Pinehills Real Estate

Welcome to Pinehills, a picturesque community nestled in the heart of Plymouth, Massachusetts. This charming neighborhood is a harmonious blend of natural beauty and modern living, making it a sought-after destination for families, retirees, and everyone in between.

Pinehills is renowned for its stunning landscapes, featuring rolling hills, lush woodlands, and serene ponds that create a tranquil atmosphere. The community is designed around the concept of “living in harmony with nature,” offering residents a peaceful retreat while still being conveniently close to the vibrant culture of Plymouth. With its rich historical significance, Plymouth is just a short drive away, allowing residents to explore iconic landmarks such as Plymouth Rock and the Mayflower.

In Pinehills, you’ll find a diverse range of housing options, from charming cottages to elegant single-family homes, all thoughtfully integrated into the natural surroundings. The community boasts a variety of amenities, including walking trails, golf courses, and recreational facilities, perfect for those who enjoy an active lifestyle. The local shops, restaurants, and community events foster a strong sense of belonging, making it easy to connect with neighbors and build lasting friendships.

Education is a priority in Pinehills, with access to top-rated schools and educational programs that cater to all ages. Whether you’re looking to enjoy a peaceful stroll through scenic parks or engage in the vibrant community life, Pinehills offers a unique blend of tranquility and excitement. Discover your dream home in this idyllic corner of Plymouth, where every day feels like a vacation!

Newest Listings in Pinehills

$1,195,500

3 Beds ⋅ 3 Baths ⋅ 73587897 MLS ⋅ ["Winslowe's View"] BLDG.

This limited "A" style home located in Winslowe's View at The Pinehills affords tons of privacy and overlooks a nice golf view lot with a spacious deck and private front courtyard. This home is perfect for entertaining. With gorgeous hardwood floors, this open floor plan features a large sunlit living room with gas fireplace & custom built-ins and a wall of windows, adjacent dining area, a gracious primary suite with cathedral ceiling, custom built-ins, 3 closets and bath with double vanity tiled shower. The office/guest bedroom overlooks the beautiful courtyard on the first level. The lovely kitchen has light grey cabinets, quartz countertops & beautiful backsplash, built-in oven & stainless-steel appliances, all lower cabinets have custom pullout drawers for storage and accessibility, all new! Dining Room on first floor with French door and full wall of custom built-ins including pullout drawers and cabinets and a wine chiller! The second level has a loft with bookcase built-ins vaulted ceilings & 3 sky lights, third bedroom & full bath. Windows UVA protected. Community pools, tennis & pickle ball courts, exercise, club houses and many activities and clubs to join for a very active lifestyle. This home is in pristine condition!

16 Turner Run Unit 16, Plymouth

$1,040,000

3 Beds ⋅ 3 Baths ⋅ 73587816 MLS ⋅ ['Broadleaf'] BLDG.

Ideally located just steps from the Village Green, Sited on one of the final end locations, this Design Ready Hager style home offers an open-concept layout perfect for everyday living and entertaining. The spacious kitchen features abundant cabinetry, a walk-in pantry, and a large center island overlooking the great room. The sun-filled primary suite includes a generous walk-in closet and a luxurious en suite bath with an oversized shower. A versatile flex room, powder room, and conveniently tucked-away laundry complete the main level. Upstairs, you'll find a cozy loft, second and third bedrooms and full bath. The bright unfinished walkout basement offers future expansion possibilities. Spend hours on the screened porch with open space beyond. Work with our design team and select from today's popular designer features, home technology and more! Broadleaf Residents enjoy access to the Stonebridge Club, featuring a clubhouse, pools, fitness center, and tennis courts.

46 Broadleaf Unit 0032, Plymouth

$1,049,000

3 Beds ⋅ 4 Baths ⋅ 73587520 MLS ⋅ ["Winslowe's View At The Pinehills"] BLDG.

Exceptional End-Unit “C” Model in Winslow’s View at The Pinehills. Enjoy golf-course living in this exceptional 3-bedroom, 3½-bath “C” model end unit overlooking the 13th green of the Nicklaus Course. This private, light-filled home combines a beautiful setting, numerous recent updates, and an easy Pinehills lifestyle. The stunning kitchen, remodeled in 2025, features a fresh, inviting design and abundant storage. The spacious primary suite offers a renovated, spa-like bath, while a stylish floating vanity enhances the powder room. An updated cozy fireplace adds warmth and character to the living space. The oversized deck extends the living space outdoors, with golf-course views and a natural gas line for effortless grilling—perfect for morning coffee, sunset cocktails, or entertaining. Additional improvements include all-new Andersen windows, a new Carrier gas furnace, and Ecobee smart thermostats, enhancing comfort and efficiency while providing peace of mind. Just moments from the pool, clubhouse, tennis, and pickleball, this exceptional end unit offers the ideal balance of privacy at home and connection to all that The Pinehills has to offer.

1 Fletcher Reach Unit 1, Plymouth

$979,000

3 Beds ⋅ 4 Baths ⋅ 73587290 MLS ⋅ ['Broadleaf'] BLDG.

Welcome to Broadleaf in The Pinehills! The thoughtfully designed Davis Manchester is only steps from the vibrant Village Green. An inviting front covered front entry opens to the foyer and a bright office. The spacious open concept kitchen features a large island, casual dining, and flows into the fireplaced great room and large sliding door. The large kitchen is equipped with an oversized island, plenty of counter and cabinet space, and sizable pantry. The sophisticated primary bedroom suite offers dual walk-in closets, and primary bath with a spa-inspired glass-enclosed shower with seat. The second floor offers abundant loft space and features 2 private guest bedrooms and 2 full bathrooms. Choose from todays popular flooring, Tile Cabinetry, Home Technology and More with our design team.Move-in early fall 2027!

26 Broadleaf Unit 0023, Plymouth

$1,008,000

3 Beds ⋅ 4 Baths ⋅ 73587279 MLS ⋅ ['Broadleaf'] BLDG.

Welcome to Broadleaf in The Pinehills! The thoughtfully designed Davis Farmhouse is only steps from the vibrant Village Green. An inviting front covered front entry opens to the foyer and a bright office. The spacious open concept kitchen features a large island, casual dining, and flows into the fireplaced great room and large sliding door with a screened porch beyond. The large kitchen is equipped with an oversized island, plenty of counter and cabinet space, and sizable pantry. The sophisticated primary bedroom suite offers dual walk-in closets, and primary bath with a spa-inspired glass-enclosed shower with seat. The second floor offers abundant loft space and features 2 private guest bedrooms and 2 full bathrooms. Choose from todays popular flooring, tile Cabinetry, home technology with our design team.Move-in early fall 2027!

40 Broadleaf Unit 0029, Plymouth

$1,075,000

3 Beds ⋅ 4 Baths ⋅ 73587245 MLS ⋅ ['Outlook East'] BLDG.

Spectacular Fresco 5 in Outlook East Neighborhood in The Pinehills. An enchanting courtyard with a covered porch leads you to the front door. This open floor plan living space includes a great room with a gas fireplace & custom built-in on either side. An upgraded kitchen with custom cabinets, quartz countertops and a walk-in pantry and a dining area. There is a private primary suite on the first-floor w/the ideal design of custom double vanities & dressing areas highlighted by the custom tiled shower. There is a 2nd bedroom on the first level and a full bath. Guests will be comfortable in the 2nd floor suite complete w/full bath oversized bedroom and a loft. A laundry room with custom cabinets. A back deck for extra space to entertain. There is a finished walk out lower level with a large bonus room and a cedar closet plus an unfinished area for expansion and storage. There are hardwood floors throughout the home. The HOA includes a pool and clubhouse and exercise in the Veridian neighborhood and the Stonebridge Club with tennis courts, exercise, additional pool and an abundance of clubs to join. All exterior maintenance and snow removal included in the HOA. Come and enjoy the lifestyle.

10 Outlook East Unit 10, Plymouth

$1,999,000

3 Beds ⋅ 5 Baths ⋅ 73586984 MLS

FURNISHED! 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 let's incredible light into every room. All white cabinets and appliances give the large chef's kitchen a clean sleek appeal. 2 large guest rooms with individual ensuites 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 make any clean up easy. The primary bedroom with two walk-in closets allows for maximum comfort to the home's owners. The ensuite 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

$685,000

2 Beds ⋅ 3 Baths ⋅ 73586926 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

$979,000

3 Beds ⋅ 4 Baths ⋅ 73586879 MLS

15 Mint Sprig, Plymouth

$1,045,000

3 Beds ⋅ 3 Baths ⋅ 73586641 MLS

Welcome to 28 Barnswallow, a stunning Bradford-style residence tucked away on a quiet, but convenient lot. Perfectly positioned near the Rye Tavern and the community amenities, this home strikes the ideal balance between design and comfort. When you step into the home you will instantly notice the freshly painted interior and the gleaming hardwood floors. From the foyer, you will notice a formal dining room to one side and a living area, which can also be used as a home office to the other side. At the back of the home, you will find a beautiful kitchen with walk in pantry that seamlessly flows to the family room with high ceilings, a fireplace, and the eat in dining area. Off the family room there is a large deck that overlooks the serene backyard with mature plantings. The primary suite finishes off the main level with a large walk in closet and full ensuite bath that has a soaking tub, separate shower, radiant heat, and large vanity. Upstairs you will find a large loft area and two well-appointed guest rooms, perfect for visitors. There is also a beautifully remodeled bathroom that will make guests feel right at home. The walk out lower level can easily be finished for those who are looking for more space. You will be impressed by the beautifully manicured grounds, custom landscape lighting, generator, and solar panels, which are owned by the seller and allows you to enjoy significant utility savings. Life at The Pinehills feels like a getaway, where days are defined by rounds of golf, tennis, afternoons at the Stonebridge Club, and dinners at the Village Green. Visit today and envision the life you imagined in this home.

28 Barnswallow, Plymouth

$795,000

2 Beds ⋅ 2 Baths ⋅ 73586237 MLS

Simply Fabulous "Franklin" floor plan located in the award winning Pinehills master planned community in the Del Webb 55+ Great Island neighborhood. Enjoy the breeze from your EXCEPTIONAL custom screened porch with wooded views. Truly one-of-a-kind and will soon be your favorite place to be. The Franklin floor plan is very popular because of its ideal first floor living. Primary bath with gorgeous tiled shower, double vanity and large walk in closet. Primary bedroom with tray ceiling and lovely wooded view. Second bedroom and bath on the main level. Extended cabinetry in your kitchen with granite counter tops and delightful breakfast nook with bay window and views of mother nature. Walk out finished lower level with large bonus room and office space. There is a second layer of outdoor living - the deck - with stairs that take you down to your back yard. The Overlook Clubhouse has a dedicated activity director, indoor pool, tennis.

14 Horizon, Plymouth

$1,550,000

3 Beds ⋅ 4 Baths ⋅ 73585868 MLS

This beautiful one-of-a-kind Toll Brothers "Bedford" style home in The Pinehills has an open concept living floorplan. The features include a dramatic living room with 22-foot walls of glass windows to view the great outdoors. This home has full solar with back up battery for solar panels. EV charger ready in garage. Lutron power shades throughout. Expanded deck, extra-large garage, 4 full bathrooms. Hardwood flooring. Gourmet Kitchen with JennAir appliances and custom cabinets with glass encasements to the ceiling, quartz countertops with a sizeable center island. Retreat to the first-floor primary suite with spa-like shower, double sinks, large walk-in closet and views of the woods. Additional guest bedroom and full bath located on the first floor, office with custom bookshelves. A separate dining room to entertain your guests. Upstairs has room for everyone to enjoy with large great room with vista views of trees and sunsets, another guest bedroom and an additional full bath. A bonus room for crafting/or a quiet study. A finished lower level with an exercise room, full bath and a game room/entertainment space to enjoy a movie with room darkening shades or play a game at the card table, enjoy a cocktail at the bar that opens up to the patio in the private back yard. The HOA includes lawn mowing, a neighborhood clubhouse with a kitchenette, function room, game room and exercise room with outdoor pool. The HOA includes Stonebridge Club: pool, tennis, function and exercise rooms and an abundance of clubs.

17 Kestrel Heights, Plymouth

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .