luxury houses with pool for sale Massachusetts, United States (page 3)

A one-of-a-kind European-inspired estate on 5.6 private wooded acres, featuring a private elevator, a 15-car garage compound, an indoor pool pavilion ready for completion, an immense customizable lower level, and exceptional craftsmanship. Some homes are built to satisfy the market. Others are created to fulfill a vision. La Farigoule belongs unmistakably to the latter. Inspired by the timeless country estates of France and Southern Europe, this extraordinary custom residence was conceived not as a speculative development, but as a lifelong private estate where architecture, craftsmanship, and imagination took precedence over convention. Every room, proportion, and crafted detail reflects a singular vision, giving the home remarkable character and unmistakable personality. Set amid secluded woodlands, La Farigoule reveals itself through remarkable spaces and unexpected discoveries. A private elevator serves every level, from the expansive lower level to the attic, combining elegance with convenience. The spectacular 15-car garage compound offers an extraordinary setting for automobile collectors, while a rare underground passage discreetly connects it to the residence—an architectural feature almost never found in a private home. A magnificent indoor swimming pool pavilion awaits completion as a year-round wellness retreat. Beneath the residence, an immense lower level can become a private cinema, wine cellar, fitness center, spa, golf simulator, guest residence, or exceptional entertainment venue. These spaces invite the next owner to shape the estate around a personal lifestyle. Even the smallest details express the home's European spirit. A traditional wood-fired pizza oven evokes Tuscany and Provence, where family and friends gather around simple pleasures, fine food, and memorable evenings. Handcrafted millwork, custom stonework, soaring spaces, and bespoke details create warmth, authenticity, and timeless elegance rarely found in contemporary construction. La Farigoule is more than a luxury residence—it is a home with a soul. Created not simply to impress, but to endure, it is complete in its architectural vision while offering opportunities for personalization without compromising its identity. Only minutes from Boston, yet surrounded by privacy, La Farigoule is for those who seek originality over convention, craftsmanship over fashion, and character over excess. Some houses are admired. Some houses are envied. La Farigoule is remembered.

Experience the perfect balance of grand-scale architecture and tranquil nature in this stunning 6,000+ sq. ft. modern Colonial. Nestled on 3.42 manageable acres within a private enclave near Onota Lake, this 5-bedroom, 5.5-bath estate offers sweeping meadow views just minutes from the world-class arts of Tanglewood and The Clark. The entry is marked by dramatic dry-laid stonework, leading into an interior defined by soaring heights. The heart of the home is a two-story living room featuring vaulted ceilings and a floor-to-ceiling stone fireplace. The expansive living space of the great room flows effortlessly into a gourmet chef's kitchen equipped for high-end entertaining with dual refrigerators, double wall ovens, and a center island cooktop with a built-in griddle. High-top island seating allows for social cooking and a sizable breakfast area flanked by a wall-to-wall credenza—ideal for buffet-style hosting. The home's floor plan thoughtfully blends communal areas with distinct privacy across three levels. The main level is designed for complete convenience and the primary suite is a true sanctuary. It features a private egress to the pool and a hidden back staircase leading to a secluded loft—perfect for a library or reading nook overlooking the suite. The upper level offers a sweeping gallery balcony overlooking the great room, leading to four spacious bedrooms. This includes two private ensuites and two additional bedrooms serviced by a full bath and a dedicated laundry room. The lower level is an entertainment hub featuring a home theater, gaming space, gym, full bath, and a secondary egress for easy garage access. The fully-fenced backyard makes for a resort-style oasis. Host movie nights on the expansive deck, or relax by the heated inground pool and custom-finished patio. The designer firepit is anchored by a unique stone compass inlay, and a poolside full bathroom ensures guests never need to track water through the main house. For the automotive hobbyist or enthusiast, a high-end, three-bay attached garage is professionally finished with epoxy floors, industrial-style metal cabinets, and an EV charger. You will also find a massive, 50x40 detached shop with four bays and oversized doors. Whether for housing a car collection, an RV, or a professional art studio, the possibilities of this space are endless. Embrace the Berkshire landscape in a home where every detail has been considered. Whether you are heading out for fine dining or staying in to enjoy your private oasis, Blythewood Estates offers a lifestyle of unparalleled peace and sophistication.

Set on a peaceful 1.13-acre parcel just steps from the Acoaxet Club and a short walk or bike ride to the beach, this exceptional Westport Harbor property offers a rare blend of privacy, comfort, and coastal charm. Designed for effortless indoor-outdoor living, the grounds feature bluestone patios with western exposure, majestic trees, mature landscaping, and a saltwater pool. The stunning 2,257 sqft. addition showcases vaulted ceilings, an open-concept living and dining area with fireplace, a chef’s kitchen with Vermont soapstone and custom wood counters, library, large screened porch, and a sumptuous primary suite with steam shower, soaking tub, and steps out to an outdoor shower. The rebuilt 1,681 sqft. four-bedroom, two-bath wing with fireplaced living room and a second outdoor shower provides abundant space for family and friends. Convenient to Adamsville, Tiverton Four Corners, and Little Compton. A true stunner in an ideal location!

OLD GARDEN BEACH + POOL + PRIVACY + PARKING + WALKABILITY + ROCKPORT. Capture precious warm weather time in your new Rockport home as you make plans for next summer. A short stroll to Old Garden Beach. Swim in your own pool. Head downtown for dinner. Come home to your private cul-de-sac retreat. Welcome your whole family - parking for seven cars is an exceptional Old Garden Beach advantage! You don’t have to maintain a waterfront property to enjoy the perfect Rockport summer lifestyle. Add up the recent improvements - Gunite pool resurfaced in 2022, 2026 new roof and skylights, whole house exterior paint just months ago, updated side and front entry doors, new garage doors, and balcony with stairs from primary bedroom to backyard just replaced, and recent condenser for the central air system.

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.

Looking for room to spread out? This spacious home in desirable North Tewksbury offers over 2,400 square feet of living space on two levels and features a private in-ground liner pool, making it ideal for both everyday living and entertaining. The main level showcases hardwood flooring throughout the living room, dining area, sunroom, and bedrooms. The dining area opens to a spacious kitchen with ample counter space and stainless steel appliances, as well as a four-season sunroom with a vaulted ceiling, skylights, and a ceiling fan. The sunroom provides access to a composite deck overlooking the fenced in-ground pool area, perfect for relaxing or hosting summer gatherings, as well as nice size yard. The finished lower level is anchored by a generous front-to-back family room with a wood burning fireplace and new carpet providing the perfect space for movie nights, game days, or a playroom. This level also includes an additional bedroom, a versatile bonus room ideal for a home office or gym, and a convenient half bath with laundry. A two-car attached garage offers plenty of room for vehicles and extra storage. Additional features include two pull down steps to attic in hall and garage, a storage shed, gas heat, a gas range, central air conditioning on the main level with a new compressor, a Generac whole-house gas generator, Star Link security system and town water and sewer. With it's fabulous location, generous living space, flexible floor plan, and exceptional indoor and outdoor amenities, this home is ready to welcome its next owners.

Extraordinary estate on 1.64 manicured acres overlooking the Newbury Upper Green. This meticulously renovated Colonial, incorporating a restored barn, blends historic character with thoughtfully designed living spaces. Features include hand-hewn beams, wide pine floors, 21-foot ceilings, six brick fireplaces, custom millwork, dramatic living room, library, bar, multiple gathering spaces, indoor pool with ozone purification, detached accessory building with full kitchen, bar and bath, multi-zoned HVAC, irrigation wells, central vacuum, whole-house sound, internet infrastructure and generator servicing critical systems.

Imagine making your memories in a home that's as welcoming as it is beautifully maintained. Nestled in one of Newburyport's most sought-after neighborhoods, this custom Colonial offers the perfect blend of timeless charm, modern updates, and exceptional indoor/outdoor living. Thoughtfully cared for and meticulously updated, this move-in-ready home features a new roof, two energy-efficient mini-splits, in addition to the central air, a cozy gas fireplace, three wood-burning fireplaces, a Generac whole-house generator, whole-house water filtration, and an additional 9 inches of insulation, providing year-round comfort and peace of mind. Inside, generously sized rooms give everyone space to gather, relax, and grow. The stunning family room addition, surrounded by walls of glass, fills the home with natural light and offers beautiful views of the backyard oasis. Step outside to an oversized deck and patio overlooking the sparkling in-ground pool, vibrant flower gardens, cabana, and outdoor shower, creating the perfect setting for summer barbecues, pool parties, or quiet evenings under the stars. When you're ready to explore, you'll love being just minutes from parks, shopping, restaurants, commuter routes, and the charming Newburyport waterfront. Whether it's bike rides to the park, weekends by the water, or hosting family and friends at home, this is a place where everyday living feels extraordinary. This isn't just a house; it's the backdrop for your next chapter.

Welcome to Serenity Hill. This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires. Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind. The vaulted ceiling in the kitchen adds a sense of light and openness, while seamless transitions between the kitchen, dining area, and living room create a space that feels both cohesive and welcoming. A cozy wood-burning fireplace anchors the living room, adding warmth and charm to the heart of the home. With 3 bedrooms and 2.5 baths, every space feels intentional, comfortable yet refined rendering this home ideal for both everyday living and effortless entertaining. Thoughtful design choices enhance the home's warmth and inviting atmosphere. From the living room, multiple doors open onto a private back deck, creating a natural extension of the home's inviting flow. Beyond the deck, you'll find your own private sanctuary: a peaceful koi pond, an inviting in-ground pool, and a hot tub perfect for unwinding under the stars. Whether you're savoring quiet mornings in nature or hosting lively summer gatherings, this property offers the perfect balance of serenity and connection. This is more than just a home, it's a true Berkshire retreat, where timeless style shines in one of the area's most desirable settings.

Offered fully furnished and ready to enjoy, this Majestic Tudor Berkshire Estate sits on 71 Acres atop Tom Ball Mountain in quaint Alford, MA. Privacy and Breathtaking views. Formal Entry and Foyer. Stately Living Room and Dining Room. Great Room with Gourmet Kitchen. Den, Family Room, Gym and Massage Room. 5 en-suite Bedrooms in the Main House. 2 Bedroom Tudor Guest House w beamed ceilings and full amenities. Manicured grounds, infinity Pool and Hot Tub, Pool House with full Bath, Tennis Court and Pickleball Court. 7 Garages and additional Barn. Exquisite architectural touches, state-of-the-art home technology and security, in the most peaceful of surroundings. Easy access by road, rail and private Airport. Close to Tanglewood and Berkshire attractions.

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.

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.

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.

Introducing a timeless European inspired mansion with a private gate and elegant marble fountain. This custom estate is situated on three acres. A spectacular pool and spa complemented by a fully equipped pool house with a kitchen adorn the grounds. A beautiful wrought iron fence embraces the entire estate which includes stone patios and tennis court. The grand entry and living and dining rooms boast beautiful granite floors for fine entertaining. Additionally, rich oak wood floors are throughout the house. Three custom marble fireplaces grace the sitting areas. A first floor primary suite, private office and sunroom complete the main level. Upstairs has four large bedroom suites while the finished third floor is ideal for a dual in-home office or guest bedroom. The tremendous lower level features a sauna, steam and home theater. This exceptional home embodies an elevated blend of refined and recreational living. This location provides excellent proximity to Boston and top-ranked schools.

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.

Located in the highly sought-after Nora’s Meadow community in Edgartown, this exceptional coastal property offers the rare combination of privacy, acreage, and close proximity to downtown Edgartown, South Beach, and the Katama bike path. Set on 1.8 beautifully landscaped acres, this custom home was built in 2014 and features over 4,000 square feet of thoughtfully designed living space across three levels. A welcoming mudroom, ideal for beach living, opens into a bright and expansive main living area featuring a spacious dining room, gourmet kitchen, and comfortable living room with oversized French doors leading to the pool patio. The first floor primary suite offers a luxurious spa-inspired bath and private French doors opening to a serene outdoor sitting area surrounded by lush landscaping. Four additional guest bedrooms are all generously sized, providing ample accommodations for family and friends. The finished lower level includes a media room, pool table area, and abundant storage space. Designed for effortless indoor-outdoor living, the backyard is a true Vineyard retreat featuring an oversized pool, outdoor kitchen, expansive stone patio, and a pool cabana complete with a full bath. A two-car garage includes unfinished space above with the unique potential to create a guest house, an exclusive feature permitted only for this property within the Nora’s Meadow association. A charming barn-style shed provides additional storage for kayaks, bikes, and boating equipment. This rare offering combines luxury, privacy, and exceptional outdoor living in one of Edgartown’s most desirable neighborhoods, creating the ultimate Martha’s Vineyard retreat for generations to enjoy.

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.

Located in Kingston’s desirable Ah-De-Nah neighborhood, this 5-bedroom, 4 full/2 half bath Colonial offers a blend of comfort, function, and coastal accessibility just moments from Jones River Landing, Kingston Bay, and Bay Farm Conservation trails. The home features three ensuite bedrooms, including a private primary suite with gas fireplace, custom walk-in dressing room, and spa-like bath. Hardwood floors, generous living spaces, and custom millwork are found throughout. The kitchen is well-appointed with a walnut-topped center island, glass-front hutch, integrated desk, six-burner gas range, double ovens, and wine bar, and opens to a fireplaced family room with French doors leading to a screened porch. Outdoor features include a heated saltwater in-ground pool and hot tub, professionally landscaped grounds with perennial gardens, hydrangeas, and stone walls, as well as a private pickleball court. Additional highlights include a finished lower level with home theater and a 3-car garage.

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.

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.

Privately set on over an acre in one of Manchester-by-the-Sea’s most sought-after coastal neighborhoods, 3 Proctor offers convenience located just 0.4 miles from Singing Beach and moments from the Village’s shops and dining. Thoughtfully designed for both grand entertaining and everyday comfort, the home showcases expansive living areas, soaring vaulted ceilings, and dramatic floor-to-ceiling windows that bathe the interiors in natural light. Multiple fireplaces add warmth and character throughout. Recent improvements include beautifully refinished hardwood floors, fresh interior paint, and enhanced landscaping, ensuring a move-in-ready experience. The flexible floor plan features five bedrooms, highlighted by a generous primary suite and a private guest suite above the garage with its own entrance—ideal for extended stays or visiting guests. Coastal living, Reimagined.

Rare 70+ Acre Private Equestrian Estate & Retreat OR DEVELOPMENT OPPORTUNITIES set 1/4 mile off the road. Escape to an extraordinary sanctuary offering 70+ acres of pristine land, exceptional equestrian facilities, and refined luxury living. Centered around a private 4-acre pond, this magnificent estate delivers an unmatched blend of secluded outdoor freedom and high-end comfort. The Residence-Spacious Living: Spectacular 4,200+ sq. ft. light-filled home featuring 3 expansive bedrooms and 2.5 baths.Resort-Style Amenities: Gunite In-ground pool overlooking sweeping grounds, ideal for outdoor entertaining or quiet relaxation.Equestrian & Land FeaturesTurnkey Facilities: Fully equipped horse barn with direct access to fenced paddocks.On-Site Trails: Private riding and walking trails woven throughout the estate's 70+ acres. Ideal for fishing, kayaking, or enjoying scenic reflection views from the main residence.Whether you're an equestrian enthusiast, looking for a private family compound, or seeking an exclusive retreat, this turn-key property offers infinite possibilities. Developer & Investment Potential in addition to its appeal as a private paradise, this estate offers exceptional potential for developers. Engineered plans are already in hand for a 19-lot subdivision, with potential for additional buildable lots. Keep the existing residence and barn on a sprawling private parcel while developing the remaining land, or capitalize on the full development capabilities of this extraordinary holding.