Pinehills Homes for Sale

Welcome to Pinehills, a picturesque community nestled in the heart of Plymouth, Massachusetts. This vibrant neighborhood offers a unique blend of natural beauty, modern amenities, and a rich historical backdrop, making it an ideal place for families, retirees, and everyone in between.

Pinehills is renowned for its stunning landscapes, featuring rolling hills, lush greenery, and scenic walking trails that invite residents to embrace the great outdoors. With its close proximity to the Atlantic coast, you can enjoy leisurely days at nearby beaches or indulge in water sports on the serene Plymouth Harbor. The area is steeped in history, with attractions like the iconic Plymouth Rock and the historic Mayflower II just a short drive away, allowing you to immerse yourself in the rich heritage of America.

When it comes to homes for sale in Pinehills, you'll find a diverse selection that caters to various lifestyles and preferences. From charming single-family homes to luxurious townhouses and modern condominiums, the real estate options are as varied as the residents themselves. Many properties boast elegant designs, spacious layouts, and state-of-the-art amenities, ensuring comfort and convenience for every homeowner.

Additionally, Pinehills is home to top-rated schools, vibrant shopping centers, and delightful dining options, creating a sense of community that is both welcoming and engaging. Whether you are looking to settle down in a tranquil neighborhood or seeking an active lifestyle, Pinehills is the perfect place to call home. Explore the available homes for sale today and discover your dream residence in this enchanting corner of Massachusetts!

Newest Pinehills Homes for Sale

$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

$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

2 Beds ⋅ 1 Baths ⋅ 73554387 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

$749,900

2 Beds ⋅ 3 Baths ⋅ 73552193 MLS

Everything you wanted on your new home wish list and more. 107 Boatwright’s Loop is a one-of-a-kind townhome in The Pinehills. It has been owned by one family who have cared for it meticulously. The townhome walls have been freshly painted & hardwood floors refinished. Air Duct System & windows inside and out professionally cleaned. “CLIMATE CHANGE” compatible! Solar Panels installed in 2023. Heat Pump installed in 2024. Back Up Battery System was constructed in the garage in 2025. The garage has a 240 line for charging an electric or dual hybrid automobile. Leaf Filter System Gutter installed in 2026. For the professional working at home, there is an incredible home office in the lower-level w/built-in bookshelves. Garage floor freshly coated w/an epoxy resin 2026. The townhouse looks out at the garden island between Mainstone Blvd & Boatwright’s Loop maintained by the Beautification Committee. Enjoy sunset views from your balcony.

107 Boatwrights Loop, Plymouth

$1,325,000

3 Beds ⋅ 5 Baths ⋅ 73549068 MLS

Distinguished Thorndike-built home with sweeping views of the Nicklaus 5th hole in The Pinehills. Professionally landscaped with mature plantings, a stone walkway, patio, and granite steps. Renovated gourmet kitchen features premium cabinetry, upgraded stainless steel appliances, and an eat-in area opening to a sun-filled oversized screened porch. Vaulted foyer leads to a dramatic living room with gas fireplace and custom built-ins, formal dining room, and den/office. First-floor primary suite offers golf course views and a renovated spa bath with radiant heated floors. Upstairs are two bedrooms, a full bath, loft, and bonus room with its own bath. New walkout lower level includes a spacious family/game room. Recent updates include the kitchen, primary bath, HVAC, hot water heater, carpeting, custom window treatments, and landscaping. HOA includes Stonebridge Club access.

20 Wickertree, Plymouth

$1,145,000

2 Beds ⋅ 3 Baths ⋅ 73548775 MLS

Prime location with EPIC sunset views at this expansive 2 bed, 3 bath move-in-ready "Westford" style home in Owls Nest neighborhood at The Pinehills. This house feels like home. Neighborhood construction is nearly complete. Finished with the finest options and highest level of design, no expense was spared. Main floor has 10' ceilings, hardwood floors and custom window treatments, 2 bedrooms, 2 full bathrooms, office, den, screened-in porch (with incredible sunset views), kitchen, living room and dining room with beautiful gas fireplace, laundry room with built-ins, and pantry- all with access to two-car garage. Backyard and patio access via staircase from screened-in porch. Finished lower level has major bonus space with full bath, high ceilings, luxury vinyl planking, and slider leading to the patio and backyard. Spectacular Owls Nest neighborhood amenities include pool, clubhouse, fitness, and more.

31 Kestrel Heights, Plymouth

$949,000

2 Beds ⋅ 2 Baths ⋅ 73548560 MLS

Experience the effortless flow of this "Tradition Heritage" style home, a short drive from the Village Green, shops, and restaurants. Designed for easy living with everything you need on one floor. Enter the front door and find a bright study with coffered ceilings behind French doors—would also make a perfect den. The formal dining room with dry bar makes a grand impression with floor-to-ceiling pillars, a tray ceiling, and plantation shutters. The expansive living room features a cozy fireplace and leads to a gourmet kitchen, featuring gleaming cabinets, granite counters, and high-end stainless-steel appliances. Just off the kitchen, sliders lead to a private covered deck overlooking a serene, wooded backdrop with stone wall and patio area. Retreat to the primary suite, a true sanctuary boasting a large walk-in closet and a spa-like ensuite bath. A sunny second bedroom provides a comfortable space for guests. Come experience an elevated single level lifestyle in The Pinehills!

23 Woodsong, Plymouth

$949,000

3 Beds ⋅ 4 Baths ⋅ 73547910 MLS

Showings begin Friday, July 17, 4PM! Welcome to your private oasis in America's Hometown on the South Shore, conveniently located near all the amenities + attractions The Pinehills & Plymouth offer. From elite golf courses, sandy beaches, restaurants/bars, shops, gyms, and nature trails to easy access to Boston, Cape Cod, and the Islands - the PH location, lifestyle, and convenience can't be beat! This 23 yr old home with 2-car garage has GREAT bones! With 2,998 sqft, this home lives like a 4-bed with 3.5 baths across 3 spacious levels. Interior features include a first-floor primary suite, 3-zone central A/C, 2-zone natural gas forced hot air heat, gas fireplace, hardwood floors throughout most of the main level, chef’s kitchen, and Hunter Douglas window treatments. Exterior features include private lot w/ mature landscaping, Trex decks, fenced yard with patio, irrigation, and granite steps to lush backyard. At $949,000, this is the best-priced home in The Pinehills & the South Shore.

30 Barnswallow Ln, Plymouth

$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

$745,000

2 Beds ⋅ 3 Baths ⋅ 73547439 MLS

Ideal first-floor living in this "Milton" floor plan in 55+ Great Island in The Pinehills. A bright kitchen with a cozy breakfast nook flows into an elegant dining area featuring a bay window, crown molding, and picture frame wainscoting. The dining room opens to the living room with gas fireplace, and sliding glass doors lead to a deck with wooded views. Transom windows throughout the dining area, living room, and two-story foyer fill the home with natural light. First-floor primary suite with walk-in closet, double vanity, shower, and tub. Office and laundry also on the first floor. A sweeping staircase leads to a loft/den area, a private second bedroom with bath, and a cozy nook. New HVAC 2022. New hot water heater and washer/dryer 2026. The neighborhood's Overlook Clubhouse offers an indoor pool, tennis, and a dedicated activity director.

28 Cross Wind, Plymouth

$929,000

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

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