Wolcott Homes under $250,000

Welcome to Wolcott, Connecticut – a charming town nestled in the heart of New Haven County. Known for its friendly atmosphere and picturesque landscapes, Wolcott offers a perfect blend of suburban tranquility and easy access to urban amenities. With a rich history dating back to the 18th century, this vibrant community is characterized by its welcoming neighborhoods, lush parks, and a strong sense of local pride.

For those seeking an affordable entry into homeownership, Wolcott is a hidden gem with a variety of homes available for under $250,000. This affordability makes it an ideal choice for first-time buyers, families, and anyone looking to invest in a thriving community without breaking the bank. From cozy single-family homes to charming townhouses, there’s something for everyone in Wolcott’s real estate market.

Residents enjoy an array of local amenities, including top-rated schools, diverse dining options, and recreational activities that cater to all ages. The town’s commitment to maintaining beautiful parks and outdoor spaces makes it easy to enjoy the great Connecticut outdoors, whether you’re hiking, biking, or simply enjoying a picnic with loved ones.

With its strong sense of community, excellent schools, and affordable housing options, Wolcott is the perfect place to call home. Discover the charm of this delightful town and explore the wonderful opportunities that await you in the Wolcott real estate market. Your dream home is just around the corner!

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

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