Feature Properties

Set off a lovely cul-de-sac, this restored Greek Revival sits on 4+ acres of open field, rare this close to Boston, stretching out rather than closing in. The expansive field: open, level, and bordering the 7,000 acre Blue Hills Reservation, accessible and yours to explore. A buildable lot: room to expand, a family compound, simply hold as open space, you decide. Fine millwork and French doors speak to fine craftsmanship. The kitchen is anchored by top appliances and built for serious cooking. A well-appointed mudroom keeps the everyday beautifully managed. A glass-walled garden room with fireplace, woodland views and stillness. Modern systems (geothermal heating/cooling, solar array, EV charger) reflect a commitment to sustainability. Privacy and peace without sacrificing reach: commuter rail, Rts 128/95, and Logan Airport all close. Access to Milton's public and the area's prestigious independent schools. This is where sophistication, sanctuary, and the wide-open sky meet.

1632 Canton Ave, Milton

Listing courtesy of Listing Agent: Julianne Bridgeman from Listing Office: Ceres Real Estate.

$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

3 Beds ⋅ 4 Baths ⋅ 73536923 MLS

Truly incredible offering! This elegant property with 17(!) windows on the parlor level alone, offers a private townhouse-style entrance on picturesque Spruce Street, grand spaces and 3+ bedrooms. The rooms welcome you upon entry with their allure and volume. Guests will be in awe of the expansive living and dining spaces w/ 12 foot ceilings - unique, rarely seen architecture and scale. Beautiful millwork, a gas fireplace & warm hardwood flooring all add to this graceful space. Standout features include a handsome library/home office w/ wood paneled walls-a distinguished setting. A wonderfully laid out, oversized kitchen w/ notable appliances and pantry is adjacent to a fantastic den allowing for casual dining & cozy entertaining options. A luxurious primary suite w/ seating area offers 2 walk-in closets and an opulent bathroom. Two addt'l large bedrooms w/ en suite baths, powder room, storage. Reference floorplan to view the exceptional layout of this spacious, one-of-a-kind property.

50 Beacon Street Unit 50, Boston

Listing courtesy of Listing Agent: Rebecca Davis Tulman and Leslie Singleton Adam from Listing Office: Gibson Sotheby's International Realty.

$4,995,000

3 Beds ⋅ 2 Baths ⋅ 73531359 MLS

Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking fireplace with a glacial stone hearth, while the open kitchen offers custom cabinetry and premium appliances. The primary suite includes two office spaces, a media area, walk-in closet, and spa-inspired bath. A private guest suite features a full bath with soaking tub, and the third bedroom is currently configured as a wellness space with sauna. Additional amenities include an attached two-car garage, owned solar panels, EV charging station, and a six-bedroom septic system.Seven Gates Farm residents enjoy access to private beaches, docks, tennis courts, and more.1000 acres of protected land.

35 South Bowl Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..

$4,995,000

4 Beds ⋅ 4 Baths ⋅ 73529657 MLS

Perched on the waterfront in Chatham's coveted Stage Island neighborhood, this exceptional 4-bedroom, 4-bath coastal retreat offers 270-degree panoramic views of Stage Harbor, Nantucket Sound, and surrounding tidal marshes. Built to stringent post-Katrina standards and completed in 2011, the home showcases superior construction, reinforced structural tie-downs, and impact-rated windows. Designed to maximize its breathtaking setting, the light-filled open floor plan features walls of glass and stunning water views from nearly every room. The main level includes a spacious living room with fireplace, dining area, updated kitchen, two bedrooms, and a shared bath. Upstairs, two private en-suite bedrooms enjoy elevated harbor vistas. The walkout lower level offers a family room and fitness space overlooking the water. A 2025 kitchen renovation, 2019 revetment, direct water access for kayaking, paddleboarding, fishing, clamming, and swimming, make this an exceptional opportunity.

56 Stage Island Road, Chatham

Listing courtesy of Listing Agent: James Lowenstern from Listing Office: eXp Realty LLC.

$4,995,000

4 Beds ⋅ 6 Baths ⋅ 73529545 MLS

Few homes in Cohasset capture the ocean, Minot’s Light and Little Harbor and with such extraordinary breadth. Extensively renovated with exceptional finishes, this four-bedroom residence offers sweeping water views from nearly every principal room, a custom library/study, four full and two half baths, and a spectacular roof deck with panoramic vistas. The sophisticated coastal design flows beautifully throughout the home, while recent improvements include new systems, Azek decking, landscaping and masonry. Ideally located near Cohasset Village, Sandy and Black Rock beaches, and the commuter rail, this exceptional property offers a rare combination of expansive water views, refined interiors and convenient access to Boston.

3 Jerusalem Lane, Cohasset

Listing courtesy of Listing Agent: Greta Gustafson from Listing Office: LandVest, Inc..

$4,995,000

10 Beds ⋅ 11 Baths ⋅ 73523970 MLS

The Aldrich House returns to Red Brook Harbor. Built in 1890 as a seaside retreat for Boston travelers arriving by train, the Cataumet landmark was fully restored in 2022 with all-new systems, whole-house generator, and an 18-bedroom Title V septic, the kind of permit Cape towns no longer issue. Across three stories, more than 7,000 SF of refined interior: an open great room with floor-to-ceiling stone fireplace, a chef's kitchen, original hardwood restored throughout, and wraparound porches that hold the harbor view. 10 en-suite bedrooms, each with private sitting room, kitchenette, independent climate control, and a balcony for Buzzards Bay sunsets. Outside, 1.84 manicured acres with in-ground pool, gazebo, and firepit. The home includes 3X Commercial Speed Queen dashers and dryers, and more. Family compound, private retreat, or boutique hospitality. Minutes from sandy beaches, Red Brook walking trails, the National Seashore, and the Islands ferries; and only 80 minutes from Boston.

48 Red Brook Harbor Rd, Bourne

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

$4,995,000

8 Beds ⋅ 8 Baths ⋅ 5089015 MLS

Set in one of Stowe’s most sought-after locations, Eden is a remarkable 22± acre mountain estate offering privacy, recreation, and breathtaking natural beauty. Surrounded by lush landscapes with views of Mount Mansfield and the Worcester Range, the property features beautifully maintained gardens, twin ponds, a tennis court, heated pool, and two hot tubs, creating an exceptional setting for both relaxation and entertaining. The residence offers eight bedrooms and eight baths with soaring vaulted ceilings and thoughtfully designed living spaces throughout. Just minutes from Stowe Mountain Resort, the property also enjoys direct access to Wiessner Woods for hiking, snowshoeing, and cross-country skiing. Paired with close proximity to some of Stowe’s best dining and amenities, Eden presents a rare opportunity to experience elevated Vermont mountain living in an extraordinary setting.

740 Edson Hill Rd, Stowe

Listing courtesy of The Nancy Jenkins Team from Nancy Jenkins Real Estate. ()

$4,995,000

4 Beds ⋅ 5 Baths ⋅ 24172306 MLS

A spectacular waterfront residence on Masons Island, 39 Chippechaug Trail captures the very best of coastal New England living. Set on 2.05 private acres with more than 250 feet of direct waterfront, this custom-built, move-in ready 4,300 square-foot home enjoys sweeping 180-degree water views, a private sandy beach, deep-water access and its own dock all within one of the Mystic/Stonington area's most coveted waterfront settings. Beautifully maintained and thoughtfully positioned to embrace its extraordinary surroundings, the residence offers comfortable, inviting interiors designed to be enjoyed from day one. Expansive windows and water-facing spaces create a natural connection between the home, grounds and shoreline, while mature oaks frame the property with exceptional privacy and an established coastal landscape. Designed for both relaxed everyday living and entertaining, the property transitions effortlessly from the house to expansive lawns, beach and dock. Boating, swimming, kayaking and days on the water begin right outside your door, while the breadth of the property creates a remarkable sense of openness, privacy and connection to the shoreline. A three-car garage and geothermal heating add comfort and functionality, while the private island setting feels worlds away yet remains just minutes from downtown Mystic's acclaimed restaurants, boutiques, marinas and waterfront attractions.

39 Chippechaug Trl, Stonington

Listing courtesy of Danielle Malloy from Serhant Connecticut, LLC. (203) 921-9987 (203) 489-7800

$4,995,000

5 Beds ⋅ 8 Baths ⋅ 73503213 MLS

Reimagined & redesigned stunning custom home on over 1 acre in Weston's prestigious Golf Club neighborhood. New layout, new floors, new custom built-ins, new kitchen, new butler pantry, new bathrooms, new moudings, white oak door trim, new furnaces, new AC condensers, new Marvin windows, new stone walls & landscaping...... Kitchen family room w/ breakfast nook opens to large family room w/ fireplace. Spacious living room/dining room ideal for entertaining. Private office off of grand foyer. Bedroom & en suite bath on first floor. Main bedroom w/ large custom closet & gorgeous spa-like bath. 3 additional bedrooms all w/ large closets & en suite baths. Front & back staircase. 2 mudrooms. Lower level w/ full bath, playroom, media room plus exercise. This home has huge Marvin windows creating a sunfilled home. Overlooking majestic Skating Pond & its rustic lodge designed by Fredrick Law Olmstead in 1909. Close distance to Weston Town Center and routes to Boston. A must see!

9 Skating Pond Road, Weston

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

$4,995,000

6 Beds ⋅ 8 Baths ⋅ 73492806 MLS

The Ultimate Newton Location 1/2 block from Waban Square! Have you been dreaming of working with a respected local design firm to realize your vision of a contemporary home equipped with a chef's kitchen? If you need an expansive home office on a separate level with privacy, comfort and a safe distance from the refrigerator this house has it! This charming village home is a modern masterpiece designed for discerning taste. Top rated schools, convenient public transit and strategic location near all major roadways make this the ideal option for your new home! The builder has their own model home custom build studio, and they will build this house to your exact specifications...but you need to act quickly before the work begins. Expect occupancy in the Summer of 2026.

151 Pine Ridge Road, Newton

Listing courtesy of Listing Agent: James Lowenstern from Listing Office: eXp Realty LLC.

$4,995,000

5 Beds ⋅ 7 Baths ⋅ 24126503 MLS

Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community, an exclusive four-lot enclave envisioned and built by Joe Feinleib, founder of Coastal Luxury Homes and one of Fairfield County's most respected builders.This private neighborhood blends timeless architecture with modern luxury. Each custom residence, ranging from 5,000 to 7,500 square feet, plus generous garages, balconies, patios and covered porches, will be designed in collaboration with the homeowner - ensuring every detail reflects your vision. Expansive layouts, pool sites, and inviting outdoor living spaces create the perfect setting for today's lifestyle, balancing sophistication with everyday comforts. Working with Coastal Luxury Homes is a dynamic, collaborative and easeful process with every detail curated to suit the homeowners' vision of the perfect home. Whether you dream of having your own golf simulator, outdoor chef's kitchen, sauna or elevator...everything is possible. Ideally located just moments from Westport's award-winning schools, vibrant downtown, the train, and Compo Beach, this unique neighborhood offers a rare combination of privacy and convenience. Mature landscaping and thoughtful design create a serene retreat, while the best of dining, shopping, and recreation are just minutes away. This is more than a new home - it's the chance to create your dream residence with an award-winning builder in a community unlike any other in Westport.

1 Coastal Ct, Westport

Listing courtesy of Julie Vanderblue from Higgins Group Real Estate. (203) 257-6994 (203) 254-9000

$4,995,000

9 Beds ⋅ 10 Baths ⋅ 5063499 MLS

Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed bedrooms, five fireplaces, original wood and marble floors, and handsome moldings throughout. The home has been thoughtfully expanded to include a sun-filled country kitchen with custom cabinetry, formal and informal dining rooms, a library, family room, and multiple living spaces that open to marble terraces and gardens. Enhancing the estate are extraordinary amenities, including a marble in-ground swimming pool with stone terrace, a tennis court, and a one-bedroom caretaker’s cottage with attached garage for on-site management or guest overflow. A 2,400 square foot three-bedroom guest house, created from the original c.1796 post-and-beam barn, blends historic charm with modern comfort. A goat and chicken barn, equipment barn, and a separate 30’ x 60’ seven-bay toy and car barn provide abundant storage and the opportunity for a true Vermont farmstead lifestyle or a spectacular car collection. The grounds are equally captivating, featuring mature landscaping, open meadows, orchards, perennial gardens, and stone walls. Pergolas, walkways, and extensive marble terraces.

1182 1184 East Manchester Rd, Manchester

Listing courtesy of Betsy Wadsworth from Four Seasons Sotheby's Int'l Realty. ()

$4,995,000

3 Beds ⋅ 1 Baths ⋅ 73343859 MLS

Development opportunity in a PRIME Newton Upper Falls location. This is a 41,102 sq ft MR1 / Multi residentially zoned lot with a single family home.

66 Rockland Place, Newton

Listing courtesy of Listing Agent: Alison Haran from Listing Office: Coldwell Banker Realty - Newton.

$4,990,000

5 Beds ⋅ 9 Baths ⋅ 73498185 MLS

Privately set at the end of a quiet cul-de-sac and DIRECTLY ABUTTING ESTABROOK WOODS, this exceptional Concord estate sits on 3.5 acres of breathtaking landscaped level land. With over 12,500 sq ft, the home offers refined architectural details, custom millwork, marble accents and beautifully scaled rooms for both grand entertaining and comfortable daily living. The dramatic great room features soaring 21-ft arched ceilings and a striking stone fireplace. Elegant living and dining rooms, a richly appointed library and a chef’s kitchen with top-tier appliances anchor the main level. A luxurious FIRST FLOOR PRIMARY SUITE offers a spa-inspired marble bath and French doors opening to the bluestone patio and grounds. Outdoor living includes an expansive terrace with outdoor cooking overlooking the sparkling POOL. Finished lower level with large finished rooms and private au pair apartment. A rare opportunity to enjoy estate-scale living with direct access to ESTABROOK WOODS!

215 Monument Farm Rd, Concord

Listing courtesy of Listing Agent: Senkler, Pasley & Whitney from Listing Office: Coldwell Banker Realty - Concord.

$4,980,000

5 Beds ⋅ 5 Baths ⋅ 73574731 MLS

From the moment you arrive, you’ll fall in love with this much-admired white brick Colonial, beautifully sited on a charming corner in Wellesley’s coveted Cliff Estates. Set back from the road and surrounded by beautifully landscaped grounds, this exceptional home offers the perfect blend of elegance, comfort, and space for today’s lifestyle. Inside, gracious rooms unfold with everything exactly where you want it—and more than you expect. The inviting fireplaced living room opens to a light-filled sunroom, ideal as a home office or quiet retreat, with French doors leading to the stone patio. The state-of-the-art kitchen features generous stone countertops, new ovens and Sub-Zero refrigeration, a charming dining area with banquette seating, and an exceptional walk-in pantry. A gracious dining room with a window seat and custom built-ins is perfect for entertaining.The oversized family room, with its dramatic barrel ceiling, abundant windows, and doors opening to the yard, is sure to become the heart of the home. An additional study provides yet another flexible space for working from home or relaxing. A glamorous turned staircase leads to the second floor and a stunning primary suite featuring two walk-in closets and a luxurious marble spa bath. Three additional bedrooms and two full baths, including one en-suite, complete this level. The finished lower level offers even more versatile living space with a playroom, exercise area, additional bedroom, and full bath. Oversized three-car garage with added storage space is such a plus! Outside, enjoy professionally landscaped grounds with mature trees and beautiful plantings. Exceptionally maintained and beautifully decorated throughout, this elegant Cliff Estates home offers a rare combination of timeless style, generous living space, and effortless everyday comfort.

97 Arnold Road, Wellesley

Listing courtesy of Listing Agent: Bobby Morgenstern from Listing Office: Gibson Sotheby's International Realty.

$4,975,000

4 Beds ⋅ 6 Baths ⋅ 5077621 MLS

Prime Stowe Hollow location outdone only by it’s spectacular views of the Green Mountains. Panorama’s sweeping vantage of Mt. Mansfield and the valleys below will take your breath away. With a private, top-of-a-hill setting, mere minutes from Stowe Village, this 16+ acre estate features a 7900+/- sf classic Shingle Style architectural gem. The meticulously maintained 4 bedroom, 6 bath home is light-filled with mountain views from nearly every room. With three floors of living space, Panorama was designed for entertaining friends and family. Unwind after a day of hiking, mountain biking or skiing by one of the three fireplaces or head out to the vast, wrap-around deck to take in incredible Green Mountain sunsets. An expansive bonus room makes for an ideal home office or additional activity/gathering space. The impeccable grounds include flowering shrubs, perennial gardens, a wildflower meadow, and a large, professionally built fire pit with generous space for outdoor gatherings in any season. Miles of trails into the protected CC Putnam State Forest and the Worcester Range are easily accessible, while a short walk from the back door leads to Gold Brook for a quick dip in the numerous swimming holes. Panorama is centered in the heart of Stowe Hollow just under 10 miles to Stowe Mountain Resort, 3.8 miles to Stowe village, 15 minutes from Stowe-Morrisville airport, 35 minutes to Burlington Airport, 2.5 hours to Montreal and a 3-hour drive to Boston. No drive-bys.

675 Putnam Forest Rd, Stowe

Listing courtesy of Meg Kauffman from LandVest, Inc.. ()

$4,950,000

6 Beds ⋅ 6 Baths ⋅ 73575312 MLS

Rare quarter-acre retreat in the heart of Brookline Village, this fully renovated Victorian offers 5,487 square feet of exceptional living space, a large private backyard, and the character of a historic home paired with modern luxury. Completely renovated to the studs in 2025, the six-bedroom, six-bath residence is just steps from the shops, restaurants, and Green Line in Brookline Village, minutes from Longwood, and only three miles from downtown Boston. Inside, soaring ceilings, white oak hardwood floors, and extensive custom millwork, cabinetry, built-ins, and vanities create a timeless, sophisticated interior. The chef’s kitchen features high-end appliances, including a paneled Sub-Zero refrigerator and 36-inch Wolf convection range, complemented by a butler’s pantry, dedicated coffee bar, and additional under-counter wine refrigerator. Designed for both everyday living and entertaining, the home offers expansive living, dining, and family spaces, four fireplaces, radiant heated floors, two laundry rooms, and an impressive full-height lower level. A private wellness retreat includes a dedicated gym, cedar sauna, and steam shower, while a wet bar with a full-height Sub-Zero wine refrigerator and adjoining recreation space provides an additional setting for entertaining. Two oversized decks, an outdoor gas fireplace, and hot tub extend the living space outdoors and overlook the expansive, fully fenced backyard. Behind the historic exterior, the residence has been comprehensively modernized with new-construction-level infrastructure, including all-new electrical, plumbing, and mechanical systems and five-zone central heating and cooling. A rare opportunity to enjoy substantial private outdoor space, beautifully preserved Victorian character, and the comforts of a complete modern renovation in one of Brookline’s most desirable and convenient locations. See more at 220Aspinwall.com

220 Aspinwall Ave, Brookline

Listing courtesy of Listing Agent: Christopher Roy from Listing Office: Gibson Sotheby's International Realty.

$4,950,000

3 Beds ⋅ 4 Baths ⋅ 73570275 MLS

Situated along the peaceful shores of the Oyster Pond River, this stunning seaside home effortlessly blends classic New England architecture with modern luxury. Arriving along a gravel driveway bordered by blooming hydrangeas and mature trees, the residence makes an immediate impression with crisp white columns and a bluestone walkway. Inside, light-filled interiors showcase clean architectural lines, light wood floors, and custom built-ins. At the heart of the home lies a soaring vaulted great room anchored by a large stone fireplace, framed by double-height windows and glass French doors that capture panoramic water views.Designed for effortless entertaining and everyday comfort, the main level flows between open gathering areas and quiet retreats. The eat-in chef's kitchen features custom cabinetry and professional-grade appliances, including a Sub-Zero refrigerator, double ovens, and a Thermador range. Adjoining the kitchen, the formal dining room serves as a centerpiece for hosting, complete with built-in display shelving and a cozy window seat, illuminated by a custom glass pendant light fixture suspended from a recessed ceiling. A first-floor en suite bedroom completes the main level, providing refined accommodations for guests or family. On the second level, a light-filled den is equipped with a wet bar, a built-in alcove day bed, and a private balcony overlooking the water. The primary suite serves as a true sanctuary, complete with vaulted ceilings, expansive windows framing water views, and a contemporary fireplace. The spa-like primary bath boasts a deep soaking tub with a wood surround, a glass shower with textured wall tiling, dual-sink vanities with under-cabinet lighting, and connects to a spacious walk-in closet. The lower level offers endless possibilities with a stone fireplace, built-in workstations, additional guest space, and a fully appointed bath with a deep soaking tub. Outside, multi-tiered outdoor spaces - including covered decking, a stone patio, and manicured lawns running down toward the water's edge - offer front-row seats to Chatham's iconic maritime landscape. Whether setting off by kayak for a day on the water or enjoying al fresco entertaining amidst unsurpassed natural beauty, this property represents coastal Cape Cod living at its absolute finest.

103 Aunt Nabby's Lane, Chatham

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

$4,950,000

3 Beds ⋅ 4 Baths ⋅ 22604310 MLS

Situated along the peaceful shores of the Oyster Pond River, this stunning seaside home effortlessly blends classic New England architecture with modern luxury. Arriving along a gravel driveway bordered by blooming hydrangeas and mature trees, the residence makes an immediate impression with crisp white columns and a bluestone walkway. Inside, light-filled interiors showcase clean architectural lines, light wood floors, and custom built-ins. At the heart of the home lies a soaring vaulted great room anchored by a large stone fireplace, framed by double-height windows and glass French doors that capture panoramic water views. Designed for effortless entertaining and everyday comfort, the main level flows between open gathering areas and quiet retreats. The eat-in chef's kitchen features custom cabinetry and professional-grade appliances, including a Sub-Zero refrigerator, double ovens, and a Thermador range. Adjoining the kitchen, the formal dining room serves as a centerpiece for hosting, complete with built-in display shelving and a cozy window seat, illuminated by a custom glass pendant light fixture suspended from a recessed ceiling. A first-floor en suite bedroom completes the main level, providing refined accommodations for guests or family. On the second level, a light-filled den is equipped with a wet bar, a built-in alcove day bed, and a private balcony overlooking the water. The primary suite serves as a true sanctuary, complete with vaulted ceilings, expansive windows framing water views, and a contemporary fireplace. The spa-like primary bath boasts a deep soaking tub with a wood surround, a glass shower with textured wall tiling, dual-sink vanities with under-cabinet lighting, and connects to a spacious walk-in closet. The lower level offers endless possibilities with a stone fireplace, built-in workstations, additional guest space, and a fully appointed bath with a deep soaking tub. Outside, multi-tiered outdoor spaces - including covered decking, a stone patio, and manicured lawns running down toward the water's edge - offer front-row seats to Chatham's iconic maritime landscape. Whether setting off by kayak for a day on the water or enjoying al fresco entertaining amidst unsurpassed natural beauty, this property represents coastal Cape Cod living at its absolute finest.

103 Aunt Nabby's Lane, Chatham

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

$4,950,000

5 Beds ⋅ 8 Baths ⋅ 73556306 MLS

Representing the pinnacle of coastal elegance, this extraordinary estate on Little Island offers a rare opportunity for a generational compound in mint condition and an unsurpassed location. Finished to the highest standards, the property features a spectacular five-bedroom main residence, a swimming pool, a pool house with kitchenette and full bath, and a detached three-car garage with a home gym above. In the main residence, timeless and sophisticated design is on display throughout, with custom millwork, designer wallpaper, soaring vaulted ceilings, and a smart home system that governs doors, locks, and hardware with effortless ease. Superlative craftsmanship and finishes define every room, from the chef's kitchen with professional grade appliances to the exquisitely appointed first-floor primary suite featuring custom-designed closets and a luxurious bathroom with a jetted Grohe shower system. Four additional bedrooms, including a second-floor primary suite, ensure refined accommodations for family and guests, while a finished lower level provides flexible bonus space. Set amidst park-like grounds with manicured landscaping, the backyard features multiple gathering spaces, including an expansive poolside terrace with a summer kitchen and fire pit. The stunning pool house caters to resort-style living and offers endless possibilities. Meticulously appointed with no detail overlooked, additional highlights include a whole-home generator, state-of-the-art security, and Lutron smart lighting. Minutes from everything Osterville has to offer, this exceptional family compound is ready to be enjoyed.

313 Bridge Street, Barnstable

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

$4,950,000

5 Beds ⋅ 8 Baths ⋅ 22603652 MLS

Representing the pinnacle of coastal elegance, this extraordinary estate on Little Island offers a rare opportunity for a generational compound in mint condition and an unsurpassed location. Finished to the highest standards, the property features a spectacular five-bedroom main residence, a swimming pool, a pool house with kitchenette and full bath, and a detached three-car garage with a home gym above. In the main residence, timeless and sophisticated design is on display throughout, with custom millwork, designer wallpaper, soaring vaulted ceilings, and a smart home system that governs doors, locks, and hardware with effortless ease. Superlative craftsmanship and finishes define every room, from the chef's kitchen with professional grade appliances to the exquisitely appointed first-floor primary suite featuring custom-designed closets and a luxurious bathroom with a jetted Grohe shower system. Four additional bedrooms, including a second-floor primary suite, ensure refined accommodations for family and guests, while a finished lower level provides flexible bonus space. Set amidst park-like grounds with manicured landscaping, the backyard features multiple gathering spaces, including an expansive poolside terrace with a summer kitchen and fire pit. The stunning pool house caters to resort-style living and offers endless possibilities. Meticulously appointed with no detail overlooked, additional highlights include a whole-home generator, state-of-the-art security, and Lutron smart lighting. Minutes from everything Osterville has to offer, this exceptional family compound is ready to be enjoyed.

313 Bridge Street, Osterville

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

$4,950,000

5 Beds ⋅ 4 Baths ⋅ 22602292 MLS

Introducing a refined contemporary Chilmark beach house with water views and deeded access to Stonewall Beach on the Atlantic Ocean. The property is set within the storied Stonewall Road and Beach Association - where homes are held for generations and lifelong friendships take root - and offers a true sense of place and continuity. Built by South Mountain Company and thoughtfully renovated and significantly expanded in 2023, the home blends craftsmanship with modern comfort. Enjoy sweeping views of the Atlantic Ocean, Squibnocket Point, and Nomans Land island from both interior living spaces and outdoor vantage points. Designed for multigenerational living, the home offers multiple private zones - including a dedicated media room - allowing for both connection and retreat. This is a rare opportunity to own a meaningful piece of Chilmark--an offering not to be missed.

61 Stonewall Road, Chilmark

Listing courtesy of Listing Agent: Mark D Jenkins (mark@wallacemv.com) from Listing Office: Wallace & Co. Sotheby's International Realty.

$4,950,000

5 Beds ⋅ 6 Baths ⋅ 22602249 MLS

Set on more than 30 acres along Cape Cod Bay, Sunset Farm is a rare coastal compound of remarkable privacy and natural beauty. Thoughtfully created by a master arborist over decades, this legacy property unfolds as a curated landscape of specimen trees, open meadows, winding trails, and five large naturally recharging freshwater ponds. A custom farmhouse, substantial barn, and separate two-bedroom guest house create an extraordinary setting for a year-round multi-generational family compound, or a restorative weekend and summer escape. With direct beach ownership and an atmosphere of complete seclusion, Sunset Farm feels far removed from the everyday, yet located just 50 miles from downtown Boston. Timeless, serene, and impossible to replicate, this is one of Cape Cod's most magical properties and is a pleasure to show, by appointment. First and last photos have been virtually enhanced to illustrate conceptual designs.

46 Roos Road, East Sandwich

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

$4,950,000

4 Beds ⋅ 5 Baths ⋅ 22602178 MLS

Nestled in an elevated position overlooking Chatham Seaside Links, this architectural masterpiece embodies classic coastal elegance and is turn key, furnished and ready for summer! Just a stone's throw to Chatham's pristine beaches and the Village's renowned restaurants, the residence offers a private oasis. It is framed by masterful stonework, open-air living spaces, and artisanal native plantings--setting a captivating tone before you even step inside. The foyer sets the stage for the exceptional design that unfolds within. Built by Steven Nickerson, meticulous millwork, custom Kochman Reidt+Haigh cabinetry accentuating many spaces, and intricate architectural details are found throughout the home. The house boasts an extraordinary level of artistry and craftmanship. The main living room with fireplace is refined yet comfortable and flows seamlessly into an intimate sitting area, partitioned by a custom-built cabinet containing a motorized TV lift, creating multi-use spaces. Smart home technology enhances both functionality and ambiance throughout.

15 Bay Lane, Chatham

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

$4,950,000

6 Beds ⋅ 7 Baths ⋅ 24173339 MLS

Hidden behind Shorehaven Country Club in a gated waterfront enclave, 3 Canfield Crossing offers the rare opportunity to enjoy WATERFRONT LIVING in a NATURALLY PROTECTED WATERFRONT SETTING. Thoughtfully reimagined and extensively updated, the property combines timeless coastal design with the peace of mind of significant recent improvements, including a BRAND NEW CEDAR ROOF, new windows, several new mechanical systems, a new pool heater, and an entirely new chef's kitchen with custom cabinetry and premium appliances. Designed to embrace its waterfront setting, nearly every room captures views of the ever-changing tides. A NanaWall opens the newly renovated kitchen and living areas directly to the expansive waterfront terrace and infinity-edge pool, creating an effortless connection between indoors and out. With four finished levels connected by elevator, six ensuite bedrooms, including two separate guest or au pair opportunities, the home offers exceptional flexibility for everyday living and entertaining. Kayak or paddle board directly from your backyard, spend an afternoon at nearby Shorehaven Country Club, or enjoy the restaurants and amenities of Westport, Rowayton, and South Norwalk just minutes away. Private, protected, extensively updated, and directly on the water, 3 Canfield Crossing delivers a distinctive Fairfield County waterfront lifestyle without sacrificing the comfort, space, and convenience of a substantial year-round residence.

3 Canfield Xing, Norwalk

Listing courtesy of Carly Woodard from William Pitt Sotheby's Int'l. (917) 575-3416 (203) 227-1246

$4,950,000

5 Beds ⋅ 6 Baths ⋅ 73520009 MLS

Set on more than 30 acres along the shores of Cape Cod Bay, Sunset Farm is a rare coastal compound of remarkable privacy and unlimited potential. Thoughtfully created by a master arborist with great vision and care, this legacy property features a curated landscape of specimen trees, open meadows, and winding trails around 5 large and naturally recharging freshwater ponds. A custom built farmhouse, substantial barn, and a separate two-bedroom guest cottage provide for immediate enjoyment, while conceptual plans exist for a full multi-generational family compound including stables, additional guest houses, pool and tennis court. With direct beach ownership and an atmosphere of complete seclusion, Sunset Farm feels far removed from the everyday, yet located within proximity to restaurants, shops and galleries. Timeless, serene, and impossible to replicate, this is one of Cape Cod’s most magical properties and is a pleasure to show, by appointment only.

46 Roos Road, Sandwich

Listing courtesy of Listing Agent: Brian Dougherty from Listing Office: Corcoran Property Advisors.

$4,950,000

4 Beds ⋅ 5 Baths ⋅ 73518596 MLS

Nestled in an elevated position overlooking Chatham Seaside Links, this architectural masterpiece embodies classic coastal elegance and is turn key, furnished and ready for summer! Just a stone's throw to Chatham's pristine beaches and the Village's renowned restaurants, the residence offers a private oasis. It is framed by masterful stonework, open-air living spaces, and artisanal native plantings--setting a captivating tone before you even step inside. The foyer sets the stage for the exceptional design that unfolds within. Built by Steven Nickerson, meticulous millwork, custom Kochman Reidt+Haigh cabinetry accentuating many spaces, and intricate architectural details are found throughout the home. The house boasts an extraordinary level of artistry and craftmanship. The main living room with fireplace is refined yet comfortable and flows seamlessly into an intimate sitting area, partitioned by a custom-built cabinet containing a motorized TV lift, creating multi-use spaces.

15 Bay Lane, Chatham

Listing courtesy of Listing Agent: Chris Rhinesmith from Listing Office: Compass.

$4,950,000

5 Beds ⋅ 6 Baths ⋅ 73486306 MLS

Construction is about to begin on this exceptional home in a private setting—an increasingly rare opportunity to own a residence designed by an internationally recognized, award-winning architect. The vision blends the timeless beauty of traditional architecture with the comfort and functionality of modern living. This respected local development team is known for investing in top architects, designers, and craftsmanship, producing homes in the area that are widely admired. Thoughtful design and attention to detail set this home apart from typical new construction in Newton. Highlights include dramatic floor-to-ceiling windows opening to an expansive deck overlooking the backyard, a chef’s kitchen flowing into a spacious family room, and a luxurious primary suite with three additional bedrooms on the 2nd floor. The lower level has a fantastic recreation room with walk-out access to the yard. There is still time to personalize finishes or add custom touches to make it your forever home

Claremont Street, Newton

Listing courtesy of Listing Agent: Chamberlain Group from Listing Office: Coldwell Banker Realty - Brookline.

$4,950,000

5 Beds ⋅ 8 Baths ⋅ 73474595 MLS

The lifestyle of your dreams awaits in this one-of-a-kind, New England shingle-style home, expertly crafted to meet the demands of modern living and set close to the town center with secluded outdoor spaces and a wildflower meadow. Whether hosting a grand soiree or an intimate family gathering, this home will elevate your entertaining endeavors. The stunning chef’s kitchen has slate counters, large breakfast bar island, informal dining, high end appliances, and seamless flow to the informal dining area and spectacular family room beyond. The backyard evokes the enchanting charm of a secret garden, perfect for entertaining with a wraparound stone porch, patio, and outdoor kitchen. Work from home in the private library or unwind in the billiard room. The luxurious primary suite has a huge walk-in closet, private balcony, fireplace and spa bathroom with a huge marble shower and jacuzzi tub. Third level teen/au pair suite and lower level with second family room, craft room, gym, and sauna.

197 Grant St, Lexington

Listing courtesy of Listing Agent: Danielle Fleming from Listing Office: MA Properties.

$4,900,000

6 Beds ⋅ 6 Baths ⋅ 5091162 MLS

Have you been dreaming of lakefront living? Welcome to 74 Keewaydin Road in Wolfeboro, on Lake Winnipesaukee! This property has over 5 acres of land that sit on the shores of Winter Harbor in Wolfeboro, one of the premier areas of the lake! The harbor is perfect for paddle boarding, kayaking, or rowing as well as water skiing, wake boarding or just swimming too. The southwest exposure allows for sun all day and absolutely beautiful sunsets. With a winding driveway thru the woods, there is plenty of privacy as you approach the home. The waterfront boasts a sandy beach and a U-shaped covered dock with a storage shed. The home has plenty of room for everyone plus all the friends and guests! Sitting close to the water, there are endless views from just about every room in the house plus the outdoor space! There are 6 bedrooms with 5 baths. There is a full living space on the first floor with a fireplaced living room, primary suite bedroom, second bedroom, office, kitchen and screened porch as well as an outside deck to enjoy all the waterfront activities! The full second floor has four bedrooms, three baths, second kitchen, living room with woodstove and deck. The lower level is daylight with plenty of storage space for all the toys! This is the perfect place to spend long summer days watching the loons swim. Come and see what lake living is really all about!

74 Keewaydin Rd, Wolfeboro

Listing courtesy of Cindy Melanson from Melanson Real Estate. ()

$4,900,000

5 Beds ⋅ 7 Baths ⋅ 73511215 MLS

This impressive new construction home ideally located on Sunset Rock Road offers 5 bedrooms, 5 en-suite baths, and 2 half baths. Designed for both luxury and functionality, it features two primary suites, including a private retreat accessed via a sunlit glass-link hallway. Spanning 7,811 sqft, the home showcases a custom kitchen with Wolf and Sub-Zero appliances, Calacatta Monalisa quartz countertops, a walk-in pantry, and seamless flow to the main living areas. Two fireplaces add warmth and architectural appeal, while dual laundry rooms provide convenience. The finished lower level is ideal for entertaining with a theater and wet bar, plus additional unfinished space for a gym or customization. Set on a premier lot, the outdoor space is perfect for relaxation or entertaining. Elevated, private and far from cookie-cutter. This home offers striking curb appeal, with final landscaping set to take it completely over the top.

99 Sunset Rock Rd, Andover

Listing courtesy of Listing Agent: Brette L'Italien from Listing Office: William Raveis R.E. & Home Services.

$4,895,000

6 Beds ⋅ 10 Baths ⋅ 5108870 MLS

A rare offering where New England charm meets modern luxury. Dating to 1835, this exceptional Cape has been thoughtfully renovated, preserving its architectural character while delivering comfort, technology, and craftsmanship. Beyond the visible finishes, extensive infrastructure has been upgraded, including electrical, plumbing, heating, septic and whole house Wi-Fi. A private courtyard introduces the main residence and an extraordinary chef’s kitchen appointed with an Italian granite island, prep sink, refrigerated drawers, Miele 6-burner range with griddle, dual-energy microwave/convection oven, Miele hood, and pot filler. The kitchen flows into the historic “keeping” room, creating a warm gathering space and continues to a sunlit living room with formal dining area. A screened porch and Bluestone patio extend the living space outdoors. The first-floor primary suite is a serene retreat featuring a fireplace, ensuite bath with soaking tub for two, double vanity and shower, private laundry, and a distinctive walk-in closet incorporating the original center chimney. Three additional bedrooms, each with ensuite bath, occupy the second floor. A three-story barn is connected to the main house and offers flexible living/entertaining spaces. Highlights include a family room with kitchenette, bath, laundry, sunroom overlooking stone walls and woods, bedroom, office, additional baths, and an open entertaining level with bar/buffet. Oversized barn doors open to the kitchen courtyard, creating an exceptional indoor-outdoor setting for entertaining. The carriage house offers versatility and privacy, with its own driveway and entrance, full kitchen, living room, office, 1/2 bath, private deck and grill area, plus an upstairs bedroom, ¾ bath, and laundry. A property that honors its history while embracing the best of contemporary living. This is a truly distinctive New England residence designed for both intimate everyday living and grand-scale entertaining.

153 Atlantic Ave, North Hampton

Listing courtesy of Marie Drake from Coldwell Banker Realty - Portsmouth, NH. (Off: 603-334-1900)

$4,895,000

4 Beds ⋅ 6 Baths ⋅ 5096164 MLS

Along a quieter section of Lake Champlain, where the water feels protected and the setting is defined by peace and privacy, this property offers an exceptional lakefront experience. The landscaped grounds include mature trees, perennial gardens, a small apple orchard, expansive stonework, bluestone patios, irrigated lawns and gardens, and a lighted walkway to the water. A private dock with boat lift, Floe dock system, and deep-water mooring make the lake part of daily life. Custom-built by Red House Building with Blue Sky Architects and completed in 2016, the residence was extensively renovated in 2024 and offers approximately 6,500 square feet of living space. The main living areas are open, comfortable, and lake-oriented, with a living room centered around a contemporary gas fireplace with custom concrete mantle, a dining area with lake views, and a well-appointed kitchen with Cabico cabinetry, quartzite island, soapstone counters and backsplash, premium appliances, pantry, and wet bar. A screened porch, lakeside hot tub, and stone patio off the kitchen create inviting spaces for gathering, dining, and enjoying lake views. The first-floor primary suite opens directly to a private stone patio and is complemented by an additional main-level bedroom suite and ensuite den. The second floor includes another bedroom suite, bunk room with custom built-in beds, and workspace with built-in cabinetry, while the lower level adds a recreation room, home theater with surround sound, pool table area, playroom, and storage. A separate 1,120± square foot carriage house provides guest accommodations with lake and garden views, living room, galley kitchen, full bath, finished living space, stone patio, and radiant-heated two-car garage. Together, the main residence, carriage house, grounds, dock, and lake access create an extraordinary Lake Champlain property, designed for year-round comfort and entertaining, just 30 minutes from Burlington.

29 Sweeney Farm Rd, South Hero

Listing courtesy of Wade Weathers from LandVest, Inc-Burlington. ()

$4,895,000

7 Beds ⋅ 7 Baths ⋅ 73376559 MLS

Much admired 7 bedroom, 7000+sf estate home on an acre of manicured lawns on famed Cliff Road. Built and re designed by two of New England’s most acclaimed architects, this home boasts the grandeur of stately proportions and sumptuous millwork with a newly renovated and superbly equipped chef’s Kitchen and butler’s pantry with adjacent family room. A banquet sized dining room and gracious living room both with fireplaces and french doors lead to the private grounds with stone walls, built in grill and multiple sitting areas. Handsome mahogany study with fireplace, ensuite bedroom with newly renovated bath plus a separate sun room complete the 1st floor. Up a curved staircase befitting the most prestigious of homes you will find 6 bedrooms and 4 full baths including the primary suite with, luxurious bath and laundry. Lower level with recreation room and state of the art wine cellar, 3 car heated garage, heated driveway and whole house generator. A once in a lifetime opportunity!

200 Cliff Rd, Wellesley

Listing courtesy of Listing Agent: Donahue Maley and Burns Team from Listing Office: Compass.

$4,880,000

7 Beds ⋅ 11 Baths ⋅ 73500670 MLS

Welcome to 22 Lincoln Rd, a magnificent luxury estate, completely renovated in 2023, nestled on over 3 pristine private acres, where refined elegance meets everyday comfort in perfect harmony. Thoughtfully designed across 3 fully finished levels, the residence showcases rich hardwood flooring, multiple fireplaces, curated lighting, & a sophisticated layout enhanced by 2 staircases. The gourmet chef's kitchen is a culinary masterpiece, outfitted with premium Thermador appliances including a 6 burner range, an oversized refrigerator, microwave, dual dishwashers, and two sinks. A chic wet bar & dedicated coffee bar elevate every dining occasion. With 7 spacious bedrooms, eight luxurious full bathrooms, and three half baths, this home offers remarkable versatility for any lifestyle. A separate suite complete independence with its OWN KITCHEN, living space, bedroom, & full bath. Outside, two expansive decks, an alfresco fireplace, and a potential sports court that awaits your final design.

22 Lincoln Rd, Lincoln

Listing courtesy of Listing Agent: The Lucci Witte Team from Listing Office: William Raveis R.E. & Home Services.

$4,850,000

5 Beds ⋅ 6 Baths ⋅ 5105346 MLS

SERENA LODGE is a one-of-a-kind private mountain estate where timeless architecture, natural beauty, and the Vermont lifestyle come together to create an extraordinary legacy retreat. Inspired by Rockefeller's famed Adirondack Great Camp, The Point, this nearly 9,000-square-foot residence is nestled on over two acres overlooking a crystal-clear brook, with the gentle sound of cascading waterfalls flowing year-round. Serena Lodge combines the privacy and scale of a standalone mountain estate with the convenience of being part of the established Hawk Mountain Resort community. Through the association, owners benefit from road maintenance, snow removal, emergency services, and property management, making ownership easier and more turnkey, particularly for those enjoying Serena Lodge as a second home. Perfectly positioned for four-season recreation, Serena Lodge is approximately 20 minutes from both Killington and Okemo Resorts, about 30 minutes from the quintessential New England village of Woodstock, and just minutes from championship golf, pristine lakes for swimming, kayaking, scenic trails and fishing. Designed by Daniel Pratt of Robert Carl Williams Architects as a multigenerational retreat, Serena Lodge offers six en-suite bedrooms, including a private primary wing with fireplace, sitting room, and balcony. The spectacular Great Hall forms the heart of the home, with soaring timber beams, a monumental stone fireplace, walls of windows that fill the home with natural light and an open kitchen created for effortless entertaining. Beyond the Great Hall, a loft studio, expansive Adirondack room, family room, workshop, and multiple living spaces provide abundant room for family and friends to relax, connect and enjoy the home in comfort and privacy.

476 Salt Ash Rd, Plymouth

Listing courtesy of Debra Staniscia from Four Seasons Sotheby's Int'l Realty. (debra.staniscia@fourseasonssir.com)

$4,850,000

4 Beds ⋅ 5 Baths ⋅ 22501583 MLS

Sunshine Daydream - recently completed and ready to go. Located on a quiet street in desirable 'Sconset village, this newly constructed Cape-style cottage has been thoughtfully expanded and fully renovated. Designed with an efficient use of space and the island lifestyle in mind, the four bedroom home with oversized garage and studio suite is ideal for coastal living and checks all the boxes. The flexible layout offers various options for entertaining and a potential fifth bedroom for guests. Enjoy outdoor living with a large private yard, inviting front porch, wrap around deck and heated Plunge pool all surrounded by native landscaping and custom hardscape. Finished in 2026 and being offered turnkey furnished. Ownership member is a licensed real estate agent in Massachusetts.

8 Sconset Avenue, Siasconset

Listing courtesy of Listing Agent: Paul N Drepanos (paul.drepanos@compass.com) from Listing Office: Compass Massachusetts, LLC.

$4,850,000

4 Beds ⋅ 5 Baths ⋅ 24176398 MLS

"Hollow Farm" - An Expansive Historic Estate Reimagined for Modern Country Living Nestled in its own private valley, this 72-acre estate includes a Main House, thoughtfully updated and expanded in 2005; a charming Guest Bungalow; screened Gazebo perched over a pond; Pool Pavilion; Stables with caretaker's apartment; and a restored Barn. Comprised of multiple parcels, offering maximum privacy. The circa-1755 Main House features a dramatic great room with stone fireplace, adjoining chef's kitchen, and formal dining room. Additional main-level spaces include both a sitting room and a library with back-to-back fireplaces, plus a guest suite with full bath and sitting room. Upstairs, the primary suite offers a lofted sitting area with fireplace, as well as private deck, while two guest bedrooms share a hall bath. The lower level includes a wine cellar with cobbled floor and a gym. Outside, multi-level terraces showcase exceptional stonework, a fire pit, grilling area, pool, and spa. Two ponds and the sparkling Merryall Brook enhance the 18 acres of open land. Extensive landscaping compliments the natural beauty of the forested hills. As with the Main House, every outbuilding and outdoor space has been meticulously maintained. Although it feels a world away, this remarkable property is only 15 minutes from Kent, New Preston, and Washington. With its historic character, modern updates and expansive private setting Hollow Farm offers a rare opportunity for refined country living

57 Indian Trail Rd, New Milford

Listing courtesy of Elyse Harney Morris from Elyse Harney Real Estate. (860) 318-5126 (860) 435-0120

$4,850,000

5 Beds ⋅ 5 Baths ⋅ 24172211 MLS

Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate where classic Arts & Crafts architecture meets the tranquility of a private countryside retreat. Set on over 2.5+ sprawling acres of pristine grounds, this exceptional 5 Bed, 5 Bath residence offers more than 5,100 sqft of refined living, surrounded by natural beauty & complete privacy. From the moment you arrive down the private, meandering drive framed by mature landscaping; The Winslow Manor evokes a sense of warmth, character, and enduring craftsmanship. Rich architectural details, beamed ceilings, inviting living spaces, & thoughtfully designed interiors create a home that feels both grand and deeply welcoming- as if stepping into a piece of cozy history, carefully preserved and elevated for modern living. Designed for both relaxation & recreation, the estate unfolds into an extraordinary outdoor experience. A sparkling Gunite pool, multiple terraces, Pergolas, & dedicated home gym create the ultimate summer retreat, while the surrounding pond and protected wetlands attract an abundance of wildlife, offering peaceful views and a connection to nature rarely found so close town.

22 Evergreen Ave, Westport

Listing courtesy of Valerie Alvarez from Serhant Connecticut, LLC. (203) 224-0361 (203) 489-7800

$4,850,000

13 Beds ⋅ 14 Baths ⋅ 73496031 MLS

The Kemble, a registered Great Estate built in 1881, is set in the heart of downtown Lenox. Originally a Gilded Age estate, it has been updated and is now offered fully furnished as a turnkey luxury rental. The property is designed for groups, with multiple gathering spaces, a well-equipped kitchen, a mahogany bar, and 13 en-suite bedrooms. It comfortably accommodates 20+ guests and has been a strong performer for weddings, corporate retreats, and multi-generational stays. The grounds feature open lawns, established gardens, and west-facing views. Fully ADA compliant and walkable to Lenox's restaurants, shops, and cultural venues. A rare opportunity to own a large-scale, income-producing property in one of the Berkshires' most established locations.

2 Kemble, Lenox

Listing courtesy of Listing Agent: Cameron Volastro from Listing Office: William Pitt Sotheby's International Realty.

$4,850,000

4 Beds ⋅ 5 Baths ⋅ 73360776 MLS

Sunshine Daydream - recently completed and ready to go. Located on a quiet street in desirable 'Sconset village, this newly constructed Cape-style cottage has been thoughtfully expanded and fully renovated. Designed with an efficient use of space and the island lifestyle in mind, the four bedroom home with oversized garage and studio suite is ideal for coastal living and checks all the boxes. The flexible layout offers various options for entertaining and a potential fifth bedroom for guests. Enjoy outdoor living with a large private yard, inviting front porch, wrap around deck and heated Plunge pool all surrounded by native landscaping and custom hardscape. Finished in 2026 and being offered turnkey furnished. Ownership member is a licensed real estate agent in Massachusetts.

8 Sconset Ave, Nantucket

Listing courtesy of Listing Agent: Paul Drepanos from Listing Office: Compass.

$4,800,000

5 Beds ⋅ 4 Baths ⋅ 5095530 MLS

Deep mountain solitude meets luxury for the elite sportsman seeking an unprecedented legacy getaway. Mountain views stretching 80 miles include Jay Peak, and Clarksville Pond. Ricker Road transforms into the ultimate fall refuge, inviting you to hunt miles of vibrant trails. Up to 440 additional acres are offered separately, presenting a rare opportunity for privacy. Wilderness meets sophisticated opulence in this Douglas Fir timber frame residence. Every inch boasts premium, ultra-luxury interior finish work, featuring soaring cathedral ceilings, magnificent timber-frame architecture, and rich hardwood and tile flooring designed for hosting in absolute comfort. Engineered for absolute autonomy, the estate integrates premium, high-efficiency energy systems and a commercial-grade standby generator -delivering flawless, independent power and climate control. The estate’s elite infrastructure matches this caliber: a heated, two-level Maintenance Barn features plumbing and dual high-clearance bays - the ultimate command center for a premium collection of recreational vehicles. Complementing it is the Restored Heritage Barn, a structurally renewed historic cattle barn primed for transformation into an equine barn or whatever your heart desires. Cast from the private dock into your 40-foot-deep stocked rainbow trout pond, or launch your boat at Clarksville Pond across the road. For outdoor enthusiasts, enjoy direct access to the greater regional snowmobile and ATV trail systems alongside your own meticulously maintained private recreational trails. A custom 6-hole golf course rounds out this wilderness retreat, featuring room to add holes, alongside a massive field prime for a private aviation runway. While nearby Pittsburg is the region's hunting, fishing, and snowmobiling haven, saturation has compromised its solitude. Clarksville offers the same legendary access to world-class sporting culture, but with the untouched, elite remoteness true privacy demands.

39 Ricker Rd, Clarksville

Listing courtesy of Emily M Locke from KW Vermont-Stowe. (Cell: 802-760-6124)

$4,800,000

4 Beds ⋅ 5 Baths ⋅ 73502038 MLS

Tucked along one of the most sought-after streets in West Cambridge, between Harvard Square & the Charles River, this beautifully proportioned home blends historic character with everyday convenience. Mercer Circle, originally called Telephone Street, is part of a storied enclave developed by Gardiner G. Hubbard, founder of the National Geographic Society and 1st president of Bell Telephone Company. The property showcases a 29' covered wrap-around porch overlooking specimen plantings. Inside, gracious rooms are defined by tall windows & ceilings, fireplaces, and custom built-ins. Outside, the irrigated fruit gardens yield plums, blueberries, apples, and vegetables. Ideally located just 0.2 miles from BB&N’s Lower and Middle Schools and approximately one mile from Shady Hill School & BB&N’s Upper School. Properties on Mercer Circle are rarely offered, as residents tend to stay for generations, drawn by the tranquil setting, community, & enduring curb appeal.

6 Mercer Circle, Cambridge

Listing courtesy of Listing Agent: Gail Roberts, Ed Feijo & Team from Listing Office: Coldwell Banker Realty - Cambridge.

$4,800,000

5 Beds ⋅ 7 Baths ⋅ 73494280 MLS

Set on 5.6 private acres on Weston’s highly desirable south side, this impressive estate offers exceptional privacy and timeless appeal. Tucked at the end of a long, winding driveway, this Federal Colonial blends classic architecture with comfortable living, featuring sun-filled interiors, a dramatic two-story family room with fireplace, a bright sunroom, and a stylish home office. The flexible layout includes a first-floor bedroom suite ideal for guests, while upstairs offers five bedrooms, including a spacious primary suite with fireplace, luxurious bath, dressing area, and multiple walk-in closets, along with four additional bedrooms and three full baths. The finished walk-out lower level with a separate entrance includes a kitchen, bedroom, full bath, exercise and media rooms—perfect for extended living or entertaining. Complete with a five-car garage and located just minutes from the state’s top public schools, with convenient access to Boston.

451 Wellesley St, Weston

Listing courtesy of Listing Agent: Yang Liu from Listing Office: Weston Realty LLC.

$4,800,000

6 Beds ⋅ 7 Baths ⋅ 73466199 MLS

Over the past century, The Loring-Atherton House has been owned by just two families. Now, this distinguished Cottage Farm residence presents a rare opportunity for its next owner to thoughtfully reinterpret it for a new era. Set on a prominent corner lot in the heart of Brookline’s Cottage Farm Historic District, the residence is an exceptional example of Georgian Revival architecture. Its stately brick exterior is defined by a slate roofline, dormer windows, tall chimneys and a classically detailed entrance crowned by an arched fanlight. At the rear, a broad brick terrace, graceful curved staircases and a multi-paned bay overlook the mature, tree-canopied grounds. Inside, the home reveals an extraordinary collection of architectural details. A dramatic great room features a soaring exposed timber ceiling, hand-painted decorative friezes, richly paneled walls, built-in bookcases and window seating, and a substantial marble fireplace. Elsewhere, a beautifully crafted wood staircase, patterned tile floors, ornamental ironwork, additional fireplaces and a mural-lined library speak to the artistry and character carried throughout the residence. Together, these elements provide a compelling architectural language from which something entirely personal can be created. Currently offering six bedrooms and six and a half bathrooms across approximately 8,326 square feet of finished living space, the property encompasses more than 10,000 square feet of finished and unfinished space in total. The opportunity is not simply to restore what was, but to consider how its most distinctive elements can inform what comes next, creating a home that feels relevant to the present while remaining connected to its remarkable history. Directly across from Mason Square Park and moments from the Longwood Medical Area, Fenway, Boston University, leading schools and many of the region’s finest cultural and green spaces, 180 Ivy Street offers the architectural character and greenery of Brookline while keeping Back Bay, downtown Boston, Cambridge and Harvard University all within easy reach. More than a significant address, it is an opportunity to carry forward a century-long legacy while defining its next era.

180 Ivy St, Brookline

Listing courtesy of Listing Agent: Ricardo Rodriguez & Associates Group from Listing Office: Coldwell Banker Realty - Boston.

$4,799,000

6 Beds ⋅ 7 Baths ⋅ 73509976 MLS

JUST COMPLETED. FINAL LANDSCAPING UNDERWAY. Timeless home by a premier local developer in iconic West Newton Hill. A sun-drenched foyer with custom millwork, soaring ceilings, & expansive windows creates a striking first impression, opening to elegant living & dining spaces. The kitchen is the heart of the home, outfitted with high-end appliances, inset cabinetry, an oversized waterfall island, scullery, and pantry, flowing seamlessly into a warm, inviting family room with fireplace and custom built-ins overlooking the landscaped backyard and covered patio. A breakfast area framed by floor-to-ceiling windows captures natural light throughout the day. A first-floor suite/office with patio access. A large mudroom with custom built-ins & direct access to heated garage. Upstairs, four ensuite bedrooms with custom closets, anchored by a serene primary suite with built-ins, bar, fireplace, spa-like bath, walk-in closet & private balcony. Finished lower level w/den, bar, bedroom, bath, & gym.

1640 Commonwealth Ave, Newton

Listing courtesy of Listing Agent: Lena Voloshin from Listing Office: LV Group Real Estate.

$4,795,000

5 Beds ⋅ 7 Baths ⋅ 22603117 MLS

Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores & restaurants & only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors & custom trim detail, beadboard ceilings, & crown molding. The home is positioned seamlessly on a large .52 acre lot with a spacious back yard, a brand new vinyl saltwater pool, outdoor shower, a screened in porch, large patio area, & an outdoor pool cabana w/ a bathroom. This home is perfect for those special summer nights on Cape Cod sitting by the pool and relaxing. Each bedroom includes it's own full bathroom including the 1st floor primary suite bedroom. A few other features added by the builder: a whole house generator, gas fireplace, irrigation system, & a 1-year builder warranty as well. Come see your dream home today before it's too late!

22 Scudder Road, Osterville

Listing courtesy of Listing Agent: Sean Dacey (sean.dacey@nemoves.com) from Listing Office: Coldwell Banker Realty.

$4,795,000

5 Beds ⋅ 7 Baths ⋅ 73542127 MLS

Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores & restaurants & only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors & custom trim detail, beadboard ceilings, & crown molding. The home is positioned seamlessly on a large .52 acre lot with a spacious back yard, a brand new vinyl saltwater pool, outdoor shower, a screened in porch, large patio area, & an outdoor pool cabana w/ a bathroom. This home is perfect for those special summer nights on Cape Cod sitting by the pool and relaxing. Each bedroom includes it's own full bathroom including the 1st floor primary suite bedroom. A few other features added by the builder: a whole house generator, gas fireplace, irrigation system, & a 1-year builder warranty as well. Come see your dream home today before it's too late!

22 Scudder Road, Barnstable

Listing courtesy of Listing Agent: The Quirk Group from Listing Office: Coldwell Banker Realty - Boston.

$4,795,000

5 Beds ⋅ 4 Baths ⋅ 5093615 MLS

A rare Lake Winnipesaukee offering, this legacy property features 300 feet of pristine waterfront and over 2.7 private acres and spectacular views, ideally situated between Meredith and Center Harbor, providing convenient access to shopping, dining, marinas, and all the attractions of the Lakes Region. Turn into the beautiful winding driveway and shortly you will be at home. Blending classic lakehouse charm with modern amenities, this inviting waterfront retreat is designed for gathering and making memories. The spacious kitchen is a chef's dream, featuring an 8-burner Viking range, walk-in pantry, wet bar, and ample space for entertaining. Multiple living areas, highlighted by two fireplaces, offer comfortable places to relax in every season, while the screened porch provides the perfect setting for morning coffee or evening dinners overlooking the lake. The main level includes a bedroom and ¾ bath, offering flexibility for guests and convenient first-floor living. Upstairs, the primary suite enjoys its own large private deck with sweeping water views, accompanied by two additional bedrooms and a full bath. Beautifully landscaped grounds lead to the waterfront, where two private docks, walk-in lake access, with sandy bottom and 300 feet of shoreline create an exceptional setting for boating, swimming, and enjoying life on the lake. An adorable bunkhouse with its own screened porch and ¾ bath provides a charming guest retreat just steps from the water. Additional features include a detached two-car garage with a screened porch and finished space above, as well as a detached barn offering abundant storage for boats, water toys, and recreational equipment. Combining exceptional privacy, extensive waterfrontage, and close proximity to everything by car or by boat, this is a unique opportunity to own a classic Lake Winnipesaukee property ready to be enjoyed for generations to come. 6 BR State approved septic.

28 Veasey Shore Rd, Meredith

Listing courtesy of Ellen Mulligan from Coldwell Banker Realty Center Harbor NH. (Cell: 603-387-0369)

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