Fairfield, CT Homes for Sale with Pool

*Offers Due 7/26 at 5PM* Timeless luxury meets exceptional craftsmanship at 98 Banks Place, where a meticulous restoration & rebuild, completed in 2017, transformed an 1830 Greek Revival into a home offering the comfort of new construction while preserving the soul, warmth, & character only a home of this era can provide. Original floors, brick, timbers, custom windows, reclaimed hardware, &

Shoshana Snyder Compass Connecticut, LLC

Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among

Andrew Whiteley Brown Harris Stevens

This offering is for 4800 Congress St, a one of a kind estate consists of main residence on 10.92 acres, pool, barn pool house/gym, heated paddle court, and an office pavilion. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street,offering seclusion with proximity to NYC. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century

Leslie Razook William Pitt Sotheby's Int'l

775 Sasco Hill Road is an extraordinary estate where timeless elegance meets modern luxury. Impeccably renovated and beautifully curated by the current owners, this sophisticated residence offers three full levels of refined living set across five private, park-like acres. A dramatic cathedral foyer and soaring 9-foot ceilings create an immediate sense of scale and light, while the thoughtfully

Suzy Ryan William Raveis Real Estate

Welcome to this beautifully maintained University Area raised ranch, offering four bedrooms and two and a half baths across two well designed levels. The main level features a spacious living room, formal dining room, and newer eat-in kitchen with granite countertops and stainless steel appliances, a primary suite with a full bath and his and her closets, plus exceptional closet space throughout

Tara Hawley Coldwell Banker Realty

This first-floor, 2BR, 2-bath unit is in a quiet Southport complex with in-ground pool. Just a short walk to the grocery store, shopping, train, public bus line, bank, and more. The updated unit features a living room with vinyl plank flooring, ceiling fan, wood-burning fireplace with raised marble hearth, plus attractive millwork. Sliding glass doors open to a covered porch with lawn space for

Sherri Steeneck Higgins Group Real Estate

This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With

Lisa Hartmann William Pitt Sotheby's Int'l

As you enter 80 Governors Lane down a private driveway, discover an 8.5-acre estate blending timeless elegance with serene privacy. This circa 1933 farmhouse, designed by architect Jack Franzen and beautifully restored, features wide plank black walnut floors, exposed beams, and a bread oven fireplace. Six spacious bedrooms include a luxurious Primary Suite with vaulted ceilings, carved mantle

Lis Reed Coldwell Banker Realty

Don't miss out on this beautiful, spacious 3-level townhouse featuring 2 bedrooms and 2.5 bathrooms! The main level offers a welcoming open-concept living and dining area with a cozy fireplace, a convenient half bath, and sliding glass doors leading to a private enclosed deck-the perfect spot to enjoy your morning coffee or unwind after a long day. Upstairs, you'll find a spacious primary suite

Shirley Gale-Martinez eXp Realty

Nestled on a private lane, this Southport luxury estate offers a pin-drop quiet setting just minutes from Southport Village, Southport Harbor, the Southport train station, I-95, and the Merritt Parkway. Set on over two level acres, it blends tranquility and convenience. The home features six bedrooms, including a gracious first-floor primary suite with a fireplace, dual spa-like bathrooms,

Amanda Heyn William Raveis Real Estate

Welcome to 3080 Sturges - Fully Renovated Home set on 2.44 private acres in Fairfield's Greenfield Hill enclave on the Westport border. Offering a Westport mailing address together with Fairfield's acclaimed schools and amenities, this 7,317-square-foot modern residence blends architectural scale with contemporary comfort and luxury. A dramatic two-story foyer introduces interiors defined by

Ryan Sullivan Berkshire Hathaway NE Prop.

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

Spectacular custom estate built by Andy Frank in prestigious Greenfield Hill featuring a rare first-floor primary suite w/fireplace, spacious WIC, luxurious spa bath & vaulted ceiling -- a true standout for convenient main-level living. Set on over 2 magnificent landscaped acres on a double cul-de-sac, this home delivers resort-style living w/exceptional privacy. Outside, an oversized free-form

Veronica Monahan Compass Connecticut, LLC

Set within The Ridge in Greenfield Hill, Fairfield's gated residential community, this residence has been completely rebuilt and thoughtfully reimagined with the scale and finish of new construction. Spanning over 8,000 sq ft, the home offers four bedrooms and six full and two half baths, with wide plank oak floors, multiple fireplaces, and expansive windows that frame tranquil pond views. A

Erin Melson The Agency

Stunning new construction. Extraordinary design, finishes and craftsmanship with meticulous attention to detail. Taxes will be determined upon completion.

Susan Tracy Higgins Group Bedford Square

This is why so many people fall in love with Southport. Set on an extraordinary .83-acre parcel in the heart of the Village, this circa 1874 residence captures the charm, character, and lifestyle that have made Southport one of New England's most treasured coastal communities. Approached by a long drive and set well back from Harbor Road, the home enjoys a level of privacy rarely found in the

Wendy Ryan Brown Harris Stevens

The Ultimate East Coast Sanctuary, Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning buyers who demand seclusion with proximity to NYC. This 38.91-acre compound is a one-of-a-kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of

Leslie Razook William Pitt Sotheby's Int'l

Beautifully updated and impeccably maintained townhome in sought-after Woodfield Village. Hardwood floors throughout, an updated kitchen, and a cozy fireplace create warm and inviting living spaces, while beautiful seasonal sunrise and sunset views add to the home's appeal. Enjoy a private deck off the family room and a private balcony off the primary suite. Both bedrooms feature walk-in closets

Amie Belile William Raveis Real Estate

Welcome to 166 Glengarry Road, a beautifully maintained end-unit townhouse in Fairfield's sought-after Woodfield Village community. Offering 3 bedrooms, 3 full baths, 1 half bath,and a versatile floor plan, this move-in-ready home combines comfort, space, and convenience. Freshly painted throughout and featuring refinished hardwood floors, the home is filled with natural light. The spacious

Myles Simon MBA Realty, LLC

1008 Fairfield Beach Road- A Masterpiece on Fairfield's Iconic Coastline. 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 of the

Valerie Alvarez Serhant Connecticut, LLC

Your new fully custom near beach luxury residence is ready for you now... Introducing "White Birch", a masterfully executed collaboration between Fairfield County's premier Architect, Builder, & Designer, sets a new benchmark for bespoke coastal living and the effortless estate lifestyle. Every detail has been thoughtfully curated, every finish intentionally elevated, every inch built with

Jaclyn Picarillo Higgins Group Bedford Square

Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 688 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury

Jaclyn Picarillo Higgins Group Bedford Square

Nestled at the end of a cul-de-sac in the beautiful Greenfield Hill neighborhood, this fully updated and renovated home sits on a private 2.4-acre lot and offers Fairfield living at its finest. This 5-bedroom home, with four full and two half bathrooms, boasts spacious interiors, an open floor plan, all-new finishes, and a brand-new primary bedroom suite addition above a three-car garage. The

Danielle Baleeiro Realty ONE Group Connect

2177 Cross Hwy welcomes you home. This extensively renovated iconic contemporary awaits your personal touches. The blending of dramatic architecture with everyday comfort, offering nearly 4,000 sq ft of functional living space designed for gathering, relaxing and entertaining. Soaring 22' ceilings, oversized windows and park-like views fill the main living area with light, while a striking

JaKeith Action Jackson ASJ Realty Partners

Filled with natural light and ideally positioned as a second floor end unit, this inviting ranch style condominium offers a spacious layout in one of Fairfield's most desirable communities. The living room is anchored by a wood burning fireplace and oversized windows, creating a warm and welcoming space that flows into the dining area, perfect for everyday living or entertaining. The eat in

Amie Belile William Raveis Real Estate

Welcome to 91 Lockwood Road, where modern farmhouse charm meets timeless comfort in one of Stratfield's most sought-after neighborhoods. Beautifully renovated, this exceptional home offers the perfect blend of style, functionality, and everyday living. Designed for today's lifestyle, the home features 5-6 bedrooms, 3 full baths, and 1 half bath, with bright, versatile living spaces that offer

Susan Bento Distinct Realty

Sophisticated brownstone living awaits in this beautifully maintained end-unit townhouse offering over 2,700 square feet of thoughtfully designed living space across three finished levels. Featuring three bedrooms plus a spacious flex room that can easily serve as a fourth bedroom, home office, or media room, this exceptional residence combines the spaciousness of a single-family home with the

Fred DeMatteo William Raveis Real Estate

Are you dreaming of an estate property? Something a bit more than the generic flat acre on a cul de sac? How do two acres on the Aspetuck River sound to you? With views from your bedroom? The sounds of a waterfall next door lulling you to sleep? Having sunnies tickle your toes in the summertime? Maybe a bit of fly fishing for trout? Or perhaps some paddleboarding? Yes, of course, there's a 20x40

Maryann Levanti Higgins Group Bedford Square

Welcome to the Brownstones at 3300 Park Avenue. This beautifully maintained townhouse is move-in ready, offering three spacious stories plus a fully finished basement with additional storage. Ideally located directly across from Fairfield, this condo features a charming private front patio as well as a large private back patio

Laura Parkington William Raveis Real Estate

Tucked away on a quiet cul de sac in the desirable Hunt Club area of Long Lots in Westport is a new construction lux home from CCO Habitats. 3 levels of finished living space with 10 foot ceilings on the 1st floor give an amazing sense of openness, as well as better functionality than 4 level homes. Think about it. Who really wants to walk up to the third floor every day? That's right; no one.

Maryann Levanti Higgins Group Bedford Square