Pinehills Homes for Sale

Pinehills Homes for Sale

Welcome to Pinehills, a vibrant and picturesque community nestled in the heart of Plymouth, Massachusetts. Known for its stunning natural landscapes and a warm, welcoming atmosphere, Pinehills offers an unparalleled lifestyle that seamlessly blends the tranquility of suburban living with the convenience of modern amenities.

This beautifully designed community is surrounded by lush woodlands, rolling hills, and scenic golf courses, making it a haven for outdoor enthusiasts. Residents can enjoy miles of walking trails, parks, and recreational facilities, fostering an active and healthy lifestyle. Pinehills is also conveniently located just a short drive from the historic charm of downtown Plymouth, where you can explore quaint shops, delightful eateries, and rich cultural landmarks.

For those looking to make Pinehills their home, a diverse array of homes for sale awaits you. From elegant single-family residences to low-maintenance townhomes, there’s a perfect fit for every lifestyle and budget. Many properties feature modern designs, spacious layouts, and high-end finishes, ensuring comfort and style. The community prioritizes sustainability, with energy-efficient homes and green spaces that enhance the quality of life.

Pinehills is not just a place to live; it’s a community where neighbors become friends, and lifelong memories are made. Whether you’re seeking a peaceful retreat or an active lifestyle, Pinehills offers the perfect backdrop for your next chapter. Explore the homes for sale today and discover the charm and beauty that await you in this exceptional community!

Newest Pinehills Homes for Sale

$739,900
2 Beds ⋅ 3 Baths ⋅ 73565766 MLS
Beautiful "Binnacle" floor plan in the Boatwright's Loop neighborhood in the awarding winning Pinehills. "Boatright" (often spelled "Boatwright") is an English occupational surname and noun that means a boat builder or ship’s carpenter; pretty cool name for a street in Plymouth! The design element captures the coastal vibe of Plymouth perfectly. The design also captures every square inch of living space for when the college kids are home for the summer. Expands perfectly while you are enjoying each others company. 3 floors of living space. Main floor - open airy concept of OPEN floor plan w/a zig zag wall of glass allowing the light to stream in. Same main floor - has primary suite AND laundry all in the same area. Laundry becomes a breeze. Second floor has ideal set up with 2nd bedroom and bath w/bonus loft area! Large bonus room in the finished lower level. For summertime entertainment - take in the night air with the shops and entertainment in the Village Green.

53 Boatwrights Loop, Plymouth
$739,000
2 Beds ⋅ 3 Baths ⋅ 73563701 MLS
Three levels of living. Close to the Village. Beautiful lighting package in this Halyard style floor plan in the popular Symington Woods neighborhood at The Pinehills. Just through your front door and up the stairs is a wonderfully designed open floor plan that has you happy to be at home. Great kitchen, gorgeous counter tops. Kitchen island with kitchen sink where you overlook the heart of your home. Sit on your covered balcony and hear the birds and feel the breezes that are part of the wonderful summer season. Primary bedroom with custom closet and beautifully appointed primary bath. Second floor has an incredible loft space with two sky lights! Spacious second bedroom and separate bath (with a deep tub) are perfectly private for family and friends. Amazing storage room. Bonus room in the lower level can be a second gathering space, office or exercise room. HOA amenities include the Stonebridge Club with clay tennis courts, outdoor swimming pool and numerous groups and activities.

4 Hawthorne, Plymouth
$1,295,000
3 Beds ⋅ 3 Baths ⋅ 73562389 MLS
Two story, picture perfect "Bridleridge" style home in the sought-after Vista Point community in The Pinehills. This home captivates you both inside and out. Enter through the dramatic two-story foyer. There is a front office, a guest bedroom, a full bath & laundry room, all tastefully appointed. Beautifully designed kitchen w/custom cabinets, large island, stove top hood vented to outside and tiled backsplash, nook with slider to the spectacular outdoors w/extended deck and patio with a built-in firepit. A two-story living room has plenty of space for extended family gatherings around the floor to ceiling fireplace & opens to the dining room. The primary bedroom has 2 walk-in closets & a large primary bathroom. The second story has a generous sized family room w/ full bath, guest bedroom & exercise room. A walkout unfinished basement has a workshop & a slider to backyard. This home has it all! The neighborhood HOA includes lawn mowing, snow and trash removal, a club house with an exercise facility, function rooms, outdoor pool, firepit and bocce.

70 Woody Nook, Plymouth
$747,000
2 Beds ⋅ 3 Baths ⋅ 73562184 MLS
Pickleball? Pinehills Village Green? Downtown Plymouth waterfront? Make yourself a coffee in your sunny and white kitchen, then head to the three-season porch to check the weather and plan your day. Living in the Great Island (55+) neighborhood of The Pinehills means options like these are just the beginning. You’ll feel right at home in this beautiful, move-in-ready “Milton” style home, filled with natural light and warmth. Impeccably maintained by the original owner, it offers a two-car garage and many upgraded features that set it apart: extra windows throughout, including transoms and a bay window, high ceilings, hardwood floors, an updated kitchen with stainless steel appliances, a laundry room with pedestals, irrigation, an upstairs flex space with a window seat, and a new heat pump/AC condenser (2025). The open floor plan offers one-level living with a first-floor ensuite primary, plus a spacious second level with a bedroom, Jack-and-Jill bath, open living space, and a bonus area suited to a variety of uses. A first-floor den/office adds even more flexibility. There is plenty of room for family and friends! The large open dining room is perfect for holidays or welcoming new neighbors over for dinner. Set on a quiet street in an excellent location with a wooded back yard, it’s just a quick walk to the Overlook Clubhouse, with amenities including an indoor pool, gym, billiards, social spaces, bocce, tennis, and pickleball. Come see this home for yourself — and discover why the Great Island community is so popular.

9 Canoe Lndg, Plymouth
$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
$725,000
2 Beds ⋅ 3 Baths ⋅ 73561911 MLS
Tucked away on a quiet street. The location matches the street name. This Milton style floor plan is single family attached home located in the fabulous 55+ Great Island neighborhood in the award winning Pinehills. Distinguished dining room with crown molding and picture frame wainscoting sets the stage for casual meals with family or perhaps a more formal affair where the evening calls for dinner by candlelight. Gas fireplace in your adjacent living room could also add to the ambience of the dinner party. Living room with plenty of room for all on movie night. Delightful eat in kitchen with big window, beautiful kitchen cabinets and granite counter tops. First floor office/den, first floor laundry and first floor 1/2 bath. Primary ensuite with double vanity, soaking tub and step in shower with private loo. Second floor with ensuite guest bedroom and bath with large family room and enough space for additional office if needed. Overlook Clubhouse offers an indoor pool, tennis/pickle ball, water aerobics and more. Dedicated activity director.

6 Autumn Glen, Plymouth
$1,024,000
2 Beds ⋅ 2 Baths ⋅ 73561850 MLS
Don't miss the last Lexington Cottage style one level home at Owls Nest! This popular home features an open layout connecting the kitchen, casual dining, and great room, soaring 12' ceilings, a gas fireplace and sliding glass door leading to the large screened porch and stairs to the rear yard. The generous primary bedroom suite includes a light filled bathroom with a large walk in shower, dual sink vanity, and walk in closet. Guests will enjoy a secondary bedroom with a walk in closet and bathroom, this home also includes a flex room\den, dedicated work space, mud room and main floor laundry room. Additional features of this home include an unfinished basement. Additional features include Kitchen Aid appliances, Quartz counter tops, hardwood floors, two car garage, private clubhouse, pool, lawn care, snow removal and more.

23 Loons Call Unit 132, Plymouth
$1,075,000
3 Beds ⋅ 3 Baths ⋅ 73561329 MLS
Welcome to 51 Forest Edge, ideally situated in one of The Pinehills’ most desirable neighborhoods, where beautifully landscaped streets, miles of scenic walking trails, and an exceptional sense of community create a lifestyle unlike any other. Just one mile from the Village Green, this beautifully designed 3-bedroom, 3-bath home offers the perfect blend of comfort, privacy, and effortless first-floor living. Step inside to a bright, open floor plan highlighted by hardwood floors, impressive 11’ ceilings, a center fireplace, custom built-ins, and a wall of windows overlooking peaceful, wooded views. The elegant dining area flows seamlessly into the well-appointed kitchen featuring quality appliances and a spacious center island—perfect for gathering and entertaining. The first-floor primary suite offers a private retreat with en-suite bath and two walk-in closets. A second main-level bedroom provides wonderful flexibility for guests, a den, or home office. The professionally finished walk-out lower level seamlessly expands the living space with a generous family room, third bedroom, full bath, office, workout area, and wet bar—ideal for extended family, overnight guests or simply additional space to relax and entertain. Outdoor living is equally inviting with a welcoming covered front porch, expansive composite deck, and private fenced backyard surrounded by natural beauty. Enjoy the convenience of being within walking distance to the Stonebridge Club with its pool, tennis courts, and clubhouses, while The Pinehills Village Green, restaurants, shops, golf, and miles of trails are just minutes away. Easy access to Route 3, historic downtown Plymouth, beaches, and Cape Cod completes the package. 51 Forest Edge offers the space, privacy, flexibility, and lifestyle that make The Pinehills such an extraordinary place to come home to!

51 Forest Edge, Plymouth
$1,999,000
3 Beds ⋅ 5 Baths ⋅ 73560572 MLS
MacKenzie custom-built single-family home on double lot with views of Jones Pond (#8 hole) and walkable to the Village Green. Many unique features w/comforts galore. Three floors allow for everyday life, special guests and party time. Wood floors throughout and composite flooring on the finished lower level. Large windows throughout the home lets incredible light into every room. All white cabinets and appliances gives the large chef's kitchen a clean sleek appeal. 2 large guest rooms with individual en suites on the second level with a large loft gives you and your guests plenty of space to unwind.The main level is for enjoying your family and friends with a large living room and dining room adjacent. Plus a cozy breakfast nook. Two dishwashers makes any clean up easy. The primary bedroom with two walk-in closets allows for maximum comfort to the home's owners. The en suite is magnificent with a large shower, soaker tub and double sinks. The washer and dryer are housed on the first floor for easy access. A Four-Season room allows for true chill time. The outside large deck is yours for grilling along with a built in fire pit for stargazing nights, and cocktails. You'll hear the gentle tumble of the fountain on Jones Pond. The lower level has 2 large offices along with a billiards room. The main attraction in the lower level is a full bar with refrigerator, dishwasher and a large wine rack. Talk about Super Bowl parties- your home will be the place to be! Huge screen TV with plenty of seating for all is included. Lastly check out the utility room with racks that allows for incredible storage. You will fall in love with this house.

25 Painted Cottage, Plymouth
$850,000
3 Beds ⋅ 3 Baths ⋅ 73560230 MLS
Very unique location on the corner of Shinglewood and Clam Pudding (and yes there really is a recipe for clam pudding). Welcome to this beautiful and highly desirable, "Laurel" style floor plan located in the 55+ Del Webb neighborhood, Great Island, in the award winning Pinehills. The two story foyer and the two story family room are just two of the reasons to fall in love with the flow of this plan. Another reason is the 30 x 10 foot back deck with awning that just seems to beckon you to be outside, (napping optional). Hardwood floors on the main level. Office with built in book cases on the main level. Primary bedroom on the main level with wall to wall carpeting, tray ceiling, primary bath including double vanity and walk in closet with closet system in place. Expanded kitchen with 42" cherry cabinets, granite countertops and double wall ovens will have you dining in more than dining out. Natural sunlight streams through the two, second story windows in the family room filling your loft area with natural light. Two bedrooms, and a full bath complete the upstairs. Hunter Douglas silhouette blinds, plantation shutters, humidifier, Tankless hot water. heater, irrigation. Close to the fabulous Overlook Clubhouse with tennis/pickleball, indoor swimming pool, exercise facilities, card room, craft room, billiards room and more.

66 Clam Pudding, Plymouth
$761,900
2 Beds ⋅ 3 Baths ⋅ 73560086 MLS
NEW CONSTRUCTION – Ready for October delivery! Brand New Floor Plans at Symington Woods. The beautifully designed "Tidewater" floor plan features an open-concept 1st floor layout perfect for modern living. The spacious kitchen offers a large pantry and a seamless flow into the dining and living areas, ideal for entertaining. Step out from the living room onto a private deck with peaceful treetop views. With 3 spacious bedrooms and 2.5 baths, this home combines style, comfort, and functionality. Tons of storage in the unfinished walk-out basement or huge potential for more living space! Don’t miss the opportunity to own this exceptional new construction home with a one year builder warranty. Proudly built by Whitman Homes.

14 Snapdragon, Plymouth
$1,049,000
3 Beds ⋅ 3 Baths ⋅ 73558855 MLS
One of the final WInchester homes at Owls Nest. Move in late winter 2027. This brand new two story Winchester style home features three bedrooms, three bathrooms and a bright unfinished walkout basement. From the two story foyer to the large kitchen with center island, open to the fireplaced great room which includes 18' ceilings, gas fireplace, hardwood flooring and expansive windows. Step through a glass door to the included deck with stairs to the rear yard. The luxurious first floor primary bedroom suite includes a light filled bathroom with a large walk in shower, marble seat, dual sink vanity, linen and walk in closets. Also located on the main level, a secondary bedroom, private office, and laundry. The second floor features privacy for guests with an additional bedroom, bathroom, and loft. Located within walking distance to the community clubhouse and pool.

16 Owls Nest Unit 7, Plymouth
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