brown Coldwell Banker Realty - Westwood

    69 Abbey Rd Unit 69, Westwood, MA 02090
  • /4

    $1,300,000

    Sold Apr 02, 2026

    11 Stonegate Ln, Westwood, MA 02090

    • Land
    • 40,510 Sq Ft
    • $1,397,849 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 34 Days On Market

    Last Listing Agent Michael Viano Coldwell Banker Realty - Westwood

    11 Stonegate Ln, Westwood, MA 02090
    • /30

      Est $1,549,323

      Not Listed For Sale

      23 Whitney Ave, Westwood, MA 02090

      • 4 Beds
      • 3.5 Baths
      • 4,488 Sq Ft
      • Built 1996
      23 Whitney Ave, Westwood, MA 02090

      Last Sold Summary

      • 37 Days On Market

  • /21

    $850,000

    Open Sun 11:30AM - 1PM
    • 5 Beds
    • 2 Baths
    • 2,000 Sq Ft

    12 Westwood Terrace, Westwood, MA 02090

    Two buyers with cold feet. Now is your chance! Versatile 4-5 bedroom home w/2 full baths in a very desirable location with approx. 2000 sq. ft. of flexible living space. Two level living gives the home a larger than expected feel making it easy to adapt to a wide range of needs including multi-generational occupancy. On almost an acre the partially fenced, wooded property dotted with mature trees

    Roberta Hershon LAER Realty Partners

    12 Westwood Terrace, Westwood, MA 02090
  • /29

    $1,200,000

    Sold May 22, 2026

    17 June St, Westwood, MA 02090

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Built 1946

    Last Sold Summary

    • 4% Above List Price
    • $781/SF
    • 3 Days On Market

    Current Estimated Value $1,028,961

    Last Listing Agent Stacey Eliades Start Realty, LLC

    17 June St, Westwood, MA 02090
    • /33

      Est $1,583,793

      Not Listed For Sale

      33 Whitney Ave, Westwood, MA 02090

      • 4 Beds
      • 2.5 Baths
      • 2,535 Sq Ft
      • Built 1996
      33 Whitney Ave, Westwood, MA 02090

      Last Sold Summary

      • 1 Day On Market

  • /38

    $7,750,000

    $240K PRICE DROP
    • 8 Beds
    • 12 Baths
    • 17,175 Sq Ft

    18 Longmeadow Dr, Westwood, MA 02090

    Located in the highly sought-after Stevens Farm neighborhood of Westwood, this gated estate is set on 3.48 acres of beautifully landscaped grounds and was designed by noted architect Patrick Ahearn. The foyer, with its dramatic three-story atrium, leads to French doors opening on a 70’ terrace overlooking a spectacular pool and cabana. Formal living and dining rooms flow seamlessly off the

    John Boyle LandVest, Inc.

    18 Longmeadow Dr, Westwood, MA 02090

Showing Results 41 - 80, Page 2 of 18

How to Buy a Home How to Finance a Home How to Sell a Home