Southport, CT Homes for Sale with Acreage

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

Endless opportunities await at this property-whether a buyer envisions their ideal home, a buyer interested in constructing a multigenerational family residence, someone looking to renovate the current home or rebuild and take advantage of the surrounding land, or a builder looking for a new project, this is the perfect place for you, Three individual lots, totaling three secluded acres, are

Harriet Stone William Pitt Sotheby's Int'l

Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community, an exclusive four-lot enclave envisioned and built by Joe Feinleib, founder of Coastal Luxury Homes and one of Fairfield County's most respected builders.This private neighborhood blends timeless architecture with modern luxury. Each custom residence, ranging from 5,000 to 7,500 square feet, plus generous

Julie Vanderblue Higgins Group Real Estate

Coming Spring 2026 - Have you been quietly creating a wishlist of EVERYTHING you want in your next home? This new mini-estate on a preferred Greens Farms cul-de-sac is YOUR EVERYTHING! There will be no reason to leave home - 25 Ellery offers it all including a pool site. The flow of this house is divine. Rooms are spacious, comfortable, and well-thought out for today's lifestyle. Windows are

Jaclyn Picarillo Higgins Group Bedford Square

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 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, architectural

Annie Klyver Higgins Group Real Estate

Welcome to this beautifully crafted new construction home in the heart of Westport, where timeless design and thoughtful details come together to create a luxurious space. From the moment you step inside, you're welcomed by a bright and open floor plan with high ceilings and wide-plank flooring that runs throughout the main living space. Natural light fills every room, highlighting the custom

Sara Santos Coldwell Banker Realty

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

Proposed New Construction, build this beautiful home or let's design your dream home!! 1 acre lot with a brook sets up perfectly for a walk-out basement. Great location close to everything. Quality custom home builder with 25 years experience and over 150 homes built. Existing home to be torn down, taxes shown reflect existing home.

Phil Pedros Philips Real Estate

Storied and superbly restored, 'The Lookout' at 249 Greens Farms Rd blends the grandeur of a 1907 Victorian with todays modern luxury. Privately set among perennial gardens and antique copper beeches, this iconic 16-room residence offers a gracious floor plan with elegant formal spaces, a chefs eat-in kitchen, media room, wine cellar, and inviting family areas. Original architectural details

Kim Harizman Compass Connecticut, LLC

New Construction of a farm house style colonial in the prestigious Greenfield Hill section of Fairfield. Approvals in place for this home on a designated scenic road. 193 feet of frontage plus city water available in the street. This is an excellent opportunity to customize your dream home on a beautiful, cleared and leveled Greenfield Hill lot surrounded by nature, charming New England stone

Mona Cascella William Raveis Real Estate

In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate offers a rare opportunity in one of Fairfield's most coveted locations. Set on more than two acres of beautifully landscaped grounds with distant views of Long Island Sound, the property reflects timeless elegance and a sense of place that is hard to replicate today. Across from a distinguished

Tara Hawley Coldwell Banker Realty

A GREAT OPPORTUNITY TO MOVE IN, EXPAND, OR CREATE YOUR DREAM HOME. Just minutes from downtown Westport, this 3-bedroom, 2-full-bath ranch offers a rare opportunity in a prime location. The home features a bright living and dining area with a wood-burning fireplace, opening into an oversized family room-perfect for entertaining-all with hardwood floors throughout. A central hallway leads to three

Michael Jabick Keller Williams Realty

An extraordinary architectural vision for a location of equal distinction. Top luxury developer/builder, Coastal Luxury Homes is putting the finishing touches on the most impressive floor plan for this choice 1 acre lot in top Greens Farms neighborhood. Breathtakingly stunning public rooms flow seamlessly into inviting and intimate spaces while dramatic floor-to-ceiling windows and doors open to

Jaclyn Picarillo Higgins Group Bedford Square

RARE OPPORTUNITY TO CUSTOMIZE NEW CONSTRUCTION BY COASTAL LUXURY HOMES. PLANS APPROVED & PERMITS IN PLACE. CONSTRUCTION CAN BEGIN IMMEDIATELY, SAVE 6+ MOS ON NEW BUILD TIMELINE. This ultra luxury modern cul-de-sac residence features stucco exterior, DaVinci Boral roof, and expansive windows up to 10ft high. Main level includes luxe chef's kitchen w/ breakfast room opening to the great room with

Jennifer Tanner The Riverside Realty Group

Discover this stunning 6-bedroom single-family home-a modern masterpiece designed for today's lifestyle. Perched on a private cul-de-sac just minutes from downtown Westport, dog parks, beaches, award-winning restaurants, and even a 24-hour CVS for those late-night essentials, this residence perfectly blends convenience with serenity. Step inside and experience Westport luxury redefined-a striking

Nanci Lewis Keller Williams Realty

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 icons 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 Music,

Leslie Razook William Pitt Sotheby's Int'l

Welcome to this beautifully crafted new construction home in the heart of Westport, where timeless design and thoughtful details come together to create a luxurious space. From the moment you step inside, you're welcomed by a bright and open floor plan with high ceilings and wide-plank flooring that runs throughout the main living space. Natural light fills every room, highlighting the custom

Sara Santos Coldwell Banker Realty

From city politics to select suburb - this home offers you the desired change with NYC still within reach. Nestled in Westport's prestigious Greens Farms enclave, this Victorian estate blends timeless character with modern sophistication. Originally built in 1861 and expanded in 2008, it offers over 6,600 sq ft of refined living space on 2.02 serene acres. Enjoy lush lawns, a private pool,

Frank Zilinyi William Raveis Real Estate

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 retreat,

Anissa Paolillo Redfin Corporation

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

Once-in-a-Generation Historic Estate set on a most coveted stretch of Fairfield County's Gold Coast, with a remarkable provenance as a former Bedford family estate. This extraordinary property is a rare offering that blends timeless architecture with iconic waterfront living. With sweeping views of Long Island Sound, the home's stately presence is matched only by its stunning 3.55 acres of

Cyd Hamer William Pitt Sotheby's Int'l

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

Design Your Dream Home with an Award-Winning Builder Step into a world of elegance and sophistication with a soon-to-be-built 6,100 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

This is the second of 2 custom homes, beautifully sited at the end of a private lane in the heart of Greens Farms. Combining classic design with modern detailing by an established local builder of premier residences, this masterfully crafted home is sure to delight even the most discerning buyer. The main level showcases expert millwork and warm white oak accents throughout, flowing from the

Laurie Crouse Coldwell Banker Realty

Classic Greens Farms Colonial - Timeless Elegance Meets Modern Comfort ~ Nestled in one of Westport's most desirable neighborhoods, this beautifully updated Center Hall Colonial offers the perfect blend of timeless charm and modern luxury. Ideally located just minutes from Sherwood Island State Park-with its miles of golden sand beaches, scenic picnic areas, and sweeping views-this home provides

Shalini Madaras Silver Pine Real Estate

Set on over two private acres in the gated community of The Ridge, this stunning estate combines modern comfort with timeless design. Residents enjoy resort-style amenities including a clubhouse, pool, tennis courts, playground, basketball court, private recreation facilities, and 24/7 gate security. Step inside through a soaring vaulted foyer that opens to a sun-filled living room framed by a

Adele Higgins Higgins Group Real Estate

THE BEDFORD HOUSE - Architecturally and historically significant estate in coveted Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's most superb homes. Set on 2.33 acres with a gunite pool/spa, court and a 2400 sq ft barn featuring a 3-car garage, loft & more, the estate blends timeless elegance with modern comfort. Originally built in 1904 and designed by

Leslie Riback Coldwell Banker Realty

Modern elegance meets estate living at 88 Merry Meet Circle, set on 3+ manicured acres in Fairfield's premier gated community, The Ridge. Perfectly positioned where Fairfield meets Westport, this gracious colonial manor offers 5+ bedrooms, 6 full and 2 half baths, and 4 beautifully finished levels-just minutes from vibrant downtowns, beaches, dining, and trains. A grand two-story foyer with a

Erin Bremen melson The Agency

Located in the coveted Greenfield Hill neighborhood, this exceptional property offers the perfect blend of weekend retreat and everyday living, just 60 miles from Manhattan. Set on over 2 private acres with classic stone walls and professional landscaping, the home welcomes you with a dramatic two-story foyer and 9-foot ceilings throughout. The designer living room flows seamlessly into a

Kim Vartuli Keller Williams Realty

A rare Westport retreat blending serenity, sophistication & resort-style living. Privately set at the end of a quiet cul-de-sac off Bayberry Lane, this elegant four-bedroom, three-and-a-half-bath home offers over 4,600 sq ft of sun-filled living space surrounded by beautifully landscaped grounds. The property's two private acres feel like a personal park-complete with mature trees, curated

Michelle Sperry Coldwell Banker Realty

Prime location a few houses down from the Hunt Club three bedrooms with two additional bounus rooms and two bathrooms home with a fully finished walkout on a level one acre of land surrounded by multi million dollars homes.

Sayed Ibrahim Nationwide Homes

NEW CONSTRUCTION TO BE BUILT IN THE COVETED HUNT CLUB NEIGHBORHOOD - Renowned, luxury builder Mattera Construction is well-known for architecturally significant & stunning modern homes filled with elegance, timeless beauty, custom interiors with state-of-the-art amenities. Now offering a perfectly designed 6 bedroom home finished on 4 levels filled with elegant finishes, well sited on a quiet

Patricia Shea Coldwell Banker Realty

True Beauty In The Making! Construction of this 8,417SF dream residence with pool and spa on 1 private acre in coveted Greens Farms, Westport, is in full swing. 24 Edgemarth Hill was designed and will be crafted and appointed with the finest materials - see rendering photos of what's to come. Flaunting walls of windows, sexy floor-to-ceiling stone and textured accents, vaulted ceilings, and

Jaclyn Picarillo Higgins Group Bedford Square