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$5,695,000
5 Beds ⋅ 7 Baths ⋅ 73499334 MLS
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 ceilings. Oversized mudroom and pantry. First floor includes white oak herring bone hardwoods. 2nd floor ceilings 14-20 feet! An incredible main suite. All bedrooms en-suite with walk-in closets. Plus a 2nd floor lounge room or incredible guest suite. Lower level is unprecedented with 17 ft ceiling in 1/2 court basketball/ rec room (size of space also work for squash) with viewing room including wet bar. Theatre/media room with additional wet bar plus a gym with full bath including steam shower. Large flat yard. Close to Wellesley trails and town center.

196 Pond Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.
$5,650,000
6 Beds ⋅ 6 Baths ⋅ 73528133 MLS
Located within coveted Salten Point, this custom home captures sweeping views of Barnstable Harbor and Sandy Neck Beach. The open floor plan features mahogany millwork, walls of windows, and a living room with a grand stone fireplace and den. A chef’s kitchen boasts a marble island, Sub-Zero/Wolf appliances, and access to a screened-in dining porch. Outdoor amenities include a covered deck, pool, outdoor kitchen, and fire pit. An en suite guest bedroom completes the main level. Upstairs, the primary suite offers a private balcony, fireplace, and luxury bath with a soaking tub and walk-in shower, alongside three additional bedrooms (one en suite, two sharing a Jack-and-Jill bath). The lower level features built-in bunks, a TV area, and a fitness room. Equipped with a 2-car garage, top-of-the-line HVAC with air purification and dehumidification, and town sewer, the property includes deeded water access for swimming and kayaking, and is walking distance to Barnstable Village.

22 Kent Road, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .
$5,650,000
7 Beds ⋅ 9 Baths ⋅ 73493729 MLS
Stunning waterfront home in Squantum with sweeping ocean views from nearly every room. Defined by its nautical charm and breathtaking waterfront setting, this exceptional residence offers 7 bedrooms, 7 full baths, 2 half baths, a private office, media room, and a 3-car garage. Sun-filled living spaces, soaring ceilings, warm wood floors, and a custom kitchen with sleek cabinetry and high-end appliances create a perfect blend of comfort and luxury. Set directly on the water in Quincy’s premier coastal neighborhood, just moments from marinas, beaches, waterfront walks, and with easy access to Boston.

156 Crabtree, Quincy

Listing courtesy of Listing Agent: Joe Karam from Listing Office: Northeast Development & Investment, Inc..
$5,627,000
9 Beds ⋅ 6 Baths ⋅ 73469901 MLS
Once-in-a-lifetime opportunity in Olde Chestnut Hill - this grand turn of the century victorian home is situated on almost 1 acre and offers mature trees and plantings, a large private back yard, and a separate 2+ car barn. Walking distance to many area amenities and public transportation, this elegant home is perfectly sighted away from the street and offers supreme privacy. Many restored historical details include a formal foyer with grand staircase, multiple fireplaces, and reclaimed hardwood flooring. Flooded with natural light this gracious home offers a large eat-in kitchen that overlooks the back yard, a banquet sized formal dining room, and a double parlor that is ideal for entertaining. The second floor of the home is complete with 4+ bedrooms, including a bright primary bedroom with en suite bath and study. The top floor boasts 3+ bedroom, large laundry room. Abundant storage throughout, partially finished basement, plus an outdoor covered loggia in the heart of Chestnut Hill

394 Hammond St, Newton

Listing courtesy of Listing Agent: Michael Harper from Listing Office: Coldwell Banker Realty - Boston.
$5,595,000
6 Beds ⋅ 7 Baths ⋅ 73571648 MLS
Presenting this exemplary redesign of classic shingle-style architecture on the crest of Nashawtuc Hill. This spectacular 6+ bedroom home w/ 1 BR/1ba carriage house sits on 1.2 acres with a level yard, terraced gardens and field. Peaceful & private with views for miles. Originally designed by award-winning local architect then updated 2026 by premier local builder, exhibiting top-tier materials, superior design and impeccable condition throughout. Off the quiet Common, the driveway flanked by stone pillars and walls leads to a welcoming, landscaped entrance. Updated bathrooms throughout, brand new kitchen with center island, high-end appliances, sunny breakfast area, butler’s pantry, and bar. Spacious primary suite with stunning bath and dual walk-in closets. Architectural details at every turn including custom built-in bookshelves, arched doorways, solid core doors and upgraded millwork. Oversize windows, a screen porch and French doors leading out to both patio and garden areas, abundant sunshine and connection to outdoors. Heating and cooling systems thoughtfully engineered for efficiency and comfort . Elevator. 3-car garage. Proximity to train, town center shopping, trails, & river access.

49 Willard Common, Concord

Listing courtesy of Listing Agent: Abby & Emmy White Team from Listing Office: LandVest, Inc., Concord.
$5,500,000
7 Beds ⋅ 8 Baths ⋅ 73574029 MLS
Exceptional space. Endless flexibility. Designed for the way families live today. Set on a private .73-acre lot in one of Lexington’s most coveted neighborhoods, this remarkable estate offers over 10,500 SF of thoughtfully designed living space w/ 7 beds & 7.5 baths, and a set of amenities that include a private home office, custom theater, game rooms, gym, sauna, yoga room, pet washing station, heated pool, full outdoor kitchen, fire pit lounge & basketball court. An ideal opportunity for multigenerational living, the home provides the space & flexibility to accommodate extended family, adult children, an au pair or long-term guests allowing everyone to live together while maintaining privacy & independence. A dramatic two-story foyer w/ arched windows opens to formal living & dining rooms and an expansive open-concept kitchen/family room w/ oversized center island & professional-grade appliances. The luxurious primary suite features a marble bath, soaking tub, oversized shower & boutique-style dressing room w/ changing area and dedicated shoe & accessory closets. Multiple living & recreation spaces throughout the home create endless possibilities for separate family areas, work-from-home spaces & private retreats. Additional features include expansive stone patios & mature fenced grounds. A mudroom w/ built-ins & attached 3-car garage complete a truly versatile home designed to bring generations together without sacrificing space, comfort or privacy.

28 Tyler Rd, Lexington

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.
$5,500,000
6 Beds ⋅ 7 Baths ⋅ 73534168 MLS
Elevated elegance awaits you at this new construction gambrel home with opportunity to customize. Over 7,400sqft of finished space on expansive 16.6k level lot which includes a separate cabana/lounge and office. The chef's kitchen featuring top of the line appliances, custom cabinetry, oversized island and walk in pantry. The second level has 4 ensuite bedrooms and baths. The primary bedroom has a spa bathroom with soaking tub and walk in closet. The lower level features a sitting area with a wet bar, bedroom and bonus spaces perfect for a movie theater, gym and wellness room. Leveled back yard with covered deck and built-in speakers perfect for outdoor gatherings. Perfectly located facing the park and short distance to middle schools and high school.

62 Country Club Rd, Newton

Listing courtesy of Listing Agent: Stephanie Lau from Listing Office: Bellafi Real Estate, Inc..
$5,499,900
6 Beds ⋅ 8 Baths ⋅ 73555787 MLS
Introducing an extraordinary luxury estate to be constructed in Dedham’s prestigious Precinct One. Conceived as the signature residence within this exclusive offering, this exceptional home will showcase timeless architecture, expansive living spaces, and the highest level of craftsmanship. Planned to offer approximately 5,500–7,000 square feet of thoughtfully designed living space, the residence will feature grand entertaining areas, a designer kitchen, luxurious primary suite, private office, wellness and recreation spaces, and seamless indoor-outdoor living. Early purchasers may have the opportunity to personalize select finishes and design elements. Ideally located moments from Legacy Place, Dedham Country & Polo Club, private schools, commuter routes, and downtown Boston. Renderings are conceptual. Final plans, specifications, features, pricing, and finishes are subject to builder and purchaser selections.

265 Meadowbrook Road, Dedham

Listing courtesy of Listing Agent: Michael Musto from Listing Office: RE/MAX Distinct Advantage.
$5,499,900
5 Beds ⋅ 7 Baths ⋅ 73552370 MLS
Experience Newburyport’s most coveted waterfront lifestyles at Bartley’s Landing.By purchasing your home lot for $1,750,000 & engaging in a construction contract you will join an exclusive enclave of just 5 luxury residences along the Merrimack River.This exceptional new construction opportunity pairs timeless architecture, superior craftsmanship & thoughtful design with the ability to personalize your dream home alongside one of the area’s premier designer and construction teams.Enjoy year-round river activity where boats glide by, migratory birds gather, fish occasionally break the surface and the changing seasons create an ever-evolving backdrop.Owners enjoy access to the community boathouse and private dock, with slip space for boats up to 35 feet - making days on the water effortless.Rarely does a property come on the market combining exclusivity and connection to the river.Bartley’s Landing is year round luxury waterfront living at one of Newburyport’s most prestigious addresses.

570 Merrimac St, Newburyport

Listing courtesy of Listing Agent: Homes & Lifestyles Team from Listing Office: Gibson Sotheby's International Realty.
$5,499,000
4 Beds ⋅ 6 Baths ⋅ 73469087 MLS
Newly Refined with an Updated Design.Spectacular new construction in coveted World’s End by acclaimed design-build team White Oak Home and The Kerr Collective. This coastal residence offers the opportunity to personalize a thoughtfully designed custom home with harbor views and a private setting. Features include a dramatic great room with soaring ceilings, gas fireplace, and French doors to a rear patio for seamless indoor-outdoor living. The chef’s kitchen offers premium appliances, a 10-ft island, separate scullery, and elegant dining room with expansive windows. The first floor includes a bonus room with full bath, formal living room, and office. The second level features a luxurious primary suite with balcony and spa-style bath, three additional bedrooms, family room, and two full baths. Enjoy a 3-car garage, deeded beach rights, and a location steps to World’s End, minutes to Boston.

112 Martins Ln, Hingham

Listing courtesy of Listing Agent: Darleen Lannon from Listing Office: William Raveis R.E. & Home Services.
$5,497,000
5 Beds ⋅ 7 Baths ⋅ 73509134 MLS
Exceptional Luxury Living in Wellesley’s Generals Neighborhood. A rare opportunity for luxury buyers seeking exceptional craftsmanship, modern amenities, and a premier Wellesley location. Custom built in 2017, this 6,300+ SF Neoclassical Colonial in Wellesley’s coveted Generals neighborhood offers four elevator-served levels designed for sophisticated everyday living and effortless entertaining.Whole-house radiant heat, grain-matched white oak floors, bespoke millwork, and 9-foot ceilings—including the finished lower level—reflect a standard of construction rarely found. The chef’s kitchen features soapstone countertops, dual dishwashers, and a walk-in pantry, while five en-suite bedrooms provide exceptional privacy. The primary suite offers a spa-inspired bath and a serene retreat from the day.The lower level transforms into a destination of its own with a private executive office, home gym, wine storage, and Bowers & Wilkins Diamond cinema. Outdoors, enjoy a custom patio, fireplace, hot tub, and mature arborvitae creating a private setting for entertaining and relaxation. A two-car garage and dual EV chargers add everyday convenience.An exceptional choice for those relocating to Wellesley or moving up within town, with Morses Pond, Hardy Elementary, Linden Square, Wellesley Square, shopping, dining, and commuter rail all nearby.For buyers searching for a move-in-ready luxury home in Wellesley, 48 Marshall Road offers the rare combination of quality, location, privacy, and amenities that is difficult to replicate. Schedule your private tour today.

48 Marshall Rd, Wellesley

Listing courtesy of Listing Agent: Team Coyle from Listing Office: Compass.
$5,495,000
4 Beds ⋅ 5 Baths ⋅ 73526293 MLS
Set on 15.7 acres in the heart of Sherborn, The Grout Farm offers a rare blend of refined country living and thoughtfully developed equestrian amenities. The reimagined main residence features light-filled living spaces, a custom kitchen, updated systems, and warm modern finishes. The estate includes a detached 1-bedroom, 1-bath guest cottage, carriage barn connected to the main barn, and the Apple Barn with gym, storage, and flexible space designed for future equestrian use. Amenities include a large indoor arena, outdoor arena with specialized footing, drainage, and irrigation, 11 stalls, fenced paddocks, run-in sheds, automatic field waterers, and hacking paths throughout the property. Orchard, greenhouse, gardens, and open pasture complete this distinctive offering within one of New England’s most established equestrian communities, with exceptional access to Boston.

42 Washington St, Sherborn

Listing courtesy of Listing Agent: J. Stanley Edwards from Listing Office: LandVest, Inc., Concord.
$5,495,000
4 Beds ⋅ 7 Baths ⋅ 73511241 MLS
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 sweeping views of the magnificent rolling grounds while overlooking the open floor plan of the main entertainment level The bright and spacious kitchen with a prep pantry and breakfast room lead to the outside patios. The primary suite is adorned with a beautiful wood beamed ceiling and brick fireplace. Dual spa-like bathrooms are complemented by dual walk in closets. 3 en-suite bedrooms are situated in their own private enclaves. The lower level features a fabulous playroom, traditional media room and a brick wine cellar. Stone walls, a receiving court and 4 car garage complete this special home

44 Meadowbrook Road, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.
$5,495,000
6 Beds ⋅ 6 Baths ⋅ 73499732 MLS
Set on a private lane within a five-home enclave, this 10,000+ SF estate is bordered by 7,000 acres of protected land in the Blue Hills Reservation, offering a level of privacy rarely found this close to Boston. Accessed by a stone bridge, the home unfolds across 20 thoughtfully designed rooms with 6 bedrooms and 6 bathrooms. A grand foyer leads to vaulted ceilings, a paneled library with fireplace, multiple living and recreation spaces, a home gym, and a dedicated home theater. The kitchen, equipped with premium appliances, opens seamlessly to a large family room anchored by a floor-to-ceiling stone fireplace. The primary suite features a five-piece bath, steam shower, and multiple walk-in closets. Set on 4+ acres, the grounds include a stone terrace with outdoor kitchen, fireplace, jacuzzi, and mature landscaping. A heated four-car garage, dual driveways, and circular motor court complete the offering. Not just a Milton home; an estate with a Milton address.

3 Stone Bridge Lane, Milton

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.
$5,495,000
2 Beds ⋅ 3 Baths ⋅ 73419421 MLS
Experience a rare opportunity to own a prime waterfront property in one of Chatham's most sought-after locations. Set on 1.44 acres, this beautifully crafted 2-bedroom, 2.5 bath home offers 1,850 sq ft of refined living space w/commanding panoramic views stretching across Oyster Pond, Oyster River & to Nantucket Sound. This exceptional offering includes a conceptual site plan & video for a future 4-bedroom main house w/swimming pool, allowing you to envision the next chapter of luxury living on Cape Cod. Whether you're looking to enjoy the existing home w/separate post & beam garage w/power & water, or build your dream estate, the possibilities are truly remarkable. Additional to the expansive waterfront, this property boasts access to an adjacent cove down a winding 10-foot path. The current home features wood floors, a 2-car garage, office & generous outdoor living areas. An expansive deck provides the perfect vantage point to take in the ever-changing coastal scenery & sea breezes.

99 Uncle Alberts Drive Ext, Chatham

Listing courtesy of Listing Agent: Shane Masaschi from Listing Office: Compass.
$5,495,000
4 Beds ⋅ 4 Baths ⋅ 73391055 MLS
Development opportunities! Welcome to your private sanctuary—a breathtaking 5,898 sq. ft. custom contemporary estate nestled on a secluded 13.18-acre compound. In addition to the primary 4-acre lot, the property includes three additional parcels totaling 9.18 acres, offering unmatched privacy, expansion potential, or conservation opportunities. Designed with meticulous attention to detail, this four-bedroom, four-bathroom masterpiece seamlessly blends luxury and comfort. Exquisite custom stonework graces the interior and exterior, lending timeless elegance to the home’s modern aesthetic.Professionally landscaped grounds create a serene outdoor retreat, harmonizing architecture with nature. A spacious three-car garage offers ample storage and convenience, complementing the home’s thoughtful design. Whether hosting grand gatherings or enjoying the tranquility of its surroundings, this exceptional estate offers an unparalleled lifestyle in an extraordinary setting.

32-70 Lazell Street, Hingham

Listing courtesy of Listing Agent: Ashley Brennan from Listing Office: Gibson Sotheby's International Realty.
$5,490,000
4 Beds ⋅ 5 Baths ⋅ 73579376 MLS
An extraordinary custom built coastal estate beautifully positioned in one of New Seabury’s most coveted settings with sweeping panoramic views of Nantucket Sound. Offering approximately 6000 sq. Ft. is sophisticated enjoyment across 3 levels of comfortable living! The 4 BR/4.5 bath residence embodies the finest in Cape Cod relaxed seaside living. Supersized open kitchen, open to DR and family room. A spacious first floor Primary bedroom with custom double vanity bath, large step in tiled shower. Walk in closet. 2 additional bedrooms all with private baths and walk in closets, A 2 nd primary BR with oversized walk in closet and huge bath w/dble vanity and super sized tiled shower. 2nd and 3rd flr. Entertainment rooms with deck and fabulous views!

53 Triton Way, Mashpee

Listing courtesy of Listing Agent: Priscilla Stolba from Listing Office: Priscilla Stolba RE.
$5,490,000
4 Beds ⋅ 6 Baths ⋅ 73565201 MLS
Perched above Tiverton's coastline with sweeping views out to Fogland Beach, 10 High Hill Road is a newly built luxury home built by Hill and Harbor Design. This retreat spanning just over 5,000 square feet across a thoughtfully designed main residence and detached ADU. The 4-bedroom, 4.5-bath home showcases quality craftsmanship at every turn, with European white oak engineered flooring throughout and a chef's kitchen anchored by a Thermador appliance suite including a 48" gas range, panel-ready appliances, and a walnut island beneath waterfall quartzite countertops. The primary suite offers a spa-like marble bath with quartzite waterfall counters, a custom California Closets system, and Newport Brass fixtures. A coffered great room ceiling wrapped in natural grasscloth wallpaper anchors the main living space, warmed by a gas fireplace with a custom quartzite surround. Outside, a resort-style pool and outdoor shower are framed by professionally designed landscaping. Windows frame the water views from nearly every room, while a fully equipped one-bedroom ADU offers flexible space for guests, extended family, or a private studio. Premium finishes carry through every detail. Deeded mooring coveys with the property. Within walking distance to Fogland beach, restaurants, farm stands — making 10 High Hill Road coastal Rhode Island living at its finest.

10 High Hill Road, Tiverton

Listing courtesy of Listing Agent: Duckworth Prentice Group from Listing Office: Serhant.
$5,475,000
4 Beds ⋅ 6 Baths ⋅ 73387997 MLS
WORLD-CLASS BOSTON ARCHITECT designs a spectacular home incorporating the historic GREENOUGH BARN! 5,418 s.f. Of living space plus a 915 s.f heated and cooled garage/workshop designed for 3 car lifts/6 car storage! The barn frame was relocated from Carlisle conservation land! The barn was reimagined and will be reconstructed as a MODERN MASTERPIECE on one of the most dramatic lots ever offered for any Concord new construction. Surrounded on 3 SIDES BY CONCORD CONSERVATION LAND that is farmed for sunflower fields. Beyond the conservation land are open & UNDISTURBED VIEWS OF MINUTEMAN NATIONAL PARK in every direction. The main living space soars with 30'+ CEILINGS & MASSIVE GLASS WALLS. All 4 bedrooms are on the 1st floor of this one-of-a-kind home. 2nd floor features a media room & private home office. The house offers a 3 car garage significant enough for multiple car lifts. There is no comparable new home currently being built in Greater Boston! The lower level could be utilized for a playroom or additional recreation area. Designed to ENJOY THE LARGE SKY & SPECTACULAR SUNSET VIEWS! Rare Opportunity - permit approved!

241 Shadyside Avenue, Concord

Listing courtesy of Listing Agent: The Zur Attias Team from Listing Office: The Attias Group, LLC.
$5,395,000
6 Beds ⋅ 8 Baths ⋅ 73572478 MLS
Set on a private road at the end of a quiet cul de sac, 50 Willard offers exceptional privacy on 1.3 acres in one of Weston’s most desirable settings. This newly constructed 8,300+ sq ft home was designed for modern family living, with a light filled open floor plan, elegant family room, chef’s kitchen with oversized quartz waterfall island, breakfast area, butler’s pantry and wet bar. Four ensuite bedrooms upstairs include a serene primary suite with spa inspired bath and expansive walk in closet. The finished lower level features a gym, sauna, wine room, wet bar, theater and au pair suite. Beautifully landscaped grounds, generous patios and a three car garage create the perfect setting for entertaining, relaxing and family life. Just moments from Weston’s highly regarded schools, golf courses and walking trails, this 6 bed, 6.5 bath home combines new construction luxury with estate like privacy and easy access to Boston.

50 Willard, Weston

Listing courtesy of Listing Agent: Yassien Youssef from Listing Office: Compass.
$5,390,000
5 Beds ⋅ 6 Baths ⋅ 73507096 MLS
A rare opportunity on Cohasset Harbor now offered at a compelling new price. This stunning shingle-style estate offers extraordinary privacy on elevated land surrounded by 20 acres of salt marsh & woodland with sweeping harbor views. Meandering boardwalks lead to small islands, including one with a tidal dock for direct water access. Designed by Sally Weston & fully renovated, the home blends timeless architecture with modern comfort. A dramatic 2 story foyer opens to formal living & dining rooms each with fireplaces. The kitchen features a large island, baking room & banquette seating, flowing into a family room & sunroom filled with natural light. First-floor spaces include a unique octagonal bedroom, mudroom & potting kitchen. Upstairs the primary suite offers a private sitting area & a spa-like bath, alongside 3 bedrooms, a loft office & a deck overlooking the harbor. 3rd floor suite adds more living space with an additional full bath and room for guests or playroom. Amenities include tennis & bocce courts plus a three story barn perfect for boat storage, a car collection, indoor sports court or artist studio. Third floor of barn features a spacious totally renovated 4 room apartment perfect for generational living. Not in flood zone.

1-R Baileys Island Rd, Scituate

Listing courtesy of Listing Agent: Christine Powers from Listing Office: Coldwell Banker Realty - Cohasset.
$5,350,000
5 Beds ⋅ 8 Baths ⋅ 73573262 MLS
Set within Wellesley’s coveted Dana Hall neighborhood, this exceptional Colonial has been transformed into a secluded retreat where architecture, craftsmanship, and livability come together beautifully. Renovated by Flavin Architects and Ken Vona Construction, the home showcases an exacting level of design and detail. A gracious two-story foyer introduces interiors filled with natural light, while quarter-sawn oak floors lead to the formal dining room, where floor-to-ceiling windows and glass doors open to a secluded patio. A bright solarium and inviting screened-in porch offer additional spaces to unwind and take in the surrounding landscape.At the heart of the home, the Bulthaup kitchen features premium appliances, a butler’s pantry, double ovens, a full-size wine cooler, and an expansive island that flows into the family room with vaulted ceilings, custom built-ins, and a stone gas fireplace. Five bedrooms and six full baths include a serene primary suite with soaring ceilings, a spa-inspired bath, and a private balcony overlooking the grounds. The finished lower level provides a gym, playroom, wet bar, wine cellar, media room, full bath, and entertainment area. Meticulously landscaped grounds complete this distinctive residence, offering an extraordinary setting for both everyday living and entertaining.

55 Ridge Hill Farm Rd, Wellesley

Listing courtesy of Listing Agent: Debi Benoit from Listing Office: William Raveis R.E. & Home Services.
$5,300,000
6 Beds ⋅ 4 Baths ⋅ 73529550 MLS
Discover oceanfront quintessential island living in this newer constructed shingle style home, thoughtfully designed from the ground up to honor the storied architectural heritage of the New England coast while delivering every comfort the modern household demands. From the moment you arrive, the home's classic cedar-shingled façade and welcoming front porch communicate a sense of permanence and grace. It is a home that feels as though it has always belonged on this stretch of Plum Island shoreline. This home offers the most spectacular sunrises and sunsets. Waterviews are admired from every room. Every room tells the same story, thoughtful design, premium craft, and an abiding respect for the islands setting that surrounds it. The front and primary porches offer up a place for morning coffee, afternoon reading, and the simple pleasure of watching the world drift by at an island pace. Plum Island and this home is not just an address, it is a way of living a lifestyle.

4 35th St, Newbury

Listing courtesy of Listing Agent: Kristin Francoeur from Listing Office: Gibson Sotheby's International Realty.
$5,300,000
5 Beds ⋅ 4 Baths ⋅ 73493300 MLS
This historically significant townhouse was built in the Greek Revival style in 1834 by Asher Benjamin. The house was owned by Benjamin’s heirs until 1925 and was rented to the family of the well known landscape architect Arthur Shurcliff for many years. The home has five bedrooms, a beautiful living room with floor to ceiling windows and great light, a formal dining room, a deck, and a spacious kitchen looking out on a small garden. The home has had a number of updates over the years, including the addition of an exterior iron balcony. A lovely wide staircase winds through the lower four floors. This gem is one of the prettiest houses on Beacon Hill.

9 West Cedar St, Boston

Listing courtesy of Listing Agent: Sally T. Brewster from Listing Office: Brewster & Berkowitz R. E..
$5,295,000
4 Beds ⋅ 5 Baths ⋅ 73473408 MLS
Extraordinary and rarely offered, this private estate in the heart of historic Sandwich commands sweeping, panoramic views of Cape Cod Bay from nearly 19 acres of secluded land. A true legacy property, the setting offers unmatched privacy, rolling grounds, and endless possibilities in one of Cape Cod’s most coveted locations. The residence encompasses over 6,000 square feet and is designed to support both refined living and grand-scale entertaining, whether enjoyed as a seasonal retreat or year-round residence. Outdoor living is paramount, with a heated gunite pool, classic farmer’s porch, and widow’s walk serving as exceptional vantage points to take in the ever-changing bay views and coastal horizon. The property also features its own dedicated solar field, enhancing efficiency and sustainability. Rarely does an estate of this magnitude, acreage, and outlook become available—an exceptional opportunity to own a private sanctuary defined by space, serenity, and breathtaking water views

19 Cedarville Road, Sandwich

Listing courtesy of Listing Agent: Ashley Brennan from Listing Office: Gibson Sotheby's International Realty.
$5,250,000
4 Beds ⋅ 5 Baths ⋅ 73571701 MLS
Brand-new and sun-filled, this exceptional shingle-style Gambrel is privately set on nearly an acre of professionally landscaped, level grounds just off coveted Shore Road, less than a block from the ocean. A refined coastal retreat, the 4-bedroom, 4.5-bath residence pairs exceptional craftsmanship with effortless luxury and gracious indoor-outdoor living. Beautiful millwork and 9' ceilings define the first floor, anchored by a vaulted beam-ceiling primary suite with a spectacular spa-inspired bath. The generous eat-in kitchen and family room feature a dramatic shiplap-vaulted ceiling and open to a sun-drenched patio surrounding a heated plunge pool and oversize yard with unlimited potential. A second-floor deck overlooks the secluded grounds, while an additional primary en-suite and two bedrooms and two more baths complete the upper level. Stroll to Chatham Bars Inn, the Fish Pier and Main Street - an enviable setting where the best of Chatham is truly at your doorstep.

106 Barcliff Ave, Chatham

Listing courtesy of Listing Agent: Jill Boudreau from Listing Office: eXp Realty LLC - Corporate Office.
$5,225,000
6 Beds ⋅ 4 Baths ⋅ 73472922 MLS
Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor shower, parking, and mini-split climate control; its upstairs bedroom enjoys views from Farm Pond to Nantucket Sound. Completing the property is the charming Lilac House, a fun open-concept bunk house with a full bath, water-view deck, and private outdoor shower. A wraparound porch captures sweeping ocean views, while beaches, shops, restaurants, Circuit Avenue, and the Harbor are moments away. An established rental history further enhances this rare opportunity in one of Oak Bluffs’ most iconic locations.

4 Canonicus Ave, Oak Bluffs

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$5,200,000
5 Beds ⋅ 4 Baths ⋅ 73534187 MLS
Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.

49 Gosnolds Way, Chilmark

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.
$5,100,000
5 Beds ⋅ 4 Baths ⋅ 73578429 MLS
Welcome to 97 Oakmont, an extraordinary Montana-built log cabin retreat set on 80 private acres in Westminster. Combining exceptional craftsmanship, natural beauty, and unmatched privacy, this is the kind of property that rarely comes to market. The 5+ bedroom home showcases soaring log timbers, a dramatic fireplace, warm wood interiors, and expansive decks designed to take full advantage of the stunning surroundings. Nearly every room offers a view, including the beautifully positioned kitchen boasting Dakota mahogany granite countertops, overlooking the fields, meadows, and rolling landscape beyond. A second-floor office with water views provides a peaceful place to work, create, or simply enjoy the quiet. Outside, the property is just as impressive. Enjoy direct access to Croker Pond with your own private dock and views of the pond's two islands. Whether you're kayaking, fishing, paddleboarding, or simply enjoying a morning coffee by the water, the setting is nothing short of spectacular. The 80 acres offer a rare mix of open meadows, mature woods, and established trails for walking, hiking, exploring, and enjoying nature right outside your door. Organic fields free of chemical fertilizers, abundant wildlife, and a mature maple grove with maple syrup production potential create a property that feels both private and purposeful. The finished walk-out lower level includes a separate living area with direct access to a covered patio, creating a seamless connection to the outdoors and offering some of the property's most beautiful views. The lower garage allows you to park your snow mobile at the end of the day. While the setting feels worlds away, you're just minutes from everything Westminster has to offer, including local restaurants, shopping, Wachusett Mountain, golf, and year-round outdoor recreation. Route 2 and the Fitchburg commuter rail provide convenient access to Boston and surrounding communities.97 Oakmont is more than a home—it's a private New England estate offering waterfront living, extensive acreage, recreational opportunities, and the kind of peace and tranquility that is increasingly difficult to find. A truly rare opportunity.

97 Oakmont Ave, Westminster

Listing courtesy of Listing Agent: The Edwards Realty Team from Listing Office: Barrett Sotheby's International Realty.
$5,100,000
3 Beds ⋅ 7 Baths ⋅ 73511019 MLS
Situated on a lovely street, this very special five story townhome has it all. There are three plus bedrooms with potential for more as the top floor with an open floor plan and sunny balcony offers great flexibility. Wonderful entertaining space and formal rooms with beautiful proportions and architectural details add to the charm. A door from the living room opens out to an extraordinary deck with a balustrade. The bright, eat-in kitchen with large windows looks out on the inviting garden. Amenities include a finished basement with a garden room and lots of storage.

52 Pinckney St, Boston

Listing courtesy of Listing Agent: Sally T. Brewster from Listing Office: Brewster & Berkowitz R. E..

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