Woodbridge Real Estate

Homes for Sale with a Pool in Woodbridge, CT

Welcome to your dedicated resource for homes for sale with a pool in Woodbridge, 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 Woodbridge, 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 Woodbridge, CT

$3,200,000
4 Beds ⋅ 4 Baths ⋅ 24194459 MLS
Offered Fully Furnished. Set within nearly three private acres of mature woodland, Winnick Retreat is a reimagined mid-century modern residence where architecture, landscape and everyday life exist in quiet balance. Originally built in 1962 designed by Yale's very own Herbert S. Newman, the home is defined by its low horizontal profile, deep roof planes, clerestory windows and expansive walls of glass. A dramatic two-story central atrium draws natural light through the interior, while nearly every principal room maintains a direct visual connection to the surrounding trees, gardens and changing seasons.Inside, approximately 4,134 square feet of living space offers four bedrooms and three-and-one-half bathrooms. Warm wood, natural stone and glass create interiors that feel composed rather than formal. The renovated primary suite, custom kitchen and carefully updated living spaces respect the home's architectural character while supporting contemporary life. The property's recent transformation extends far beyond the interior. Landscaped grounds now unfold as a sequence of private experiences: a swimming pool with fire and water features, pool cabana, barrel sauna, fire-pit courtyard, outdoor fireplace and Har-Tru tennis court. Terraces, balconies and garden paths connect living spaces to the natural setting. Recreation and restoration become part of the daily rhythm. Mornings begin with a warm drink on the balcony underneath the tree canopy.

17 Pine Ridge Rd, Woodbridge
$1,089,000
4 Beds ⋅ 4 Baths ⋅ 24161318 MLS
Hidden Gem in Woodbridge - Where Nature, Comfort & Elegance Align Welcome to a private paradise tucked away on a peaceful, tree-lined road in sought-after Woodbridge. Set on 1.6 beautifully landscaped acres, this exceptional home is bursting with character, charm, and over $100,000 in thoughtful updates (see MLS documents for full list). From the long private driveway to the 2-car garage, carport, and oversized deck overlooking your own in-ground pool, every detail has been designed to enhance your lifestyle-indoors and out. Step inside to discover 9 inviting rooms, including 4 spacious bedrooms (some with walk-in closets), and 3 full bathrooms. The main level boasts gleaming new hardwood floors, an updated kitchen, and two sun-soaked great rooms where natural light pours in and picture-perfect views stretch across the backyard oasis. Upstairs, cozy wall-to-wall carpeting makes the bedrooms feel warm and restful, while downstairs, the open flow is perfect for entertaining. Whether you're hosting a sunset dinner on the deck, enjoying morning coffee surrounded by fruit trees and gardens, or cooling off in the pool after a long day-this home makes every day feel like a vacation. features include a refreshing outdoor shower, a carport for extra parking or storage, and a sense of tranquil seclusion that's hard to find-yet just minutes from everything New Haven County has to offer. This is more than just a home-it's a story waiting to be lived. Welcome to your Woodbridge

11 Ariel Rd, Woodbridge
$950,000
3 Beds ⋅ 3 Baths ⋅ 24193957 MLS
Rarely does a MID-CENTURY MODERN home of this caliber become available. Privately nestled among mature trees in an extraordinary lakefront setting, this architecturally significant residence was thoughtfully designed to capture its natural surroundings, offering exceptional privacy, breathtaking views, and seamless indoor-outdoor living. Walls of glass, expansive sliders, and dramatic contemporary windows flood the home with natural light while framing the landscape from nearly every room. The spectacular Living Room, the centerpiece of the home, features soaring vaulted ceilings, a striking floor-to-ceiling brick wood-burning fireplace, and an office alcove ideal for remote work or creative pursuits. Flowing effortlessly from the Living Room, the Dining Room and Family Room create an expansive open-concept living space centered around a state-of-the-art custom kitchen equipped with premium La Cornue, Wolf, and Sub-Zero appliances. True to its mid-century design, each of the three bedrooms enjoys an en-suite bath and direct access to the private grounds, creating a unique connection to the surrounding landscape. This three-zone central air-conditioned home overlooks the beautifully landscaped saltwater gunite pool, recently resurfaced and updated with new mechanical systems, as well as professionally designed, park-like grounds. Fully owned solar panels provide excess electricity to offset winter months electric use to bare minimum.

20 Crestview Incl 24 Crestview Dr Drive, Woodbridge
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