5,482

Westwood, MA Homes

Section Image
  • /37

    $2,599,000

    • 5 Beds
    • 5.5 Baths
    • 4,600 Sq Ft

    216 Oak St, Westwood, MA 02090

    Exceptional 2-year-young custom Colonial with 3-car garage, set on ~1 acre of landscaped grounds, featuring 5 spacious bedrooms, each with its own ensuite bath, blending modern luxury, thoughtful design, and everyday comfort. A stunning chef’s kitchen offers Miele and Gaggenau appliances, two dishwashers, quartz countertops, custom cabinetry, and a butler’s pantry for effortless entertaining. A

    Anna Federico Bel Air Properties

    216 Oak St, Westwood, MA 02090
  • /50

    Starting at $2,186 Plus Fees

    • 1 - 2 Beds

    21 Westwood Glen Rd, Westwood, MA 02090

    Located in the quaint town of Westwood, MA, Westwood Glen Commons offers renovated apartments for adults age 55+. Our mature landscaped grounds and friendly management team will welcome you home. Choose from 1 and 2 bedrooms with updated plank flooring, granite counters, stainless steel appliances and in home laundry. Residents enjoy our grill/courtyard area, social activities, dog park, bocce

    Westwood Glen Commons

    (781) 694-6342

    21 Westwood Glen Rd, Westwood, MA 02090
  • /42

    $3,000,000 Sold Jun 18, 2025

    134 High Rock Ln, Westwood, MA 02090

    • 4 Beds
    • 5.5 Baths
    • 5,595 Sq Ft
    • Built 2016

    Last Sold Summary

    • $536/SF
    • 11 Days On Market

    Current Estimated Value $3,013,827

    Last Listing Agent Barbara Shea Shea Realty Group

    134 High Rock Ln, Westwood, MA 02090
    • /39

      Est $877,608 Not Listed For Sale

      138 Mill St, Westwood, MA 02090

      • 3 Beds
      • 1.5 Baths
      • 1,516 Sq Ft
      • Built 1818
      138 Mill St, Westwood, MA 02090

      Last Sold Summary

      • 6% Above List Price
      • $544/SF
      • 6 Days On Market
      • Last Sold Price $825,000
      • May 06, 2025

      Last Listing Agent Christina DiNardi Keller Williams Realty Boston-Metro | Back Bay

  • /24

    $2,495,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 4,700 Sq Ft

    298 Summer St, Westwood, MA 02090

    This sophisticated New England farmhouse is set on Westwood’s iconic Summer Street. Recently completed, it offers 4,700 square feet of living space that blends classic detail with tasteful contemporary design. The gourmet kitchen is a culinary enthusiast’s dream, featuring granite countertops and a substantial island ideal for both preparation and casual dining. It opens to a fireplaced living

    John Boyle LandVest, Inc.

    298 Summer St, Westwood, MA 02090
  • /50

    Starting at $2,379

    Total Monthly Price

    • 1 - 2 Beds

    85-100 University Ave, Westwood, MA 02090

    Gables University Station, situated along University Avenue at the junction of Route I-95/Route 128 MBTA/Amtrak station, is a prestigious rental community and commuters dream conveniently located adjacent to the Amtrak Station. Enjoy an array of lifestyle amenities and conveniences within walking distance to your Westwood community. At Gables Residential, we live by our mission of Taking Care of

    Gables University Station

    (339) 216-4709

    85-100 University Ave, Westwood, MA 02090
  • /42

    $1,495,000 Sold May 30, 2025

    55 Mayfair Dr, Westwood, MA 02090

    • 4 Beds
    • 3 Baths
    • 2,764 Sq Ft
    • Built 1939

    Last Sold Summary

    • $541/SF
    • 6 Days On Market

    Current Estimated Value $1,487,283

    Last Listing Agent Anne Fahy Coldwell Banker Realty - Canton

    55 Mayfair Dr, Westwood, MA 02090
    • /31

      Est $1,289,931 Not Listed For Sale

      106 Juniper Ridge Rd, Westwood, MA 02090

      • 4 Beds
      • 3.5 Baths
      • 3,329 Sq Ft
      • Built 1960
      106 Juniper Ridge Rd, Westwood, MA 02090

      Last Sold Summary

      • 7% Above List Price
      • $360/SF
      • 26 Days On Market
      • Last Sold Price $1,200,000
      • May 09, 2025

      Last Listing Agent Rich Dolabany Boston Heritage Realty, LLC

  • /41

    $3,490,000

    • 5 Beds
    • 8 Baths
    • 9,286 Sq Ft

    9 Stonegate Dr, Westwood, MA 02090

    NEW PRICE! Built in 2004 the first owner redid the interior space over 5 years w/ the finest custom millwork & luxury finishes coupled w/ exquisitely landscaped private grounds w/ pool, 2 spas, waterfall w/ grotto, outdoor patio w/ stone oven & a heated guest cabin thoughtfully located amidst hilltop gardens in a premier Westwood estate area. In addition to the gracious entry hall, formal dining

    Michael Viano Coldwell Banker Realty - Westwood

    9 Stonegate Dr, Westwood, MA 02090
  • /35

    Starting at $2,710 Plus Fees

    • 1 - 2 Beds

    5100-5419 Highland Glen Rd, Westwood, MA 02090

    Engage in the atmosphere of our 55+ active adult carefree community with cozy indoor and outdoor spaces. Spend quality time with neighbors, friends, and family alike at our spacious clubroom, curl up with a book in the library, or surf the web in the computer room. Connect with fellow residents during book club, game nights, and classes. You will feel at home at the Residences at Highland Glen.

    Residences at Highland Glen - 55+ Active Adult Community

    (774) 341-4515

    5100-5419 Highland Glen Rd, Westwood, MA 02090
  • /40

    $1,625,500 Sold Jul 16, 2025

    256 Burgess Ave, Westwood, MA 02090

    • 4 Beds
    • 3.5 Baths
    • 2,914 Sq Ft
    • Built 2001

    Last Sold Summary

    • 14% Above List Price
    • $558/SF
    • 5 Days On Market

    Current Estimated Value $1,570,620

    Last Listing Agent Tom Aaron Coldwell Banker Realty - Wellesley

    256 Burgess Ave, Westwood, MA 02090
    • /38

      Est $1,554,732 Not Listed For Sale

      48 Wessex Dr, Westwood, MA 02090

      • 4 Beds
      • 2.5 Baths
      • 2,528 Sq Ft
      • Built 1941
      48 Wessex Dr, Westwood, MA 02090

      Last Sold Summary

      • 5% Below List Price
      • $648/SF
      • 4 Days On Market
      • Last Sold Price $1,638,888
      • May 09, 2025

      Last Listing Agent Elena Price Coldwell Banker Realty - Westwood

  • /2

    $4,575,000 Pending

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

    77 Fox Hill St, Westwood, MA 02090

    Set on Westwood’s coveted Fox Hill, and a quick walk across the street to adored Farm Lane, this exceptional new construction home blends timeless elegance with modern luxury. Offering 5 bedrooms (potentially 6 on the 1st floor) with 6.5 baths, this home has been thoughtfully designed to check every box. A beautifully appointed chef’s kitchen with premium appliances, oversized pantry, and

    Roula Gallis Bakis Artemis Realty

    77 Fox Hill St, Westwood, MA 02090
  • /14

    $2,500 Per Month

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft
    • Apartment for Rent

    165 Grove St Unit B2, Westwood, MA 02090

    Nestled along one of Westwood's most scenic streets, discover the inviting and very private residence located at 165 Grove unit B2, offering a unique opportunity to experience comfortable living in a coveted location. Within this second floor unit, you find a thoughtfully designed open concept kitchen with new stainless steel appliances, a living room with vaulted ceilings and a spacious separate

    Legacy Group Coldwell Banker Realty - Westwood

    165 Grove St Unit B2, Westwood, MA 02090
  • /42

    $1,790,000 Sold Aug 29, 2025

    10 Gloucester Rd, Westwood, MA 02090

    • 5 Beds
    • 5 Baths
    • 4,644 Sq Ft
    • Built 2012

    Last Sold Summary

    • 6% Below List Price
    • $385/SF
    • 38 Days On Market

    Current Estimated Value $1,843,027

    Last Listing Agent Elena Price Coldwell Banker Realty - Westwood

    10 Gloucester Rd, Westwood, MA 02090
    • /29

      Not Listed For Sale

      409 Washington St Unit 2, Westwood, MA 02090

      • 2 Beds
      • 1 Bath
      • 818 Sq Ft
      • Built 1969
      409 Washington St Unit 2, Westwood, MA 02090

      Last Sold Summary

      • $642/SF
      • 1 Day On Market
      • Last Sold Price $525,000
      • Sep 27, 2023

      Last Listing Agent Virginia Bethoney Discover Properties

  • /42

    $1,995,000

    • 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
  • /7

    $1,890

    Total Monthly Price

    • Studio
    • 1 Bath
    • 725 Sq Ft
    • House for Rent

    122 Burgess Ave, Westwood, MA 02090

    Cozy & Private Basement Apartment – Perfect for Students or Professionals!Looking for a bright, peaceful, and beautifully finished space to call home while you study or work? This inviting 725 sq. ft. basement apartment in Westwood offers the perfect balance of comfort and convenience!Utilities included, no broker fee, pet-friendly, and flexible lease termsFeatures You'll

    122 Burgess Ave, Westwood, MA 02090
  • /39

    $1,491,000 Sold May 15, 2025

    356 Farm Ln, Westwood, MA 02090

    • 5 Beds
    • 3 Baths
    • 4,000 Sq Ft
    • Built 1958

    Last Sold Summary

    • 2% Below List Price
    • $373/SF
    • 6 Days On Market

    Current Estimated Value $1,587,432

    Last Listing Agent Roula Gallis Bakis Artemis Realty

    356 Farm Ln, Westwood, MA 02090
    • /16

      Est $1,976,459 Not Listed For Sale

      5 Fox Meadow Dr, Westwood, MA 02090

      5 Fox Meadow Dr, Westwood, MA 02090

      Last Sold Summary

      • 8% Above List Price
      • 129 Days On Market
      • Last Sold Price $1,825,000
      • Feb 16, 2024

      Last Listing Agent Ruchi Misra Keller Williams Realty Boston Northwest

  • /42

    $2,648,888

    • 5 Beds
    • 4.5 Baths
    • 4,600 Sq Ft

    39 Peartree Dr, Westwood, MA 02090

    Showstopping & thoughtfully renovated throughout, this standout home offers the perfect mix of clean design, high-end finishes & everyday functionality in one of the area’s most sought-after neighborhoods. The main level is bright, open, and versatile featuring a beautifully designed kitchen w/ oversized island, custom cabinetry & seamless flow into both the dining area & living spaces. A

    Laryssa Dias-DeSouza Laryssa Dias

    39 Peartree Dr, Westwood, MA 02090
  • /16

    $2,500 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    405 Washington St Unit 2, Westwood, MA 02090

    Great commuter location on bus line and close to multiple trains in the heart of Islington Center. This newly renovated property offers the perfect blend of comfort and convenience featuring 2 bedrooms, 1 bathroom, eat in kitchen and family room with small deck off back. Second floor unit with two parking spaces. Available now with a two year lease desired if possible. No pets and no smoking.

    Len Chiariello Coldwell Banker Realty - Westwood

    405 Washington St Unit 2, Westwood, MA 02090
  • /41

    $1,000,000 Sold Nov 20, 2025

    886 Gay St, Westwood, MA 02090

    • 4 Beds
    • 2.5 Baths
    • 2,284 Sq Ft
    • Built 1949

    Last Sold Summary

    • 9% Below List Price
    • $438/SF
    • 8 Days On Market

    Current Estimated Value $1,018,507

    Last Listing Agent Theresa David Gibson Sotheby's International Realty

    886 Gay St, Westwood, MA 02090
    • /42

      Est $1,185,641 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

      • 5% Above List Price
      • $482/SF
      • 6 Days On Market
      • Last Sold Price $1,128,668
      • Dec 04, 2024

      Last Listing Agent Francis Curran Coldwell Banker Realty - Westwood

  • /29

    $2,549,000 Pending

    • 5 Beds
    • 5.5 Baths
    • 5,402 Sq Ft

    48 Sunrise Rd, Westwood, MA 02090

    Beautifully crafted NEW CONSTRUCTION in Westwood MA, offers an open floor plan, generous rooms, and a thoughtful custom design. Light-filled chef’s kitchen w oversized island, custom cabinetry, high-end appliances, and large walk-in pantry, flowing seamlessly into integrated dining area and spacious family room w gas fireplace. Generous mudroom with half bath, and First-floor en-suite bedroom

    Roula Gallis Bakis Artemis Realty

    48 Sunrise Rd, Westwood, MA 02090
  • /23

    $4,450 Per Month

    • 2 Beds
    • 2 Baths
    • 1,480 Sq Ft
    • Condo for Rent

    120 University Ave Unit 2301, Westwood, MA 02090

    available from 7/1. The best "I style" floor plan corner unit in Westwood Place! You gonna fall in love with the stunning spacious 1480 sqft 2 bed 2 bath home! One outdoor parking and one garage parking included. This unit features an open eat-in granite kitchen, large living room w/private balcony, flex/dining room, spacious master suite w/walk-in closet, full bath with stall shower, second

    CardinalRE Group Hooli Homes Boston

    120 University Ave Unit 2301, Westwood, MA 02090
  • /35

    $950,000 Sold Jun 06, 2025

    51 Saxon Rd, Westwood, MA 02090

    • 3 Beds
    • 2.5 Baths
    • 1,786 Sq Ft
    • Built 1966

    Last Sold Summary

    • 6% Above List Price
    • $532/SF
    • 1 Day On Market

    Current Estimated Value $1,015,492

    Last Listing Agent Leslee Winston William Raveis R.E. & Home Services

    51 Saxon Rd, Westwood, MA 02090
    • /31

      Est $1,101,856 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

      • 16% Above List Price
      • $475/SF
      • 26 Days On Market
      • Last Sold Price $950,000
      • Jun 23, 2023

      Last Listing Agent Ann Wood Keller Williams Realty Boston South West

  • /32

    $7,500,000

    • 5 Beds
    • 7 Baths
    • 8,033 Sq Ft

    26 Longmeadow Dr, Westwood, MA 02090

    Nestled on over 7.4 acres abutting Hale Reservation, this stunning estate offers 8,000+ square feet of thoughtfully designed living space. Blending elegance with everyday comfort, this five-bedroom, four full bath, and three half-bath home provides rare privacy all within commuting distance of Boston. Set back from the road with a long private driveway, the property offers seclusion while being

    Donna Scott Group Coldwell Banker Realty - Wellesley

    26 Longmeadow Dr, Westwood, MA 02090
  • /35

    $870,000 Sold Jun 30, 2025

    51 Reynolds Farm Way Unit 51, Westwood, MA 02090

    • 2 Beds
    • 4 Baths
    • 2,582 Sq Ft
    • Built 2012

    Last Sold Summary

    • 2% Below List Price
    • $337/SF
    • 15 Days On Market

    Current Estimated Value $874,002

    Last Listing Agent Christina Perdiki-Lord Coldwell Banker Realty - Waltham

    51 Reynolds Farm Way Unit 51, Westwood, MA 02090
    • /41

      Est $1,944,832 Not Listed For Sale

      83 Winslow Rd, Westwood, MA 02090

      • 5 Beds
      • 6 Baths
      • 5,957 Sq Ft
      • Built 1993
      83 Winslow Rd, Westwood, MA 02090

      Last Sold Summary

      • 14% Above List Price
      • $285/SF
      • 4 Days On Market
      • Last Sold Price $1,700,000
      • Jun 08, 2023

      Last Listing Agent Kathy Murray Coldwell Banker Realty - Westwood

  • /42

    $1,495,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 3,952 Sq Ft

    20 Gay St, Westwood, MA 02090

    Welcome to 20 Gay St, an exceptional 4-bedroom home where understated charm meets refined luxury in the heart of Westwood. Rebuilt in 2009, this impeccably maintained home offers the quality, scale, & thoughtful design of newer construction in a close-to-everything location. Inside custom carpentry & curated finishes elevate every space. The spacious layout is designed for modern living,

    The Shulkin Wilk Group Compass

    20 Gay St, Westwood, MA 02090
  • /31

    $2,100,000 Sold Sep 30, 2025

    122 Smith Dr, Westwood, MA 02090

    • 5 Beds
    • 3.5 Baths
    • 3,508 Sq Ft
    • Built 2017

    Last Sold Summary

    • 5% Above List Price
    • $599/SF
    • 3 Days On Market

    Current Estimated Value $2,075,373

    Last Listing Agent Ralph Smith Compass

    122 Smith Dr, Westwood, MA 02090
    • /39

      Est $1,252,264 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

      • $525/SF
      • 6 Days On Market
      • Last Sold Price $1,250,000
      • Apr 16, 2025

      Last Listing Agent Elena Price Coldwell Banker Realty - Westwood

  • /20

    $870,000

    • 5 Beds
    • 1.5 Baths
    • 1,419 Sq Ft

    290 East St, Westwood, MA 02090

    An inviting opportunity to own a slice of Westwood heaven. Charming Cape-style home set on a private half-acre lot along East Street in sought-after Islington. A commuter’s dream just minutes to the train, major highways, Islington Village, Norfolk Country Club, and Downey Elementary, with sidewalks leading to all. This welcoming 5-bedroom home offers a flexible floor plan suited for today’s

    DeWolfe Group Gibson Sotheby's International Realty

    290 East St, Westwood, MA 02090
  • /16

    $1,350,000 Sold Oct 31, 2025

    139 Porter St, Westwood, MA 02090

    • 4 Beds
    • 3 Baths
    • 3,847 Sq Ft
    • Built 1978

    Last Sold Summary

    • 10% Below List Price
    • $351/SF
    • 69 Days On Market

    Current Estimated Value $1,775,256

    Last Listing Agent Anna Federico Bel Air Properties

    139 Porter St, Westwood, MA 02090
    • /42

      Est $1,618,369 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

      • 8% Above List Price
      • $354/SF
      • 2 Days On Market
      • Last Sold Price $1,500,000
      • Jan 14, 2025

      Last Listing Agent Sheila Moylan Coldwell Banker Realty - Westwood

  • /30

    $995,000 Pending

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

    70 Cobleigh St, Westwood, MA 02090

    Available for the first time in 44 years, this tastefully updated & proudly maintained Colonial offers 2,264± SF of living space & is set on a lovely 9,221± SF lot in a highly prized side street neighborhood in the reimagined village of Islington. The elegant first floor includes an entry hall, living room with fireplace, formal dining room with built-in china cabinet, eat-in kitchen with granite

    Tom Aaron Coldwell Banker Realty - Wellesley

    70 Cobleigh St, Westwood, MA 02090
  • /38

    $1,050,000 Sold Oct 31, 2025

    20 Lakeshore Dr, Westwood, MA 02090

    • 4 Beds
    • 4 Baths
    • 2,786 Sq Ft
    • Built 1974

    Last Sold Summary

    • 11% Above List Price
    • $377/SF
    • 4 Days On Market

    Current Estimated Value $1,042,498

    Last Listing Agent Elena Price Coldwell Banker Realty - Westwood

    20 Lakeshore Dr, Westwood, MA 02090
    • /37

      Est $1,537,107 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

      • 6% Above List Price
      • $377/SF
      • 14 Days On Market
      • Last Sold Price $1,450,000
      • Aug 06, 2024

      Last Listing Agent Britta Reissfelder Coldwell Banker Realty - Canton

Showing Results 1 - 40, Page 1 of 18

Home Trends in Westwood, MA

Housing Trends

Median Sale Price
$1,235,000
Median Single Family Sale Price
$1,267,500
Median Townhouse Sale Price
$870,000
Median 2 Bedroom Sale Price
$842,500
Median 1 Bedroom Sale Price
$553,500
Average Price Per Sq Ft
$523
Number of Homes for Sale
22
Last 12 months Home Sales
133
Months of Supply
2.00
Median List Price
$1,229,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
12%
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