From large outdoor decks to sprawling backyards these homes offer great outdoor entertaining areas. See below!
27 Pierce Lane, Edgartown | $7,400,000


Paul Pertile

Paul Pertile
Own a piece of island history with this exquisitely restored 1830’s house which was owned and built by Doctor John Pierce. Stand out on Pierce Lane! This desirable location is within walking distance to downtown Edgartown and sits on a .27 acre lot.
Listing details: The property features ample parking, a single-bay two-car garage, a beautiful pool with a pool house, and a professionally landscaped yard with a patio that overlooks Sheriff’s Meadow. Three porches and a spacious sunroom add a nice touch to this home for the summer months and three fireplaces make it ideal for the winter.
- Price:
- $7,400,000
- Size:
- 3,910 sq ft
- Contact:
- Paul Pertile , Match Point Properties , +1 508.221.8028
Fantastic Living In Myopia Hill | $2,189,000


Peter Rooney

Peter Rooney
Welcome home to this rare opportunity to live in Myopia Hill! Less than .5 miles to Boat & Country Clubs, a beautiful stone Tudor with landscaped grounds is ideal for families or entertaining.
Listing details: Boasting amazing details; 13 spacious rooms, 6 spacious bedrooms, 3.5 bathrooms, 4 fireplaces, 2 staircases, hardwood floors throughout, crown moldings, wood beams, and more! Master bedroom with a luxurious bath & steam shower that has views of Mystic Lake. Chef’s eat-in kitchen with a Wolf range, dining island & wet bar steps out to the patio with a firepit overlooking the backyard and abutting conservation land.
- Price:
- $2,189,000
- Size:
- 4,712 sq ft
- Contact:
- Peter Rooney, William Raveis Real Estate , +1 508.958.8195
82 Chestnut Hill Loop | $1,950,000


Jeff Loholdt & Herb Butzke

Jeff Loholdt & Herb Butzke
Antique farmhouse on 419 acres with Trout Pond and Barns! Welcome to Redbrook Farm, the quintessential New England farmhouse tucked amidst one of the largest private landholdings in the Commonwealth being offered today.
Listing details: Beautiful Chestnut Timber construction with wide plank flooring and open concept kitchen to the living area. Unparalleled historic charm with today’s conveniences making this a truly special offering. 4 bedrooms, 2 bathrooms, and two barns complimented by fenced grazing land for whatever one wishes to home.
- Price:
- $1,950,000
- Size:
- 2,684 sq ft
- Contact:
- Jeff Loholdt & Herb Butzke , William Pitt Sotheby’s International Realty , +1 413.652.7423
Truly Special & Unique Home | $1,430,000


Cindi Lee McTiernan

Cindi Lee McTiernan
Your Quincy Castle awaits! This timeless and elegant Brick Tudor Revival home is situated on 3/4 of an acre, a rare find! The land, once part of the Adam’s Farm and is across the street from Peace Field, the home of John Adams.
Listing details: This truly special and unique home built in 1930 offers old-world charm and rich period details throughout. The circular stone foyer leads to an open living and dining room with hardwood floors, beamed ceilings, French pocket doors, an oversized fireplace, and floor-to-ceiling windows that overlook the pool and patio area.
- Price:
- $1,430,000
- Size:
- 4,948 sq ft
- Contact:
- Cindi Lee McTiernan , Success! Real Estate , +1 781-389-6526
Private Enclave Of Blythewood Estates | $1,300,000


Victoria Standring

Victoria Standring
Stunning contemporary located in the private enclave of Blythewood Estates. Expert craftsmanship and attention to detail grace this meticulously well-maintained 5 bedrooms, 5.5 bathrooms home.
Listing details: The dramatic two-story primary bedroom suite offers direct access to the pool. A floor-to-ceiling stone fireplace graces the living room, and the newly renovated lower level offers theatre, gym, and gaming space. Whether working from home or entertaining friends and family in style, you will delight in the abundance of interior spaces.
- Price:
- $1,300,000
- Size:
- 5,122 sq ft
- Contact:
- Victoria Standring , Stone House Properties , +1 413.822.5363
60 Sassamon Ave | $900,000


Thomas O’Neill

Thomas O’Neill
Looking to get into the Milton market or upside in Milton? Well, look no further. This home has it all! 5 bedrooms, 2.5 bathrooms, and a large open family room. A full walk-out basement with a spacious finished area, lots of parking, a detached 2 car garage with tons of storage, and a heated bonus room.
Listing details: If you need even more space the oversized 13,473 square foot lot provides plenty of room to expand. This solid home with a brand new heating system is in a highly desirable neighborhood near Wollaston Country Club and at the edge of the Blue Hills Reservation.
- Price:
- $900,000
- Size:
- 2,244 sq ft
- Contact:
- Thomas O’Neill , Success! Real Estate , +1 617.721.5966

















