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790 Chapman Rd, Plymouth
$950,000
4 Beds ⋅ 4 Baths ⋅ 5103924 MLS
Set high in Vermont’s green hills, this contemporary estate blends architectural sophistication with complete privacy on 20 pristine acres. Southern-facing glass, 18-foot timber-beamed ceilings, and frame-worthy views fill the home with natural light year-round. The sun-drenched great room features cathedral ceilings, rich wood accents, and a sleek Rais wood stove set on slate floors that store passive solar warmth. The open living and dining areas flow to a fully appointed kitchen with down-draft cooktop and direct deck access for effortless indoor-outdoor entertaining. The main-level primary suite offers vaulted ceilings, a dedicated wood stove, and a spa-like bath with whirlpool tub. Above, a dramatic loft walkway under skylights and a 32-foot illuminated cupola connects two serene bedrooms and a full bath. The finished lower level adds a flexible media lounge, office or 5th bedroom, half bath, laundry, and mudroom. Outdoor living shines with a 40-foot screened porch and sundeck overlooking wildflower fields, mature trees, walking trails, and natural streams. The property includes a separate 10-acre section previously perked for a 3-bedroom home - ideal for a guest house or future development. An oversized heated garage accommodates vehicles plus all your mountain gear. Located minutes from Okemo, Killington’s Skyeship Gondola, VAST trails, lakes, golf, and the amenities of Ludlow and Woodstock.

790 Chapman Rd, Plymouth

Listing courtesy of Jason Saphire from www.HomeZu.com. ()
no property photo
$549,900
3 Beds ⋅ 2 Baths ⋅ 22603808 MLS
A Direct Waterfront botanical garden retreat. Come experience the true peace of nature all around you in this very private lakefront home. Four total lots being sold together make for a very private space. Imagine the possibilities within this delightful property. Wonderful open floor plan welcomes you with its first-floor kitchen/dining and living room as well as two bedrooms and a bath. Enjoy the wood burning fireplace as you marvel at the amazing sunsets with your ample water views. Large deck for summer dining. Good size sleeping loft with sitting room for the overflow of guests. Walkout Basement is finished with an additional bedroom, half bath and family room with fireplace. 10-year-old roof. Great walkout patio that leads right down to the pond and dock. Enjoy the amazing flowering trees and perennial. Pick your own blueberries from the garden. Watch the wildlife as you relax or take a kayak over to the sandy beach. Property is close to all major highways for easy commute. Just a short ride to the Cape Cod Canal, Onset, and Scusset beaches! Easy access to the Cape Cod Bridges or downtown Plymouth. Truly the perfect location! Motivated sellers! Bring offers! Motivated sellers! Bring offers! Town has this as a 2 bedroom, but upstairs is a loft bedroom. 10-year-old roof.

7 Cranberry Road, Plymouth

Listing courtesy of Listing Agent: Judy M Chauvin (jchauvin@comcast.net) from Listing Office: Cape Landing Real Estate.
6 Headlands Dr, Plymouth
$279,900
3 Beds ⋅ 2 Baths ⋅ 73560120 MLS
Space, sunlight, and an easy-flowing layout make living here easy-peasy! This bright and inviting 3-bedroom, 2-bath modular home welcomes you through a cheerful three-season room. The spacious living room flows seamlessly into the dining area and newly updated kitchen. The main bedroom is privately situated at one end of the home, with two additional bedrooms and a full bath at the other. A convenient laundry/utility room with its own exterior entrance is an added bonus. Enjoy three separate entrances, mature plantings, and a shed for your gardening tools. The monthly fee includes trash removal, snow plowing, taxes, shared well, septic, clubhouse access, and maintenance of common areas. Located in a desirable 55+ community and ready for a quick sale—come take a look!

6 Headlands Dr, Plymouth

Listing courtesy of Listing Agent: Sandra Smith from Listing Office: Gibson Sotheby's International Realty.
14 Snapdragon, Plymouth
$761,900
2 Beds ⋅ 3 Baths ⋅ 73560086 MLS
NEW CONSTRUCTION – Ready for NOVEMBER/DECEMBER delivery! Brand New Floor Plans at Symington Woods. The beautifully designed "Tidewater" floor plan features an open-concept 1st floor layout perfect for modern living. The spacious kitchen offers a large pantry and a seamless flow into the dining and living areas, ideal for entertaining. Step out from the living room onto a private deck with peaceful treetop views. With 3 spacious bedrooms and 2.5 baths, this home combines style, comfort, and functionality. Tons of storage in the unfinished walk-out basement or huge potential for more living space! Don’t miss the opportunity to own this exceptional new construction home with a one year builder warranty. Proudly built by Whitman Homes.

14 Snapdragon, Plymouth

Listing courtesy of Listing Agent: Timothy Porter from Listing Office: East Bay View Realty LLC.
7 Cranberry Road, Plymouth
$549,900
3 Beds ⋅ 2 Baths ⋅ 73560076 MLS
DIRECT WATERFRONT! botanical garden retreat. Come experience the true peace of nature all around you in this very private lakefront home. Four total lots being sold together make for a very private space. Imagine the possibilities within this delightful property. Wonderful open floor plan welcomes you with its first-floor kitchen/dining and living room as well as two bedrooms and a bath. Enjoy the wood burning fireplace as you marvel at the amazing sunsets with your ample water views. Large deck for summer dining. Good size sleeping loft for the overflow of guests with sitting area Walkout Basement is finished with an additional bedroom, half bath and family room. Great walkout patio that leads right down to the pond and dock. 10-year-old roof. Enjoy the amazing flowering trees and perennial. Pick your own blueberries from the garden. Watch the wildlife as you relax or take a kayak over to the sandy beach. Property is close to all major highways for easy commute. Close to the elementary school. Just a short ride to the Cape Cod Canal, Onset, and Scusset beaches! Easy access to the Cape Cod Bridges or downtown Plymouth. Truly the perfect location! Motivated sellers! Bring offers! Title 5 in hand!

7 Cranberry Road, Plymouth

Listing courtesy of Listing Agent: Judith Chauvin from Listing Office: Cape Landing Real Estate.
8 Tideview Path Unit 7, Plymouth
$188,000
2 Beds ⋅ 1 Baths ⋅ 73559898 MLS ⋅ ['Pine Hills Village'] BLDG.
***NEW lower price! PLUS-Seller to pay HOA Fees through June 2027*** Looking to live in Plymouth? This garden style condo has 2 spacious bedrooms and a full bath and is an affordable entry in to the Plymouth market. A big plus is that the heat and hot water are included in the monthly HOA fee; a great feature for the owner occupying this unit or for potential renters if you choose to make this an investment property. The deeded parking spot is just outside your front door. Bathroom updates done in 2017 and the kitchen in 2023. The complex is set back from the main road and is conveniently located to so much of what Plymouth offers. Shopping, Route 3, and beautiful White Horse Beach are only minutes away. Plymouth Beach, the Waterfront, and Downtown are an easy ride up Route 3A. The unit is priced to provide the new owner the flexibility to make finishes, touch-ups, and cosmetic enhancements as they see fit.

8 Tideview Path Unit 7, Plymouth

Listing courtesy of Listing Agent: Charles Goonan from Listing Office: Jane Coit Real Estate, Inc..
24 Mayflower Drive, Plymouth
$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.
50 Union Street Unit 50, Plymouth
$949,000
2 Beds ⋅ 3 Baths ⋅ 73559147 MLS
Experience luxury coastal living in this exceptional turnkey, end-unit, townhome overlooking picturesque Plymouth Harbor. Thoughtfully updated, this residence offers timeless elegance, modern upgrades, and breathtaking ocean views from every level. Recent improvements include new flooring, electrical and plumbing updates, a redesigned stairwell, updated fixtures, new water heater, and a new garage door. The entry level features a spacious guest bedroom, full bath, laundry room, one-car garage, and a cozy gas fireplace with access to a private outdoor deck. Upstairs, the open-concept main level is designed for effortless entertaining. The chef's kitchen offers abundant cabinetry, expansive counter space, double ovens, and an oversized breakfast bar. The adjoining dining area flows into the impressive living room featuring a gas fireplace, wet bar, and sliders leading to a spectacular harbor-facing deck complete with an electric fireplace and TV mount.The private primary suite occupies the upper level and offers a spacious bedroom, double closets, walk-in dressing room, and spa-inspired bath with double vanity, soaking tub, spacious walk-in shower, and mini refrigerator. Enjoy your private balcony while taking in panoramic harbor views and unforgettable sunsets. Just steps from downtown Plymouth's waterfront, restaurants, shops, marina, parks, beaches, and historic attractions. This move-in ready home offers an unparalleled lifestyle in one of the area's most desirable locations.

50 Union Street Unit 50, Plymouth

Listing courtesy of Listing Agent: Lynne Morey from Listing Office: Coldwell Banker Realty - Plymouth.
61 Clifford Rd, 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

Listing courtesy of Listing Agent: Lynne Morey from Listing Office: Coldwell Banker Realty - Plymouth.
14 Milford St, Plymouth
$550,000
3 Beds ⋅ 2 Baths ⋅ 73559091 MLS
Back on market, buyer’s financing fell through! This turn-key, updated 1,768-square-foot split-level home in Plymouth features a brand new 3 bedroom septic, a level fully fenced-in level backyard (great for dog lovers!!!) , brand-new flooring and fresh paint throughout. The layout begins on the first level, which features a spacious, standalone family room anchored by a brick accent wall and a cozy gas stove fireplace insert. Just a few steps up, the second level boasts an eat-in kitchen complete with wood cabinetry, granite countertops, and stainless steel appliances. From the kitchen, step out onto a massive rear deck with built-in bench seating that overlooks the private, fenced yard. This second floor also includes a comfortable bedroom and a full bathroom. Just four steps above that, the private primary bedroom suite sits over the garage, highlighting soaring vaulted ceilings, a ceiling fan, and French doors that open to a charming Juliet balcony.The finished basement tier below provides excellent privacy, offering a third bedroom with a double closet and its own private en-suite bathroom. Just outside this bedroom, a nicely finished foyer houses the laundry room and a walkout door to the backyard. Additional property highlights include a tankless natural gas hot water heater, town water, and an attached two-car garage. This move-in-ready property perfectly combines privacy, modern upgrades, and local convenience.

14 Milford St, Plymouth

Listing courtesy of Listing Agent: Christopher Sheridan from Listing Office: Symmetry Realty.
39 Snowy Owl Ln, Plymouth
$1,290,000
5 Beds ⋅ 3 Baths ⋅ 5103229 MLS
Experience the best of mountain living at this exceptional custom residence in Hawk Resort, offered fully furnished for a turnkey opportunity. Set on 1.33 private acres with seasonal views of Lake Amherst and Okemo Mountain, this impeccably maintained home offers over 3,500 square feet of thoughtfully designed living space between Okemo's Jackson Gore Base and Killington's Skyship Gondola. Built with an uncompromising commitment to quality, craftsmanship, and energy efficiency, where exceptional construction extends beyond what meets the eye. Carefully engineered for Vermont's climate, every detail was carefully considered, from its superior mechanical systems and premium materials to the care and improvements that have kept the property in exceptional condition. The kitchen, dining area, and great room flow effortlessly together, making it the heart of the home and creating an inviting space where family and friends gather together. The home features soaring cathedral ceilings, expansive windows, and a dramatic floor-to-ceiling stone fireplace. The great room and primary bedroom provide access to the three-season porch and expansive composite deck, creating effortless indoor-outdoor living. The lower level is complete and features a walkout to a beautifully crafted paver patio, where you can enjoy the property's serene natural setting year-round. Offering five bedrooms, two full and one three quarter baths, a flexible floor plan includes a finished walkout lower level with a spacious family room, a recreation area, a dedicated office, and ample space for family and guests, and 5 zone heating and cooling on the main level . Meticulously landscaped grounds, a paved driveway, and an exceptional 34'x28' garage with extra-deep bays allowing room for vehicles, recreational equipment, a workshop, and extensive storage above. A rare offering where timeless craftsmanship, exceptional quality, and an unmatched mountain lifestyle come together in one remarkable property.

39 Snowy Owl Ln, Plymouth

Listing courtesy of Heidi Matusik from Ski Country Real Estate. ()
6 Westcliff Dr. Unit Golfview, Plymouth
$410,000
2 Beds ⋅ 2 Baths ⋅ 73558735 MLS ⋅ ['White Cliffs Country Club'] BLDG.
Wow, what a value, you'll love this 2bdrm - 1.5-bath condo nestled beautifully within the SPECTACULAR, OCEANFRONT White Cliffs Country Club! Enjoy peace of mind with a newer kitchen with gorgeous white quartz countertops, stainless steel appliances, updated baths and newer HVAC! You'll love this location with a private setting offering a serene back patio and golf course views, perfect for relaxing or entertaining. Indulge in top-notch amenities: unlimited golf on a meticulously maintained course, Har-Tru tennis courts, a newly updated exercise facility, and a four-season mineral water swimming pool (under construction). Direct access to a spectacular beach lets you soak in the beauty of Cape Cod Bay—where you can order umbrella drinks and lunch and have them delivered to you on the beach! White Cliffs is a vibrant, active community hosting social events from golf and tennis tournaments to dances and wine pairing dinners. Savor dining alfresco as you overlook the breathtaking bay. Experience the best of coastal living and resort-style luxury at White Cliff's! One of the BEST KEPT SECRETS on the SOUTH SHORE! Live the Good LIFE!

6 Westcliff Dr. Unit Golfview, Plymouth

Listing courtesy of Listing Agent: Mary Gugenheim from Listing Office: Coldwell Banker Realty - Plymouth.
84 Westcliff Unit 84, Plymouth
$419,900
2 Beds ⋅ 2 Baths ⋅ 73555991 MLS ⋅ ['White Cliffs'] BLDG.
New Price--- still high end features! The one you are waiting for! New Lennox (26k) HVAC system, new leaf guard gutters, custom built ins surrounding fireplace, custom ceiling fans, updated kitchen and baths... no detail overlooked! White Cliffs gated community offers ocean side clubhouse, elevator to beach, golf, tennis, swimming pool (currently being renovated), and MORE! Bright flowers surrounding entry porch. Step out rear door to private paved patio. Two generous sized bedrooms, full bath with extra large, deep soaking tub connecting directly to main bedroom, Main bedroom has roomy double closets. All closets feature closet storage systems. This unit has it all...just unpack and enjoy all this seaside gated community offers. Live the Seaside Life! Appointments being scheduled, CALL NOW to book a time to view your next home!

84 Westcliff Unit 84, Plymouth

Listing courtesy of Listing Agent: Wendy Pomeroy from Listing Office: Plymouth Sails Realty, LLC.
18 Preservation Way, Plymouth
$889,900
4 Beds ⋅ 3 Baths ⋅ 73557805 MLS
New construction- MOVE IN DECEMBER 2026 - Perfect family home with spacious open design 1st floor and 4 bedrooms 2nd floor. Relax in the private wooded setting of your newly built home by Premier South Shore Builder Eric Pontiff at Redbrook's newest neighborhood The Preserve on the Agawam. Our homes combine traditional New England style with contemporary living offering classic lines, open floor plans & superior quality for easy living. Enjoy all the amenities of new construction with kitchen/dining area open to living room w/gas fireplace, large mudroom w/separate entry. Step outside to the pet friendly walking trails along scenic cranberry bogs or walk to the Village Green to the YMCA . Nearby schools, beaches, ponds, golf. Easy access to Rte 3 & the Cape. Choose upgrades to receive $10,000 Options Credit when you sign P&S by Oct 31.

18 Preservation Way, Plymouth

Listing courtesy of Listing Agent: Sue Meharg from Listing Office: E.J. Pontiff Properties.
73 Raymond Rd, Plymouth
$559,000
3 Beds ⋅ 2 Baths ⋅ 73557748 MLS
Come discover the allure of 73 Raymond Rd, a 1987 Colonial-style single-family residence in the sought after neighborhood of THE PONDS OF PLYMOUTH. With 1789 square feet of inviting, open living space, this property is just waiting for your personal touches. The kitchen is equipped with newer stainless steel appliances, providing a functional and contemporary space for your culinary pursuits. Just off the kitchen is a lovely dining room and a front to back Living room that is spacious and inviting.The 2nd level features a large, bright primary bedroom with walk-in closet and dressing area. The other two bedrooms have double closets and plenty of windows to let in the beautiful, natural light. Outside, a large deck extends the living space, perfect for outdoor gatherings, complemented by a fire pit that invites evenings under the stars. This property offers a thoughtful layout- with a little TLC you can create an ideal setting for your next chapter.

73 Raymond Rd, Plymouth

Listing courtesy of Listing Agent: Susan Kiefer from Listing Office: RE/MAX Real Estate Center.
95 Little Herring Pond Rd, Plymouth
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 73557389 MLS
A distinguished custom-built New England-style home by Karbott Construction. Designed for those who appreciate a harmonious blend of privacy and accessibility. Featuring 4 well-appointed bedrooms, 2.5 baths, a grand owner's suite with a cathedral ceiling, 2nd-floor flex space, and hardwood floors. The first floor offers an abundance of natural light and an open yet defined layout, with a bright, spacious home office, family room, and formal dining room used as a den. All of this is situated on a double lot of 2.2 acres that adjoins David E. Alper Preserve with walking trails. Plenty of room for an ADU or a potential house lot (buyer to do due diligence). The back of the lot extends to Carter’s River, with access to 90-acre Little Herring Pond, or a stroll to Triangle Pond, both perfect for kayaking, skating & swimming. Fully recreational 376-acre Great Herring Pond is just down the street. Nature lovers' paradise. Fully landscaped front & back with rock walls & mature plantings, two connected deck areas, and a large, level, private backyard ideal for entertaining. Walk-out basement with private entrance; future expansion possibility. Two-car garage with EV charging station. Whole-house generator! Minutes to Cape Cod Canal, beaches, and area golf. We invite you to schedule your private viewing to fully appreciate the distinctive qualities of this remarkable property.

95 Little Herring Pond Rd, Plymouth

Listing courtesy of Listing Agent: Michele Monteiro from Listing Office: Keller Williams Elite.
30 Bissell Rd, Plymouth
$499,900
3 Beds ⋅ 3 Baths ⋅ 24194875 MLS
Escape the hustle and bustle take a look at this charming country contemporary in a beautiful private setting. The road dead ends into the forest with walking paths. The Livingroom is the focal point with high ceilings and a master crafted stone fireplace. Walk out the sliders to an expansive deck where you can sit on a lounge chair and enjoy the impressive country views. Kitchen with huge center bar opens into the living room. Plus you still can enjoy the formal dining room which has doors leading out to a comfy screened summer porch and open patio. Perfect house for entertaining! Primary bedroom has a full bath with walk in shower, his and her closets plus convenient laundry area. Second bedroom has the main bath close by. The huge Family room offers the perfect area for fun gatherings and entertaining. Off this room is the 3rd bedroom or private office plus 1/2 bath. There are 2 spacious garages, one has heat for working on your car. Natural stone walls adorn the front of this home which sets on a beautiful scenic 2.2 acre lot. There is a 640 sq ft barn on the property with 2 stalls for animals (town and neighbor approval needed) but can be used for storage etc. 2 year old roof on house and barn. 3 zone heat. 1485 Sq ft on first fl. 600 sq ft finished lower level. Total 2085 sq ft. The peacefulness is so relaxing. Come take a look.

30 Bissell Rd, Plymouth

Listing courtesy of Paula Kendall from Country Manor Realty. (860) 559-9349 (860) 589-2100
232 Soaring Hawk Rd, Plymouth
$450,000
3 Beds ⋅ 2 Baths ⋅ 5102572 MLS
Tucked away on a quiet road in Hawk Resort, this charming 3-bedroom, 2-bath mountain retreat offers privacy, warmth, and easy access to Vermont's best four-season recreation. Just under 1,300 square feet, the home is thoughtfully designed to make the most of its inviting spaces, with random-width pine floors, a classic fieldstone fireplace, and abundant windows that bring in natural light and views of the surrounding woods. The open living area flows to a spacious deck, creating the perfect setting for morning coffee, evening gatherings, or simply enjoying the peaceful natural surroundings. Ideally located halfway between Killington Resort and Okemo Mountain Resort, you'll enjoy convenient access to skiing, golf, hiking, mountain biking, and endless outdoor adventure. Nearby lakes offer swimming, kayaking, and fishing, while the charming village of Woodstock is just 30 minutes away for shopping, dining, and exploring. Showings start 8/4.

232 Soaring Hawk Rd, Plymouth

Listing courtesy of Debra Staniscia from Four Seasons Sotheby's Int'l Realty. (debra.staniscia@fourseasonssir.com)
no property photo
$989,000
8 Beds ⋅ 5 Baths ⋅ 22603671 MLS
Premier Plymouth equestrian facility with exceptional opportunity to own a turnkey 5.5+-acre equestrian estate designed for the serious horse enthusiast, trainer, or boarding operation. This impressive property features an 18-stall horse barn complete with automatic waterers in every stall, individual turnouts, a heated tack room, wash area, huge loft and 1-bedroom, 1-bath apartment--ideal for an on-site manager, trainer, or guest accommodations. Ride year-round in the expansive 160' x 70' indoor riding arena, offering ample space for training, lessons, and conditioning regardless of the season. The thoughtfully designed facility provides everything needed for a professional or private equestrian operation. In addition there is an option to buy the 4 car garage with a charming 2-bedroom apartment above for an additional $689k. A truly one of a kind equestrian offering combining exceptional flexibility, and direct access to miles of riding trails in Myles Standish state forest! The income potential and possibilities are endless with this little slice of heaven yet close to everything that Plymouth has to offer!

9 Riesling Road, Plymouth

Listing courtesy of Listing Agent: Amanda L DeFazio (amanda.defazio@raveis.com) from Listing Office: William Raveis Real Estate & Home Services.
11 Page St, Plymouth
$280,000
3 Beds ⋅ 2 Baths ⋅ 5102351 MLS
Welcome to 11 Page Street in Plymouth, New Hampshire! Nestled on a quiet dead-end road, this well-maintained double-wide manufactured home offers the perfect blend of peaceful country living and convenient access to downtown Plymouth, shopping, dining, and local amenities. Designed for comfortable one-level living, the home features updated insulation for improved energy efficiency and year-round comfort, insulated exterior doors, central air conditioning, a new roof, a new water heater with an expansion tank installed to current New Hampshire code requirements, and new smoke and carbon monoxide detectors for added peace of mind. Step outside to enjoy the spacious back deck—perfect for relaxing with your morning coffee or entertaining friends and family. The property also offers plenty of space for gardening, a one-car garage with an attached shed, plus an additional outbuilding, providing abundant storage for tools, hobbies, and outdoor equipment. Whether you're searching for a primary residence or a low-maintenance home in a quiet setting, this property combines comfort, functionality, and thoughtful updates in a desirable location. Sale is contingent upon the seller securing suitable housing. Please, no drive-bys.

11 Page St, Plymouth

Listing courtesy of Samantha Catterall from KW Coastal and Lakes & Mountains Realty/Hanover. ()
251 Wolcott Rd, Plymouth
$599,900
3 Beds ⋅ 1 Baths ⋅ 24194576 MLS
WHAT IF HOME FELT LIKE YOUR OWN PRIVATE GETAWAY? Hidden among nearly 9.8 acres of beautiful CT countryside is a warm, updated three-bedroom home offering something increasingly difficult to find-privacy, nature, versatility and space to make your own. Inside, hardwood floors and fresh updates create an inviting atmosphere. The kitchen offers abundant cabinetry and stainless-steel appliances, while the remodeled bathroom, new furnace, newer roof and new upstairs carpeting make this home ready to enjoy. The floor plan includes one first-floor bedroom and two additional bedrooms upstairs, providing flexibility for today's changing lifestyles. Step outside and the possibilities expand dramatically. Explore your own wooded trails. Create beautiful gardens. Enjoy wildlife outside your window. Bring your outdoor hobbies. Dream about horses, a hobby farm or simply having almost ten acres where weekends can feel like a vacation. Need space for cars, tools, toys or projects? The oversized detached two-car garage with loft provides exceptional additional storage and workspace.

251 Wolcott Rd, Plymouth

Listing courtesy of Barbara Podlisny from William Raveis Real Estate. (203) 641-8649 (203) 272-0001
24 Mayflower Drive, Plymouth
$869,000
4 Beds ⋅ 3 Baths ⋅ 73556214 MLS
Welcome to 24 Mayflower Drive, where coastal charm meets flexible living in one of Plymouth's most desirable seaside neighborhoods. Offering over 3,400 square feet of living space, this beautifully maintained 4 bedroom, 3 full bathroom home features a versatile layout with two updated kitchens, making it ideal for extended households, guests, or a variety of living arrangements. The spacious primary suite offers water views, while the rooftop deck provides the perfect place to relax and enjoy scenic views of the bay. Just a short stroll to Surfside Beach, this property is located in the sought-after Surfside Estates neighborhood with no homeowners association. Outside, you'll find a fenced backyard, an oversized shed (yes, that has water views too!), a one-car garage, and a generous lot with ample off-street parking. Combining exceptional space, flexibility, and a premier location, this is a rare opportunity to enjoy all that Plymouth's lifestyle has to offer.

24 Mayflower Drive, Plymouth

Listing courtesy of Listing Agent: Ricardo Real Estate Group from Listing Office: Keller Williams South Watuppa.
22 Southcliff Dr., Plymouth
$600,000
2 Beds ⋅ 3 Baths ⋅ 73555639 MLS ⋅ ['White Cliffs Country Club'] BLDG.
**BEST KEPT SECRET ON CAPE COD!**. **LIGHT, BRIGHT & BEAUTIFUL!** Welcome to this inviting 2-bedroom, 2.5-bath Patio-style home at **White Cliffs Country Club**, where soaring architectural ceilings, an open floor plan and abundant natural light create a wonderful sense of space. Beautiful hardwood floors flow throughout the first floor, while the crisp white kitchen features quartz countertops, stainless steel appliances and an open design perfect for everyday living and entertaining. The spacious living room with gas fireplace and dramatic vaulted ceiling opens to a private patio—an ideal spot for morning coffee, summer dinners or simply relaxing outdoors. A separate dining area, first-floor laundry and half bath add convenience. Upstairs, a versatile open loft offers the perfect space for a home office, den or reading retreat, along with a generous primary suite, guest bedroom and two full baths. With approximately 1,560 sq. ft. of living space, an attached garage and a private setting, this home offers easy, comfortable living. But the real magic is **WHITE CLIFFS!** One of Plymouth’s best-kept secrets, this gated oceanfront community offers a lifestyle that feels like being on vacation every day. Enjoy **unlimited golf, Har-Tru tennis, private beach access, oceanfront dining overlooking Cape Cod Bay, fitness facilities, putting green, clubhouse and a spectacular new four-season aquatic center scheduled for completion in December 2026.** The community also features beach rights and an indoor heated pool among its extensive amenities. Golf in the morning, head to the beach in the afternoon and finish the day with dinner overlooking Cape Cod Bay. This isn't simply a place to live—it's a lifestyle. LOVE WHERE YOU LIVE...LIVE THE GOOD LIFE AT WHITE CLIFFS!**

22 Southcliff Dr., Plymouth

Listing courtesy of Listing Agent: Mary Gugenheim from Listing Office: Coldwell Banker Realty - Plymouth.
34 Nautical Way, Plymouth
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 73555510 MLS
FIRST OPEN HOUSE 8/16 11-1:30 34 Nautical Way in Plymouth’s highly sought-after Ship Pond Estates is ready for you to call home! This exceptional property delivers the perfect blend of comfortable indoor living and a thoughtfully designed outdoor living area. On the first floor, a huge eat-in kitchen opens seamlessly to the living room, creating an inviting space for everyday living and entertaining. The first floor also features a primary suite and a huge walk-in closet, complete with an attached bathroom. There is also an additional bathroom and dedicated laundry room! Upstairs, you’ll find three more large bedrooms and two full bathrooms, one of which is en-suite. Expansive additional living space above the garage offers an open area ideal for gathering with family and friends. Downstairs, the finished basement provides flexible living space perfect for a rec room, home gym, media space, or guest quarters—and it already features a built-in bar!Step outside to the property’s standout feature: a massive addition that includes a beautiful pool and dedicated pool house, creating your own private backyard oasis. Enjoy complete privacy and security with the fully fenced-in yard, supported by a professional retaining wall. A dedicated irrigation system keeps the landscaping lush and low-maintenance, while outdoor audio sets the perfect soundtrack for poolside entertaining. A whole-home generator provides reliable backup power and peace of mind year-round. Located just minutes from the ocean, this home offers coastal living at its finest with upgrades that truly set it apart. Don’t miss this rare opportunity!

34 Nautical Way, Plymouth

Listing courtesy of Listing Agent: Kyle Walker from Listing Office: RE/MAX Vantage.
no property photo
$915,000
2 Beds ⋅ 1 Baths ⋅ 22601733 MLS
These waterfront cottages are passed down through generations and rarely offered--here is your opportunity! A private, off-grid enclave accessible by 4WD or boat, Saquish offers unmatched seclusion. The open floor plan is ready for summer enjoyment, currently configured to sleep a large group. Updated roof, windows, and siding. Tucked in the dunes, enjoy sweeping views, bay breezes, an oversized deck, and a second-floor balcony. This is a location defined by its rarity--where land narrows and the Atlantic surrounds you in a dynamic coastal landscape shaped by tides, light, and season. This location is where Plymouth, Cape Cod and Duxbury Bays all intersect!!! Wake to sunrise over the bay, spend your days with direct beach access, and end with unobstructed sunset skies. Whether a seasonal escape or legacy holding, this is a singular opportunity in one of the South Shore's most tightly held coastal settings. Short term rental potential. Ready to enjoy as is, but the possibilities are endless!

Saquish Beach Boulevard, Plymouth

Listing courtesy of Listing Agent: Mary Wall (gildedgirlsgroup@gmail.com) from Listing Office: Beach Homes Realty, LLC.
70 Bentgrass Mist Unit 70, Plymouth
$1,247,739
3 Beds ⋅ 3 Baths ⋅ 73555070 MLS ⋅ ['Bentgrass Mist'] BLDG.
PINEHILLS -- THE LAST AVAILABLE HOME AT BENTGRASS MIST! NEW FRESCO 3 PLUS DESIGNER HOME READY FOR MOVE IN FALL OF 2026 . Located in the heart of the village green, where the shopping, restaurants, golf and spa are just a short stroll away. The award-winning Fresco 3 Plus home will not disappoint. This 3-bedroom, 3 full bath condominium boasts a spacious floor plan, screened in porch and private courtyard. The primary bedroom is located on the first floor along with a guest bedroom that can also be used for an office space. The second floor allows guests to have their privacy hosting a loft and full bathroom. A walkout lower level lends for great storage or additional living space. Enjoy the luxury of new construction and condominium living including all the Pinehills amenities. With interior selections made by our exclusive design team this home is a true show piece! Nothing to do but move right in!

70 Bentgrass Mist Unit 70, Plymouth

Listing courtesy of Listing Agent: Caryn Wennerberg from Listing Office: The Green Company.
16 Firefly Point Unit 16, Plymouth
$963,205
2 Beds ⋅ 2 Baths ⋅ 73555071 MLS
PINEHILLS --- NEW very popular FRESCO 2 currently being built, ANTICIPATED FALL 2026 MOVE IN. $65,000 of selected options applied at no cost to buyer. Located high on the Ridge with a vista view of the Atlantic and tall pines, this designer home will not disappoint. This 2-bedroom, 2 full bath, condominium boasts a spacious floor plan, a private courtyard, farmers porch and screened in porch. Enjoy one floor living with primary bedroom, guest room, 2 full baths and den/office all conveniently located on the first floor. A walkout lower level with windows lends for great storage or option to finish later for additional living space. Enjoy the luxury of new construction and condominium living including all of the Pinehills amenities, as well as the Ridge amenities with Meeting House, bocce courts and heated pool. Selections have been made by our award winning design team! Call to schedule an appointment. After all, nothing to do but happily move in!

16 Firefly Point Unit 16, Plymouth

Listing courtesy of Listing Agent: Caryn Wennerberg from Listing Office: The Green Company.
9144 Rte 100, Plymouth
$550,000
5101569 MLS
Skiers, Riders, and Investors: Your Ultimate Vermont Chalet Awaits! Nestled just north of the desirable Lakes Region, this charming duplex chalet offers the perfect blend of alpine recreation and investment potential. Location is everything here. You are just a few minutes from the world-class slopes of Killington Resort and a short 15-to-20-minute drive to Okemo Mountain Resort. Whether you are looking for a full-time residence, a vacation getaway, or an income property, this versatile duplex allows you to live or play on one level while generating rental revenue from the other. Lower-Level Unit (2 Bedrooms, 1 Bathroom) Step inside through a dedicated air-lock entry designed to keep the winter chill at bay. This cozy, efficient space features a fully equipped kitchen, a dedicated dining area, and a warm living space anchored by a gas fireplace. Practical amenities include a convenient mudroom with an attached storage room for all your gear, plus in-unit laundry. Upper-Level Unit (3 Bedrooms, 2 Bathrooms + Bonus Room) The upper configuration welcomes you with its own draft-stopping air-lock entry. It opens into a bright, airy open-concept kitchen, dining, and living area where another glowing gas fireplace serves as the centerpiece. Upstairs are 2 more bedrooms and a top-level bonus room offers the flexible space you need for a home office, a media room, or an overflow bunk space. Outdoor Living & Highlights The property sits on a pretty, open parcel of land that provides plenty of sunshine, balanced with flat, easy access to the main road for stress-free winter travel. Step out onto the expansive second-level deck to breathe in the mountain air, or head down to the private hot tub to soak your muscles after a long day on the ski trails. Don't miss this incredible opportunity to own a piece of Vermont paradise where you can sit back, relax, and let your property earn income for you!

9144 Rte 100, Plymouth

Listing courtesy of Elissa Scully from Mary W. Davis Realtor & Assoc., Inc.. (Off: 802-228-8811)
76 Ellisville Green, Plymouth
$819,000
4 Beds ⋅ 4 Baths ⋅ 73554514 MLS
Welcome to 76 Ellisville Green, a beautifully maintained contemporary colonial set on a private 1.38-acre lot in one of Plymouth’s most desirable Cul d Sacs. With 4,254 sq ft, 4-bedroom septic, 3 bedrooms + multiple flex spaces, and 4 bathrooms, this home offers exceptional versatility for multi-generational living, work-from-home needs, or future bedroom expansion.The main level features a dramatic two-story family room with oversized windows, a spacious kitchen in excellent condition, formal dining room, and a large living room perfect for entertaining. A first-floor bath and multiple bonus rooms create ideal options for a guest suite or office.

76 Ellisville Green, Plymouth

Listing courtesy of Listing Agent: Tara Iula D'Angelo from Listing Office: Coldwell Banker Realty - Duxbury.
1029 Old Sandwich Rd, 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

Listing courtesy of Listing Agent: Lynne Morey from Listing Office: Coldwell Banker Realty - Plymouth.

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