Plymouth Homes under $250,000

Welcome to Plymouth, Connecticut – a charming town nestled in the heart of Litchfield County, where small-town charm meets serene natural beauty. Known for its rich history and vibrant community spirit, Plymouth is an ideal destination for those seeking a peaceful lifestyle without sacrificing convenience. With a population that values community and connection, Plymouth offers a welcoming atmosphere for families, young professionals, and retirees alike.

One of the standout features of Plymouth is its stunning landscapes, with picturesque parks, scenic trails, and the serene waters of Lake Winfield. Residents can enjoy a plethora of outdoor activities, from hiking and fishing to picnicking in the lush green spaces. The town also boasts a variety of local shops, eateries, and cultural attractions, making it easy to immerse yourself in the local culture.

For homebuyers on a budget, Plymouth presents an incredible opportunity with homes available for under $250,000. This affordability does not come at the expense of quality; many of these homes feature charming architectural details and modern amenities, perfect for first-time buyers or those looking to downsize. With a range of options, from quaint single-family homes to cozy condos, you can find the perfect place to call home in this inviting community.

Whether you’re drawn to Plymouth for its natural beauty, community vibe, or affordable housing options, you’ll discover that this hidden gem in Litchfield County offers a wonderful quality of life. Explore the possibilities and make Plymouth your new home today!

Newest Plymouth Homes under $250,000

$239,900

2 Beds ⋅ 1 Baths ⋅ 24211393 MLS

Welcome to 446 S. Main Street, a charming 2-bedroom ranch offering an easy one-level layout with valuable updates and plenty of potential. The main level features hardwood flooring, an updated kitchen with granite countertops, a refreshed full bath, and a comfortable, open flow between the living and dining areas. Major improvements include a newer roof and boiler, providing added peace of mind for the next owner. Set on approximately 0.56 acres, the property also offers a walkout lower level with additional usable space and great potential for a recreation room, home office, workshop, gym, or storage. Conveniently located in the Terryville section of Plymouth with easy access to local amenities and major routes. Whether you're a first-time buyer, downsizing, or looking for a home you can continue to make your own, 446 S. Main Street offers an affordable opportunity to build equity and settle into a home with many of the larger updates already completed.

446 S Main St, Plymouth

$179,900

3 Beds ⋅ 1 Baths ⋅ 24210091 MLS

Unlock the hidden equity in this diamond in the rough. Attention investors and Handy homeowners! Bring your tools and vision to 66 Lakeview rd. Plymouth Ct. a 3- bedroom, 1-bath single -family home brimming with potential. Tucked into a peaceful neighborhood, the property features a tiny lake view from the backyard, offering a serene glimpse of water to enjoy while planning your custom renovations. The front to back living room features a fireplace with wood insert. The roof was replaced 2 years ago, some newer window and newer siding and garage door. Please note this home will not pass government financing. living room floor dips and will need to be lifted and new column installed. ***THIS HOME IS 66 LAKEVIEW RD AT FALL MT LAKE IN THE TERRYVILLE SECTION OF PLYMOUTH. GPS MAY TAKE YOU TO WEST LAKEVIEW RD IN PLYMOUTH AT LAKE PLYMOUTH WHICH IS THE WRONG LOCATION

66 Lakeview Rd, Plymouth

$180,000

4 Beds ⋅ 3 Baths ⋅ 24192809 MLS

Great opportunity for investors, contractors, or renovators looking for a property with a flexible layout and plenty of potential. The home appears to be framed for approximately three to four bedrooms, two full baths, one half bath, a kitchen with dining area, living room with fireplace, dining room, and a den. Much of the upper level has been opened to the studs, making it easier to rework the space and complete the renovation to suit your plans. The exterior already offers several appealing updates, including modern siding, replacement-style windows, and a modern-looking roof. The property is located in Terryville near Lake Winfield Recreation Area, Terryville center, Route 6, local shopping, dining, and simple access toward Route 8. The property is believed to be connected to public sewer and serviced by a private well. Utility information has not been verified. The home is being sold strictly as-is and will require renovation. Buyer and buyer's agent are responsible for all due diligence and for independently verifying utilities, permits, room configuration, square footage, mechanical systems, property condition, and all other information.

6 Scott 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.