Chiltonville Homes for Sale

Welcome to Chiltonville, a hidden gem nestled in the heart of Plymouth, Massachusetts. This charming neighborhood is known for its picturesque landscapes and tight-knit community, making it an ideal place to call home. With its rich history and stunning natural beauty, Chiltonville offers a unique blend of suburban tranquility and easy access to urban amenities.

Surrounded by lush greenery and serene waterways, residents can enjoy the scenic views and recreational opportunities that abound in this area. From hiking trails that wind through the nearby Myles Standish State Forest to the beautiful beaches along Cape Cod Bay, outdoor enthusiasts will find plenty to explore. The local parks and playgrounds also provide family-friendly spaces for children to play and grow.

Chiltonville is conveniently located just a short drive from downtown Plymouth, where you can indulge in a variety of dining, shopping, and entertainment options. The rich historical significance of the area, including landmarks like Plymouth Rock and the Mayflower II, adds to the charm and allure of this community.

For those considering a move to this enchanting neighborhood, there are a variety of homes for sale in Chiltonville that cater to diverse tastes and budgets. Whether you’re looking for a cozy single-family home, a spacious colonial, or a modern new build, you’ll find inviting options that make it easy to settle into this delightful community.

Come and discover the warmth and charm of Chiltonville—where your dream home awaits!

Newest Chiltonville Homes for Sale

$1,180,000

5 Beds ⋅ 4 Baths ⋅ 73585350 MLS

Steeped in Plymouth history, 8 Winter Street is a remarkable historic residence offering a rare opportunity to own a treasured piece of New England's architectural heritage. Known as the Sgt. William Harlow Family Homestead, this distinctive gambrel-roofed Cape reflects generations of history, craftsmanship, and timeless character. Thoughtfully preserved and expanded over the centuries, including a substantial 19th-century addition, the home showcases exquisite period details throughout, including exposed wood beams, wide-plank wood flooring, and five fireplaces. Offering five bedrooms and 3.5 baths, including a first-floor primary suite, the home blends historic charm with modern conveniences, including an automatic gas generator. Listed on the National Register of Historic Places, this extraordinary property is situated on a .48-acre level lot in a desirable in-town location with ocean views, just a short stroll to Stevens Field Beach and Park, and minutes from Plymouth's historic waterfront, shops, and restaurants. A detached two-car carriage-style garage offers possible ADU potential, subject to approvals, while a separate outbuilding offers an inspiring setting for an art studio. A potting shed and gorgeous perennial gardens throughout the grounds create a gardener's dream. Town water , sewer and natural gas. A rare opportunity to embrace historic coastal New England living in the heart of Plymouth.

8 Winter St, Plymouth

$1,699,000

5 Beds ⋅ 5 Baths ⋅ 73582835 MLS

Set in one of Chiltonville’s most sought-after enclaves, this stately brick-front colonial offers a rare blend of elegance, privacy, and golf-course living. Nestled on a serene, tree-lined lot directly abutting the 13th green of Plymouth Country Club, the property delivers both prestige and peaceful natural surroundings. Adding to its charm and versatility, the property was formerly operated as a bed-and-breakfast, showcasing its welcoming layout and potential for future use. The home’s classic brick façade is enhanced by beautiful arched windows that bring character and abundant natural light throughout. The Great Room serves as the heart of the home, featuring a grand wood-burning fireplace and seamless flow into the spacious Kitchen, an ideal layout for entertaining and everyday living. A first-floor primary retreat adds convenience and flexibility, while rich African mahogany hardwood floors bring warmth, character, and craftsmanship across the main level. Upstairs, the home offers three well-proportioned bedrooms, including a Jack-and-Jill bathroom connecting two of the rooms. A loft area provides additional flexible living space, perfect for a reading nook, play area, or home office. Throughout the home, there is generous closets and storage space, adding practicality to its elegant design. The bright and spacious lower level offers a versatile living area with a well-appointed kitchen featuring granite countertops, custom cabinetry, and abundant storage. Currently occupied by an excellent tenant, the space provides an attractive opportunity for rental income while also offering flexibility for extended living arrangements, a private guest area, home office, or additional recreational space.. Recent significant update includes newer wood shingled roof consistent with its elegant design. Private road, not a drive by!

7 Hibiscus Ln, Plymouth

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 73582352 MLS

Welcome to modern luxury in Chiltonville’s coveted Beech Tree Estates. Tucked away on a quiet cul-de-sac, this stunning 5 year young 3-bed, 2.5-bath home perfectly balances a fresh modern farmhouse aesthetic with timeless classic design. Meticulously crafted with high-end custom upgrades, this turn-key property offers a low-maintenance sanctuary tailored for effortless daily living and grand-scale entertaining. Guests are welcomed through one of the home's two front doors—the side entrance serves as the primary point of entry, featuring a striking entryway accent wall, convenient coat hooks, and a dedicated coat closet. This functional foyer leads seamlessly into an expansive, sun-drenched open living pavilion. Aspiring chefs will love the spectacular custom kitchen, featuring premium appliances, sleek subway tile accents, a dedicated pot-filler, a massive center island, and a walk-in pantry. This magnificent culinary space flows into the dining area and a vaulted living room centered around a cozy gas fireplace with custom built-ins and oversized windows. Tucked away on the main level, the private first-floor primary suite serves as a peaceful sanctuary, complete with two walk-in closets and a beautifully appointed en-suite bathroom showcasing dual vanities, modern granite finishes, and premium hardware. Finishing the main level is a dedicated home office behind classic French doors, offering a quiet workspace, a bright half bath, and a laundry room with its own storage. Upstairs, the second floor provides an ideal layout for family or guests, featuring two additional spacious bedrooms—including one with its own large walk-in closet—and a second full bathroom. Outside, relax on the welcoming covered front porch or the back deck nestled among pristine landscaping and perfect for outdoor dining. Practical details abound, including an attached garage and a whole-house generator for absolute peace of mind. Beyond your property lines lies an unmatched lifestyle. Stroll down the street to the historic Bramhall's Country Store for fresh local produce and seasonal treats. Enjoy a movie night out at nearby Plimoth Pawtuxet or take advantage of being just less than 2 miles from Plymouth Beach. With downtown Plymouth’s historic dining and waterfront just three miles away, golf courses and nature trails around the corner, and effortless proximity to highway commuter routes, this location truly offers the very best of New England living.

41 Bramhall Lane, Plymouth

$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

$1,250,000

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

$929,000

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

$1,950,000

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

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