Cheshire Real Estate

Homes for Sale with a Pool in Cheshire, CT

Welcome to your dedicated resource for homes for sale with a pool in Cheshire, 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 Cheshire, 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.

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All Homes for Sale with a Pool in Cheshire, CT

$1,379,000
5 Beds ⋅ 5 Baths ⋅ 24202325 MLS
Discover this truly exceptional custom Colonial home, distinguished by its thoughtful design, custom millwork, architectural details, and masterful craftsmanship both inside and out, situated on a desirable 2.37 acres corner lot in one of South Cheshire's most sought-after areas. Custom wrought iron gates welcome you into this warm, inviting home, flooded with natural light from the abundant large windows, skylights, and French doors. The heart of the home is the beautifully remodeled kitchen, with its expansive center island offering both exceptional functionality and a wonderful gathering space. The kitchen flows into the spacious family room which provides easy access to the covered porch, allowing effortless, comfortable daily living and entertaining. The first-floor primary bedroom provides convenience and privacy, while three large bedrooms upstairs offer generous space for all. Enjoy year-round sunshine in both the four-season terrace room and the separate sunroom, that bring the outdoors in. Versatile finished space with a full bath above the garage, offers possibilities for home offices, studio, recreation room, and more. The exceptional outdoor setting offers a resort-like experience, the covered rear porch featuring a raised cedar ceiling, skylights, and terracotta tile, provides an inviting gathering space. Follow the path through the gardens to the heated in-ground Gunite swimming pool and hot tub, creating your own retreat for relaxation and entertaining!

885 S Brooksvale Rd, Cheshire
$880,000
4 Beds ⋅ 4 Baths ⋅ 24194251 MLS
Welcome to this stately 3,855 square-foot brick Colonial, perfectly situated on a beautifully level lot in a lovely neighborhood. This spacious 4-5 bedroom home offers timeless elegance and exceptional amenities designed for comfortable living and effortless entertaining. Inside, you'll find gleaming hardwood floors throughout most of the main level and a thoughtfully designed floor plan featuring a large eat-in kitchen with abundant cabinetry and workspace, ideal for everyday living and hosting family and friends. The home also features a spacious great room, perfect for gathering and relaxing, as well as a private home office that provides an ideal space for remote work or study. The convenience of an upper-level laundry room adds ease to daily living. Central air conditioning enhances comfort throughout the home. Step outside to your own private backyard retreat! Enjoy summers in the heated in-ground pool with an attached spa, relax on the expansive patio, or entertain guests in the beautifully landscaped outdoor space. An underground sprinkler helps keep the grounds lush and vibrant with ease. Completing this exceptional property is an attached 3-car garage, providing ample room for vehicles, storage and hobbies. Combining classic Colonial charm with outstanding indoor and outdoor spaces, this home offers the perfect blend of luxury, comfort and functionality.

570 Riverside Dr, Cheshire
$799,900
4 Beds ⋅ 3 Baths ⋅ 24200079 MLS
All the benefits of new construction but none of the wait! This very lightly lived-in 2020 Colonial has all the bells & whistles. Soaring ceilings, open modern floor plan, finished basement, fully fenced back yard, in ground heated pool (2025) & pool house all set in a loop street neighborhood close to so many amenities. Enjoy Bartlem Park, the Linear Trail, coffee shops, events on the Green, the Library- the list is endless. Fall in love from the first glimpse of this 4 bedroom 2.5 bath home with its white vinyl siding, stone accents, stone footpath & black windows. Dinner parties are a dream with your ample counter space, gas range & vent, side bar area, wine cooler & pantry, opening to the expansive Great Room with fireplace. Serve in the morning room that opens to the oversized patio area with firepit overlooking your heated, saltwater inground pool. Keep the party going at the pool house ( has electricity). When work beckons you have a study on the main floor (that could also double as a formal dining room/living room). Upstairs, your spacious primary bedroom with large walk in closet is en suite with double sink vanity & stall shower. 3 generously sized guest bedrooms with great closet space, a full bathroom & sizeable laundry room with sink finish the 2nd floor. You also have a finished basement for gym, work or play, & an oversized, Wi-Fi-enabled garage w/flake epoxy finish (with interior access AND backyard access). No detail forgotten in this beauty! Come visit!

352 Patton Dr, Cheshire
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