Chiltonville Real Estate

Welcome to Chiltonville, a hidden gem nestled in the picturesque town of Plymouth, Massachusetts. This charming neighborhood exudes a unique blend of historical charm and modern convenience, making it an ideal place for families, retirees, and everyone in between.

Chiltonville is characterized by its serene, tree-lined streets and a tight-knit community atmosphere. The area is rich in history, with many homes reflecting the architectural styles of the 18th and 19th centuries. Residents take pride in maintaining the character of the neighborhood, creating a warm and inviting environment for all who live here.

Nature enthusiasts will find plenty to love about Chiltonville. The region is surrounded by stunning landscapes, including the nearby Myles Standish State Forest, which offers miles of hiking and biking trails, as well as opportunities for fishing and camping. The scenic shores of Plymouth Harbor are just a short drive away, perfect for those who enjoy beach outings or sunset strolls along the coastline.

Chiltonville is also conveniently located near Plymouth's vibrant downtown area, where you can explore an array of shops, restaurants, and cultural attractions. The historic Plymouth Rock and the Mayflower II are just a stone's throw away, providing a glimpse into the rich heritage of this iconic town.

With its perfect blend of tranquility, community spirit, and access to both nature and history, Chiltonville is not just a place to live, but a lifestyle to embrace. Discover your dream home in this enchanting neighborhood and experience all that Chiltonville has to offer!

Newest Listings in Chiltonville

$885,000

5 Beds ⋅ 3 Baths ⋅ 73573671 MLS

Welcome to this exceptional 5-bedroom, 2.5-bath home ideally situated in the highly desirable Chiltonville neighborhood of Plymouth. Perched atop a gentle hill, this meticulously maintained property offers an ideal combination of space, privacy, and seamless indoor-outdoor living. Inside, the spacious floor plan features a generous living room with a double-sided fireplace, a large, fully appointed eat-in kitchen, and a separate dining area, all enhanced by high beamed and vaulted ceilings, abundant storage, and thoughtful details throughout. The main level offers a spacious primary suite with en-suite bath, three additional bedrooms, and a second full bathroom. The lower level provides exceptional flexibility with an additional bedroom, living area, fireplace and bathroom—ideal for guests, or multi-generational living. A two-car garage provides added convenience and storage. Outside, the expansive, level backyard is a private oasis, complete with an inviting pool, oversized deck, storage shed, and direct abutment to conservation land. This peaceful setting is perfect for entertaining, relaxing, and enjoying the best of outdoor living. Ideally located with easy access to major highways, Beth Israel Deaconess Hospital–Plymouth, shopping, restaurants, and historic Downtown Plymouth, this special property offers the perfect blend of tranquility and convenience. A rare opportunity to enjoy the space, privacy, and sought-after setting of Chiltonville.

21 Woodvale Ave, Plymouth

$1,089,000

2 Beds ⋅ 3 Baths ⋅ 73572199 MLS ⋅ ['Saltash At Chiltonville'] BLDG.

Saltash at Chiltonville – Exceptional 55+ Active Living Community set on 25 acres of wooded, deed-restricted land ensuring no future development. This boutique neighborhood of only 48 duplex-style condominiums was inspired by the area’s most beloved historic architecture featuring four reimagined classic Chiltonville home styles ~ Greek Revival, Cottage, Half Cape & Half Colonial ranging from approximately 2,300 to 2,700 sq. ft. with additional bonus room space available, two-car garages & full basements. Saltash offers the finest in energy-efficient construction, timeless design, and an uncompromising level of craftsmanship. Every home features a first-floor owner’s suite, private yard and patio, access to premium community amenities including a clubhouse, inground pool, firepit & fitness center, Just mins from downtown Plymouth / Waterfront. Unit 22 is a Greek Revival style home to be built on a walk out lot. 60% sold. Open House being held at Model unit # 14 Half Colonial ready for occupancy .

46 Sandwich Road Unit 22, Plymouth

$829,000

4 Beds ⋅ 2 Baths ⋅ 73567819 MLS

Located in Plymouth’s desirable Chiltonville Village, loved by the same family over the years, this beautiful Colonial-style home is tucked back from the street, offering a peaceful setting. The heart of the home is the open-concept kitchen and cathedral-ceiling family room, designed for gathering and everyday living. The family room features a Vermont Castings propane stove and overlooks the backyard, creating a warm and inviting space. The kitchen offers solid cabinetry, breakfast bar, pantry, and everyday dining area. Beautiful wide-pine flooring in the dining room and living room sets the tone for this unique home. Upstairs, you’ll find three spacious bedrooms plus a cozy loft/bonus area, offering plenty of room. First-floor bed or office, 2 full baths, 1st-floor laundry, ample closet space, and a one-car garage with huge storage room complete this space. Enjoy the outdoors from the oversized deck with wooded surroundings, or relax beside the in-ground pool. The private setting provides a wonderful sense of tranquility while remaining just minutes from downtown Plymouth, area beaches, shopping, dining, highways, and local favorites such as Bramhall’s Country Store. A wonderful opportunity to enjoy the best of Chiltonville...privacy, character, space, and convenience all in one special property!

43 E Russell Mills Rd, Plymouth

$1,970,000

5 Beds ⋅ 4 Baths ⋅ 73563892 MLS

Back on due to buyer's financing...Gracefully poised along coveted Warren Avenue, this exquisitely renovated 1900 Queen Anne Shingle Style residence offers a rare blend of historic character and modern luxury—just moments from Plymouth Harbor, Long Beach, and all that downtown has to offer. Enjoy seasonal ocean and harbor views from the expansive front porch—perfectly suited for morning coffee or evening unwinding. Lovingly redesigned starting in 2023, the home was reimagined with the collaborations of Home Design Studio and Knox Interior; thoughtfully transforming its flow for modern living while preserving the architectural integrity and distinctive character of its origins. Rich in detail and exceptional craftsmanship, the residence spans over 4,600 square feet and features five bedrooms and four full baths, including two ensuite primary retreats—offering remarkable flexibility for multigenerational living, extended family, or hosting with ease. Sunlight streams through the home, illuminating custom millwork, built-ins, and carefully curated finishes throughout. At the heart of the home, the bespoke kitchen balances beautiful design with exceptional functionality, creating a natural gathering place for both everyday living and memorable entertaining. A first-floor bedroom blends seamlessly into the four season room, complemented by a full bath providing additional living flexibility, while the second floor primary suite is a sanctuary unto itself—an exquisitely appointed private oasis. The expansive Ipe deck becomes a natural extension of the home, thoughtfully arranged for outdoor living and entertaining with a spa, generous sectional seating, dining area, grilling space, and pergola. Sliding doors and additional access from the home create an effortless connection between indoors and out, while steps lead to the surrounding professionally kept grounds. A home where every detail has been intentional - offering timeless elegance, modern comfort, and the unmistakable character of quintessential New England coastal living. Be sure to watch the lifestyle video

65 Warren Ave, Plymouth

$1,250,000

4 Beds ⋅ 3 Baths ⋅ 73560123 MLS

Discover a rare opportunity to own a one-of-a-kind estate where timeless architecture, expansive grounds, and exceptional outdoor living come together. Designed by renowned architect Royal Barry Wills, this distinctive 2,392-square-foot residence is gracefully set on 2.52 private acres, offering the perfect balance of character, comfort, and space to grow.Inside, the home features 4 bedrooms and 2.5 bathrooms, with thoughtfully designed living spaces that reflect the warmth and craftsmanship synonymous with Royal Barry Wills' celebrated designs. Large windows invite natural light throughout, while the home's classic layout creates an inviting atmosphere for both everyday living and entertaining. Bring your interior design eye to this classic home.Step outside to your own private retreat. Spend summer days relaxing by the inground pool, surrounded by mature gardens that provide beauty, privacy, and seasonal color. The expansive grounds also feature a basketball hoop, tool shed, and abundant open space for recreation, gardening, or future possibilities.

75 Warren, Plymouth

$949,000

2 Beds ⋅ 2 Baths ⋅ 73559145 MLS

Nestled along the tranquil Eel River in Plymouth’s highly sought-after Chiltonville neighborhood, this beautifully updated contemporary ranch embodies the best of sophisticated one-level living. Thoughtfully renovated with timeless style and quality craftsmanship, this exceptional residence offers two bedrooms and two full baths, blending comfort, functionality, and refined design in an idyllic waterfront setting. The heart of the home is a breathtaking cathedral-ceiling newly remolded (2026) kitchen where exposed beams and a dramatic floor-to-ceiling white brick wood-burning fireplace create a striking architectural centerpiece in the spacious living room with walls of windows to enjoy the natural light. The adjacent dining room with closet and French doors is perfect flex space. Beautifully refinished hardwood flooring flows throughout the light-filled living spaces, while the open-concept design captures peaceful views of the surrounding landscape. A beautifully crafted three-season room with custom molding and bead board ceiling provides a private retreat, while an expansive porch and oversized deck with a custom retractable awning invite effortless indoor-outdoor living. Outside, a sparkling in-ground pool with surrounding patios & storage shed overlooks a sweeping rolling lawn that gently extends to the Eel River, creating a private setting for entertaining or quiet relaxation.Additional highlights include a two-car garage under and a Title V-approved four-bedroom septic system, providing outstanding potential for a future addition or accessory dwelling unit (ADU), subject to local approvals. The lower level has a heated private office area or play room. Offering contemporary flair, exceptional outdoor amenities, waterfront beauty with the ever changing season and room to grow, this remarkable Chiltonville property is just minutes from Plymouth’s historic waterfront, beaches, shopping, restaurants, golf, and commuter routes.

61 Clifford Rd, Plymouth

$1,049,000

2 Beds ⋅ 3 Baths ⋅ 73557554 MLS ⋅ ['Saltash At Chiltonville'] BLDG.

Saltash at Chiltonville, situated on 25 wooded acres deed-restricted for no future development, is an exceptional 55 + neighborhood of only 48 duplex condos constructed reminiscent of the area’s quintessential historic homes. The architect reimagined four classic Chiltonville homes - the Greek Revival, Cottage, Half Cape & Half Colonial ranging from 2300 to 2700 sq ft (plus additional bonus rooms) with 2 car garages & full basements. First floor owner's suites, private yards & patios, clubhouse, pool, fitness center & pet friendly. Saltash was conceptualized, designed & constructed with a Net Zero goal in mind. All the amenities you expect along with the finest details & craftsmanship you deserve. Residents may enjoy reduced energy cost, natural wildlife, mature trees & surrounding native plantings. Near Downtown / waterfront, beaches, and area golf. Saltash & Plymouth have everything you need to live your life to the fullest. Lot 19 is a Half Colonial with a walk out lower level. Model homes ready to preview. 50% SOLD

46 Sandwich Road Unit 19, Plymouth

$1,950,000

3 Beds ⋅ 3 Baths ⋅ 73556046 MLS

Amazing 8 acre property in Chiltonville with views of the Gurnet lighthouse & the Atlantic Ocean from high atop Sandwhich Rd hill. This large contemporary boasts a spacious gourmet kitchen, high-end 6 burner stove, rotisserie, griddle, granite countertops, island seating, pantry, breakfast nook & stunning views out to the mahogany deck overlooking a private estate. Formal dining room, front to back living room & charming fireplace. Main bedroom suite, walk-in closet & private bath, 2 additional bedrooms & huge room over the garage. 1st floor laundry, freshly painted inside & out, irrigation, propane generator with auto back up, Seller owned solar panels, wood stove in basement, dog kennel, well water, new purifier, ductless mini splits AC & heat pump, security sys, vegetable garden, grapevine pergola, wooded trails, beautiful lawn & gardens, 2 car garage, overhead door for walkout basement. So much land to admire & wildlife for your family to enjoy. Don't miss this rare opportunity to own a piece of property this size in the heart of desirable Chiltonville. 2mi to Plymouth Beach, 4mi to downtown Plymouth, seconds to rte 3.

60R Sandwich Rd, Plymouth

$499,500

73552233 MLS

Oceanview buildable lot with existing 720 square foot recently renovated cottage in 2024 with modern interior that can remain for ADU or potential Inlaw situation perfect for multigenerational living. Engineering plans approved for a 5 bedroom septic system ( buyer responsibility ). Lot staked. Rare opportunity to build your dream home on this incredible .31 acre parcel of land with access from both Bay Shore and Tower roads offering views of Plymouth Bay, The property is perfectly located approximately 40 miles from Boston, minutes to Rte 3 and approximately 20 minutes to the Cape Cod Canal. Minutes from Public Beach / Area golf, Plymouth Waterfront / Downtown where you can enjoy arts, history, fine dining, entertainment and shopping. Perfect for a get away vacation home or year round.

41 Bay Shore Dr, Plymouth

$499,500

1 Beds ⋅ 1 Baths ⋅ 73513937 MLS

Oceanview recently renovated 720 sq ft cottage with modern light & bright interior that can remain or used for ADU / potential Inlaw situation perfect for multigenerational living. In 2024 the Cottage was completely gutted inside including ~ plumbing & electrical with 200 Amp service, all wall materials, floor covering & ceilings. Walls were removed to enlarge the ktichen & bedroom. Samsung appliances, Heating & cooling by Mitsubishi heat pump. Fiber optic internet, insulation, full basement w/ concrete floor. Engineering plans approved for a 5 bedroom septic system ( buyer responsibility ). Lot staked. Rare opportunity to build your dream home on this incredible .31 acre parcel of land with access from both Bay Shore & Tower roads offering views of Plymouth Bay, Perfectly located approx 40 miles from Boston, 20 minutes to the Cape Cod Canal. Short distance to Public Beaches / Area golf, Waterfront / Downtown where you can enjoy arts, history, fine dining & entertainment .

41 Bay Shore Dr, Plymouth

$1,015,000

2 Beds ⋅ 3 Baths ⋅ 73450890 MLS ⋅ ['Saltash At Chiltonville'] BLDG.

Saltash at Chiltonville, situated on 25 wooded acres deed-restricted for no future development, is an exceptional 55 + neighborhood of only 48 duplex condos constructed reminiscent of the area’s quintessential historic homes. The architect reimagined four classic Chiltonville homes - the Greek Revival, Cottage, Half Cape & Half Colonial ranging from 2300 to 2700 sq ft (plus additional bonus rooms) with 2 car garages & full basements. First floor owner's suites, private yards & patios, clubhouse, pool, fitness center & pet friendly. Saltash was conceptualized, designed & constructed with a Net Zero goal in mind. All the amenities you expect along with the finest details & craftsmanship you deserve. Residents may enjoy reduced energy cost, natural wildlife, mature trees & surrounding native plantings. Near Downtown / waterfront, beaches, and area golf. Saltash & Plymouth have everything you need to live your life to the fullest. Model homes ready to preview and purchase. 50% SOLD

46 Sandwich Road Unit 7, 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.