Trumbull Real Estate

Homes for Sale with a Pool in Trumbull, CT

Welcome to your dedicated resource for homes for sale with a pool in Trumbull, CT. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Trumbull, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

< Back to all Homes for Sale in Trumbull, CT

Be the First to Know About New Trumbull Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Trumbull Real Estate Map Search

Search by Lifestyle
  Advanced Search   Market Reports   Home Value   Connect

All Homes for Sale with a Pool in Trumbull, CT

$949,900
6 Beds ⋅ 5 Baths ⋅ 24187764 MLS
Exceptional multi-generational living opportunity in the heart of Trumbull! This expansive 4,844 sq. ft. home is perfect for a big family. The main home features 4 bedrooms, 3 full bathrooms, full dining room, living room and kitchen with hardwood floors throughout. In addition there's an extra 1,100+sqft finished walkout basement. The other side of the home is a private legal ADU Designed for comfort and privacy, townhouse style 2 bedrooms 1.5baths with a full kitchen, living room, laundry a private driveway and balcony. The main home also features a spacious attached two-car garage and private backyard complete with an oversized deck area and an in-ground swimming pool, creating the perfect setting for entertaining and outdoor enjoyment. Offering generous living space and a unique layout, this one-of-a-kind property combines functionality, versatility, and endless possibilities.

16 Windy Rdg, Trumbull
$875,000
5 Beds ⋅ 4 Baths ⋅ 24205381 MLS
Perched above the street on a private, landscaped lot, this exceptional custom ranch offers an impressive blend of space, comfort, and resort-style living. Extensive improvements throughout include new hardwood floors, a redesigned kitchen, renovated bathrooms, new lighting, and fresh interior and exterior paint. With over 4,100 sq ft of living space plus a partially finished lower level, the semi open-concept floor plan seamlessly connects the living, dining, and kitchen areas. Vaulted ceilings and skylights fill the home with natural light, creating an inviting setting for both everyday living and entertaining. The showpiece is a private, heated indoor pool housed in an impressive two-story, approximately 900 sq ft cedar room with a diving board and direct access to the patio and backyard. Five spacious bedrooms and 3.5 baths include a private primary suite with an en-suite bath and jetted tub. Additional highlights include a dedicated home gym, 4-car underground garage, solar panels, manicured landscaping, and updated pool equipment. With the major work already completed, this is a rare opportunity to enjoy a turnkey home with exceptional amenities and space for the whole family.

223 Sterling Rd, Trumbull
$859,900
4 Beds ⋅ 4 Baths ⋅ 24163140 MLS
Step into a piece of Trumbull's history with this enchanting, updated Craftsman Cape loc in the highly sought-after Daniels Farm section, close to top-rated schools, parks, shopping, restaurants, & major highways. Originally built by Col. William C. Weeks when Daniels Farm Rd was a rural farm district, this unique home, known as "Kobble Cot," blends historic charm w/ modern comfort & has long been a place where generations gathered & created lasting memories. From the moment you arrive, you'll feel the warmth-relax on the expansive stone front porch, perfect for morning coffee or evening gatherings, then enter through double doors into a grand Great Room featuring exposed beams & a striking stone FP. The formal DR w/ built-in glass shelving flows seamlessly into the living space & opens via French doors to a bright Sunroom overlooking the in-ground pool & patio. The updated Kitchen offers SS appliances, center island, & access to a spacious deck overlooking the landscaped yard. The main level includes a BR, Den, & full Bath, ideal for guests or home office. Upstairs features a Primary Suite w/remodeled bath, 2 add'l BRs, & updated bath w/wood slider door, along w/ charming cottage windows & cedar closet. The fin LL includes a game rm, laundry, 1/2 bath, & walk-out to pool area. The property, once filled w/apple trees where children played and made memories, now offers a spacious yard, in-ground pool, large patio, built-in BBQ, & 2 sheds. Circular drive provides ample parking.

1209 Daniels Farm Rd, Trumbull
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.