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10 Somerset Road, Provincetown
$2,625,000
3 Beds ⋅ 4 Baths ⋅ 22602033 MLS
I am pleased to present 'Sweet Home,' a custom-built residence located in the Somerset Heights East End neighborhood. This property features three private bedroom suites, each equipped with an en suite bathroom and an independent entrance. The primary suite is located on the top floor and includes a rooftop deck offering panoramic views and privacy. Notable amenities include radiant heating, a/c and heating split systems, hardwood flooring,custom sinks and a central vacuum system, two fireplaces (including one double-sided unit), owned Tesla solar panels, electric charging station and Powerwall system, professional landscaping with irrigation, screened porches, a patio, and a hot tub. The interior and exterior have been recently painted, and the home offers significant rental income potential. The property is situated near conservation land, providing a quiet setting within walking distance of the Bay Beach and a short distance from town.

10 Somerset Road, Provincetown

55 Winterset Drive, Chatham
$2,245,000
4 Beds ⋅ 4 Baths ⋅ 22603375 MLS
Exceptional Great Hill Estates retreat being offered fully furnished, set on 1.8 private acres with deeded rights to Lover's Lake for kayaking, swimming, and canoeing just a short foot path away. Located on a scenic corner lot, this 4-bedroom, 3.5-bath home offers peaceful natural surroundings and room to relax both inside and out. A first-floor primary suite features ensuite bath and laundry for convenient single-level living. The heart of the home is a spacious kitchen with a large island, dining area, and adjacent great rooms with vaulted beamed ceilings and fireplaces. A wraparound deck, perfect for outdoor dining, entertaining, or simply enjoying the views. Upstairs are two bedrooms and a full bath, including one bedroom with a fireplace and sitting area that offers a private retreat-like feel. The walk-out lower level features a fourth bedroom, full bath, another laundry area, and direct access to a stone patio with custom seating and gas fire pit. Additional highlights include central ac, hardwood floors, two-car attached garage and new Bosch heating system. Close to Chatham Village, Lighthouse and Hardings beaches, bike path and tennis courts.

55 Winterset Drive, Chatham

8 Snail Road, Chilmark
$15,400,000
6 Beds ⋅ 9 Baths ⋅ 22602961 MLS
Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects and artisans. Grounded in its natural setting, the architecture features dramatic design elements and walls of glass to connect seamlessly with the idyllic landscape. An infinity-edge pool overlooks the pastoral ocean horizon that defines Chilmark, while a screened porch and large outdoor living areas extend the home into its surroundings. A separate 2-bedroom guest house and additional 5.6 acre lot provide flexibility for expansion and subdivision, while a private path to Chilmark Pond allows for deeded access to South Beach. Horizon House is a pleasure to show, by appointment only.

8 Snail Road, Chilmark

23 Crestview Circle, Truro
$2,899,000
4 Beds ⋅ 2 Baths ⋅ 22503440 MLS
MAJOR PRICE IMPROVEMENT! NOW OFFERED AT $2,899,000. Perched high above Cape Cod Bay with sweeping views to Provincetown, 23 Crestview Circle is a rare bluff-top offering defined by privacy, elevation, and an ever-changing coastal landscape. Set along one of Truro's more private stretches of shoreline, the property enjoys approximately 250 feet of sandy beach below, accessed via a secluded stairway, along with unobstructed sunsets across the bay. The home reflects a classic mid-century coastal sensibility, with vaulted ceilings, warm wood tones, and a layout oriented toward the water. The main living area, anchored by a fireplace and expansive glass, opens to a covered deck, creating a seamless connection between indoor and outdoor living. With four bedrooms and two full baths, the home is comfortably scaled for family and guests. The kitchen flows naturally into the living and dining areas, all positioned to take full advantage of the views. Just minutes from Provincetown, yet set in a world apart, this is a rare opportunity to experience the Outer Cape at its most compelling.

23 Crestview Circle, Truro

336 Stage Island Road, Chatham
$2,699,000
3 Beds ⋅ 3 Baths ⋅ 22601983 MLS
Stage Island is among the most exclusive addresses on Cape Cod -- a private, tight-knit enclave of fewer than 40 homes where properties rarely change hands and waterfront offerings are nearly nonexistent. When one does surface, it commands attention. This is that moment. Set on 1.07 waterfront acres, this property delivers a generational setting defined by sweeping marsh and water views, breathtaking sunsets, and a bucolic lot surrounded by abundant conservation land. The 3-bedroom, 2,200+ SF contemporary residence is thoughtfully sited and bathed in natural light. A wall of windows and doors anchors the main living area with 270-degree views. The private primary suite features its own deck and a soaking tub with waterfront views -- an orientation that simply cannot be improved upon. Outside, gardens, patios, and decks unfold into multiple entertainment zones designed for alfresco dining, yard games, and summers well spent. Move-in ready and meticulously maintained, the expansive footprint also offers meaningful runway for further development. A setting this rare, in a community this sought-after, does not come twice.

336 Stage Island Road, Chatham

256 Browns Neck Road, Wellfleet
$1,545,000
4 Beds ⋅ 4 Baths ⋅ 22601119 MLS
A beautiful home for all seasons! This stunning architect-designed, custom-built contemporary home, being sold with its adjoining separate lot of .73 of an acre, is a unique offering located in a private, quiet marshside location on the outskirts of Wellfleet Village. Being offered turn-key, this tasteful, stylish and well-maintained home features an open floor plan with an abundance of glass that brings the outside in. It has an open living room, kitchen, and dining room, further opening to an expansive deck located across the back of the home. The basis of the overall design is about creating privacy within the home as the bedrooms are spaced throughout the house, with a spacious second-floor en-suite primary bedroom accessed by a private staircase, and a separate ensuite guest bedroom with its own staircase. and two first-floor bedrooms with a shared bath. There is also a garden-level room that is perfect for any use where a private, quiet space is needed. Other notable features are an oversized two-car garage, a fireplace, an outdoor shower, air conditioning, and a beautiful, natural, serene setting. Back road access and proximity to all the in-town attractions, marina, beaches, and ponds add to the appeal. Shown by private appointment.

256 Browns Neck Road, Wellfleet

25 Noons Drive, Truro
$1,395,000
3 Beds ⋅ 2 Baths ⋅ 22602566 MLS
Postcard-worthy views of Cape Cod Bay are showcased from each room on the main level of this beautifully maintained ranch-style/contemporary influenced home. Relax and enjoy spectacular sunsets over the Bay from your year-round residence or seasonal retreat. Tucked away on a private road, this three-bedroom, two-bath home has been thoughtfully updated in recent years, featuring a new kitchen, updated bathrooms, replacement windows, a new furnace, and numerous additional improvements. Sited to maximize its exceptional water views, the home offers direct access to its gardens and spacious deck from nearly every main-level room. The deck features a relaxing whirlpool spa, creating the perfect setting for outdoor enjoyment. The main living area is ideal for entertainment, with a spacious living room featuring cathedral ceilings, a wood-burning fireplace, and expansive glass sliders that open to the deck and views beyond. The adjoining kitchen is equipped with stainless steel appliances, granite countertops, and flows seamlessly into a separate dining room.Also located on the main level are two bedrooms, including a generous primary suite with abundant closet space, a sitting area and home office nook, en-suite bath, and direct deck access. The guest bedroom is also generously sized and features sliders opening to the deck. The third bedroom is located on the lower level and offers its own private walkout entrance, making it ideal for guests or extended family. This level also includes a spacious laundry room and ample storage space. Whether you're seeking a full-time residence or a Cape Cod getaway, 25 Noon Drive offers a rare opportunity to enjoy stunning bay views, privacy, and comfortable coastal living.

25 Noons Drive, Truro

135 Newcomb Hollow Road, Wellfleet
$2,950,000
5 Beds ⋅ 3 Baths ⋅ 22601246 MLS
Nestled within the National Seashore, this 4-bedroom home, with 1-bedroom studio, sits on 2 acres, offering unmatched privacy and stunning ocean views. Located a stone's throw from Newcomb Hollow beach, freshwater ponds, and a short ride to town. The mid-century main house features a spacious living area and a solarium, maintaining many original design elements. Enjoy breathtaking Atlantic vistas through custom windows and sliding doors, which open to a generous deck, seamlessly blending indoor and outdoor living. Additionally, a renovated, detached 820 SF free-standing studio offers a space rich in architectural details, perfect for creativity or relaxation. This exceptional property presents an opportunity to restore the existing home or design your own vision on a large parcel. Just a short distance from Newcomb Hollow Beach, it's an ideal retreat for inspiration and solitude. Make 135 Newcomb Hollow Road your own and join the lineage of creatives who have called this place home.

135 Newcomb Hollow Road, Wellfleet

40 Triton Way, Mashpee
$6,850,000
5 Beds ⋅ 6 Baths ⋅ 22600786 MLS
Set high on a scenic bluff in New Seabury, this contemporary oceanfront estate pairs dramatic Nantucket Sound views with resort-style living. Expansive walls of glass frame the water from vaulted great rooms and intimate sitting areas alike. A sunlit gourmet kitchen opens to multiple dining spaces, while the ocean-view primary suite offers a private balcony. Highlights include a home theater, fitness room, and lower-level entertaining space with direct patio access. Outside, tiered ocean view decks, manicured lawns, and a private path with steps to the water create a seamless connection to the coast. Crafted with exceptional quality, this rare property is designed for both grand gatherings and casual living. Located minutes from New Seabury's five-star amenities, Mashpee Commons, and everything else the area has to offer!

40 Triton Way, Mashpee

17,17A,17B Cranberry Lane, Falmouth
$1,995,000
7 Beds ⋅ 4 Baths ⋅ 22601428 MLS
Exceptional opportunity to own three updated, year-round homes on nearly 3 acres! Abutting the Coonamessett River, the property offers a tranquil, private setting, while still providing access to all Falmouth has to offer. The properties (main house and 2 cottages) are perfect as a family compound for multi-generational living or for income potential. Enjoy peaceful river views, your own working cranberry bog, visiting wildlife, and grounds ideal for relaxation and recreation. The light-filled main residence offers 3 bedrooms and 2 full baths plus a bonus room. The main level features updated kitchen and baths, cathedral ceilings, skylights, and a sunroom. French doors lead to a deck overlooking the river. Additional space is found in the finished, walk-out lower level. Two wood stoves - one on each level - provide efficient supplemental heating, complemented by gas heat. Two fully independent, updated cottages, each with 2 bedrooms, are ideal for extended family, guests, or year-round or seasonal rental income. Additional highlights include a septic system updated in 2021, town water for domestic use, and 2 private irrigation wells. Truly a special opportunity!

17,17A,17B Cranberry Lane, Falmouth

44 Carey Lane, Falmouth
$4,625,000
4 Beds ⋅ 4 Baths ⋅ 22603120 MLS
Waterfront contemporary luxury on a private lane in the coveted enclave of Quissett Harbor. Blending architectural distinction with coastal serenity, this exceptional 4BD/3.5BA residence offers light-filled living spaces designed for both everyday comfort and elegant entertaining. Soaring walls of glass and sun-filled interiors create a seamless connection to the surrounding landscape. The private primary suite wing features a study, walk-in closet, and expansive floor-to-ceiling windows. A separate bedroom wing offers two spacious guest rooms, while the second-floor guest suite provides flexible space for visitors, a home office, or artist's studio. Upgrades include native plant landscaping with new irrigation, new furnaces, and new roof. Two minute walk from scenic harbor offering a full service marina and yacht club. Adjacent is a nature preserve with hiking trails and secluded sandy beach. Unlimited recreation of sailing, kayaking, swimming at a private beach club, and nearby golf.

44 Carey Lane, Falmouth

20 Bayberry Avenue, Provincetown
$2,899,000
3 Beds ⋅ 5 Baths ⋅ 22603517 MLS
Located in Provincetown's sought-after West End, this beautifully designed contemporary home offers nearly 3,000 square feet of bright, thoughtfully planned living space. The dramatic second level features a cathedral-ceiling Great Room with abundant windows, a gas fireplace, dining area, breakfast bar kitchen, convenient half bath, and a spacious deck for seamless indoor-outdoor living. There's also a sweet view of the Monument in the distance. The first floor offers a generous primary bedroom and two guest bedrooms, each with en-suite baths, while a striking two-story foyer welcomes you home and leads to a home office. The walk-out lower level includes a large den, full bath with laundry, garage access, and sliding doors opening to a secluded side patio. Beautifully landscaped, irrigated grounds with raised garden beds, stone walls, and an outdoor shower create an inviting setting. A whole-house sound system, newly installed motorized window treatments, an attached garage, and exceptional natural light complete this rare offering. Just over a mile from Herring Cove Beach.

20 Bayberry Avenue, Provincetown

21 Pleasant View Drive, Orleans
$3,999,999
3 Beds ⋅ 4 Baths ⋅ 22601200 MLS
This stunning new contemporary home by Eastward Companies is nearing completion. Designed to embrace the unique topography and natural setting, it overlooks a flourishing natural hollow. The three levels of living space offer immersive views of the surrounding native flora, further enhanced by a comprehensive natural landscape plan. Walls of south-facing windows and multiple decks offer quiet spaces and tranquil vistas. The great room encompasses the first floor, ideal for gatherings. The natural wood chef's kitchen is a striking complement to the sleek lines and kerfed windows of the living and dining space. Upstairs are two guest bedrooms and a stylish primary suite with fireplace and private deck. The fixtures, finishes and workmanship throughout are superb. The lower walkout level is for media, games, and access to the inground plunge pool with its private granite patio, outdoor shower and gas fire pit. Watch the stars or the amazing variety of birds and wildlife that visit. Coupled with a superb Briar Springs Hills address, an area loved by walkers for generations, this property presents the ultimate Cape retreat or year-round home.

21 Pleasant View Drive, Orleans

2 Huckleberry Drive, Orleans
$1,875,000
4 Beds ⋅ 4 Baths ⋅ 22603497 MLS
NEW PRICE! Set on a beautifully landscaped 1.11-acre corner, this custom-built Cape offers timeless design, exceptional craftsmanship, and a remarkably flexible floor plan designed to adapt through every stage of life. Whether enjoyed as a weekend retreat today or a full-time residence in the years ahead, this is a home created for effortless entertaining, quiet retreat, and years of memorable gatherings. Built in 2002 and meticulously maintained by its original owners, the residence offers more than 3,200 square feet of thoughtfully designed living space, including four bedrooms, three full baths, an oversized attached two-car garage, and an expansive unfinished lower level offering outstanding potential for future recreation, fitness, hobbies, a workshop, or abundant storage. One of the home's most distinctive features is its private flex suite, accessible both through the main residence and its own entrance via the mudroom. Complete with a bedroom, living area, and full bath, this versatile space is ideal for extended guests, multigenerational living, a private home office, creative pursuits, or other evolving lifestyle needs. At the heart of the home, the dramatic living room is anchored by soaring coffered ceilings, custom built-ins, and a gas fireplace, creating an inviting gathering space for everyday living and special occasions alike. An enclosed sunroom extends from both the living room and the private first-floor primary suite, opening onto an expansive terrace surrounded by mature gardens and thoughtfully designed outdoor living areas that blur the line between indoors and out. The spacious eat-in kitchen features cherry cabinetry, granite countertops, generous pantry and laundry space, and easy access to the terrace, while a separate formal dining room provides an elegant setting for intimate dinners and festive celebrations. The private first-floor primary suite offers the ease of single-level living, while two generously sized guest bedrooms upstairs share a Jack-and-Jill bath, providing comfort and privacy for visitors. Additional highlights include a new radiant heating system, multiple newer mini-split systems, an outdoor shower, private irrigation well, mature landscaping, a four-bedroom septic system, and the added benefit of being located outside the flood zone. Ideally located near Pleasant Bay, conservation lands, scenic walking trails, town landings, and the shops and restaurants of Orleans, the property offers a rare combination of privacy, flexibility, and enduring quality in one of the Lower Cape's most sought-after settings. Thoughtfully designed for the way people live today--and the lives they envision tomorrow--this is a home that will serve beautifully for years to come.

2 Huckleberry Drive, Orleans

2 Huckleberry Dr, Orleans
$1,875,000
4 Beds ⋅ 4 Baths ⋅ 73552043 MLS
NEW PRICE! Set on a beautifully landscaped 1.11-acre corner lot in desirable South Orleans, this custom-built Cape offers timeless craftsmanship, exceptional privacy, & a remarkably flexible floor plan designed to adapt through every stage of life. Whether enjoyed as a weekend retreat today or a full-time residence in the years ahead, this is a home created for effortless entertaining, quiet retreat, & years of memorable gatherings. Built in 2002 & meticulously maintained by its original owners, the residence offers more than 3,200 square feet of thoughtfully designed living space, including 4BRs, 3 full & 1 half BAs, an oversized attached 2-car garage, & an expansive unfinished lower level offering outstanding potential for future recreation, fitness, hobbies, a workshop, or abundant storage, One of the home's most distinctive features is its private flex suite, accessible both through the main residence and its own entrance via the mudroom. Complete with a BR, living area, & full BA, this exceptionally versatile space is ideal for extended guests, multigenerational living, private home office, creative pursuits, or other evolving lifestyle needs. At the heart of the home, the dramatic living room is anchored by soaring coffered ceilings, custom built-ins, & gas fireplace, creating an inviting gathering space for everyday living & special occasions alike. An enclosed sunroom extends from both LR & private first-floor primary suite, opening onto an expansive terrace surrounded by mature gardens & thoughtfully designed outdoor living areas. The spacious eat-in kitchen features cherry cabinetry, granite countertops, generous pantry & laundry space, & easy access to the terrace, while a separate formal dining room provides an elegant setting for intimate dinners & festive celebrations.The 1st-floor primary suite offers the ease of single-level living, while 2 generously sized guest bedrooms upstairs share a Jack-&-Jill bath, providing comfort & privacy for visitors. Additional highlights include a new radiant heating system, multiple newer mini-split systems, outdoor shower, private irrigation well, & mature landscaping. Ideally located near Pleasant Bay, scenic walking trails, town landings, & destination shops & restaurants, the property offers a rare combination of privacy, flexibility, and enduring quality. Thoughtfully designed for the way people live today—& the lives they envision tomorrow—this home will serve beautifully for years to come.

2 Huckleberry Dr, Orleans

9 Broadview Ave, Berkley
$695,000
3 Beds ⋅ 3 Baths ⋅ 73554970 MLS
Imagine Being moved in by the holidays and celebrating the holidays in your new home Welcome to this beautiful 3-bedroom, 2.5-bathroom home tucked away on a quiet dead-end street in Berkeley, MA, where charm, comfort, and privacy come together! From the moment you step inside, you’ll be captivated by the soaring ceilings, beautiful hardwood floors, and inviting open-concept layout that creates the perfect balance of warmth and functionality. The spacious living room features a gorgeous fireplace, making it the perfect place to unwind, while the remodeled kitchen showcases modern finishes and a sleek stainless steel range hood that adds a stylish touch. Imagine starting your mornings on the wraparound porch, sipping your coffee while enjoying partial views of the Taunton River. It’s the perfect spot to relax, entertain, and take in the peaceful surroundings!The fully finished basement offers incredible additional living space, complete with its own full bathroom and a separate walkout entrance leading directly to the backyard. Whether you envision a guest retreat, recreation room, home office, or flexible living space, you have the freedom to make it your own! Outside, enjoy the privacy of a fenced-in backyard, a spacious storage shed, and a large, detached garage that’s perfect for the handyman, hobbyist, or anyone looking for extra room for projects and storage. Message me for a private showing! Some photos were used with Ai to Enhance the photo.

9 Broadview Ave, Berkley

20 Burg Ave, Sandwich
$979,000
2 Beds ⋅ 2 Baths ⋅ 73548875 MLS
Million-dollar views! Coastal dreams come to life in this contemporary Town Neck gem, where the iconic white picket fence welcomes you home to one of the most breathtaking settings on the marsh. Come for the views; stay for the happily-ever-after! This two-bedroom, two-bath retreat is a masterclass in light and design, featuring an airy open floor plan framed by premium Andersen windows that invite the outside in. The heart of the home is a bright, sparkling kitchen outfitted with elegant Martha Stewart cabinetry, flowing effortlessly into the living area where a stunning stone fireplace serves as a cozy centerpiece for cool evenings. The primary suite is a private sanctuary complete with a luxurious steam shower. Outside, the expansive deck offers a front-row seat to nature’s theater, boasting incredible views and sunrises that paint the sky over the marsh each morning. With a one-car garage and a location that captures the very best of the coastal lifestyle, this home is a rare blend of charm and fun. Close to so many amenities: the iconic Sandwich Boardwalk, Town Neck Beach, Sandy Neck Beach, the Canal, the Sandwich Marina, several restaurants, Sandwich Village, Heritage Museum and Gardens, and so much more. Experience the magic of the marsh and the best of Cape Cod!

20 Burg Ave, Sandwich

4 Holly Rd, Marshfield
$1,585,000
3 Beds ⋅ 4 Baths ⋅ 73550574 MLS
TWO NEW DEVELOPMENTS in the works for this architectural beauty!! 1.). FIRST PUBLIC OPEN HOUSE SATURDAY, OCTOBER 10TH 11-1. 2.). SELLER IS NOW OFFERING A $25,000 INCENTIVE FOR BUYERS TO USE AT THEIR DISCRETION. Create your own coastal masterpiece in one of Marshfield's most desirable seaside neighborhoods. Nestled in the sought after Ferry Hill neighborhood, just minutes from Humarock Beach, this extraordinary post & beam residence offers a rare opportunity to complete a truly one of a kind home while making the final design choices your own. Created to embrace its breathtaking setting, the home features dramatic walls of glass, spanning 1st and 2nd floors, flooding the interior with natural light and capturing stunning water views. The striking post & beam architecture creates soaring ceilings, timeless character and an architectural presence rarely found in new construction. Approximately 75% complete, come fall in love with this coastal masterpiece & personalize the finishes and details. Whether you desire a year round coastal retreat, or a water view inspired getaway, 4 Holly Road is your opportunity to bring your vision to life. Walk to beaches, boutiques and restaurants. Welcome home!!!

4 Holly Rd, Marshfield

44 Prices Way, Edgartown
$1,395,000
3 Beds ⋅ 2 Baths ⋅ 73549401 MLS
Contemporary Island Retreat - A smart opportunity for buyers seeking a low-maintenance Vineyard home near Edgartown Village, this contemporary retreat offers convenient access to shopping, services and the bike path connecting the three down-Island towns. Ideal as a year-round residence, seasonal getaway or potential vacation rental, the home features an open living and dining area, efficient kitchen and welcoming living room with wood-burning fireplace. Outdoor living includes a sunny south-facing front deck, newer rear deck for grilling and dining, and a second-floor balcony perfect for morning coffee. Natural landscaping keeps upkeep simple, while a detached Party/Game Shed with French doors opens to the backyard and firepit area, offering flexible bonus space for entertaining, remote work or relaxing after a day at the beach or in town.

44 Prices Way, Edgartown

30 Fairway Road, Yarmouth
$999,999
3 Beds ⋅ 2 Baths ⋅ 73548767 MLS
It's all about location with this South Yarmouth home! A rare combination of a private beach, two docks, mooring opportunity, and the Bass River Golf Course all around the corner. This classic ranch-style home offers untapped potential. Plant your roots in one of Cape Cod's unique neighborhood associations. As a member of the Salt Box Association, you'll enjoy deeded rights to a private sandy beach on beautiful Bass River and two docks. Set on a peaceful street with that unmistakable Cape charm, the property boasts an open floor plan, three bedrooms, and bonus spaces. There are solar panels, a generator, irrigation, decks, and beautiful gardens. Whether you're dreaming of an open-concept kitchen or refreshed baths, this home offers the flexibility to make it truly your own. Spend mornings on the Bass River golf course just around the corner, afternoons on the water, and evenings exploring everything Cape Cod has to offer.

30 Fairway Road, Yarmouth

55 Winterset Drive, Chatham
$2,245,000
4 Beds ⋅ 4 Baths ⋅ 73548377 MLS
Exceptional Great Hill Estates retreat being offered fully furnished, set on 1.8 private acres with deeded rights to Lover's Lake for kayaking, swimming, and canoeing just a short foot path away. Located on a scenic corner lot, this 4-bedroom, 3.5-bath home offers peaceful natural surroundings and room to relax both inside and out. A first-floor primary suite features ensuite bath and laundry for convenient single-level living. The heart of the home is a spacious kitchen with a large island, dining area, and adjacent great rooms with vaulted beamed ceilings and fireplaces. A wraparound deck, perfect for outdoor dining, entertaining, or simply enjoying the views. Upstairs are two bedrooms and a full bath, including one bedroom with a fireplace and sitting area that offers a private retreat-like feel. The walk-out lower level features a fourth bedroom, full bath, another laundry area, and direct access to a stone patio with custom seating and gas fire pit. Additional highlights include central ac, hardwood floors, two-car attached garage and new Bosch heating system. Close to Chatham Village, Lighthouse and Hardings beaches, bike path and tennis courts.

55 Winterset Drive, Chatham

155 Elmer St, Pembroke
$750,000
3 Beds ⋅ 2 Baths ⋅ 73548106 MLS
Move in ready! Wide open-concept home featuring a breathtaking great room with soaring 16-foot vaulted ceilings and spectacular private 180-degree views of town owned conservation land that will never be developed. Designed for both comfort and entertaining, the gourmet kitchen offers an oversized 10-foot island, gas cooktop and double wall ovens. The spacious primary suite features a luxurious bath with dual vanities, a five-foot walk-in shower, and a private loft space ideal for a home office or relaxation.Enjoy outdoor living on the expansive wraparound deck, perfect for entertaining or taking in the peaceful wooded setting. Situated on nearly an acre abutting private woods, there is plenty of room to add a pool or detached garage. Additional highlights include an upgraded septic system sized for future expansion, a 1,400 sq. ft. unfinished walkout basement with high ceilings and great ADU potential, large storage shed, and an oversized driveway with ample off-street parking.

155 Elmer St, Pembroke

96 Hammett Ln, Chilmark
$3,795,000
3 Beds ⋅ 4 Baths ⋅ 73545525 MLS
Beautifully designed and built Post & Beam style home is tastefully thought out and meticulously maintained. The open living, dining and kitchen feature custom built-ins, a wood burning fireplace and a fabulous gourmet kitchen with Wolfe 8 burner professional style stove, Sub Zero refrigerator, Boshe dishwasher, soapstone counters and a butlers pantry with extra cupboards, shelving and a wine refrigerator. There are sliders that take you to an oversized deck and stairs to a blue stone patio and beautiful gardens. The screened-in porch off the living room steps out to the side yard, patio and outdoor shower. First floor Primary with walk-in closet, access to the deck and a private en-suite bathroom with beautiful tiled steam shower and large soaking tub. Second floor includes a loft with sitting room, 2 spacious bedrooms that share a full bath with shower and office, all with cathedral beamed ceilings. Many nice features throughout include white oak random width floors, marble and tile.

96 Hammett Ln, Chilmark

64 Christiantown, West Tisbury
$3,495,000
4 Beds ⋅ 4 Baths ⋅ 73544561 MLS
This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home offices, this residence offers perfect versatility for modern living—whether you require a quiet library or a remote workspace. Step outside onto the welcoming farmer’s porch to take in the beautifully manicured grounds, complete with lush perennial gardens supported by an irrigation system. The backyard serves as a true resort-style retreat, complete with an expansive in-ground pool and a hot tub spa, cabana as well as an enclosed outdoor shower. A cobblestone-lined circular driveway leads to ample guest parking and an attached two-bay garage. Combined with a full, versatile basement, this property is a rare find for the discerning buyer. Ideally situated just one mile from Up-Island Cronig's and local conveniences, you are also moments away from Cedar Tree Neck and the private town beauty of Lambert’s Cove Beach. Your sanctuary awaits. $3,495,000.

64 Christiantown, West Tisbury

70 Menauhant, Falmouth
$2,695,000
5 Beds ⋅ 4 Baths ⋅ 73544315 MLS
Spectacular water views from nearly every room! Breathtaking sunrises and sunsets overlooking Vineyard Sound, Bristol and Falmouth Heights Beaches, and Little Pond. This home offers one of the finest vantage points in town for enjoying the Fourth of July fireworks. Offered for the first time in over 100 years, this exceptional property combines timeless character with comfortable living. Rebuilt in 1992, two properties were combined and the structure was raised 14 ft., providing for a garage and basement. The convenience of one floor living is provided with an elevator, first-floor bedroom suite, and first floor laundry. Multiple living spaces are provided for entertaining family and friends. The sun-filled sunroom is the perfect place to start your morning. Additional features include a two-car garage, wrap-around deck, and a private yard ideal for summer enjoyment. Mechanicals on first and second floors. New 2000-gallon septic tank installed in 2026. Passing Title V in hand.

70 Menauhant, Falmouth

27 Double Ox Rd, Oak Bluffs
$3,400,000
3 Beds ⋅ 5 Baths ⋅ 73542323 MLS
Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living areas. Upstairs are two additional bedroom suites, a loft-style family room/office, dedicated laundry, and flexible bonus room ideal for guests, media, or recreation. A screened porch, covered outdoor living spaces, and attached two-car garage enhance both functionality and lifestyle. Built with high-end finishes and attention to detail throughout, this stunning new construction offering presents an opportunity to own a luxury retreat with easy access to Oak Bluffs' beaches, harbor, restaurants, shops, and all the attractions that make the Vineyard such a sought-after destination.

27 Double Ox Rd, Oak Bluffs

44 Carey Lane, Falmouth
$4,625,000
4 Beds ⋅ 4 Baths ⋅ 73542241 MLS
Waterfront contemporary luxury on a private lane in the coveted enclave of Quissett Harbor. Blending architectural distinction with coastal serenity, this exceptional 4BD/3.5BA residence offers light-filled living spaces designed for both everyday comfort and elegant entertaining. Soaring walls of glass and sun-filled interiors create a seamless connection to the surrounding landscape. The private primary suite wing features a study, walk-in closet, and expansive floor-to-ceiling windows. A separate bedroom wing offers two spacious guest rooms, while the second-floor guest suite provides flexible space for visitors, a home office, or artist’s studio. Upgrades include native plant landscaping with new irrigation, new furnaces, and new roof. Two minute walk from scenic harbor offering a full service marina and yacht club. Adjacent is a nature preserve with hiking trails and secluded sandy beach. Unlimited recreation of sailing, kayaking, swimming at a private beach club, and nearby golf.

44 Carey Lane, Falmouth

30 Starr Ln, Rehoboth
$1,895,000
5 Beds ⋅ 5 Baths ⋅ 73540993 MLS
Prestigious New Construction Estate in an Exclusive Gated Community Nestled atop a private 3.63-acre hilltop lot, this exceptional 5-bedroom, 4.5-bath luxury home offers panoramic views, half ownership of a scenic pond, and unmatched privacy. The thoughtfully designed open-concept floor plan features 9-foot ceilings, wide-plank white oak flooring, abundant natural light, and 3,000 sq. ft. of elegant living space, plus a 1,750 sq. ft. basement plumbed for a future full bath. The gourmet chef's kitchen boasts quartz countertops, premium stainless appliances, a 48-inch gas range, a 5'x10' island, and a walk-in pantry. The luxurious primary suite offers a spa-inspired bath with a freestanding tub, oversized shower, dual vanities, and a spacious walk-in closet. Additional highlights include two gas fireplaces, a 3-car garage, whole-house water filtration, a 1,000-gallon underground propane tank, energy-efficient construction, and premium finishes throughout. Luxury andelegance awaits.

30 Starr Ln, Rehoboth

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