Plymouth Real Estate

Welcome to Plymouth, a charming town nestled in Litchfield County, Connecticut. Known for its picturesque landscapes and small-town charm, Plymouth offers residents a peaceful and close-knit community to call home.

With a rich history dating back to the 18th century, Plymouth boasts a blend of historic architecture and modern amenities. Residents can explore local landmarks such as the Lock Museum of America or enjoy outdoor activities at Lake Winfield and Hancock Brook.

The town's convenient location provides easy access to neighboring cities like Hartford and Waterbury, making it an ideal choice for those seeking a tranquil lifestyle with proximity to urban centers. Plymouth also offers a range of housing options, from historic colonial homes to contemporary properties, ensuring there is something for everyone.

In addition to its natural beauty and cultural attractions, Plymouth has a strong sense of community spirit. Residents can participate in local events, farmers' markets, and community gatherings, fostering connections and friendships that make living here truly special.

Whether you're looking to settle down in a peaceful setting or seeking a new adventure, Plymouth has something for everyone. Come and discover the beauty and warmth of this charming town in Litchfield County, Connecticut.

Newest Listings in Plymouth

$230,000

2 Baths ⋅ 24193031 MLS

Investors take notice! Two retail store fronts. Come with your own ideas and business! Being sold AS IS.

11 S Main St, Plymouth

$599,900

4 Beds ⋅ 2 Baths ⋅ 24192601 MLS

Welcome to the waterfront lifestyle at 160 Lake Plymouth Blvd! Set on one of the larger, beautifully landscaped lots in this sought after lake community, this fully updated 4 bedroom, 2 bath home offers direct lake access, a private dock and breathtaking panoramic views of Lake Plymouth. A beautiful stone patio creates a welcoming front entry. Inside, the bright open concept main level is designed for entertaining, with oversized windows filling the kitchen, dining and living areas with natural light and spectacular lake views. The fully remodeled kitchen features granite countertops, a center island and stainless steel smart appliances. Smart lighting, locks, switches and outlets connect to Wi-Fi for convenient home control. The fully remodeled main bathroom features a jetted tub, tiled shower and flooring. Main level laundry adds convenience, while 3 bedrooms are located upstairs. The finished walkout lower level offers a spacious family room, 4th bedroom and full bath, ideal for guests, extended family or private retreat. Step outside to the expansive covered deck to dine, relax and enjoy the views in any weather. The oversized backyard leads directly to the lake for swimming, kayaking, fishing and boating from your own dock. A 2 car attached garage and driveway parking for 6 additional vehicles provide plenty of space. Whether used as a year-round residence, weekend getaway or potential Airbnb investment, this rare waterfront property lets you vacation at home every day!

160 Lake Plymouth Blvd, Plymouth

$639,900

4 Beds ⋅ 4 Baths ⋅ 24190900 MLS

Magazine-ready and meticulously maintained, this exceptional home is privately nestled on 1.81 acres of serene, natural beauty. Filled with natural light from oversized windows and soaring ceilings, the thoughtfully designed interior showcases timeless finishes, rich hardwood floors, and inviting living spaces anchored by two fireplaces. Offering four bedroom and 3.5 baths, the home also features a private walk-out lower-level suite with its own entrance an outdoor living area - ideal for multigenerational living, guests, a teenager, or income-producing Airbnb potential. A rare combination of privacy, versatility and timeless appeal.

56 Meghan Blvd, Plymouth

$225,000

2 Beds ⋅ 2 Baths ⋅ 24189754 MLS ⋅ Winfield Lake Village BLDG.

This two-bedroom end unit at Winfield Lake Village offers plenty of natural light and a spacious layout. The kitchen features extra cabinets and counter space, plus a slider leading to the deck. There's a convenient half bath on the first floor. Upstairs, you'll find two generous sized bedrooms with ample closet space and a full bath showcasing a large walk-in shower and double vanity. The end unit allows for extra windows in all the rooms which is not found in the interior units. The full basement has a bulkhead for easy access getting things in and out from outside. Underground utilities. Easy access to Rte 8. Quick occupancy is available.

13 Holt St Unit 80, Plymouth

$375,000

4 Beds ⋅ 2 Baths ⋅ 24190579 MLS

Welcome to 16 Dewey Avenue in the Terryville section of Plymouth! This Renovated 4-bedroom, 2-bath Cape offers the perfect blend of comfort, convenience, and opportunity to make it your own. The updated kitchen features granite countertops, stainless steel appliances, and a cozy eat-in dining area. The main level also includes a formal dining room, spacious living room, a first-floor bedroom, a full bath, and an enclosed front porch with newer windows, creating a bright and inviting space to relax year-round. Upstairs, you'll find three additional bedrooms and a second full bathroom, providing plenty of room for family, guests, or a home office. Additional highlights include a generator hookup, central air conditioning, natural gas heating, public water and sewer, and major updates such as the roof and windows, both replaced in 2015. Unfinished basement is ideal for storage space. Outside, enjoy a detached one-car garage, an attached storage shed, beautiful paver patio area and a level backyard that's perfect for entertaining, gardening, or outdoor activities. Conveniently located near shopping, restaurants, schools, and everyday amenities, this home offers both comfort and accessibility. Don't miss your opportunity to make this wonderful home your own-schedule your private showing today!

16 Dewey Ave, Plymouth

$289,777

4 Beds ⋅ 2 Baths ⋅ 24187384 MLS

Discover a classic twofamily home set on a spacious, level 0.58acre lot at 26 Harwinton Avenue - a versatile property offering comfort, convenience, and income potential. This wellmaintained multifamily residence features two separate units, providing an excellent opportunity for rental income or an owneroccupied setup. The home includes 4 total bedrooms and 2 full baths, offering flexibility for a variety of living arrangements. The property sits on a level lot, ideal for outdoor enjoyment, gardening, or future enhancements. Public water and sewer connections add everyday convenience, and the home includes onsite laundry, making it even more attractive for tenants or owners. Built with classic New England charm, the home features vinyl siding, natural gas hotwater heating, and a partial basement for storage. Located in a quiet Plymouth neighborhood, it offers easy access to local amenities while maintaining a peaceful residential feel. Whether you're looking to invest or settle into a property with builtin income potential, 26 Harwinton Avenue is ready to make it your own.

26 Harwinton Ave, Plymouth

$595,500

4 Beds ⋅ 3 Baths ⋅ 24189369 MLS

Beautifully maintained 4-bedroom, 2.5-bath Colonial offering picturesque views of Lake Winfield from its desirable cul-de-sac location in one of Terryville's most sought-after neighborhoods. Complete with a 2-car garage, this move-in-ready home offers the perfect blend of comfort, space, and everyday convenience. The spacious floor plan features generous room sizes and a layout designed for both relaxed living and effortless entertaining. Pride of ownership shines throughout, with recent updates including a one-year-old water heater, whole-house humidifier, water booster pump for exceptional water pressure, and an underground irrigation system servicing the front yard. Imagine starting your day with peaceful lake views and ending it in the privacy of your own neighborhood retreat. Just moments away, Lake Winfield offers kayaking, fishing, scenic walking trails, pickleball and tennis courts, and a charming picnic gazebo, creating an active outdoor lifestyle right around the corner. Conveniently located just 5 minutes from Route 8, approximately 20 minutes from ESPN, and about 40 minutes from Hartford, this home provides easy access to shopping, dining, recreation, and everyday conveniences while maintaining the tranquility of a neighborhood setting. A rare opportunity to enjoy lake views, a sought-after location, and a home that has been lovingly cared for inside and out.

27 Maggie Ct, Plymouth

$415,000

3 Beds ⋅ 2 Baths ⋅ 24189035 MLS

This remodeled 3 bedroom Cape has a brand new kitchen with stainless steel appliances, 2 brand new bathrooms, new heating system, new electrical panel, new windows, freshly refinished hardwood floors, and fresh paint inside and out! You'll love the location with a large front yard and large back yard and the neighborhood has larger well kept homes. There is also a large enclosed patio so you can enjoy the nice weather without having to deal with the bugs. Don't wait, this one won't last!

63 Ridge Rd, Plymouth

$299,900

3 Beds ⋅ 1 Baths ⋅ 24189258 MLS

Welcome to the newly renovated 11 Chestnut! This home has everything you need from convenience to the flow of the home. The living room has a perfect picture window that lets in the perfect amount of natural lighting, giving a light and airy feel to the home. The kitchen has stainless steel appliances, a chic backsplash and a side door with convenient access to the driveway. Each bedroom is spacious with plenty of closet space; need a home office? No problem! Grab one of the bedrooms and make it your own working space! The finished basement is perfect for a second living area or a home gym! Located close to Route 8 and just minutes from shopping and dining, this home is a great spot to call yours!

11 Chestnut St, Plymouth

$349,900

3 Beds ⋅ 1 Baths ⋅ 24188063 MLS

Off the beaten path, yet close to everything, this raised ranch is ready for you to settle in and enjoy your summer. The beautiful yard is bordered by a private wooded area, providing a serene outdoor space. Inside, the expansive kitchen opens up to a dedicated dining room, with sliding doors leading to the deck. Sunlight through the picture window fills the living room, which flows seamlessly into the dining kitchen, making it a great space for entertaining while preparing dinner. The home features three bedrooms with new flooring and a large bathroom that opens from the hallway and the primary suite. Although the basement is not finished, there is a designated room for a bathroom, along with laundry hookups. Another room needs some drywall and flooring-bring your imagination! Additional highlights include a brand new Bosch oil tank and a roof that is only 8 years old. The homeowner currently uses the well for water, but the public water line is also present in the house and waiting to be connected.

40 Old Waterbury Rd, Plymouth

$350,000

3 Beds ⋅ 2 Baths ⋅ 24188728 MLS

This spacious and welcoming colonial home features 3 bedrooms, Dining room, Hard wood floors throughout first floor, 2 Full baths and a new Roof. The Professionally finished basement comes with a Transferable Warranty. Built in 1980 this well maintained home is perfect for comfortable and easy living. Sellers just had the entire home professional cleaned.

42 Makara St, Plymouth

$550,000

4 Beds ⋅ 3 Baths ⋅ 24187935 MLS

Welcome to this beautiful 4-bedroom Colonial nestled on a large, private lot in one of the area's most sought-after subdivisions. The inviting front porch is the perfect spot to enjoy your morning coffee while taking in the peaceful surroundings. Step inside to a welcoming foyer that leads to a thoughtfully designed main level featuring a formal living room or home office with hardwood flooring, a formal dining room, and a spacious family room with a cozy wood-burning stove that flows seamlessly into the eat-in kitchen. The kitchen offers tile flooring, attractive countertops and backsplash, a peninsula with additional seating, an abundance of cabinet space, and the perfect layout for entertaining family and friends. A full bath with a walk-in shower completes the main level. Upstairs, the primary suite features its own private bath, while three additional generously sized bedrooms and a second full bath provide plenty of space for family and guests. Step outside to the beautifully wooded backyard, offering exceptional privacy and an oversized Trex-style deck that's perfect for entertaining, outdoor dining, or simply relaxing. Additional highlights include Andersen windows throughout the first floor, a spacious storage shed, city sewer, private well, and a new architectural roof installed in 2025. This well-maintained home combines comfort, space, and privacy in a highly desirable neighborhood. Don't miss your opportunity to make it yours! MOVE QUICK!

39 Old Farm Rd, Plymouth

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