13

Westwood, MA Homes for Sale with Pool

Section Image
  • /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
  • /20

    $849,900

    $20K PRICE DROP
    • 5 Beds
    • 1.5 Baths
    • 1,419 Sq Ft

    290 East St, Westwood, MA 02090

    An inviting opportunity to own a slice of Westwood! Great condo alternative! Charming Cape-style home set on a private half-acre lot in desirable 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 ideal for today’s

    DeWolfe Group Gibson Sotheby's International Realty

    290 East St, Westwood, MA 02090
  • /41

    $3,490,000

    $505K PRICE DROP
    • 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
  • /42

    $4,495,000

    • 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /26

    $8,800,000

    $890K PRICE DROP
    • 7 Beds
    • 8 Baths
    • 12,762 Sq Ft

    401 Sandy Valley Rd, Westwood, MA 02090

    Set at the end of a long winding drive, this remarkable 16+ acre estate abuts more than 100 acres of conservation land, creating a rare sense of privacy and natural beauty. Suited for formal entertaining, intimate gatherings, and gracious family living, it includes a welcoming main entrance hall, a wonderful living room with an attached library, a spacious formal dining room with adjoining

    John Boyle LandVest, Inc.

    401 Sandy Valley Rd, Westwood, MA 02090
  • /39

    $1,398,000

    • 5 Beds
    • 2.5 Baths
    • 2,683 Sq Ft

    9 Wessex Dr, Westwood, MA 02090

    Beautifully updated meticulously maintained solar powered 4+BR/2BA expanded Cape w 2-car attached garage in Westwood’s sought-after in-town Center/Hartford St neighborhood. Enjoy a walk-to-town lifestyle w convenient access to top-rated schools, parks, Hale Reservation, commuter rail, shopping, dining, & University Station. This spacious home offers an updated kitchen with slider to the backyard,

    Lexi Crivon Coldwell Banker Realty - Boston

    9 Wessex Dr, Westwood, MA 02090
  • /38

    $5,495,000

    • 5 Beds
    • 7 Baths
    • 10,407 Sq Ft

    4 Wilson's Way, Dover, MA 02030

    Beyond stunning custom home! Over 11,000 sq ft of incredible living along with a private pond on 2.36 acres. High ceilings, open floor plan & filled with sunlight. Designer kitchen w/ huge walk-in pantry, oversized island, gorgeous thick marble counters. Breakfast room leads to family room w/ an entire bank of windows overlooking the yard. Unique walk-in wine storage. Formal living w/ fireplace &

    Melissa Dailey Coldwell Banker Realty - Wellesley

    4 Wilson's Way, Dover, MA 02030

Home Price Trends

Median Sale Price
$1,195,000
Median Single Family Sale Price
$1,255,000
Median Townhouse Sale Price
$870,000
Median 2 Bedroom Sale Price
$825,000
Median 1 Bedroom Sale Price
$585,000
Average Price Per Sq Ft
$523
Number of Homes for Sale
23
Last 12 months Home Sales
130
Months of Supply
2.10
Median List Price
$1,229,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
How to Buy a Home How to Finance a Home How to Sell a Home