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Westwood, MA Homes for Sale with Pool

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  • /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
  • /25

    $945,000

    Open Sat 11:30AM - 1PM
    • 4 Beds
    • 2 Baths
    • 1,962 Sq Ft

    101 Lakeshore Dr, Westwood, MA 02090

    Opportunity to purchase this picture perfect move in ready home with a nice usable back yard abutting conservation with a view of the pond. Located in a popular neighborhood there have been many updates over the years to maintain the home offering living space on three levels. Upon entering there is a fireplace family room open to the dining room with built in cabinet. The kitchen with some

    Elena Price Coldwell Banker Realty - Westwood

    101 Lakeshore Dr, Westwood, MA 02090
  • /40

    $2,365,000

    • 4 Beds
    • 4.5 Baths
    • 4,908 Sq Ft

    54 Meadowbrook Rd, Westwood, MA 02090

    Two year young custom built contemporary style home with thoughtful detail and design boasting everything you would expect. 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 expansive dining room offering

    Elena Price Coldwell Banker Realty - Westwood

    54 Meadowbrook Rd, Westwood, MA 02090
  • /32

    $4,000,000

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

    157 Grove St, Westwood, MA 02090

    A private estate spanning 11 spectacular acres, this distinguished 1912 residence offers timeless character and exceptional privacy in one of the Boston area's most coveted settings. The five-BR home features 4,500+ square feet of beautifully maintained living space blending classic architectural details with modern comfort. Grand living and dining rooms, a sun-drenched conservatory, and an

    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
  • /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
  • /33

    $1,199,000

    Open Sun 11:30AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,472 Sq Ft

    45 Blueberry Ln, Westwood, MA 02090

    Welcome to 45 Blueberry Lane, a timeless Colonial set on a picturesque 1.08-acre lot in one of Westwood's most sought-after neighborhoods. Tucked away on a quiet side street, this home is a peaceful retreat, offering a rare combination of privacy, luxury, and convenience, just minutes from top-rated schools, shopping, parks, commuter rail, and major highways. From the moment you arrive, you'll

    DeWolfe Group Gibson Sotheby's International Realty

    45 Blueberry Ln, 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
  • /8

    $1,195,000

    • 5 Beds
    • 2.5 Baths
    • 2,907 Sq Ft

    355 High St, Westwood, MA 02090

    Exceptional two-acre property offers the perfect balance of privacy and convenience, with easy access to the town center, major commuter routes in premier MetroWest community of Westwood. Built in 1929, this classic Colonial showcases timeless architectural character, featuring high ceilings, oversized windows and french doors providing an abundance of natural light, and hardwood floors

    Jane Wemyss Compass

    355 High St, 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
$1,202,500
Median Single Family Sale Price
$1,300,000
Median 2 Bedroom Sale Price
$825,000
Average Price Per Sq Ft
$529
Number of Homes for Sale
21
Last 12 months Home Sales
122
Months of Supply
2.10
Median List Price
$1,249,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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