Great Island Real Estate

Welcome to Great Island, a hidden gem nestled in the picturesque town of Plymouth, Massachusetts. This enchanting subdivision offers a unique blend of coastal charm and suburban tranquility, making it the perfect place to call home.

Great Island is renowned for its stunning waterfront views and serene atmosphere, providing residents with a peaceful retreat from the hustle and bustle of everyday life. Imagine waking up to the gentle sound of waves lapping against the shore, with the scent of saltwater filling the air. Here, you can enjoy picturesque sunrises and sunsets that paint the sky in vibrant hues, all from the comfort of your own backyard.

The community is characterized by its beautifully designed homes, each showcasing meticulous craftsmanship and modern amenities. With spacious layouts and lush landscaping, Great Island offers a variety of housing options to suit every lifestyle, whether you’re a growing family, a retiree, or a young professional seeking a serene place to settle down.

Residents of Great Island benefit from easy access to Plymouth's rich history and vibrant culture. Explore the charming downtown area, filled with boutique shops, delightful restaurants, and historical landmarks. The nearby beaches provide endless opportunities for outdoor activities, from swimming and sunbathing to kayaking and fishing.

In addition to its natural beauty and recreational offerings, Great Island is conveniently located near major highways, making commutes to Boston and other neighboring towns a breeze.

Discover the charm and allure of Great Island, where coastal living meets community spirit. Your dream home awaits in this idyllic Plymouth subdivision!

Newest Listings in Great Island

$800,000

2 Beds ⋅ 3 Baths ⋅ 73572237 MLS

Single level living in this Franklin-style attached home is located in the sought-after 55+ community of Great Island by Del Webb in the award winning Pinehills. This thoughtfully designed home includes 2 bedroom and 2 bath, kitchen and formal dining room with decorative molding. The spacious living room features a cozy gas fireplace, vaulted ceiling and a sliding glass door that opens onto your screened porch which opens to your back deck and stairs to backyard. Kitchen with pantry, and a sunny eat-in breakfast nook with a light filled bay window. The generous primary suite, has a large walk-in closet with closet system, primary bath with double vanity, soaking tub, and separate shower. A guest bedroom and a full guest bath and laundry complete the main level. Walk out lower level includes two generous bonus rooms and 3/4 bath. Easy to expand sleeping quarters when needed. Overlook Clubhouse with outdoor Tennis, Pickle Ball, Bocce , indoor pool and jacuzzi, fitness room, Billiards, and more with a fulltime Lifestyle Director. Number of updates in the last 5 years include; Garage Cabinet System, Walk in closet system in primary bedroom, New Fireplace, New fan in 3 season porch, epoxy garage floor, New washer and dryer, NEW HVAC SYSTEM 2023.

26 Cross Wind, Plymouth

Listing courtesy of Listing Agent: Pinehills Resale team from Listing Office: Pinehills Brokerage Services LLC.

$735,000

2 Beds ⋅ 3 Baths ⋅ 73562184 MLS

Not only is summer over — so is your house search! Step inside this gorgeous, move-in ready home in Great Island and you'll immediately start picturing where your furniture will go. Settle in for fall and enjoy the foliage on nearby walking trails. Stay active with pickleball, swimming laps,or simply unwind with a pumpkin spice coffee and a good book on the screened porch. Fast forward a few months, and your driveway will have been plowed and your front steps shoveled — all while you stay warm and cozy in front of the gas fireplace. The bright, sunny floor plan offers true one-level living, with a first-floor en suite primary and a versatile den perfect as an office, craft room, guest room, or gym. The large, open dining room is ideal for hosting holidays or welcoming new neighbors for dinner. Upstairs, you'll find a spacious bedroom, a Jack-and-Jill bath, an open living area, and a bonus space that adapts to however you need it — plenty of room for family and friends when they come to visit. Impeccably maintained by original owner, this home offers upgraded features that set it apart: two car attached garage, vaulted ceilings, additional windows including transoms and a triple bay window, high ceilings, hardwood floors, updated kitchen with stainless steel appliances, laundry room with pedestals, irrigation system, upstairs flex space with window seat, large unfinished basement and a new heat pump/AC condenser installed in 2025. Set on a quiet street in an excellent location, this home is just a short walk to the Overlook Clubhouse, offering an indoor pool, fitness center, billiards, social spaces, bocce, tennis, and pickleball. Come see this home for yourself — and discover why the Great Island 55+ community is so popular!

9 Canoe Lndg, Plymouth

Listing courtesy of Listing Agent: Derek Greene from Listing Office: The Greene Realty Group.

$825,000

3 Beds ⋅ 3 Baths ⋅ 73562183 MLS

Welcome to Great Island, the 55+ Del Webb neighborhood located in the award winning Pinehills. If one of your favorite things to do is to host family gatherings this might be the perfect floor plan for you. The Newhall style floor plan has an incredible, separate, dining room with bay window, that EASILY seats 8 guests. And that is just the beginning of all that is wonderful about this floor plan. First floor office/den has french doors and is tucked around the corner from the main living area. Which - if you work from home could be a good thing as it creates a little separation. Guest suite on the first floor almost has its own wing and feels very private. Primary suite has a deep tray ceiling and the primary bath has double vanity, soaking tub, step in shower and walk in closet. Eat in kitchen has plenty of counter space for your favorite kitchen gadgets. Kitchen overlooks the living room with fireplace which overlooks the screened porch. This screened porch feels a little bit like a treehouse with the surrounding natural beauty and private setting. Second floor includes enclosed loft, second bedroom, bath and big closets. Everyone has their own space. If you find you need a little more room there is an unfinished walk out basement with roughed in plumbing. New AC 2022. Central vaccuum system. Located minutes from the Amazing Overlook Clubhouse with indoor swimming pool, tennis and pickle ball, craft rooms, card rooms and full time activities director. Stonebridge Club has the outdoor swimming pool and clay tennis courts.

22 Cross Wind, Plymouth

Listing courtesy of Listing Agent: Pinehills Resale team from Listing Office: Pinehills Brokerage Services LLC.

$691,050

2 Beds ⋅ 3 Baths ⋅ 73554408 MLS

Exceptional Value for this single family attached "Milton" style home is located in the 55+ Great Island neighborhood at The Pinehills. A two-story foyer with an open staircase greets you at the entry. Dine in kitchen is a great place to cook with a cozy nook. An elegant dining room has hardwood flooring, crown molding trim and chair-rail with a bay window. Living room has a feature wall and slider to spacious deck with private wooded views. The primary suite, with bath and shower plus walk-in closet, is on the main floor. The laundry room and office with built in bookshelves add to the first level with a sunroom and patio for outdoor living. Second floor has a den, guest bedroom, bonus room with closet and a full bath. Enjoy amenities at the Overlook Clubhouse with indoor pool and jacuzzi, fitness center, billiards room, fitness room, walking trails, outdoor tennis, pickle ball and bocce. Access to Great Island Pond & Stonebridge Club all part of HOA, with snow removal.

5 Highbank Trail, Plymouth

Listing courtesy of Listing Agent: Pinehills Resale team from Listing Office: Pinehills Brokerage Services LLC.

$725,000

2 Beds ⋅ 3 Baths ⋅ 73547838 MLS

The Milton model in the sought-after 55+ Great Island neighborhood at The Pinehills offers the perfect blend of comfort, style and functionality. A welcoming two-story foyer with an open staircase sets the tone for this thoughtfully designed home. The eat-in kitchen flows seamlessly into the great room, where a gas fireplace creates a warm and inviting gathering space with access to a spacious deck overlooking a peaceful, private setting. The formal dining room is enhanced with elegant crown molding, creating the perfect setting for holidays and special gatherings. The first-floor primary suite offers a walk-in closet and private bath. A beautiful library with wall-to-wall custom built-ins, first-floor laundry and half bath complete the main level. Upstairs you’ll find a home office, guest bedroom, bonus room with closet and full bath. Enjoy the Overlook Clubhouse with indoor pool, fitness center, tennis, pickleball, bocce, billiards, Great Island Pond, scenic walking trails and more!

7 Madison Reach, Plymouth

Listing courtesy of Listing Agent: Lynne Morey from Listing Office: Coldwell Banker Realty - Plymouth.

$899,000

2 Beds ⋅ 3 Baths ⋅ 73546214 MLS

Light, bright and airy describes this sought after "Adler" floor plan that has been lovingly updated and maintained. Ideally located in the Great Island neighborhood at The Pinehills. Two bedrooms, including a primary suite, and an office on the first floor. 3 season screened porch has been transformed into a year round heated 4 season room with new windows and new door (2026). Perfect spot for your morning coffee as you start the day by taking in the beautiful wooded view. The timing is perfect to step outside to the new extended 18'x12' deck (2025) complete with awning for summer-long enjoyment. Home has the added luxury of a walk out, finished lower level with natural light. Two generous sized bonus rooms and full bath allows you to create the spaces needed that fit the flow of your life. New HVAC 2023.The Overlook Clubhouse with indoor swimming pool, exercise room and myriad of activities, also comes with a full time activity director.

28 Cottage Cove, Plymouth

Listing courtesy of Listing Agent: Pinehills Resale team from Listing Office: Pinehills Brokerage Services LLC.

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