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304 Brookside Rd, Darien
$6,095,000
6 Beds ⋅ 8 Baths ⋅ 24158797 MLS
Architecturally stunning six-bedroom Colonial graces 2.29 level acres designed for resort-style living with pool, pool house, outdoor shower, stone terrace with kitchen & garden masterfully built in 2014. Beautifully appointed 6,117 sq ft interior brimming with exquisite details including high coffered ceilings, transom topped doorways & box molding. Striking double height foyer introduces ideal floor plan, perfect for everyday living & entertaining, anchored by chef's marble-clad kitchen which opens to large family room with fireplace flanked by doors to magnificent screened porch with industrial grade heaters & fireplace. Elegant dining room with fully equipped butler's pantry, stylish living room & office both with fireplaces, mudroom & two powder rooms round out this level. Sumptuous primary suite with fireplace, his/her walk-in closets, deluxe bath with radiant heated floors; two en-suite bedrooms, two bedrooms with Jack/Jill bath, homework area, laundry room comprise 2nd floor. Generous lower-level boasts media room with projector, game room, wine room with wine refrigerator, bedroom, full bath & generator. Unfinished top floor features ample storage & unlimited potential. Outdoor Kalamazoo gourmet kitchen is fitted with grill, pizza oven, smoker & kegerators. Incredible pool house (add'l 860 sq ft) includes custom kitchenette, half bath with outdoor shower & loft. Ideally located on professionally landscaped, private lot with fenced-in yard near all Darien offers.

304 Brookside Rd, Darien

14 Elmwood Avenue, Cambridge
$6,070,000
5 Beds ⋅ 5 Baths ⋅ 73509018 MLS
There are houses one admires, and those that quietly capture the heart. For the current owners of 14 Elmwood Ave, it was a true love affair. Built in 1895, this Queen Anne residence sits on a quiet dead-end street in the historic West Cambridge neighborhood, just off Brattle St. and moments from Harvard Sq. Thoughtfully renovated by a landscape architect & developer/urban planner, it blends historic elegance with modern comfort. High ceilings, beautiful proportions, and leaded glass windows with diamond panes fill the home with light. The layout unfolds with exceptional flow, with a well-designed kitchen opening to a family room and south-facing patio and garden. The corner primary suite is a peaceful retreat with open sky views. 5 bedrooms plus a flexible lower-level suite, 4.5 bathrooms, media room and gym, central a/c, and an attached garage, with add’l pkg in the driveway. Across from the Harvard President’s residence and close to the Charles River, Shady Hill & BB&N schools.

14 Elmwood Avenue, Cambridge

120 Vineyard Road, Barnstable
$6,050,000
6 Beds ⋅ 8 Baths ⋅ 73511490 MLS
Set on the sandy shores of Nantucket Sound, 120 Vineyard Road represents the pinnacle of coastal living with a private sandy beach in one of Cotuit's most sought-after locations. The 5-bedroom residence showcases superlative finishes with beamed ceilings, wainscoting and crown molding throughout. From the grand foyer to the chef's kitchen with breathtaking water views, each space was designed with intention. The fireplaced living room flows to a formal dining room and great room, while a first-floor en suite bedroom offers private guest accommodations. The primary suite is a sanctuary of luxury with a private deck, a lounge, walk-in closet, and a luxurious bathroom. Three additional en-suite bedrooms ensure comfort and convenience. A bluestone terrace provides the perfect backdrop for al fresco entertaining with a short path to the beach. A 3-car garage and a guest cottage complete this exceptional offering. A rare combination of privacy and modern luxury in an unrivaled location!

120 Vineyard Road, Barnstable

59 Sail Harbour Dr, New Fairfield
$6,050,000
6 Beds ⋅ 9 Baths ⋅ 24166572 MLS
An Exceptional Renovated Waterfront Retreat, set majestically on 5.19 private acs. offers 400' of frontage on Candlewood Lake complete w/private dock & sand beach. Enticing outdoor spaces include the heated, in-ground pool w/paving stone patio overlooking the lake, An expansive 20 X 40 deck on main level & a walk-out, lower level to a stone patio w/fire pit; ideal for summer entertaining! Approach the entry through glass doors to the 2 story foyer w/turn stair & modern lighting. French doors on the left, open to the formal dining room w/built ins, custom light fixtures & moldings. An expansive 38 ft great room w/marble fireplace, surrounded by windows exudes a warm, comfortable ambiance. A second stone fireplace warms the family room, ideal for TV viewing, reading or just relaxing. Custom millwork, built-ins, hardwood floors & a plethora of windows, showcase the views from every angle. The Chef's kitchen boasts Wolf appliances, marble countertops, wet bar & stunning center island plus a designer range hood! The enticing primary suite hosts his/her bathrooms, WIC, built-ins & loft w/ views. Three other designer bedrooms offer a Jack & Jill bath & an en-suite. An expansive lower level boasts 15 ft. ceilings, recreation space with stone fireplace, half bath, wet bar, bunk room w/full bath & a 5th en suite bedroom w/full bath. An additional full bath for future movie theater, 3 laundries, 3 car gar. plus SHC amenities:tennis, community beach, clubhouse. A one of a kind lake find!

59 Sail Harbour Dr, New Fairfield

250 Davenport Dr, Stamford
$6,014,250
2 Beds ⋅ 3 Baths ⋅ 24174434 MLS
Set on 1.68 extraordinary acres at the end of Davenport Drive, this waterfront peninsula property offers a rare chance to reimagine and transform an existing residence into a custom coastal estate. Offered for the first time in 76 years, the home is surrounded by water on three sides, providing sweeping 180-degree eastern, southern, and western exposures that fill the interiors with natural light and frame panoramic views from sunrise through sunset. The current residence offers a blank canvas for the next owner to bring their vision to life. Whether through a comprehensive restoration or a complete reconfiguration, the opportunity exists to create a home that fully realizes the potential of this remarkable setting. With a completed survey and feasibility study already in place, much of the initial groundwork has been done. The property also offers the best of both worlds - privacy and seclusion at the end of a quiet road in the Southfield Association and extreme proximity to downtown Stamford and Old Greenwich - granting easy access to restaurants, shopping, beaches, and train service. It's a rare opportunity to reimagine a home that is placed on one of the most special pieces of property in Fairfield County.

250 Davenport Dr, Stamford

63 Rutherford Avenue, Boston
$6,000,033
6 Beds ⋅ 7 Baths ⋅ 73583513 MLS
A rare find in the city, this spectacular 6+BR/5F/2H bath home offers the ultimate combination of interior space, substantial indoor parking - 7 spots total, and private outdoor space on a scale and functionality more often associated with suburban living; with total indoor/outdoor walkable space in excess of 9,000sf. In the 4BR main residence, spanning nearly 5,000sf, a private elevator seamlessly brings you from the garage level with office/family room, to the second-floor primary suite level, including guest bedroom and gym; and up to the third-floor main living level, which also includes two additional en-suite bedrooms, making transport of groceries, luggage, packages, and everyday necessities a breeze. Expansive entertaining areas, both inside and out, include a third-floor grilling/seating area with 2-way gas fireplace, and a sprawling roof deck above w/Italian pizza oven and incredible city views. The second-floor primary suite offers a serene bedroom w/Juliette balcony, luxurious spa bath w/steam shower and floating BainUltra tub; and sought after walk-in custom closet space with generous storage. A gym with two-person infrared sauna is off the guest space. The third floor is the heart of the home. A high-end chef’s kitchen anchors the floor and flows naturally into the principal living and dining areas. Two additional bedrooms and a separate media room are located on this level. A completely separate 2BR auxiliary residence, w/2 car garage, offers income potential, au pair or guest space. This offering is just moments from Charlestown’s historic streets, waterfront, shops, and restaurants, and with the North End and downtown Boston just across the bridge, catching a concert at the TD Garden or cheering on the home teams is close at hand from this home.

63 Rutherford Avenue, Boston

9 Bellevue Road, Wellesley
$6,000,000
6 Beds ⋅ 7 Baths ⋅ 73547652 MLS
Set within Wellesley’s distinguished Cliff Estates, this contemporary residence, completed in 2025, blends scale, refined design, and modern luxury across three finished levels. A grand foyer with floating stair and walls of windows introduces light-filled interiors with generous ceiling heights. Formal living and dining rooms, supported by a Butler’s station, elevate entertaining. The kitchen anchors daily life with an oversized island, premium appliances, and a separate pantry with patio access. A family room, private office, and first-floor en-suite complete the main level. Upstairs, the primary retreat offers a spa-inspired bath and custom walk-in closet, set apart from a lounge and three en-suite bedrooms. The walkout lower level extends the living space with recreation, media, gym, and an en-suite guest room. Two bluestone patios and a landscaped yard bordered by a mature tree line create a private outdoor setting near shops, dining, trails, and Wellesley Country Club.

9 Bellevue Road, Wellesley

250 Long Pond Rd, Great Barrington
$5,995,000
7 Beds ⋅ 8 Baths ⋅ 24166025 MLS
Experience a rare Zen-inspired retreat in the heart of the Berkshires, designed in harmony with its natural surroundings. Set on nearly 120 acres of protected land with striking rock outcroppings, sweeping mountain views, and ~1,000 feet along the Williams River, this architecturally significant Contemporary offers exceptional privacy just minutes from Great Barrington. Designed by Steven Haas, the home blends steel, glass, concrete, and wood, with soaring interiors and Sorpetaler sliding glass walls that open seamlessly to nature. Expansive decks overlook a 25-meter heated saltwater lap pool, hot tub, and fire pit. The open chef's kitchen with oversized wood-burning fireplace anchors the home, while the living room offers a second fireplace and serene views. A glass and stone courtyard enhances the tranquil design. The primary suite is a private sanctuary with spa-like bath, dressing room, office/lounge, and its own deck. Guest accommodations throughout offer comfort and privacy. The lower level includes a billiards room, wet bar, and additional living space. A separate guest house features two bedrooms, kitchenette, living/dining area, and rooftop deck. The 3,000 sq ft recreation barn offers a full kitchen, loft, gym, and flexible gathering space. Eight miles of private trails lead to the Williams River, completing this exceptional retreat just 10 minutes from town.

250 Long Pond Rd, Great Barrington

22 Apple Tree Trl, Westport
$5,995,000
5 Beds ⋅ 5 Baths ⋅ 24158799 MLS
Located on a quiet private lane just two blocks from Compo Beach, this newly built coastal residence at 22 Appletree Trail offers a rare combination of modern craftsmanship, thoughtful design, and effortless beach living in the heart of Westport. Spanning approximately 4,791 sq ft of living space, the home blends timeless architectural elements with refined contemporary finishes. White oak floors, soaring ceilings, and custom Italian cabinetry create a warm and sophisticated interior. The chef's kitchen features L'Ottocento cabinetry, Thermador appliances, and Compac Quartz surfaces, complemented by a fully equipped butler's pantry with a second dishwasher and wine refrigeration. An open-concept family room with a sleek linear gas fireplace flows seamlessly to the covered outdoor terrace overlooking the heated pool and landscaped grounds-perfect for both quiet evenings and entertaining. Upstairs, vaulted bedrooms include fully furnished custom closets. A sun-filled lounge opens to a private rooftop deck with a gas fireplace and seasonal views of Long Island Sound. The primary suite offers a private terrace, dual walk-in closets with custom Italian millwork, and a spa-inspired bath designed for relaxation. Set moments from the shoreline while offering easy access to Manhattan via train, this newly completed residence presents a rare opportunity to enjoy modern coastal living in one of Westport's most desirable neighborhoods.

22 Apple Tree Trl, Westport

33 Commonwealth Ave Unit 5, Boston
$5,950,000
3 Beds ⋅ 3 Baths ⋅ 73573905 MLS
Set on the sunny side of the coveted second block of Commonwealth Avenue, this 3,109 SF residence offers single-level living with direct elevator access and sweeping views over the Comm Ave Mall. Soaring ceilings, elegant moldings, oversized windows, and custom built-ins showcase the home's rich architectural detail, beautifully preserved throughout. The flexible floor plan includes two bedrooms plus a den that doubles as an office, family room, or third bedroom. The primary suite features two full bathrooms — one with a concealed dressing room — along with abundant closet space and custom built-ins. Two private balconies, one deeded garage space and one deeded outdoor parking round out this rare offering. Moments from the Public Garden, Newbury Street, and the Charles River Esplanade, this is a rare opportunity to own a floor-through residence in one of Back Bay's most sought-after settings.

33 Commonwealth Ave Unit 5, Boston

164 Stanwich Rd, Greenwich
$5,950,000
5 Beds ⋅ 6 Baths ⋅ 24159056 MLS
Welcome to this exquisitely updated Colonial on 1.16 landscaped acres near Greenwich Country Club and minutes from town. A grand foyer with gleaming hardwood floors and sweeping staircase introduces the elegant interior. The main level includes a formal living room, dining room, two studies, and a gourmet kitchen with Wolf appliances, Palissandro marble, Thermador coffee station, a custom wet bar and a 425-bottle wine cellar. The kitchen opens to a family room with fireplace and French doors. Upstairs, the primary suite offers a sitting room, luxurious bath, office, and fireplace. Four additional bedrooms complete the level. Enjoy 3,000+ sq ft of terrace, heated saltwater pool, Viking grill, and a pavilion with sound system. The Heated and air conditioned 4-car garage adds storage and versatility.

164 Stanwich Rd, Greenwich

143 Oenoke Rdg, New Canaan
$5,900,000
5 Beds ⋅ 8 Baths ⋅ 24135729 MLS
Experience the pinnacle of sophisticated living in this extraordinary estate by renowned builder Kaali-Nagy, perfectly situated within walking distance to the village, train, and nature center. The residence showcases impeccable craftsmanship throughout, defined by extensive custom moldings, intricate wainscoting, and an effortless flow designed for both grand entertaining and intimate daily life. At the heart of the home, a gourmet chef's kitchen features a sun-drenched breakfast room and a butler's pantry, with French doors opening to one of three private terraces for seamless indoor-outdoor transitions. Designed to elevate everyday living, the home also boasts a fully equipped private home gym, an inviting billiards room and media area, perfect for relaxed gatherings.The private property is equally impressive, boasting a spectacular 20 x 40 heated gunite pool surrounded by professionally designed, mature landscaping that creates a serene and secluded outdoor retreat-ideal for summer entertaining or peaceful relaxation. This thoughtfully designed floor plan includes five spacious ensuite bedrooms, each boasting its own walk-in closet, ensuring unparalleled comfort for family and guests alike. Complete with the modern convenience of a private elevator serving the home's multiple levels, this property offers a rare blend of timeless architectural detail, exceptional amenities, and a premier "walk-to-everything" location.

143 Oenoke Rdg, New Canaan

1 Bramble Ln, Greenwich
$5,900,000
5 Beds ⋅ 7 Baths ⋅ 24157206 MLS
Exceptional custom built 5 bedroom stone and shingle home in a sought-after Riverside location. Across from Riverside school/playground and one block to Eastern Middle School, this beautifully designed and professionally decorated home showcases a two-story foyer, well proportioned and light-filled living spaces, high ceilings, exceptional finishes and craftsmanship. Spacious chef's kitchen has stainless steel appliances and opens to a lovely family room w/fireplace. Seamless access to the stone patio and outside kitchen overlooks the new Shoreline pool and level private yard. Elegant primary suite plus 4 generous sized bedrooms upstairs. The expansive lower level has a large recreation area, gym and bonus room with bath. Extras: 6 fireplaces, 3 car garage, covered front porch. Turnkey!

1 Bramble Ln, Greenwich

56 Cart Path Rd, Weston
$5,890,000
6 Beds ⋅ 10 Baths ⋅ 73478929 MLS
Exquisite cape colonial estate in Weston’s golf club area. Perfect location on 2.85 acres in Weston's top neighborhood. Two floor grand foyer opens to the coffered great room, drenched in light from the floor to ceiling windows and the patio doors, which open out to the massive deck overlooking the large, flat, private back yard, while the grand fireplace and custom millwork impress. Large chef’s kitchen features huge central island, professional appliances, and custom cabinetry. The adjoining informal dining features skylights and wall to wall windows overlooking the back yard. The first also features the grand formal dining room with cathedral ceiling and a large open family room with fireplace and sitting area. Bedrooms maximize flexibility, including two amazing master suite options on the 1st & 2nd floor, while the 3rd floor has the in-law suite as well as a game room. The lower level boasts a theater, wine cellar, and gym. A+ location within 18 minutes to Boston.

56 Cart Path Rd, Weston

96 E Elm St Unit 1, Greenwich
$5,850,000
4 Beds ⋅ 4 Baths ⋅ 24204408 MLS ⋅ Arbor Rose BLDG.
This is the one you've been waiting for. Set within the gated Arbor Rose Association, this beautifully renovated condo pairs a serene, manicured setting with effortless access to Greenwich Avenue. Step inside the inviting interior with 10-foot ceilings and an elevator, where natural light moves through the open living and dining rooms into a custom kitchen and welcoming family room with fireplace. The spacious primary suite offers a spa bath, extra large walk-in closet, coffee bar, and flows to an office or sitting room with a private balcony. Two additional bedrooms and laundry room complete the upstairs. The finished lower level provides a second family room, flexibility for a fourth bedroom or gym, and a full bath. Outside, private landscaped spaces with room for a BBQ create a peaceful setting for morning coffee or evenings at home, while the nearby train allows for a seamless commute to New York City.

96 E Elm St Unit 1, Greenwich

8 Bowsprit Pt, Mashpee
$5,850,000
4 Beds ⋅ 5 Baths ⋅ 73559069 MLS
Welcome to one of New Seabury's most extraordinary waterfront offerings. Perfectly positioned on a private, oversized lot, 8 Bowsprit Point delivers the ultimate Cape Cod lifestyle with a coveted 50-foot, shore-powered deep-water dock offering direct access to Nantucket Sound. Whether you're setting out for a day on the water or returning for sunset cocktails, boating has never been more effortless. Designed for exceptional indoor-outdoor living, the expansive grounds showcase a heated gunite pool, spa, generous entertaining patios, and sprawling lawn surrounded by mature landscaping for remarkable privacy. Inside, more than 6,000 square feet have been thoughtfully reimagined with a spacious, open layout that captures panoramic water views through soaring walls of glass, creating an elegant yet comfortable retreat for everyday living and grand entertaining alike. Nestled on one of New Seabury's most desirable streets, this is a rare opportunity to own a legacy waterfront estate where luxury, privacy, recreation, and location come together in one unforgettable property. Opportunities like this are exceptionally rare--experience coastal living at its finest.

8 Bowsprit Pt, Mashpee

252 River Rd, Deep River
$5,850,000
5 Beds ⋅ 7 Baths ⋅ 24143703 MLS
A WORLD-CLASS PRIVATE ESTATE SET ON 9.31 GATED ACRES. Nestled behind a private gated entry, this extraordinary CT River Valley estate is a rare luxury compound of architectural distinction, solitude, & resort-caliber amenities. Thoughtfully composed across 5 distinct structures, the property blends modern luxury, European influences, & timeless craftsmanship amid curated landscapes, stone pathways, terraces, & over 6,000sf of refined outdoor living space. This is a truly exceptional, once-in-a-lifetime offering. A long winding driveway gradually reveals an exclusive enclave where the outside world fades away. Stucco structures, cedar shake roofs, & copper gutters emerge in sequence, unified by professionally landscaped grounds, irrigation, & exterior lighting that enhances the estate's serene atmosphere. Completely rebuilt in 2012, & finished in 2015, the Main Residence is a masterclass in quality & livability. Rich millwork, custom cabinetry, radiant-heated hardwood floors, transom windows, & skylights define interiors that feel both elegant & inviting. A boutique-style coat room & jewel-box powder room immediately signal the home's uncompromising level of finish. The show-stopping kitchen features high-gloss bespoke cabinetry, nickel hardware, & a sculptural range hood beneath tall silver-leaf detailed ceilings. A substantial Calacatta marble island integrates a 2nd sink, butcher block, & concealed storage. Chef-grade appliances include SubZero, Wolf, & Miele. *CONTINUED*

252 River Rd, Deep River

140 Stoneleigh Rd, New Canaan
$5,800,000
6 Beds ⋅ 10 Baths ⋅ 24167662 MLS
Discover the epitome of timeless luxury in this magnificent Colonial Chateau-style residence. Perfectly situated on two flat, meticulously landscaped acres in a coveted walking neighborhood, this home offers unparalleled privacy while remaining just moments from town and top-rated schools. This quiet, no-cut-through street is a haven for outdoor enthusiasts, offering exceptional bike riding and walking routes right from your door. The active neighborhood association fosters a true sense of community-think spirited trick-or-treating, seasonal gatherings, and friendly faces at every turn. Enjoy the best of both worlds: peaceful residential living with convenient access to prime roadways for an easy commute. The interior is a masterful blend of elegance and comfort, featuring six spacious en suite bedrooms and an astounding eight indoor fireplaces that create warmth and ambiance throughout. Designed for grand entertaining and modern family living, the home boasts multiple family rooms, ensuring ample space for every occasion. Indulge your passions in the dedicated wine cellar and the custom-designed sports den. The sophisticated primary level flows seamlessly to the breathtaking exterior amenities, which include a built-in pool for summer relaxation and a beautiful outdoor fireplace for year-round enjoyment. Completing this exceptional estate are four spacious garage bays, providing abundant storage and convenience.

140 Stoneleigh Rd, New Canaan

9 Pond Edge Rd, Westport
$5,775,000
6 Beds ⋅ 7 Baths ⋅ 24143533 MLS
Experience the pinnacle of Compo Beach living at 9 Pond Edge Road, a rare coastal sanctuary offering immediate beach access with the peace of mind of an elevated, flood-safe setting. Spanning 6,100 square feet across four impeccably finished levels, this 6-bedroom home is designed for effortless entertaining and everyday relaxation. Sunlight fills the open great room (with WBF) and dining area, where a wall of French doors opens to a private backyard oasis featuring a heated gunite pool, stone patio, and built-in BBQ, all surrounded by mature landscaping. A cozy living room with a gas fireplace provides the perfect setting for intimate gatherings or quiet evenings at home. At the heart of the home is the eat-in Chef's Kitchen, complete with luxury appliances, two dishwashers, three ovens, and an oversized center island. A flexible main-level suite offers ideal space for an executive office or guest accommodations. The second floor showcases a serene primary suite with a gas fireplace, dual dressing rooms, and a spa-inspired bath, along with three additional en-suite bedrooms and a laundry room. The third level features a secluded guest suite with private balcony and a skylight-filled bath. The lower level is a destination of its own, offering a home theater, dedicated gym, recreation room, and full bath with direct access to the pool. Complete with a whole-home generator and attached garage, this turn-key property delivers laid-back luxury just moments from the sand.

9 Pond Edge Rd, Westport

124 Chestnut Hill Rd, Newton
$5,750,000
5 Beds ⋅ 8 Baths ⋅ 73527607 MLS
Set along one of Chestnut Hill’s most coveted private roads, this stately brick home offers a serene oasis with sweeping views of the Chestnut Hill Reservoir. Gut-renovated in 2021, the home blends timeless architecture with modern luxury across over 7,000 square feet of impeccably finished living space. The main level features a chef’s kitchen, elegant living and dining spaces, a refined study overlooking the patio, a powder room, and two mudrooms. Upstairs, the primary suite offers dual dressing rooms and a spa-like bath, along with four additional en-suite bedrooms and a flexible office/play area. The third floor includes a home gym and bonus room, while the lower level provides flexible living space, laundry, and two full baths. Set on 0.61 acres with a large patio and 2-car garage, this is a truly exceptional offering for those seeking a premier location, refined design, and timeless appeal.

124 Chestnut Hill Rd, Newton

22 Liberty Dr Unit 11C, Boston
$5,700,000
3 Beds ⋅ 3 Baths ⋅ 73529521 MLS
Ten-foot ceilings amplify every sight line. Two private balconies put you in the view, not just near it. There is no better vantage point in the Seaport. Full stop. Inside, the design is as deliberate as the location. The open floor plan moves from a custom built-in living room to a dining area with panoramic harbor views that open onto the first balcony — effortless, elegant, and built for the way you actually live. The kitchen doesn’t ask you to compromise: Wolf range, Miele, Sub-Zero, wine chiller, waterfall island, High-gloss white lacquer cabinetry, quartz countertops and a picture window framing the water. The kitchen was designed to impress. The primary suite commands its own spectacular water view with a second private balcony, two walk in closets, marble bath with soaking tub, glass shower and double vanity. The second en-suit bedroom carries the same water views. Nothing was left as an afterthought. 2 car garage and fitness center. Homes like this are rare opportunities.

22 Liberty Dr Unit 11C, Boston

6 Twin Circle Dr, Westport
$5,700,000
6 Beds ⋅ 7 Baths ⋅ 24168601 MLS
Nestled on a quiet cul-de-sac in one of Westport's most convenient locations, 6 Twin Circle Drive offers luxury living with exceptional indoor and outdoor spaces. Just moments to Bedford Middle School, Staples High School, downtown Westport, trains, shopping, restaurants, Longshore, and Compo Beach, this property combines privacy, recreation, and convenience. The resort-style backyard features a pool with spa, expansive lounging areas, full outdoor kitchen, and a rare post-tension concrete tennis court - the premier surface used at elite clubs and college facilities. A truly extraordinary amenity rarely found in residential homes. The home offers an open floor plan filled with natural light and thoughtfully designed spaces. The gourmet chef's kitchen features high-end appliances, abundant workspace, and two dishwashers. Main-level highlights include elegant entertaining spaces, a private meditation room, and seamless indoor-outdoor flow. The primary suite is a retreat with a spa-inspired bath, steam shower, and dressing room with abundant closets. Upstairs, an incredible playroom with six built-in beds creates the perfect sleepover space or playroom. The walk-out lower level offers versatility with a media room, gym, office, and guest suite ideal for extended family, au pair, or guests. Rarely does a Westport luxury home offer resort-style amenities, premier tennis facilities, flexible living space, and walk-to-school convenience in such a private setting.

6 Twin Circle Dr, Westport

757 Oenoke Rdg, New Canaan
$5,700,000
7 Beds ⋅ 8 Baths ⋅ 24147831 MLS
The "Legacy Estate" An Oenoke Ridge Masterpiece: The main brick residence captures the essence of Gilded Age elegance with 10-12 ft ceilings, eight fireplaces, a classic wrap-around-porch, and a porte-cochere. Spanning four finished levels, the main residence seamlessly blends original character with a significant three-story addition completed in 2012. The newer wing features a spacious Smallbone gourmet kitchen, sun-drenched breakfast room, large working pantry, 2-sided fireplace, large center island fit for a master chef and an adjacent family room all designed for casual living and effortless entertaining. The main residence includes a luxurious owner suite with fireplace, balcony, marble bath and 2 walk-in-closets. There are six additional bedrooms on the upper levels. The home is rich with architectural character throughout. The property also includes: - Three Historic Barns: Versatile spaces for collectors, animal lovers, gardeners or car enthusiasts. Grounds: Set high on the ridge, 4 pastoral acres with an identified pool site, multiple gardens, and rolling lawns. Own a piece of New Canaan history on Oenoke Ridge.

757 Oenoke Rdg, New Canaan

25 Kenilworth Road, Wellesley
$5,696,375
6 Beds ⋅ 7 Baths ⋅ 73530280 MLS
Welcome to 25 Kenilworth Road, a distinctive residence in Wellesley’s coveted Dana Hall neighborhood, blending classic architectural detail with sophisticated modern living. Thoughtfully designed with exceptional craftsmanship, this home offers gracious living spaces with desirable amenities.The spectacular chef’s kitchen features dual islands, custom cabinetry, premium appliances, and box-beam ceilings, easily opening to a stunning fireplaced family room. Elegant formal living and dining rooms, & a well-appointed study, create ideal spaces.Spacious mudroom connects to a heated garage. Upstairs, a luxurious primary suite with spa-like bath and custom closets, 4 add’l bedrooms, 3 full baths, and laundry. The third-floor includes a bedroom, w/ media room and a finished lower level with recreational space & fitness room completes this incredible home. All is further enhanced by beautiful outdoor grounds w/bluestone patio, fire pit, built-in grill, and sports court! All boxes are checked!

25 Kenilworth Road, Wellesley

316 Beacon St Unit Penthouse, Boston
$5,684,000
3 Beds ⋅ 3 Baths ⋅ 73552178 MLS
Crowning one of Back Bay’s most prestigious addresses, this extraordinary three-bedroom penthouse represents a rare offering of exceptional distinction and enduring elegance. Privately accessed via direct elevator entry, the residence is defined by grand proportions, impeccable craftsmanship, and an unparalleled connection to the outdoors. Three magnificent terraces, encompassing approximately 1,824 square feet, command breathtaking panoramic views of the Charles River and the Boston skyline, offering an extraordinary setting for both sophisticated entertaining and private enjoyment. Two deeded garage parking spaces complete this remarkable offering. Ideally positioned at 316 Beacon Street, moments from the Charles River Esplanade, Newbury Street, and Boston’s most celebrated cultural, dining, and shopping destinations, this is an exceptional opportunity to acquire one of Back Bay’s most distinguished penthouse residences.

316 Beacon St Unit Penthouse, Boston

188 Brookline Ave Unit PH29A, Boston
$5,650,000
3 Beds ⋅ 3 Baths ⋅ 73377535 MLS ⋅ ['Pierce Boston Private Residences'] BLDG.
Soar above the city in this custom 3BR, 3BA Corner Penthouse Sanctuary at Pierce Boston by globally renown Arquitectonica, w/UNOBSTRUCTED 270° panoramic views of the Harbor Islands, Charles River&Emerald Necklace. Situated between Back Bay&Brookline, this home incl. 100SF Balcony&2 Deeded Self-Park Garage Spaces in Boston’s premier Ultra Luxury 5 Star Address. Grand Cove Lit Foyer&Custom Entry opens to a dramatic TRIPLE-EXPOSURE Great Room w/soaring 16’3” ceilings&wall-to-wall glass. Chef’s kitchen ft. Wolf, Sub-Zero&Miele apps incl. built-in espresso, wine fridge&externally vented hood. Retreat to the corner primary suite w/11'x11' dressing RM&5 Piece Spa Bath w/stunning views. 2 Add’l BRs, Custom Millwork, Lighting&Motorized Shades complete the home. Enjoy 20,000SF curated amenities:Sky Lounges, Heated Pool&Spa Tub, Library, Pet Spa, Fitness, 24/7 Concierge, Porter&more. Surrounded by World Class institutions, dining, green space, steps to Pru/Newbury. Cabana Avail for Upgrade.

188 Brookline Ave Unit PH29A, Boston

316 Mansfield Ave, Darien
$5,625,000
5 Beds ⋅ 7 Baths ⋅ 24167771 MLS
Just in time for summer-this exceptional property offers the ultimate in luxury living and outdoor enjoyment. Imagine relaxing poolside by your new heated pool and spa, surrounded by beautifully landscaped grounds and sweeping views of the golf course. Inside, the home is equally impressive. The expansive primary suite is a true retreat, featuring a private sitting room that opens onto a deck overlooking the pool-perfect for morning coffee or evening unwinding. The suite also boasts a beautifully updated bath and two spacious walk-in closets. The second level is thoughtfully designed with four additional en-suite bedrooms and a versatile playroom, offering comfort and privacy for family and guests alike. At the heart of the home is a stunning new gourmet kitchen, outfitted with top-of-the-line appliances including a Wolf range, two Sub-Zero refrigerators, a separate freezer, and three dishwashers-an entertainer's dream. The lower level is equally striking, featuring an elite gym, a playroom, and abundant open space for recreation and play-perfect for entertaining, relaxing, or staying active without ever leaving home. This remarkable colonial seamlessly blends elegance, comfort, and modern convenience-perfect for making unforgettable summer memories and beyond.

316 Mansfield Ave, Darien

975 Memorial Drive Unit 201/202, Cambridge
$5,600,000
1 Beds ⋅ 3 Baths ⋅ 73495552 MLS ⋅ ['The Residences At Charles Square'] BLDG.
Renovated top to bottom with impeccable taste and the highest quality of materials, this stunning unit showcases fine features throughout such as floor-to-ceiling windows overlooking the river, custom millwork, Sonos surround sound, and a comfortable climate with central air conditioning & home humidification. The dreamy primary suite provides dual bathrooms, and a fully outfitted dressing room. Accompanying the living and dining rooms is a library with a balcony, and tranquil office. The striking kitchen opens to a 2nd balcony. There's also a 20' gym and additional full bath. The Residences at the Charles is a luxury full-service building with easy access to the Harvard Kennedy School, JFK Memorial Park, Harvard Business school, as well as fine dining & shopping. Enjoy elegant common areas, curated gardens, and a premier vantage point for the Head of the Charles Regatta. Residents enjoy peace of mind with 24/7 front desk support, a fire suppression system, and elevators.

975 Memorial Drive Unit 201/202, Cambridge

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