Southport, CT Homes for Sale with Pool

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  /40

  $2,995,000

  • 6 Beds
  • 7 Baths
  • 9,664 Sq Ft

  91 Algonquin Rd, Fairfield, CT 06825

  Iconic Georgian Manor. A rare offering of architectural significance, this distinguished 1922 Georgian Colonial is set on 1.88 acres of level, park-like grounds in a desirable Fairfield enclave. Encompassing over 10,000 square feet, this 6-bedroom estate seamlessly blends historic grandeur with elevated, modern living. A stately presence is immediately felt through classic Georgian symmetry,

  

  Danielle Malloy

  Serhant Connecticut, LLC

  (475) 271-2961

  91 Algonquin Rd, Fairfield, CT 06825
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  /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

  

  Libby Tritschler

  William Raveis Real Estate

  (203) 350-0943

  260 Willow St, Southport, CT 06890
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  $4,450,000

  • 5 Beds
  • 7 Baths
  • 8,550 Sq Ft

  49 Hillspoint Rd, Westport, CT 06880

  Set discreetly at the end of a long drive and screened by mature landscaping, this exceptional Hillspoint residence offers a surprising sense of privacy in one of Westport's most convenient coastal settings. Just moments from Longshore Club Park, Compo Beach, town and train, it perfectly blends luxury, lifestyle and accessibility. Inside, soaring ceilings and sun-filled spaces create a light,

  Michelle Genovesi William Raveis Real Estate

  49 Hillspoint Rd, Westport, CT 06880
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  $2,700,000

  • 5 Beds
  • 4.5 Baths
  • 4,179 Sq Ft

  114 Cross Hwy, Westport, CT 06880

  Welcome to a one-of-a-kind home in the heart of Westport - where timeless Colonial charm meets the elegance of a Parisian Estate. Set on an acre+ this home offers sophistication, space, and serenity throughout. The light-filled LR stuns with vaulted ceilings, HW floors, a wood-burning fireplace, and French doors opening directly to the deck and pool - the perfect setting for everyday living or

  Robert Appell Coldwell Banker Realty

  114 Cross Hwy, Westport, CT 06880
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  $599,000

  • 3 Beds
  • 2 Baths
  • 1,386 Sq Ft

  3 Hills Ln, Westport, CT 06880

  A wonderful lifestyle awaits at Birchwood Condominiums, where low-maintenance living meets exceptional convenience. Ideally located on the Westport-Norwalk border, this sun-filled 3-bedroom, 2-bath residence offers a rare combination of privacy, natural beauty, and walkable access to everyday essentials, including Whole Foods just across the street. Set at the top of Hills Lane in a peaceful,

  Mary Ann Lindwall The Riverside Realty Group

  3 Hills Ln, Westport, CT 06880
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  /39

  $2,699,000

  • 5 Beds
  • 4.5 Baths
  • 4,628 Sq Ft

  1 Angora Rd, Westport, CT 06880

  One of Westport's premiere CUL-DE-SACS, WALKING DISTANCE TO ALL 3 SCHOOLS (Long Lots, Bedford, Staples), and 2.3 MILES TO GREENS FARMS TRAIN STATION, this beautifully renovated (2016/2017) 5-bedroom, 4.5-bath home perfectly blends modern luxury with timeless charm. Set on a full acre of manicured grounds, this property offers a serene retreat just minutes from every essential. The open floor plan

  Gina Hackett Compass Connecticut, LLC

  1 Angora Rd, Westport, CT 06880
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  $2,399,000

  • 5 Beds
  • 6 Baths
  • 5,739 Sq Ft

  2 Ledgemoor Ln, Westport, CT 06880

  Set on a quiet, private cul-de-sac very close to town and Winslow Park, this custom five-bedroom Colonial offers an exceptional opportunity for a new owner to leave their mark and add significant value. Designed with best-in-class materials and a thoughtfully planned layout, the home retains its gracious scale, natural flow, and exceptional character. Deferred maintenance has created the chance

  Alex Chingas Coldwell Banker Realty

  2 Ledgemoor Ln, Westport, CT 06880
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  /38

  $5,925,000

  • 6 Beds
  • 9 Baths
  • 6,561 Sq Ft

  3 Stony Point Rd, Westport, CT 06880

  Located within the highly desirable Stony Point association, this exceptional home offers a rare combination of privacy, water views, and convenience just moments from the train, local restaurants, and everyday amenities. This particular home enjoys private dock membership, providing summer boat access just steps from your door. Completely transformed and expanded in 2016, the home features over

  Debra Shaughnessy Coldwell Banker Realty

  3 Stony Point Rd, Westport, CT 06880
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  /40

  $15,000,000

  • 7 Beds
  • 6.5 Baths
  • 6,215 Sq Ft

  4 Sherwood Island Ln, Westport, CT 06880

  Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings ever offered. For more than 65 years, it has been held and enjoyed by the same family as a place to gather, unwind, and take in the ever-changing views across Sherwood Island Park and Long Island Sound. Surrounded by protected

  Andrew Whiteley Brown Harris Stevens

  4 Sherwood Island Ln, Westport, CT 06880
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  $8,995,000

  • 8 Beds
  • 10 Baths
  • 15,172 Sq Ft

  2 Judy Point Ln, Westport, CT 06880

  Set on over 3 private acres with sweeping water views, 2 Judy Point Lane is a remarkable Westport waterfront estate offering approximately 14,000 square feet of living space and a rare compound-style layout. The property consists of two substantial residences connected by a breezeway, creating exceptional flexibility for multi-generational living, extended guests, or a private guest house.

  Daniel Kramp Christie's International Real Estate

  2 Judy Point Ln, Westport, CT 06880
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  $22,825,000

  • 8 Beds
  • 10 Baths
  • 12,946 Sq Ft

  11 Beachside Common, Westport, CT 06880

  Direct Waterfront | Greens Farms An extraordinary new waterfront estate by award-winning Coastal Luxury Homes is coming to one of the most coveted stretches of the Connecticut shoreline. Set in the heart of Greens Farms, this spectacular 12,948 square foot modern residence will span four levels and capture sweeping, unobstructed views across Sherwood Island, Burying Hill Beach, and Long Island

  Andrew Whiteley Brown Harris Stevens

  11 Beachside Common, Westport, CT 06880
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  $3,990,000

  • 5 Beds
  • 7 Baths
  • 7,409 Sq Ft

  13 Rockyfield Rd, Westport, CT 06880

  This pristine Colonial offers timeless Westport elegance and effortless living, set on 1.12 flat, manicured acres framed by classic stone walls in a coveted, quiet neighborhood just one hour from NYC. The five-bedroom home features five full and two half baths, two dedicated offices, two versatile bonus spaces, custom millwork throughout, and abundant storage-perfect for today's work-from-home,

  Danna Rogers Higgins Group Bedford Square

  13 Rockyfield Rd, Westport, CT 06880
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  $4,899,000 Open Sun 2PM - 4PM

  • 6 Beds
  • 8 Baths
  • 8,190 Sq Ft

  19 Mortar Rock Rd, Westport, CT 06880

  Stunning modern transitional home built by Compo Luxury Homes in 2024 and ideally located just minutes to downtown Westport, Compo Beach, and the train. Set on .65 acres with city water, sewer, and natural gas, this beautifully designed residence offers over 8,000 square feet across four finished levels with 6 bedrooms, 6 full and 2 half baths. The open floor plan features a chef's kitchen with

  Danna Rogers Higgins Group Bedford Square

  19 Mortar Rock Rd, Westport, CT 06880
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  /40

  $1,800,000

  • 4 Beds
  • 3.5 Baths
  • 4,018 Sq Ft

  39 Marion Rd, Westport, CT 06880

  Nestled in the coveted Old Hill section of Westport, this exceptional residence offers a rare blend of space, serenity, & timeless appeal. With over 3,200 square feet, the home unfolds beautifully-beginning with a gracious entry foyer, leading into the living room with hardwood floors and anchored by a classic fireplace. The large eat-in kitchen offers double ovens, an abundance of cabinets and

  Stacy Pfannkuch Century 21 AllPoints Realty

  39 Marion Rd, Westport, CT 06880
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  $2,095,000

  • 4 Beds
  • 5 Baths
  • 3,921 Sq Ft

  2177 Cross Hwy, Fairfield, CT 06824

  A special property with pool & tennis court, on the Westport border, minutes to shops, restaurants and train. Experience refined luxury in this picturesque setting, situated back from the road down a long, lighted driveway, winding past a serene pond. Nearly 4000 sq ft with 4 bedrooms & 4.5 baths, this open floor plan home features city water, sewer, natural gas, oil heat and central A/C for

  Mary Ellen Gallagher Compass Connecticut, LLC

  2177 Cross Hwy, Fairfield, CT 06824
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  $3,000,000

  • 6 Beds
  • 5.5 Baths
  • 5,952 Sq Ft

  70 Meadow Ridge Rd, Fairfield, CT 06824

  Nestled on a picturesque cul-de-sac street in the heart of Southport, 70 Meadow Ridge Rd offers the perfect blend of classic charm and modern convenience. This custom home boasts 6 bedrooms and 5, Bathrooms providing ample space for comfortable living and entertaining. Step inside to discover sun-drenched living spaces featuring gleaming hardwood floors, a cozy fireplace, and an open-concept

  David Krasnoff Compass Connecticut, LLC

  70 Meadow Ridge Rd, Fairfield, CT 06824
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  $2,800,000

  • 4 Beds
  • 2.5 Baths
  • 4,243 Sq Ft

  118 Roseville Rd, Westport, CT 06880

  This Westport residence is a meticulously executed Passive House retrofit of a modernist concrete home originally built in 1938. Few properties achieve this level of energy efficiency while also prioritizing non-toxic, health-conscious building materials. As you pass through the home's front entry gate and hear the gentle rhythm of tires over gravel, a striking and handsome facade comes into

  Tyler Della Valle Dow Della Valle

  118 Roseville Rd, Westport, CT 06880
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  /40

  $4,300,000

  • 6 Beds
  • 9 Baths
  • 9,525 Sq Ft

  278 North Ave, Westport, CT 06880

  Set in a coveted estate enclave prized by CEOs and captains of industry, this exceptional, shingle-style residence embodies timeless architecture, extraordinary craftsmanship, and meticulous attention to detail. Built custom for a CEO, the home showcases uncompromising quality and gracious curb appeal that leave a lasting impression. Designed for seamless indoor-outdoor living and grand-scale

  Cyd Hamer William Pitt Sotheby's Int'l

  278 North Ave, Westport, CT 06880
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  /22

  $600,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  49 Southport Woods Dr, Southport, CT 06890

  Enjoy Southport Woods - community lifestyle with pool, clubhouse, paddle tennis and beautifully landscaped grounds in the heart of Southport. Convenient to Fairfield and Southport train stations, I-95, shopping, restaurants, schools and miles of beautiful shoreline, this location offers much. Privately located end unit features slate patio/yard area, two bedrooms (primary with full bath),

  Andrea Morelli Higgins Group Real Estate

  49 Southport Woods Dr, Southport, CT 06890
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  $4,400,000

  • 5 Beds
  • 8 Baths
  • 9,819 Sq Ft

  1 Flower Farm Ln, Westport, CT 06880

  Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room

  Heather Fitzgerald Coldwell Banker Realty

  1 Flower Farm Ln, Westport, CT 06880
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  $2,395,000

  • 4 Beds
  • 4.5 Baths
  • 3,620 Sq Ft

  783 Reef Rd, Fairfield, CT 06824

  Welcome to 783 Reef Road, a beautifully crafted home in the highly desirable Penfield Beach area of Fairfield. This elegant residence combines refined design with modern comfort, offering four bedrooms, four and a half bathrooms, and approximately 3,620 square feet of interior living space and an additional nearly 1,400 square feet of basement storage space. Inside, the foyer opens to a layout

  Daniel Durante Criterion Real Estate LLC

  783 Reef Rd, Fairfield, CT 06824
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  /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 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

  4800 Congress St, Fairfield, CT 06824
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  /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
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  $1,999,999 New Construction

  • 6 Beds
  • 4.5 Baths
  • 4,012 Sq Ft

  631 Reid St, Fairfield, CT 06824

  Welcome to this stunning new construction farmhouse colonial in Fairfield's coveted University area, offering modern luxury, timeless design, and a rare backyard oasis complete with a beautiful in-ground pool. Thoughtfully crafted with exceptional attention to detail, this 6-bedroom home delivers the perfect blend of style, comfort, and functionality. Step inside to bright, open concept living

  Jim Stobie Berkshire Hathaway NE Prop.

  631 Reid St, Fairfield, CT 06824
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  $5,599,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 7,387 Sq Ft

  36 Maple Ave S, Westport, CT 06880

  Beautiful Georgian Colonial style home in desired Greens Farms neighborhood design by renowned architect Judith Larson. A fabulous Redcoat design team make this home a must, perfect for todays's lifestyle with a classic feel. This 6 bedroom residence is set on a flat, level.70 acre property embodying a perfect synergy of architectural excellence and an enviable location. Crafted for modern living

  Kelly Loucas Compass Connecticut, LLC

  36 Maple Ave S, Westport, CT 06880
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  $4,750,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 6,611 Sq Ft

  21 Lockwood Cir, Westport, CT 06880

  Imagine a residence where every element has been considered for gracious living in stylish surroundings. This newly completed home by awardwinning Able Construction is set on a peaceful Coleytown estatearea street, framed by scenic land that enhances its sense of calm. A dramatic foyer with a woodaccented ceiling and millwork feature wall introduces interiors defined by creative decor, walls of

  Doug Bross Coldwell Banker Realty

  21 Lockwood Cir, Westport, CT 06880
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  $7,500,000 New Construction

  • 6 Beds
  • 9 Baths
  • 9,576 Sq Ft

  8 Loretta Ct, Westport, CT 06880

  Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning three and a half levels, this six-bedroom home features an airy layout with refined finishes

  Lianne Owen Coldwell Banker Realty

  8 Loretta Ct, Westport, CT 06880
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  /11

  $5,990,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 6,900 Sq Ft

  10 Mary Jane Ln, Westport, CT 06880

  New construction by renowned Red Coat Homes, ideally set on a quiet cul-de-sac in a premier Westport neighborhood. Designed by architect Judith Larson, this exceptional home offers over 7,000 sq ft of refined living space on more than one acre, complete with a resort-style pool. Timeless architecture and sophisticated finishes create spaces ideal for entertaining, work, and everyday living, with

  Danna Rogers Higgins Group Bedford Square

  10 Mary Jane Ln, Westport, CT 06880
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  /14

  $8,696,000 New Construction

  • 7 Beds
  • 8 Baths
  • 9,422 Sq Ft

  688 Hulls Farm Rd, Southport, CT 06890

  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

  688 Hulls Farm Rd, Southport, CT 06890
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  /19

  $3,900,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,100 Sq Ft

  1008 Fairfield Beach Rd, Fairfield, CT 06824

  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

  1008 Fairfield Beach Rd, Fairfield, CT 06824
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  $3,988,000 New Construction

  • 4 Beds
  • 8 Baths
  • 7,971 Sq Ft

  475 Fence Row Dr, Fairfield, CT 06824

  Set within The Ridge in Greenfield Hill, Fairfield's gated residential community, this residence originally designed by renowned architect Bill Blanski has been completely rebuilt and thoughtfully reimagined with the scale and finish of new construction. Spanning over 7,500 square feet, the home offers four bedrooms and six full and two half baths, with wide plank oak floors, multiple fireplaces,

  Erin Melson The Agency

  475 Fence Row Dr, Fairfield, CT 06824
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  $10,650,000 New Construction

  • 6 Beds
  • 8 Baths
  • 9,100 Sq Ft

  11 Dogwood Ln, Westport, CT 06880

  Another extraordinary masterpiece by Coastal Luxury Homes, ideally situated in one of Westport's premier neighborhoods. Spanning over 9000 square feet of living space this 6 bedroom estate is defined by bold architectural lines, chic designer interiors, expansive balconies and seamless indoor-outdoor living. A resort caliber pool, fully equipped outdoor kitchen, and lush manicured grounds

  Jen Kass Higgins Group Bedford Square

  11 Dogwood Ln, Westport, CT 06880
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  $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
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  $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
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  $4,299,000 New Construction

  • 5 Beds
  • 6 Baths
  • 4,879 Sq Ft

  5 Franklin Ave, Westport, CT 06880

  Nestled in one of Westport's most desirable walk-to-town neighborhoods, this exceptional new construction home combines timeless charm with modern luxury. Designed by acclaimed architect Judith Larson and crafted by trusted builder Redcoat Homes, this residence offers the perfect balance of style and functionality. Located on a level third-acre on a quiet cul-de-sac, the property is beautifully

  Kelly Loucas Compass Connecticut, LLC

  5 Franklin Ave, Westport, CT 06880
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  /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
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  /15

  $6,995,826 New Construction

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

  24 Edgemarth Hill Rd, Westport, CT 06880

  This Beauty will be ready Summer 2026! 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 sexy floor-to-ceiling walls of windows, stone and textured accents, vaulted

  Jaclyn Picarillo Higgins Group Bedford Square

  24 Edgemarth Hill Rd, Westport, CT 06880
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  /40

  $4,749,000 New Construction

  • 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
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  /2

  $6,999,999 New Construction

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

  32 Narrow Rocks Rd, Westport, CT 06880

  NEW CONSTRUCTION BY RENOWNED LUXURY BUILDER MATTERA CONSTRUCTION - STEPS TO COMPO BEACH! A rare opportunity to own a brand-new, architecturally refined home in one of Westport's most coveted coastal locations-just steps to Compo Beach, Longshore Club, downtown Westport, the train, and schools. Currently under construction, this impeccably designed 6-bedroom residence spans four finished levels

  Judy Michaelis Coldwell Banker Realty

  32 Narrow Rocks Rd, Westport, CT 06880
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  /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

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