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

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

Prepare to be wowed by this extraordinary estate featuring six bedrooms and ten-and-a-half bathrooms, spanning four meticulously designed floors. Enter through a breathtaking two-story grand foyer, leading into beautifully appointed formal and informal rooms perfect for entertaining and a gourmet kitchen that any discerning chef would envy. The luxurious primary suite serves as a private

Anissa Paolillo Redfin Corporation

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

Don't let the address fool you-Sturges Highway is a peaceful, tree-lined street in Westport's sought-after lower-tax area, offering privacy, serenity, and convenience just minutes from town and schools.With NEW MECHANICALS including a NEW FURNACE, NEW ROTH OIL TANK, an NEW 80 GALLON HOT WATER HEATER, and a WHOLE HOUSE GENERATOR this home is move-in ready with peace of mind.This 8,000+ sq ft home

Lainie Floyd William Pitt Sotheby's Int'l

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

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

A Must-See Gem only 1 mile from Sacred Heart University Don't miss this beautifully updated, move-in-ready home that truly has it all-including a sparkling pool! Step inside to a warm and inviting living room featuring a cozy wood-burning fireplace and a sunlit bay window. The spacious layout boasts three generously sized bedrooms, each with walk-in closets, and a stunning eat-in kitchen

David Hughes Century 21 AllPoints Realty

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

Live the ultimate coastal lifestyle in this sensational 5-6 bedroom, 4.5 bathroom Nantucket-style Colonial w/brand new Gunite pool. Set on an oversized, wide lot, this home was recently reimagined by one of Fairfield County's most acclaimed interior designers. Sun-flooded w/9' ceilings & a breezy beach-inspired layout, every detail feels custom & elevated: coffered ceilings, transom doorways,

Kate Cacciatore William Raveis Real Estate

Meticulously restored, this one-of-a-kind property masterfully blends timeless character with luxurious modern updates. The home's main floor is open and inviting, featuring restored wide-plank floors, original wood beams, and designer lighting throughout. The heart of the home is the stunning kitchen with crisp white brick, full-paneled refrigerator and freezer, hidden pantry, oversized island

Jennifer Thomas-Heath Houlihan Lawrence

Sprawling ten room ranch style residence offering three 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

Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury

Akenmisire Musa The Agency

True Ranch, only 3 steps from the kitchen into the garage with over $720,000 spent transforming the interior & exterior boasting an In-Ground pool with slide ( 33x16 ), 1,513 square ft finished lower level, possible In-Law & 1,190 square ft Garage housing 4 cars, including a hydraulics lift. MAIN LEVEL FEATURES { 296 square ft Eat in Kitchen : 297 square ft Living room with fireplace : 290

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

Perfectly sited on a quiet cul-de-sac in the Greenfield Hill neighborhood, this exquisite farmhouse-style home offers over 5,000 sq ft of elegant living space on a spectacular, level property. The classic character and contemporary elegance defines this home offering 5 bedrooms, 5 baths, custom millwork, refined designer details and exceptional outdoor living. Step into a gracious foyer flanked

Jennifer Lockwood Coldwell Banker Realty

Charming Colonial in Lake Mohegan - Move-In Ready & Beautifully Updated! This updated Colonial in the desirable Lake Mohegan area is ready for you to move in! Freshly painted throughout with newly refinished hardwood floors, this home offers both classic charm and modern updates. A gracious foyer leads into the Living Room and Dining Room, with French doors opening to a bright Sunroom. The

Jonathan Deak Coldwell Banker Realty

Welcome to your prestigious estate in Fairfield's coveted Greenfield Hill. Set back from the road, with fresh paint and new roof, this meticulously maintained elegant residence merges timeless design with modern luxury across 4,606SF of refined living space on a sprawling 2.1AC. Professional gardens and lawns provide privacy. Enjoy music from the sound system as you find hardwood floors sweeping

James Barone Compass Connecticut, LLC

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

Nestled in a sought-after community, this charming townhouse offers the perfect blend of convenience and comfort. Ideally located near two universities, grocery stores, shopping, restaurants, town beaches, and with easy access to major highways, this home is perfect for those looking for both accessibility and a peaceful setting. The first floor features a well-appointed kitchen that flows into a

Katerina Hendrickson Coldwell Banker Realty

Discover your private sanctuary at the end of a serene cul-de-sac in Greenfield Hill. This country compound spans 4.5 acres, enveloping a French-inspired main house with 6 BRs, 4.2 baths, and an enchanting English garden. Go 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 living, opens

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

Must See! Rare Find! One of the Largest Units in the complex! Luxury High Rise Condo located in the coveted "Inwood" Complex. Professionally designed by the late artist "Harry L. Green". Snuggled on the Bridgeport/Fairfield Boarder, this unit gives you everything you've been looking for. From the gated entry to the 24-hour doorman... you will not be disappointed. Enjoy semi-private elevator

Daniel D. Thomas D. Thomas Homes

Wonderful opportunity to own this spacious two-bedroom condo with views of the Long Island Sound. This pretty home features a great room with high ceilings and a wall of glass overlooking the terrace and stunning view. The sunny kitchen has lots of storage, a laundry room and an eating area with sliders on to the terrace. In addition, there are two large bedrooms. The primary suite has a walk-in

Marlene Fischer William Raveis Real Estate

You. Will. Fall. In. Love! Luxury High Rise Condo located in the coveted "Inwood" Complex. Snuggled on the Bridgeport/Fairfield Boarder, this unit gives you everything you've been looking for. From the gated entry to the 24-hour doorman... you will not be disappointed. Enjoy semi-private elevator access to your unit (only two units per floor). Secure covered Parking. And an amazing hotel like

Daniel D. Thomas D. Thomas Homes

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