38

Southport, CT Homes for Sale with Acreage

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  • /40

    $1,900,000

    • 5 Beds
    • 3.5 Baths
    • 3,228 Sq Ft

    9 Victoria Ln, Westport, CT 06880

    Premiere Long Lots Location | End-of-Cul-de-Sac | Pool! - Perfectly positioned at the end of a quiet cul-de-sac in Westport's highly sought-after Long Lots neighborhood, this bright and beautiful home offers exceptional privacy while remaining just minutes to the Parkway and Westport's Main Street shops and acclaimed restaurants. Set on a spectacular 1.05-acre property, this well-maintained

    Agent Photo

    Fredda Takacs

    Higgins Group Real Estate

    (203) 599-7484

    9 Victoria Ln, Westport, CT 06880
  • /40

    $4,795,000 Open Sun 1PM - 3PM

    • 6 Beds
    • 9 Baths
    • 9,700 Sq Ft

    21 Warnock Dr, Westport, CT 06880

    This striking architectural design meets refined luxury in a meticulously crafted 9,700+/- sq ft, 6-bedroom, 6 full, & 3 half bath new residence. Showcasing the collaborative excellence of AR Luxury Homes w/ interior design by Mary Beth Woods & architectural vision by Donald William Fairbanks, this exceptional property represents the pinnacle of modern sophistication w/ premium finishes,

    Agent Photo

    Brett Lieberman

    The Riverside Realty Group

    (203) 717-5836

    21 Warnock Dr, Westport, CT 06880
  • /9

    $3,750,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 5,000 Sq Ft

    22 Brett Rd, Fairfield, CT 06824

    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

    22 Brett Rd, Fairfield, CT 06824
  • /18

    $1,500,000

    • 4 Beds
    • 2 Baths
    • 1,925 Sq Ft

    20 Ermine St, Fairfield, CT 06824

    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

    20 Ermine St, Fairfield, CT 06824
  • /22

    $4,995,000 New Construction

    • 5 Beds
    • 7 Baths
    • 5,550 Sq Ft

    1 Coastal Ct, Westport, CT 06880

    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

    1 Coastal Ct, Westport, CT 06880
  • /2

    $5,485,686 New Construction

    • 7 Beds
    • 9 Baths
    • 7,243 Sq Ft

    25 Ellery Ln, Westport, CT 06880

    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

    25 Ellery Ln, Westport, CT 06880
  • /14

    $749,000

    • Land
    • 1.02 Acres
    • $734,314 per Acre

    844 Mill Hill Terrace, Fairfield, CT 06890

    This 1.02 acre parcel offers the rare combination of privacy and premier location. Tucked away in a quiet Southport neighborhood, yet just minutes to the harbor, beaches, train, restaurants, and charming village shops - it's the best of both worlds. The possibilities are endless - City water, City sewer and Natural Gas are available in the street. Whether you envision a timeless New England

    Barbara Sweeney Coldwell Banker Realty

    844 Mill Hill Terrace, Fairfield, CT 06890
  • /15

    $5,400,700 New Construction

    • 6 Beds
    • 7 Baths
    • 5,800 Sq Ft

    1 Sturges Hwy Unit Lot 1, Westport, CT 06880

    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

    1 Sturges Hwy Unit Lot 1, Westport, CT 06880
  • /28

    $4,399,000 New Construction

    • 6 Beds
    • 5.5 Baths
    • 7,510 Sq Ft

    13 Terhune Dr, Westport, CT 06880

    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

    13 Terhune Dr, Westport, CT 06880
  • /40

    $25,000,000

    • 6 Beds
    • 11 Baths
    • 19,569 Sq Ft

    1131 Sasco Hill Rd, Fairfield, CT 06824

    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

    1131 Sasco Hill Rd, Fairfield, CT 06824
  • /20

    $2,800,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 4,000 Sq Ft

    53 Cross Hwy, Westport, CT 06880

    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

    53 Cross Hwy, Westport, CT 06880
  • /40

    $3,750,000

    • 7 Beds
    • 9 Baths
    • 10,104 Sq Ft

    249 Greens Farms Rd, Westport, CT 06880

    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

    249 Greens Farms Rd, Westport, CT 06880
  • /3

    $2,199,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,700 Sq Ft

    180 Catamount Rd, Fairfield, CT 06824

    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

    180 Catamount Rd, Fairfield, CT 06824
  • /6

    $390,000

    • Land
    • 2 Acres
    • $195,000 per Acre

    6 Fox Run Ln, Westport, CT 06880

    This secluded property in Westport, CT at 6 Fox Run Lane offers an opportunity to submit your desired dream home plans to Westport on this picturesque 2 acres of rare undeveloped land. The lot is nestled in a prestigious upscale neighborhood and offers a tranquil bucolic setting, and is surrounded by nature. The new owner may design a custom home to suit your family's needs and preferences

    Derek Greene Derek Greene

    6 Fox Run Ln, Westport, CT 06880
  • /39

    $3,649,000

    • 5 Beds
    • 4.5 Baths
    • 5,515 Sq Ft

    2683 Bronson Rd, Fairfield, CT 06824

    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

    2683 Bronson Rd, Fairfield, CT 06824
  • /37

    $1,300,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft

    60 Clinton Ave, Westport, CT 06880

    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

    60 Clinton Ave, Westport, CT 06880
  • /23

    $6,682,000 New Construction

    • 6 Beds
    • 9 Baths
    • 7,801 Sq Ft

    86 Maple Ave S, Westport, CT 06880

    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

    86 Maple Ave S, Westport, CT 06880
  • /16

    $6,785,000 New Construction

    • 6 Beds
    • 9 Baths
    • 7,888 Sq Ft

    14 Burr School Rd, Westport, CT 06880

    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

    14 Burr School Rd, Westport, CT 06880
  • /40

    $2,850,000

    • 6 Beds
    • 8 Baths
    • 7,354 Sq Ft

    19A Darbrook Rd, Westport, CT 06880

    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

    19A Darbrook Rd, Westport, CT 06880
  • /40

    $15,000,000

    • 7 Beds
    • 10 Baths
    • 9,129 Sq Ft

    4800 Congress St, Fairfield, CT 06824

    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

    4800 Congress St, Fairfield, CT 06824
  • /26

    $3,999,000 New Construction

    • 6 Beds
    • 5.5 Baths
    • 6,010 Sq Ft

    13 Terhune Dr, Westport, CT 06880

    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

    13 Terhune Dr, Westport, CT 06880
  • /31

    $2,100,000

    • 4 Beds
    • 4.5 Baths
    • 6,600 Sq Ft

    342 Greens Farms Rd, Westport, CT 06880

    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

    342 Greens Farms Rd, Westport, CT 06880
  • /40

    $5,200,000

    • 6 Beds
    • 12 Baths
    • 13,979 Sq Ft

    2959 Congress St, Fairfield, CT 06824

    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

    2959 Congress St, Fairfield, CT 06824
  • /40

    $12,000,000

    • 7 Beds
    • 6.5 Baths
    • 8,119 Sq Ft

    260 Willow St, Southport, CT 06890

    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

    260 Willow St, Southport, CT 06890
  • /28

    $19,800,000

    • 8 Beds
    • 8.5 Baths
    • 9,995 Sq Ft

    92 Beachside Ave, Westport, CT 06880

    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

    92 Beachside Ave, Westport, CT 06880
  • /18

    $9,995,000 New Construction

    • 7 Beds
    • 10 Baths
    • 10,800 Sq Ft

    688 Hulls Farm Rd, Southport, CT 06890

    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

    688 Hulls Farm Rd, Southport, CT 06890
  • /15

    $5,472,860 New Construction

    • 7 Beds
    • 8 Baths
    • 6,120 Sq Ft

    1 Sturges Hwy Unit 2, Westport, CT 06880

    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

    1 Sturges Hwy Unit 2, Westport, CT 06880
  • /40

    $4,899,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 8 Baths
    • 7,400 Sq Ft

    10 Tierney Ln, Westport, CT 06880

    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

    10 Tierney Ln, Westport, CT 06880
  • /40

    $2,750,000 Open Sat 11:30AM - 1PM

    • 4 Beds
    • 5 Baths
    • 5,207 Sq Ft

    123 Greens Farms Rd, Westport, CT 06880

    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

    123 Greens Farms Rd, Westport, CT 06880
  • /36

    $1,695,000

    • 6 Beds
    • 4.5 Baths
    • 5,325 Sq Ft

    212 Fence Row Dr, Fairfield, CT 06824

    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

    212 Fence Row Dr, Fairfield, CT 06824
  • /39

    $3,500,000

    • 5 Beds
    • 6.5 Baths
    • 5,789 Sq Ft

    221 Greens Farms Rd, Westport, CT 06880

    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

    221 Greens Farms Rd, Westport, CT 06880
  • /40

    $2,498,000

    • 5 Beds
    • 8 Baths
    • 8,136 Sq Ft

    88 Merry Meet Cir, Fairfield, CT 06824

    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

    88 Merry Meet Cir, Fairfield, CT 06824
  • /40

    $2,499,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 5,015 Sq Ft

    200 Long Meadow Rd, Fairfield, CT 06824

    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

    200 Long Meadow Rd, Fairfield, CT 06824
  • /40

    $2,785,000

    • 4 Beds
    • 3.5 Baths
    • 5,434 Sq Ft

    6 Nutcracker Ln, Westport, CT 06880

    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

    6 Nutcracker Ln, Westport, CT 06880
  • /11

    $1,699,900

    • 3 Beds
    • 2 Baths
    • 3,171 Sq Ft

    40 Maple Ave N, Westport, CT 06880

    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

    40 Maple Ave N, Westport, CT 06880
  • /4

    $1,300,000

    • Land
    • 2.65 Acres
    • $490,566 per Acre

    22 Brett Rd, Fairfield, CT 06824

    An exceptional opportunity to build your dream home on one of the most desirable and scenic settings in Fairfield. This beautiful, flat 2.65-acre parcel-approved by the Wetlands Commission for a 5-bedroom, 5-bathroom residence with a pool and pool house-offers both privacy and prestige. The property is situated in the estate section of Greenfield Hill. With its driveway access on Brett Road, a

    Andrew Whiteley Brown Harris Stevens

    22 Brett Rd, Fairfield, CT 06824
  • /2

    $5,980,000 New Construction

    • 6 Beds
    • 9 Baths
    • 10,521 Sq Ft

    21 Sturges Commons, Westport, CT 06880

    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

    21 Sturges Commons, Westport, CT 06880
  • /17

    $6,995,826 New Construction

    • 6 Beds
    • 10 Baths
    • 8,417 Sq Ft

    24 Edgemarth Hill Rd, Westport, CT 06880

    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

    24 Edgemarth Hill Rd, Westport, CT 06880
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