Find your next home in Westwood, MA

Why Buy a Home in Westwood, MA

Westwood is one of the most sought-after towns on Boston's south side, known for its top-ranked schools, beautifully maintained neighborhoods, and exceptional quality of life. With a population that values community, conservation, and education, Westwood consistently ranks among the best places to live in Massachusetts. Buyers are drawn to the elegant homes, low-key luxury, and easy access to everything that matters — from Boston to Cape Cod.

Easy Commuter Access

Westwood's commuter access is hard to beat. Route 128/I-95 and I-93 intersect right in town, and the University Station area offers shopping, dining, and apartments surrounding the MBTA Route 128 stop. The Route 128 Amtrak station provides service to New York and Washington, while the Commuter Rail's Needham and Franklin lines deliver riders to Boston in about 30 minutes. Logan Airport is just 20 minutes away in light traffic.

Outdoor Lifestyle and Recreation

Westwood's open space and conservation land give residents plenty of room to roam. Hale Reservation offers swimming at Powisset Pond, hiking, and summer camps, while Lowell Woods and the Westwood Land Trust properties provide miles of trails. The town's youth sports, tennis courts, and playing fields stay active year-round, and Powisset Farm's CSA connects neighbors to fresh, locally grown food.

Westwood Real Estate Market Insights

Westwood's real estate market is defined by its premium inventory — stately colonials, custom-built new construction, and renovated classics on generous lots. Demand remains strong thanks to the school district and commuter advantages, and homes in desirable neighborhoods often see competitive offers. Whether you're looking for a move-in-ready estate or land to build your dream home, Westwood delivers a polished, long-term lifestyle investment.

Ready to explore homes in Westwood? Contact the realinsyghts group today at (508) 686-0940.

Find a home in Westwood, MA

$8,800,000
7 Beds ⋅ 8 Baths ⋅ 73457104 MLS
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 butler’s pantry, and a stunning chef’s kitchen that overlooks a fireplaced family room and a covered patio. There are 7 bedrooms highlighted by a stunning primary suite, as well as two offices, a playroom, an exercise room, and an attached, heated three-car garage. Outdoor amenities include a heated pool with a well-appointed pool house, a sport court, a stream-fed pond, and a barn-garage with a greenhouse and two horse stalls, along with a charming two-bedroom cottage. This exceptional property offers access to excellent public and private schools, Legacy Place, the train, and Boston via Rte. 95/128

401 Sandy Valley Rd, Westwood

Listing courtesy of Listing Agent: John Boyle from Listing Office: LandVest, Inc..
$7,750,000
8 Beds ⋅ 12 Baths ⋅ 73474238 MLS
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 atrium. The striking new chef’s kitchen adjoins the family room, casual dining room, and a separate terrace. A mahogany-paneled study with lounge and wet bar is ideal for private conferences. The residence offers 8+ en-suite bedrooms, including a grand primary suite with dual baths and a 20’x25’ walk-in closet. Two guest suites provide flexibility, each with a private entrance. The lower level includes a gym, sauna, steam, changing rooms, playroom, theater, wine cellar, and billiard room. Close to Rte 128/95 and top-rated schools.

18 Longmeadow Drive, Westwood

Listing courtesy of Listing Agent: John Boyle from Listing Office: LandVest, Inc..
$7,250,000
6 Beds ⋅ 8 Baths ⋅ 73509907 MLS
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 stunning chef’s kitchen at its center, expansive living and dining areas, multiple private offices, and a grand entry foyer, all enhanced by exquisite millwork and refined details throughout. Designed for both entertaining and comfortable living, the home extends outdoors to a resort-like setting with a pool, patio, fire pit, and sport court. Ideally located near top schools, major routes, commuter rail, and the town centers of Westwood, Needham, and Dedham.

111 Summer St, Westwood

Listing courtesy of Listing Agent: The Shulkin Wilk Group from Listing Office: Compass.
$6,950,000
5 Beds ⋅ 7 Baths ⋅ 73430073 MLS
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 formal living and dining rooms, and a chef’s kitchen opening to a spacious family room. The serene primary suite features a spa-like bath, dual closets, and sitting area. Outside, enjoy beautifully landscaped grounds, a peaceful pond, resort-style pool and cabana, plus a synthetic ice hockey practice area in the barn. Set back on a long private drive, this exceptional property offers the perfect balance of privacy, open space, and neighborhood living, while remaining convenient to Boston, top schools, and major commuter routes.

26 Longmeadow Drive, Westwood

Listing courtesy of Listing Agent: Donna Scott Group from Listing Office: Coldwell Banker Realty - Wellesley.
$5,999,000
6 Beds ⋅ 7 Baths ⋅ 73344054 MLS
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 bluestone terrace and grounds beyond. Additionally, there is a spacious kitchen, a butler’s pantry, and 2 wings offering separate living areas for family and guests. Upstairs is a large primary suite with separate baths, 2 ensuite bedrooms, and another bedroom and bath on the 3rd floor, for a total of 6 bedrooms and 6.5 baths. The spectacular grounds include a long private drive bordering the Dedham Country & Polo Club’s 18th fairway. The amazing back lawn is framed by a breathtaking conservatory-greenhouse, a lovely pool and cabana, a peaceful walking path, a tennis court and woods beyond.

429 Summer St, Westwood

Listing courtesy of Listing Agent: John Boyle from Listing Office: LandVest, Inc..
$4,495,000
6 Beds ⋅ 7 Baths ⋅ 73535655 MLS
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 countertop island for fabulous entertaining. This leads through a fully equipped butler's pantry to an unmatched dining room with built-in cabinetry, fireplace, and arched windows. Flooring of marble, tile and oak are found throughout, with views front to back. Or choose the magnificent sunroom, which steps out to stone patios for gatherings all across the yard with a level grassy area for endless possibilities. Walk the sidewalks with stately Boston street lamps. Fall asleep at night in luxury with a fireplace, spa bath ensuite, and choose your outfits in the morning from your two walk-in closets.

20 Longmeadow Drive, Westwood

Listing courtesy of Listing Agent: Peter Cwieka from Listing Office: Media Realty Group Inc..
$4,000,000
5 Beds ⋅ 4 Baths ⋅ 73542491 MLS
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 intimate library create a sophisticated backdrop for entertaining. Center island chef's kitchen and FP'd family room. Period details include custom millwork, French doors, a spacious butler’s pantry and multiple fireplaces. Expansive porches and patios overlook lush gardens and sweeping grounds, leading to a tucked-away pool. An oversized 3-car carriage house with loft adds further versatility. This rare offering includes a separate buildable lot, providing an opportunity for expansion or legacy compound. Minutes to the commuter rail, major routes, and premier shopping. An irreplaceable opportunity.

157 Grove Street, Westwood

Listing courtesy of Listing Agent: Bell Property Partners from Listing Office: Compass.
$3,490,000
5 Beds ⋅ 8 Baths ⋅ 73468161 MLS
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 room & fireplaced living room, this expansive home boasts a family room w/ soaring ceiling & double-sided stone fireplace open to a chef’s kitchen w/ a butler's pantry.The primary bedroom suite is a true sanctuary w/ fireplace, sitting room, morning kitchen, spa-like bathroom & two dressing rooms. Four additional bedrooms w/ baths showcase intricate & elegant tile work. Extraordinary entertainment level includes a climate controlled, dine-in wine room, kitchenette, bar, entertainment area, fitness, & game space. A poolhouse w/ kitchen & bath & serene resort-like setting complete this home.

9 Stonegate Dr, Westwood

Listing courtesy of Listing Agent: Michael Viano from Listing Office: Coldwell Banker Realty - Westwood.
$2,695,000
5 Beds ⋅ 6 Baths ⋅ 73551671 MLS
Exceptional custom Colonial built in 2018, ideally situated on a beautifully landscaped one-acre corner lot in Westwood's highly sought-after Pine Hill School District. Offering over 5,300 sq. ft., this meticulously maintained home features 5+ bedrooms, 5.5 baths, a stunning chef's kitchen with oversized island, granite countertops, stainless appliances, and an open floor plan to the fireplaced family room. A first-floor bedroom with full bath offers ideal au pair or in-law potential. Upstairs, the luxurious primary suite includes vaulted ceilings, a custom walk-in closet, and spa-like bath. Enjoy a covered rear porch with recessed lighting, ceiling fans, patio, and fire pit. Additional highlights include a 3-car garage, whole-house generator, double-wide mahogany staircase to a full basement with 9' ceilings ready for future expansion. Minutes to top-rated schools, shopping, commuter rail, and major routes.Open House Sunday, July 26, 12:00 - 2:00 p.m.

110 Rockmeadow Rd, Westwood

Listing courtesy of Listing Agent: Maher Realty Group from Listing Office: eXp Realty LLC.
$2,695,000
5 Beds ⋅ 5 Baths ⋅ 73550330 MLS
Classic and understated exterior belies the custom features of this custom built, sun-drenched, open-flow home with every imaginable high-end feature. Set on an idyllic roadway in a desired, walk to town neighborhood, this immaculate home is surrounded by mature plantings and features 9-foot ceilings and custom moldings throughout, amazing storage and room for expansion in the walk-up third level. Open-flow main level with hardwood flooring, chef's kitchen with high end cabinets and induction cooking plus generous pantry; formal dining room fireplaced great room with adjacent den and breakfast nook, sun room with access to the private yard; full bath, laundry room and mudroom complete the main level. Second floor features 4/5 bedrooms, including primary suite with walk in closets, a Jack & Jill bath plus an oversized office with closet and full bath. Fully finished basement with game room and gym plus cedar closet & half bath. All newer, top-of-the-line systems, air filtration, generator.

10 Rock Meadow Rd, Westwood

Listing courtesy of Listing Agent: Barbara Shea from Listing Office: Shea Realty Group.
$2,650,000
5 Beds ⋅ 6 Baths ⋅ 73497361 MLS
A must-see, beautifully designed custom Colonial with detailed millwork and gleaming hardwood floors throughout. The main level offers a formal living room/study, dining room, walk-in pantry, mudroom and half bath. The gourmet kitchen showcases high-end appliances and an 8ft island, flowing seamlessly into a sunlit breakfast area and family room with coffered ceilings, built-ins, and gas fireplace. Upstairs, the primary suite highlights a cathedral ceiling, walk-in closet, and en suite bath with double vanity, walk-in shower and tub. Four additional bedrooms, including two with private baths, a full bath and laundry room complete the upper level. The finished third level provides flexible bonus space and basement offers recreation area, gym, full bath, and access to the 3-car garage. Set on a beautifully landscaped corner lot, complete with covered pavilion and patio for year-round outdoor enjoyment. This is the home you’ve been looking for, offering everything you need and more!

11 Briarwood Dr, Westwood

Listing courtesy of Listing Agent: Yebba Roy Team from Listing Office: Coldwell Banker Realty - Westwood.
$1,895,000
4 Beds ⋅ 6 Baths ⋅ 73498155 MLS
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, inground pool, and poolside deck with pergola. Upstairs features versatile lounge/parlor area with half bath (ideal home office), gaming area, full bath, and 3 generous bedrooms including primary suite with ensuite bath. Third level offers spacious loft bedroom with full bath. Finished LL provides flexible space for media room, playroom, or guest suite w/ full bath and private entrance. Additional highlights: 2-car garage, charming front porch, expansive driveway, irrigation, propane generator, and two fireplaces. Rare opportunity offering space, privacy, and exceptional indoor-outdoor living!

10 Peartree Drive, Westwood

Listing courtesy of Listing Agent: Michael Tinsley from Listing Office: Longwood Residential, LLC.
$1,750,000
4 Beds ⋅ 4 Baths ⋅ 73529493 MLS
Custom colonial, with much detail and quality finishes. A bright entry, with grand stairway and wainscoting greets you. Large entertainment sized kitchen features white cabinets, granite countertops, stainless appliances and hardwood floors. The center island includes a pub height counter. The bar area is equipped with a sink and wine cooler. Kitchen includes a dining area, that overlooks the family room and fireplaced office.. There is a formal dining room and living room as well, if that is the mood you would like to create. The first floor also includes a half bath, laundry room and side entry mud room. The second floor consists of 4 generous bedrooms and 3 full baths. The primary suite has a walk in closet, and a stunning, new bathroom with jacuzzi tub and large shower. There is a walk up, unfinished attic and an unfinished basement that offer a blank slate to expand. This home has two new heating and air conditioning systems. New Pine Hill School.

3 Cardinal Dr, Westwood

Listing courtesy of Listing Agent: Virginia Sullivan from Listing Office: Coldwell Banker Realty - Westwood.
$1,298,000
5 Beds ⋅ 3 Baths ⋅ 73540144 MLS
Experience the distinguished allure of 76 Washington St, a magnificent single-family residence in Westwood, MA. Constructed in 1917, this expansive property spans 3,648 square feet of sophisticated living space, offering an unparalleled opportunity for refined living. The residence features five well-appointed bedrooms, providing ample private accommodations. Complementing these are two full bathrooms and one half bathroom, designed for both comfort and convenience. Further enhancing the property's functionality is a three-car garage, with solar panels offering substantial space for vehicles and additional storage. The generous lot size of 21,730 square feet provides a substantial private outdoor environment and garden. We invite you to discover the exceptional lifestyle this property affords. This home has had extensive updates since purchased in 2016!!!

76 Washington St, Westwood

Listing courtesy of Listing Agent: Linda Lerner from Listing Office: William Raveis R.E. & Home Services.
$997,000
4 Beds ⋅ 2 Baths ⋅ 73552475 MLS
Classic colonial home set on lush, private acre and set in the desired Martha Jones Elementary School district. The entry foyer is flanked by a front to back, fireplaced living room and formal dining room with a hall back to the eat-in kitchen, half bath and on to the generous family room with access to the deck and private back yard. Upstairs are four bedrooms and a full bath redone in 2011. Features include hardwood flooring, central air, gas heat and cooking, 2013 roof, replacement windows, partially finished basement, one car garage, irrigation system & recent MassSave energy improvements. Showings start at open houses Thursday, July 23, 5 to 7pm and Saturday, July 25 11am to 1pm.

485 Oak St, Westwood

Listing courtesy of Listing Agent: Barbara Shea from Listing Office: Shea Realty Group.
$949,000
3 Beds ⋅ 2 Baths ⋅ 73550060 MLS
Available for the first time in 60 years! Embrace the opportunity to renovate or expand this proudly maintained 2,097± SF brick front Colonial set on a private lot & located in one of Westwood's most coveted side street neighborhoods. The first floor with sparkling wood floors features a gracious front entry hall, elegant formal living room with fireplace & built-in bookshelves, cozy den, formal dining room with wainscoting & built-in cupboard, powder room & vintage eat-in kitchen. The second floor is complete with a large primary bedroom with walk-in closet, two additional bedrooms & a full hall bathroom. A staircase provides easy access to the attic. The finished lower level includes a recreation room with recessed lighting, laundry room & unfinished space that accommodates mechanical systems & storage. Updated roof, heating system, 200 Amp electrical panel & central air. Enjoy quick access to Hale Reservation, Westwood center, schools, Rt. 109 & I-95 & Legacy Place.

78 Lorraine Road, Westwood

Listing courtesy of Listing Agent: Tom Aaron from Listing Office: Coldwell Banker Realty - Wellesley.
$899,900
3 Beds ⋅ 2 Baths ⋅ 73530559 MLS
Beautiful split-level ranch in a quiet, sought-after Westwood neighborhood offering approx. 2,000 sq. ft. of flexible living space. The main level features a bright living room with fireplace and hardwood floors, two bedrooms, a full bath, and a spacious eat-in kitchen. The walk-out lower level includes a large family room, third bedroom, full bath, and laundry. Enjoy a fully fenced backyard perfect for play, pets, and outdoor entertaining. Conveniently located near top-rated schools, parks, commuter rail, Route 1, I-95, and shopping at University Station. A wonderful opportunity to enjoy comfort, space, and an ideal Westwood location.

43 Deerfield Ave, Westwood

Listing courtesy of Listing Agent: Entela Tase from Listing Office: Coldwell Banker Realty - Westwood.
$850,000
5 Beds ⋅ 2 Baths ⋅ 73517444 MLS
Now is your chance to move to Westwood before school begins! 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 offers a private outdoor setting. Lots of room for recreation, gardening and/or an ADU or potential home expansion. Relax on the patio, listen to the birds & enjoy alfresco dining. Upgraded insulation & central a/c enhance year-round comfort & improves energy efficiency. Explore the opportunity to acquire a lovingly maintained residence rarely found at this price in Westwood. Shops/restaurants at Legacy Place and University Ave., medical facilities & commuter rail are minutes away. Buyers/agent to perform their own due diligence. Seller/agent make no representations.

12 Westwood Ter, Westwood

Listing courtesy of Listing Agent: Roberta Dehman Hershon from Listing Office: LAER Realty Partners.
$849,900
5 Beds ⋅ 2 Baths ⋅ 73484143 MLS
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 lifestyle, featuring bright living and dining areas with hardwood floors, a modern kitchen with quartz countertops and recessed lighting, and a first-floor bedroom perfect for guests or a home office. Upstairs offers additional bedrooms and half bath. Unfinished walk-out lower level and unfinished second-floor space provide exciting expansion potential. Enjoy a peaceful private yard surrounded by nature, plus a detached 2-car garage and ample parking.

290 East Street, Westwood

Listing courtesy of Listing Agent: DeWolfe Group from Listing Office: Gibson Sotheby's International Realty.
$799,000
2 Beds ⋅ 2 Baths ⋅ 73550537 MLS ⋅ ['Westwood Place'] BLDG.
Newly luxury condo ready for move in! This 2B2B unit is the best in the building and comes with a garage parking spot! Covered by hardwood floors, the unit is 1320 sq ft with everything you need! Enjoy numerous upgrades installed during construction. There is an open living space with a granite countertop kitchen that has its own island, stainless steel appliances, a large fridge and gas range. A private balcony is attached to the central space. Both bedrooms are spacious and comfortable. Inside the master there are two large walk-in closets. SUPERB LOCATION! Walking distance to AMTRAK & MBTA lines means going to Boston takes less than 20 min! 2 min walk to Westwood Mall has everything you need from Wegmans, Target, Nordstrom Rack, HomeGoods, restaurants, coffee shops, gyms and much more! Easy access to R95 & R93 also means driving anywhere is a breeze.

120 University Ave Unit 2308, Westwood

Listing courtesy of Listing Agent: The Ridick Revis Group from Listing Office: Compass.
$749,900
3 Beds ⋅ 1 Baths ⋅ 73548981 MLS
Tucked away on a quiet side street in a desirable Westwood neighborhood, 12 Dean Ave combines charm, functionality, and an exceptional location. Filled with natural light from numerous windows, the home offers a warm and inviting atmosphere from the moment you step inside. Hardwood floors span much of the interior, while the open kitchen flows seamlessly into the dining area, creating an ideal space for everyday living and entertaining. Expansive views of the spacious backyard bring the outdoors in and provide a beautiful backdrop throughout the year.The first floor features a primary bedroom with an adjoining office or sitting area, offering flexibility to suit your needs, as well as the main bathroom. Upstairs, two additional comfortable bedrooms provide added versatility. Ideally situated near shopping, dining, community amenities and major commuting routes, this property presents a wonderful opportunity to enjoy all that Westwood has to offer.

12 Dean Ave, Westwood

Listing courtesy of Listing Agent: The Ultan and Caitlyn Team from Listing Office: Insight Realty Group, Inc..
$699,000
3 Beds ⋅ 1 Baths ⋅ 73553188 MLS
Welcome to this storybook Cape-style home, where cherished memories are waiting to be made! Nestled in Westwood's beloved "Maze" neighborhood, known for its strong sense of community and festive Halloween trick-or-treating, this home is less than a mile from top-ranked Westwood High School and Middle Schools, the Senior Center, the Tot Lot, Buckmaster Pond, & local cafés. Bright, airy, and beautifully maintained, this sunny 3-bedroom, 1-bath home is filled with natural light and hardwood floors throughout most of the home. Enjoy casual meals & morning coffee in the kitchen banquette, then host family & friends in the spacious living and dining rooms. Outside, the white picket fence, blue hydrangeas, and a climbing tree create a picture-perfect setting. Spend summer evenings grilling in the private backyard, watching kids play, or unwinding on the patio with a good book. A detached one-car garage and spacious basement provide excellent storage & parking. Make this your Home Sweet Home!

39 Fisher Street, Westwood

Listing courtesy of Listing Agent: Meghan Collins from Listing Office: RE/MAX Distinct Advantage.
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