Plymouth Real Estate

Welcome to Plymouth, Connecticut—a hidden gem nestled in the heart of Litchfield County. This charming town beautifully combines small-town charm with modern convenience, making it an ideal place to call home. With a rich history dating back to the 18th century, Plymouth offers a unique blend of historical architecture and picturesque landscapes, perfect for those who appreciate both heritage and nature.

Plymouth is renowned for its scenic parks and outdoor recreational opportunities. The stunning Lake Winfield offers residents a tranquil spot for fishing, kayaking, and picnicking, while the surrounding hiking trails invite exploration of the lush woodlands. Families will love the community spirit here, with local events and festivals bringing neighbors together throughout the year.

The town's location provides easy access to major highways, making commuting to nearby cities like Hartford and Waterbury a breeze. This accessibility, paired with its peaceful atmosphere, makes Plymouth an attractive option for both young professionals and retirees alike.

Plymouth is also home to a variety of local businesses, from quaint shops to delightful eateries, ensuring that residents have everything they need right at their doorstep. The educational system here is highly regarded, with dedicated schools that focus on fostering a nurturing learning environment for children.

Whether you’re looking to settle down or invest in a vacation home, Plymouth offers an inviting community with a wealth of opportunities. Discover the charm of Plymouth, CT—where history meets harmony, and every day feels like a breath of fresh air.

Newest Listings in Plymouth

$289,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24217649 MLS

Welcome to 5 Lakeview Road, a three-bedroom, 1.5-bath home set on 1.38 acres in Terryville with beach rights to beautiful Fall Mountain Lake. Offering over 1,600 square feet of living space, the home features hardwood floors, central air, and a spacious mudroom .Eat in Kitchen, a freshly painted deck provides a pleasant place to enjoy the property and its natural surroundings. The detached, oversized two-car garage offers abundant room for parking, storage, and hobbies, with an unfinished area above ready for your plans. A new roof adds further value to this property, which combines generous outdoor space, versatile potential, and access to lake recreation.

5 Lakeview Rd, Plymouth

$287,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24217415 MLS

Set off the beaten path yet conveniently close to everything, this classic Cape Cod home sits on a scenic 1.4-acre lot framed by breathtaking fall foliage. Family-owned since 1946, this property offers a rare opportunity to bring your vision and build sweat equity in a peaceful setting. Inside, you'll find a large living room and hardwood floors throughout. The kitchen overlooks a beautiful backyard, offering lovely views while cooking or dining. The layout includes 3 bedrooms plus a versatile main-floor room that can easily serve as a laundry room or family room. Upstairs, the spacious half bathroom is large enough to add a walk-in shower. Enjoy excellent storage and parking with two garages: one attached via a large breeze-way, and a second drive-under garage with direct basement access. Key updates include a newer roof, a well-maintained 2007 boiler (serviced yearly), and an indirect water heater. Roll up your sleeves and make this cherished home your own!

238 Allen St, Plymouth

$420,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24217114 MLS

Meticulously maintained and thoughtfully upgraded, this 3-bedroom, 2.5-bath Colonial offers classic charm. Recent improvements include new central air, a new roof and a new shed, while a stand-alone generator adds peace of mind. A welcoming covered front porch provides the perfect spot for morning coffee. Inside, the sunlit living room features hardwood floors, a large picture window and a brick fireplace with a wood mantel. The kitchen offers abundant wood cabinetry, dark countertops, a mosaic tile backsplash, under-cabinet lighting and breakfast bar seating for casual meals. Storage is a standout, with two walk-in closets in the primary bedroom providing generous space for clothing and organization. The attached two-car garage and backyard shed offer additional room for tools, equipment and seasonal essentials. A lower-level recreation area provides flexible space for games, exercise or hobbies. Outside, a generous yard framed by mature trees creates an inviting setting for gardening, outdoor gatherings or relaxing. Pride of ownership shines throughout this welcoming Terryville home, blending comfortable living spaces, abundant storage and valuable upgrades inside and out.

20 Hickory St, Plymouth

$309,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24199534 MLS

Opportunity awaits in the Terryville section of Plymouth! This versatile 2-family offers two bedrooms on each floor, a detached 2-car garage, and a .26-acre lot. Both units feature their own front porches and vinyl-clad thermopane windows. Both units have been freshly painted! The first-floor and has oil heat, a brand-new 40-gallon electric hot water tank, and convenient washer/dryer hookups in the basement. Upstairs, the second-floor unit features an updated kitchen and bath, a fully applianced kitchen, in-unit washer/dryer hookups, electric heat, and a 6-year-old 40-gallon gas hot water tank. A walk-up, floored attic provides additional storage. With both units ready for new tenants or owner occupancy, this property offers flexibility whether you're looking to invest, owner-occupy, or expand your rental portfolio. The detached 2-car garage provides valuable parking and storage, adding even more versatility to this well-located property. Come see the possibilities!

7 Schultz St, Plymouth

$129,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24215589 MLS

Welcome to this inviting 2-bedroom mobile home located in the desirable Lakeside Sun Communities. This 55+ Community home offers comfortable living with several updates, including an updated full bath, new flooring & carpets and the entire home has been freshly painted. Additional features include, A Large Sunroom, newer windows and appliances including a washer & dryer and a large storage shed outside. Enjoy year-round comfort with central air. Whether you're looking to downsize or enjoy a more manageable lifestyle, this home offers a wonderful opportunity to make it your own. Don't miss your chance to enjoy comfortable living in a 55+ Community! Lakeside Community Monthly HOA/Land Lease of $640 covers water, sewer, trash pickup and property management as well as offsite amenities. Buyer must be approved by Sun Communities.

17 Lovely St, Plymouth

$310,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24215527 MLS

Peace of mind awaits with a fully updated, energy efficient HVAC, heating system, and central air components with humidity control, all under 5 years old! Full of charm and character, this early 1900s Colonial offers a welcoming blend of classic style and everyday comfort. Featuring 3 bedrooms and 2 full bathrooms, this inviting home offers a warm and comfortable atmosphere throughout. The kitchen features beautiful wood cabinetry and stainless steel appliances, creating a timeless look with modern appeal. Outside, enjoy a cute yard with space to relax, garden, or entertain. With its charming character and appealing features, this delightful Colonial is ready to welcome its next owner and offers a wonderful opportunity to make it your own.

28 Eagle St, Plymouth

$575,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24209734 MLS

Welcome to 94 North Street, where Cape Cod charm meets the peaceful beauty of Plymouth. Freshly painted inside and out in 2026, this four bedroom home pairs character with thoughtful updates. Refinished main level hardwood floors lead to an inviting living room with a cozy fireplace, while the dining room opens to an eat in kitchen with self closing cabinetry, granite counters, and backsplash. A bright breezeway with high ceilings provides more room to gather, featuring new doors including a new sliding glass door and refreshed carpeting, connects to the attached two car garage. Two main level bedrooms and a full bath offer flexibility for guests or a home office. Upstairs, the primary bedroom and another bedroom feature hardwood floors, joined by an office and second full bath. A new roof and Harvey tilt in windows were installed in 2014, followed by a new well pump, well system and water softener in 2020. The unfinished basement offers storage, with new Bilco entrance stairs and Drylok painted walls in 2026. Outside, new 2026 lighting welcomes you to a 3.85 acre lot with expansive lawn, mature trees and exciting potential for gardens, recreation and outdoor living. Enjoy added privacy from land behind the property where no additional homes can be built, along with a direct pathway to the lake. Across from a school and near Plymouth Reservoir, this special setting blends tranquility with everyday convenience.

94 North St, Plymouth

$420,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24214606 MLS

Space, character, and room to grow await at 31 Chestnut Street! This three-bedroom, two-and-a-half-bath home offers a generously sized kitchen, an oversized family room, and two wood-burning fireplaces that bring warmth and charm to the living spaces. Upstairs, a spacious primary bedroom and convenient second-floor laundry make everyday living easier. The recently updated, partially finished walkout basement offers flexible space for a lounge, home theater, recreation room, or office. An additional section is approximately 75% complete, with flooring remaining-an opportunity to expand the usable space and make it your own. A recently updated breezeway adds to the home's appeal. Enjoy outdoor gatherings or quiet mornings on the two-tier deck. Storage is plentiful, with space above the two-car garage and a separate basement storage area equipped with a sump pump. Solar panels are another notable feature. The neighborhood has a special history: the family who built the home still lives nearby, and neighborhood streets were named after the family's daughters. With a welcoming neighborhood atmosphere and convenient access to Terryville's local restaurants, this home offers a blend of comfort, space, and community.

31 Chestnut St, Plymouth

$300,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214292 MLS

Welcome to 16 Oak Street in Terryville! This inviting 4 bedroom, 2 bathroom home offers 1,473 square feet of living space with the added versatility of attached in-law accommodations featuring a full kitchen and separate private entrance! Perfect for extended family, multigenerational living, or guests, this flexible layout offers additional privacy and convenience. Inside, you'll find comfortable living spaces filled with natural light, attractive flooring, and plenty of opportunity to make the home your own. The main kitchen offers ample cabinetry and counter space, while the home's versatile layout provides options to accommodate a variety of needs. Additional highlights include solar panels, a newer roof, a welcoming covered front porch, and a detached garage offering convenient parking and storage. Outside, enjoy a spacious, level backyard with plenty of room for entertaining, gardening, or outdoor activities. Conveniently located in Terryville with public water and sewer, this property offers a wonderful combination of functionality, flexibility, and potential. Bring your ideas and discover all that 16 Oak Street has to offer!

16 Oak St, Plymouth

$359,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24212332 MLS

Welcome to 259 Main Street in Plymouth! Newly remodeled throughout, this 3 bedroom, 2 full bathroom home offers fresh finishes and beautiful updates. The kitchen features quartz countertops, vaulted ceilings, and skylights that fill the space with natural light, creating an inviting setting for cooking and entertaining. A new roof, new siding, and new windows enhance the home's curb appeal and complement the interior renovations. Schedule your private showing today!

259 Main St, Plymouth

$629,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24212712 MLS

Welcome to 21 Laurel Drive, a new construction colonial offering approximately 2,200 square feet of thoughtfully designed living space with 4 bedrooms and 2.5 bathrooms, set on a .54-acre lot. Designed for today's lifestyle, this new construction home combines a classic exterior with a spacious and functional interior layout. The main level will feature hardwood flooring throughout creating a warm and cohesive feel. The kitchen will be finished with granite countertops, stainless steel appliances and quality cabinetry. Upstairs, you'll find four bedrooms, including the primary suite, along with beautifully finished bathrooms. Additional highlights include central air conditioning, two-zone propane forced hot air heating, a 200-amp electrical service, low-E thermal pane windows and an attached garage with automatic openers. Exterior features will include low-maintenance vinyl siding, a Craftsman-style front entry, paved driveway and walkway, gutters, and a starter lawn. Connected to city water and city sewer, this home offers the opportunity to enjoy the comfort, efficiency and peace of mind that comes with brand new construction. A wonderful opportunity to make a beautiful new colonial your own!

21 Laurel Ave, Plymouth

$500,000

1 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24211965 MLS

Lakefront living awaits! Privately nestled among mature trees, this distinctive remodeled Contemporary offers a rare opportunity to enjoy waterfront living in the highly sought after Lake Plymouth community, complete with your own private dock. Enjoy the peaceful lifestyle of this non-motorized lake, ideal for swimming, fishing, kayaking and relaxing by the water. The beautifully reimagined main level features an open floor plan with hardwood flooring, stylish kitchen with quartz countertops and a center island with pendant lighting. The kitchen flows seamlessly into the living and dining areas, where a dramatic wall of windows showcases picturesque lake views and fills the home with natural light. Whether entertaining, enjoying your morning coffee or relaxing, this is a setting designed to be enjoyed year round. Upstairs, the spacious primary suite features French doors to your private balcony, a walk-in closet and an unfinished en-suite bath ready for completion, with space prepared for a tub and separate shower. A dedicated laundry room adds convenience. The finished lower level expands your living and entertaining options with a summer kitchen, full bath and living area with luxury vinyl plank flooring and a walkout leading directly to your private dock. Enjoy beach access and spectacular fall days on the lake. This unique waterfront retreat is truly a must see. All furnishings may remain with the property and included at no additional cost. Schedule your showing today!

196 Lake Plymouth Blvd, Plymouth

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Plymouth Real Estate

Newest Listings in Plymouth

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