Wellesley Hills, MA Homes for Sale with Acreage

• 

  

  

  /21

  $3,750,000

  $225K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 8,273 Sq Ft

  957 South St, Needham, MA 02492

  This masterfully designed new construction home offers over 8,000 square feet of refined living space across four finished levels. Situated on a private acre-plus lot in one of Needham’s most desirable neighborhoods, the property perfectly balances sophisticated entertaining with everyday comfort. The residence features six elegant bedroom suites with custom closets, including a convenient

  Jill Finkelstein & Associates Compass

  957 South St, Needham, MA 02492
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /40

  $1,675,000

  $215K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,345 Sq Ft

  40 Hobbs Brook Rd, Weston, MA 02493

  Introducing a sophisticated contemporary retreat offering exceptional privacy, tranquil surroundings, and a seamless connection to nature. The open, versatile layout blends indoor and outdoor living for an elevated entertaining experience.The well-appointed kitchen flows into a spacious dining area and multiple inviting sitting spaces. Three beautifully designed bedrooms, including a bright and

  Mizner+ Montero Gibson Sotheby's International Realty

  40 Hobbs Brook Rd, Weston, MA 02493
• 

  

  

  /26

  $2,670,000

  $25K PRICE DROP

  • 5 Beds
  • 7 Baths
  • 9,967 Sq Ft

  7 Schoolmaster Ln, Dedham, MA 02026

  Welcome to 7 Schoolmaster Lane, a distinguished residence offering luxury, privacy, and refined living in one of Dedham’s most desirable neighborhoods.From the moment you enter, you’re greeted by soaring ceilings, sun-filled interiors, and a thoughtful layout designed for both everyday comfort and elevated entertaining. The main living spaces flow seamlessly into a chef’s kitchen featuring

  Courtney Gonsalves Coldwell Banker Realty - Beverly

  7 Schoolmaster Ln, Dedham, MA 02026
• 

  

  

  /28

  $634,000

  $5K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 899 Sq Ft

  250 Hammond Pond Pkwy Unit 604N, Chestnut Hill, MA 02467

  Towers of Chestnut Hill, residence 604N, no expense has been spared to create this sophisticated home. This magazine worthy unit is renovated to the highest standard with quality craftmanship throughout. Top of line finishes and thoughtfully designed choices created this perfect condominium. This home showcases tremendous space, light and well-proportioned rooms and allows entertaining on an

  Richard C. Dore Hammond Residential Real Estate

  250 Hammond Pond Pkwy Unit 604N, Chestnut Hill, MA 02467
• 

  

  

  /35

  $16,900,000

  • 6 Beds
  • 10 Baths
  • 10,116 Sq Ft

  50 Winsor Way, Weston, MA 02493

  A true showcase luxury gated estate, 50 Winsor Way is situated on over 2 acres of elevated and private land located off the Weston Golf Club. The estate features truly picturesque professionally landscaped grounds, expansive terraces and patios with views for entertaining, and a large showpiece swimming pool and patio with elegant fountains. 50 Winsor boasts more than 6 bedrooms including the

  Rose Hall Blue Ocean Realty, LLC

  50 Winsor Way, Weston, MA 02493
• 

  

  /30

  $1,695,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 4,705 Sq Ft

  242 Winter St, Weston, MA 02493

  Set on a beautifully landscaped 1.43-acre lot, this contemporary Cape-style home blends spacious living with architectural character and resort-style amenities. Offering 3 bedrooms, including a private primary suite with en suite bath, the home is designed for both everyday comfort and effortless entertaining. The dramatic great room features soaring ceilings, skylights, fireplace, and wet bar,

  Denise Mosher Coldwell Banker Realty - Weston

  242 Winter St, Weston, MA 02493
• 

  

  /37

  $3,595,000

  $155K PRICE DROP

  • 7 Beds
  • 7 Baths
  • 6,710 Sq Ft

  64 Country Dr, Weston, MA 02493

  Stately brick-front Colonial nestled on 2.45 spectacular acres in Weston’s highly coveted South Side Estates. This exceptional property seamlessly blends timeless elegance with modern luxury. A grand foyer welcomes you into a front-to-back living room with a cozy fireplace and an elegant formal dining room. The newly renovated chef’s kitchen is equipped with top-tier appliances, including Wolf

  Mizner+ Montero Gibson Sotheby's International Realty

  64 Country Dr, Weston, MA 02493
• 

  

  /38

  $2,650,000

  • 5 Beds
  • 5 Baths
  • 4,931 Sq Ft

  125 Oxbow Rd, Needham, MA 02492

  Beautifully maintained, sited on 1.78 lush, level acres with access to the Charles River, this 13-room home offers exceptional space and versatility. Featuring 4/5 bedrooms, 3 full and 2 half baths, this totally updated home has a very inviting living room and family room with fireplaces and built-ins, a first floor study as well as an office/bedroom with private entrance. The eat-in kitchen

  Jill Finkelstein & Associates Compass

  125 Oxbow Rd, Needham, MA 02492
• 

  

  /10

  $5,395,000

  • Land
  • 7.28 Acres
  • $741,071 per Acre

  475 Glen Rd, Weston, MA 02493

  Discover 7.28 acres of pristine land offering exceptional privacy, tranquility, and natural beauty in one of Massachusetts’ most sought-after communities. This remarkable parcel presents a rare opportunity to create a custom luxury estate surrounded by mature trees, open space, and a serene natural landscape. Located in Weston, the property offers the perfect balance of peaceful country living

  Julie Harrison Gibson Sotheby's International Realty

  475 Glen Rd, Weston, MA 02493
• 

  

  /36

  $2,149,000

  $436K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 5,216 Sq Ft

  7 Circle Dr, Dover, MA 02030

  This beautiful 4BR 5.5BA home is conveniently set in a popular neighborhood near the Needham/Wellesley line. The open-concept first floor features a stunning gourmet kitchen with custom cabinetry, quartz countertops, a dramatic waterfall island & premium appliances. The kitchen flows seamlessly into the family room with sliders to the backyard, as well as the fireplaced living room, dining area,

  Mary Crane Berkshire Hathaway HomeServices Commonwealth Real Estate

  7 Circle Dr, Dover, MA 02030
• 

  

  /33

  $4,388,888

  $196K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 9,825 Sq Ft

  68 Locust Ln, Needham, MA 02492

  68 Locust Lane is a rare estate-style residence set on over one acre of beautifully flat private land on a quiet cul-de-sac along the prestigious Needham–Wellesley line. This exceptional new construction home blends timeless architecture, modern luxury, and outstanding craftsmanship throughout. A dramatic two-story foyer welcomes you into expansive entertaining spaces featuring formal living and

  Alex Kuzakovsky Luna Luxury Realty

  68 Locust Ln, Needham, MA 02492
• 

  

  /42

  $2,395,000

  Open Sun 11:30AM - 1PM $200K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 5,496 Sq Ft

  11 Haven St, Dover, MA 02030

  This custom-built Colonial, ideally located near Dover Center, showcases elegant craftsmanship and a modern open floor plan. The main level features a great room with soaring ceilings, double-sided fieldstone fireplace and chef’s kitchen complete with quartz counters and SubZero fridge adjacent to a family room with built-ins and walkout deck. Enjoy your own private sanctuary with bluestone patio

  Neda Vander Stoep Coldwell Banker Realty - Boston

  11 Haven St, Dover, MA 02030
• 

  

  /19

  $7,550,000

  • 6 Beds
  • 9 Baths
  • 8,863 Sq Ft

  132 Country Dr, Weston, MA 02493

  Designed for elevated everyday living and effortless entertaining, this exceptional residence at 132 Country Drive in Weston offers the perfect blend of luxury, comfort, and convenience. Set in one of Weston’s most desirable neighborhoods—known for its top-ranked schools and peaceful surroundings—the home is just minutes from Boston and major commuter routes. Inside, an oversized chef’s kitchen

  Sheryl Simon Gibson Sotheby's International Realty

  132 Country Dr, Weston, MA 02493
• 

  

  /41

  $2,299,000

  • 5 Beds
  • 4.5 Baths
  • 5,908 Sq Ft

  175 Schoolmasters Ln, Dedham, MA 02026

  A rare opportunity to own a luxury home in one of Dedham's most sought-after neighborhoods. Now offered at an exceptional value, this privately situated home on a cul-de-sac and private road offers nearly 6,000 square feet of thoughtfully designed living space across four finished levels and is available for immediate occupancy. Sun-filled interiors feature coffered ceilings, custom millwork, and

  Maria Gorman Coldwell Banker Realty - Westwood

  175 Schoolmasters Ln, Dedham, MA 02026
• 

  

  /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
• 

  

  /42

  $5,999,000

  • 4 Beds
  • 7 Baths
  • 7,600 Sq Ft

  44 Meadowbrook Rd, Weston, MA 02493

  This California Contemporary defines sophisticated living at its finest. Majestically nestled on 2 private, stunning acres in the coveted Weston Country Club neighborhood.The terraced grounds are accented with stone patios, a salt water pool and cabana. Soaring ceilings and an abundance of sunlight flood the multiple levels of thoughtfully designed living spaces. A dramatic family room has

  Mizner+ Montero Gibson Sotheby's International Realty

  44 Meadowbrook Rd, Weston, MA 02493
• 

  

  /27

  $1,675,000

  • 4 Beds
  • 3 Baths
  • 2,840 Sq Ft

  37 School St, Weston, MA 02493

  Beautifully sited on over 2 private acres, this 8-room, 4-bed, 3-bath home offers comfort, charm, and room to grow. The spacious living room features a fireplace and hardwood floors, flowing into a formal dining room with two classic corner cabinets and a sun-filled kitchen with white cabinetry, stainless appliances, and center island. Two generous bedrooms and a full bath complete the first

  Denise Mosher Coldwell Banker Realty - Weston

  37 School St, Weston, MA 02493
• 

  

  /37

  $9,500,000

  • 6 Beds
  • 9 Baths
  • 12,117 Sq Ft

  43 Pine St, Weston, MA 02493

  One of South Side Weston’s most exceptional estate offerings, privately sited on 2.4 breathtaking resort-like acres. Meticulously maintained and masterfully renovated, this distinguished residence seamlessly blends timeless architecture with sophisticated modern luxury. Sun-drenched interiors and exquisite craftsmanship define every space, highlighted by a spectacular vaulted family room and

  Jill Boudreau eXp Realty LLC - Corporate Office

  43 Pine St, Weston, MA 02493
• 

  

  /26

  $625,000

  $10K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 899 Sq Ft

  250 Hammond Pond Pkwy Unit 609S, Chestnut Hill, MA 02467

  The Towers of Chestnut Hill is a 5-star luxury condominium association. Hammond Pond Parkway's most prominent building embodies the very essence of luxury Chestnut Hill living. Fully amenitized living, including heated indoor swimming pool, newly installed gym, brand new pickleball court and 24-hour doorman underscores it all. On rare occasions, a one bedroom, 1.5 bath renovated unit becomes

  Richard C. Dore Hammond Residential Real Estate

  250 Hammond Pond Pkwy Unit 609S, Chestnut Hill, MA 02467
• 

  

  /32

  $850,000

  $70K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 2,124 Sq Ft

  82 Cottage St, Natick, MA 01760

  Some homes simply provide shelter. This one becomes the backdrop for the life you've been dreaming of. Tucked alongside conservation land in one of Natick's most desirable locations, this updated 3-bedroom, 1.5-bath home offers a rare blend of tranquility & convenience. Begin your mornings on the covered deck overlooking a peaceful natural landscape where birds provide the soundtrack & the

  Sherry Stallings Real Broker MA, LLC

  82 Cottage St, Natick, MA 01760
• 

  

  /38

  $4,595,000

  $400K PRICE DROP

  • 6 Beds
  • 7 Baths
  • 7,000 Sq Ft

  21 Westerly Rd, Weston, MA 02493

  1.38 acres of flat land in coveted Weston Estates! Stunning shingle and stone 6 bedroom Colonial. Extraordinary outdoor space featuring a pavilion with kitchen plus stone fireplace perfect for outdoor living and entertaining. Large kitchen with oversized island and seating area opens to double storeyed family room along with beautiful floor to ceiling stone fireplace, wet bar and incredible

  Melissa Dailey Coldwell Banker Realty - Wellesley

  21 Westerly Rd, Weston, MA 02493
• 

  

  /30

  $4,149,000

  $300K PRICE DROP

  • 6 Beds
  • 7.5 Baths
  • 7,185 Sq Ft

  8 Crestview Rd, Needham, MA 02492

  Set on a beautifully landscaped one-acre lot, this exceptional new construction home offers the prestige of the estate side of town with a rare sense of privacy and space. Spanning over 7,100 sq ft, the residence features 6 beds, 7.5 baths, and refined craftsmanship throughout. The chef’s kitchen includes top-of-the-line appliances, an oversized island, and a working pantry, opening to a

  Connor Gillen Keller Williams Realty

  8 Crestview Rd, Needham, MA 02492
• 

  

  /27

  $525,000

  $25K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 948 Sq Ft

  51 Pettee St Unit 47, Newton Upper Falls, MA 02464

  Architecturally distinctive two level loft thoughtfully redesigned with bespoke built-ins, dedicated workspaces, and exceptional storage throughout. Sunlight fills the dramatic living area, where soaring ceilings, oversized windows, and warm hardwood floors create an inviting space for everyday living and entertaining. The updated kitchen features custom cabinetry, premium appliances and generous

  Stephanie Nahon William Raveis R.E. & Home Services

  51 Pettee St Unit 47, Newton Upper Falls, MA 02464
• 

  

  /39

  $3,795,000

  • 6 Beds
  • 6.5 Baths
  • 8,182 Sq Ft

  365 Charles River St, Needham, MA 02492

  Built in 2025, this exceptional 6BR/6.5BA residence offers superior quality & craftsmanship. A dramatic two-story foyer opens to meticulously curated living spaces. The chef's kitchen showcases premium appliances, custom cabinetry, a pantry & the island seamlessly flows into elegant dining & living areas designed for effortless entertaining. The breathtaking family room is distinguished by a

  Beyond Boston Properties Group Compass

  365 Charles River St, Needham, MA 02492
• 

  

  /38

  $4,388,000

  $300K PRICE DROP

  • 5 Beds
  • 7 Baths
  • 8,844 Sq Ft

  568 Wellesley St, Weston, MA 02493

  Elegant Custom Estate on 1.8 Acres in Weston! This stunning 8,000+ sq ft Colonial sits on a beautifully landscaped, level 1.8-acre lot with a private drive and circular entry. Inside, a grand foyer with a sweeping staircase opens to formal living and dining rooms with soaring ceilings, crown moldings, and French doors. The gourmet kitchen with marble countertops, super high-end & branded

  Rose Hall Blue Ocean Realty, LLC

  568 Wellesley St, Weston, MA 02493
• 

  

  /21

  $750,000

  • 2 Beds
  • 2 Baths
  • 1,311 Sq Ft

  250 Hammond Pond Pkwy Unit 1208N, Chestnut Hill, MA 02467

  Wake up each morning to breathtaking sunrise views from this spectacular 12th-floor, 2-bedroom, 2-bath residence at the prestigious Towers of Chestnut Hill. This beautifully maintained home offers spacious living, with in-unit laundry. Enjoy an unmatched lifestyle with exceptional amenities, including a 24-hour concierge and doorman, an indoor heated swimming pool, fitness center, pickleball and

  Richard C. Dore Hammond Residential Real Estate

  250 Hammond Pond Pkwy Unit 1208N, Chestnut Hill, MA 02467
• 

  

  /37

  $6,975,000

  • 6 Beds
  • 7.5 Baths
  • 8,773 Sq Ft

  5 Deer Path Ln, Weston, MA 02493

  This newly-constructed, Contemporary offers the pinnacle of luxury living on Weston’s coveted Southside. The dramatic, 2-story foyer flows seamlessly into both formal and informal spaces. The dining / living room is optimal for family gatherings & entertaining, and the custom kitchen w/an exceptional quartz island, high-end appliances and wet bar adjoins a generous eat-in area and fireplaced

  Beyond Boston Properties Group Compass

  5 Deer Path Ln, Weston, MA 02493
• 

  

  /18

  $7,200,000

  • Land
  • 3 Acres
  • $2,400,000 per Acre

  21 Eliot St, Natick, MA 01760

  Presenting 21 Eliot Street, 3 acres of beautifully maintained and natural grounds in Natick, Massachusetts. Currently improved by four well-preserved buildings featuring a mix of office and retail spaces, the property presents an unparalleled opportunity for commercial and residential redevelopment. The underlying zoning of 70% RSC and 30% CII allows for a multitude of development options. The

  Chris Sower Cushman & Wakefield

  21 Eliot St, Natick, MA 01760
• 

  

  /36

  $6,750,000

  • 5 Beds
  • 9 Baths
  • 10,819 Sq Ft

  15 Brown St, Weston, MA 02493

  Introducing a timeless European inspired mansion with a private gate and elegant marble fountain. This custom estate is situated on 3 acres. A spectacular pool and spa complemented by a fully equipped pool house with a kitchen adorn the grounds. A beautiful wrought iron fence embraces the entire estate which includes stone patios and tennis court. The grand entry and living and dining rooms boast

  Mizner+ Montero Gibson Sotheby's International Realty

  15 Brown St, Weston, MA 02493
• 

  

  /18

  $3,490,000

  • 5 Beds
  • 6 Baths
  • 6,050 Sq Ft

  181 Dedham St, Dover, MA 02030

  NEW CONSTRUCTION on 3.5+ acres of beautiful DOVER land in the coveted & convenient east-side of town with esteemed local builder known for delivering superior workmanship & high-end finishes! This gorgeous 5 bedroom, 4/2 Bath home includes 6000+ sqft of finished living area over 3 expertly crafted levels and could include every imaginable amenity on both the interior & exterior to assure elegant

  Laura Mastrobuono Compass

  181 Dedham St, Dover, MA 02030
• 

  

  /41

  $1,989,000

  New Construction Open Sun 12PM - 3PM $10K PRICE DROP

  • 3 Beds
  • 4.5 Baths
  • 4,074 Sq Ft

  62 Claybrook Rd, Dover, MA 02030

  Seller offering huge Mortgage rate buy down ask agentfor details. This home is minutes to both the Dover and Needham town centers and less than 30 minutes to Boston. This 4074 sq.ft home offers 3 bdrms(all with ensuites), plus an extra 4th bonus room to tailor to your needs. Enjoy a contemporary open concept first floor featuring an inviting fireplaced living room, sunlit dining area, and gourmet

  Martin Keogh Offices of Martin J. Keogh

  62 Claybrook Rd, Dover, MA 02030

Showing Results 41 - 71, Page 2 of 2