Southshorehomefinder.com Search Results

$16,500,000

A rare and extraordinary offering, this iconic beachfront estate stands as one of the finest properties on all of Cape Cod. Located in the heart of Hyannis Port, the stately colonial residence is perfectly set on magnificent grounds designed by the Olmsted Brothers, with mature trees, manicured hedges, and rolling lawns that give way to 410' of pristine sandy beach. From every vantage point across the property, mesmerizing views of Nantucket Sound, Hyannis Port Harbor, and Great Island provide a backdrop of unsurpassed natural beauty. Immediately upon entering the residence, unobstructed vistas take center stage and continue throughout each room. Grand gathering spaces seamlessly connect to the outdoor living areas, with thoughtful proportions and scale for every occasion. The light-filled kitchen includes an informal breakfast area and direct access to the pool and waterside terrace. In the study and wet bar, rich millwork and exquisite craftsmanship lend a sense of warmth that carries into the formal dining room. A luxurious primary suite and six well-appointed guest bedrooms provide refined accommodations for all. This inimitable legacy estate is steps from the West Beach Club and Hyannis Port Yacht Club, with Cape Cod's best golf courses, deep-water marinas, Cape Cod Gateway Airport, and ferry service to Martha's Vineyard and Nantucket just minutes away. A once-in-a-lifetime opportunity, one of the most iconic estates on the Eastern Seaboard awaits its next chapter.

7 Beds ⋅ 8 Baths ⋅ 22505725 MLS

A rare and extraordinary offering, this iconic beachfront estate stands as one of the finest properties on all of Cape Cod. Located in the heart of Hyannis Port, the stately colonial residence is perfectly set on magnificent grounds designed by the Olmsted Brothers, with mature trees, manicured hedges, and rolling lawns that give way to 410' of pristine sandy beach. From every vantage point across the property, mesmerizing views of Nantucket Sound, Hyannis Port Harbor, and Great Island provide a backdrop of unsurpassed natural beauty. Immediately upon entering the residence, unobstructed vistas take center stage and continue throughout each room. Grand gathering spaces seamlessly connect to the outdoor living areas, with thoughtful proportions and scale for every occasion. The light-filled kitchen includes an informal breakfast area and direct access to the pool and waterside terrace. In the study and wet bar, rich millwork and exquisite craftsmanship lend a sense of warmth that carries into the formal dining room. A luxurious primary suite and six well-appointed guest bedrooms provide refined accommodations for all. This inimitable legacy estate is steps from the West Beach Club and Hyannis Port Yacht Club, with Cape Cod's best golf courses, deep-water marinas, Cape Cod Gateway Airport, and ferry service to Martha's Vineyard and Nantucket just minutes away. A once-in-a-lifetime opportunity, one of the most iconic estates on the Eastern Seaboard awaits its next chapter.

155 Irving Avenue, Hyannis Port

Listing courtesy of Listing Agent: Paul E Grover (paul@paulgrover.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

$16,500,000

A rare and extraordinary offering, this iconic beachfront estate stands as one of the finest properties on all of Cape Cod. Located in the heart of Hyannis Port, the stately colonial residence is perfectly set on magnificent grounds designed by the Olmsted Brothers, with mature trees, manicured hedges, and rolling lawns that give way to 410' of pristine sandy beach. From every vantage point across the property, mesmerizing views of Nantucket Sound, Hyannis Port Harbor, and Great Island provide a backdrop of unsurpassed natural beauty. Immediately upon entering the residence, unobstructed vistas take center stage and continue throughout each room. Grand gathering spaces seamlessly connect to the outdoor living areas, with thoughtful proportions and scale for every occasion. The light-filled kitchen includes an informal breakfast area and direct access to the pool and waterside terrace. In the study and wet bar, rich millwork and exquisite craftsmanship lend a sense of warmth that carries into the formal dining room. A luxurious primary suite and six well-appointed guest bedrooms provide refined accommodations for all.This inimitable legacy estate is steps from the West Beach Club and Hyannis Port Yacht Club, with Cape Cod's best golf courses, deep-water marinas, Cape Cod Gateway Airport, and ferry service to Martha's Vineyard and Nantucket just minutes away. A once-in-a-lifetime opportunity, one of the most iconic estates on the Eastern Seaboard awaits its next chapter.

7 Beds ⋅ 8 Baths ⋅ 73457530 MLS

A rare and extraordinary offering, this iconic beachfront estate stands as one of the finest properties on all of Cape Cod. Located in the heart of Hyannis Port, the stately colonial residence is perfectly set on magnificent grounds designed by the Olmsted Brothers, with mature trees, manicured hedges, and rolling lawns that give way to 410' of pristine sandy beach. From every vantage point across the property, mesmerizing views of Nantucket Sound, Hyannis Port Harbor, and Great Island provide a backdrop of unsurpassed natural beauty. Immediately upon entering the residence, unobstructed vistas take center stage and continue throughout each room. Grand gathering spaces seamlessly connect to the outdoor living areas, with thoughtful proportions and scale for every occasion. The light-filled kitchen includes an informal breakfast area and direct access to the pool and waterside terrace. In the study and wet bar, rich millwork and exquisite craftsmanship lend a sense of warmth that carries into the formal dining room. A luxurious primary suite and six well-appointed guest bedrooms provide refined accommodations for all.This inimitable legacy estate is steps from the West Beach Club and Hyannis Port Yacht Club, with Cape Cod's best golf courses, deep-water marinas, Cape Cod Gateway Airport, and ferry service to Martha's Vineyard and Nantucket just minutes away. A once-in-a-lifetime opportunity, one of the most iconic estates on the Eastern Seaboard awaits its next chapter.

155 Irving Avenue, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$16,250,000

Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets. The home centers on a soaring great room with 17-foot vaulted ceiling, fieldstone fireplace, oak post-and-beam detailing, chef's kitchen, and walls of glass opening to the landscape. Five bedrooms are complemented by two offices, a gym, bunk room, and walkout recreation room. Across the lawn, a finished barn offers flexible guest and entertaining space, a loft with full bath, and three-car garage. Open meadows, exceptional privacy, and private paths lead to Great Rock Bight, while the five-member association offers an additional 100 feet of private beach with a bluff-top camp and fire pit. Chilmark's Lucy Vincent and Squibnocket beaches and Menemsha village complete this rare up-island offering.

6 Beds ⋅ 8 Baths ⋅ 22603861 MLS

Perched on an elevated 10.69-acre site off picturesque North Road in Chilmark, this exceptional private compound pairs natural beauty with architectural distinction. Designed by renowned architect Patrick Ahearn and built by Rosbeck Builders, the 7,691-square-foot residence enjoys dramatic views across the Menemsha Hills and Vineyard Sound toward the Elizabeth Islands, with spectacular sunsets. The home centers on a soaring great room with 17-foot vaulted ceiling, fieldstone fireplace, oak post-and-beam detailing, chef's kitchen, and walls of glass opening to the landscape. Five bedrooms are complemented by two offices, a gym, bunk room, and walkout recreation room. Across the lawn, a finished barn offers flexible guest and entertaining space, a loft with full bath, and three-car garage. Open meadows, exceptional privacy, and private paths lead to Great Rock Bight, while the five-member association offers an additional 100 feet of private beach with a bluff-top camp and fire pit. Chilmark's Lucy Vincent and Squibnocket beaches and Menemsha village complete this rare up-island offering.

25 Brickyard Road, Chilmark

Listing courtesy of Listing Agent: Peyton Wallace (peyton@studiorealty.com) from Listing Office: Studio Realty LLC.

$16,000,000

This spectacular residence, set on 4.5 acres in the prestigious Brookline Estate area, has been renovated and is surrounded by private, scenic landscapes. The interior, distinguished by its grandeur and elegance, is adorned with intricate period details, beautiful woodwork, and bright spacious rooms. The grand 13 rooms include a double living room with picturesque views of the gorgeous, expansive grounds. There are 6 bedrooms, one of which is the luxurious primary suite. The meticulously designed grounds feature several unique amenities, including a stunning terrace patio expanding the length of the home, an in-ground swimming pool with fountain and whirlpool artfully integrated with a stone cliff, fully equipped cabana, koi pond, private tennis court, putting green, and magnificent hardscaping. The property also has a three-bedroom cottage and a two-bedroom unit above the free-standing garage. Near fine shops, restaurants, and Downtown Boston.

6 Beds ⋅ 8 Baths ⋅ 73480812 MLS

This spectacular residence, set on 4.5 acres in the prestigious Brookline Estate area, has been renovated and is surrounded by private, scenic landscapes. The interior, distinguished by its grandeur and elegance, is adorned with intricate period details, beautiful woodwork, and bright spacious rooms. The grand 13 rooms include a double living room with picturesque views of the gorgeous, expansive grounds. There are 6 bedrooms, one of which is the luxurious primary suite. The meticulously designed grounds feature several unique amenities, including a stunning terrace patio expanding the length of the home, an in-ground swimming pool with fountain and whirlpool artfully integrated with a stone cliff, fully equipped cabana, koi pond, private tennis court, putting green, and magnificent hardscaping. The property also has a three-bedroom cottage and a two-bedroom unit above the free-standing garage. Near fine shops, restaurants, and Downtown Boston.

63 Goddard Avenue, Brookline

Listing courtesy of Listing Agent: Debby Belt from Listing Office: Hammond Residential Real Estate.

$15,900,000

Introducing one of New York's most prestigious estates: a rare opportunity to own a historic piece of history elegantly nestled atop 11+ park-like acres in Purchase. This illustrious and stately turn-of-the-century residence, was the setting for the blockbuster film "Goodbye Columbus." A quiet country manor that's exceptionally private and secure, the estate is a stunning work of art, beautifully situated behind a gated entry at the end of a long, meandering driveway. The property boasts acres of lush rolling lawns adorned with over 35 years of seasonal perennials in year-round bloom, a glorious fenced saltwater pool and patio, multiple-hole practice golf green, zen-like meditation garden, and a one-acre freshwater pond with koi and carp. Encircling the property is a half mile jogging path with a grove of weeping willows, a spectacular oasis of hydrangeas, indigenous stone walls, a shady gazebo, and a charming life-size dollhouse. Inside, the home is breathtaking, with 11,792 sq ft of custom-crafted beauty featuring 7 bedrooms, 6.4 bathrooms, and 3 offices spread over three sunlit floors.

7 Beds ⋅ 10 Baths ⋅ 24107072 MLS

Introducing one of New York's most prestigious estates: a rare opportunity to own a historic piece of history elegantly nestled atop 11+ park-like acres in Purchase. This illustrious and stately turn-of-the-century residence, was the setting for the blockbuster film "Goodbye Columbus." A quiet country manor that's exceptionally private and secure, the estate is a stunning work of art, beautifully situated behind a gated entry at the end of a long, meandering driveway. The property boasts acres of lush rolling lawns adorned with over 35 years of seasonal perennials in year-round bloom, a glorious fenced saltwater pool and patio, multiple-hole practice golf green, zen-like meditation garden, and a one-acre freshwater pond with koi and carp. Encircling the property is a half mile jogging path with a grove of weeping willows, a spectacular oasis of hydrangeas, indigenous stone walls, a shady gazebo, and a charming life-size dollhouse. Inside, the home is breathtaking, with 11,792 sq ft of custom-crafted beauty featuring 7 bedrooms, 6.4 bathrooms, and 3 offices spread over three sunlit floors.

1619 Purchase St, Harrison

Listing courtesy of Leslie McElwreath from Sotheby's International Realty. (917) 539-3654 (203) 869-4343

$15,700,000

Modern luxury meets history in this completely renovated home on coveted Brattle St in Harvard Square. Completely transformed by a local respected builder, this property seamlessly blends historic charm w/ modern convenience in its impeccable design and finishes. The main floor offers a grand staircase, high ceilings, spacious living and dining rooms, chef's kitchen w/ top appliances and adjacent family room, an oversized mudroom off the attached garage and 2 half baths. The 2nd level has a luxurious primary suite w/ spa-like bath and gracious dressing room, 5 ensuite bedrooms (or offices) and a large laundry room. The top floor hosts a versatile office/loft space and a half bath. The lower level is fully equipped w/ a gym, game room, family room, full bath, ample storage and guest suite w/ direct exterior access. The outdoor and indoor spaces blend seamlessly for easy living, w/ a spacious patio and beautiful yard designed by a celebrated landscape architect. A true Harvard Square gem

7 Beds ⋅ 10 Baths ⋅ 73342079 MLS

Modern luxury meets history in this completely renovated home on coveted Brattle St in Harvard Square. Completely transformed by a local respected builder, this property seamlessly blends historic charm w/ modern convenience in its impeccable design and finishes. The main floor offers a grand staircase, high ceilings, spacious living and dining rooms, chef's kitchen w/ top appliances and adjacent family room, an oversized mudroom off the attached garage and 2 half baths. The 2nd level has a luxurious primary suite w/ spa-like bath and gracious dressing room, 5 ensuite bedrooms (or offices) and a large laundry room. The top floor hosts a versatile office/loft space and a half bath. The lower level is fully equipped w/ a gym, game room, family room, full bath, ample storage and guest suite w/ direct exterior access. The outdoor and indoor spaces blend seamlessly for easy living, w/ a spacious patio and beautiful yard designed by a celebrated landscape architect. A true Harvard Square gem

172 Brattle Street, Cambridge

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$15,400,000

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.

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

Listing courtesy of Listing Agent: Brian W Dougherty (brian.dougherty@corcoranadvisors.com) from Listing Office: Corcoran Property Advisors.

$15,400,000

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.

6 Beds ⋅ 9 Baths ⋅ 73538291 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

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$15,000,000

This magnificent oceanfront estate stands as one of the most significant properties in Marblehead. Located in the exclusive Peach’s Point neighborhood, this property offers stunning views of Crowninshield Island, Grace Oliver’s Beach, Marblehead Lighthouse, and the surrounding islands. “Seaside Farm” replaced the original Crowninshield estate in 1999 in a classic Georgian style, with meticulous attention to detail throughout. The home is designed to maximize ocean views while maintaining privacy. The grand 2-story foyer with a custom staircase sets the tone for the home, which features elegant living spaces ideal for both daily life and entertaining. The second floor includes an oceanfront primary suite with a fireplace, walk-in closet, modern bathroom, and a private deck with exceptional views. Three additional en suite bedrooms, a large office, and a laundry room complete the second floor. Caretakers 1 bedroom apartment over 4-car garage offering views of Grace Oliver's Beach and c

5 Beds ⋅ 9 Baths ⋅ 73536454 MLS

This magnificent oceanfront estate stands as one of the most significant properties in Marblehead. Located in the exclusive Peach’s Point neighborhood, this property offers stunning views of Crowninshield Island, Grace Oliver’s Beach, Marblehead Lighthouse, and the surrounding islands. “Seaside Farm” replaced the original Crowninshield estate in 1999 in a classic Georgian style, with meticulous attention to detail throughout. The home is designed to maximize ocean views while maintaining privacy. The grand 2-story foyer with a custom staircase sets the tone for the home, which features elegant living spaces ideal for both daily life and entertaining. The second floor includes an oceanfront primary suite with a fireplace, walk-in closet, modern bathroom, and a private deck with exceptional views. Three additional en suite bedrooms, a large office, and a laundry room complete the second floor. Caretakers 1 bedroom apartment over 4-car garage offering views of Grace Oliver's Beach and c

17 Crowninshield Road, Marblehead

Listing courtesy of Listing Agent: Traci Howe from Listing Office: Gibson Sotheby's International Realty.

$15,000,000

Introducing Windover, a grand Georgian estate, meticulously restored and reimagined for modern living. Approached through 5 acres of conservation land, and set atop a private, tree-lined drive, the property commands an immediate sense of arrival. Refined outdoor features include expansive terraces, a secluded walled garden, and a dogwood orchard. A pool house and heated saltwater pool overlook a tranquil pond, creating a resort-like setting. The interior is expansive yet remarkably intimate. A dramatic Mediterranean-style ballroom anchors the entertaining spaces, while the living and dining rooms open to terraces, framing the surrounding landscape at every turn. The luxurious primary suite offers a private retreat; a versatile third-floor suite accommodates guests or live-in staff with ease. A dedicated media room and home gym — with steam shower and sauna — round out the experience. Windover is a property of architectural distinction, enduring beauty, and total seclusion.

7 Beds ⋅ 7 Baths ⋅ 73531926 MLS

Introducing Windover, a grand Georgian estate, meticulously restored and reimagined for modern living. Approached through 5 acres of conservation land, and set atop a private, tree-lined drive, the property commands an immediate sense of arrival. Refined outdoor features include expansive terraces, a secluded walled garden, and a dogwood orchard. A pool house and heated saltwater pool overlook a tranquil pond, creating a resort-like setting. The interior is expansive yet remarkably intimate. A dramatic Mediterranean-style ballroom anchors the entertaining spaces, while the living and dining rooms open to terraces, framing the surrounding landscape at every turn. The luxurious primary suite offers a private retreat; a versatile third-floor suite accommodates guests or live-in staff with ease. A dedicated media room and home gym — with steam shower and sauna — round out the experience. Windover is a property of architectural distinction, enduring beauty, and total seclusion.

15 Farm Street, Dover

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.

$15,000,000

The Ultimate East Coast Sanctuary, Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning buyers who demand seclusion with proximity to NYC. This 38.91-acre compound is a one-of-a-kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence has been masterfully reimagined to incorporate 7 private bedroom suites, all with views over the landscaped property. The bespoke renovation was executed with uncompromising attention to detail and a true no-expense-spared philosophy, incorporating commercial-grade infrastructure, superior materials, and artisan-level craftsmanship throughout, as if cost were no consideration. Lofty ceilings and walls of glass are a perfect setting for an art collector. Separate wings radiate off the main rooms, each space private and thoughtfully composed. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. The barn pool house with full kitchen, bath and pro-grade gym, the pool, and a heated paddle court make this a perfect athlete's compound. Property includes renovated stone guest/caretaker cottage and a private office pavilion. The landscape offers open vistas, an orchard, and allowed equestrian use. Live in ultimate style and privacy surrounded by a 155-acre nature access to NYC, Greenwich, Westport and airports.

7 Beds ⋅ 10 Baths ⋅ 24104335 MLS

The Ultimate East Coast Sanctuary, Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning buyers who demand seclusion with proximity to NYC. This 38.91-acre compound is a one-of-a-kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence has been masterfully reimagined to incorporate 7 private bedroom suites, all with views over the landscaped property. The bespoke renovation was executed with uncompromising attention to detail and a true no-expense-spared philosophy, incorporating commercial-grade infrastructure, superior materials, and artisan-level craftsmanship throughout, as if cost were no consideration. Lofty ceilings and walls of glass are a perfect setting for an art collector. Separate wings radiate off the main rooms, each space private and thoughtfully composed. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. The barn pool house with full kitchen, bath and pro-grade gym, the pool, and a heated paddle court make this a perfect athlete's compound. Property includes renovated stone guest/caretaker cottage and a private office pavilion. The landscape offers open vistas, an orchard, and allowed equestrian use. Live in ultimate style and privacy surrounded by a 155-acre nature access to NYC, Greenwich, Westport and airports.

4800 Congress St, Fairfield

Listing courtesy of Leslie Razook from William Pitt Sotheby's Int'l. (203) 918-4452 (203) 966-2633

$14,995,000

Designed to be admired and built to be enjoyed, 33 Sears Rd is a custom residence set on 1.6 acres of manicured, private grounds. The home makes an immediate statement with a grand two-story foyer that introduces soaring ceilings, refined detailing, and beautifully scaled living spaces throughout. Built by one of Boston's premier female builders, the craftsmanship is evident in every threshold, finish, and room proportion. The open-concept main level was thoughtfully designed to offer grand room sizes without sacrificing warmth. A custom chef's kitchen appointed with top-tier appliances anchors the heart of the home, complemented by a separate, fully equipped prep kitchen. The primary suite features a dramatic two-story walk-in closet, a rare offering that quietly separates this residence from others on the market. Elevator infrastructure is already in place. Outdoor living is equally compelling, w/ ample acreage to accommodate a future pool, sport court, or other lifestyle amenities.

6 Beds ⋅ 8 Baths ⋅ 73537408 MLS

Designed to be admired and built to be enjoyed, 33 Sears Rd is a custom residence set on 1.6 acres of manicured, private grounds. The home makes an immediate statement with a grand two-story foyer that introduces soaring ceilings, refined detailing, and beautifully scaled living spaces throughout. Built by one of Boston's premier female builders, the craftsmanship is evident in every threshold, finish, and room proportion. The open-concept main level was thoughtfully designed to offer grand room sizes without sacrificing warmth. A custom chef's kitchen appointed with top-tier appliances anchors the heart of the home, complemented by a separate, fully equipped prep kitchen. The primary suite features a dramatic two-story walk-in closet, a rare offering that quietly separates this residence from others on the market. Elevator infrastructure is already in place. Outdoor living is equally compelling, w/ ample acreage to accommodate a future pool, sport court, or other lifestyle amenities.

33 Sears Rd, Brookline

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

$14,900,000

Panoramic views of Long Island Sound extend from this gated, resort-like estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, glass French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with spa. First floor rooms facing the water include the living room and office, both with fireplaces, the formal dining room and the open kitchen/family room. This floor also has a billiard/media room, full bar, refrigerated wine room, two powder rooms and laundry. Idyllic second floor primary suite features waterfront balcony and sitting room, 3 walk-in closets and marble bathroom. Three additional en-suite bedrooms, each with balconies, complete this level. Perched on the third floor is a home gym with waterfront balcony, full bath and sauna. Newly added wing above attached two-car garage with one-bedroom guest suite. Perfect for summer entertaining, the backyard terrace offers a bar with built-in barbecue and a sitting area with firepit by the pool. Beyond the manicured lawns, the 168-ft seawall leads to an 80-ft pier and 20-ft private dock. Side yard with secluded outdoor shower, exterior-access powder room and kayak storage rack. Spacious two-bedroom guest cottage with 1.5 baths, kitchen, laundry and attached one-car garage. Commercial-sized generator powers main house & cottage.

5 Beds ⋅ 9 Baths ⋅ 24179641 MLS

Panoramic views of Long Island Sound extend from this gated, resort-like estate. Designed to maximize its spectacular waterfront setting, the east-facing main house takes in the coastal views from walls of windows, glass French doors, and private balconies. Effortless indoor-outdoor flow defines the main level, where a charming screened-in porch and awning-covered veranda overlook a Gunite pool with spa. First floor rooms facing the water include the living room and office, both with fireplaces, the formal dining room and the open kitchen/family room. This floor also has a billiard/media room, full bar, refrigerated wine room, two powder rooms and laundry. Idyllic second floor primary suite features waterfront balcony and sitting room, 3 walk-in closets and marble bathroom. Three additional en-suite bedrooms, each with balconies, complete this level. Perched on the third floor is a home gym with waterfront balcony, full bath and sauna. Newly added wing above attached two-car garage with one-bedroom guest suite. Perfect for summer entertaining, the backyard terrace offers a bar with built-in barbecue and a sitting area with firepit by the pool. Beyond the manicured lawns, the 168-ft seawall leads to an 80-ft pier and 20-ft private dock. Side yard with secluded outdoor shower, exterior-access powder room and kayak storage rack. Spacious two-bedroom guest cottage with 1.5 baths, kitchen, laundry and attached one-car garage. Commercial-sized generator powers main house & cottage.

279 Saugatuck Ave, Westport

Listing courtesy of Joseph Barbieri from Sotheby's International Realty. (203) 618-3112 (203) 869-4343

$14,900,000

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner’s quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont.

7 Beds ⋅ 10 Baths ⋅ 5066210 MLS

Star Hill Farm is completely private, hidden on a hillside with pastoral and mountain views in the heart of South Woodstock. From the valley floor to the top of Meetinghouse Hill, you will be inspired by its beauty, a mesmerizing 183.7+/- acre oasis over gorgeous terrain with fields, woodlands, trails, and stone walls. The historic 2-bedroom guest house and party barn are fully restored, and located next to the swimming pond. The main residence, completed in 2010, consists of the center core with porch - for cooking, gathering and entertaining; the owner’s quarters with a 2nd floor suite and 2 bedrooms below; the guest wing with 3 first-level bedrooms, second-floor game room and adjacent 8-bed bunk room and a 4-story octagon with wine cellar at the base and flexible multi-use spaces above. All 7 bedrooms are ensuite plus 3 powder rooms. The attached gambrel barn is a professional grade gymnasium with 6-car heated garage underneath. The interior is like a grand lodge in the American West while the exterior with shingles and gambrel barn is traditional New England. The systems and mechanicals are all commercial grade. The finishes and craftsmanship are consistently superb. The atmosphere is relaxed and fun. As a complete fully furnished package, each and every attribute at Star Hill Farm - the location, land, exposure, privacy, views, guest house, barn, pond, residence and gymnasium- is exceptional, creating one of the finest properties in Vermont.

355 Greene Rd, Woodstock

Listing courtesy of Christopher W. Lang from Bravynia. ()

$14,900,000

Commanding ocean views from nearly every room, this extraordinary six acre estate sits on the historic site of a 1900s Manor House. Blending classic New England architecture with modern luxury, the stone-and-shingle residence features incredible design, custom mahogany, paneled walls and exquisite millwork throughout. The Primary Suite boasts panoramic ocean views, a domed gable ceiling, fireplace, walk-in closet with wet bar, and spa-like bath. All bedrooms are en suite with ocean views and closets with custom shelving. Formal gardens transition elegantly to sweeping seascapes directly above the beach. Enjoy the beach and the privacy Prides Crossing has to offer. A large,custom-built Poolhouse with kitchen and bath offers perfect indoor outdoor space. Designed for both grand entertaining and everyday comfort, this exceptional property captures the timeless beauty and elegance of Boston’s North Shore estates. A rare opportunity to own a legacy estate in an unmatched coastal setting.

5 Beds ⋅ 8 Baths ⋅ 73363224 MLS

Commanding ocean views from nearly every room, this extraordinary six acre estate sits on the historic site of a 1900s Manor House. Blending classic New England architecture with modern luxury, the stone-and-shingle residence features incredible design, custom mahogany, paneled walls and exquisite millwork throughout. The Primary Suite boasts panoramic ocean views, a domed gable ceiling, fireplace, walk-in closet with wet bar, and spa-like bath. All bedrooms are en suite with ocean views and closets with custom shelving. Formal gardens transition elegantly to sweeping seascapes directly above the beach. Enjoy the beach and the privacy Prides Crossing has to offer. A large,custom-built Poolhouse with kitchen and bath offers perfect indoor outdoor space. Designed for both grand entertaining and everyday comfort, this exceptional property captures the timeless beauty and elegance of Boston’s North Shore estates. A rare opportunity to own a legacy estate in an unmatched coastal setting.

53 Paine Avenue, Beverly

Listing courtesy of Listing Agent: Krista Julian from Listing Office: Coldwell Banker Realty - Manchester.

$14,889,000

Set along prestigious, bucolic Runnymede Drive, this exceptional seventeen-room legacy estate is privately sited on 4.6 park-like acres along a quiet side street within the only riverfront neighborhood east of I95 offering direct frontage on the Little River, distant ocean views, and the soothing sound of crashing surf. From the moment you arrive via the cobblestone driveway, it is clear this is a truly extraordinary property. Impeccably maintained grounds are thoughtfully designed to provide complete privacy while beautifully landscaped gardens deliver color and seasonal interest throughout the year. The riverside pool and pool house create an exceptional retreat for family and guests. Designed for effortless entertaining, the custom pool house features a gourmet kitchen rivaling that of the main residence and formal dining for ten overlooking the pool and river. The main home showcases timeless architecture, exquisite period craftsmanship, and custom millwork rarely found in today's luxury homes. Grand entertaining spaces include a distinguished library, elegant formal dining room, richly paneled lounge with intricate moldings, home theater, raised bar with walk-in wine cellar, and seamless access to outdoor living areas. Six beautifully appointed bedroom suites each feature luxurious en-suite tiled baths, including an expansive three-room primary suite with an extraordinary custom island dressing room and luxury marble bath with tub. Outstanding mechanical systems include multi-zone central air, automatic standby generator, sophisticated security system, and seven fireplaces, six of which have never been used. The remarkable craftsmanship and attention to detail throughout must be experienced firsthand. Seldom does an estate of this caliber, offering such exceptional privacy and meticulous care, become available just minutes from Abenaqui CC, the seaside boardwalks, shopping, Port City Air FBO terminal and under an hours drive from Logan International Jetport.

6 Beds ⋅ 9 Baths ⋅ 5105837 MLS

Set along prestigious, bucolic Runnymede Drive, this exceptional seventeen-room legacy estate is privately sited on 4.6 park-like acres along a quiet side street within the only riverfront neighborhood east of I95 offering direct frontage on the Little River, distant ocean views, and the soothing sound of crashing surf. From the moment you arrive via the cobblestone driveway, it is clear this is a truly extraordinary property. Impeccably maintained grounds are thoughtfully designed to provide complete privacy while beautifully landscaped gardens deliver color and seasonal interest throughout the year. The riverside pool and pool house create an exceptional retreat for family and guests. Designed for effortless entertaining, the custom pool house features a gourmet kitchen rivaling that of the main residence and formal dining for ten overlooking the pool and river. The main home showcases timeless architecture, exquisite period craftsmanship, and custom millwork rarely found in today's luxury homes. Grand entertaining spaces include a distinguished library, elegant formal dining room, richly paneled lounge with intricate moldings, home theater, raised bar with walk-in wine cellar, and seamless access to outdoor living areas. Six beautifully appointed bedroom suites each feature luxurious en-suite tiled baths, including an expansive three-room primary suite with an extraordinary custom island dressing room and luxury marble bath with tub. Outstanding mechanical systems include multi-zone central air, automatic standby generator, sophisticated security system, and seven fireplaces, six of which have never been used. The remarkable craftsmanship and attention to detail throughout must be experienced firsthand. Seldom does an estate of this caliber, offering such exceptional privacy and meticulous care, become available just minutes from Abenaqui CC, the seaside boardwalks, shopping, Port City Air FBO terminal and under an hours drive from Logan International Jetport.

15 Runnymede Dr, North Hampton

Listing courtesy of Patrick Carey from Carey Giampa, LLC/Seabrook Beach. (Cell: 603-583-1000)

$14,850,000

Privately set off Warren St, this exceptional Brookline estate spans over 3.6 acres of beautifully landscaped grounds and over 9,000 SF across four levels, with 6 bedrooms, 6 full and 2 half baths. A striking entry with a sweeping staircase leads to expansive, light-filled living and entertaining spaces rich with charm and detailed moldings. The main level features a mix of formal and informal spaces, multiple offices, and a beautifully designed kitchen with high-end appliances, custom cabinetry, and an eat-in dining area overlooking the grounds. Upstairs, the primary suite includes a luxurious bath and generous dressing rooms, along with five additional bedrooms, family room, and laundry. The serene third floor offers flexible space for a gym, studio, or additional living. Outside, the grounds are unmatched - a pond, patios, firepit, and hot tub perfect for entertaining and everyday living. A one-of-a-kind offering in one of Brookline's most sought-after neighborhoods.

6 Beds ⋅ 8 Baths ⋅ 73507123 MLS

Privately set off Warren St, this exceptional Brookline estate spans over 3.6 acres of beautifully landscaped grounds and over 9,000 SF across four levels, with 6 bedrooms, 6 full and 2 half baths. A striking entry with a sweeping staircase leads to expansive, light-filled living and entertaining spaces rich with charm and detailed moldings. The main level features a mix of formal and informal spaces, multiple offices, and a beautifully designed kitchen with high-end appliances, custom cabinetry, and an eat-in dining area overlooking the grounds. Upstairs, the primary suite includes a luxurious bath and generous dressing rooms, along with five additional bedrooms, family room, and laundry. The serene third floor offers flexible space for a gym, studio, or additional living. Outside, the grounds are unmatched - a pond, patios, firepit, and hot tub perfect for entertaining and everyday living. A one-of-a-kind offering in one of Brookline's most sought-after neighborhoods.

280 Warren St, Brookline

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$14,850,000

Timeless elegance meets modern luxury in this extraordinary Weston estate, situated on 5.3 stunning acres just minutes from Boston. Built by a renowned local builder and reimagined with Leslie Fine Interiors, this home blends superior craftsmanship, global influences and design. Bright, inviting spaces include a newly renovated kitchen, luxurious primary suite, soaring ceilings, and dramatic walls of glass. The property is a haven for entertaining, featuring a resort-style pool, pool house, orchard, indoor basketball court, private theater, and a space-themed arcade. Custom elements and unique spaces add sophistication, while a wine cellar, billiards/ping pong area, and expansive granite patios elevate the experience. Every inch of this masterpiece is crafted with exquisite attention to detail, offering a seamless fusion of elegance and comfortable living! A true destination home where art, design, and luxury converge to create an amazing property!

7 Beds ⋅ 12 Baths ⋅ 73493889 MLS

Timeless elegance meets modern luxury in this extraordinary Weston estate, situated on 5.3 stunning acres just minutes from Boston. Built by a renowned local builder and reimagined with Leslie Fine Interiors, this home blends superior craftsmanship, global influences and design. Bright, inviting spaces include a newly renovated kitchen, luxurious primary suite, soaring ceilings, and dramatic walls of glass. The property is a haven for entertaining, featuring a resort-style pool, pool house, orchard, indoor basketball court, private theater, and a space-themed arcade. Custom elements and unique spaces add sophistication, while a wine cellar, billiards/ping pong area, and expansive granite patios elevate the experience. Every inch of this masterpiece is crafted with exquisite attention to detail, offering a seamless fusion of elegance and comfortable living! A true destination home where art, design, and luxury converge to create an amazing property!

67 Byron Road, Weston

Listing courtesy of Listing Agent: Maggie Gold Seelig from Listing Office: MGS Group Real Estate LTD.

$14,500,000

A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for multigenerational living, private retreats, or legacy ownership. Altogether, the compound offers 11 bedrooms and 13 bathrooms across its collection of residences and guest accommodations. At its heart is the Robert A.M. Stern-designed main residence—an architectural work by one of America's most celebrated architects, whose residential designs are prized for their timeless elegance and lasting value. Complementing the estate is the architecturally striking Pond House, completed in 2021, featuring cathedral ceilings, exposed beams, shiplap detailing, a dramatic stone fireplace, screened porch overlooking the pond, and beautifully appointed interiors that rival the finest boutique hotels. A 1,700-square-foot Amish barn includes additional living quarters, and private driveways serving both parcels provide exceptional flexibility while maintaining complete privacy throughout the property. Resort-caliber amenities elevate the experience, including a heated 20' x 60' swimming pool, an exceptional pool house with a fully equipped gym, sauna, massage room, and a screened porch with fireplace for effortless indoor-outdoor entertaining. Conveying with the property is coveted membership in the exclusive Boldwater Association, granting access to a private Atlantic Ocean beach, boat landing, tennis courts, and pickleball—offering the best of Vineyard coastal living without sacrificing the remarkable privacy of this inland sanctuary. This is far more than a luxury home. It is a private estate where architecture, landscape, and thoughtful design become the defining amenities. For the discerning buyer who values land, beauty, and architectural pedigree above a traditional waterfront address, this is an irreplaceable Vineyard legacy property unlike anything else available today.

11 Beds ⋅ 13 Baths ⋅ 73552898 MLS

A rare offering of extraordinary scale and architectural significance, this 22-acre Martha's Vineyard estate represents a category of ownership seldom available on the Island. Designed around privacy, natural beauty, and enduring craftsmanship, the living spaces encompass more than 9,500 square feet across multiple thoughtfully designed structures, creating an unparalleled setting for multigenerational living, private retreats, or legacy ownership. Altogether, the compound offers 11 bedrooms and 13 bathrooms across its collection of residences and guest accommodations. At its heart is the Robert A.M. Stern-designed main residence—an architectural work by one of America's most celebrated architects, whose residential designs are prized for their timeless elegance and lasting value. Complementing the estate is the architecturally striking Pond House, completed in 2021, featuring cathedral ceilings, exposed beams, shiplap detailing, a dramatic stone fireplace, screened porch overlooking the pond, and beautifully appointed interiors that rival the finest boutique hotels. A 1,700-square-foot Amish barn includes additional living quarters, and private driveways serving both parcels provide exceptional flexibility while maintaining complete privacy throughout the property. Resort-caliber amenities elevate the experience, including a heated 20' x 60' swimming pool, an exceptional pool house with a fully equipped gym, sauna, massage room, and a screened porch with fireplace for effortless indoor-outdoor entertaining. Conveying with the property is coveted membership in the exclusive Boldwater Association, granting access to a private Atlantic Ocean beach, boat landing, tennis courts, and pickleball—offering the best of Vineyard coastal living without sacrificing the remarkable privacy of this inland sanctuary. This is far more than a luxury home. It is a private estate where architecture, landscape, and thoughtful design become the defining amenities. For the discerning buyer who values land, beauty, and architectural pedigree above a traditional waterfront address, this is an irreplaceable Vineyard legacy property unlike anything else available today.

10 & 12 Boldwater Road, Edgartown

Listing courtesy of Listing Agent: Michael Carucci from Listing Office: Serhant.

$14,500,000

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century 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.

19 Beds ⋅ 25 Baths ⋅ 73544510 MLS

The Wheatleigh: A Gilded Age masterpiece on over 21 pristine acres overlooking the Stockbridge Bowl. Designed in 1893 by Peabody & Stearns, this 16th-century 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.

11 Hawthorne, Stockbridge

Listing courtesy of Listing Agent: Steven Weisz from Listing Office: William Pitt Sotheby's International Realty.

$14,500,000

Completed in 2023 and designed by Michael Smith Architects, this extraordinary six bedroom waterfront residence offers more than 8,700 square feet of luxury living along one of Stamford's most coveted stretches of Ocean Drive West. Built two feet above FEMA flood elevation requirements and featuring sweeping views of Long Island Sound from every principal room, the home combines timeless coastal architecture, exceptional craftsmanship, and modern construction. Thoughtfully designed for both grand entertaining and everyday living, the residence balances expansive gathering spaces with private retreats, all oriented toward the water. A cedar shake exterior, stone detailing, and sunrise to sunset exposure define the home's striking waterfront presence. Across three levels, terraces, balconies, and principal living spaces are carefully positioned to capture panoramic views of Long Island Sound, creating a seamless connection between the interior and the surrounding landscape. The result is a residence equally suited for weekend escapes, year round living, and large scale entertaining.

6 Beds ⋅ 8 Baths ⋅ 24184829 MLS

Completed in 2023 and designed by Michael Smith Architects, this extraordinary six bedroom waterfront residence offers more than 8,700 square feet of luxury living along one of Stamford's most coveted stretches of Ocean Drive West. Built two feet above FEMA flood elevation requirements and featuring sweeping views of Long Island Sound from every principal room, the home combines timeless coastal architecture, exceptional craftsmanship, and modern construction. Thoughtfully designed for both grand entertaining and everyday living, the residence balances expansive gathering spaces with private retreats, all oriented toward the water. A cedar shake exterior, stone detailing, and sunrise to sunset exposure define the home's striking waterfront presence. Across three levels, terraces, balconies, and principal living spaces are carefully positioned to capture panoramic views of Long Island Sound, creating a seamless connection between the interior and the surrounding landscape. The result is a residence equally suited for weekend escapes, year round living, and large scale entertaining.

379 Ocean Dr W, Stamford

Listing courtesy of Josh Weisman from William Raveis Real Estate. (917) 882-7673 (203) 322-0200

$14,495,000

Set along prestigious Round Hill Road in backcountry Greenwich, this new construction estate offers a rare opportunity to create a modern country retreat of exceptional scale and refinement. At approximately 14,000 +/- SF with 7 bedrooms, the residence blends classic Greenwich architecture with a more contemporary sense of light, glass, and indoor-outdoor living. Plans include gracious formal and informal living spaces, a dramatic entry, private library, expansive kitchen, first-floor guest suite, elevator, and finished walkout lower level with golf simulator, wet bar, wellness gym, and cold plunge. Outdoor amenities include terraced landscaping, stone walls, a 20x40 pool with integrated spa, and a separate pool house with kitchenette, bath, and fireplace. Unique opportunity to customize select finishes and layout while in current stage. Renderings, plans, specifications, and features subject to change. A singular offering for those seeking a generational Greenwich estate with privacy, provenance, and architectural permanence.

7 Beds ⋅ 11 Baths ⋅ 24178299 MLS

Set along prestigious Round Hill Road in backcountry Greenwich, this new construction estate offers a rare opportunity to create a modern country retreat of exceptional scale and refinement. At approximately 14,000 +/- SF with 7 bedrooms, the residence blends classic Greenwich architecture with a more contemporary sense of light, glass, and indoor-outdoor living. Plans include gracious formal and informal living spaces, a dramatic entry, private library, expansive kitchen, first-floor guest suite, elevator, and finished walkout lower level with golf simulator, wet bar, wellness gym, and cold plunge. Outdoor amenities include terraced landscaping, stone walls, a 20x40 pool with integrated spa, and a separate pool house with kitchenette, bath, and fireplace. Unique opportunity to customize select finishes and layout while in current stage. Renderings, plans, specifications, and features subject to change. A singular offering for those seeking a generational Greenwich estate with privacy, provenance, and architectural permanence.

532 Round Hill Rd, Greenwich

Listing courtesy of Ian Defronze from Serhant Connecticut, LLC. (646) 637-8161 (203) 489-7800

$13,995,000

Perched atop nearly an acre of dramatic granite coastline with commanding ocean views, this extraordinary estate represents a level of craftsmanship that simply cannot be replicated today. Offered at $13,995,000 with an estimated replacement cost exceeding $37,000,000, it is a rare opportunity to own a truly irreplaceable residence. Spanning nearly 15,000 square feet, the home offers 6 bedrooms, 8 baths, an elevator, four fireplaces, a heated 5-car garage, ocean-facing infinity pool, rooftop deck, and spectacular entertaining spaces including a gallery. Every detail reflects an uncompromising commitment to artistry, from bespoke millwork and artisan stonework to exceptional materials sourced from around the world. Modern infrastructure includes 21-zone radiant heat and central air, backup generator, and state-of-the-art systems, creating a legacy estate where timeless craftsmanship meets extraordinary coastal living.

6 Beds ⋅ 8 Baths ⋅ 73542321 MLS

Perched atop nearly an acre of dramatic granite coastline with commanding ocean views, this extraordinary estate represents a level of craftsmanship that simply cannot be replicated today. Offered at $13,995,000 with an estimated replacement cost exceeding $37,000,000, it is a rare opportunity to own a truly irreplaceable residence. Spanning nearly 15,000 square feet, the home offers 6 bedrooms, 8 baths, an elevator, four fireplaces, a heated 5-car garage, ocean-facing infinity pool, rooftop deck, and spectacular entertaining spaces including a gallery. Every detail reflects an uncompromising commitment to artistry, from bespoke millwork and artisan stonework to exceptional materials sourced from around the world. Modern infrastructure includes 21-zone radiant heat and central air, backup generator, and state-of-the-art systems, creating a legacy estate where timeless craftsmanship meets extraordinary coastal living.

25 Rockyledge Road, Swampscott

Listing courtesy of Listing Agent: Willis + Tierney from Listing Office: Compass.

$13,950,000

In the lovely enclaves of Cotuit, Ma, positioned on a high-elevation bluff along Oregon Point, sits this 3.10 acre, 400 ft ocean beachfront, beautiful property. Hosting a grandfathered footprint of multi-structures, this family compound offers additional space for pool, along with existing infrastructures including; utilities, driveways, tennis court, beachfront accesses, and topographic foundations. Oregon Point is a special place with pristine shorelines along Nantucket Sound. This property is full of opportunities for you to add your custom renovation.

10 Beds ⋅ 9 Baths ⋅ 22602575 MLS

In the lovely enclaves of Cotuit, Ma, positioned on a high-elevation bluff along Oregon Point, sits this 3.10 acre, 400 ft ocean beachfront, beautiful property. Hosting a grandfathered footprint of multi-structures, this family compound offers additional space for pool, along with existing infrastructures including; utilities, driveways, tennis court, beachfront accesses, and topographic foundations. Oregon Point is a special place with pristine shorelines along Nantucket Sound. This property is full of opportunities for you to add your custom renovation.

190 Vineyard Road, Cotuit

Listing courtesy of Listing Agent: George Moussa (georgemoussa@COMCAST.NET) from Listing Office: LAER Realty Partners.

$13,950,000

In the lovely enclaves of Cotuit, Ma, positioned on a high-elevation bluff along Oregon Point, sits this 3.10 acre, 400 ft ocean beachfront, beautiful property. Hosting a grandfathered footprint of multi-structures, this family compound offers additional space for pool, along with its existing infrastructures including; utilities, driveways, tennis court, beachfront accesses, and topographic foundations. Oregon point is a special place, and with its pristine shorelines along Nantucket Sound, this property is full of opportunities for you to add your custom renovations and more.

10 Beds ⋅ 9 Baths ⋅ 73527306 MLS

In the lovely enclaves of Cotuit, Ma, positioned on a high-elevation bluff along Oregon Point, sits this 3.10 acre, 400 ft ocean beachfront, beautiful property. Hosting a grandfathered footprint of multi-structures, this family compound offers additional space for pool, along with its existing infrastructures including; utilities, driveways, tennis court, beachfront accesses, and topographic foundations. Oregon point is a special place, and with its pristine shorelines along Nantucket Sound, this property is full of opportunities for you to add your custom renovations and more.

190 Vineyard Road, Barnstable

Listing courtesy of Listing Agent: George Moussa from Listing Office: LAER Realty Partners.

$13,900,000

There is nothing like this on Lake Winnipesaukee. Offered together as a private Winter Harbor compound, 14 & 20 Gateway Road encompass approximately 3 acres +/- with approximately 370' +/- of combined waterfront, two residences, extensive docking, and a sandy walk-in beach. The centerpiece, completed in 2023, is an approximately 8,600-square-foot contemporary residence was engineered by Thornton Tomasetti. Brazilian black slate and engineered rift oak floors, solid rift oak interior doors, hand-selected natural quartzite, custom millwork, stained red cedar siding, Douglas fir porch ceilings, and IPE decking define the build. A fully integrated Control4 system governs lighting, climate, Lutron power shades, and distributed audio. An 800-amp electrical service is supported by 45 kW generator backup. Six bedrooms, six full baths, three half baths, generous gathering spaces, and multiple professional-grade kitchen and prep stations support serious entertaining. At 20 Gateway, a cantilevered steel boathouse with rooftop entertaining deck is paired with a no-profile boat lift, 50-foot aluminum Lift-A-Dock, and sandy walk-in beach. At 14 Gateway, 195 feet of Winter Harbor frontage includes expansive U-shaped covered docking with room for multiple boats and watercraft. The classic 1958 Winnipesaukee cabin at 14 Gateway sits on approximately two additional acres and offers three bedrooms, one full bath, warm wood interiors, and a broad lakeside deck. More time capsule than guest house, it provides a distinct counterpoint to the contemporary residence. This is a finished, move-in-ready Winter Harbor compound that brings together contemporary architecture, a preserved vintage lake cabin, approximately 370' +/- of waterfront, extensive boating infrastructure, and approximately 3 acres +/- in one exceptional offering. Please note all acreage, waterfrontage, sq footage, bedrooms and baths have been combined to reflect the whole compound.

9 Beds ⋅ 11 Baths ⋅ 5108354 MLS

There is nothing like this on Lake Winnipesaukee. Offered together as a private Winter Harbor compound, 14 & 20 Gateway Road encompass approximately 3 acres +/- with approximately 370' +/- of combined waterfront, two residences, extensive docking, and a sandy walk-in beach. The centerpiece, completed in 2023, is an approximately 8,600-square-foot contemporary residence was engineered by Thornton Tomasetti. Brazilian black slate and engineered rift oak floors, solid rift oak interior doors, hand-selected natural quartzite, custom millwork, stained red cedar siding, Douglas fir porch ceilings, and IPE decking define the build. A fully integrated Control4 system governs lighting, climate, Lutron power shades, and distributed audio. An 800-amp electrical service is supported by 45 kW generator backup. Six bedrooms, six full baths, three half baths, generous gathering spaces, and multiple professional-grade kitchen and prep stations support serious entertaining. At 20 Gateway, a cantilevered steel boathouse with rooftop entertaining deck is paired with a no-profile boat lift, 50-foot aluminum Lift-A-Dock, and sandy walk-in beach. At 14 Gateway, 195 feet of Winter Harbor frontage includes expansive U-shaped covered docking with room for multiple boats and watercraft. The classic 1958 Winnipesaukee cabin at 14 Gateway sits on approximately two additional acres and offers three bedrooms, one full bath, warm wood interiors, and a broad lakeside deck. More time capsule than guest house, it provides a distinct counterpoint to the contemporary residence. This is a finished, move-in-ready Winter Harbor compound that brings together contemporary architecture, a preserved vintage lake cabin, approximately 370' +/- of waterfront, extensive boating infrastructure, and approximately 3 acres +/- in one exceptional offering. Please note all acreage, waterfrontage, sq footage, bedrooms and baths have been combined to reflect the whole compound.

14 & 20 Gateway Rd, Wolfeboro

Listing courtesy of Margot Skelley from Compass New England, LLC. ()

$13,900,000

Situated between Appleton St & Riedesel Ave, this grand & prominent center entrance 7+ bed, 6.5 bath home was originally built in c.1803 has been painstakingly restored, elegantly modernized and expertly crafted for modern living. Ideally sited on a maturely landscaped 22,500+ sq ft lot, this gracious home rests behind an elegant white fence with antique walkways and restored balustrade. Welcomed onto the formal foyer by a graceful staircase, hardwood floors, restored period details and abundant natural light throughout. A large living room offers a fireplace, custom built-ins, and large winnows that overlook the front and side yards. A well placed banquet sized formal dining room offers a butlers door into the kitchen and a fireplace of its own. A sparkling eat in kitchen is complete with top-of-the-line appliances, large center island, two pantries, & a mudroom. Exquisitely finished lower level with 2 level wine storage, gym, media room, steam shower, & sauna! Oversized 1 Car Garage

7 Beds ⋅ 7 Baths ⋅ 73444242 MLS

Situated between Appleton St & Riedesel Ave, this grand & prominent center entrance 7+ bed, 6.5 bath home was originally built in c.1803 has been painstakingly restored, elegantly modernized and expertly crafted for modern living. Ideally sited on a maturely landscaped 22,500+ sq ft lot, this gracious home rests behind an elegant white fence with antique walkways and restored balustrade. Welcomed onto the formal foyer by a graceful staircase, hardwood floors, restored period details and abundant natural light throughout. A large living room offers a fireplace, custom built-ins, and large winnows that overlook the front and side yards. A well placed banquet sized formal dining room offers a butlers door into the kitchen and a fireplace of its own. A sparkling eat in kitchen is complete with top-of-the-line appliances, large center island, two pantries, & a mudroom. Exquisitely finished lower level with 2 level wine storage, gym, media room, steam shower, & sauna! Oversized 1 Car Garage

153 Brattle St, Cambridge

Listing courtesy of Listing Agent: Michael Harper from Listing Office: Coldwell Banker Realty - Boston.

$13,890,000

Exceptional new construction waterfront home set on a private cul-de-sac in one of Old Greenwich's most desirable enclaves. This custom-built residence offers 180-degree unobstructed water views from every bedroom and living space, with beautiful NYC skyline views. Designed for modern coastal living, the home spans three levels with six decks and seamless indoor-outdoor flow. Walls of glass and Nano folding doors open the main level directly to the water, leading to a newly built private dock ideal for boating and entertaining. The interior features 5 bedrooms, 5 full baths, and 2 powder rooms, with wide 10-inch plank floors throughout. The chef's kitchen is centered around a 22-foot quartz island and equipped with Wolf and Sub-Zero appliances, including double ovens, double dishwashers, and additional refrigerated drawers. A third-floor full kitchen offers added flexibility for guests or extended living. Spa-like baths include Lusso Stone fixtures, heated floors, towel warmers, and a Kohler smart toilet in the primary suite. Built to the highest standards with steel beam and pile construction, 16-foot FEMA compliance, and custom Marvin windows. Ideally located just moments from Old Greenwich village, train, and a short walk to schools, town, and beach, with private beach access.

5 Beds ⋅ 7 Baths ⋅ 24172344 MLS

Exceptional new construction waterfront home set on a private cul-de-sac in one of Old Greenwich's most desirable enclaves. This custom-built residence offers 180-degree unobstructed water views from every bedroom and living space, with beautiful NYC skyline views. Designed for modern coastal living, the home spans three levels with six decks and seamless indoor-outdoor flow. Walls of glass and Nano folding doors open the main level directly to the water, leading to a newly built private dock ideal for boating and entertaining. The interior features 5 bedrooms, 5 full baths, and 2 powder rooms, with wide 10-inch plank floors throughout. The chef's kitchen is centered around a 22-foot quartz island and equipped with Wolf and Sub-Zero appliances, including double ovens, double dishwashers, and additional refrigerated drawers. A third-floor full kitchen offers added flexibility for guests or extended living. Spa-like baths include Lusso Stone fixtures, heated floors, towel warmers, and a Kohler smart toilet in the primary suite. Built to the highest standards with steel beam and pile construction, 16-foot FEMA compliance, and custom Marvin windows. Ideally located just moments from Old Greenwich village, train, and a short walk to schools, town, and beach, with private beach access.

4 Little Cove Ln, Greenwich

Listing courtesy of Alexandra Allen from Corcoran Centric Realty. (203) 625-9500 (203) 625-9500

$12,999,900

In one of Chatham's most storied and visually captivating settings, adjacent to the iconic Mitchell River wooden drawbridge, this extraordinary waterfront estate--masterfully crafted by the renowned Eastward Companies--represents a rare convergence of architectural distinction, coastal heritage, and modern luxury. Spanning more than 6,200 square feet across three impeccably designed levels, the residence is a study in refined elegance and thoughtful scale. Every detail has been curated for a sense of timeless sophistication while embracing the natural beauty of its surroundings. The main level unfolds with effortless grace, where a grand open-concept kitchen and great room--anchored by one of four gas fireplaces--serves as the heart of the home. A formal dining room, butler's pantry, and coffee bar create an environment equally suited for intimate gatherings and elevated entertaining. Bathed in natural light, the breakfast room offers serene views over the resort-caliber outdoor setting, where a 16' x 36' Gunite pool with integrated spa and sun shelf, is set against the tranquil backdrop of the Mitchell River. The first-floor primary suite is a private sanctuary, appointed with a a spa-quality bath featuring radiant heated floors, a soaking tub, and a glass-enclosed shower. The upper level reveals a dramatic loft retreat with fireplace, wet bar, and private deck--an ideal vantage point to take in sweeping water views. A second primary suite, equally refined, is complemented by two additional guest bedrooms and baths. Above the garage, a substantial bonus room with its own deck captures panoramic vistas of Stage Harbor and the historic Chatham Coast Guard Boathouse. This home is further distinguished by its exceptional level of finish and infrastructure, including Wolf appliances, curated fixtures, central vacuum, whole-house generator, 400-amp electrical service, and professionally landscaped grounds supported by a private irrigation well. An outdoor shower completes the effortless indoor-outdoor lifestyle. A singular offering of enduring quality and provenance--this is more than a home; it's a legacy property in one of Cape Cod's most treasured waterfront settings.

4 Beds ⋅ 7 Baths ⋅ 22601380 MLS

In one of Chatham's most storied and visually captivating settings, adjacent to the iconic Mitchell River wooden drawbridge, this extraordinary waterfront estate--masterfully crafted by the renowned Eastward Companies--represents a rare convergence of architectural distinction, coastal heritage, and modern luxury. Spanning more than 6,200 square feet across three impeccably designed levels, the residence is a study in refined elegance and thoughtful scale. Every detail has been curated for a sense of timeless sophistication while embracing the natural beauty of its surroundings. The main level unfolds with effortless grace, where a grand open-concept kitchen and great room--anchored by one of four gas fireplaces--serves as the heart of the home. A formal dining room, butler's pantry, and coffee bar create an environment equally suited for intimate gatherings and elevated entertaining. Bathed in natural light, the breakfast room offers serene views over the resort-caliber outdoor setting, where a 16' x 36' Gunite pool with integrated spa and sun shelf, is set against the tranquil backdrop of the Mitchell River. The first-floor primary suite is a private sanctuary, appointed with a a spa-quality bath featuring radiant heated floors, a soaking tub, and a glass-enclosed shower. The upper level reveals a dramatic loft retreat with fireplace, wet bar, and private deck--an ideal vantage point to take in sweeping water views. A second primary suite, equally refined, is complemented by two additional guest bedrooms and baths. Above the garage, a substantial bonus room with its own deck captures panoramic vistas of Stage Harbor and the historic Chatham Coast Guard Boathouse. This home is further distinguished by its exceptional level of finish and infrastructure, including Wolf appliances, curated fixtures, central vacuum, whole-house generator, 400-amp electrical service, and professionally landscaped grounds supported by a private irrigation well. An outdoor shower completes the effortless indoor-outdoor lifestyle. A singular offering of enduring quality and provenance--this is more than a home; it's a legacy property in one of Cape Cod's most treasured waterfront settings.

157 Bridge Street, Chatham

Listing courtesy of Listing Agent: The Grattan Group (Dgrattan@cireab.com) from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$12,995,000

This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering one acre of east facing views that can be enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned by Christopher Plummer of The Sound of Music, the current owners have meticulously renovated and restored this cherished home with the renowned builders, Significant Homes and interior designer, Cindy Rinfret, Rinfret LLC. The architectural integrity has been preserved with comfort and quality for today's lifestyle. A world-class property.

5 Beds ⋅ 8 Baths ⋅ 24187039 MLS

This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering one acre of east facing views that can be enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned by Christopher Plummer of The Sound of Music, the current owners have meticulously renovated and restored this cherished home with the renowned builders, Significant Homes and interior designer, Cindy Rinfret, Rinfret LLC. The architectural integrity has been preserved with comfort and quality for today's lifestyle. A world-class property.

209-209 Long Neck Point Rd, Darien

Listing courtesy of Shelly Tretter Lynch from Compass Connecticut, LLC. (203) 550-8508 (203) 343-0141