9 Stunning Coastal and Countryside Estates in Massachusetts

This spacious, bright and airy, 6 bedroom home with multiple living spaces inside and out. All 3 floors feature bedrooms, bathrooms, large living rooms with fireplaces with ample seating, large TVs, and access to a furnished deck, porch or patio.

Size: 3,704 sf

Price: $4,245,000

Listing details: The lower level has 2 large bedrooms with en suite bathrooms, walk in closets and a living room with fireplace. Entry level has three bedrooms, 2 baths, laundry, and living room with fireplace. Two of the bedrooms are joined by a Jack and Jill style bathroom and the third is ensuite. Upstairs you will find the luxurious primary bedroom and bath, open dining, living and kitchen and a 1/2 bath complete this floor. Incredible harbor and town views from widows walk. Fully stocked kitchen, high-end furnishings, fine linens and towels convey with the property. All bedrooms contain a queen or king size bed and a flat screen TV. All common living spaces have a flat screen TV and fireplace. 0.20 miles to Monomoy Beach.

Contact: Gary Winn, Morgan Winn & Susan Lazarus, Maury People Sotheby’s International Realty, +1 508.330.3069, 508.332.9088

HIGHLIGHTS AT A GLANCE

• Secluded pool and outdoor kitchen/ patio with fireplace and shower

• Complete gym/full bath and dressing room

Size: 11,907 sf

Price: $3,950,000

Listing details: 

• Lower level billiards room/bar with fireplace and half bath

• Easterly sun room and westerly three season porch

• Dramatic eat-in kitchen/family room with fireplace

• 6 bedrooms (elegant primary suite) and 5 full and 2 half baths

Contact: Nancy & Tom Hamilton, Compass, +1 401.965.2981, 781.738.2650

Seaside masterpiece… Underpinned by a sense of openness and lightness, the inspirational views of Buzzards Bay anchor ‘most every room of this unparalleled oceanfront home. Understated sophistication & attention to every detail set the tone for this versatile open floor plan. Exquisite foyer is framed by a graceful arch, leading to formal dining room with custom built-in buffet cabinet spanning the length.

Size: 6,000  sf

Price: $3,895,000

Listing details: A stunning gourmet kitchen with oversized quartz island spills into the casual yet elegant living room with several distinct entertaining spaces. The home offers two glamorous primary suites, one on each level, both with luxurious bathrooms as well as two additional bedrooms and baths, versatile family room/bedroom, and dazzling home office. The fine craftsmanship includes coffered and tray ceilings, custom millwork, wide plank beech tree floors. Enjoy a private sandy beach with room for a waterside pool.. minutes to Padanaram Village with its shops, restaurants, yacht club.

Contact: Sarah Meehan, Milbury and Company, +1 508.685.8926

Escape to your own lakefront sanctuary nestled in the Berkshires. This enchanting lakefront property offers a rare opportunity to create your dream retreat. With over 500 feet of private waterfront, this expansive estate is a haven for those seeking peaceful tranquility and natural beauty from the breathtaking views and serene surroundings, or this property has the potential for multiple building sites.

Size: 59 acres

Price: $3,575,000

Listing details: The 3,940 sq. ft. home features five spacious bedrooms and six bathrooms providing ample space for family and friends. Become part of the Berkshires renowned for its stunning landscapes, vibrant cultural scene, and outdoor recreational activities.

Contact: Suzann Ward, Housatonic Real Estate, +1 413.329.3031

Designed by H. Davidson, this house boasts a striking presence with its brick exterior and triple slate roof. Lavish proportions and exceptional woodwork showcase distinctive architectural details throughout.

Size: 5,662 sf

Price: $3,295,000

Listing details: Inside, gleaming wood floors and tall ceilings enhance the grand spaces, perfect for entertaining. The first floor features a cozy library, an expansive living room anchored by an oversized wood-burning fireplace, and a solarium that opens to private gardens, ideal for al fresco dining. The formal dining room flows seamlessly from the spacious, renovated kitchen. Upstairs, the generous primary suite is a serene and relaxing retreat with an en-suite bath, a walk-in closet, and a fireplace. Five additional bedrooms and two additional family baths complete the second floor. An attached two-car garage includes an additional living area with a bathroom, a perfect space for an au pair. Located near the C and D lines, this home is close to all the urban amenities Brookline has to offer.

Contact: Eileen Kibrick O’Grady, Coldwell Banker Realty, +1 617.953.9622

High on Miller Hill overlooking Cape Cod Bay sits this impressive Captain’s House with 8 bedrooms, 7 baths. The views dominate here – endless sky and sea, Long Point, Truro, Wellfleet and the rooftops of Provincetown as you sit high above. The best of both worlds awaits at this location: proximity to the Gallery District, East End restaurants, shops and the beaches, but distant from noise and crowds. Currently operated as Aerie House, a well-known and respected inn, this property would make an excellent single family home or, possibly, a condominium conversion.

Size: 3,100 sf

Price: $3,249,000

Listing details: With curated gardens, four decks and two patios, the outdoor space is designed for happy summer living and easy entertaining. The main, second floor spacious deck was designed for entertaining with its own bar and magnificent views – perfect for watching the 4th of July fireworks or simply the starlit skies. Well maintained, regularly updated and improved over the years, this property is suitable for a variety of configurations to maximize value and enjoyment.

Contact: Tim Brown, SeasCape Realty, Inc., +1 508.468.9338

Water Front Home with Private Dock and Mooring. Breathtaking Sunrises and Sunsets daily that you never get tired of.

Size: 3,513 sf

Price: $3,200,000

Listing details: Imagine living on the water edge with unobstructed panoramic views of Ninigret Pond and the Atlantic Ocean.

Contact: Peter P. Dandurand, Dandurand Real Estate, +1 401.529.3131

Tucked away in the heart of Sesuit Neck, one of East Dennis’s most treasured enclaves, lies a property of understated elegance and unparalleled charm. Spanning over 2.6 wooded acres, this retreat offers a rare combination of seclusion and proximity to the Cape’s most beloved treasures. A quiet path winds through the trees, leading to the sandy shores of Cape Cod Bay, where deeded beach rights ensure a slice of coastal serenity that feels worlds away. At 3,456 square feet, this home balances space and intimacy, designed for gatherings that linger long into the evening or quiet mornings with coffee on the porch. Built with enduring craftsmanship and cared for by two families, this home is steeped in a legacy of laughter, warmth, and cherished memories. Here, the rhythm of life is set by the soft rustle of leaves in the breeze and the distant call of gulls overhead. This is not just a home but a canvas for new traditions–a secluded haven where every season brings its own beauty.

Size: 3,456 sf

Price: $2,999,000

Listing details: Whether you envision summer afternoons with sandy toes and salty breezes or cozy winter nights by the fire, this Sesuit Neck retreat offers a rare opportunity to embrace the Cape Cod lifestyle at its most authentic. Located just minutes from Dennis Village, you’ll find charming theaters, unique boutiques, and delightful restaurants at your fingertips. Whether savoring a lobster roll at Sesuit Harbor Café or exploring the lively village spirit, the best of Cape Cod living is right outside your door. Move-in ready yet full of potential for future enhancements, this home strikes the ideal balance between comfort and opportunity. With its unmatched acreage, private beach access, and premier location, 32 Oliver Drive is not just a home it’s your gateway to the Cape Cod lifestyle you’ve been dreaming of. Don’t miss this extraordinary offering. Schedule your private showing today and start creating your coastal legacy.

Contact: Cindy Harrington, Berkshire Hathaway HomeServices Robert Paul Propertiess, +1 508.776.8181

Nestled in the heart of Newport’s Historic Point neighborhood, Willows Edge, built in 1731 by Newport Quaker James Davis, has stood proudly at its corner for nearly three centuries. The finest artisans and craftsmen have meticulously restored this home. From the foundation to the exterior, every detail has been preserved and enhanced with unparalleled care.

Size: 2,600  sf

Price: $2,195,000

Listing details: Offering five bedrooms and four and a half updated bathrooms across three floors, there is space for everyone. This home masterfully blends modern amenities with the charming elegance of the past. The custom-milled exterior, paired with wide plank interior floors and six fireplaces, exudes warmth and craftsmanship. Every inch of this property reflects a deep respect for its history, with no expense spared to ensure its longevity for the next 300 years. The garden edged and fenced back yard is an unexpected oasis to enjoy throughout the seasons. The lovely curb appeal of this property is enhanced by the brick driveway. Set in one of Newport’s most sought-after and historically significant neighborhoods, you will be surrounded by beautifully preserved colonial homes and moments from the waterfront, shopping and fabulous eats. Willow’s Edge invites you to experience this remarkable fusion of old and new. This is a home built to stand the test of time and is ready to welcome its next chapter.

Contact: Kimberly Marion, Engel & Volkers, +1 401.692.1644