Wellesley Hills, MA Homes for Sale with Acreage

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  /40

  $2,725,000

  • 5 Beds
  • 6 Baths
  • 5,773 Sq Ft

  18 Old Colony Dr, Dover, MA 02030

  Tucked away at the end of a quiet cul-de-sac, this 5-bedroom Colonial is one of those rare homes that’s big enough for grand entertaining but still feels like a cozy family retreat. The elegant foyer with a sweeping circular staircase sets the tone for this gracious and updated home. Enjoy formal dining and living rooms, a spacious family room, office, and an open-concept kitchen/sunroom ideal

  

  Amy Caffrey

  Compass

  (508) 501-7244

  18 Old Colony Dr, Dover, MA 02030
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  /41

  $2,625,000

  • 4 Beds
  • 5 Baths
  • 6,056 Sq Ft

  8 Buttercup Ln, Dover, MA 02030

  Nestled at the end of a quiet private road, this charming red brick French Colonial offers a blend of classic style and modern comfort.The heart of the home is the updated chef’s kitchen.The impressive space features SS Wolf appliances, a large island outfitted with freezer drawers, prep sink and plenty of space for seating. An inviting f/p flanked by built-ins and a large bow window set the

  

  Amy Caffrey

  Compass

  (508) 682-5494

  8 Buttercup Ln, Dover, MA 02030
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  /15

  $594,000

  • 2 Beds
  • 1 Bath
  • 1,060 Sq Ft

  51 Pettee St Unit 31, Newton Upper Falls, MA 02464

  Architecturally unique 2-bedroom residence at the Falls Ridge featuring soaring high ceilings and oversized windows that fill the home with natural light. The expansive living area showcases parquet wood floors and a dedicated dining space, creating a sophisticated setting for both everyday living and entertaining. The primary bedroom features a walk-in closet with direct access to the bathroom,

  

  Kelly Roche

  Engel & Volkers Boston

  (857) 754-6524

  51 Pettee St Unit 31, Newton Upper Falls, MA 02464
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  /35

  $1,950,000

  • 5 Beds
  • 4 Baths
  • 3,962 Sq Ft

  47 Springdale Ave, Dover, MA 02030

  Experience timeless New England charm with modern ease in this 5-bed/4 bath farmhouse, steps from Channing Pond for fishing,skating,or quiet reflection.Period lighting, stained glass,hardwood floors,detailed millwork,&french doors w/crystal knobs add character. The heart of the home is a warm, inviting kitchen that opens to a dramatic cathedral-ceiling family room, perfect for gatherings. A

  

  Amy Caffrey

  Compass

  (508) 980-2878

  47 Springdale Ave, Dover, MA 02030
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  /42

  $2,850,000

  • 5 Beds
  • 4.5 Baths
  • 6,719 Sq Ft

  25 Pleasant St, Dover, MA 02030

  Set on over an acre in one of Dover’s most desirable neighborhoods, this exceptional 6,700+ sq ft residence blends architectural character with natural beauty. The open-concept main level features soaring ceilings, rich wood accents, skylights, and expansive walls of glass that fill the home with natural light. The kitchen flows seamlessly into multiple gathering spaces, ideal for both everyday

  Anush Showghi Berkshire Hathaway HomeServices Warren Residential

  25 Pleasant St, Dover, MA 02030
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  /41

  $3,495,000

  • 5 Beds
  • 5.5 Baths
  • 6,280 Sq Ft

  20 Wheeler Ln, Natick, MA 01760

  Set on a private 1.1-acre lot surrounded by mature trees, this reimagined 1880s stone farmhouse offers a lifestyle of luxury and elegance. Spanning 6,280 square feet, it seamlessly blends New England charm with Arts and Crafts detailing. The foyer’s dramatic floating spiral staircase sets the stage for a grand yet inviting atmosphere. The chef’s kitchen flows into a casual dining area and sunlit

  Better Home Team Coldwell Banker Realty - Boston

  20 Wheeler Ln, Natick, MA 01760
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  /26

  $775,000

  • 2 Beds
  • 2 Baths
  • 1,285 Sq Ft

  250 Hammond Pond Pkwy Unit 102N, Chestnut Hill, MA 02467

  From the moment you drive up to the imposing porte-cochere, the Towers offers the ultimate in privacy, service and luxury. Fully amenitized living, including indoor swimming pool, gym, tennis courts and brand new pickleball court. Enjoy effortless, luxurious, city living at the Towers. This bright first floor welcoming home with gracious entrance foyer/hall and updated kitchen- needs no work

  Richard C. Dore Hammond Residential Real Estate

  250 Hammond Pond Pkwy Unit 102N, Chestnut Hill, MA 02467
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  /40

  $4,250,000

  • 4 Beds
  • 6 Baths
  • 5,018 Sq Ft

  105 Summer St, Weston, MA 02493

  Unmatched quality and craftsmanship define this architecturally inspired new home. Maple wood floors, cherry paneled walls and expansive German triple-glazed windows create its curated aesthetic. An expertly designed kitchen with a huge island, custom window seat, and generous dining area open seamlessly to the family room anchored by a striking marble fireplace. The first floor primary suite

  Mizner+ Montero Gibson Sotheby's International Realty

  105 Summer St, Weston, MA 02493
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  /40

  $4,680,000

  • 6 Beds
  • 6.5 Baths
  • 7,658 Sq Ft

  83 Brown St, Weston, MA 02493

  This recently built custom home presents a modern design and refined detail. A dramatic two-story foyer and the open family room make an immediate statement. The dining room complements the open and airy floor plan with beautiful hardwood floors and soaring ceilings The stylish kitchen features a large center island, wet bar, and spacious dining area opening to a sun-filled family room accented

  Mizner+ Montero Gibson Sotheby's International Realty

  83 Brown St, Weston, MA 02493
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  /28

  $4,199,000

  • 4 Beds
  • 6 Baths
  • 6,626 Sq Ft

  253 Highland St, Weston, MA 02493

  This beautiful colonial estate, located in the coveted South Side of Weston, offers an amazing combination of privacy and convenience. Set on 3.36 acres of private land, its prime location provides easy access to major highways, including I-90 and I-95. The first level features an open floor plan highlighted by a large kitchen featuring cherry wood and granite tops and equipped with premium

  Rose Hall Blue Ocean Realty, LLC

  253 Highland St, Weston, MA 02493
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  /34

  $5,250,000

  • 5 Beds
  • 8 Baths
  • 5,810 Sq Ft

  9 Skating Pond Rd, Weston, MA 02493

  Reimagined & redesigned stunning custom home on over 1 acre in Weston's prestigious Golf Club neighborhood. New layout, new floors, new custom built-ins, new kitchen, new butler pantry, new bathrooms, new moudings, white oak door trim, new furnaces, new AC condensers, new Marvin windows, new stone walls & landscaping...... Kitchen family room w/ breakfast nook opens to large family room w/

  Melissa Dailey Coldwell Banker Realty - Wellesley

  9 Skating Pond Rd, Weston, MA 02493
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  /40

  $5,250,000

  • 6 Beds
  • 8 Baths
  • 9,036 Sq Ft

  12 Winding River Cir, Wellesley, MA 02482

  Exceptional property on the Charles River! 2.89 acres of manicured lawn rolls down to the river giving you unobstructed views & private use of a nature lover's paradise. Gorgeous stone patios, multiple decks, & sun-filled rooms w/French Doors are all designed to maximize your enjoyment of this incredible retreat. Privately nestled on a quiet cul-de-sac, this stunning Cape is beautiful in all

  Betsy Kessler Rutledge Properties

  12 Winding River Cir, Wellesley, MA 02482
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  /30

  $6,500,000

  • 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
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  /42

  $4,250,000

  • 6 Beds
  • 5 Baths
  • 6,990 Sq Ft

  151 Oakland St, Wellesley Hills, MA 02481

  Located in the Country Club neighborhood on 1.15 acres, overlooking Wellesley Country Club greens, with sweeping scenic golf course views. Fully renovated in 2022, this distinguished home blends historic character with refined luxury, featuring wide pine floors, 6 fireplaces, and walls of windows overlooking the greens. Gracious living spaces include an inviting fire-placed great room,

  Beth Dickerson Gibson Sotheby's International Realty

  151 Oakland St, Wellesley Hills, MA 02481
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  /39

  $3,495,000

  • 5 Beds
  • 7 Baths
  • 5,023 Sq Ft

  172 Country Dr, Weston, MA 02493

  Incredible renovations to this stately brick colonial on a professionally landscaped 1.58 acres. Private views and wooded paths in the back yet nestled in one of Weston's favorite Southside neighborhoods. This 5/6 bedroom home has been transformed. Extensive improvements with new appliances in the kitchen that opens into a breakfast area with wetbar. Walk- in food pantry. Family room with

  Melissa Dailey Coldwell Banker Realty - Wellesley

  172 Country Dr, Weston, MA 02493
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  /40

  $3,999,000

  • 5 Beds
  • 5.5 Baths
  • 5,519 Sq Ft

  389 Grove St, Needham, MA 02492

  Set on exceptionally private acreage along the coveted Needham–Wellesley line, this reimagined estate offers rare scale, serenity, and sophistication. A comprehensive 2021 renovation transformed the home into a luxurious yet welcoming retreat, designed for both everyday living and refined entertaining. The heart of the home is the true chef’s kitchen with intentional, top-of-the-line finishes,

  Berlin Levin Team Coldwell Banker Realty - Wellesley

  389 Grove St, Needham, MA 02492
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  /42

  $4,195,000

  • 6 Beds
  • 6.5 Baths
  • 7,867 Sq Ft

  1780 Central Ave, Needham, MA 02492

  Experience modern luxury in this new construction residence, perfectly situated on an expansive, 1 acre level lot in a convenient Needham location. Thoughtfully designed with high ceilings, abundant natural light, GAS heating and cooking, and refined finishes, this 6 bedroom, 6.5 bath property combines comfortable elegance at every turn and includes a unique attached ADU, w/ private entry—

  Beyond Boston Properties Group Compass

  1780 Central Ave, Needham, MA 02492
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  /21

  $3,849,000

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

  957 South St, Needham, MA 02492

  LUXURY! PRIVACY! PERFECTION! Experience over 8,000 square feet of masterfully designed living on a private acre-plus lot in one of Needham’s most desirable locations. This exceptional new construction showcases six elegant bedroom suites with custom closets, a chef’s kitchen featuring a La Cornue range, an oversized island, and dual pantries, ideal for entertaining and everyday living! The four

  Jill Finkelstein & Associates Compass

  957 South St, Needham, MA 02492
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  /27

  $4,349,000

  • 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
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  /37

  $4,388,000

  • 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
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  /42

  $3,950,000

  • 5 Beds
  • 8 Baths
  • 8,555 Sq Ft

  4 Claybrook Rd, Dover, MA 02030

  Exquisite antique country estate sited on 3.48 acres of manicured lawns and vibrant gardens, bordered by stone patios and a fabulous inground pool tucked among specimen trees for exceptional privacy. A circular drive leads to a spectacular 17-room, five-bedroom retreat, plus a 2009 carriage house with 2/3 bay heated garage, indoor lap pool, full bath, sauna, office/music room, and impressive gym.

  Martha Bohlin Compass

  4 Claybrook Rd, Dover, MA 02030
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  /2

  $3,195,000

  • 7 Beds
  • 7.5 Baths
  • 7,200 Sq Ft

  108 Glen St, Natick, MA 01760

  An extraordinary opportunity to experience luxury living at its finest. Beautifully situated on 1.47 acres overlooking the stunning orchards at Lookout Farm in South Natick, this newly-constructed home blends elegant sophistication w/modern functionality. The 1st floor offers a custom chef’s kitchen w/high-end appliances, a sunlit dining area & fireplaced family room - all showcasing the gorgeous

  Beyond Boston Properties Group Compass

  108 Glen St, Natick, MA 01760
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  /18

  $8,999,000

  • Land
  • 1.01 Acres
  • $8,909,901 per Acre

  283 Melrose St, Auburndale, MA 02466

  **Rare By-Right Opportunity** This is a Broker marketed sale by Trustee and authorized by bankruptcy court. Sale by order and Trustee deed but otherwise as is, where is. Will sell with clear title, marketable insurance and free of liens and encumbrances. Stalking Horse bidder will receive overbid protection of up to five (5%) percent. Stalking Horse offers due by May 11, 2026. Set in the heart of

  Ward Shifman Coldwell Banker Realty - Newton

  283 Melrose St, Auburndale, MA 02466
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  /24

  $2,495,000 New Construction

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

  298 Summer St, Westwood, MA 02090

  This sophisticated New England farmhouse is set on Westwood’s iconic Summer Street. Recently completed, it offers 4,700 square feet of living space that blends classic detail with tasteful contemporary design. The gourmet kitchen is a culinary enthusiast’s dream, featuring granite countertops and a substantial island ideal for both preparation and casual dining. It opens to a fireplaced living

  John Boyle LandVest, Inc.

  298 Summer St, Westwood, MA 02090
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  /27

  $2,495,000

  • 3 Beds
  • 3.5 Baths
  • 2,712 Sq Ft

  338 Boylston St Unit C, Newton, MA 02459

  This sun-drenched, contemporary townhome was gut-renovated down to the studs just 21⁄2 years ago, delivering exceptional quality, modern design, and effortless living. The home features 3 spacious bedrooms, 31⁄2 beautifully appointed baths, and an open layout enhanced by custom finishes and top-of-the-line appliances throughout.Designed for both comfort and entertaining, the interiors are filled

  Abby Shapiro MGS Group Real Estate LTD

  338 Boylston St Unit C, Newton, MA 02459
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  /27

  $615,000

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft

  611 Watertown St Unit 14, Newtonville, MA 02460

  Bright and spacious 2-bedroom, 2-bath upper-level condo offering comfortable living in a convenient Newton location. The open-concept living and dining area flows seamlessly to a private balcony—perfect for relaxing or entertaining. Both bedrooms are generously sized with excellent closet space, including a primary suite with its own en-suite bath. Freshly painted with updated lighting, this

  Stephanie Crawford Real Broker MA, LLC

  611 Watertown St Unit 14, Newtonville, MA 02460
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  /42

  $3,200,000

  • 6 Beds
  • 6 Baths
  • 6,200 Sq Ft

  1 Mill St, Dover, MA 02030

  Set on one of Dover's most picturesque country roads along the Charles River, this 6-bedroom, 6-bath Colonial offers 6,200 SF of living space. Sited on 2.37 acres with lush grounds, amazing river views, and direct river access with a private dock. The first floor features a sunroom, spacious living room with fireplace, office w/built-ins and large dining room, all opening to an expansive deck for

  Martha Bohlin Compass

  1 Mill St, Dover, MA 02030
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  /27

  $538,000

  • 1 Bed
  • 1.5 Baths
  • 899 Sq Ft

  250 Hammond Pond Pkwy Unit 1604N, Chestnut Hill, MA 02467

  This sprawling condominium with 16th floor awe-inspiring views is truly a rare find at the Towers of Chestnut Hill. This corner unit showcases wonderful space, light and well-proportioned rooms and expands nearly 1000 sq. ft. and feels even larger. Truly panoramic unobstructed views from every room allow the perfect backdrop for entertaining. From the moment you drive up to the circular drive,

  Richard C. Dore Hammond Residential Real Estate

  250 Hammond Pond Pkwy Unit 1604N, Chestnut Hill, MA 02467
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  /42

  $9,990,000

  • 5 Beds
  • 10 Baths
  • 11,352 Sq Ft

  70 Possum Rd, Weston, MA 02493

  This peerless modern 2-acre estate is located in a highly desired private neighborhood in Weston. Exterior features a beautiful, flat landscaped yard, patio w/grill, and a full sports court. The luxurious 5 bed, 7f/3h bath interior features lofty 12’ high ceilings with walls and ceilings of glass, opening the space to the exterior and drenching this home in sunlight. Smart home features include

  Rose Hall Blue Ocean Realty, LLC

  70 Possum Rd, Weston, MA 02493
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  /30

  $7,495,000

  • 8 Beds
  • 9 Baths
  • 9,662 Sq Ft

  200 Pond Rd, Wellesley, MA 02482

  Presenting a spectacular multi-acre estate set behind a private entry in Wellesley. This stately Georgian Colonial is the centerpiece of the compound on a scenic road and is surrounded by a parklike setting that couples luxury with sophistication. The stately exterior is captivating with stunning architectural detail. Inside the grand home boasts a two story foyer with a sweeping bridal

  Meghan Sutherland MGS Group Real Estate LTD - Wellesley

  200 Pond Rd, Wellesley, MA 02482
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  /22

  $525,000

  • 1 Bed
  • 1 Bath
  • 1,050 Sq Ft

  280 Boylston St Unit 713, Chestnut Hill, MA 02467

  Renovated to perfection, this 1-bedroom, 1 full bath home is completely turn-key and gorgeous! Conveniently located at Imperial Towers in Chestnut Hill, the professionally managed building offers a Concierge, heated seasonal pool, new fitness center, clubroom, library, beautiful lobby, EV charing station, extra storage and on-site management. One deeded parking spot and close to restaurants,

  Betsy Kessler Rutledge Properties

  280 Boylston St Unit 713, Chestnut Hill, MA 02467
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  /30

  $2,800,000

  • 5 Beds
  • 3 Baths
  • 5,328 Sq Ft

  169 Hickory Rd, Weston, MA 02493

  Rarely available, this beautifully updated contemporary home is set on over 1.4 acres in one of Weston’s premier South Side neighborhoods. Bathed in natural light and offering exceptional privacy, the property is surrounded by mature landscaping, gardens, a pool, fieldstone walls, and inviting patios that create a peaceful setting. Thoughtfully renovated with quality finishes throughout, the

  Dean Poritzky Engel & Völkers Wellesley

  169 Hickory Rd, Weston, MA 02493
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  /25

  $1,195,000

  • 4 Beds
  • 2.5 Baths
  • 3,359 Sq Ft

  8 Hobbs Rd, Wayland, MA 01778

  RARE MID-CENTURY MODERN GEM IN WAYLAND’S PREMIER LOKER NEIGHBORHOOD. For the first time ever, this Frank Lloyd Wright-inspired architectural masterpiece is available. Situated on a private 1.09-acre cul-de-sac lot, this sun-drenched 11-room residence offers the perfect blend of vintage character and incredible potential to customize. The flexible floor plan features 4 spacious bedrooms and 2.5

  Nikki Milott McCay Gibson Sotheby's International Realty

  8 Hobbs Rd, Wayland, MA 01778
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  /9

  $799,000

  • 2 Beds
  • 3.5 Baths
  • 1,570 Sq Ft

  33 Cottage St, Newton Upper Falls, MA 02464

  Tucked away on peaceful, landscaped grounds in Newton Upper Falls, this beautiful end-unit townhouse condominium features two bedrooms, three and one-half baths, and a comfortable, convenient layout. The first floor shines with an entry foyer and closet that opens to a spacious living room, which leads to the formal dining room featuring sliding glass doors leading to a full-length rear

  The Kennedy Lynch Team Hammond Residential Real Estate

  33 Cottage St, Newton Upper Falls, MA 02464
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  /5

  $5,000,000

  • Land
  • 7.28 Acres
  • $686,813 per Acre

  216-218 S Main St, Natick, MA 01760

  Presenting The Residences at South Main Street located in Natick, Massachusetts. This 7.28-acre site is approved for 26-unit single family/townhouse development.The property is situated in the vibrant suburban town of Natick, located approximately 15 miles west of downtown Boston. Residents are served by several major highways (I90, Mass Pike, and Route 9) and the Natick MBTA Station which

  Chris Sower Cushman & Wakefield

  216-218 S Main St, Natick, MA 01760
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  /20

  $5,695,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 9,400 Sq Ft

  196 Pond Rd, Wellesley, MA 02482

  Once in a lifetime opportunity to own in Wellesley's most coveted premier historic location, Pond Road. Featuring the finest custom craftsmanship throughout, professionally engineered mechanical systems, smart house and professionally designed ultra high end finishes. Over 9400 sq ft of living space on 3 floors. The floor plan everybody wants with a 1200 sq ft great room and over 10 foot

  Melissa Dailey Coldwell Banker Realty - Wellesley

  196 Pond Rd, Wellesley, MA 02482
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  /38

  $2,199,000

  • 3 Beds
  • 4.5 Baths
  • 4,165 Sq Ft

  62 Claybrook Rd, Dover, MA 02030

  NEW CONSTRUCTION! Top-tier living minutes from shopping, dining, highways, and the commuter rail. Set on a scenic road near Dover town center this stunning home offers over 4,000 sq ft of beautifully finished space with high end designer finishes. The open concept main level features a gracious living room highlighted by a stone fireplace, sun-filled dining area, and a chef’s kitchen with a large

  Denise Mosher Coldwell Banker Realty - Weston

  62 Claybrook Rd, Dover, MA 02030
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  /42

  $2,950,000

  • 4 Beds
  • 3.5 Baths
  • 5,095 Sq Ft

  55 Forest Ridge Rd, Weston, MA 02493

  Turnkey Colonial blending luxury, comfort, and convenience with thoughtfully designed interiors, set on a sought-after cul-de-sac. A grand foyer leads to an updated kitchen featuring quartz countertops, stainless appliances, abundant cabinetry and a large island, opening seamlessly to a family room with soaring ceiling and direct access to an expansive patio. A formal living room with fireplace

  Denise Mosher Coldwell Banker Realty - Weston

  55 Forest Ridge Rd, Weston, MA 02493
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  /36

  $2,590,000

  • 4 Beds
  • 7 Baths
  • 5,181 Sq Ft

  130 Summer St, Weston, MA 02493

  Welcome to stunning customized luxury home. The chef’s kitchen features an oversized center island with seating, Wolf and Sub-Zero appliances, and a custom stone pizza oven. Bar cabinet has built-in sub-zero refrigerator and ice maker. Charming kitchen with french slide doors present you natural light & tree view for all seasons. It seamlessly flows into the dining area and a grand living room

  Soyeon Yang Spark Real Estate

  130 Summer St, Weston, MA 02493
• 

  

  /31

  $3,450,000

  • 4 Beds
  • 4.5 Baths
  • 7,195 Sq Ft

  24 Trailside Rd, Weston, MA 02493

  Experience where nature and tranquility converge. This unique home has direct access to town trails leading to the Weston Reservoir. Its striking stone and wood exterior enhanced by a gorgeous new cedar roof sets the tone for its warm and sophisticated interior. The living room stuns with soaring ceilings, exposed wood beams, and glass doors that open to a stone patio and exquisitely landscaped

  Mizner+ Montero Gibson Sotheby's International Realty

  24 Trailside Rd, Weston, MA 02493

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