5,482

Westwood, MA Homes

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  • /41

    $949,000

    Open Sun 2PM - 3:30PM
    • 4 Beds
    • 2 Baths
    • 1,840 Sq Ft

    857 Gay St, Westwood, MA 02090

    Welcome to this beautifully updated, sun-drenched Cape in a highly sought-after Westwood neighborhood! The inviting main level features a seamless flow, anchored by an updated kitchen with a bright breakfast area. Entertain with ease in the formal dining room, or relax in the living room highlighted by a cozy wood-burning fireplace. Two versatile first-floor bedrooms and a full bath offer

    Agent Photo

    Alina Wang

    Coldwell Banker Realty - Lexington

    857 Gay St, Westwood, MA 02090
  • /50

    Starting at $2,436

    Total Monthly Price

    • 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

    21 Westwood Glen Rd, Westwood, MA 02090
  • /34

    $920,000

    Sold Sep 11, 2026

    58 Lyons Dr, Westwood, MA 02090

    • 4 Beds
    • 2 Baths
    • 1,903 Sq Ft
    • Built 1966

    Last Sold Summary

    • 1% Below List Price
    • $483/SF
    • 6 Days On Market

    Current Estimated Value $1,128,638

    Last Listing Agent Jessica Hancock Coldwell Banker Realty - Westwood

    58 Lyons Dr, Westwood, MA 02090
    • /38

      Est $1,252,686

      Not Listed For Sale

      18 Edgewood Rd, Westwood, MA 02090

      • 5 Beds
      • 3 Baths
      • 3,171 Sq Ft
      • Built 1950
      18 Edgewood Rd, Westwood, MA 02090

      Last Sold Summary

      • 82 Days On Market

      Last Listing Agent Tania Rooney Coldwell Banker Realty - Westwood

  • /40

    $6,950,000

    $550K PRICE DROP
    • 5 Beds
    • 7 Baths
    • 8,033 Sq Ft

    26 Longmeadow Dr, Westwood, MA 02090

    Nestled on 7.4 private acres abutting Hale Reservation, this recently renovated 8,000+ SF home blends luxury, comfort, and exceptional outdoor living in one of Westwood’s most sought-after neighborhoods. Thoughtfully designed for both entertaining and everyday living, the home offers 5 bedrooms, all with ensuite baths, plus 3 additional half baths. Sunlit interiors include a grand foyer, elegant

    Donna Scott Group Coldwell Banker Realty - Wellesley

    26 Longmeadow Dr, Westwood, MA 02090
  • /50

    Starting at $2,847

    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 commuter's 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

    Gables University Station

    85-100 University Ave, Westwood, MA 02090
  • /35

    $1,955,000

    Sold Jun 26, 2026

    55 Rockmeadow Rd, Westwood, MA 02090

    • 5 Beds
    • 6 Baths
    • 4,863 Sq Ft
    • Built 1947

    Last Sold Summary

    • 9% Above List Price
    • $402/SF
    • 2 Days On Market

    Current Estimated Value $1,923,230

    Last Listing Agent Legacy Group Coldwell Banker Realty - Westwood

    55 Rockmeadow Rd, Westwood, MA 02090
    • /29

      Est $1,659,527

      Not Listed For Sale

      124 Phillips Brooks Rd, Westwood, MA 02090

      • 5 Beds
      • 2.5 Baths
      • 3,280 Sq Ft
      • Built 1959
      124 Phillips Brooks Rd, Westwood, MA 02090

      Last Sold Summary

      • 26 Days On Market

      Last Listing Agent Tom Aaron Coldwell Banker Realty - Wellesley

  • /22

    $3,600,000

    Pending
    • 7 Beds
    • 4.5 Baths
    • 4,241 Sq Ft

    272 Fox Hill St, Westwood, MA 02090

    Built in 1850, this residence is a classic example of mid-19th-century New England architecture. Set on 8.93 potentially subdividable acres on Westwood's iconic Fox Hill Street, it is rich in historic character. It offers 4,241sf of living area and features hardwood floors, generously sized windows, multiple fireplaces, and built-in cabinetry. The entry foyer opens to a music room, living room,

    John Boyle LandVest, Inc.

    272 Fox Hill St, Westwood, MA 02090
  • /19

    $4,450 Per Month

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft
    • House for Rent

    43 Deerfield Ave, Westwood, MA 02090

    RARE WESTWOOD SINGLE-FAMILY | NO BROKER FEEFLEXIBLE MOVE-IN BETWEEN 9/15 AND 10/15A rare opportunity to rent a single-family home in Westwood, where homes like this rarely become available. Located on a quiet, sidewalk-lined street, this well-maintained split-level home offers approximately 2,000 square feet of flexible living space with three bedrooms, two full bathrooms,

    43 Deerfield Ave, Westwood, MA 02090
  • /42

    $1,110,000

    Sold Jul 31, 2026

    1689 High St, Westwood, MA 02090

    • 4 Beds
    • 2 Baths
    • 2,361 Sq Ft
    • Built 1790

    Last Sold Summary

    • 12% Above List Price
    • $470/SF
    • 3 Days On Market

    Current Estimated Value $1,061,922

    Last Listing Agent Elena Price Coldwell Banker Realty - Westwood

    1689 High St, Westwood, MA 02090
    • /34

      Est $1,373,958

      Not Listed For Sale

      186 Conant Rd, Westwood, MA 02090

      • 4 Beds
      • 2.5 Baths
      • 2,273 Sq Ft
      • Built 1965
      186 Conant Rd, Westwood, MA 02090

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Barbara Shea Shea Realty Group

  • /41

    $3,490,000

    $505K PRICE DROP
    • 5 Beds
    • 8 Baths
    • 9,286 Sq Ft

    9 Stonegate Dr, Westwood, MA 02090

    SPECTACULAR ESTATE PROPERTY in luxury Westwood neighborhood ! Built in 2004 the first owner redid the interior space over 5 years with the finest custom millwork & luxury finishes coupled with exquisitely landscaped private grounds with pool, 2 spas, waterfall with grotto, outdoor patio with stone oven and a heated guest cabin thoughtfully located amidst hilltop gardens in a premier Westwood

    Michael Viano Coldwell Banker Realty - Westwood

    9 Stonegate Dr, Westwood, MA 02090
  • /12

    $3,700 Plus Fees

    • 3 Beds
    • 1.5 Baths
    • Condo for Rent

    21 Grafton Ave Unit A, Westwood, MA 02090

    Property Id: 2863738 Welcome home to this unbeatable 3 bed 1.5 bath, recently renovated unit in the highly sought after Islington station of Westwood. This unit truly encompasses it all !!!!! From fresh paint, oversized rooms, bonus half bath, renovated fully applianced eat- in kitchen with granite countertops and Stainless steel appliances, breathtaking sunroom, Gas heat/ cooking, 2

    21 Grafton Ave Unit A, 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 $1,051,427

    Last Listing Agent Theresa David Gibson Sotheby's International Realty

    886 Gay St, Westwood, MA 02090
    • /42

      Est $2,063,816

      Not Listed For Sale

      53 Thompson Ave, Westwood, MA 02090

      • 4 Beds
      • 3.5 Baths
      • 4,300 Sq Ft
      • Built 2013
      53 Thompson Ave, Westwood, MA 02090

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Ellen McGillivray Coldwell Banker Realty - Westwood

  • /23

    $555,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 809 Sq Ft

    407 Washington St Unit 2, Westwood, MA 02090

    Imagine stepping out your front door and into the vibrant pulse of Islington Center morning coffee at the corner caf , fresh groceries at Roche Bros, a quick train ride into Boston, all before noon. This isn't just a condo. It's a lifestyle upgrade. Completely built out in 2022, every surface is new, every system is modern, and every detail was chosen for effortless living. No projects. No

    Gabe Francis Lenox Realty Group

    407 Washington St Unit 2, Westwood, MA 02090
  • /13

    $5,200 Per Month

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    99 Porter St, Westwood, MA 02090

    Located in a great area in Westwood close to University Ave., Legacy Place 128 great yard off street parking to car garage very spacious

    99 Porter 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 $2,134,567

    Last Listing Agent Ralph Smith Compass

    122 Smith Dr, 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

      • 1 Day On Market

      Last Listing Agent Elena Price Coldwell Banker Realty - Westwood

  • /40

    $1,599,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 4,568 Sq Ft

    25 Clearwater Dr, Westwood, MA 02090

    From the moment you enter, the generous proportions and inviting character of this beautifully updated Cape set it apart. Meticulously maintained and offering over 3,200 square feet of above-grade living and over 1300 below grade, the home features exceptionally large rooms throughout and the rare flexibility of primary suites on both levels, creating a home that feels substantial yet warm and

    Lori Seavey Keller Williams Elite

    25 Clearwater Dr, Westwood, MA 02090
  • /22

    $4,800 Per Month

    • 4 Beds
    • 2 Baths
    • 2,200 Sq Ft
    • House for Rent

    97 Deerfield Ave, Westwood, MA 02090

    This charming cape-style house is bigger than it looks! Generous room sizes in the living area, including a fireplaced living room, formal dining room, recently updated kitchen with eating area and access to the back yard plus two bedrooms,a full bath, an office and an unheated sun room on the main level. Second floor has two more bedrooms and a full bath plus a laundry room and bonus room off of

    Barbara Shea Shea Realty Group

    97 Deerfield Ave, Westwood, MA 02090
  • /24

    $2,325,000

    Sold Jul 20, 2026

    298 Summer St, Westwood, MA 02090

    • 5 Beds
    • 4.5 Baths
    • 4,700 Sq Ft
    • Built 2025

    Last Sold Summary

    • 15% Below List Price
    • $495/SF
    • 791 Days On Market

    Current Estimated Value $2,341,070

    Last Listing Agent John Boyle LandVest, Inc.

    298 Summer St, Westwood, MA 02090
    • /35

      Est $871,320

      Not Listed For Sale

      51 Reynolds Farm Way Unit 51, Westwood, MA 02090

      • 2 Beds
      • 4 Baths
      • 2,582 Sq Ft
      • Built 2012
      51 Reynolds Farm Way Unit 51, Westwood, MA 02090

      Last Sold Summary

      • 15 Days On Market

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

  • /33

    $925,000

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft

    72 Sexton Ave, Westwood, MA 02090

    Welcome to 72 Sexton Ave, a much-loved 4-bedroom, 2-bath Cape that has been a cherished family home for many years. Offered as an estate sale, this property presents a wonderful opportunity for its next owner to bring fresh ideas and a new vision to a home filled with years of memories. The classic Cape-style layout offers four bedrooms and two full baths, providing flexibility for family,

    Sheila Moylan Coldwell Banker Realty - Westwood

    72 Sexton Ave, Westwood, MA 02090
  • /20

    $3,500 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft
    • Apartment for Rent

    21 Grafton Ave Unit 21, Westwood, MA 02090

    This beautifully well-maintained home on the second floor in a two-family house in Westwood will be available on 8/30/2026. The home features three bedrooms and 1.5 updated bathrooms. It is in a great school district with good accessibility to the train station, bus stop, and highway systems. Also, the home is within walking distance of the train station, shops, restaurants, a playground, a

    Grace Li PlanSmart Realty LLC

    21 Grafton Ave Unit 21, Westwood, MA 02090
  • /42

    $1,500,000

    Sold Jun 12, 2026

    20 Gay St, Westwood, MA 02090

    • 4 Beds
    • 2.5 Baths
    • 3,952 Sq Ft
    • Built 1935

    Last Sold Summary

    • $380/SF
    • 4 Days On Market

    Current Estimated Value $1,488,793

    Last Listing Agent The Shulkin Wilk Group Compass

    20 Gay St, Westwood, MA 02090
    • /16

      Est $2,029,475

      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

      Last Listing Agent Ruchi Misra Keller Williams Realty Boston Northwest

  • /42

    $4,495,000

    Pending
    • 6 Beds
    • 6.5 Baths
    • 8,827 Sq Ft

    20 Longmeadow Dr, Westwood, MA 02090

    Your family's everything dream home is already built for you with both elegance and warmth as soon as you step in. Light-filled rooms throughout, featuring window seating both in the kitchen's separate eating area and in the hexagonal library. Floor to vaulted ceiling windows that flank the grand stone and brick fireplace in the Great Room and carry you to the gourmet kitchen with quartz

    Peter Cwieka Media Realty Group Inc.

    20 Longmeadow Dr, Westwood, MA 02090
  • /14

    $4,200 Per Month

    • 4 Beds
    • 2 Baths
    • 1,657 Sq Ft
    • House for Rent

    544 High St, Westwood, MA 02090

    This ranch-style home is minutes from downtown Westwood, the Westwood Library, restaurants, and highway access. With four bedrooms and two bathrooms across 1,657 square feet, it offers comfortable living spaces for everyday life and entertaining. Multiple living areas provide flexibility for a home office, and an enclosed porch adds another place to relax. Features include hardwood floors, new

    Mona Chahine Coldwell Banker Realty - Westwood

    544 High 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 $1,792,951

    Last Listing Agent Anna Federico Bel Air Properties

    139 Porter St, Westwood, MA 02090
    • /42

      Est $1,227,929

      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

      Last Listing Agent Francis Curran Coldwell Banker Realty - Westwood

  • /35

    $1,175,000

    Open Sun 11:30AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,885 Sq Ft

    13 Millbrook Rd, Westwood, MA 02090

    Tucked away in a premier neighborhood, just a stone’s throw from the local elementary school and fields, this Royal Barry Wills-style Cape represents a rare opportunity to enter the Westwood market at an exceptional price point. Set on nearly an acre of picturesque land along the banks of Mill Brook. While the home retains its timeless architectural character, the current owners have thoughtfully

    The Shulkin Wilk Group Compass

    13 Millbrook Rd, Westwood, MA 02090
  • /29

    $4,800 Per Month

    • 4 Beds
    • 2 Baths
    • 2,034 Sq Ft
    • House for Rent

    92 Hawthorn St, Westwood, MA 02090

    Charming home located in the top-rated Westwood school district. It offers outstanding convenience near the newly redeveloped Islington Center, commuter rail, Legacy Place, University Station, shops, restaurants, and major routes. The flexible layout is ideal for both everyday living and entertaining. The first floor includes two bedrooms, a full bathroom, a living room, a kitchen, and a

    Grace Li PlanSmart Realty LLC

    92 Hawthorn 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 $1,169,054

    Last Listing Agent Elena Price Coldwell Banker Realty - Westwood

    20 Lakeshore Dr, Westwood, MA 02090
    • /39

      Est $1,234,966

      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

      Last Listing Agent Elena Price Coldwell Banker Realty - Westwood

  • /2

    $1,395,000

    • Land
    • 4 Acres
    • $348,750 per Acre

    385 Sandy Valley, Westwood, MA 02090

    Rare opportunity on Sandy Valley Road, one of Westwood’s most distinctive estate settings. This 4-acre parcel, now identified as 385 Sandy Valley Road, offers privacy, natural surroundings and the potential for one or possibly two building lots in an area known for substantial homes and exceptional land. Development is contingent upon securing all required approvals, including roadway upgrades,

    John Boyle LandVest, Inc.

    385 Sandy Valley, Westwood, MA 02090
  • /28

    $850,000

    Sold Dec 30, 2025

    90 Blueberry Ln, Westwood, MA 02090

    • 3 Beds
    • 2 Baths
    • 1,520 Sq Ft
    • Built 1974

    Last Sold Summary

    • 6% Above List Price
    • $559/SF
    • 2 Days On Market

    Current Estimated Value $906,914

    Last Listing Agent Jim Gibbons RE/MAX Real Estate Center

    90 Blueberry Ln, Westwood, MA 02090
    • /42

      Est $1,592,116

      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

      Last Listing Agent Sheila Moylan Coldwell Banker Realty - Westwood

  • /40

    $2,295,000

    $70K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,908 Sq Ft

    54 Meadowbrook Rd, Westwood, MA 02090

    Prime location on culdesac - Two year young custom built contemporary style home with thoughtful detail and design boasts all you would expect with high ceilings, white oak floors, oversize windows, spacious bright rooms and comfortable living space. Welcome your guests onto the wide front porch and into the large open entry foyer. There is a front sitting room, office space and separate

    Elena Price Coldwell Banker Realty - Westwood

    54 Meadowbrook Rd, Westwood, MA 02090

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$1,195,000
Median Single Family Sale Price
$1,300,000
Median Townhouse Sale Price
$11,000,000
Median 2 Bedroom Sale Price
$832,500
Average Price Per Sq Ft
$527
Number of Homes for Sale
5,482
Last 12 months Home Sales
126
Months of Supply
2.60
Median List Price
$1,249,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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