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$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

Listing courtesy of Listing Agent: Kelly Roche from Listing Office: Atlantic Homes.
$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

Listing courtesy of Listing Agent: Sheri Sibley from Listing Office: Engel & Volkers, South Shore.
$869,000
5 Beds ⋅ 3 Baths ⋅ 73559897 MLS
This is a single family home. HOWEVER, it is laid out perfectly for multigenerational living or side-by-side living. See floor plan in photos. Single family listing is MLS# 73556214 for additional info. No HOA fee, beach access, addition with home upgrades completed in 2008. Appraisal completed 7/6/26. Value was ABOVE current asking price. New septic at closing. Reach out with any questions.

24 Mayflower Drive, Plymouth

Listing courtesy of Listing Agent: Ricardo Real Estate Group from Listing Office: Keller Williams South Watuppa.
$3,290,000
5 Beds ⋅ 4 Baths ⋅ 73559499 MLS
Waterfront Estate — 3 Acres, one mile from downtown Plymouth. This rare waterfront estate offers scale, privacy, and sweeping harbor views. The property features a 5,800 sq ft main home with a four-car garage, a 1,100 sq ft guest/pool house, a tennis court, and a swimming pool.The main residence has been stripped to the studs and reconfigured to maximize water views — offering a strong foundation for renovation or new construction. Recent lot line adjustments provide approximately 2 buildable acres. Additional features include gas heat, town water/sewer, and a fully permitted dock. With over 400 feet of waterfront between Boston and Cape Cod, this is a rare opportunity to create a premier South Shore estate.

214 Sandwich St, Plymouth

Listing courtesy of Listing Agent: Nick Rivers from Listing Office: Compass.
$849,000
5 Beds ⋅ 4 Baths ⋅ 73549622 MLS
Set back from the road on a private, wooded one-acre lot, this lovingly maintained Colonial is tucked within the sought-after Harrison Woods neighborhood, where approximately 72 acres of surrounding conservation land create a uniquely peaceful setting. Located on a quiet loop road with a strong sense of neighborhood connection, this home offers a rare combination of privacy and community. Enjoy morning coffee while watching deer pass through the winter landscape and hummingbirds visit the gardens each summer. Inside, the flexible five-bedroom, 3.5-bath floor plan provides generous space for work, guests, hobbies, and everyday living, while the updated composite deck and tranquil koi pond create a private backyard retreat. Ideally situated near walking trails, Morey's Pond for fishing and kayaking, Indian Brook Elementary School, and Route 3A, this special Harrison Woods property offers the perfect blend of nature, convenience, and neighborhood appeal.

88 Early Red Circle, Plymouth

Listing courtesy of Listing Agent: Shana Lundell from Listing Office: Coldwell Banker Realty - Plymouth.
$850,000
5 Beds ⋅ 3 Baths ⋅ 73548983 MLS
Located in Plymouth's thriving downtown district this property presents an excellent investment opportunity or owner-occupied option. Ideally situated just minutes from Route 3, downtown Plymouth's restaurants and shops, Nelson Memorial Park, the waterfront, and numerous local attractions, the location offers strong tenant appeal. The units have been thoughtfully updated in recent years and feature modern kitchens and bathrooms, recessed lighting, spacious bedrooms, tiled showers, and refinished wide pine hardwood floors. A full basement provides on-site laundry and additional storage, while the private driveway offers ample off-street parking. The spacious yard and storage shed add valuable outdoor amenities, making this a highly desirable property for both tenants and owners alike.

211 Court St, Plymouth

Listing courtesy of Listing Agent: Patrick Ryan from Listing Office: Ryan Realty Group LLC.
$3,895,000
5 Beds ⋅ 5 Baths ⋅ 73532558 MLS
Experience unparalleled privacy in this gated, fully fenced 10-acre estate built in 2023, boasting over 600 feet of pristine water frontage on Great South Pond and abutting 40+ acres of protected conservation land with walking trails. Crafted with quality 2x6 framing, the main home features oak hardwood floors, quartz countertops, an open floor plan with a gas fireplace, a game room, and breathtaking views from every room. Enjoy a private sandy beach on crystal-clear, peaceful waters where gas-powered boats are restricted. A separate apartment above the three-car garage includes a full kitchen, bath, and laundry. Modern essentials include a generator, a Trex deck, and robust keypad security and video monitoring. An older waterfront guest cottage offers incredible potential. Located minutes from Pinehills Golf Club and under four miles from historic downtown Plymouth, this sanctuary perfectly blends secluded natural luxury with everyday convenience.

140 Drew Rd, Plymouth

Listing courtesy of Listing Agent: Mark Anderson from Listing Office: Redfin Corp..
$810,000
5 Beds ⋅ 4 Baths ⋅ 73515895 MLS
Exceptional 5-bedroom, 3.5-bath Colonial nestled on a private 0.86-acre lot, offering the perfect blend of space, comfort, and style. A 2-car attached garage, oversized driveway, and abundant parking provide everyday convenience. Inside, you'll find an inviting open layout with hardwood floors, a beautifully appointed kitchen featuring granite countertops, island, and stainless steel appliances, a formal living room with fireplace, a tucked-away family room with wet bar, home office, and first-floor half bath. The second level offers four spacious bedrooms, including a serene primary suite with a custom tile shower and private bath. The expansive entire third-floor bedroom suite with its own full bath is ideal for guests, multigenerational living, or a private getaway. Relax in the fenced backyard with an oversized composite deck, all just minutes from beaches, Ellisville Harbor State Park, shopping, dining, and major highways. Welcome Home!

16 Ellisville Rd, Plymouth

Listing courtesy of Listing Agent: Jeffrey Monast from Listing Office: Conway - Wareham.
$5,500
5 Beds ⋅ 4 Baths ⋅ 73491128 MLS
OFF SEASON RENTAL-AVAIL Oct 2026..Stunning oceanfront nestled on 1.5 acres of panoramic ocean views in Ellisville Harbor. Chef's kitchen, breakfast nook, dining room w/ gorgeous views of Cape Cod bay from every window! 4 beds, 3 baths, over 3,500 sf of versatile living space. A beautiful great room featuring beamed cathedral ceilings, double-sided gas fireplace, & sliders to the deck. The 2nd level boasts the primary suite & 2 additional bedrooms. Contemporary & sun-filled with a heated oceanside saltwater pool, hot tub & 2 decks perfect for entertaining. A walkout lower level office, family room & bedroom. Separate guest quarters over the 2 car garage available at an additional fee would total 5 bedrooms, 4 baths. Short stroll to Landing Way beach, minutes to Cape Cod Canal & area golfing. Tenant is responsible for all utilities, landscaping, pool maintenance, trash & snow removal. Owner pays water and taxes. Liability/content insurance policy required. First, last & security is due upon signing lease. Full app. package required. Pets negotiable. Guest quarters above garage is negotiable. $5500 per mo through March or April of 2027.

31 Ellisville Rd, Plymouth

Listing courtesy of Listing Agent: Margo Pisacano from Listing Office: Margo & Company.

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