Fairfield, CT Homes for Sale with Pool

Welcome to one of Greenfield Hill's most distinguished residences-an extraordinary 9,700+ sq. ft. Colonial estate nestled on 2 pristine acres in one of Fairfield's most prestigious enclaves. This 5-6 bedroom architectural masterpiece combines timeless elegance with modern luxury, offering an unparalleled lifestyle just moments from town. From first look, the home's unrivaled curb appeal

Michael Debiase Keller Williams Realty

Rare beach area gem that checks ALL the boxes! With almost 5,000 square feet of living space on a rare and very private .43-acre lot, this highly custom home features a heated saltwater pool, spa/hot tub, 4-floor elevator, and so many high-end amenities. With an exceptionally wide footprint, this home offers 5-6 bedrooms, 4.5 bathrooms, 9-foot ceilings, front and back decks, a full-house

Ava Fisher Coldwell Banker Realty

Luxury Living on the Fairfield/Westport Border Set in the heart of Greenfield Hill, this exceptional 6-bedroom, 8-bath estate offers a rare combination of privacy, elegance, and resort-style amenities-just minutes from the Post Road and 50 miles from NYC. Thoughtfully positioned on the Fairfield/Westport line, the residence features expansive, sun-filled interiors ideal for everyday living and

Andrew Whiteley Brown Harris Stevens

Lions Gate: No need to move to the south of France as this extraordinary residence is right here in coveted Fairfield. Enter through grand gates into a world of privacy where character, convenience, security & serenity magically meet. Magazine-worthy grounds are the soul of the estate-lush, expansive, & exquisitely curated. With a shimmering pool, spectacular California Redwood Pool House with

Julie Vanderblue Higgins Group Real Estate

Located in the heart of Greenfield Hill at the top of Bronson Road, this iconic Connecticut estate sits on 2+ beautifully landscaped acres with distant water views of Long Island Sound. Across from a majestically developed family and horse-farm compound and outside the historic district, this home blends old-world charm with modern comforts. Originally built in 1844 and significantly expanded and

Tara Hawley Coldwell Banker Realty

Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with

Helene Salerno Preoh, LLC

Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with

Helene Salerno Preoh, LLC

Welcome to the pinnacle of luxury coastal living at 1008 Fairfield Beach Road- where modern luxury meets coastal elegance. Presented by one of Fairfield County's premier celebrity developers, this extraordinary new construction beach home offers an unparalleled lifestyle with panoramic, unobstructed views of the Long Island Sound with jaw-dropping sunsets. Stand out in the neighborhood with one

Valerie Alvarez Higgins Group Real Estate

Refined living awaits on Boxwood Lane, a prime Hunt Club cul-de-sac featuring tranquil private entrances to stately colonial style homes. From its cobblestone-lined, semi-circular driveway to the backyard pool and bluestone patio oasis, the grounds of 5 Boxwood Lane are simply spectacular. The home itself stands apart, meticulously designed with exquisite details and custom amenities. Four

Karen Scott Compass Connecticut, LLC

Design Your Dream Home with an Award-Winning Builder Step into a world of elegance and sophistication with a soon-to-be-built 6,600 sq. ft. masterpiece by Coastal Luxury Homes. Known for their innovative designs, sleek modern lines, and unparalleled craftsmanship, Coastal Luxury Homes has earned a reputation for creating some of the most sought-after residences. With a focus on prime location,

Annie Klyver Higgins Group Real Estate

Move right in to this beautiful 4 bedroom, 4 bath Garrett Wilson colonial on a quiet street in Fairfield's desirable University area. Set on a flat landscaped property, this home offers the perfect combination of style, comfort and convenience. Just minutes to town, train and Riverfield school. The spacious white kitchen opens into the family room with quartz countertops, stainless steel

Lois Lipow William Raveis Real Estate

Welcome to 545 Shrub Oak Lane, an expanded Colonial on 2 private acres in Greenfield Hill. This home sits on a beautifully flat front yard that enhances its curb appeal. Fully renovated in 2012, the family room and oversized kitchen is the heart of the home. The custom designed kitchen has an 10 foot mahogany island with granite countertops, walk-in panty, and mahogany wood framed glass doors

Christine Howard William Raveis Real Estate

Mill Gate House- Rooted in 1930's charm, reimagined for modern living. This classic Center Hall Colonial in coveted Sturges Park offers 4 bedrooms, 3.5-baths and 3000 sq ft of timeless character and everyday ease, rich with architectural details, fresh updates and welcoming spaces. The gourmet kitchen features Carrara marble countertops, stainless appliances and informal dining flanked by French

Lynn Dolan William Pitt Sotheby's Int'l

Welcome to Blue Bell Lane! This gracious 4-bedroom Colonial, nestled in a picturesque neighborhood offers a perfect blend of classic architecture and resort-style amenities. The outdoor paradise includes a gorgeous heated gunite pool with spa and waterfall feature surrounded by a spacious patio for relaxing, dining, and entertaining. The full-size Har Tru tennis court is every tennis lovers

Gezime Ajro Higgins Group Real Estate

Set on 2.98 private acres at the end of a cul-de-sac in coveted Greenfield Hill, this elegant 4627+ SF Colonial offers the perfect blend of luxury, space, and functionality. From the grand 2-story foyer to the exquisite crown moldings, every detail exudes timeless sophistication. Designed for entertaining, the home features a gracious flow with expansive living and gathering spaces, a gourmet

Elizabeth Tritschler William Raveis Real Estate

Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A

Andrew Whiteley Brown Harris Stevens

Sprawling ten room ranch style residence offering 3 acres on a prime estate street in Greenfield Hill. This stately home is discreetly positioned behind a brick wall and approached by a sweeping circular drive creating a grand sense of arrival. Inside this impressive home discover a striking Indoor Pool housed in its own sun lit pavilion. This dramatic recreation space adjoins the Kitchen and

Paul Triantafel William Pitt Sotheby's Int'l

Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every

Elizabeth Tritschler William Raveis Real Estate

Back on the market as of August 22,2025.This Ranch has over $720,000 spent transforming the interior & exterior with feature like an In-Ground pool with slide, 1,513 square feet of finished lower level possibility for an In-Law & 1,190 square foot garage including a hydraulics lift housing 4 cars and only 3 steps from the garage into the Kitchen. All the schools are close with North Stratfield

Paul Ferreira RE/MAX Right Choice

Surrounded by stone walls, this storied, spectacular and private 38.91-acre Greenfield Hill country compound has had a stunning top-level transformation, creating a one of a kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was restored and expanded to incorporate 7 bedrooms and 7 full baths, all with views over the

Leslie Razook William Pitt Sotheby's Int'l

Welcome to Summer Tree Gardens, an extraordinary stately home nestled on over 2 acres of meticulously maintained grounds in the prestigious Greenfield Hill neighborhood of Fairfield, CT. This expansive 7,269 sq. ft. home boasts 5 en-suite bedrooms, 8.5 baths, and an array of luxurious features that blend timeless elegance with modern updates. The home was built by builder Christer Krook. Step

Ken Osborn Higgins Group Bedford Square

Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding

Andrew Whiteley Brown Harris Stevens

"Pebbles" | Iconic Sasco Hill Estate Timeless Design. Storied Past. Unrivaled Views. A distinguished Georgian Revival estate set on nearly 3 acres, the largest lot along this coveted stretch of Sasco Hill. With sweeping, unobstructed views of the Country Club of Fairfield, Southport Harbor, Long Island Sound, and the Manhattan skyline, this iconic property offers an extraordinary blend of

Wendy Ryan Brown Harris Stevens

Discover your private sanctuary at the end of a serene cul-de-sac in Greenfield Hill. This country compound spans 4.5 picturesque acres, enveloping a French-inspired main house with 6 BRs, 4.2 baths, and an enchanting English garden. Step into the elegant formal living and dining rooms, both warmed by inviting FPs, setting the stage for memorable moments. The custom gourmet kitchen, designed for

Linna Yuen Coldwell Banker Realty

This is the iconic property everyone is talking about! Introducing an extraordinary new custom residence set in the beloved estate area of Upper Southport near private equestrian facilities and public trails, beaches, restaurants, train, and shopping. Masterfully designed and customized to YOUR every whim with exquisite main house, separate party barn and/or guest house, pool with spa, tennis

Jaclyn Picarillo Higgins Group Bedford Square

You Deserve the Best! Come home each day and unwind by the huge pool or enjoy a game or two of tennis! Come live in the beautiful, quiet community of the Embassy Towne Homes, a unique North End complex of brownstone style townhouses. You'll feel right at home in this spacious unit which has been tastefully remodeled from top to bottom. This unit offers Primary Bedroom suite and 2nd Bedroom with

Aziz Seyal William Raveis Real Estate