Wellesley Hills, MA Homes for Sale with Acreage

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  /14

  $1,250,000

  • 3 Beds
  • 2 Baths
  • 1,567 Sq Ft

  250 Hammond Pond Pkwy Unit 1505N, Chestnut Hill, MA 02467

  Towers of Chestnut Hill, residence 1505N, no expense has been spared to create this sophisticated home. This ultra chic unit is renovated to the highest standard with quality craftmanship throughout. Top of line finishes and thoughtfully designed choices created this perfect condominium. This grand 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 1505N, Chestnut Hill, MA 02467
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  /24

  $2,725,000 New Construction

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

  298 Summer St, Westwood, MA 02090

  This sophisticated New England Farmhouse on Westwood’s iconic Summer Street, just completed, offers classic details integrated with tasteful contemporary design. The well-appointed, eat-in kitchen with west facing windows opens to a deck that overlooks the beautiful two-acre lot. It features granite countertops, high-end appliances and leads to a fireplaced living room and gracious dining room.

  John Boyle LandVest, Inc.

  298 Summer St, Westwood, MA 02090
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  /42

  $3,295,000 Open Sat 12PM - 2PM

  • 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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  /10

  $6,800,000

  • Land
  • 6.88 Acres
  • $988,372 per Acre

  0 Wellesley St, Weston, MA 02493

  Unique opportunity to own a pristine 6.88 acre retreat lot, surrounded partially by conservation land. The property features two parcels of land being sold together. Come walk this stunning property, located south of Rte 20, near historic Chestnut Street. Build your dream estate, 15 miles from Boston, minutes to the highway. Existing 4 bedroom house is likely a tear down. View attached land

  Margaret Rogers Waterfront Realty Group

  0 Wellesley St, Weston, MA 02493
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  /42

  $3,998,000

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

  365 Charles River St, Needham, MA 02492

  Welcome to 365 Charles River Street. Set on an expansive 1+ acre lot, this home is built by Trio Development & captures today's modern living with custom design, expert craftsmanship & luxurious finishes. You are welcomed into this home by a stunning 2 story foyer & open concept floor plan. The gourmet chef's kitchen features stainless appliances, custom cabinetry, large island, butler's pantry &

  Jeff Groper Coldwell Banker Realty - Newton

  365 Charles River St, Needham, MA 02492
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  /27

  $578,000

  • 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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  $7,995,000

  • 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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  /30

  $6,650,000

  • 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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  /36

  $1,699,000 Open Sat 11:30AM - 1PM

  • 3 Beds
  • 5 Baths
  • 4,352 Sq Ft

  211 Eliot St, Natick, MA 01760

  Impeccably maintained luxury ranch in sought-after South Natick - an exceptionally rare offering. This expansive home features generously proportioned rooms, unique character, and a thoughtful layout designed for easy living and seamless flow. The main level includes 3 bedrooms, highlighted by a private primary suite with sitting area, en-suite bath, and large walk-in closet. A sun-filled great

  The Samantha Eisenberg Group Compass

  211 Eliot St, Natick, MA 01760
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  /23

  $5,500,000

  • Land
  • 3.25 Acres
  • $1,692,308 per Acre

  136 Dudley Rd, Newton Center, MA 02459

  Rarely available 3.25-acre property on Newton's South Side offers an exceptional development opportunity in an estate property area. The site is located on picturesque Dudley Road, surrounded by mature trees and expensive homes. There is currently a 4,200sf antique barn on the property that was converted to a residence 50 years ago. This residence has 4 bedrooms, 3 bathrooms and a 2-car garage.

  Ezra Stillman Hammond Residential Real Estate

  136 Dudley Rd, Newton Center, MA 02459
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  /17

  $16,500,000 Pre-Foreclosure

  • Land
  • 1.01 Acres
  • $16,336,634 per Acre

  283 Melrose St, Auburndale, MA 02466

  Set in the heart of Auburndale Village, 283 Melrose Ave offers approximately 43,783 ± sq ft of VC2-zoned land steps to village shops and a short distance to the Commuter Rail. The newly created VC2 district is designed to encourage housing and mixed-use density in Newton’s village centers - making this one of the rare, well-located sites positioned to capitalize on that vision. The property

  Ward Shifman Coldwell Banker Realty - Newton

  283 Melrose St, Auburndale, MA 02466
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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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  /39

  $4,995,000

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

  68 Locust Ln, Needham, MA 02492

  Welcome to the stunning new construction! Located on a private cul-de-sac set on Needham-Wellsley boarder. The grand two-story entrance features an open-concept layout with a living room, formal dining room, home office with a fireplace, guest bedroom, and a chef's kitchen with two islands, a walk-in pantry, and a breakfast/dining area. The side entrance features a beautiful mudroom with lots of

  Alex Kuzakovsky Luna Luxury Realty

  68 Locust Ln, Needham, MA 02492
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  $6,995,000

  • 6 Beds
  • 10 Baths
  • 10,090 Sq Ft

  121 Livingston Rd, Wellesley, MA 02482

  Set on nearly two acres with direct access to the Charles River and surrounded by conservation land, this custom-built Colonial offers a rare combination of privacy, scale, and waterfront living in Wellesley’s coveted Dana Hall neighborhood. Thoughtfully designed and crafted, the home delivers enduring quality and a lifestyle that is increasingly rare.A gracious foyer introduces formal living and

  Ying Sun Compass

  121 Livingston Rd, Wellesley, MA 02482
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  /42

  $4,950,000 Open Thu 10AM - 11:30AM

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

  151 Oakland St, Wellesley Hills, MA 02481

  A rare Wellesley gem set on 1.15 acres, overlooking the 15th hole & 16th tee of Wellesley Country Club 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 great room, sophisticated

  Beth Dickerson Gibson Sotheby's International Realty

  151 Oakland St, Wellesley Hills, MA 02481
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  /42

  $10,950,000

  • 6 Beds
  • 8 Baths
  • 10,845 Sq Ft

  8 Hidden Rd, Weston, MA 02493

  Significant turnkey custom residence in prime Weston Golf Club neighborhood with expansive yard. 6-bedroom shingle-and-stone manor with copper accents and refined finishes, privately set above Hidden Road. Tucked behind mature landscaping, a winding drive leads to a flat motor court with generous parking. Foyer opens to living room with fireplace and backyard access. Dining room served by

  Chaplin Partners Compass

  8 Hidden Rd, Weston, MA 02493
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  /42

  $34,000,000

  • 6 Beds
  • 8 Baths
  • 12,714 Sq Ft

  4 Willow Rd, Weston, MA 02493

  Step into a world of timeless elegance in this iconic English Revival Tudor. Prominently set high on a ridge abutting a tranquil pond and the lands surrounding the Weston Golf Club. The gated entry and winding approach reveal the commanding terraced property comprising over 6 secluded acres. The 1928 estate was originally designed by architect Eric Kibbon. A balance between modern comfort, beauty

  Mizner+ Montero Gibson Sotheby's International Realty

  4 Willow Rd, Weston, MA 02493
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  /27

  $715,000

  • 2 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  6 Steepletree Ln, Wayland, MA 01778

  Stoneridge Village at Mainstone Farm. Highly sought after one floor living offers a king-size primary bedroom suite with walk-in closet plus a rare main floor den and 3 new sliders to a private 23ft grade level deck, nestled on an ended way with leafy nature views. A spacious bright living room has a soaring double height window and fireplace. Updated kitchen with hardwood floors has ample

  Maria Ackmakian REMAX Executive Realty

  6 Steepletree Ln, Wayland, MA 01778
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  $1,279,000 Open Sun 12PM - 1:30PM

  • 2 Beds
  • 3.5 Baths
  • 3,094 Sq Ft

  401 Dedham St Unit B, Newton Center, MA 02459

  One of the area’s most desirable communities-The Gables! This VERSATILE plan adapts beautifully to a variety of lifestyles, whether accommodating family, guests, multigenerational living, or a dedicated work-from-home setup. With 3 fully finished levels, 8 well-proportioned rooms, 3.5 baths & almost 3100 sqft, the options are abundant. A dramatic two-story foyer with an elegant staircase welcomes

  Tracy Reed William Raveis R.E. & Home Services

  401 Dedham St Unit B, Newton Center, MA 02459
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  $4,549,000 Open Sat 11AM - 12:30PM

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

  1266 South St, Needham, MA 02492

  Set on a beautifully landscaped one-acre lot, this exceptional new construction home offers the prestige of a South Street address while enjoying the privacy and tranquility of a side-street orientation. Spanning over 7,000 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, & a working

  Connor Gillen Keller Williams Realty

  1266 South St, Needham, MA 02492
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  $1

  • Land
  • 1.83 Acres
  • $1 per Acre

  02 Wellesley St, Weston, MA 02493

  An exceptional development opportunity on coveted Wellesley Street in Weston. Set on a generous, private lot, this rare offering invites builders, developers, and end-users alike to bring their vision to life in one of the town’s most desirable locations. The property provides an ideal canvas for a custom residence—whether a modern masterpiece or a timeless New England estate—surrounded by

  Maggie Gold Seelig MGS Group Real Estate LTD

  02 Wellesley St, Weston, MA 02493
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  /30

  $7,200,000

  • 99 Beds
  • 198 Baths
  • 16,919 Sq Ft

  21 Eliot St, Natick, MA 01760

  21 Eliot Street presents a unique investment opportunity in the heart of South Natick Center. Spanning 3 acres of beautifully maintained and natural grounds, this large and level property is zoned for both commercial and residential use. Currently hosting four well-preserved buildings featuring a mix of office and retail spaces, it combines functionality with charm. Its excellent condition and

  Prudence Hay Rutledge Properties

  21 Eliot St, Natick, MA 01760
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  /2

  $4,000,000

  • Land
  • 1.31 Acres
  • $3,053,435 per Acre

  74 Rumford Ave, Waltham, MA 02453

  57,255 sf parcel.Walking distance to vibrant Moody Street with retail shops and restaurants • Quiet setting with frontage on Cram’s Cove, an estuary of the Charles River • “Commercial” zone with “Riverfront Overlay” allows a variety of uses, including multifamily, with generous height and FAR allowances

  Ben Silva Acorn Property Management LLC

  74 Rumford Ave, Waltham, MA 02453
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  $759,000

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  280 Boylston St Unit 710, Chestnut Hill, MA 02467

  It's the size! Experience the ease of full-service condominium living in this 1600 sq ft, bright 2-bedroom, 2-bath corner residence at the desirable Imperial Towers in Chestnut Hill. Ideal for downsizers and those seeking a luxurious, full-service lifestyle. Features include high ceilings, abundant natural light & generous closets (2 walk-ins) and engineered hardwood floors. Enjoy the many

  Stig Bergquist Keller Williams Realty

  280 Boylston St Unit 710, Chestnut Hill, MA 02467
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  $7,995,000

  • 6 Beds
  • 8 Baths
  • 8,093 Sq Ft

  222 Grove St, Wellesley, MA 02482

  Discover exceptional elegance & privacy in Wellesley’s coveted Dana Hall neighborhood. Set on over an acre in one of the town’s most sought-after locations it offers the perfect balance of privacy & convenience. Designed by a renowned local architect, this stunning new home blends sophisticated design with modern comfort, creating a serene retreat moments from town. The main floor boasts an open,

  Steve & Nicole Connolly Group Coldwell Banker Realty - Wellesley

  222 Grove St, Wellesley, MA 02482
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  /39

  $31,500,000

  • 6 Beds
  • 12 Baths
  • 21,000 Sq Ft

  180 Ash St, Weston, MA 02493

  This extraordinary estate is set on one of Weston’s most prestigious enclaves and blends grand architecture with modern luxury, impeccable craftsmanship and state of the art systems. High ceilings, intricate moldings, and sun-drenched rooms create an atmosphere of timeless elegance. The main level is designed for both grand entertaining and comfortable living, featuring an expansive chef's

  Maggie Gold Seelig MGS Group Real Estate LTD

  180 Ash St, Weston, MA 02493
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  $4,495,000 Open Sat 11AM - 12PM

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

  1780 Central Ave, Needham, MA 02492

  Experience modern luxury in this newly constructed residence, perfectly situated on an expansive, one acre level lot in a convenient Needham location. Thoughtfully designed with high ceilings, abundant natural light, and refined finishes, this 6 bedroom, 6.5 bath property combines comfortable elegance at every turn and includes a unique attached ADU, with private entry— perfect for

  Beyond Boston Properties Group Compass

  1780 Central Ave, Needham, MA 02492
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  /19

  $589,000 Open Sat 12PM - 1PM

  • 2 Beds
  • 1 Bath
  • 1,024 Sq Ft

  51 Pettee St Unit 11, Newton Upper Falls, MA 02464

  Moments from Hemlock Gorge Reservation and Echo Bridge, this peaceful and serene 2-bedroom condo in the historic Emerson Schoolhouse combines charm with modern convenience. Featuring great ceiling height, elevator, and a coveted corner location, this unit is filled with natural light from amazing oversized windows. The primary bedroom offers a large walk-in closet with direct access to the

  David Gordon Coldwell Banker Realty - Newton

  51 Pettee St Unit 11, Newton Upper Falls, MA 02464
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  /40

  $5,895,000

  • 6 Beds
  • 8 Baths
  • 9,848 Sq Ft

  182 Winding River Rd, Wellesley, MA 02482

  Custom home on the Charles River. Incredible views of the river and conservation land beyond plus a dock for kayaks, paddleboards & small electric boats! 2006 new construction w/over 9000 sq ft of living space on 1.73 acres. Walk into dramatic great room w/ 2 story windows plus one of four fireplaces & custom window seat perfect for entertaining. NEWLY renovated white kitchen w/ center island,

  Melissa Dailey Coldwell Banker Realty - Wellesley

  182 Winding River Rd, Wellesley, MA 02482
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  /41

  $2,499,900

  • 5 Beds
  • 6.5 Baths
  • 5,000 Sq Ft

  6 Briar Ln, Natick, MA 01760

  Majestically set on a 1.5-acre lot at the end of a cul-de-sac near the Natick-Weston line, one of the Natick's most prestigious locations. This exquisite Colonial with 5 bedrooms and 6.5 baths is rich with architectural details and checks every box, offering generous space for multi-generations. Designed for today’s living, it showcases an open floor plan and five en-suite bedrooms, including a

  Janice Burke Gibson Sotheby's International Realty

  6 Briar Ln, Natick, MA 01760
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  /21

  $775,000

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  36 Ober Rd, Newton Center, MA 02459

  Priced to sell! Excellent opportunity to take advantage of this tastefully renovated one floor unit in scenic Oak Hill. 36 Ober boasts an abundance of sunlight through its 17 windows, brand new flooring, and a separate flex space for office use or a guest bedroom. Brand new kitchen appliances, backsplash, counters and cabinetry. Storage in unit and in common areas. Very well managed association

  Matthew Bagnell Coldwell Banker Realty - Milton

  36 Ober Rd, Newton Center, MA 02459
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  /16

  $3,975,000

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

  957 South St, Needham, MA 02492

  AN EXCEPTIONAL OPPORTUNITY IN NEEDHAM! This spectacular brand new construction is nestled on a private acre plus lot, offering over 8000 square feet of luxurious living space on FOUR METICULOUSLY DESIGNED LEVELS! Step inside to discover elegance with six generously sized bedrooms suites. Each room reflects extraordinary design and craftsmanship, featuring detailed fixtures and finishes

  Jill Finkelstein & Associates Compass

  957 South St, Needham, MA 02492
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  $1,225,000 Open Sat 11:30AM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,646 Sq Ft

  104 Glen St, Natick, MA 01760

  Ideally situated in one of Natick’s most desirable neighborhoods, this charming South Natick Cape sits on 1.35 acres of pristine land. Backing up to scenic Lookout Farm and bordering picturesque apple orchards, the property offers a rare blend of privacy and natural beauty. Inside, the home features an open-concept kitchen and family room, highlighted by floor-to-ceiling fireplaces, a cozy dining

  Barber Real Estate Group William Raveis R.E. & Home Services

  104 Glen St, Natick, MA 01760
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  /11

  $399,000 Open Sat 1:30PM - 3PM

  • 1 Bed
  • 1 Bath
  • 712 Sq Ft

  73 Walnut St Unit 6, Newtonville, MA 02460

  Desirable LOCATION for a quiet well maintained middle floor condo with SPACIOUS rooms, good closet space, separate dining room and snack bar also, hardwood floors, stall shower in bathroom and renovated vanity-sink-toilet, clean shared laundry room, deeded parking space N, convenient to Trader Joes, Whole Foods, Star and Stop & Shop, commuter rail to Back Bay and Boston, express and local buses,

  Roberta Landau Coldwell Banker Realty - Newton

  73 Walnut St Unit 6, Newtonville, MA 02460
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  $1,875,000 Open Sat 11:30AM - 1PM

  • 4 Beds
  • 4 Baths
  • 4,100 Sq Ft

  189 Eliot St, Natick, MA 01760

  Classic New England farmhouse charm meets modern luxury in this stunning private retreat in South Natick. This beautiful home features 4+ bedrooms, 2 full, 2 half baths, and a thoughtfully designed layout ideal for both functional living with epic entertaining. Elevate every meal in this chef’s kitchen with Sub-Zero refrigerator, Wolf range, seating for 6 at the oversized island opens up to a

  Christine Norcross William Raveis R.E. & Home Services

  189 Eliot St, Natick, MA 01760
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  /38

  $29,000,000

  • 6 Beds
  • 8 Baths
  • 17,067 Sq Ft

  9 Atlas Ln, Weston, MA 02493

  Introducing this Frank Llyod Wright inspired one-of-a-kind gem designed by award winning AD 100 architect, Thomas Catalano. Ultimate privacy on a 6+ acre property, adjacent to the Weston Reservoir, this estate cultivates the symmetry of nature with meticulously curated interiors. Galvanized steel finishes fuse the interior rooms with the exterior heated courtyards. Each space pays homage to its

  Mizner+ Montero Gibson Sotheby's International Realty

  9 Atlas Ln, Weston, MA 02493
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  /42

  $3,195,000

  • 6 Beds
  • 6.5 Baths
  • 7,083 Sq Ft

  19 Old Connecticut Path, Wayland, MA 01778

  Discover a balance of sophistication, comfort, and modern design in this exquisite 7,000+ square-foot modern farmhouse set on over 1 acre of serene land.Thoughtfully crafted across four levels, this home blends exceptional craftsmanship with smart-home innovation. Expansive windows bathe every room in natural light, highlighting a seamless open-concept layout designed for both family living &

  Laurie Henighan Barber Real Estate

  19 Old Connecticut Path, Wayland, MA 01778
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  /18

  $699,000

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

  250 Hammond Pond Pkwy Unit 615N, Chestnut Hill, MA 02467

  This sprawling condominium with southwest exposure and beautiful views is truly a rare find at the Towers of Chestnut Hill. This corner unit showcases tremendous space, light and well-proportioned rooms and expands nearly 1,300 sq. ft. and feels even larger. This home allows the perfect backdrop for entertaining. From the moment you drive up to the circular drive, the Towers offers the ultimate

  Richard C. Dore Hammond Residential Real Estate

  250 Hammond Pond Pkwy Unit 615N, Chestnut Hill, MA 02467
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  /2

  $1

  • Land
  • 1.77 Acres
  • $1 per Acre

  0 Wellesley St, Weston, MA 02493

  An exceptional development opportunity on coveted Wellesley Street in Weston. Set on a generous, private lot, this rare offering invites builders, developers, and end-users alike to bring their vision to life in one of the town’s most desirable locations. The property provides an ideal canvas for a custom residence—whether a modern masterpiece or a timeless New England estate—surrounded by

  Maggie Gold Seelig MGS Group Real Estate LTD

  0 Wellesley St, Weston, MA 02493
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  /39

  $1,999,998 Open Sat 12:30PM - 2PM

  • 4 Beds
  • 5 Baths
  • 4,041 Sq Ft

  620 South Ave, Weston, MA 02493

  Significantly renovated and masterfully reimagined, this stunning contemporary home impresses! Privately set on 2.61 acres, a dramatic foyer welcomes you with soaring ceilings, crisp white finishes, and walls of glass that bathe every space in natural light. Designed for modern living and effortless entertaining, the open floor plan showcases a spectacular vaulted living room and state-of-the-art

  Denise Mosher Coldwell Banker Realty - Weston

  620 South Ave, Weston, MA 02493

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