Feature Properties

Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham, complete with deeded boat house! Encompassing over 4,000 square feet, this exceptional 5 Bdrm, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings and thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat with tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for family and guests. A walk-out lower level expands living space with an entertainment room and full bath. Features include new HVAC w/natural gas heat, Central A/C, outside shower, well-irrigation, spacious deck, yard with pool potential, and private stairs to the water. Beautifully sited on 1.83 acres of pastoral grounds, you'll enjoy over 230 feet of frontage on one of the most desirable boating waterways in Chatham, with deep water access to Nantucket Sound. This exceptional property just off the Chatham Loop offers both privacy and a picturesque natural setting only minutes to Town.

70 Judges Way, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski (lori@cireab.com) from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$5,450,000

6 Beds ⋅ 7 Baths ⋅ 22602494 MLS

Located within the coveted seaside enclave of Salten Point, this extraordinary custom-built home captures sweeping views of Barnstable Harbor and Sandy Neck Beach. Designed for elegant coastal living, the residence showcases exquisite craftsmanship and materials, including custom mahogany millwork throughout. Dazzling views take center stage immediately upon entering, with an open floor plan lined with walls of windows and French doors that lead to outdoor spaces offering a resort-inspired experience. A covered deck gives way to the breathtaking pool and spa area with a spacious terrace, outdoor kitchen, and fire pit. In the living room, a grand stone fireplace and custom built-ins create a sophisticated gathering space with an adjacent den. The chef's kitchen is ideal for cooking and entertaining on any scale, complete with a marble island, custom cabinetry, and professional-grade appliances including a Sub-Zero refrigerator and Wolf range. Direct access to a screened-in porch provides the perfect setting for al fresco dining. An en suite bedroom completes the first level, providing private quarters for guests. On the second floor, the primary suite features a large balcony with stunning views, a fireplace, and a luxurious bathroom with a walk-in shower and soaking tub. Three additional bedrooms - one en suite and two sharing a Jack-and-Jill bathroom - deliver well-appointed accommodations. A walkout lower level provides a multi-purpose space with built-in bunk beds, a TV area, and a fitness room. Additional highlights include an attached two-car garage and top-of-the-line heating and cooling systems with built-in air purification and dehumidification. This magnificent property is on town sewer, has deeded water access for swimming and kayaking, and is within walking distance of the wonderful restaurants and shops in Barnstable Village.

22 Kent Road, Barnstable

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

$5,450,000

6 Beds ⋅ 7 Baths ⋅ 73528133 MLS

Located within coveted Salten Point, this custom home captures sweeping views of Barnstable Harbor and Sandy Neck Beach. The open floor plan features mahogany millwork, walls of windows, and a living room with a grand stone fireplace and den. A chef’s kitchen boasts a marble island, Sub-Zero/Wolf appliances, and access to a screened-in dining porch. Outdoor amenities include a covered deck, pool, outdoor kitchen, and fire pit. An en suite guest bedroom completes the main level. Upstairs, the primary suite offers a private balcony, fireplace, and luxury bath with a soaking tub and walk-in shower, alongside three additional bedrooms (one en suite, two sharing a Jack-and-Jill bath). The lower level features built-in bunks, a TV area, and a fitness room. Equipped with a 2-car garage, top-of-the-line HVAC with air purification and dehumidification, and town sewer, the property includes deeded water access for swimming and kayaking, and is walking distance to Barnstable Village.

22 Kent Road, Barnstable

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

$5,450,000

5 Beds ⋅ 5 Baths ⋅ 73506909 MLS

Experience refined coastal living in this fully renovated waterfront, water view estate on the Oyster River in Chatham. Encompassing over 4,000 sqft, this exceptional 5-bedroom, 4-1/2 bath residence blends timeless elegance & luxurious touches throughout. Soaring cathedral ceilings & thoughtfully designed custom built-ins create a sense of openness and sophistication. A first-floor primary suite offers a private retreat w/tranquil water views, private bath & walk-in-closet. Four additional water view bedrooms provide comfort and flexibility for guests. A walk-out lower level expands living space with an entertainment room and full bath. New HVAC w/natural gas heat, Central A/C, outside shower, well-irrigation, spacious deck, yard with pool potential, and private stairs to the water. Beautifully sited on 1.83 acres of pastoral grounds, you'll enjoy over 230 feet of frontage on one of the most desirable boating waterways in Chatham PLUS deeded rights to a boat house steps away!

70 Judges Way, Chatham

Listing courtesy of Listing Agent: Lori Jurkowski from Listing Office: Christie's International Real Estate Atlantic Brokerage.

$5,398,000

5 Beds ⋅ 5 Baths ⋅ 73592351 MLS

Gracious and timeless historic single family attached home in Brookline's prestigious Fisher Hill Estates. This 5 bedroom/4.5 bath home offers more than 7,000 sqft of elegant living space with spectacular views of the Brookline Reservoir! This majestic home features period architectural details, a grand staircase, high ceilings, original built-ins and gleaming hardwood floors. Sundrenched by floor to ceiling windows, the main level offers a gracious living room/dining room with fireplace, a stunning mahogany library with fireplace, a beautiful family room, breakfast area and a chef's kitchen with direct access to a lovely garden area. The second floor primary suite features a spa like bath, walk-in closet, fireplace and a picturesque private deck with outstanding views. Completing this level is an additional en suite bedroom. The third floor offers two additional bedrooms and a full bath. The finished lower level features a direct entry guest suite with a living area, full bath and kitchen - perfect for an au pair. Completing this home is a two car detached garage and multiple outdoor private garden areas. Community amenities include pool and tennis court. Close to shopping, restaurants, schools, Downtown Boston and so much more! This home is definitely a must see!!

15 Catlin Road, Brookline

Listing courtesy of Listing Agent: The Jeff Groper Group from Listing Office: Coldwell Banker Realty - Newton.

$5,395,000

4 Beds ⋅ 7 Baths ⋅ 22605032 MLS

There are few settings on Cape Cod quite like this—and even fewer homes built with this level of thought, scale, and finish. Tucked privately along Ashumet Pond on 1.40 acres, this nearly 8,000-square-foot waterfront estate was clearly designed for an end user, with exceptional attention paid not only to aesthetics, but to how the home lives day to day. Seven fireplaces, soaring ceilings, dramatic expanses of glass, beautifully considered finishes, and water views from nearly every room create a residence that feels both substantial and remarkably refined. The home unfolds effortlessly for entertaining and everyday living, with a beautifully appointed chef's kitchen, a second full kitchen on the lower level, wet bar, media room, wine cellar, and multiple gathering spaces oriented toward the water. Four en-suite bedrooms include two primary suites, while a private office, gym, laundry hookups on every floor, and a heated garage speak to a level of planning and convenience rarely found in a home of this scale. Outside, the setting is equally exceptional, with a pool, generous terraces, fire pit, outdoor shower, private beach, and brand-new private dock right on Ashumet Pond.

26 Wheeler Road, Mashpee

Listing courtesy of Listing Agent: Johnny Hatem (johnny.hatemjr@elliman.com) from Listing Office: Douglas Elliman of MA, LLC.

$5,395,000

4 Beds ⋅ 7 Baths ⋅ 73583739 MLS

There are few settings on Cape Cod quite like this—and even fewer homes built with this level of thought, scale, and finish. Tucked privately along Ashumet Pond on 1.40 acres, this nearly 8,000-square-foot waterfront estate was clearly designed for an end user, with exceptional attention paid not only to aesthetics, but to how the home lives day to day. Seven fireplaces, soaring ceilings, dramatic expanses of glass, beautifully considered finishes, and water views from nearly every room create a residence that feels both substantial and remarkably refined. The home unfolds effortlessly for entertaining and everyday living, with a beautifully appointed chef’s kitchen, a second full kitchen on the lower level, wet bar, media room, wine cellar, and multiple gathering spaces oriented toward the water. Four en-suite bedrooms include two primary suites, while a private office, gym, laundry hookups on every floor, and a heated garage speak to a level of planning and convenience rarely found in a home of this scale. Outside, the setting is equally exceptional, with a pool, generous terraces, fire pit, outdoor shower, private beach, and brand-new private dock offering direct access to Ashumet Pond. This is the rare property where the architecture, amenities, craftsmanship, and setting have already been considered in full—allowing the next owner to simply move in and enjoy a home that would be extraordinarily difficult to replicate today.

26 Wheeler Rd, Mashpee

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

$5,375,000

4 Beds ⋅ 3 Baths ⋅ 24206034 MLS

Renegade Farm is a breathtaking 85+ acre luxury countryside estate where the romance of farm-to-table living meets the indulgence of a private resort. The sprawling grounds feature a beautifully appointed 4-bedroom main house(4,504 sq ft) & a completely separate, spacious 4-bedroom guest house(4,074 sq.ft) making it an unmatched haven for multi-generational gatherings and high-end entertaining. The Main house features a dreamy chef's kitchen with mountain views, wood-burning fireplaces in the living room and family room are among many of the home's special attributes. The guest house is almost identical in size to the main house and also boasts two wood-burning fireplaces-one in the living room and the other in the family/recreational room-and two kitchens, one on each floor. Both homes enjoy large screened-in porches and outdoor courtyards, and total privacy between the 2 homes. Outside, a large garden retreat offers a true estate lifestyle, while wide, manicured trails wind through the vast acreage to reveal stunning, panoramic mountain views. The property includes a custom gunite pool, a newly resurfaced private tennis court, and a large fruit and vegetable garden. Renegade Farm is more than just a property; it is a magical, self-contained oasis designed for absolute privacy, active leisure, and serene natural beauty. Nearby - Catamount & Butternut, private & public schools, Twin Lakes & Lakeville Lake, and charming towns of Lakeville, Salisbury,Sharon & Great Barrington

55-57 Brinton Hill Rd, Salisbury

Listing courtesy of Liza Reiss from Elyse Harney Real Estate. (860) 671-0288 (860) 435-0120

$5,350,000

5 Beds ⋅ 8 Baths ⋅ 73573262 MLS

Set within Wellesley’s coveted Dana Hall neighborhood, this exceptional Colonial has been transformed into a secluded retreat where architecture, craftsmanship, and livability come together beautifully. Renovated by Flavin Architects and Ken Vona Construction, the home showcases an exacting level of design and detail. A gracious two-story foyer introduces interiors filled with natural light, while quarter-sawn oak floors lead to the formal dining room, where floor-to-ceiling windows and glass doors open to a secluded patio. A bright solarium and inviting screened-in porch offer additional spaces to unwind and take in the surrounding landscape.At the heart of the home, the Bulthaup kitchen features premium appliances, a butler’s pantry, double ovens, a full-size wine cooler, and an expansive island that flows into the family room with vaulted ceilings, custom built-ins, and a stone gas fireplace. Five bedrooms and six full baths include a serene primary suite with soaring ceilings, a spa-inspired bath, and a private balcony overlooking the grounds. The finished lower level provides a gym, playroom, wet bar, wine cellar, media room, full bath, and entertainment area. Meticulously landscaped grounds complete this distinctive residence, offering an extraordinary setting for both everyday living and entertaining.

55 Ridge Hill Farm Rd, Wellesley

Listing courtesy of Listing Agent: Debi Benoit from Listing Office: William Raveis R.E. & Home Services.

$5,350,000

3 Beds ⋅ 4 Baths ⋅ 5099532 MLS

Sorgenfrei, German for "carefree" captures the spirit of this remarkable 68 acre property in one of South Woodstock's most desirable locations: a place where life slows and the beauty of the Vermont countryside takes center stage. At the end of a quiet road, the property combines sweeping mountain views, and exceptional privacy with a thoughtfully designed hand-crafted, timber frame home. Outside, perennial gardens give way to open pasture suitable for a few horses or sheep, woodland trails for riding, hiking, cross-country skiing, and snowshoeing and direct access to the GMHA trail system. Built in 2015, the three-bedroom residence is defined by soaring spaces, exposed fir beams, walls of glass, and craftsmanship that feels substantial without being formal. Nearly every principal room is oriented toward the eastern views, bringing the surrounding mountains and changing Vermont landscape into daily life. The main level is equally comfortable for quiet everyday living or a houseful of guests, with an open kitchen, dining area, and dramatic great room centered around a floor-to-ceiling double-sided stone fireplace. A more intimate sitting room, screened porch, expansive deck, and primary suite are also located on this floor. Upstairs are a loft office, two en suite guest bedrooms, and a media room. The walk-out lower level adds a gym, infrared sauna, workshop, and temperature-controlled wine room with capacity for approximately 1,000 bottles. An 18.5 kW solar array supports near net-zero living, while a three-bay garage accommodates vehicles, sporting equipment, and the gear that comes with an active Vermont life. Just minutes from Woodstock Village, 16 miles from Killington Resort, and 26 miles from Okemo Mountain Resort.

115 Eastman Rd, Woodstock

Listing courtesy of T Story Jenks from LandVest, Inc/Woodstock. ()

$5,300,000

5 Beds ⋅ 8 Baths ⋅ 73586522 MLS

October Hill, the original estate on Paine Avenue in historic Prides Crossing reflects the quiet grace and coastal character that define Boston’s Gold Coast. This magnificent 2.6 acre private property features original Olmsted-designed gardens, southern exposure, and breathtaking views of Baker’s and Misery Islands and Salem Sound, plus private beach access and a current mooring off the beach. Cherished and meticulously maintained by the same owners for more than 35 years, the home has benefited from several significant updates in the past 2 years including new windows, upgraded electrical systems, updated Primary suite and bath with custom walk-in closet, refinished floors, and fresh exterior and interior paint. Inside, timeless craftsmanship shines through original custom woodwork, hardwood floors, soaring ceilings, fireplaces, and an expansive eat-in kitchen. Ideal setting for both everyday living and elegant entertaining. A home gym, outdoor shower, hot tub and game room bring a touch of resort-style ease to daily life.

23 Paine Avenue, Beverly

Listing courtesy of Listing Agent: Gretchen Berg from Listing Office: J. Barrett & Company.

$5,300,000

5 Beds ⋅ 4 Baths ⋅ 73493300 MLS

This historically significant townhouse was built in the Greek Revival style in 1834 by Asher Benjamin. The house was owned by Benjamin’s heirs until 1925 and was rented to the family of the well known landscape architect Arthur Shurcliff for many years. The home has five bedrooms, a beautiful living room with floor to ceiling windows and great light, a formal dining room, a deck, and a spacious kitchen looking out on a small garden. The home has had a number of updates over the years, including the addition of an exterior iron balcony. A lovely wide staircase winds through the lower four floors. This gem is one of the prettiest houses on Beacon Hill.

9 West Cedar St, Boston

Listing courtesy of Listing Agent: Sally T. Brewster from Listing Office: Brewster & Berkowitz R. E..

$5,299,000

7 Beds ⋅ 9 Baths ⋅ 73493729 MLS

Stunning waterfront home in Squantum with sweeping ocean views from nearly every room. Defined by its nautical charm and breathtaking waterfront setting, this exceptional residence offers 7 bedrooms, 7 full baths, 2 half baths, a private office, media room, and a 3-car garage. Sun-filled living spaces, soaring ceilings, warm wood floors, and a custom kitchen with sleek cabinetry and high-end appliances create a perfect blend of comfort and luxury. Set directly on the water in Quincy’s premier coastal neighborhood, just moments from marinas, beaches, waterfront walks, and with easy access to Boston.

156 Crabtree, Quincy

Listing courtesy of Listing Agent: Joe Karam from Listing Office: Northeast Development & Investment, Inc..

$5,295,000

6 Beds ⋅ 7 Baths ⋅ 73590105 MLS

Striking new construction estate set on a quiet tree lined cul-del-sac in South Newton. Thoughtfully designed for modern living, the open floor plan is complimented by high ceilings and the finest finishes. The designers chef kitchen is a culinary showpiece, Wolf/Subzero appliances, stunning stone countertops & large island w/seating for 6, wet bar area and walk-in-pantry. The expansive living area has 19 ft. ceilings with a marble fireplace and filled with natural light anchored by sliding glass doors for seamless indoor/outdoor living opening up to a spacious/private leveled backyard. Main level features a dining room with beautiful millwork and designer light fixtures. Spacious office/first floor bedroom option and mudroom complete the first floor. Upstairs, 4 generously sized ensuite bedrooms await. The luxe primary suite includes fireplace, custom built-ins & spa-like bath with a steam shower and smart toilet. A laundry room with custom cabinetry equipped with washer/dryer and in-home dry cleaning unit. The lower level features an ensuite bedroom, entertaining area w/wet bar and a movie theater room. 3 car heated garage. Located within the acclaimed public school district, nearby vibrant shops/dining. Minutes to Boston.

65 Levbert Rd, Newton

Listing courtesy of Listing Agent: Stephanie Lau from Listing Office: Bellafi Real Estate, Inc..

$5,295,000

4 Beds ⋅ 5 Baths ⋅ 22600317 MLS

Extraordinary and rarely offered, this private estate in the heart of historic Sandwich commands sweeping, panoramic views of Cape Cod Bay from nearly 19 acres of secluded land. A true legacy property, the setting offers unmatched privacy, rolling grounds, and endless possibilities in one of Cape Cod's most coveted locations. The residence encompasses over 6,000 square feet and is designed to support both refined living and grand-scale entertaining, whether enjoyed as a seasonal retreat or year-round residence. Outdoor living is paramount, with a heated gunite pool, classic farmer's porch, and widow's walk serving as exceptional vantage points to take in the ever-changing bay views and coastal horizon. The property also features its own dedicated solar field, enhancing efficiency and sustainability. Rarely does an estate of this magnitude, acreage, and outlook become available—an exceptional opportunity to own a private sanctuary defined by space, serenity, and breathtaking water views. Town advised potential development opportunity. Buyer to perform all due diligence with the Town regarding zoning, subdivision, wetlands, and permitting.

19 Cedarville Road, East Sandwich

Listing courtesy of Listing Agent: Ashley T Brennan (Ashley.Brennan@GibsonSir.com) from Listing Office: Gibson Sotheby's International.

$5,295,000

4 Beds ⋅ 5 Baths ⋅ 73473408 MLS

Extraordinary and rarely offered, this private estate in the heart of historic Sandwich commands sweeping, panoramic views of Cape Cod Bay from nearly 19 acres of secluded land. A true legacy property, the setting offers unmatched privacy, rolling grounds, and endless possibilities in one of Cape Cod’s most coveted locations. The residence encompasses over 6,000 square feet and is designed to support both refined living and grand-scale entertaining, whether enjoyed as a seasonal retreat or year-round residence. Outdoor living is paramount, with a heated gunite pool, classic farmer’s porch, and widow’s walk serving as exceptional vantage points to take in the ever-changing bay views and coastal horizon. The property also features its own dedicated solar field, enhancing efficiency and sustainability. Rarely does an estate of this magnitude, acreage, and outlook become available—an exceptional opportunity to own a private sanctuary defined by space, serenity, and breathtaking water views

19 Cedarville Road, Sandwich

Listing courtesy of Listing Agent: Ashley Brennan from Listing Office: Gibson Sotheby's International Realty.

$5,250,000

6 Beds ⋅ 5 Baths ⋅ 73592699 MLS

Rarely does a Gilded Age landmark arrive so thoroughly reborn. Designed in 1905 by architect Alfred L. Darrow, 46 Powell Street commands a coveted corner lot in the Cottage Farm Historic District, guarded by carved stone griffins and a scrolled wrought-iron gate. Stone, stucco, half-timbered gables, carved-bracket eaves and a terra cotta roof frame approx. 7,028 SF of Arts & Crafts and Tudor Revival grandeur, delivered with every modern comfort. A 2022 renovation rewired the entire home (400-amp service, integrated alarm, smoke and CO detection, ADT security with outdoor cameras), added central air, a new gas boiler, radiant-heated floors, and a sensor-driven snow-melt driveway and rear walkway, all without sacrificing a single carved detail. Some original doors were repurposed as pocket doors. Step into a two-story marble and mosaic foyer beneath a barrel-vaulted, rosette-coffered ceiling. A hand-carved bridal staircase rises to a soaring atrium lit by leaded-stained glass restored by Jim Anderson of “This Old House”. Five fireplaces, a library with gilt-carved bookcases and medieval English plaster ceiling, and a Jacobean dining room with butler’s pantry set the formal stage. The chef’s kitchen, featured in New England Home magazine, pairs mahogany, burlwood, brass and marble with Visual Comfort lighting, a Sub-Zero refrigerator, Thermador six-burner range, coffee bar with refrigerated drawers, and an antique bell box. It opens to a breakfast nook, a rear deck and a sunlit solarium with domed plaster ceiling. Upstairs, the primary suite offers a fireplace with Roman-tile surround, two leaded-glass bay windows, dressing area, walk-in closet and dual-sink bath with radiant-heated floors. The second suite adds a marble fireplace, walk-in closet and Paris-Metro tiled bath beneath a Tiffany-style transom. Six bedrooms and 4.5 renovated baths. The third floor delivers a kitchenette, walk-in laundry, cedar closet with sauna potential and a cathedral-loft billiard room with king-post beams and Franklin stove, ideal for media or games. The 2,534 SF lower level offers open space and a wine cellar. Private parking for three in the heated driveway plus a detached 1919 Spanish Colonial two-car garage. Specimen plantings and old-growth trees surround the grounds, and commercial-grade internet serves modern households. Just 100 yards to Beacon Street and the C Line, under one mile to Kenmore Square and 2.5 miles to the Public Garden. A fully renewed architectural icon.

46 Powell Street, Brookline

Listing courtesy of Listing Agent: Ama Agumeh from Listing Office: Barrett Sotheby's International Realty.

$5,250,000

4 Beds ⋅ 5 Baths ⋅ 73571701 MLS

Brand-new and sun-filled, this exceptional shingle-style Gambrel is privately set on nearly an acre of professionally landscaped, level grounds just off coveted Shore Road, less than a block from the ocean. A refined coastal retreat, the 4-bedroom, 4.5-bath residence pairs exceptional craftsmanship with effortless luxury and gracious indoor-outdoor living. Beautiful millwork and 9' ceilings define the first floor, anchored by a vaulted beam-ceiling primary suite with a spectacular spa-inspired bath. The generous eat-in kitchen and family room feature a dramatic shiplap-vaulted ceiling and open to a sun-drenched patio surrounding a heated plunge pool and oversize yard with unlimited potential. A second-floor deck overlooks the secluded grounds, while an additional primary en-suite and two bedrooms and two more baths complete the upper level. Stroll to Chatham Bars Inn, the Fish Pier and Main Street - an enviable setting where the best of Chatham is truly at your doorstep.

106 Barcliff Ave, Chatham

Listing courtesy of Listing Agent: Jill Boudreau from Listing Office: eXp Realty LLC - Corporate Office.

$5,250,000

2 Beds ⋅ 2 Baths ⋅ 24201909 MLS

The rarest luxury is seldom the land itself. It is the time already devoted to revealing its full potential. Set amidst protected land along the coveted Kent-Sharon border, RockOak offers the uncommon advantage of beginning years ahead on the construction of a legacy estate. The completed retreat allows the property to be enjoyed immediately, while the future estate evolves. Overlooking the orchard, gardens, woodlands and long views it offers refined, comfortable living from the very first day. The estate unfolds like a private park of meadows, woodlands, orchards, gardens, dramatic elevations and a sheltered seasonal brook. Sweeping western sunsets, expansive northern vistas, and carefully composed landscapes ensure every season reveals a new perspective. Two parcels define the property's flexibility. The principal Sharon homesite occupies a commanding elevation and includes architectural design plans by architect, Scot Samuelson, AIA, NCARB for a 5,000+ sq ft residence. The 2nd parcel is in Kent & Sharon, reached by its own private drive. It rests quietly on the edge of a woodland above the brook and in the meadow below the principal Sharon site. Throughout the estate, thoughtful infrastructure has been integrated into the landscape, while historic woodland roads, stone walls, specimen trees, perennial gardens, fountains, scenic overlooks, and a distinctive 40 tree orchard create a landscape of exceptional beauty and permanence. Convenient access to NYC by car or train.

Sharon

Listing courtesy of Pels Matthews from W. Raveis Lifestyles Realty. (203) 671-5432 (860) 868-0511

$5,225,000

6 Beds ⋅ 4 Baths ⋅ 73472922 MLS

Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor shower, parking, and mini-split climate control; its upstairs bedroom enjoys views from Farm Pond to Nantucket Sound. Completing the property is the charming Lilac House, a fun open-concept bunk house with a full bath, water-view deck, and private outdoor shower. A wraparound porch captures sweeping ocean views, while beaches, shops, restaurants, Circuit Avenue, and the Harbor are moments away. An established rental history further enhances this rare opportunity in one of Oak Bluffs’ most iconic locations.

4 Canonicus Ave, Oak Bluffs

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

$5,200,000

5 Beds ⋅ 6 Baths ⋅ 73596081 MLS

Introducing a magnificent townhome ideally situated at the corner of Exeter and Beacon Streets in Boston’s prestigious Back Bay. Offering an extraordinarily rare opportunity to create a bespoke trophy residence, 299 Beacon Street pairs timeless architectural grandeur with exceptional potential for modern luxury living. Envisioned features and amenities include elevator access to all levels, parking, grand entertaining rooms, soaring ceilings, oversized bay windows and a beautiful roof deck. This extraordinary property presents the opportunity to create a showpiece townhouse in a coveted corner setting, moments from the Charles River Esplanade, Public Garden, and the fine shops and restaurants of Newbury Street.

299 Beacon Street, Boston

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

$5,200,000

5 Beds ⋅ 4 Baths ⋅ 73534187 MLS

Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an open-concept kitchen, dining, and living area, a private primary suite, office, screened porch, and expansive decks. Thoughtfully appointed with air conditioning, a whole-house generator, integrated sound system, and outdoor lighting. The grounds include a tennis court, landscaped gardens with a water feature, and several acres of open meadow surrounded by mature woodland, ensuring exceptional privacy with no visible neighboring homes. Ample room exists for a pool, and the parcel may offer subdivision potential. Ownership includes rights to Brickyard Beach.

49 Gosnolds Way, Chilmark

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.

$5,199,000

5 Beds ⋅ 8 Baths ⋅ 24201547 MLS

From the moment you enter the gates of this Old Hill estate, you know you've arrived- a rare sanctuary built with a level of custom stonework and craftsmanship impossible to replicate today. This stunning 5 bedroom, 6.2 bath home offers an extraordinary blend of elegance, privacy, and nature. Set in a mature landscape that takes generations to establish, the setting delivers unmatched wildlife views-from herons and owls to ducks and otters along picturesque Stony Brook. Resort-style amenities feature a heated saltwater pool/spa, a private pond with a fountain, and deeded access to nearby Nash's Pond for kayaking and fishing. Inside, a dramatic wall of glass captures sweeping water views, creating a seamless connection to the outdoors. The main level includes a gourmet kitchen, family room with fireplace, dining room with wet bar, living room with fireplace and lounge, stone entry foyer, mudroom and two powder rooms. Upstairs, the primary suite boasts two terraces, dual walk-in closets, and a spa bath. Four additional bedrooms each with its own bathroom, a sprawling home office/6th bedroom with fireplace, a large playroom with a full bath, a third floor family room, and a mirrored gym/yoga studio with a ballet barre offer exceptional living options. Moments from Earthplace nature trails, key features include a heated 3-car garage, Crestron lighting, full-house generator, and a built-in poolside gas grill. A rare opportunity to own a sanctuary where design and nature converge.

31 Stonybrook Rd, Westport

Listing courtesy of Kristi Law from William Pitt Sotheby's Int'l. (917) 576-6638 (203) 227-1246

$5,195,000

6 Beds ⋅ 8 Baths ⋅ 24197551 MLS

On one of New Canaan's most coveted streets, 25 Adams Lane stands as a rare offering: exceptional architecture, extraordinary amenities, and the kind of warmth that cannot be built - only lived. Set on two glorious south-facing acres, the property commands one of the finest front lawns in town; a sweeping, softly grassed acre framed by mature flowering trees, and longtime home to the neighborhood's beloved annual Turkey Bowl. The fully enclosed backyard, bordered by a gently running creek and cathedral of mature trees, delivers the privacy of a country estate within one of New Canaan's most beloved neighborhoods. This spacious residence offers six bedrooms, six full and two half baths across four thoughtfully designed levels. Step inside to soaring 9-foot ceilings, extensive custom millwork, and windows positioned to flood every room with southern light. The open-plan kitchen anchored by two large islands and appointed with Sub-Zero, Wolf, and Thermador, rises to every occasion. Five fireplaces warm the principal gathering spaces, including a handsome paneled study ideal for working from home. The primary suite features a fully custom dressing room and stunning new bath (2025). A private sitting room with three walls of windows, suspended among the treetops, redefines what a home office can be. The finished third floor serves as playroom, studio, or guest quarters. The lower level delivers a nine-seat home theater, well-appointed gym, and wine cellar.

25 Adams Ln, New Canaan

Listing courtesy of Christine Saxe from Compass Connecticut, LLC. (203) 273-1548 (203) 442-6626

$5,195,000

8 Beds ⋅ 9 Baths ⋅ 24182442 MLS

West Winds is one of Washington's most extraordinary country estates, offering an unparalleled combination of privacy, natural beauty, recreation, and equestrian amenities. A long, winding drive meanders through expansive meadows and orchards, culminating at a remarkable 10,000+ square-foot barn-style residence. Meticulously crafted using reclaimed beams and siding from a 19th-century Dutch barn, the home blends authentic historic character with modern comfort and scale. Set on 62 acres across 4 separate parcels, the property enjoys over 1,000 feet of frontage along the Bantam River, with sweeping views across the water to the mountains beyond (including iconic Mt. Tom). Outdoor amenities are exceptional, highlighted by a spectacular infinity-edge pool surrounded by stone terraces and walls, a private pond for fishing and winter skating, and direct access to miles of protected land trust trails ideal for hiking, biking, horseback riding, and exploring the surrounding countryside. For equestrian enthusiasts, West Winds offers a rare opportunity to ride directly from the property onto adjacent trail networks that follow the scenic Bantam River. The horse facility includes 4 stalls, tack area, and paddocks creating a turnkey setup for both recreational and serious riders. The heart of the home is the renovated eat-in kitchen, ideally positioned between the dramatic vaulted great room and the expansive media/game room.

56 W Morris Rd, Washington

Listing courtesy of Stacey Matthews from W. Raveis Lifestyles Realty. (203) 671-9067 (860) 868-0511

$5,195,000

5 Beds ⋅ 8 Baths ⋅ 73452478 MLS

WHY 70 McCALLAR? The rare opportunity to enjoy BRAND-NEW CONSTRUCTION on two private acres, less than one mile from historic Concord Center, with sidewalks leading into town. This exceptional 7,400+ SF residence combines timeless New England architecture with the comfort, efficiency, and peace of mind of new construction. Thoughtfully designed for both grand entertaining and everyday living, the home features 10-foot ceilings, expansive windows, exquisite millwork, white oak floors, five en suite bedrooms, and a luxurious primary retreat. Enjoy the privacy of an estate-like setting without sacrificing convenience to Concord's shops, restaurants, cultural attractions, and nearby Emerson Hospital. From its beautifully appointed interiors to its exceptional outdoor living spaces, every detail reflects quality and thoughtful design. A remarkable opportunity to enjoy the best of Concord living without the compromises of renovating an older home. Meet the Builder anytime and ask your questions.

70 Mccallar Lane, Concord

Listing courtesy of Listing Agent: Jim J. D Agostine from Listing Office: Country Real Estate Inc..

$5,125,000

4 Beds ⋅ 5 Baths ⋅ 22604782 MLS

Awaken to sweeping, unobstructed views of Nantucket Sound from this meticulously crafted new build in Falmouth. Custom-designed for the discerning Cape Cod buyer. Serving as your private gateway to the quintessential Cape lifestyle, this exceptional property places you moments away from renowned local shores and an association beach option. Here, your days unfold effortlessly across a birding paradise perfect for windsurfing, swimming, and sun-drenched lounging, or exploring the nearby Shining Sea Scenic Bikeway. Ideal for avid boaters and nature enthusiasts alike, the location offers seamless access to nearby harbors and marinas, complemented by daily sightings of native coastal birds, wildlife and serene spaces for your garden. Equipped with modern conveniences including a garage that lives like an organized haven keeping everything at an arm's reach, an EV charger and a whole-house generator, every thoughtful detail ensures absolute peace of mind, creating an extraordinary sanctuary where coastal adventure and timeless memories await. The immediate area provides a long list of places to experience. Spohr Gardens is a breathtaking 6-acre woodland garden that can be easily accessed near the property. Spohr Gardens features a succession of seasonal blooms including thousands of daffodils, daylilies, rhododendrons, and azaleas, all set along paths with sweeping views of Oyster Pond and Nantucket Sound. Additionally, these winding trails are uniquely integrated with whimsical nautical artifacts, vintage lanterns, large millstones, and old ship anchors. Just a little further away some of the other areas include. The Knob is a scenic coastal nature area with narrow paths winding through a wooded peninsula to panoramic waterfront vistas. Oyster Pond Environmental Trust manages serene, low-impact passive paths through protected marshlands and coastal pond habitats. Beebe Woods is an expansive 383-acre forest featuring an extensive network of shaded dirt paths and carriage roads winding around scenic ponds and rolling hills. Two Ponds Conservation Area provides quiet dirt and boardwalk paths that loop through tranquil woodlands and wetland environments. Coonamessett Greenway Heritage Trail is a scenic pathway following the river corridor through cedar swamps, pine forests, and open fields.

87 Oyster Pond Road, Falmouth

Listing courtesy of Listing Agent: Amy E Vickers (sustainablecapecod@gmail.com) from Listing Office: Sotheby's International Realty.

$5,100,000

5 Beds ⋅ 4 Baths ⋅ 73578429 MLS

Welcome to 97 Oakmont, an extraordinary Montana-built log cabin retreat set on 80 private acres in Westminster. Combining exceptional craftsmanship, natural beauty, and unmatched privacy, this is the kind of property that rarely comes to market. The 5+ bedroom home showcases soaring log timbers, a dramatic fireplace, warm wood interiors, and expansive decks designed to take full advantage of the stunning surroundings. Nearly every room offers a view, including the beautifully positioned kitchen boasting Dakota mahogany granite countertops, overlooking the fields, meadows, and rolling landscape beyond. A second-floor office with water views provides a peaceful place to work, create, or simply enjoy the quiet. Outside, the property is just as impressive. Enjoy direct access to Croker Pond with your own private dock and views of the pond's two islands. Whether you're kayaking, fishing, paddleboarding, or simply enjoying a morning coffee by the water, the setting is nothing short of spectacular. The 80 acres offer a rare mix of open meadows, mature woods, and established trails for walking, hiking, exploring, and enjoying nature right outside your door. Organic fields free of chemical fertilizers, abundant wildlife, and a mature maple grove with maple syrup production potential create a property that feels both private and purposeful. The finished walk-out lower level includes a separate living area with direct access to a covered patio, creating a seamless connection to the outdoors and offering some of the property's most beautiful views. The lower garage allows you to park your snow mobile at the end of the day. While the setting feels worlds away, you're just minutes from everything Westminster has to offer, including local restaurants, shopping, Wachusett Mountain, golf, and year-round outdoor recreation. Route 2 and the Fitchburg commuter rail provide convenient access to Boston and surrounding communities.97 Oakmont is more than a home—it's a private New England estate offering waterfront living, extensive acreage, recreational opportunities, and the kind of peace and tranquility that is increasingly difficult to find. A truly rare opportunity.

97 Oakmont Ave, Westminster

Listing courtesy of Listing Agent: The Edwards Realty Team from Listing Office: Barrett Sotheby's International Realty.

$5,100,000

3 Beds ⋅ 7 Baths ⋅ 73511019 MLS

Situated on a lovely street, this very special five story townhome has it all. There are three plus bedrooms with potential for more as the top floor with an open floor plan and sunny balcony offers great flexibility. Wonderful entertaining space and formal rooms with beautiful proportions and architectural details add to the charm. A door from the living room opens out to an extraordinary deck with a balustrade. The bright, eat-in kitchen with large windows looks out on the inviting garden. Amenities include a finished basement with a garden room and lots of storage.

52 Pinckney St, Boston

Listing courtesy of Listing Agent: Sally T. Brewster from Listing Office: Brewster & Berkowitz R. E..

$5,095,000

6 Beds ⋅ 7 Baths ⋅ 24210273 MLS

2026 Riverside Harborview New Construction by Frattaroli Construction Group. A statement in modern luxury, this 6-bedroom, 6.1-bath residence situated on a desirable cul-de-sac in sought-after Riverside, CT. Embrace the coveted Riverside lifestyle, with the train station within walking distance and easy access to beaches, dining, shopping. Blending contemporary architecture with timeless design and details through-out, this exceptional home offers refined living across four finished levels. A multi-slide glass wall seamlessly connects indoor-outdoor living, opening to an expansive deck's ideal for gatherings and entertaining with harbor and sunset views. A dramatic sweeping staircase, walls of glass and white oak flooring create a light-filled, contemporary aesthetic. Open living spaces feature a Calacatta marble fireplace and custom white oak built-ins. The designer kitchen showcases a 9-foot marble island, white rift oak cabinetry, butler's and walk-in pantries, and a curated wine display. The stunning primary suite offers soaring vaulted ceilings, a custom dressing closet and a spa-inspired Calacatta Gold bath with soaking tub and dual vanities. An en-suite first-floor bedroom, private office with custom built-ins, third-floor lounge with balcony, media/playroom, 2-car garage and level yard complete this striking modern family residence.

8 Somerset Ln, Greenwich

Listing courtesy of Kimberly Frattaroli Horlacher from William Raveis Real Estate. (203) 550-3552 (203) 869-9263

$5,000,000

5 Beds ⋅ 7 Baths ⋅ 73582552 MLS

What if your favorite destination was home? Set on one of Southborough’s most distinguished streets, 3 Wyndemere Drive is a residence designed for both extraordinary moments and beautifully lived everyday life - a place where timeless elegance, exceptional amenities and effortless comfort come together. From the moment you enter, soaring spaces, refined architectural details and an elegant flow create a sense of presence without sacrificing warmth. Expansive windows fill the interiors with natural light and capture views of the picturesque wildflower meadow and surrounding conservation land. At the heart of the home, beautifully appointed gathering spaces transition effortlessly from quiet mornings to intimate dinners and memorable evenings. The main-level primary suite is a world of its own - generously scaled, private and designed around the rituals of everyday luxury. A serene sitting room opens to a private balcony, while two exceptional walk-in closets create beautifully designed spaces for dressing, displaying and organizing a wardrobe with room to truly indulge. And then there’s downstairs, where an entirely different experience awaits. The expansive lower level is dedicated to entertaining, wellness and fun, with a sophisticated bar and oversized island, wine display, indoor grill, golf simulator and putting area, fitness space and impressive indoor jet pool. Perfect your swing, work out, gather for drinks or entertain late into the evening - all without ever making a reservation! Outside, approximately 4.6 acres of manicured grounds create a remarkable sense of privacy and a beautiful backdrop through the changing seasons. Generous living spaces, multiple levels of thoughtfully designed amenities and a three-car garage complete a residence created for life on a grand scale - yet with the warmth and versatility to feel equally at home during quiet everyday moments. Perfectly positioned in Southborough, the residence offers the rare combination of privacy and accessibility, with Fay and St. Mark’s schools nearby and Boston approximately 25 miles away - keeping exceptional education, culture and city access within easy reach. Elegant yet unexpected, sophisticated yet meant to be lived in, 3 Wyndemere Drive offers something increasingly rare: the freedom to entertain, play, recharge and enjoy life entirely on your own terms. This isn't simply a home to see. It's one to experience.

3 Wyndemere Dr, Southborough

Listing courtesy of Listing Agent: Edith Paley from Listing Office: William Raveis R.E. & Home Services.

$5,000,000

3 Beds ⋅ 3 Baths ⋅ 24192754 MLS

Some properties are defined by the house that sits on them. Others are defined by the land itself...by history, landscape and a sense of beauty that simply cannot be created. This is such a place. Owned and farmed by the same family for 200 years, this remarkable 16 Acre piece sitting on the Hammonassett River is the last piece of the original farm to be sold. With over 1500 ft. bordering the river, the property unfolds across open hay fields, tidal marshes and expansive river views. The landscape changes with the seasons and the light, grasses moving with the wind and water reflecting the ever changing sky...a landscape that is both bucolic and breathtaking. This is an exceptional setting for a distinctive country residence, a private retreat or a place to enjoy a quieter chapter of life. An existing, well appointed, three bedroom ranch home sits on the property and enjoys the same remarkable views. Comfortable as it stands, the home could ultimately serve as a guest house, artist's studio or private office. The property offers the potential for more than one lot, but with generations of family ownership, the sellers have hopes to see the land remain intact, so no soil testing has been undertaken for subdivision. A survey is available and buyers considering additional development should conduct their own due diligence. After two centuries in the same family, this is a rare opportunity to become the next steward of an extraordinary Connecticut landscape.

118 River Rd, Madison

Listing courtesy of Judy Dannemann from William Raveis Real Estate. (203) 675-8944 (203) 318-3570

$4,999,999

7 Beds ⋅ 5 Baths ⋅ 73586949 MLS

Introducing the newly reimagined 18 Hereford Street, an exceptional Back Bay single-family residence offering remarkable scale, soaring ceilings, oversized windows, and abundant natural light. Built circa 1871 for builder and contractor George Martin Gibson, this distinguished home is one of four contiguous residences he developed on the block. (Historical information from the Back Bay Houses website). A gracious foyer welcomes you inside, opening to an elegant living room and an adjoining formal dining room. A dramatic curved staircase leads to the second floor, the heart of daily living, with a warm den, inviting dining space, a kitchen with stainless-steel appliances and granite countertops, and a full bath. The third floor offers three generously proportioned bedrooms and a full bath. Three additional bedrooms, another full bath, and a laundry room occupy the fourth floor. Either upper level offers excellent flexibility for creating a spacious, customized primary suite. Fully renovated in 2023, the garden level opens directly to a charming brick patio and features a kitchenette, full bath, and versatile bedroom—ideal for guests, an au pair, a home gym, or a family room. Thoughtful updates include electrical, heating, and HVAC improvements. Rental parking is available nearby. Ideally situated in Back Bay, 18 Hereford Street is moments from the neighborhood’s shopping, dining, green space, and cultural amenities.

18 Hereford St, Boston

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

$4,999,999

5 Beds ⋅ 5 Baths ⋅ 5111744 MLS

A striking blend of contemporary architecture and classic New England character, this exceptional 4,350 square-foot residence sits at the end of a quiet cul-de-sac on two private acres, abutting 11 acres of conservation land and just one mile from Jenness Beach. Completely rebuilt in 2024–25, the home marries sophisticated design with the quality and efficiency of modern construction. Exposed steel beams and high ceilings define the dramatic open-concept living spaces, French Oak flooring brings warmth and continuity throughout the first floor and primary wing. A two-story foyer sets the tone upon entry. The heart of the home is an expansive eat-in kitchen featuring an 11-foot island, Sub-Zero and Wolf appliances, and a separate butler’s pantry with sink and wine refrigerator—ideal for both everyday living and effortless entertaining. A formal dining room provides a more refined setting for gatherings. The main level also offers a beautifully appointed home office with a gas fireplace and media center, along with a spacious mudroom providing direct access to the three-car garage. The private primary wing is thoughtfully positioned just one-half flight above the main level and features a luxurious en-suite bath with an oversized shower, soaking tub, heated towel racks, washer and dryer and double vanity sinks, along with a walk-in closet, dedicated dressing room, and an additional room for an office, gym, or extra closet space. Three additional en-suite bedrooms occupy the second floor, accessed by the main staircase, along with a conveniently located laundry area. Throughout the home, expansive Andersen E-Series windows frame peaceful views of the surrounding landscape. With the rear of the home oriented south, natural light fills the living spaces throughout the day. A spacious deck extends the living area outdoors for al fresco dining and entertaining.The finished walkout basement adds an additional 1000 SF that includes a media room and recreation room.

53 Spring Rd, Rye

Listing courtesy of Jennifer Madden from Gibson Sotheby's International Realty. ()

$4,999,999

5 Beds ⋅ 8 Baths ⋅ 24170471 MLS

Set beyond stone walls and a landscaped entrance, 48 Old Farm Road is a newly completed Wilton residence blending timeless New England architecture with a bright, refined modern interior. The open central hall makes an immediate impression with pale oak floors, abundant natural light and a striking staircase with black metal balusters. Generously proportioned living spaces feature custom millwork, expansive windows and seamless flow for everyday living and entertaining. The kitchen opens to the main gathering areas and overlooks the rear grounds. Spacious bedrooms include vaulted ceilings, large windows and beautifully finished baths with stone surfaces, frameless glass showers and thoughtfully selected fixtures. An elevator adds convenience between levels, while the three-car garage, broad driveway and multiple covered outdoor areas enhance daily function. Mature trees, open lawn, stonework and a private setting create the feel of a composed country property. The detached 2000 sq. ft. accessory building ready to be finished. Room for a pool. Served by Wilton Public Schools and convenient to Wilton Center, local amenities and Metro-North service to New York City.

48 Old Farm Rd, Wilton

Listing courtesy of Kevin O'Brien from O'Brien Premier Properties. (203) 943-9586 (203) 822-2524

$4,999,000

5 Beds ⋅ 7 Baths ⋅ 5098585 MLS

A breathtaking country estate seamlessly integrated into the Vermont landscape, this exceptional two residence compound offers refined living less than two miles from Stowe Mountain Resort and just minutes to the charm of Stowe Village. Masterfully reimagined, the property blends timeless design with superior craftsmanship and luxurious comfort. The main residence spans over 10,000 square feet of beautifully finished interiors, complemented by a separate guest house, each designed to elevate daily living and effortless entertaining. A meticulous renovation showcases the highest quality materials and artisan level detailing throughout, including custom millwork, wideplank flooring, finely crafted cabinetry, and premium appliances. Every space reflects an uncompromising commitment to excellence. Outside, a tiered, drylaid stone patio sets the stage for unforgettable outdoor living, featuring a hot tub, dining terraces, and panoramic mountain views. A tranquil pond enhances the natural beauty and serenity of the setting. This is a rare opportunity to own a legacy estate in one of Vermont’s most sought-after locations, crafted with extraordinary care for generations to come.

235 Lower Sanborn Rd, Stowe

Listing courtesy of Smith Macdonald Group from Coldwell Banker Carlson Real Estate. ()

$4,999,000

5 Beds ⋅ 9 Baths ⋅ 24146882 MLS

A rare offering, this Gambrel shingle-style estate is a sanctuary on over 15 acres with a lake and separate building lot-ideal for equestrian pursuits or a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered ceilings elevate the space. At the heart of the home, a stunning marble kitchen outfitted with Subzero and Wolf appliances, a breakfast nook, and butler's pantry opens to a soaring two-story family room as well as formal dining and living rooms for effortless entertaining. A main level bedroom suite is ideal for guests. Two private offices and well appointed mudroom enhance everyday functionality, while four fireplaces add warmth to the home. Upstairs, a spectacular primary suite with balcony, and 3 additional ensuite bedrooms are accompanied by a spacious bonus room with adjoining craft room. Intricate millwork and custom built-ins enrich every inch of this special home, reflecting its master craftsmanship. Wraparound covered patios overlook the saltwater Gunite pool, while an outdoor kitchen and fire pit invites alfresco dining. Pool house with kitchenette, laundry, 2 baths, rec room with balcony is perfect for guests. Five garage bays for the car enthusiast. The property offers unmatched luxury. Quite simply, there is nothing else like it.

294 Maple Rd, Easton

Listing courtesy of Linda Toscano from Coldwell Banker Realty. (203) 520-7899 (203) 245-4700

$4,995,700

4 Beds ⋅ 5 Baths ⋅ 24176377 MLS

Come walk this stunning 1.5 acre lot with me - totally private, tucked at the end of a cul de sac in Long Lots. Peace, quiet, and the highest quality custom home spec'd to your wishlist by Coastal Luxury Homes is yours at 22 Dawn Drive. Go bigger/smaller, add an in-law suite or extra bedroom, an art studio, include a pool/spa, pickle court... let's discuss all the possibilities. Square footage and specs can vary, but the standard of excellence does not. Coastal Luxury Homes is the premier Fairfield County bespoke builder.

22 Dawn Dr, Westport

Listing courtesy of Jaclyn Picarillo from Higgins Group Bedford Square. (203) 981-5012 (203) 226-0300

$4,995,000

4 Beds ⋅ 7 Baths ⋅ 73591255 MLS

A rare offering in New Seabury, this extraordinary custom-built residence overlooks the 18th fairway of the Ocean golf course at New Seabury Country Club, where sweeping golf course views meet refreshing ocean breezes. Designed by William Harris Architects of Atlanta in the genre of renowned architect A.M. Stern, celebrated for his distinguished private residences in the Hamptons and fine resort designs, including Disney's Yacht and Beach Club Resorts at Walt Disney World, this home reflects a distinctive architectural vision and timeless elegance. Offering over 6,000 square feet of luxurious living space, this exceptional residence features four bedroom en-suites, three half baths, and beautiful hardwood floors throughout. Three thoughtfully designed levels of living, along with a full basement, are conveniently accessible by private elevator or elegant staircase. Distinctive in design and exceptional in scale, this remarkable property offers ample room to add a pool and create your own private outdoor oasis. Ideally situated near New Seabury Country Club, with memberships available, members can enjoy access to two championship golf courses, full service clubhouse, five restaurants, two beach clubs, fitness facility, sixteen tennis courts and multiple pools. With generous accommodations and exceptional space, this home is ideally suited for those seeking privacy and flexibility for family, children, seniors, caretakers and guests alike. A truly unique offer in one of New Seabury's most desirable settings, where architectural distinction, luxury living, and the beauty of Cape Cod come together. Start creating your own Cape Cod memories for years to come. Please refer to feature sheet under documents for additional highlights.

41 Shore Dr W, Mashpee

Listing courtesy of Listing Agent: Debbie Kenney from Listing Office: .

$4,995,000

4 Beds ⋅ 7 Baths ⋅ 22605242 MLS

A rare offering in New Seabury, this extraordinary custom-built residence overlooks the 18th fairway of the Ocean golf course at New Seabury Country Club, where sweeping golf course views meet refreshing ocean breezes. Designed by William Harris Architects of Atlanta in the genre of renowned architect A.M. Stern, celebrated for his distinguished private residences in the Hamptons and fine resort designs, including Disney's Yacht and Beach Club Resorts at Walt Disney World, this home reflects a distinctive architectural vision and timeless elegance. Offering over 6,000 square feet of luxurious living space, this exceptional residence features four bedroom en-suites, three half baths, and beautiful hardwood floors throughout. Three thoughtfully designed levels of living, along with a full basement, are conveniently accessible by private elevator or elegant staircase. Distinctive in design and exceptional in scale, this remarkable property offers ample room to add a pool and create your own private outdoor oasis. Ideally situated near New Seabury Country Club, with memberships available, members can enjoy access to two championship golf courses, full service clubhouse, five restaurants, two beach clubs, fitness facility, sixteen tennis courts and multiple pools. With generous accommodations and exceptional space, this home is ideally suited for those seeking privacy and flexibility for family, children, seniors, caretakers and guests alike. A truly unique offer in one of New Seabury's most desirable settings, where architectural distinction, luxury living, and the beauty of Cape Cod come together. Start creating your own Cape Cod memories for years to come. Please refer to feature sheet under documents for additional highlights.

41 Shore Drive W., Mashpee

Listing courtesy of Listing Agent: Deb J Kenney (dkenney@robertpaul.com) from Listing Office: Berkshire Hathaway HomeServices Robert Paul Properties.

$4,995,000

6 Beds ⋅ 6 Baths ⋅ 24212918 MLS

Experience the pinnacle of modern luxury at 8 Bouton Lane, a masterful new construction that sets a new benchmark for craftsmanship in Darien. Every inch of this residence reflects an uncompromising commitment to quality, from the soaring nine-foot ceilings on the main level to the intricate millwork and exquisite waist-high paneling that graces the formal dining and living rooms. At the heart of the home, a chef's dream kitchen awaits, equipped with top of the line appliances, centered around an expansive island w/ample seating. The open flow leads seamlessly into inviting spaces anchored by a fireplace in both the living and family rooms, perfect for sophisticated entertaining. The second floor is a sanctuary of comfort, headlined by a sumptuous primary suite. This retreat features a dramatic tray ceiling in primary bath, a private sitting area w/its own gas starter fireplace, dual walk-in closets and floor-to-ceiling wainscoting. The 4 additional spacious bedrooms on this level share two thoughtfully designed Jack&Jill baths. The finished 3rd level, not to be missed, has two rooms with vaulted ceilings, skylights, custom shiplap walls, and a full bath. This flex space can be the 6th bedroom, home office, or any customized use. Not to be outdone, the finished lower level offers nearly 1,000 sq ft featuring a elegant tray ceiling, side paneling, a walk-in cedar closet, and convenient walk-out access. Outside, the large, private bluestone patio provides a serene setting for

8 Bouton Ln, Darien

Listing courtesy of Maggie Marchesi from Compass Connecticut, LLC. (203) 249-1433 (203) 423-3100

$4,995,000

4 Beds ⋅ 5 Baths ⋅ 73581090 MLS

COASTAL LUXURY IN KATAMA — EXCEPTIONAL LIVING NEAR SOUTH BEACH. Set in one of Katama’s most coveted locations, where the sound of the ocean drifts in and South Beach is within easy reach, this distinctive coastal contemporary was thoughtfully designed to maximize natural light, energy efficiency, and long-term flexibility.The reverse-style floor plan places the main gathering spaces on the upper level, where abundant windows fill the interiors with sunlight and frame distant views across the lower reaches of Katama Bay. The open-concept Living, Dining, and Kitchen areas flow seamlessly together, creating an inviting setting for relaxed Vineyard living and effortless entertaining. At the heart of the home, the oversized Chef’s Kitchen opens directly onto a spacious porch for outdoor dining, gathering, and lounging, while two additional porches further extend the living space. The upper porch also enjoys seasonal views of the Edgartown fireworks, and nearby Fisherman’s Wharf and the public boat landing offer convenient access to Katama Bay and Edgartown Harbor.The home features four light-filled en suite bedrooms, each with a private bath and spacious shower. The generous Primary Suite includes dual oversized closets, a walk-in shower, and a private water closet. A bright first-floor bonus room offers flexible use as a Den, In-Home Gym, yoga studio, or additional guest space, with sliding glass doors for privacy, its own porch, and an adjacent half bath.Future accessibility was incorporated into the original design through a fully framed, wired, and mechanically prepared elevator shaft, allowing for the potential installation of an elevator with minimal disruption.Offered turnkey with indoor and outdoor furnishings and an established rental history, 98 Edgartown Bay Road is equally compelling as a personal Vineyard retreat, an income-producing investment, or a combination of both. The property also offers room for a future swimming pool and detached garage, subject to local approvals. Thoughtfully conceived for entertaining, sustainability, accessibility, and lasting enjoyment, this exceptional Katama residence presents a rare opportunity just moments from South Beach.

98 Edgartown Bay Rd, Edgartown

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.

$4,995,000

5 Beds ⋅ 5 Baths ⋅ 5110976 MLS

A truly rare opportunity on Silver Lake, offered together, this exceptional property includes a like-new timber-frame residence and nearly completed neighboring carriage house, offering a combined 212 feet of waterfront on two level lots with a walk-in sandy beach. Built by Blue Water Construction & Development, a Lakes Region custom builder with more than 30 years of experience, the home showcases exceptional craftsmanship, true timber-frame construction, and warm wood details for a timeless lake house feel. Thoughtful design choices, exceptional craftsmanship, and quality finishes are evident throughout the main residence, highlighted by true timber-frame construction and warm wood details. The open-concept kitchen, dining, and living area features wood floors and a striking stone-surround gas fireplace. The oversized kitchen includes dual islands, custom cabinetry, double wall ovens, prep sink, beverage refrigerator, and a large walk-in pantry. An expansive screened porch and glass sliders lead to the outdoor patio and level waterfront beyond. The first-floor primary suite features a soaking tub and walk-in closet, while upstairs offers two spacious bedroom suites and a large loft for additional living or hobby space. A finished bonus room above the garage features vaulted, wood-clad ceilings. Additional amenities include a heated three-car garage with epoxy floors, whole-house generator, composite siding, cobblestone driveway, and beautiful walkways. The neighboring carriage house adds incredible versatility along with an additional 100 feet of Silver Lake frontage. Nearly complete, it features a four-car garage below and full living quarters above with two bedrooms, a full bath, and open living and dining space with views toward Silver Lake. Together, these properties create an exceptional Silver Lake compound with 212 feet of waterfront, seven garage bays, flexible accommodations, and an extraordinary setting for generations of lakefront living.

150-156 Gardners Grove Rd, Belmont

Listing courtesy of Brie Stephens from Compass New England, LLC. ()

$4,995,000

6 Beds ⋅ 8 Baths ⋅ 73579890 MLS

A rare and exceptional six bedroom estate with timeless architectural appeal, Designed by Jan Gleysteen Architects, this custom home showcases unsurpassed craftsmanship, meticulous attention to detail and curated finishes throughout. The first floor welcomes you with the grand foyer's dramatic staircase, a richly appointed mahogany-paneled library, and elegant formal living and dining rooms. The kitchen includes a large island, breakfast room that leads to the family room anchored by a beautiful limestone fireplace and screened in porch. Five en suite bedrooms are highlighted by the expansive primary suite complete with a spa-like bath and generous walk-in closets. The third floor has a sun-filled sitting room with a 6th bedroom. The lower level offers a bonus room with bar, golf simulator room and home gym. Set on one of Weston's most picturesque roads close to trails and major commuting routes to Boston and Cambridge.

448 Concord Road, Weston

Listing courtesy of Listing Agent: Mizner + Montero from Listing Office: Gibson Sotheby's International Realty.

$4,995,000

5 Beds ⋅ 6 Baths ⋅ 22604593 MLS

The ultimate Chatham compound! Set high on a bluff with views of Hardings Beach and Nantucket Sound, this impressive property features a 4,100+ sqft main house, oversized two-car garage with private guest suite above, and a resort-style backyard with an expansive patio and pool. Inside, ten-foot ceilings, custom built-ins, abundant natural light, and generous living spaces set the tone. The grand family room opens directly to the backyard, while the adjacent kitchen offers top-of-the-line appliances, soaring ceilings, outdoor access, and a spacious dining area. A formal dining room, living room, first-floor primary suite, guest bedroom, full bath, powder room, and laundry provide easy one-level living. Upstairs, a second primary suite features a sitting area, walk-in closet, and private deck overlooking Nantucket Sound. Two additional bedrooms, a sitting room, and a full bath complete the second floor. The heated garage is topped by a private guest suite with coffee bar, full bath, and sitting area. Outside, enjoy a deck, patio, fire pit, multiple gathering areas, and large pool. Deeded access to the private neighborhood path to Hardings Beach is less than 1/10 mile away.

65 Harbor View Road, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith (chris.rhinesmith@compass.com) from Listing Office: Compass Massachusetts, LLC.

$4,995,000

5 Beds ⋅ 5 Baths ⋅ 24195094 MLS

1716 Shippan Avenue represents a rare opportunity to own a legacy estate on 1.01 acres in Stamford's sought-after Shippan neighborhood. This distinguished Tudor home is comprised of approximately 6,000 square feet of timeless architectural character, sophisticated modern updates, and a thoughtfully designed 2016 renovation by Granoff Architects. With 5 bedrooms, 3 full and 2 half baths, the home is rich in detail, including original stained glass, oak paneling, unique solid oak arched interior doors, and three wood-burning fireplaces. Custom millwork, a Vermont slate roof, and new Marvin windows throughout further showcase the home's exceptional craftsmanship. The beautifully updated second-floor bathrooms feature custom cabinetry, bookmatched marble showers and countertops, and heated floors. In addition to generous living and entertaining spaces, the home also includes a finished lower level, a third-floor loft with water views (currently used as a home gym), and a charming attached greenhouse. Outside, a 40' x 20' gunite pool and spa, expansive patio, and mature gardenscape create a picturesque private oasis. Exceptionally private, the expansive grounds made up of 2 parcels provide an idyllic backdrop for sun-filled summer days, evenings spent poolside, and memorable gatherings with family and friends. Enjoy Shippan's waterfront community minutes away from the Stamford Yacht Club, local dining, and the express train to Manhattan.

1716 Shippan Ave, Stamford

Listing courtesy of Amanda Spatola from Houlihan Lawrence. (203) 273-8615 (203) 655-8238

$4,995,000

5 Beds ⋅ 7 Baths ⋅ 5105868 MLS

A rare opportunity awaits at this exceptional Dorset Hollow estate, privately situated at the end of exclusive Marcia Lane. Perched high on Dorset Mountain across 16.74 acres, the property captures breathtaking long-range views of Owls Head, Equinox Mountain, and beyond. Built in 2005 by renowned craftspeople, this 7,451-square-foot, five-bedroom, seven-bath estate has undergone a multimillion-dollar renovation, creating an updated, turnkey retreat. Improvements include a new kitchen addition with locally sourced Danby marble and high-end cabinetry, a remodeled primary suite, and comprehensive renovations to the interior, exterior, and grounds. The home offers seamless indoor-outdoor living, flowing onto a wraparound porch and stone patio with an outdoor kitchen. Stone walkways lead to a large lap pool with a diving rock, a ball field, manicured gardens, wildflower meadows, an apple orchard, and an English garden with a fountain and marble bench. Year-round amenities include three wood-burning fireplaces, multiple gathering rooms, a gym, a theater with surround sound and a large wood-burning fireplace, and a hot tub with spectacular views. Speakers serve the first floor, porch, and pool area. The impressive Bensonwood timber-frame barn features an indoor pickleball court and basketball and a full game room. A separate heated equipment barn with power and internet offers space for equipment storage, a woodworking shop, or other uses. Smart-home upgrades include indoor and outdoor lighting controls, thermostats, and a security system with cameras. Wired and wireless internet extends throughout the property, and a full-estate 80 kW generator provides added reliability. Refined finishes include hand-nailed wide-plank pine floors, crown molding, wainscoting, slate, marble, cherry wood, handmade wrought iron, and locally sourced materials. The grand primary suite showcases dramatic Bensonwood timber framing, creating a warm private retreat.

440 Marcia Ln, Dorset

Listing courtesy of David A Halligan from Four Seasons Sotheby's Int'l Realty. ()

$4,995,000

3 Beds ⋅ 4 Baths ⋅ 24194201 MLS

The dream of waterfront living is officially taking shape-construction is underway by renowned builder The O'Dell Group. This is your chance to secure a front-row seat to the Long Island Sound on one of Westport's most prestigious stretches of coastline. This exceptional property offers direct water frontage + sweeping, uninterrupted views of the Sound + the iconic Old Mill Beach. Imagine waking up to the soft glow of a sunrise over the water, spending your afternoons enjoying the refreshing salt air, or relaxing to the rhythm of the tide. Every detail of this build is designed to maximize the connection to the sea, offering a lifestyle defined by beauty + tranquility. Nestled in a welcoming and picturesque community, you'll enjoy access to top-ranked schools + Westport's vibrant downtown, known for its exceptional dining, shopping, and cultural experiences. Plus, the location is ideal for commuters, with close proximity to Metro-North for a seamless trip to Grand Central Station in NYC. As the last available parcel of its kind for development in this coveted location, this project represents a rare opportunity to own a brand-new architectural masterpiece in an idyllic setting. With The O'Dell Group's signature craftsmanship now in motion, the vision for this ultimate beach house is becoming a reality. Seize the opportunity to claim this piece of paradise and personalize your finishing touches while there is still time. Reach out today to make this coastal sanctuary your own.

238 Hillspoint Rd, Westport

Listing courtesy of Karen Scott from Compass Connecticut, LLC. (203) 613-9200 (203) 293-9715

$4,995,000

6 Beds ⋅ 6 Baths ⋅ 73545332 MLS

One of Wellelsey's signature properties! Rarely available 18 room estate w/ 4 floors of living situated in the heart of Peirce Estates. Stunning foyer w/ curved staircase. Sunken living room w/ coffered ceilings & stone fireplace. Oversized dining room w/ bay window plus large butler's pantry. Kitchen w/ stainless appliances, center island & breakfast nook. One of a kind family room filled w/ built-in bookcases, coffered ceiling, fireplace & wet bar perfect for entertaining & everyday living. Wood panel den/office. Main bedroom w/ 2 walk-in closets & fireplace. 3 additional beds & 2 baths. Large sitting room/bonus room w/ fireplace completes 2nd floor. Third floor w/ 2 more beds & bath plus another large bonus room with built-in bunk beds. Lower level w/ playroom, game room & bar room. Over 7700 sq ft with almost one acre of privacy abutting the reservoir. Fieldstone patio. 400 amp service. 3 car garage & steel beam construction. Your chance to own one of Wellesley's most iconic homes!

43 Monadnock Road, Wellesley

Listing courtesy of Listing Agent: Melissa Dailey from Listing Office: Coldwell Banker Realty - Wellesley.

$4,995,000

4 Beds ⋅ 5 Baths ⋅ 73532630 MLS

Wing House Farm is an exceptional 12+ acre estate offering refined pastoral beauty and coastal country living. Abutting the 280+/- acre Destruction Brook Woods, the property enjoys direct access to scenic trails while remaining close to Village shops, marinas, beaches and dining. Rolling lawns, stone walls, split-rail fenced paddocks and established gardens define the picturesque landscape. At the heart of the estate is a meticulously renovated antique Colonial with elegant proportions and timeless charm. Equestrian amenities further distinguish the property, including a barn equipped with 4 box stalls, tack room and guest quarters. Perfectly sited between the barn and the detached 2 bay garage with loft space, an in-ground pool and spa add an inviting layer of leisure. A rare offering where historic character, equestrian amenities and coastal access converge along the South Coast.

111 Slades Corner Road, Dartmouth

Listing courtesy of Listing Agent: Team MCM from Listing Office: Gibson Sotheby's International Realty.

Ask Us About Our Office Listings

Featured Properties

How much is your home worth?

How much is your home worth?