Colonial Homes for Sale in Southport, CT

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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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  /36

  $4,950,000

  $1M 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 South 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,

  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
  • 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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  $4,700,000

  • 6 Beds
  • 6.5 Baths
  • 7,575 Sq Ft

  21 Daniel Ct, Westport, CT 06880

  Nestled at the end of an exceptionally wide, tree-lined cul-de-sac on one of Westport's most picturesque streets, this timeless brick estate offers both elegance and privacy while remaining moments from town, beaches, and commuting conveniences. Set with a paver circular driveway and surrounded by mature landscaping, the property exudes warmth, scale, and classic sophistication at every turn.

  Meredith Cohen Serhant Connecticut, LLC

  21 Daniel Ct, Westport, CT 06880
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  /40

  $2,495,000

  • 3 Beds
  • 2.5 Baths
  • 2,755 Sq Ft

  28 Center St, Southport, CT 06890

  Gracious Southport Village/Southport Harbor 3Bedroom, 2 1/2Bath Colonial Home, with Water & Harbor views. Enjoy the convenience of walking to all that Southport Village has to offer; Shops, Markets, Restaurants, Pharmacy, Post Office, and Southport Train Station. View and stroll the beautiful streets and homes all overlooking the picturesque Southport Harbor, Long Island Sound & Southport Beaches!

  Terry Keegan Fairfield County Real Estate

  28 Center St, Southport, CT 06890
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  /40

  $1,925,000

  New Construction Open Sat 12PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 2,962 Sq Ft

  200 Henry St, Fairfield, CT 06824

  Welcome to 200 Henry Street! This newly constructed home has everything you need in the sought-after Sturges Neighborhood. It's a short walk to Perry"s Mill Pond & Mill Hollow Park. The Gray Pella Windows set against the classic White Hardie Plank Siding is simply beautiful, a true design statement. This upscale home has refined finishes including Character Oak Wood floors throughout the Main &

  Jane Broder Camelot Real Estate

  200 Henry St, Fairfield, CT 06824
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  /40

  $2,500,000

  $200K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 5,793 Sq Ft

  28 Bulkley Ave N, Westport, CT 06880

  Beautifully renovated 1799 antique Colonial offering timeless charm, modern luxury, flat pool-worthy property, and exceptional convenience, just one light to the Greens Farms train. This special home captures the soul of historic Westport while delivering the comfort of today's lifestyle. Thoughtfully renovated, it blends original character, architectural detail, warmth, and six fireplaces with

  Judy Michaelis Coldwell Banker Realty

  28 Bulkley Ave N, Westport, CT 06880
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  /39

  $2,995,000

  $355K PRICE DROP

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

  221 Greens Farms Rd, Westport, CT 06880

  The Bedford House: Architecturally and historically significant estate in Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's true gems with a remarkable provenance. Set on 2.33 acres with a gunite pool & spa, court and a 2400 SF barn w/ 3 car garage, loft and more, this estate blends timeless elegance with modern comfort. Originally built in 1904 and

  Patricia Shea Coldwell Banker Realty

  221 Greens Farms 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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  /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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  /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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  /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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  /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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  $1,700,000

  • 5 Beds
  • 4.5 Baths
  • 4,676 Sq Ft

  282 Glen Ridge Rd, Fairfield, CT 06825

  Beautiful Center Hall Colonial in Fairfield's sought after Lake Mohegan neighborhood. This lovingly maintained 5 bedroom, 4 full & 1 half bath home offers the perfect combination of space, functionality & location. A dramatic vaulted entry welcomes you inside where hardwood floors flow throughout the home. The spacious layout includes a home office, formal dining room, expansive family room with

  Amie Belile William Raveis Real Estate

  282 Glen Ridge Rd, Fairfield, CT 06825
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  /38

  $1,598,000

  • 5 Beds
  • 3.5 Baths
  • 3,264 Sq Ft

  91 Lockwood Rd, Fairfield, CT 06825

  Welcome to 91 Lockwood Road, where modern farmhouse charm meets elevated design. Nestled in one of the area's most desirable neighborhoods, this beautifully reimagined home offers the perfect blend of style, comfort, and functionality. Designed for today's lifestyle, this home offers 5-6 bedrooms, 3 full baths, and 1 half bath, along with an open-concept floor plan that seamlessly connects the

  Susan Bento Distinct Realty

  91 Lockwood Rd, Fairfield, CT 06825
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  /21

  $1,875,000

  New Construction Coming Soon

  • 5 Beds
  • 5.5 Baths
  • 4,180 Sq Ft

  1964 N Benson Rd, Fairfield, CT 06824

  Nestled on a sprawling one-acre lot, this stunning new home offers 4180 sq ft of above-grade living space. Situated in the highly desirable University area of Fairfield, it features 5 bedrooms/5.5 bathrooms. The heart of the home is a culinary masterpiece with GE Monogram appliances, classic shaker-style cabinetry, quartz countertops and a large kitchen island. The kitchen flows into a sunlit

  Jeff Poarch Poarch Realty

  1964 N Benson Rd, Fairfield, CT 06824
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  /2

  $4,700,000

  • 6 Beds
  • 6 Baths
  • 6,000 Sq Ft

  394 Penfield Rd, Fairfield, CT 06824

  IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7

  Helene Salerno Ogents, LLC

  394 Penfield Rd, Fairfield, CT 06824
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  /2

  $5,199,000

  New Construction Open Sat 12PM - 4PM

  • 6 Beds
  • 8 Baths
  • 8,935 Sq Ft

  4 Sycamore Dr, Westport, CT 06880

  Tucked away on a quiet cul de sac in the desirable Hunt Club area of Long Lots in Westport is this new construction home built by CCO Habitats. Three levels of finished living space with ten foot ceilings on the first floor give an amazing sense of openness, as well as better functionality than four level homes. Think about it. Who really wants to walk up to the third floor every day? That's

  Maryann Levanti Higgins Group Bedford Square

  4 Sycamore Dr, Westport, CT 06880

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