Pinehills Real Estate

Welcome to Pinehills, a charming and picturesque community nestled in the heart of Plymouth, Massachusetts. Known for its stunning natural beauty and vibrant lifestyle, Pinehills offers a unique blend of suburban tranquility and modern conveniences, making it an ideal place to call home.

As you explore this enchanting region, you'll be captivated by its rolling hills, lush woodlands, and meticulously designed landscapes. Pinehills is not just a neighborhood; it’s a lifestyle, featuring an array of beautiful homes that cater to diverse tastes and preferences. From elegant single-family residences to low-maintenance condominiums, there’s something for everyone in this thriving community.

One of the standout features of Pinehills is its commitment to preserving the environment and promoting an active lifestyle. With miles of walking trails, scenic parks, and recreational areas, residents can easily enjoy outdoor activities year-round. The community is also home to two championship golf courses, perfect for both seasoned players and newcomers alike.

Pinehills boasts an impressive selection of amenities, including charming shops, gourmet dining options, and a vibrant community center that hosts various events and activities throughout the year. Plus, with its proximity to historic Plymouth, residents can easily explore the rich history and culture of the area, from the iconic Plymouth Rock to the beautiful waterfront.

Whether you’re seeking a peaceful retreat or an active lifestyle, Pinehills offers an unparalleled living experience in one of Massachusetts’ most desirable locations. Come discover the charm of Pinehills and find your perfect home in this idyllic community!

Newest Listings in Pinehills

$739,900

2 Beds ⋅ 3 Baths ⋅ 73555573 MLS

The award winning Binnacle Townhome Model Home! Rare chance to purchase the beautifully designed former model home for Symington Woods. This home offers 3 floors of luxury living, thoughtfully designed for entertaining and relaxing. Upgrades include Quartz counters, finished lower level, tiled shower, custom closets, and so much more!

1 Heartwood, Plymouth

$850,000

3 Beds ⋅ 3 Baths ⋅ 73555562 MLS

Two layers of outdoor living! One is a covered screened porch with ceiling fan and the other is a 12 foot, open air, enclosed deck. Located in the award winning Pinehills in the Del Webb 55+ Great Island neighborhood. The "Laurel" floor plan is a favorite because everything needed for first floor living is included on the main floor. The kitchen features granite counters, ample cabinets and a charming breakfast nook that overlooks your enclosed screened porch — perfect for enjoying morning coffee year-round. Private primary suite with double vanity, tub, step-in shower and generous walk-in closet. Hardwood floors throughout the main living areas. Two story foyer and two story family room make the home feel bright and airy. Office, tucked away at the front of the home with wall to wall carpeting, built in bookshelves and a view of the streetscape. Second floor has two guest bedrooms and loft area. Perfect getaway for guests and the grandkids when they come to stay. Overlook clubhouse with indoor swimming pool, bocce courts, tennis and pickle ball courts & a myriad of activities.

6 Clam Pudding, Plymouth

$923,000

3 Beds ⋅ 3 Baths ⋅ 73555241 MLS ⋅ ['Seton Highlands'] BLDG.

Simply Beautiful describes this condo! This like new "Chatham" style home in the Seton Highlands 55+community in The Pinehills has many upgrades. Located in a cul de sac. The open floor plan in this sun-filled home invites you into the living room with stone surround fireplace, built ins, and a bay window. The kitchen/dining area has a slider which opens to a generous size composite deck with an awning overlooking the spacious backyard and a beautiful private, wooded view. The kitchen has upgraded cabinets, Bosch SS appliances, double ovens, & gas cooktop. The den is right off the kitchen. The primary ensuite is located on the main level, with tiled shower, double vanity sinks, large walk-in custom closet, and a laundry room. The second level has an amazing bonus room, guest bedroom, loft, full bath and a flex/bedroom/craft room. The HOA covers all exterior maintenance and landscaping, clubhouses, exercise rooms, game room, pools, club activities and tennis. A must see!

24 Inverness Unit 24, Plymouth

$1,245,239

3 Beds ⋅ 3 Baths ⋅ 73555070 MLS ⋅ ['Bentgrass Mist'] BLDG.

PINEHILLS -- THE LAST AVAILABLE HOME AT BENTGRASS MIST! NEW FRESCO 3 PLUS DESIGNER HOME READY FOR MOVE IN FALL OF 2026 . Located in the heart of the village green, where the shopping, restaurants, golf and spa are just a short stroll away. The award-winning Fresco 3 Plus home will not disappoint. This 3-bedroom, 3 full bath condominium boasts a spacious floor plan, screened in porch and private courtyard. The primary bedroom is located on the first floor along with a guest bedroom that can also be used for an office space. The second floor allows guests to have their privacy hosting a loft and full bathroom. A walkout lower level lends for great storage or additional living space. Enjoy the luxury of new construction and condominium living including all the Pinehills amenities. With interior selections made by our exclusive design team this home is a true show piece! Nothing to do but move right in!

70 Bentgrass Mist Unit 70, Plymouth

$963,205

2 Beds ⋅ 2 Baths ⋅ 73555071 MLS

PINEHILLS --- NEW very popular FRESCO 2 currently being built, ANTICIPATED FALL 2026 MOVE IN. $65,000 of selected options applied at no cost to buyer. Located high on the Ridge with a vista view of the Atlantic and tall pines, this designer home will not disappoint. This 2-bedroom, 2 full bath, condominium boasts a spacious floor plan, a private courtyard, farmers porch and screened in porch. Enjoy one floor living with primary bedroom, guest room, 2 full baths and den/office all conveniently located on the first floor. A walkout lower level with windows lends for great storage or option to finish later for additional living space. Enjoy the luxury of new construction and condominium living including all of the Pinehills amenities, as well as the Ridge amenities with Meeting House, bocce courts and heated pool. Selections have been made by our award winning design team! Call to schedule an appointment. After all, nothing to do but happily move in!

16 Firefly Point Unit 16, Plymouth

$850,370

2 Beds ⋅ 2 Baths ⋅ 73555068 MLS

PINEHILLS --- LAST HOME AVAILABLE IN OUTLOOK EAST ! FRESCO 2 currently being built ,ANTICIPATED LATE FALL 2026 MOVE IN. $65,000 of selected options applied at no cost to buyer. Located high on the Ridge with wooded views, this designer home will not disappoint. This 2-bedroom, 2 full bath, condominium boasts a spacious floor plan, a private courtyard, farmers porch and open back deck. Enjoy one floor living with primary bedroom, guest room, 2 full baths and den/ office room all conveniently located on the first floor. . Enjoy the luxury of new construction and condominium living in a completed neighborhood that includes all the Pinehills amenities as well as the Ridge amenities with Meeting House, bocce courts and salt water heated pool. Call to schedule an appointment .

73 Outlook East Unit 73, Plymouth

$721,050

2 Beds ⋅ 3 Baths ⋅ 73554408 MLS

Stunning and sunny 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

$1,200,000

73554389 MLS

Pondfront retreat setting estate totaling 10.45 acres of land consisting of 3.15 acre kettle pond - Cotton Pond is approx 20 +/ - feet deep with 7.3 acres surrounding. Bordered by protective conservation (WildlandsTrust) & Town of Plymouth land. Frontage on Historic Old Sandwich Rd & Ship Pond Rd. Property has been approved & registered for 3 total Pondfront lots. Seasonal dock & floating dock included. One lot consists of the 944 sq ft year round rustic vibe ranch w/ panoramic views, spacious living room w/ wood stove, 2 bedrooms w/ closets, small study, den, laundry area w/ pantry & built- ins, full bath, open galley kitchen, 3 season porch w/ walls of glass to maximize the views. 2 storage sheds w/ electricity. Updates include - electrical 2021, gas stove, whole house propane generator, 2 mini split HVAC, hot water tanks, roof 2018. Rare property with various uses, serene estate, family compound w/ 3 houses, investment. Nature lovers paradise, kayak, fish from your private beach.

1029 Old Sandwich Rd, Plymouth

$1,200,000

2 Beds ⋅ 1 Baths ⋅ 73554387 MLS

1029 Old Sandwich Rd, Plymouth

$989,000

3 Beds ⋅ 4 Baths ⋅ 73554084 MLS ⋅ ["Winslowe's View"] BLDG.

Stunning golf views from this popular "C" model home in Winslowe's View at The Pinehills. This home is extra special with 2 private outdoor areas to enjoy. Tastefully done with hardwood floors, cathedral ceilings, built-ins, 2 gas fireplaces, formal dining room and a spectacular space for an office right off the foyer. Lovely dine-in kitchen with gas stovetop, wall oven, built in desk in kitchen nook and slider to lovely and relaxing screened porch and deck with access to patio overlooking sunny golf course. First floor primary suite with walk-in closets, ensuite with double vanities, soaking tub and shower. Grand staircase from the foyer to second floor with a guest bedroom and an office with a closet and full bath. Walk-out lower level complete with entertainment in mind; a bonus room has sliders with access to exterior. Bedroom or crafting/exercise room & full bath. Located within walking distance to pool & pickleball courts & all the amenities of Winslow's View & Stonebridge Club.

17 Ludlow Trail Unit 17, Plymouth

$889,000

3 Beds ⋅ 3 Baths ⋅ 73553543 MLS ⋅ ['Seton Highlands'] BLDG.

Welcome to 17 Aberdeen, where a carefree lifestyle begins in the highly sought-after Seton Highlands 55+ neighborhood of The Pinehills. Step onto your private porch and into this gorgeous, sun-filled, freestanding "Stirling" model home, beautifully designed with all your primary living needs on the first level. A grand two story foyer and gleaming hardwood floors immediately impress, flowing seamlessly into the spacious open floor plan. The gourmet kitchen features beautiful woodgrain maple cabinets, a large island, storage pantry, updated quartz countertops and newer appliances. It opens effortlessly into an eat-in dining area and an impressive, living room boasting soaring cathedral ceilings, custom built-ins, shiplap accent wall and a cozy gas fireplace. A quaint adjacent den offers the perfect retreat for relaxing. The luxurious first floor primary suite is a private sanctuary featuring a walk-in closet with custom shelving, and a spa-like en-suite bath complete with a soaking tub and a beautifully tiled shower stall. Upstairs, a versatile open loft workspace leads to a second bedroom, a full bath, a third bedroom with vaulted ceilings, and a massive bonus room offering endless possibilities for a media room, gym, guest or hobby space. Outside, a large, freshly painted private deck overlooks a serene backdrop, making it the perfect spot for your morning coffee or entertaining friends and family. Move right into this meticulously maintained property and start enjoying the vibrant Pinehills lifestyle today!

17 Aberdeen Unit 17, Plymouth

$879,000

2 Beds ⋅ 3 Baths ⋅ 73552196 MLS ⋅ ["Winslowe's View"] BLDG.

You have been waiting for this U style floor plan in the Winslowe's View neighborhood in the award winning Pinehills. In the last 6 months 4 U style floor plans have sold and a 5th one is under agreement. Flow of the floor plan makes for easy living. This location comes w/an unobstructed- 180 degree view of golf. A DOUBLE fairway view of the Jones 15th & the Jones 12th. Golf cart path on the far side. Natural beauty on the outside & light, bright & airy on the inside. Natural light streams into the main living area through 2 skylights in the living room & 6 windows in the dining area. First floor primary suite w/separate vanities, soaking tub, step in shower. View of a private garden w/a blue door from your bedroom window. Very private. Bay window area in your kitchen makes the ideal breakfast nook& kitchen cabinets complete with pull outs. Den/ library with fireplace. Perfect spot for a good book. Second floor bedroom w/hardwood, bath & loft. New HVAC 2023. Gas fitting for grill.

70 Benjamins Gate Unit 70, Plymouth

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