Southport, CT Homes for Sale with Pool

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  /36

  $5,349,000

  • 5 Beds
  • 8 Baths
  • 6,503 Sq Ft

  31 Stonybrook Rd, Westport, CT 06880

  From the moment you enter the gates of this Old Hill estate, you know you've arrived- a rare sanctuary built with a level of custom stonework and craftsmanship impossible to replicate today. This stunning 5 bedroom, 6.2 bath home offers an extraordinary blend of elegance, privacy, and nature. Set in a mature landscape that takes generations to establish, the setting delivers unmatched wildlife

  Kristi Law William Pitt Sotheby's Int'l

  31 Stonybrook Rd, Westport, CT 06880
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  /40

  $1,925,000

  • 4 Beds
  • 3.5 Baths
  • 4,779 Sq Ft

  550 Wellington Dr, Fairfield, CT 06824

  Tucked at the end of a quiet Greenfield Hill cul-de-sac, 550 Wellington Drive feels like a true retreat-private, peaceful and designed for the way you actually want to live. Set on 2.47 secluded acres, this 4-bed, 4,776sqft home offers an exceptional amount of space to gather, entertain and spread out, with a floor plan that gives everyone a place of their own. The 1st floor is especially

  Wendy Ryan Brown Harris Stevens

  550 Wellington Dr, Fairfield, CT 06824
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  /30

  $765,000

  Open Sun 1PM - 3PM Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,281 Sq Ft

  181 Miro St, Fairfield, CT 06825

  Fully updated and move-in ready, this home sits on a quiet, low-traffic street just minutes from both I-95 and the Merritt Parkway, an ideal setup for commuters who still want a peaceful neighborhood setting. You're right down the street from local schools and just minutes from area shopping. Freshly painted throughout, the home features refinished hardwood floors across the main level, a bright

  Lindsey Rosen William Pitt Sotheby's Int'l

  181 Miro St, Fairfield, CT 06825
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  /20

  $6,495,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,062 Sq Ft

  5 Baldwin Place, Westport, CT 06880

  Rarely does a new construction home and property like this come on the market in Westport. Set at the end of a cul-de-sac, in the coveted Long Lots neighborhood, this 2.3-acre, flat property offers a rare combination of privacy and convenience to town. The property features a resort-style, saltwater pool w/spa and automatic safety cover, expansive covered and open-air patios, and a fully equipped

  Lori Popkin Coldwell Banker Realty

  5 Baldwin Place, Westport, CT 06880
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  /40

  $2,670,000

  $120K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,072 Sq Ft

  56 Charcoal Hill Rd, Westport, CT 06880

  A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail,

  Doug Bross Coldwell Banker Realty

  56 Charcoal Hill Rd, Westport, CT 06880
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  /37

  $4,250,000

  • 5 Beds
  • 7 Baths
  • 7,652 Sq Ft

  16 Rockyfield Rd, Westport, CT 06880

  Ready to enjoy from day 1, all of the work has been done to upgrade and update 16 Rockyfield Road.The residence has been completely retooled (ask for the upgrade list!). This is the ideal home that does not feel generic and the luxury touches will make everyday seem special. The brand new kitchen is a showstopper featuring handcrafted Zellige tiles,a Lacanche range,2 dishwashers and custom

  Meredith Cohen Serhant Connecticut, LLC

  16 Rockyfield Rd, Westport, CT 06880
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  /40

  $1,995,000

  $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,315 Sq Ft

  2 Drumlin Rd, Westport, CT 06880

  Experience modern coastal luxury in this custom-built, down-to-the-studs NEW CONSTRUCTION just minutes from Compo Beach and downtown Westport. Blending the scale and sophistication of a true custom home with effortless single-level living, this exceptional property showcases designer finishes and impeccable craftsmanship throughout. The sun-filled open floor plan features soaring cathedral

  Julie Vanderblue Higgins Group Real Estate

  2 Drumlin Rd, Westport, CT 06880
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  /35

  $7,985,000

  • 6 Beds
  • 6 Baths
  • 9,121 Sq Ft

  12 Beltas Farm Ln, Westport, CT 06880

  12 Beltas Farm Lane is an extraordinary new construction estate in Westport, Connecticut, set within Beltas Farm, one of Westport, Connecticut's newest and most distinctive enclaves, Westport, CT 06880. Once part of a 23-acre working family farm, this special setting has been thoughtfully transformed into an intimate collection of exceptional residences, with nearly five acres preserved as open

  Judy Michaelis Coldwell Banker Realty

  12 Beltas Farm Ln, Westport, CT 06880
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  /3

  $6,999,999

  • 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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  /38

  $4,395,000

  Open Thu 11AM - 2PM Coming Soon

  • 4 Beds
  • 6.5 Baths
  • 4,882 Sq Ft

  297 Lalley Blvd, Fairfield, CT 06824

  A rare opportunity in Fairfield's Beach area: two separate residences offered together, creating a property with extraordinary flexibility just moments from the beach, town, train, and schools. At the heart of the offering is 297 Lalley, a beautifully designed newer home with a pool, expansive outdoor living, and a light-filled interior created for gathering. The kitchen is anchored by an

  Cindy Raney Coldwell Banker Realty

  297 Lalley Blvd, Fairfield, CT 06824
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  /40

  $1,175,000

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  1951 Burr St, Fairfield, CT 06824

  *OFFERS DUE 5PM 9/21* Welcome to this quintessential New England colonial, lovingly cherished by the same owner for over 4 decades. On 2 flat, picturesque acres, this timeless home offers serene, private living while remaining centrally located. A sweeping circular driveway creates a warm arrival, while the sprawling, level backyard provides an ideal setting for outdoor entertaining, with room

  Lindsey Rosen William Pitt Sotheby's Int'l

  1951 Burr St, Fairfield, CT 06824
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  /40

  $3,299,000

  $200K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,778 Sq Ft

  240 North Ave, Westport, CT 06880

  "MEADOW WOOD" - Nearly two acres of Westport's most spectacular land is the setting for this storied estate, which has been completely remodeled, expanded and transformed for modern living. Totally fenced & screened w/privacy trees, this unique property offers rare sophistication with a stunning main residence, gunite pool, and a 2,447+/- sqft barn. Gated driveways lead to both the main house &

  Doug Bross Coldwell Banker Realty

  240 North Ave, Westport, CT 06880
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  /11

  $6,250,000

  New Construction

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

  21 Sturges Commons, Westport, CT 06880

  NEW CONSTRUCTION NEAR COMPLETION IN THE COVETED HUNT CLUB NEIGHBORHOOD BY THE MOST SOUGHT-AFTER LUXURY BUILDER, MATTERA CONSTRUCTION, celebrated for creating architecturally significant & stunning modern homes that blend timeless elegance, exceptional craftsmanship & bespoke interiors. A Mattera home is a masterpiece with state-of-the-art amenities, breathtaking design & uncompromising structural

  Patricia Shea Coldwell Banker Realty

  21 Sturges Commons, Westport, CT 06880
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  /40

  $5,750,000

  • 4 Beds
  • 4.5 Baths
  • 3,800 Sq Ft

  69 Birch Rd, Fairfield, CT 06824

  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

  69 Birch Rd, Fairfield, CT 06824
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  /10

  $2,650,000

  • Land
  • 1.23 Acres
  • $2,154,472 per Acre

  4 Lantern Hill Rd, Westport, CT 06880

  Rare opportunity to build a custom residence on 1.2 acres in Westport. The previous home has been demolished, and the property is offered with approved architectural plans. Bring your preferred builder and collaborate with the project architect to tailor the design to your vision. Also listed as a to-be-built single-family residence.

  Garvey Fox Serhant Connecticut LLC

  4 Lantern Hill Rd, Westport, CT 06880
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  /39

  $4,600,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 8,185 Sq Ft

  2 Windy Hill Rd, Westport, CT 06880

  Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural

  Jacob Bivona Keller Williams Prestige Prop.

  2 Windy Hill Rd, Westport, CT 06880
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  /40

  $4,850,000

  • 5 Beds
  • 5 Baths
  • 5,103 Sq Ft

  22 Evergreen Ave, Westport, CT 06880

  Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate

  Valerie Alvarez Serhant Connecticut, LLC

  22 Evergreen Ave, Westport, CT 06880
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  /15

  $7,015,000

  New Construction

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

  24 Edgemarth Hill Rd, Westport, CT 06880

  Move right in THIS October! Just weeks away from completion, come see this 8,417SF dream residence w/sauna, pool & spa on 1 private acre in coveted Greens Farms as the finishing touches are being made. 24 Edgemarth Hill was designed, crafted, and appointed with the finest materials - see rendering photos. 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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  /36

  $3,999,500

  $2M PRICE DROP

  • 3 Beds
  • 4.5 Baths
  • 2,528 Sq Ft

  1681 Fairfield Beach Rd, Fairfield, CT 06824

  Rarely does a property offer frontage on both Long Island Sound and Pine Creek. Positioned along a naturally elevated stretch of Fairfield Beach framed by protective dunes, the property enjoys a broad sandy beach at both high and low tide. Located within a residential section of Fairfield Beach away from many public beach access points, the setting offers a unique combination of beach, creek, and

  Stephanie Barnes William Raveis Real Estate

  1681 Fairfield Beach Rd, Fairfield, CT 06824
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  /14

  $8,696,000

  New Construction

  • 7 Beds
  • 8 Baths
  • 8,559 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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  /33

  $6,499,000

  • 4 Beds
  • 4.5 Baths
  • 3,511 Sq Ft

  1845 & 1859 Fairfield Beach Rd, Fairfield, CT 06824

  A rare and extraordinary Long Island Sound waterfront estate, offering over half an acre and nearly 100 feet of direct beach frontage across two parcels. Set along one of Fairfield's most coveted stretches of shoreline, this exceptional property presents a unique opportunity to create a private coastal compound with an abundance of space, water access, and privacy. The expansive 0.55-acre

  Mary Kate Klemish-Boehm Brown Harris Stevens

  1845 & 1859 Fairfield Beach Rd, Fairfield, CT 06824
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  /17

  $9,860,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 9,200 Sq Ft

  9 Over Rock Ln, Westport, CT 06880

  Newly completed, this exceptional modern estate offers approximately 9,200 square feet on 2.1 private acres just minutes from downtown Westport, Compo Beach, and Metro-North. Thoughtfully designed with European craftsmanship, premium finishes, and sophisticated smart-home technology, the home blends timeless design with exceptional functionality. A dramatic floating staircase anchors four

  Danna Rogers Higgins Group Bedford Square

  9 Over Rock Ln, Westport, CT 06880
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  /29

  $399,900

  • 1 Bed
  • 1 Bath
  • 611 Sq Ft

  350 Grovers Ave Unit 1H, Bridgeport, CT 06605

  The Anchorage - Resort style living in this wonderful complex with a beautifully landscaped courtyard offering an in-ground pool overlooking Black Rock Harbor and Long Island Sound. The owners meticulously maintained the unit leaving nothing to do but bring in the furniture. This move in condition first floor, one bedroom unit offers a spacious open living/dining room with spectacular views of

  John Kleps Berkshire Hathaway NE Prop.

  350 Grovers Ave Unit 1H, Bridgeport, CT 06605
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  /39

  $1,995,000

  $205K PRICE DROP

  • 5 Beds
  • 6 Baths
  • 6,136 Sq Ft

  203 Wildflower Ln, Fairfield, CT 06824

  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

  203 Wildflower Ln, Fairfield, CT 06824
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  /39

  $1,875,000

  $24K PRICE DROP

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

  2177 Cross Hwy, Fairfield, CT 06824

  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

  2177 Cross Hwy, Fairfield, CT 06824
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  /40

  $5,650,000

  New Construction

  • 7 Beds
  • 9 Baths
  • 8,762 Sq Ft

  8 Pleasant Valley Ln, Westport, CT 06880

  Experience modern luxury in this new SIR SIGNATURE Home by SIR Development, Westport's premier builder. Set on 1.02 private acres on a coveted cul de sac, this home offers a striking approach, 3car garage, and rare backyard privacy, all within walking distance to Bedford Middle, Staples High, Wakeman Fields, and Town Farm. A fresh contemporary aesthetic features a dramatic two story foyer, 10ft

  Doug Bross Coldwell Banker Realty

  8 Pleasant Valley Ln, Westport, CT 06880
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  /39

  $1,699,000

  • 2 Beds
  • 1.5 Baths
  • 2,131 Sq Ft

  160 Cedar Rd, Southport, CT 06890

  Welcome to 160 Cedar Road, a truly special farmhouse in Southport that has been thoughtfully renovated and reimagined. Filled with warmth, character, and modern updates, this unique property beautifully blends timeless charm with contemporary comfort. Privately set and abutting Aspetuck Land Trust property, the 2-bedroom, possible 3-bedroom, 1.5-bath home enjoys a beautiful natural setting on

  Gabrielle DiBianco Higgins Group Bedford Square

  160 Cedar Rd, Southport, CT 06890
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  /7

  $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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  /39

  $865,000

  $50K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  2196 N Benson Rd, Fairfield, CT 06824

  Welcome to 2196 North Benson Road! This unique property is situated on a private drive in the sought after University Area. The spacious, fenced back yard with inground pool serves as an oasis for pets and guests alike. The property boasts a generous first floor MBR and half bath. There are also two gabled bedrooms and a full bath on the second floor. The kitchen extends the entire rear of the

  John Swaim Realty ONE Group Connect

  2196 N Benson Rd, Fairfield, CT 06824

Showing Results 41 - 69, Page 2 of 2