Wolcott Homes under $250,000

Welcome to Wolcott, Connecticut—a charming town nestled in the heart of New Haven County! Known for its picturesque landscapes and friendly community, Wolcott offers a perfect blend of suburban tranquility and convenient access to urban amenities. With its rich history, beautiful parks, and a variety of recreational opportunities, it’s no wonder that many families and individuals are drawn to this welcoming town.

Wolcott boasts a diverse range of homes, and for those looking for affordability without sacrificing quality, there are delightful options available for under $250,000. Whether you’re a first-time homebuyer, a growing family, or someone looking to downsize, you’ll find charming single-family homes, cozy townhouses, and even some inviting condos in this price range. These properties often feature spacious yards, modern amenities, and the potential for personalization, allowing you to create your dream home.

In addition to its attractive housing market, Wolcott is known for its excellent schools and vibrant local community. Residents enjoy a variety of parks, walking trails, and recreational facilities, making it easy to embrace an active lifestyle. Plus, with easy access to major highways, you’re just a short drive away from the bustling cities of Waterbury and New Haven, where you can explore a wealth of dining, shopping, and entertainment options.

Discover the charm of Wolcott and explore the affordable housing opportunities that await you. Your dream home in this delightful town is just a visit away!

Newest Wolcott Homes under $250,000

$239,000

3 Beds ⋅ 1 Baths ⋅ 24210233 MLS

Ranch with 3 Bedrooms and 1 Full Bath, 1 Car Garage underneath, Forced W/Air and Central air, Nice Sized Covered Rear Deck, Home also has a Nice Sized Rear yard, Home is being sold As-IS

48 Coach Dr, Wolcott

$249,900

2 Beds ⋅ 1 Baths ⋅ 24208971 MLS ⋅ Lake Hills Village BLDG.

Welcome to this inviting 2-bedroom Ranch style condominium offering comfort, style and a wonderful setting. The remodeled kitchen features quartz countertops, updated cabinetry and appliances. Relax in the spacious living room with a cozy fireplace, perfect for quiet evenings at home. This lovely condo also offers two comfortable bedrooms and a full bath. Step through the sliding glass door onto the deck where you can sit back, unwind and enjoy the beautiful views overlooking the lake. A wonderful opportunity to enjoy Ranch-style living, modern updates and a peaceful lakeside setting. Must be owner occupied for a minimum of 2 years before being able to rent the unit.

264 Lyman Rd Unit 1-12, Wolcott

$199,999

2 Beds ⋅ 1 Baths ⋅ 24206334 MLS ⋅ Lake Hills Village BLDG.

Welcome to this PICTURE PERFECT Affordable, beautifully remodeled two-bedroom townhouse with stunning lake views! Enjoy peace and serenity in this picture-perfect home featuring in-unit laundry and a comfortable, updated interior. Perfect for a first-time buyer or someone looking to downsize. The HOA INCLUDES private lake access, heat, hot water, and much more, making this home both convenient and affordable. A wonderful opportunity you won't want to miss!

264 Lyman Rd Unit 1-4, Wolcott

$200,000

4 Beds ⋅ 1 Baths ⋅ 24202653 MLS

BEST AND FINAL DUE BY 8 PM ON 9/5/26. NO EXCEPTIONS 4bedroom, 1bath home offering great potential and a spacious, flat yard perfect for outdoor enjoyment. This property needs a little love and is being sold as is, providing an excellent opportunity for buyers looking to customize and add value. A solid layout and generous lot make this a standout option for investors or homeowners seeking a project with upside. Pictures coming

185 Todd Rd, Wolcott

$199,900

2 Beds ⋅ 1 Baths ⋅ 24195811 MLS

Great opportunity to build equity on a quiet cul-de-sac in Wolcott. This 2-bedroom, 1-bath ranch sits on a generous 0.46-acre lot, offering plenty of outdoor space and privacy. The home features 792 square feet of living space on the main level plus a convenient under-house garage for parking or extra storage. Bring your design ideas and updates to maximize this property's true potential. Ideal for investors, contractors, or handy buyers looking to customize their next home. Schedule your showing today to explore the possibilities.

66 Chesterfield Ave, Wolcott

$249,900

2 Beds ⋅ 1 Baths ⋅ 24190310 MLS ⋅ Lake Hills Village BLDG.

Lakefront Condo Living at its Best! Enjoy the beauty and tranquility of lakeside living in this charming 2 bedroom condo. Featuring bright and inviting living room, dining room and a well appointed kitchen, updated full bath, this condo offers comfort and convenience in a picturesque setting. Step outside and embrace the lake lifestyle! Spend your days swimming, kayaking, or paddle boating right from your community. This condo is the perfect place to relax and enjoy nature. Heat & Hot water included in common charges. Must be owner occupied for two years before being allowed to rent.

264 Lyman Rd Unit 1-1, Wolcott

$189,500

2 Beds ⋅ 1 Baths ⋅ 24183255 MLS ⋅ Lake Hills Village BLDG.

Waterfront living on scenic Chestnut Hill Reservoir! Whether you're an avid angler, nature enthusiast, or simply looking for a peaceful retreat, this beautifully updated 2-bedroom, 1-bath condo is a rare opportunity to enjoy lakefront living in one of Wolcott's most picturesque settings. Step inside to a bright and inviting living and dining area featuring soaring cathedral ceilings, a cozy wood-burning fireplace, and sliding glass doors leading to your private covered deck with tranquil water views. The kitchen features ample cabinetry, granite tile flooring, and comes fully applianced, creating a functional and welcoming space for everyday living. Two spacious bedrooms provide generous closet space, while the updated full bath, large attic for additional storage, and energy-efficient windows add comfort and convenience. Recent improvements include a newer boiler and a new roof (2026). Outdoor living truly sets this home apart. Enjoy fishing, swimming, kayaking, canoeing, paddle boarding, or relaxing by the water from your private dock. A boathouse provides additional storage, and the garden area, breezeway, covered deck, and guest parking add to the property's appeal. Conveniently located near shopping, dining, and everyday amenities, with easy access to Route 69, Route 8, and I-84.

264 Lyman Rd Unit 2-12, Wolcott

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.