Plymouth Homes for Sale

Welcome to Plymouth, Connecticut—a charming town nestled in Litchfield County that beautifully blends small-town warmth with stunning natural landscapes. Known for its rich history and vibrant community spirit, Plymouth offers a unique lifestyle that appeals to families, retirees, and everyone in between. With picturesque views of rolling hills and serene lakes, it's no wonder that residents here cherish their surroundings.

Plymouth is steeped in tradition, with historical landmarks like the Plymouth Historical Society and the iconic Terryville Congregational Church. Outdoor enthusiasts will revel in the town's abundant recreational opportunities, including hiking trails, parks, and the beautiful Lake Winfield. The community is also home to various local shops, restaurants, and seasonal events that foster a strong sense of camaraderie among residents.

When it comes to real estate, Plymouth has a diverse selection of homes for sale that cater to various lifestyles and budgets. Whether you're seeking a cozy single-family home, a charming colonial, or a spacious modern property, you'll find an array of options that suit your needs. Many of these homes feature beautiful yards, contemporary amenities, and easy access to the town's vibrant amenities.

With its friendly community, rich history, and stunning scenery, Plymouth is not just a place to live—it's a place to thrive. Explore the homes for sale in this delightful town and discover the perfect setting for your next chapter. Your dream home awaits in Plymouth, where comfort and community come together seamlessly!

Newest Plymouth Homes for Sale

$649,900

1 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24194576 MLS

Nature Lovers, Outdoor Enthusiasts & Investors-A Rare 9.839 Acre Opportunity!Discover a truly one-of-a-kind property offering nearly 9.8 acres of privacy, natural beauty, and exceptional future potential along the Plymouth/Terryville-Wolcott town line. Whether you're seeking a peaceful country estate, horse property, hobby farm, recreational retreat, or investment opportunity, this remarkable offering delivers a lifestyle that is increasingly difficult to find.The beautifully updated home is warm, inviting, and move-in ready, featuring gleaming hardwood floors, a renovated kitchen with abundant cabinetry, a beautifully remodeled bathroom, fresh interior updates, a new furnace, newer roof, and new wall-to-wall carpeting upstairs. The versatile floor plan includes a convenient first-floor bedroom, while the upper level offers exciting possibilities for an expansive primary suite, guest quarters, home office, or recreation space. The true value of this exceptional property extends well beyond the home. The 9.839-acre offering consists of four parcels that were previously divided and later combined, including approximately 1.169 acres in Plymouth/Terryville (Parcel A), 1.587 acres in Wolcott (Parcel A), 1.700 acres in Plymouth/Terryville (Parcel B), and a 5.383-acre Parcel B in Wolcott that has historically been taxed as a buildable lot, creating exciting future possibilities. Buyers are encouraged to conduct their own independent diligence regarding land use, subdivision pot

251 Wolcott Rd, Plymouth

$339,990

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24194955 MLS

If you are looking for the perfect home in the Plymouth/Terryville community, search no more! This charming, very spacious sprawling colonial is absolutely beautiful, with well-preserved original hardwood flooring and finishing throughout. You'll be taken in by an absolutely remarkable and unforgettable front entrance and foyer; this home boasts original craftsmanship, making it a classic beauty! The property also includes many updates to accommodate modern living! Larger rooms are perfect for hosting and dining, and set apart bedroom quarters for more privacy and quiet living. A fully finished basement is ready to accommodate your favorite hobbies, entertaining, or home activities; a new roof, new driveway, and recent vinyl siding. New pavers have also been added leading to an open sunny porch. What more is there to say? Only one thing left for you to do -- schedule your personal showing today!

9 Pearl St, Plymouth

$599,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$375,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$595,500

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$349,900

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$305,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24185524 MLS

Opportunity awaits with this classic Cape-style home set on a 1+ acre lot in Plymouth. Offering 2 bedrooms with an expandable second floor, this home provides the perfect chance to add living space and build equity while making it your own. Inside, you'll find oak hardwood flooring, living area, and a walk-in shower for added convenience. The home is equipped with warm-air, oil heat, city sewer, and a full, usable basement that offers excellent storage, workshop space, or future possibilities. Outside, the two-car garage and generous yard provide plenty of room for vehicles, hobbies, gardening, or outdoor entertaining. With solid bones, desirable features, and a peaceful setting, this home is ready for your personal updates and vision. If you are someone looking for a property with potential, this is a wonderful opportunity to create the home you've been dreaming of.

230 South St, Plymouth

$515,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24186542 MLS

Spacious, inviting, and well maintained, this home offers nearly 3,000 square feet of well-designed living space, blending comfort, style, and functionality. The heart of the home is the kitchen featuring granite countertops, a classic subway tile backsplash, an oversized island with seating for four, and multiple pantry closets-perfect for both everyday living and entertaining. The kitchen opens seamlessly to a dramatic great room with cathedral ceilings, gleaming hardwood floors, and a cozy pellet stove. With 4-5 generously sized bedrooms and 2.5 baths, this home provides flexibility for a variety of living needs. The desirable main-level primary suite is highlighted by a charming bow window, walk-in closet, and a full bath with a tiled shower. Additional conveniences include a main-level laundry room for easy, single-level living. Set on 1.68 acres, the outdoor space is ideal for relaxation and recreation, featuring an above-ground pool with deck, a two-car detached garage, and a storage shed. Added peace of mind comes from roof heat coils to help during winter months. Ideally located near Peterson Park, you'll enjoy easy access to trails, playgrounds, skating, and more. This lovely home is ready for new owners to move in and enjoy!

316 Allentown Rd, Plymouth

$599,999

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24178339 MLS

Better than new, this stunning split level home has been completely reimagined with exceptional attention to detail, high end finishes, and energy efficient upgrades throughout. Offering 3 bedrooms & 2 full baths, this turn key property is the perfect blend of modern style and everyday functionality. Step inside to discover beautifully, refinished dark, walnut hardwood floors, crown molding, updated lighting, new interior doors, trim, and custom finishes throughout. The show-stopping kitchens feature quartz countertops, elegant marble and mother of pearl mosaic backsplashes, and newer appliances. Recent improvements include a new Owens Corning roof with transferable warranty, new windows, doors, black seamless gutters, front walkway, oversized asphalt driveway, updated well water tanks and lines, &a new high efficiency HVAC system. Spray foam insulation in both the basement and attic provides year round comfort and impressive energy savings. The finished lower level with separate entrance provides additional living space to suit a variety of your needs, along with the addition of the converted garage to office space which allows for even more versatility. Outside, enjoy the newly installed patio, and private backyard perfect for entertaining. Every inch of this home has been thoughtfully updated, creating a truly move in ready property. Simply unpack and enjoy.

3 Burger Rd, Plymouth

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.