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$4,725,000
3 Beds ⋅ 5 Baths ⋅ 73564664 MLS
Set amongst beautifully landscaped grounds and vibrant gardens, this inviting Chappaquiddick retreat offers a wonderful sense of privacy and tranquility. Stunning hydrangeas frame the property, also complemented by mature trees, colorful blooms, and established gardens, creating a beautiful setting throughout the seasons. Multiple outdoor spaces invite relaxing and entertaining, with a heated saltwater pool, completed in 2025, serving as the centerpiece. Inside, warm and inviting living spaces are filled with natural light, while shiplap details and a relaxed coastal aesthetic give the home a classic island feel. Vaulted ceilings and thoughtful attention to detail enhance the home’s comfortable, refined character, while a thoughtfully designed single-level layout offers the ease and convenience of true first-floor living, with a private primary suite and separate guest wing providing an ideal sense of space and privacy. The detached studio with workshop is a hobbyist’s dream, overlooking the pool and offering a versatile space for creative pursuits, hobbies, or use as a pool cabana.

149 Litchfield Road, Edgartown

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..
$4,700,000
3 Beds ⋅ 4 Baths ⋅ 73536845 MLS
Sense of place is the initial impression one ascribes of 23 Ocean Street in Manchester-by-the-Sea. This spectacular Contemporary home could easily be sited on the rugged Northern California coast, yet here we are on the refined North Shore of Boston. The property overlooks White Beach, the coastal marshes spreading toward Black Beach and the open Atlantic Ocean. The elevated position above the shoreline ensures privacy and enhances the rhythm of the sea. The great room has cathedral ceilings, fireplace, bookcases and walls of glass that frame the ever-changing views. Sliders lead out to magnificent multi-level decks that provide sublime entertaining spaces. The kitchen features contemporary white cabinetry, high-end appliances (Thermador, SubZero, Meile). The primary suite has luxe bathroom, fireplace and a home office in the tower. How cool! An intimate library, two additional bedrooms, one en-suite rounds out this level. First level bonus room with bath, two car garage & gardens.

23 Ocean Street, Manchester

Listing courtesy of Listing Agent: Scott Smith from Listing Office: Coldwell Banker Realty - Manchester.
$4,695,000
6 Beds ⋅ 10 Baths ⋅ 73555839 MLS
Sophisticated elegance on approximately an acre of land in highly desirable neighborhood. A warmth upon entering through the grand foyer reveals an abundance of natural light and 76 impressive oversized windows. Beautiful architectural elements are revealed as the floor plan flows through an open concept chef's kitchen • butler's pantry • 5 entertaining rooms • 2 private home offices • media room • 6 en suite bedrooms • main level bedroom suite • fitness center • game room • sports bar with lounge • wine cellar and tasting room • 2 large stone patios • outdoor kitchen and fireplace • tranquil views of large flat private rear yard • 3 car heated garage. Nearby entrance to 150 acres of historic conservation land including trails, ponds, meadows, and antique stone walls. Just blocks to historic Lexington center and both elementary and middle schools. Easy commuter location to routes 3, 2 and I-95.

23 Burroughs Road, Lexington

Listing courtesy of Listing Agent: Andrea Jackson from Listing Office: Barrett Sotheby's International Realty.
$4,695,000
3 Beds ⋅ 2 Baths ⋅ 73478787 MLS
Downtown Vineyard Haven with Harbor Views. Positioned between the energy of Main Street and the quiet prestige of West Chop, this location delivers a rare balance of downtown access, privacy, and harbor frontage. Built in 2015, the three-bedroom, two-bath modern ranch is designed for easy first-floor living with expansive water views. Wide, harbor-facing windows showcase the meadow and water beyond. The interior feels open, calm, and intentional, with spaces that flow naturally toward the outdoors and keep the focus where it belongs. Outside, the landscape opens gently toward the water. A private beach path sits immediately adjacent to the Vineyard Haven Yacht Club, offering sailing, tennis, dock access, and a café just steps away, an uncommon amenity pairing in such a peaceful, natural setting. Whether enjoyed as a personal escape or leveraged as an income-producing property, the home’s strong rental history reflects its wide appeal.

16 Frog Hollow, Tisbury

Listing courtesy of Listing Agent: Rose Ryley from Listing Office: Wallace & Co. Sotheby's International Realty.
$4,650,000
5 Beds ⋅ 7 Baths ⋅ 73502884 MLS
Situated in the coveted gated neighborhood of Seaside between the Ocean and country club stands this stunning retreat. As you approach the home you will notice the classic charm is grand yet welcoming. The open concept living area has coffered ceilings a fireplace and plenty of space for guests to gather. The kitchen is truly a delight with a large center island and top of the line appliances. In the back yard you have both covered and open patio spaces surrounding a heated pool. The first floor Primary Suite has direct patio access, a large walk in closet and a private en-suite that is perfect after a long day. Upstairs has 2 bedrooms each with their own dedicated bath a sitting area and a rooftop deck overlooking the ocean! The lower level contains additional sleeping areas an office space as well as a family room. The 2 car garage features a guest suite above it perfect for longer term guests. Enjoy deeded access to the beach just steps away. Be the home where everyone gathers.

5 Coastline Drive, Mashpee

Listing courtesy of Listing Agent: Timothy Morgan from Listing Office: RE/MAX Innovative Properties.
$4,600,000
3 Beds ⋅ 5 Baths ⋅ 73563876 MLS
An exceptional home in a coveted area, 165 Wings Neck Road pairs remarkable craftsmanship with a spectacular coastal setting overlooking Pocasset Harbor and Bassett’s Island. Custom built by noted luxury home builder Peter B. Coffin, this approximately 5,000-square-foot residence was conceived with an uncompromising level of quality, scale and detail, surrounded by beautifully landscaped grounds with a heated gunite pool and extraordinary water views.Light-filled interiors unfold in an open, sophisticated plan designed equally for entertaining and everyday coastal living. Three south-facing decks embrace the scenery, while distinctive architectural details include hand-hewn hickory floors, extensive custom millwork and built-ins, and seven fireplaces throughout the home. The expansive kitchen serves as the heart of the residence with a large island, pantry and generous gathering space. Main and upper floor primary suites offer exceptional privacy, complemented by additional guest accommodations. A four-person elevator connects the living levels with the four-car garage, adding convenience rarely found in a Cape Cod residence of this character.Outside, the experience is equally compelling. The pool and landscaped grounds create a private resort-like retreat, while views stretch across Pocasset Harbor toward Bassett’s Island with the natural landscape of the neighboring Wings Neck Sanctuary completing the backdrop. Rare on its own and even more extraordinary as part of a larger opportunity, adjacent 155 Wings Neck Road is also offered for sale. Acquire 165 individually or consider both residences together to create a significant multi-home coastal compound on one of Pocasset’s most desirable stretches of shoreline.

165 Wings Neck Rd, Bourne

Listing courtesy of Listing Agent: Fisher and Marks from Listing Office: .
$4,600,000
6 Beds ⋅ 6 Baths ⋅ 73522816 MLS
Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic five-bedroom main residence, along with a separate one-bedroom carriage house, are rich in character and await a thoughtful renovation or reimagining. Ideally located near the clubhouse, restaurant, tennis courts, and pro shop, the property offers easy access to the Farm Neck lifestyle while remaining just minutes from town, the harbor, and ferry terminal. This is an extraordinary chance to secure a property within the esteemed Farm Neck Golf Club community. Included is a highly sought-after Farm Neck Club Stockholder Membership, enhancing both its prestige and value.

15 Tamarack Lane, Oak Bluffs

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..
$4,600,000
4 Beds ⋅ 4 Baths ⋅ 73514104 MLS
ONE MILE FROM HISTORIC EDGARTOWN VILLAGE. NEW home with a POOL, and close to SOUTH BEACH. The facade offers a covered porch. The entry foyer presents with an oversized lounge area to the right and a spectacular great room ahead. The great room has a soaring cathedral ceiling and a rear wall of two story windows with a gas fireplace. The great room opens to the dining room with a wall of glass doors overlooking the pool area. The dining room flows into the gourmet kitchen with a seating island. Off the dining and kitchen area is access to the mudroom which has a half bath, pantry, and laundry area. Off the mudroom area is an outdoor shower. The first floor hosts the primary bedroom with a luxurious bathroom. The second floor has three guest rooms and two full bathrooms. The rear yard offers privacy in the 14 x 30 ft. salt water heated pool that is surrounded by bluestone and professional landscape.

9 Marthas Way, Edgartown

Listing courtesy of Listing Agent: Michele Casavant from Listing Office: Vineyard Village Realty.
$4,600,000
7 Beds ⋅ 5 Baths ⋅ 73496611 MLS
In the intellectual heart of Cambridge, a residence of architectural grandeur offers a rare convergence of substance and tranquility, just steps from Harvard Sq & Charles River. This Victorian lives like a grand single-family home while possessing the versatility of a 2-family. Spanning 3824sqft, its 15 rooms are defined by generous proportions, natural light, timelessness of five fireplaces. The layout features 5 beds, 3F/2H baths, sunroom. At its heart is a chef’s kitchen, a welcoming space with a large island, high-end appliances, intimate seating. Discover a private urban sanctuary on the sprawling 6563sqft lot, where a perfected Zen-like garden creates an idyllic retreat for serene lounging. A coveted side-by-side 2-car driveway, Central AC, private-entrance au-pair/guest suite provide ultimate flexibility. Expansive 1174sqft high-ceilinged unfinished basement awaits your vision. Unique opportunity to live moments from iconic museums, acclaimed dining. Currently rented through Dec 31, 2026. Showings by Appointment Only

32 Hawthorn St, Cambridge

Listing courtesy of Listing Agent: Mac Chinsomboon from Listing Office: Coldwell Banker Realty - Boston.
$4,599,000
6 Beds ⋅ 7 Baths ⋅ 73562908 MLS
Welcome to 35 Willard Street, a rare and pristine six-bedroom, six-and-a-half-bath single-family residence built in 2017, offering 4,800SF of beautifully designed living space across four levels. Ideally situated in Cambridge’s coveted Half Crown–Marsh neighborhood, the home is just moments from the Charles River and Harvard Square and features an attached two-car garage and a fully equipped au pair/in-law suite. A grand foyer introduces the main living level, with a gracious corner dining room framed by bay windows on one side and an inviting living room with a bay window and fireplace on the other. At the heart of the home is a chef’s kitchen appointed with Sub-Zero and Wolf appliances, a pantry, and breakfast bar. A powder room completes the level, while an elegant staircase accented with custom wainscoting connects the upper floors and garden level. The second floor features three bedrooms, each with an en suite bath. The spacious primary suite includes a custom-built walk-in closet and a luxurious bath with a dedicated soaking tub and oversized shower. The third floor offers two additional bedrooms, one of which offers an en suite bath and another full bath, a custom-built laundry room, and access to a private roof deck. The garden-level au pair/in-law suite provides exceptional flexibility with its own chef’s kitchen, full bath, additional laundry, and private entrance. An attached, EV-ready two-car garage and a private side patio ideal for al fresco dining and entertaining complete the home. 35 Willard Street offers an exceptional combination of scale, thoughtful functionality, outdoor space, and location in one of Cambridge’s most coveted residential neighborhoods, with convenient access to Harvard Square, BB&N, Charles River, and Downtown Boston.

35 Willard St, Cambridge

Listing courtesy of Listing Agent: Jennie & Eddie Luxury Living Boston Team from Listing Office: Regatta Realty.
$4,599,000
6 Beds ⋅ 7 Baths ⋅ 73542515 MLS
Set in one of Andover's most exclusive neighborhoods, this newly constructed estate enjoys a premier location beside The Pike School and within the prestigious Phillips Academy area—an address synonymous with distinction, academic excellence, and enduring value. Opportunities to own new construction of this caliber in such a highly regarded setting are exceedingly rare. Designed for modern living and entertaining, the home features six bedrooms, six full baths, and one half bath, offering a blend of comfort, elegance, and functionality. Expansive living spaces, architectural details, and premium finishes create an atmosphere of timeless luxury. A private first-floor guest suite with direct patio access and a mudroom with a dedicated dog wash station add convenience and flexibility. The sought-after location places residents moments from downtown Andover's dining, shopping, and commuter routes while enjoying the character of one of the town's distinguished neighborhoods.

7 Cider Hill Way, Andover

Listing courtesy of Listing Agent: Team Lillian Montalto from Listing Office: Lillian Montalto Signature Properties.
$4,595,000
5 Beds ⋅ 3 Baths ⋅ 73503067 MLS
Presenting a rare waterfront Eastern Pt compound spanning 3 contiguous parcels, ideally located between the yacht club and iconic lighthouse. This unique offering includes two single-family homes and a charming bunkhouse. 127 features a two-story, 2-BR home with a flexible first floor: 2 BRs, den, and screened porch which can comfortably host additional sleeping, and the stunning second-floor features an open-concept kitchen, dining, and living area with cathedral ceiling and a 30-foot wraparound deck. 129 is a single level, 3-BR bungalow with an updated kitchen, open living/dining, sunroom, and spacious wraparound deck. Completing the property, 131 has the delightful 11' x 15“ bunkhouse (has electricity, no plumbing), and is outfitted with 4 beds and a waterfront window that opens to an outdoor bar. A one-of-a-kind coastal retreat, with character and versatility - perfect for hosting family and guests. Attached is a feature sheet that provides detailed information about each parcel.

127-131 Eastern Point Blvd, Gloucester

Listing courtesy of Listing Agent: Barbara Dugan from Listing Office: Engel & Volkers By the Sea.
$4,585,000
6 Beds ⋅ 7 Baths ⋅ 73575514 MLS
Introducing an elegant shingle and stone residence prominently situated in the prestigious Weston Estates neighborhood. This custom home is masterfully constructed with fine attention to detail by an acclaimed builder. A striking stone fireplace graces the family room and complements the open concept design. The classic floor plan features a grand two story foyer, charming sun room and fabulous finished lower level. The 6th bedroom suite located on the 3rd floor can be used as an in-home office or as a special getaway for guests. The exceptional grounds are architecturally enhanced with a decorative gazebo with a built-in kitchen. The exquisite backyard has a sprawling stone patio adorned with beautiful perennial gardens and manicured grounds. This unique home has all the desired amenities and gravitas for the most discerning buyer.

21 Westerly, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.
$4,550,000
6 Beds ⋅ 7 Baths ⋅ 73521390 MLS
Beautifully built custom home in the coveted Sesuit Neck area of East Dennis, crafted for those who expect the exceptional. Every inch reflects uncompromising quality - from the elevated design to the premium materials - creating a residence that stands out as one of the area's finest. The sun filled open floor plan showcases an expansive living room with custom built-ins, elegant coffered ceilings, and a striking wood burning fireplace - an inviting centerpiece for gatherings. Throughout the home, rich wood floors set a warm, refined tone. A substantial first floor primary bedroom is enhanced by a private bath and walk in closet. The chef's kitchen is a true showpiece, featuring custom cabinetry, top tier Wolf appliances, and a generous center island designed for effortless cooking and entertaining. The second-floor features five well-appointed bedrooms, three full baths, and a versatile area currently used as a den. The finished lower level expands the home's living potential with an additional 1,842 sq. ft., offering a spacious family room and a full bath - perfect for guests, recreation, or a private retreat. The resort style backyard is a true private oasis, offering an expansive setting designed for unforgettable outdoor living. A sparkling inground pool anchors the space, complemented by a 384 sq. ft. cabana complete with a kitchenette and half bath - perfect for effortless poolside entertaining. The fire pit lounge, enclosed porch, and sweeping yard provide endless room for relaxation, recreation, and gatherings of any size. Just a short distance to Harborview Beach, Sesuit Harbor Marina, Dennis Yacht Club and of course the very popular Sesuit Harbor Café. This is truly an outstanding offering. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

10 Shiverick, Dennis

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .
$4,500,000
7 Beds ⋅ 6 Baths ⋅ 73575037 MLS
A landmark of Magnolia's storied coastline, this extraordinary oceanfront estate has graced Shore Road since 1889. Set above the Atlantic on one of Cape Ann's most coveted seaside addresses, the residence masterfully blends timeless architecture with thoughtfully curated updates, creating a home that feels both historically significant and effortlessly livable. Sunlight pours through expansive windows, illuminating gracious rooms designed for intimate gatherings and grand entertaining alike, while six fireplaces add warmth and character throughout. Outside, terraces and gardens frame panoramic ocean vistas where the rhythm of the tides, passing sailboats, and spectacular coastal sunsets become part of everyday life. Just moments from Magnolia Village, beaches and miles of scenic conservation trails, this is a rare opportunity to become the next steward of one of the North Shore's most distinguished waterfront homes.

31 Shore Rd., Gloucester

Listing courtesy of Listing Agent: McDermott Group from Listing Office: Gibson Sotheby's International Realty.
$4,500,000
7 Beds ⋅ 9 Baths ⋅ 73574231 MLS
A remarkable Mid-Cambridge Colonial Revival stands prominently on a gorgeous tree-lined street. Offering an exceptional blend of period craftsmanship and thoughtful updates. The grand foyer showcases parquet inlaid floors, while soaring ceilings, oversized bay and box windows, time period accent stained glass windows, and two fireplaces highlight the home's historic character. Abundant natural light, hardwood floors, and recessed lighting create a warm and inviting atmosphere throughout. The updated kitchen is thoughtfully appointed with custom cabinetry, upper and under-cabinet lighting, granite counters, stainless steel Thermador double ovens, gas cooktop, paneled refrigerator and dishwasher as well as a half bathroom. Second floor offers a spacious primary suite with walk-in closets, private balcony, and grand primary bathroom with Jacuzzi soaking tub, custom-tiled shower, and double vanity. Continuing on the second floor there are two additioinal bedrooms, a full bathroom, and laundry room with sink and folding station. The third floor provides three spacious bedrooms with skylights, ample closets, and another full bathroom. This unique home includes an additional one bedroom one bathroom unit in the lower level with private entrance. This space can be utilized as an au pair, guest suite or rental unit. A private backyard oasis is accentuated by the manicured garden, patio, and green space offering room to relax and entertain. An oversized detached heated two car garage with additional storage and workshop complete this unique home. Just moments from the amenities of Harvard and Inman Squares. There is so much to love about this home.

32 Fayette Street, Cambridge

Listing courtesy of Listing Agent: The Team - Real Estate Advisors from Listing Office: Coldwell Banker Realty - Cambridge.
$4,500,000
5 Beds ⋅ 6 Baths ⋅ 73572602 MLS
An artful balance of historic character & modern design, this 5,423SF 5BD, 5.5BA 1891 Colonial Revival was meticulously renovated in 2017 and is set on .41AC of landscaped grounds. Oversized windows, tall ceilings, bespoke millwork, detailed crown moldings, & 4 fireplaces highlight the home’s craftsmanship. Welcoming entry w/ FP connects main floor. Bright living room w/ FP and dining room w/ French doors that lead to wraparound deck. Renovated open kitchen w/ island, pantry, and eat-in. Adjoining family room w/ gas FP & built-ins. 1/2BA & mudroom complete level. Upstairs is the primary suite w/ FP, spa-like bath, & walk-in closet, en-suite bedroom, add’l bedroom, full bath, & laundry. Flexible 3rd floor flex w/ 3 add’l rooms & bathroom - ideal as bedrooms, offices, or play space. Walkout lower level w/ private entrance, en-suite bedroom, 2nd kitchen, family room, & storage. Private setting w/ tiered grounds, bluestone patio, & extensive lawn framed by mature trees & seasonal plantings

50 Sumner Road, Brookline

Listing courtesy of Listing Agent: Hilary Maddox Team from Listing Office: Compass.
$4,500,000
4 Beds ⋅ 5 Baths ⋅ 73556459 MLS
Waterfront new construction in one of Chatham's most preeminent locations, minutes from town. This rare half-acre offering on Emery Pond is to be built by R.A. Martin, one of the Cape's premier builders, with select interior finishes and customizations still available to the right buyer. New construction of this scale is exceptionally rare on Cape Cod, offering the perfect mix of estate-level living and an in-town lifestyle, all with stunning water views. The finished residence offers approximately 4,689 square feet of considered living space across three thoughtfully composed levels, with 4 bedrooms and 4 full baths. Sunlit interiors flow effortlessly from kitchen to dining to generous entertaining spaces, opening to a screened porch and deck framing sweeping views of the pond. Outside, a waterfront pool anchors a true outdoor retreat -- a private, resort-style setting for gathering, moments from town. A primary suite anchors the upper level alongside an office and two additional bedrooms, while the lower level offers a fourth bedroom suite and a generous recreation room. A rare opportunity to build new construction with a coveted mix of setting, space, and location on Emery Pond.

66 Ethelma Dr, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$4,500,000
4 Beds ⋅ 5 Baths ⋅ 73497147 MLS
Exceptional East End offering spanning from Commercial Street to Bradford Street! This rare two-parcel opportunity consisting of 624 Commercial Street and 309 Bradford Street is awaiting your vision! Ideally situated near public access to a pristine bay beach, this assemblage combines location, versatility, and potential. 624 Commercial Street offers a 5,002 sq ft lot with a newly constructed three-bedroom residence, with the possibility to accommodate a fourth bedroom or ADU. 309 Bradford Street features an 8,175 sq ft lot with a charming one-bedroom cottage, well-suited for guest accommodations or rental use. Both properties include generous outdoor space and off-street parking, presenting a unique opportunity for expansion, investment, or the creation of a private compound in Provincetown's desirable, and historic East End.

309 Bradford Street, Provincetown

Listing courtesy of Listing Agent: The Rose Kennedy Team from Listing Office: Gibson Sotheby's International Realty.
$4,500,000
4 Beds ⋅ 4 Baths ⋅ 73492591 MLS
Panoramic Stage Harbor views are the centerpiece of this exceptional Morris Island waterfront setting. The property offers four bedrooms and 3.5 baths, each room oriented to the scenery beyond. The residence pairs a classic seaside character with an elevated aesthetic. The main living level is bright and welcoming with a high-end kitchen, generous living room and dining area overlooking the water and doors to an expansive waterside deck. A versatile layout supports single-level living, featuring a first-floor suite currently enjoyed as a family room with a fireplace, soaring ceilings, full bath, and access to the deck. The upper level includes three bedrooms and a den, all benefiting from stunning outlooks. Professionally designed grounds provide a sense of seclusion, complemented by a private footpath to the shoreline. An exceptional offering in one of Chatham's most coveted waterfront locations.

346 Morris Island Road, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.
$4,500,000
6 Beds ⋅ 8 Baths ⋅ 73481194 MLS
Newly refreshed English Country Estate ready to be discovered! Recently enhanced with a sophisticated neutral palette, this extraordinary 9,300+ sq ft residence is privately sited on 4.5 magnificent acres at the crown of one of Southborough’s most distinguished estate neighborhoods. Surrounded by 180 acres of conservation land, the home offers exceptional privacy, architectural distinction and timeless craftsmanship. Grand formal rooms with exquisite millwork flow to inviting everyday living spaces, while seven gas fireplaces create unexpected warmth throughout. Six bedrooms include a luxurious primary suite with dual spa baths and magnificent sunset views. Resort-style grounds feature multiple terraces, a heated freeform pool, formal English gardens, sculpted hedges, perennial blooms and a flourishing apple orchard with working cider press. An irreplaceable private estate setting just one mile from Fay and St. Mark’s Schools and 25 miles from downtown Boston.

12 Wyndemere Drive, Southborough

Listing courtesy of Listing Agent: Ginny Martins from Listing Office: Ginny Martins & Associates.
$4,500,000
6 Beds ⋅ 7 Baths ⋅ 73479712 MLS
Set within a private gated enclave in South Chatham’s emerging luxury corridor, 48 Sylvan Way is a singular estate moments from the Cape’s most iconic downtowns, beaches, and dining. Encompassing 1.63 acres with exceptional usability and recreational, the property offers rare privacy and scale in one of Chatham’s most compelling settings. Spanning 5,700 square feet across twelve rooms, this bespoke new construction residence showcases custom craftsmanship and intentional design, conceived for refined, generational living. Three distinct bedroom wings provide comfort and separation, with each bedroom generously sized and ensuite. At its heart, a breathtaking great room anchored by a custom-designed kitchen rises to 23-foot shiplap ceilings with reclaimed beams and a fireplace, while an 18-foot wall of glass opens to the heated saltwater pool and patio for seamless indoor-outdoor living. A rare offering defined by craftsmanship and presence —modern Cape Cod estate living elevated.

48 Sylvan Way, Chatham

Listing courtesy of Listing Agent: Guthrie Schofield Group from Listing Office: .
$4,499,900
5 Beds ⋅ 7 Baths ⋅ 73555706 MLS
An extraordinary new luxury residence to be constructed in Dedham’s coveted Precinct One. Thoughtfully designed to blend timeless architecture with modern living, this exceptional home will offer approximately 4,000–6,000 square feet of refined living space, premium finishes, and outstanding craftsmanship throughout. Depending upon the stage of construction, purchasers may have the opportunity to personalize select finishes and design elements. Ideally situated on one of Precinct One’s most desirable streets, the property offers convenient access to Legacy Place, private schools, commuter routes, and downtown Boston. Renderings are for illustrative purposes only. Specifications, dimensions, features, and finishes are subject to change.

262 Meadowbrook Road, Dedham

Listing courtesy of Listing Agent: Michael Musto from Listing Office: RE/MAX Distinct Advantage.
$4,499,000
6 Beds ⋅ 5 Baths ⋅ 73574595 MLS
A landmark South End residence, The William Bartlet House is an exceptional Federal estate where timeless architecture & refined luxury exist in perfect harmony. Meticulously restored & impeccably maintained, the home showcases a rare double-hanging staircase, soaring ceilings, original wide pine floors, exquisite millwork, seven elegant fireplaces & richly detailed period craftsmanship. Grand formal rooms, a distinguished game room, sophisticated wet bar, chef's kitchen with Viking appliances & butler's pantry & a sun-filled conservatory create an extraordinary setting for both intimate living & grand-scale entertaining. The luxurious primary suite is a private sanctuary featuring an expansive sitting room, dual custom walk-in closets & spa-inspired marble bath. Outdoors, a heated, gunite saltwater pool & spa, bluestone terraces, manicured English garden with fountain & manicured landscape. A rare opportunity to own one of Newburyport's most distinguished historic homes in the most coveted neighborhood.

19 Federal St, Newburyport

Listing courtesy of Listing Agent: Kevin Fruh from Listing Office: Gibson Sotheby's International Realty.
$4,499,000
4 Beds ⋅ 4 Baths ⋅ 73571534 MLS
Welcome to The Cliffs, one of West Falmouth's premier coastal neighborhoods, offering a private sandy association beach on Buzzards Bay. This stunning new construction combines contemporary shingle-style architecture with a fresh, refined coastal design. Offering approximately 3,700 sq. ft., the home features 4 bedrooms, 3.5 baths, hardwood floors, high ceilings, custom built-ins and two gas fireplaces. The main level offers a spacious primary suite with two walk-in closets and private bath, an open kitchen with quartz countertops and center island, dining area, sunroom and light-filled living room. Upstairs, a second en-suite bedroom is joined by two additional bedrooms with a shared bath, a den and unfinished bonus space over the two-car garage. Outside is a true summer retreat with a heated pool and spa, expansive patio, outdoor kitchen, outdoor shower and fenced yard. Exceptional craftsmanship and coastal style come together in an extraordinary West Falmouth setting.

51 Cliff Road, Falmouth

Listing courtesy of Listing Agent: Christine O' Leary from Listing Office: Salt Pond Realty, LLP.
$4,499,000
4 Beds ⋅ 3 Baths ⋅ 73434698 MLS
Own a coveted East Orleans property with a private deep-water dock on a sprawling 2.62 acres, just 2.6 miles from Nauset Beach. This estate, surrounded by water, features rolling meadows and mature trees. The 3,867 sq ft residence blends timeless charm with modern comforts. Located on Lucy's Point Peninsula, it's perfect for a family compound or riverfront retreat. Inside, enjoy wide plank pine floors, decorative fireplaces, and historic moldings. The layout offers open spaces and privacy, with four bedrooms, three bathrooms, and diverse living areas. The primary ensuite is a private wing with a sitting area and walk-in closet. The kitchen setup is ideal for culinary creativity. Entertain or relax in the nostalgic ambiance. A newer roof, heating, and AC ensure comfort. Outdoors, a versatile barn/boathouse offers recreational possibilities. Whether seeking tranquility or lively gatherings, 66 Tides End Lane welcomes you with grace and beauty.

66 Tides End Ln, Orleans

Listing courtesy of Listing Agent: Cape Cod Power of Two from Listing Office: Compass.
$4,499,000
8 Beds ⋅ 9 Baths ⋅ 73377530 MLS
Nestled in the heart of the West End, this historic 1847 Greek Revival Captain's Home is now available for purchase after 29 years under the same ownership. As one of the largest buildings in the neighborhood, the West End Inn serves primarily as a private residence but is also licensed as a B&B. The first floor was completely renovated in 2019. The property features three kitchens, a kitchenette, and four separate living quarters, each with private entrances. The light-filled, three-family layout offers potential to be converted into a substantial single-family home. There are nine bathrooms, eight bedrooms, two dens, two decks, two private garden spaces, and a beautifully appointed front yard. The top floor, with its large deck, provides water views and unobstructed vistas of Telegraph Hill and stunning sunsets. Parking is available for five or more cars, and beach access is directly across the street. Betterment paid in full.

44 Commercial Street, Provincetown

Listing courtesy of Listing Agent: Iskren Georgiev from Listing Office: Gibson Sotheby's International Realty.
$4,495,000
5 Beds ⋅ 8 Baths ⋅ 73573141 MLS
A striking new construction residence at Brush Hill, thoughtfully designed with timeless architecture, elevated finishes, and today’s most sought-after amenities. The exterior makes an immediate impression with custom-colored LP Smart Siding, CertainTeed architectural shingles, partial brick façades, and elegant brick and bluestone entryways. Marvin windows and doors enhance both aesthetics and energy efficiency while filling the home with natural light. Outdoor living is seamlessly integrated with a built-in grill and outdoor Sonos speakers, ideal for entertaining.Inside, the home blends sophistication and comfort across every level. Six-inch engineered hardwood floors flow throughout, complemented by custom moldings, built-ins, and both gas and wood-burning fireplaces. The chef’s kitchen serves as the heart of the home, featuring a custom-designed kitchen and hood, Sub-Zero and Wolf appliance package, a 48” column refrigerator/freezer combination, 48” Wolf induction range, Cove dishwasher, and quartz countertops.A fully appointed butler’s pantry adds exceptional functionality with an additional oven, microwave, water bottle dispenser, Miele coffee system, and Thermador wine refrigerator—perfect for entertaining and everyday convenience.Designed with wellness and recreation in mind, the home includes three bathrooms with heated floors, a private sauna with red light therapy, a dedicated gym, and a finished basement bar. An optional TrackMan golf simulator offers a unique and elevated recreational experience.Additional features include a whole-house Sonos sound system, prewired alarm and camera system, and full-house water filtration—delivering comfort, security, and peace of mind. This exceptional new construction at Brush Hill offers a rare combination of luxury, lifestyle, and thoughtful design.

688 Brush Hill Road, Milton

Listing courtesy of Listing Agent: Scott Farrell & Partners from Listing Office: Compass.
$4,495,000
5 Beds ⋅ 5 Baths ⋅ 73550033 MLS
SARGENT ESTATES! Privately set on approximately 1 acre in Brookline's coveted neighborhood, this exceptional contemporary residence offers over 6,800 square feet of light-filled living space surrounded by mature trees & natural beauty. A winding drive leads to this 5+ bedroom, 4.5-bath home featuring soaring ceilings, expansive walls of glass & seamless indoor-outdoor living. The custom kitchen opens to an impressive 720-square-foot living and dining room with fireplace & dramatic ceilings, flowing to an expansive deck overlooking the tranquil grounds & swimming pool. The first floor also includes 2 bedrooms, 2 full baths & a half bath. Upstairs, the private primary suite offers an updated bath, walk-in closet, office, sitting room & oversized deck. The walk-out lower level features a large recreation room, playroom, exercise room, 2 bedrooms and a full bath. A two-car garage completes this remarkable property just minutes from schools, shops, hospitals & downtown Boston.

108 Codman Rd, Brookline

Listing courtesy of Listing Agent: Jamie Genser from Listing Office: Coldwell Banker Realty - Brookline.
$4,495,000
6 Beds ⋅ 7 Baths ⋅ 73535655 MLS
Your family's everything dream home is already built for you with both elegance and warmth as soon as you step in. Light-filled rooms throughout, featuring window seating both in the kitchen's separate eating area and in the hexagonal library. Floor to vaulted ceiling windows that flank the grand stone and brick fireplace in the Great Room and carry you to the gourmet kitchen with quartz countertop island for fabulous entertaining. This leads through a fully equipped butler's pantry to an unmatched dining room with built-in cabinetry, fireplace, and arched windows. Flooring of marble, tile and oak are found throughout, with views front to back. Or choose the magnificent sunroom, which steps out to stone patios for gatherings all across the yard with a level grassy area for endless possibilities. Walk the sidewalks with stately Boston street lamps. Fall asleep at night in luxury with a fireplace, spa bath ensuite, and choose your outfits in the morning from your two walk-in closets.

20 Longmeadow Drive, Westwood

Listing courtesy of Listing Agent: Peter Cwieka from Listing Office: Media Realty Group Inc..

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