luxury houses with pool for sale Massachusetts, United States (page 5)

Shay Terrace presents a rare opportunity to build a custom luxury home in one of Newburyport’s newest and most exclusive enclaves. Offering just four builder tie-in homesites, this thoughtfully designed private lane combines an exceptional location with the craftsmanship and reputation of premier local builder. Homesites ranging from 12,000 to 21,000 square feet are available starting at $899,000, with fully custom luxury residences starting at $2,999,000. Collaborate with an experienced builder to design and build a home tailored to your lifestyle, from architectural design and floor plan to the finest finishes and personalized details. Located just minutes from downtown Newburyport, waterfront parks, marinas, boutique shopping, acclaimed restaurants, and Plum Island’s beautiful beaches, Highland Court offers an unmatched combination of privacy, convenience, and coastal New England living. Photos are of the builders previous work. Reach out for reservation details and next steps.

This architectural gem has been carefully restored and enhanced to exceptional standards, preserving its storied heritage while seamlessly integrating contemporary conveniences. The exceptional property features an elegant Main House, inviting Guest Cottage, Potting Shed/Studio and Barn. Framed by breathtaking panoramic vistas, the estate showcases classic stone walls, a serene spring-fed pond and a heated saltwater pool. The impeccably maintained lawns and expertly designed grounds establish a pristine country retreat. Premium upgrades include superior rock wool insulation throughout. Perfectly positioned just minutes from Tanglewood's celebrated performances, fine dining and thriving cultural attractions in the Berkshires.

A Sanctuary of Sustainable Elegance Nestled within nearly 36 pristine acres of rolling Western Massachusetts landscape, this newly completed custom estate represents a historic shift in high-end residential design: a masterclass in "quiet luxury" intersecting with uncompromising environmental stewardship. Conceived on a dual mandate of absolute sustainability and personal restoration, the property was custom-built by the region's premier sustainable builder, Wright Builders, with architectural design by Maple Street Architects. Every detail was guided from inception to serve as a profoundly calm, healthy, and private lifestyle. The Main Residence: Materiality & Well-Being The architectural narrative centers entirely on longevity and human wellness. Built with strictly eco-friendly, non-toxic materials and a zero-VOC footprint, the home offers a completely breathable, clean living environment. Inside, the open-concept floor plan is flooded with incredible natural light, framing panoramic views of the estate's private, gated acreage. The design artfully layers contemporary lines with a warm, tonal color palette and exceptional artisanal finishes. The primary wing serves as a secluded sanctuary featuring a private balcony overlooking the pristine grounds, a massive walk-through closet, and a spa-inspired bath complete with a deep stone soaking tub and heated flooring. The Lower Level: A Wellness & Entertaining Hub The expansive walkout lower level acts as a self-contained wellness retreat and entertainment center, transitioning seamlessly to the outdoor landscape through massive triple sliders that disappear completely into the walls. This level features a custom-crafted, thermally modified aspen wood sauna controlled via smart-app connectivity, a dedicated home fitness studio, and an executive home office. For media and leisure, a finished game room boasts a professional theater-grade audio matrix and a dynamic 100-inch display. Steps away, a hidden, secondary caterer's kitchenette equipped with integrated Sub-Zero, Wolf, and Cove appliances ensures seamless poolside hosting. The Grounds, Recreation & The Automotive Barn The estate grounds are a paradise of private recreation and total anonymity. Step outside to a flawless limestone-paver pool deck hosting a custom gunite saltwater pool and an attached spa engineered for year-round independent operation. The adjacent covered patio offers true three-season utility, enclosed by motorized, retractable Phantom screens, an outdoor fireplace, and a built-in stone kitchen equipped with a Traeger Timberline XL and Blackstone griddle. For the hobbyist or collector, the crown jewel of the acreage is a detached, 3,400-square-foot climate-controlled luxury outbuilding. Styled with high-end modern Hex Grid LED lighting, this space features professional infrastructure and dedicated panels for dual Rotary automotive lifts, an adjustable, interactive indoor climbing wall by LEMUR Design featuring a synced Kilter Board system, and abundant space for recreational vehicles Advanced Infrastructure, Discretion & Peace of Mind Behind the organic aesthetic lies a highly engineered, resilient infrastructure designed for total self-reliance, privacy, and effortless living. Discretion is paramount throughout the estate; a private gated entrance introduces the property, supported by a state-of-the-art security and access control system designed to ensure complete peace of mind and personal sanctuary. The home's intuitive smart-automation system seamlessly manages all lighting, shades, multi-zone HVAC, and an invisible multi-room ceiling speaker network with absolute ease. This advanced living environment is further supported by a massive 22.8 kW grid-tied solar PV array by PV Squared, paired with dual automatic standby propane generators to ensure uninterrupted, whole-property backup power under any circumstance. Shown by appointment.

This gorgeous Contemporary Cape offers an exceptional open floor plan with spacious rooms and a spectacular outdoor entertaining area featuring an in-ground pool and separate cabana. The first floor features a dramatic great room with a fireplace, cathedral ceilings, and a breakfast nook that opens to the large center island kitchen. The living and dining area offers sliders leading directly to the pool. The first-floor primary suite boasts a cathedral ceiling, a spacious bath with custom built-ins, and ample closet space. Also on the main level are a powder room, a welcoming tiled foyer, and a convenient laundry room. The second floor includes a private guest suite over the garage, two additional guest bedrooms, and a third full bathroom. The finished lower level offers a large family room, providing additional living and recreation space. Outside, enjoy the approximately 20' x 40' vinyl-lined, fenced in-ground swimming pool surrounded by a private backyard that abuts protected conservation land. The detached cabana is an entertainer's dream, complete with an indoor/outdoor bar, powder room, sitting room, and outdoor shower. Numerous updates including roof, HVAC, and more.

Experience the luxury of gracious proportions, impeccable details, and stunning design in this exquisite classical villa that would be as at home in Italy as it is in the Berkshire landscape. Protected views of mountains, rolling hills, and meadows surround the 6.9-acre estate. The atmosphere of sophisticated luxury begins with the approach through an allee of willow trees and in the front courtyard, edged with stately Bradford pear trees and arbor vitae and anchored by the 2716sf, single-level residence and a matched pair of outbuildings--a two-car garage and a garden house. The front entry of architect-designed residence leads to a luminous interior with tall ceilings, reflective white walls, generous windows and 19 screened French doors that welcome sunlight and breezes and provide for ideal interior-exterior living. To the left of the entry are a living room with a wood-burning Rumford fireplace and hallway to the primary suite with an airy, comfortable bedroom, refined, restorative bath, and walk-in closet/dressing room. To the right, a spacious dining room, well-appointed kitchen, screened porch, and hallway to two bedrooms and full bath. The U-shaped floor plan embraces a secluded formal garden, reflecting pool with fountain, patio with pergola, and 40' lap pool. Completed in 1998, every element of the residence attests to architectural intelligence, superior craftsmanship, and love for the bucolic landscape. The high level of quality is evident in the visually commanding millwork, true stucco exterior, lath-and plaster walls in the principal rooms, east and south pergolas, west-facing screened porch, and sensitive choreography of space. With roots in the classical architecture of ancient Rome, this is a thoroughly modern dwelling replete with whole-house fan, air conditioning, generator, security system, 630-foot drilled well, and chef-ready appliances. The result is a home that feels both sculptural and deeply connected to its setting. With protected views, total privacy, and proximity to South County amenities (7 minutes to Guido's), this is a rare Berkshire offering -- serene, architecturally stunning, and eminently livable.

Your Turnkey Cape Cod Oasis and Income Generator has Arrived. Why wait for a ''dream home'' to be built when you can walk into one today? Set on a private acre, this isn't just a house--it's a high-end lifestyle package. Whether you're looking for a serene primary residence or a powerhouse investment, this 4 bedroom, 4.5 bath, new construction masterpiece comes fully furnished and ready to perform from Day One. Double the Luxury: This layout features two massive primary ensuites, each boasting spacious walk-in closets--perfect for multi-generational living or high-end rental appeal. Elevate your culinary game with a professional-grade Thermador range and oven, the centerpiece of a sun-drenched, open-concept heart of the home. Skip the furniture lead times; every inch of this home has been styled for comfort and coastal elegance. A shimmering pool is included, transforming your oversized lot into a private summer resort. With a rental permit in place, you can tap into the Cape's lucrative short-term rental market immediately. Tucked away in a tranquil, peaceful setting, you are just minutes from easy access to the walking trails of Thompsons Field and Cape Cod Rail Trail.

Nestled along scenic Main Street in Townsend, this beautifully updated New England home seamlessly blends timeless character with modern comfort. Rich in charm and architectural detail, the property features expansive gathering spaces, multiple fireplaces, exposed beams, and a dramatic vaulted great room filled with natural light. The renovated kitchen offers a clean, modern aesthetic complete with a large center island ideal for entertaining and everyday living. A flexible floor plan provides endless possibilities for multigenerational living, working from home, or creating dedicated recreation and lounge spaces. Adding even more potential, the unfinished bonus space above the oversized two-car garage is ready to be transformed into a studio, game room, guest suite, or additional living area tailored to your needs.

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody and Stearns, this Florentine palazzo features stunning grounds by Frederick Law Olmsted. Former home to the Boston Symphony Orchestra and moments from Tanglewood, this 25,000+SF architectural sanctuary seamlessly marries timeless grandeur with 21st-century luxury. The majestic layout boasts a soaring Great Hall, a formal dining room, a refined wine cellar (6,500-bottle capacity), and 19 uniquely curated bedroom suites. Breathtaking porticos frame panoramic vistas, while rolling lawns and mature gardens present paths to the pool and tennis court. This iconic estate offers utmost privacy, a deeply rich cultural heritage, and unmatched Berkshire elegance.

These lots don't come available that often. Steps to the Association beach at the end of Longhill Drive. Enjoy beautiful sunsets after a day of swimming in Cape Cod Bay. With just shy of an acre of land the opportunities are endless. This lot has been engineered and cleared. Bring your ideas to begin creating your Northside Beach Home.

Located in Stockbridge, this historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Who could ask for anything more?

Set across three private acres in Eel Point, 36 Warrens Landing Road is a rare Nantucket estate completed in 2017. This remarkable seven-bedroom compound pairs exceptional craftsmanship and sophisticated design with an extraordinary sense of scale, privacy, and connection to the landscape. Elevated views extend toward Madaket Harbor and the ocean, while expansive lawns, mature landscaping, and a resort-like pool and spa create an exceptional setting for island living. More than 3,900 square feet of meticulously designed outdoor entertaining space offers multiple settings for relaxation and gatherings. A gracious screened-in porch, covered porches, expansive decks, and a generous patio provide spaces for morning coffee, sunset cocktails, poolside gatherings, and elegant al fresco dining, all thoughtfully positioned to embrace Nantucket’s western views. The 6,488-square-foot main residence is complemented by a distinctive indoor/outdoor pool house with dual cabanas and an oversized two-car garage with a finished studio above. Thoughtfully orchestrated architecture and grounds create a private compound equally suited to intimate family gatherings and grand-scale entertaining. More than a residence, 36 Warrens Landing Road is an exceptional Nantucket retreat where architecture, landscape, and the island’s natural beauty converge.

If you are seeking space, privacy, and effortless living you have found your home. Set in one of Duxbury’s most sought-after locations, just moments to Duxbury Bay and the heart of the village a rare combination of privacy and location. Expansive one-level living offering a seamless indoor-outdoor connection. Designed to capture the beauty of its surroundings, walls of glass overlook professionally landscaped grounds and a stunning in-ground pool, natural light fills this home throughout the day. A dramatic entry with cathedral ceiling sunken living room w/floor-to-ceiling brick fireplace, entertainment-sized kitchen opens to vaulted family room all thoughtfully connected leading to outdoor terraces and gardens. The home features four bedrooms, each with its own private bath, a spacious and secluded primary suite. The walk-out lower level adds exceptional flexibility with large recreation and mud rooms, full guest suite and or office. Pack your bags, you're home.

A Legacy Preserved: Introducing "The George Gabriel House," An Iconic Richmond Heights Estate Step into a piece of Worcester's history with "The George Gabriel House," a residence that stands as one of the earliest and finest in the coveted Richmond Heights neighborhood. This magnificent historic home, boasting 7 bedrooms, 5 bathrooms, and approximately 5,000 square feet of living space, offers an unparalleled opportunity to own a true landmark. From the moment you enter, you'll be captivated by the home's rich heritage and exquisite original details. Imagine entertaining amidst high ceilings, preserved moldings, bathed in the soft glow filtering through leaded glass windows. The heart of the home is a European-inspired chef's kitchen, seamlessly blending modern luxury with timeless charm. Granite countertops, professional-grade stainless steel appliances, and a sun-drenched breakfast nook create an inviting space for culinary creations and casual gatherings. Multiple living areas provide a sophisticated flow for both formal occasions and relaxed family living. Host elegant soirees in the formal living rooms and grand dining room, find inspiration in the distinguished study, or unwind in the expansive great room, anchored by a warm and inviting fireplace and offering seamless access to the outdoor oasis. Step outside to discover a private retreat designed for enjoyment. A sparkling gunite pool beckons on warm days, complemented by an attached Jacuzzi tub for ultimate relaxation. The patio provides ample space for al fresco dining and entertaining, surrounded by the beauty of mature perennial flower beds and shrubs. The thoughtfully finished basement extends the living space with a vibrant game room, a fun "speakeasy-style" bar perfect for entertaining, and stone fireplace. A convenient walkout provides direct access to the lush backyard. Throughout the home, gleaming maple hardwood floors add warmth and character. Practicality meets prestige with a two-car garage featuring an attached utility shed. "The George Gabriel House" is more than just a residence; it's a testament to a bygone era, thoughtfully updated for modern living. This is a rare opportunity to own a significant piece of Worcester's architectural history in one of its most desirable locations.

High on a hilltop in the Southern Berkshires stands East Hill Farm. 227 cultivated acres encompassing pristine forest, a spring-fed pond, a striking barn, verdant pastures, formal and vegetable gardens, a pool, and a tennis court. The centerpiece: a 1798 Georgian home, 5,000 SF with 5 bedrooms. Ready for private living, entertaining, horses, farming, a bespoke destination, or simply: tranquility. Includes a reimagined 6,000+ SF guest house, once an Arabian horse barn. 2½ hours to both NYC & Boston, yet a world apart. East Hill Farm offers what money rarely can buy: authenticity at scale. A 227 year-old house expanded, refined for 21st century life. Land, privacy, history, and a place of peace, which has endured through every chapter of American history. The next chapter begins with you. Reach out! Where The World Falls Away--227 acres. 227 years. One extraordinary hilltop farm. Drive up East Hill Road through Southfield village, past the store, climbing toward the top of Woodruff Mountain. The dirt road is well-maintained and lightly traveled. Sugar maples line your approach--massive, ancient trees that have watched over this land since before the house was built. Behind them, set back from the road, stands the kind of barn that makes photographers stop their cars. Three and a half stories of hand-hewn timber, painted proper New England red, moved here piece by piece from Amherst, Massachusetts, because the sellers understood that a farm needs a real barn. Not a replica. The real thing. The House Stops Your Heart--Federal period, 1798, when John Adams was president. This wasn't just another farmhouse. When Thomas Shepard commissioned John Collar to build this, he was making a statement. 8 rooms. 5 fireplaces. Ceilings higher than any farmer needed. Those distinctive 12-over-12 windows with hand-blown glass that turns the morning light liquid. A facade with sidelight windows and dentil cornice that announced to every traveler: here lives a person of substance. Walk through that front door and the wide center hall opens before you. Original wide-plank floors--King's boards, they called them, because timber this wide was supposed to be reserved for the Royal Navy's masts. Twin parlors flank the entrance, flooded with southern light. To your left, the original keeping room, now the dining room, where that massive cooking fireplace with its beehive oven still works perfectly after 227 years. The draft in these fireplaces is extraordinary. The woodwork throughout is original or crafted by hand precisely to match. Chair rails, wainscoting, built-in china cabinets with their original hardware. Those small cupboards tucked around the chimneys--John Collar's signature touch. Five Families in 227 Years--Jesse Hartwell married Thomas Shepard's niece and turned the house into a meeting place for progressive thinkers, and through the 19th century, the Hartwell family made this their home. Then came the Arabian horse breeders in the 1930s who added the newer rear ell and built what's now the guest house. The current sellers bought the house and five acres in 1969, then spent the next five decades not just restoring but thoughtfully expanding it. You'll be only the fifth resident to call East Hill Farm home--and despite its National Register status, free to shape its future as you see fit. That newer section? Radiant heat underfoot, a proper mudroom with laundry, a family room or perfect home office with its own kitchen, and an elevator up to a sun-filled library with built-in shelves and an ensuite bedroom and bath. A luminous sunroom framing year-round sunsets, with sweeping views across the formal gardens, horse pastures, and the shimmering pond below. Upstairs in the original part of the house, an additional four bedrooms, each with its own character. The canopy bedroom with its blue and white toile--that's not staging, that's how the family lives. Wide hallways, deep closets, and in that large upstairs hall above the front door, a perfect spot to sit and read while gazing out the neoclassical window over your barn, fields and forest, mountains in the distance. 5 full and 1 half baths in all--some original 1930s with their good bones, others from the 1980s restoration. The kitchen? Also 1980s, completely functional with good counter space, and a working wood-fired stove alongside modern appliances. Morning light streams in from the east, and sunset views are to the west, opening onto fieldstone patios on either side. Everything works: oil heat from a Viessman German boiler, cedar shake roof (much replaced in 2021), private well water so good they've bottled it up for guests, backup generator, fiber internet. The bones are so good and the mechanicals so solid that you can move in tomorrow or update to your taste--the house won't fight you either way. 227 Acres: A Complete World--East Hill Farm is more than the sum of its parts. From the original five-acre homestead, the current owners lovingly reunited land to create the breathtaking 227-acre estate it is today. 154 acres stretching across the north side of East Hill Road, and 73 tranquil acres to the south. To the north, a substantial portion of the property borders Sandisfield State Forest and thousands of acres of protected land. To the south, you have a section along Hotchkiss Road that is part of the New Marlborough Land Trust. Each acre is part of a dream fulfilled, a landscape that invites endless exploration and inspiration. Walk west from the kitchen patio between the formal gardens. Brick paths wind through perennial beds: heritage roses, peonies, iris. A long row of prolific blueberry bushes. In the vegetable garden, established asparagus and rhubarb come back stronger every year. Passing that perfect garden shed with its slate roof, as mist rises off the pond, becomes part of your morning coffee stroll. The pond--almost four acres, brook-fed, crystal clear. The family created it, and for decades it's been their private swimming hole, sailing spot, fishing paradise. Circle the pond and you'll find the big fishing rock on the west side, the perfect swimming spot on the east. Or head into the forest. Miles of trails, including a loop road that connects to Sandisfield State Forest. In spring, Lee Brook, the largest of several on the farm, roars with snowmelt. Up where the brook crosses the trail, it forms a waterfall after a hard rain. These are the headwaters of the Whiting River, and you own it. This isn't just acreage - it's a complete ecosystem. Meadows, forests, water, gardens, pastures, each flowing naturally into the next. Built for Whatever You Dream--That magnificent barn across the country road--3,550 SF on a full stone foundation, electricity, running water, lower level for equipment, main floor with stalls and work rooms, massive hay loft. Four pastures with water sources, run-in barns with power and water, and additional smaller outbuildings. The infrastructure is thoughtfully designed, whether your dreams include horses, alpacas, heritage sheep, a flourishing market garden, an orchard, festive celebrations, a tranquil retreat center, or simply savoring the seasons as they change across your land. The guest house tells its own story. Built as stables for those 1930s Arabians, it's now 6,668 SF divided into four independent residences, with cathedral ceilings and fireplaces. Some would use this for multi-generational living. Others might see a writers' or artists' retreat, a wedding venue, or wellness center. The bones are spectacular--soaring spaces and abundant light. Morning swims in the sparkling gunite pool with its serene fieldstone waterfall. Afternoons spent on the newly resurfaced tennis court. Evenings wandering down to the pond, soaking in the tranquility. Or embrace the rhythm of nature: January mornings breaking ice on water troughs, February afternoons tapping maples for syrup, and March evenings tending seedlings in the greenhouse, dreaming of summer tomatoes. The possibilities are manifold; life on East Hill Farm is generous and abundant. History You Can Touch--Walk these 227 acres and feel it: the weight of continuity. Five families in 227 years. Thomas Shepard, who helped found New Marlborough. The Hartwells, who held it for a century. Arabian horse breeders who landed their plane in the pasture. The current family, who pieced the scattered acres back together, whose daughters gathered eggs, boiled sap into syrup, grew the gardens that still bloom today. Some things do endure. That which matters can be preserved. In a disposable world, permanence is possible. The next chapter begins with you. The Berkshire Life, Perfected--Twenty minutes to Great Barrington's restaurants and shops. Less than ten to the Southfield Store. Tanglewood for summer concerts, Jacob's Pillow for dance, Butternut for winter skiing. Bradley Airport an hour away, Manhattan and Boston each two and a half hours. But honestly? Once you're here, leaving becomes the hard part. Mornings at East Hill Farm start with the mourning doves' lullaby that sounds like memory itself. The Sandhill Cranes return each spring to the lower pastures, their distinctive call announcing another season. Summer evenings, you'll sit on the west porch watching the sunset over your pond while fireflies rise from the meadows, and emerge from the woods. Winter nights, you'll build fires in those perfect fireplaces and be grateful they built that beehive oven so large. Everything here has been cared for with a deep knowledge of history and respect for nature and tradition. The heritage roses still bloom. The stone walls still stand true. The forest trails lead to hidden waterfalls and forgotten cellar holes. The gardens produce abundance. The pastures are ready to graze horses. Or you could simply walk your 227 acres knowing that in a world of constant change, you've found something real, something lasting, something irreplaceable. At $5.8 million, East Hill Farm offers what money rarely can buy: authenticity at scale. A genuine 18th-century house that works for 21st-century life. Land enough that you own your own hilltop. Buildings that tell the story of America. Privacy without isolation. History without the museum ropes. And beyond price, a place of profound peace that has endured through every chapter of American history, a hilltop sanctuary. Wake each morning in that otherworldly, untouchable tranquility that settles over the hilltop, where the rest of the world falls away, to watch the sun set where generations have watched it set, to be part of something larger than yourself, while making it entirely your own. 227 acres. 227 years. Some things are meant to be. Come see.

Presenting an offering of rare distinction. Refined coastal living, classic architecture and impeccable craftsmanship blend to create a unique sense of privacy, elegance, and pleasure. Nestled upon the shores of iconic Bass River, bask in waterfront living in this exclusive legacy estate replete with a deep water dock, private beach, and spectacular pool and spa. Beyond the auto gates, this private enclave encompasses a main house, carriage house, guest house and boathouse. The estate is set among lush plantings, exquisite gardens, curated vistas, and secluded courtyards. The sun-drenched interiors boast a peaceful balance of function and modern refinement. Custom appointments, outstanding finishes and bespoke details provide exceptional continuity. A deep-water dock and elaborately designed pier, capable of welcoming a substantial yacht with additional space for two vessels, offers direct access to Nantucket Sound and the Atlantic. This highlights the estate's stature as an ultimate residence for those seeking leisure and adventure. The setting, extraordinary amenities and elegance celebrate the unparalleled rhythm of a timeless, Cape Cod lifestyle.

Defined by panoramic views of the Atlantic Ocean, White Goose Cove, and a backdrop of protected conservation land, 8 Sheep Pond is an extraordinary coastal compound set on more than two acres. Featuring a five-bedroom main house, three-bedroom guest house, pool house studio, and an 18' x 36' swimming pool, the property is positioned to capture sweeping southwest-facing ocean views and unforgettable sunsets. Offered fully furnished, the compound underwent a comprehensive renovation in 2021 and was beautifully reimagined with warm earth tones, natural textures, and timeless materials, creating an atmosphere that is both refined and welcoming. Walls of windows frame the surrounding scenery from nearly every room, creating a seamless connection between indoor and outdoor living while showcasing the ever-changing beauty of the ocean, cove, and conservation land beyond. Whether entertaining on the decks, gathering around the pool, enjoying lawn games across the sprawling lawn, or simply taking in the water views, every aspect of the property has been designed to embrace its remarkable surroundings. Complementing its exceptional lifestyle appeal is a proven and substantial rental history, with seasonal rental income exceeding $400,000 in peak years. An opportunity to own one of Nantucket's most compelling coastal compounds, where natural beauty, timeless design, and an extraordinary connection to the surrounding landscape are seamlessly woven together in one unforgettable setting.

A rare offering on the shores of Menemsha Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Thoughtfully designed with striking modern architecture, walls of glass, and seamless indoor-outdoor living, this one-of-a-kind compound captures breathtaking water views from nearly every room. Set on 4.9 acres with a private 115-foot deep-water dock, the property represents an irreplaceable opportunity, as a waterfront estate of this scale and caliber could no longer be replicated today. The main residence features six luxurious ensuite bedrooms, including a spectacular first-floor primary suite with dual spa-inspired bathrooms. Two state-of-the-art kitchens appointed with top-tier appliances provide exceptional spaces for entertaining, while the dramatic main living area showcases soaring cathedral ceilings and panoramic pond views. A screened porch and expansive waterfront deck create effortless transitions between interior and exterior living spaces. Upstairs, a striking glass-lined hallway with a dramatic glass floor overlooks the water, leading to guest suites with private baths and access to a second-floor deck. Exceptional amenities include a private theater with massage seating, wine cellar, outdoor shower, and a hilltop writer’s cottage with sweeping waterviews. Set just beyond the main house is the pool house. The pool house is a private wellness retreat featuring a heated indoor pool, spa, sauna, cold plunge, steam room, wet bar, and spacious enclosed porch surrounded by retractable glass doors. The second floor includes a full guest suite with a bedroom, living room, laundry, and dual balconies overlooking Menemsha pond. The estate also includes an impressive 1,927 sq. ft. barn-style entertainment pavilion designed to complement the property’s contemporary aesthetic while offering exceptional recreational amenities. The upper level features a professionally designed fitness center with floor-to-ceiling windows overlooking the grounds and pond, alongside a sprawling recreation lounge with space for indoor basketball, billiards, ping pong, and additional sporting activities. Below, the structure houses an expansive six-car garage, ideal for luxury vehicle storage, boating equipment, and recreational gear. Completing this incomparable estate are a private tennis court and charming boathouse by the dock for paddleboards and waterfront equipment. An unparalleled modern retreat in one of Martha’s Vineyard’s most exclusive waterfront settings.

Situated in a pedigree location just off the Town Common and Historic District, this remarkable colonial home with Craftsman influence and a stunning addition/remodel is unique in its beauty and design. The sale comes with an adjacent 1ac house lot w/sewer and water. FHW heat in main; FHA hybrid (electric heat pump, backed up by oil). Separate cen air handler in attic of main house; fha furnace for addition. Extensive renovation including roof, heating systems, interior paint, multi-coat paint on kitchen cabinets. Hardwood flooring throughout most of the home. Family room w/soaring 2-story ceiling and stone fireplace. 1st floor en suite primary BR w/large bath that has separate vanities, steam shower, large jetted tub (heater not working). Formal dining w/fireplace. First floor liv rm/office w/cathedral ceiling and half bath. Appx 1,000 SF finished in LL and includes laundry and ironing room. Dumb waiter goes to all 3 floors. Gentleman's barn. Inground pool.

“Wait and See” is a stunning coastal retreat commanding extraordinary, unobstructed views of the Atlantic Ocean and Tom Nevers Pond. Perched on an elevated and beautifully landscaped acre, the property captures sweeping vistas and exceptional privacy. The first floor features two guest bedrooms with a shared bath, along with a serene primary suite complete with an en suite bath and direct access to a wraparound deck overlooking the landscape. The lower level offers a spacious family room, dedicated office, and walkout access to a private patio—ideal for relaxed indoor-outdoor living. The second floor is designed for gathering and entertaining, with an open-concept living room and a well-appointed gourmet kitchen. Expansive wraparound decks on this level provide seamless outdoor living spaces, perfectly positioned to take in the panoramic views and coastal breezes. A charming breezeway connects the three-bedroom main house to a two-bay garage, above which a private fourth bedroom suite with full bath enjoys its own elevated vantage point and beautiful views. The grounds are equally impressive, featuring a thoughtfully designed garden with a sunken patio and fire pit seating area. The outdoor experience is anchored by a stunning 18’ x 36’ pool, an 8’ x 8’ spa, and a generously sized outdoor shower, all complemented by multiple seating and lounging areas—creating an exceptional setting for summer living and entertaining. Additional amenities include access to two association tennis courts, located just one mile from the property.

Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation home for a client list that included Lady Diana Spencer. The historic main house has been completely modernized. There are 6 bedrooms spread out over almost 6000 square feet, a detached pool house, swimming pool, and Har-Tru tennis court. Wherever you are in this gracious home you will be blessed with sweeping views of the open fields, stone walls, and horses in the neighboring farm, a scene as if from a painting done in a previous century. Included within the 10 acres is a separate 3.3-acre parcel of land that will accommodate a full-size home. The property is part of the Tashmoo Farm Association which includes deeded access to the association dock on Lake Tashmoo and tennis courts.

Welcome to an extraordinary waterfront retreat, where luxury meets nature perfectly. This exclusive property offers unparalleled access to breathtaking views, serene landscapes, and the soothing sounds of water lapping against the shore. Squibnocket Farm Road is renowned for its unspoiled beauty and tranquility. This sophisticated gated community offers a sense of seclusion while remaining within a reasonable distance from essential amenities and entertainment options. Whether you're looking for a year-round residence or a vacation getaway, this waterfront home in Squibnocket is an idyllic sanctuary to create unforgettable memories with family and friends.

Commanding a presence high on the Sconset Bluff, this private family compound is inarguably one of the most stunning properties on Nantucket. Sited so as to enjoy sweeping, unobstructed views of the Atlantic Ocean, Sesachacha Pond, and Sankaty Light, the 6-acre estate includes a 12,000 square foot main residence, a 2 bedroom guest house, and a water feature. This water feature is unmatched with a fire pit and seating area, surrounded by a wrap around pool. While using these outdoor amenities, enjoy spectacular sunsets and sunrises over the Atlantic Ocean. Originally constructed in 2006 and extensively and thoughtfully renovated in 2024, this legacy property has extraordinary architectural details and exquisite museum-quality finishes. Drawing inspiration from the island’s serene natural color palette, the interior is washed in soothing sandy beiges, coastal grays, and nautical blues, seamlessly blending with the breathtaking seascape to create a tranquil and calming respite. 37 Sankaty Head Road marks an opportunity for a new owner to create their own tradition of exceptional living. Quiet elegance is the hallmark of this residence. Generously-sized, light-filled rooms feature intricate box trim and coved ceilings, solid panel doors, and exquisitely crafted bespoke details that add dimension and depth. Every element—from the light fixtures to the carefully chosen pops of color—has been selected with reflection and intention.

Rare Oceanfront Queen Anne Victorian Estate | Beachhurst | Boston Skyline Views directly on the ocean just 11 miles from Boston, this magnificent shingle-style home offers an unparalleled oceanfront lifestyle. Featuring 6 bedrooms (4 ensuite), & multiple outdoor spaces, the home is designed for grand entertaining and relaxed coastal living. Wake to sweeping views of Boston's glittering skyline, harbor islands, and open sea from nearly every room. Direct access to Eisen Beach puts sand and surf at your doorstep. The chef's kitchen opens via French doors straight to the water, while the wraparound covered porch and pergola invite endless hours of coastal enjoyment. The original craftsmanship designed by Richard Morris Hunt shines with inlaid hardwood floors, hand-carved balusters, stained-glass entry doors, rich wood paneling & multiple ornate fireplaces. Swampscott's most iconic oceanfront home with green lawn, all just minutes from the commuter rail with direct service to Boston.

75-Acre Elite Equestrian & Wellness Sanctuary. Ultimate private retreat with a 4,040 SF luxury Cape, world-class horse facilities, and resort backyard. Trail access to West Hill Dam. RESIDENCE: Chef's kitchen (Jade 6-burner, Sub-Zero, granite waterfall island). 1st-floor primary suite with vaulted ceilings & spa bath. three upper bedrooms, office, large bonus room + finished walkout lower level. two-car garage with EV charger and generator backup. EQUESTRIAN: Professional nine-stall barn, heated tack room, wash stall & blanket laundry. 12,384 SF indoor arena (172'x72') + 130'x80' outdoor arena. 60' round pen & 15 turnout paddocks. Roof solar array on barn supplies powers to the property. WELLNESS & RESORT: Detached climate-controlled gym & solar yoga "She Shed." Heated, saltwater, gunite pool, hot tub, six-person barrel sauna. Outdoor kitchen with pizza oven. Meditation labyrinth, organic fruit orchards, and berry patches.

A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest of its kind on Martha’s Vineyard. Originally built in 1835 and masterfully renovated by renowned architect Patrick Ahearn, the estate seamlessly blends historic character with refined modern luxury. Just moments from Edgartown Harbor and the island’s premier dining and shopping, the property spans two lots and offers an extraordinary compound featuring 10 bedrooms and 14 baths. Designed for both elegant entertaining and comfortable everyday living, the main residence showcases refined architectural details and modern technology. Beautiful oak floors run throughout the home, complemented by sophisticated hardware, premium appliances, and walls tastefully finished with nickel board. A gracious living room with fireplace opens to a patio with retractable screens, creating effortless indoor-outdoor flow. The chef’s kitchen is impeccably appointed with dual dishwashers, a plumbed miele coffee bar, refrigerator drawers, and a wine refrigerator. A custom brass and glass bar is equipped with an ice maker and refrigerated drawers and can easily be converted into a secondary kitchen. Two private bedrooms with en-suite tile baths anchor opposite wings of the main level, providing both privacy and balance. The main floor also includes an inviting secondary living room with a gas fireplace, an elegant dining room wrapped in seagrass wallpaper, a generous walk-in pantry, and a spacious mudroom thoughtfully designed for effortless island living. Upstairs a spectacular primary suite serves as a retreat, complete with private balcony and a bonus two full spa-inspired baths. Three additional en-suite guest rooms and a spacious laundry room complete the second floor. The third level features a charming nautical-themed bunk room with four built-in beds and full bath. The finished lower level includes two bedrooms with en-suite baths, a media room, wine cellar, and additional laundry. Beyond the main house is a beautifully finished two-car garage with brick floors and wood-paneled walls. The carriage house above the garage offers a private guest suite with a balcony overlooking the pool. The outdoor setting is unparalleled for in-town living. Lush hydrangeas surround a resort-style pool and spa, complemented by a built-in grill, firepit, and an exceptional cabana with kitchenette, half bath, laundry, heating and air conditioning. This Edgartown estate offers privacy, scale, and sophistication rarely found within steps of Main Street. An iconic Martha’s Vineyard property reimagined for modern coastal living.