Southport, CT Homes

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  $3,425,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 3,000 Sq Ft

  2101 Fairfield Beach Rd, Fairfield, CT 06824

  Gorgeous waterfront retreat w/ breathtaking panoramic LI Sound views & miles of walkable sandy beach. This exceptional FEMA compliant coastal retreat includes a private boat dock w/ an additional two-car garage on the creek side, creating endless opportunities for waterfront enjoyment. Featuring 3 levels of spacious living, w/ 8 rooms & 4 full baths, thoughtfully designed for everyday living &

  

  Jackie Davis

  William Raveis Real Estate

  (475) 271-4633

  2101 Fairfield Beach Rd, Fairfield, CT 06824
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  /6

  $1,850 total monthly price

  • 2 Beds
  • 1 Bath
  • 22,736 Sq Ft
  • Apartment for Rent

  785 Hancock Ave Unit 8, Bridgeport, CT 06605

  Check out this clean and bright 2-bedroom apartment heat and hot water included! available now! Perfect for your new home.

  

  Lisa Nussbaum

  Top Tier Realty Group, LLC

  (203) 204-8808

  785 Hancock Ave Unit 8, Bridgeport, CT 06605
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  $1,995,000 Sold Jun 10, 2025

  11 Thomas Rd, Westport, CT 06880

  • 4 Beds
  • 3.5 Baths
  • 2,551 Sq Ft
  • Built 1976

  Last Sold Summary

  • $782/SF
  • 7 Days On Market

  Current Estimated Value $2,045,985

  Last Listing Agent Mark Gilrain Brown Harris Stevens

  11 Thomas Rd, Westport, CT 06880
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  Est $626,204 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,668 Sq Ft

  1986 Kings Hwy, Fairfield, CT 06824

  1986 Kings Hwy, Fairfield, CT 06824
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  $1,049,000 Open Sat 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,556 Sq Ft

  121 Alden St, Fairfield, CT 06824

  Picture perfect Cape Cod home in the heart of the beach area, move in ready and beautifully updated. Welcome home to 121 Alden Street. This stylish residence shows like a dream offering 7 rooms, including 3 bedrooms (two upstairs and a hard to find main level bedroom) and 2 full baths. The homeowner has made significant home improvements, including a freshly painted interior, new deck, new patio,

  

  Jackie Davis

  William Raveis Real Estate

  (203) 487-5605

  121 Alden St, Fairfield, CT 06824
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  /2

  $1,900 total monthly price

  • 2 Beds
  • 1 Bath
  • 3,360 Sq Ft
  • House for Rent

  303 Poplar St, Bridgeport, CT 06605

  A charming two-bedroom apartment is available for immediate occupancy. This move-in ready residence offers a comfortable and inviting living space, The apartment features modern amenities and a well-maintained interior. Don't miss the opportunity to make this delightful apartment your new home.

  

  Lisa Nussbaum

  Top Tier Realty Group, LLC

  (475) 242-5814

  303 Poplar St, Bridgeport, CT 06605
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  $1,662,000 Sold Jun 30, 2025

  16 Mortar Rock Rd, Westport, CT 06880

  • 4 Beds
  • 2.5 Baths
  • 2,478 Sq Ft
  • Built 1966

  Last Sold Summary

  • 7% Above List Price
  • $671/SF
  • 6 Days On Market

  Current Estimated Value $1,682,889

  Last Listing Agent Linda Dunsmore Coldwell Banker Realty

  16 Mortar Rock Rd, Westport, CT 06880
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  Est $1,713,201 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,913 Sq Ft

  3 Mystic Ln, Westport, CT 06880

  3 Mystic Ln, Westport, CT 06880
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  /15

  $310,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  2612 North Ave Unit E2, Bridgeport, CT 06604

  Welcome to your move-in ready home! This charming 2-bedroom, 1.5-bath residence offers comfort, style, and thoughtful updates throughout. Enjoy brand-new carpet across the entire home, new flooring in the kitchen and first-floor bath, plus a brand-new dishwasher. The first-floor bathroom features a new vanity, shelving, and stylish wallpaper for a fresh, modern look. Upstairs, you'll find newly

  

  Paul Martillo

  Century 21 AllPoints Realty

  (203) 405-9205

  2612 North Ave Unit E2, Bridgeport, CT 06604
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  /2

  $1,700 total monthly price

  • 1 Bed
  • 1 Bath
  • 22,984 Sq Ft
  • Apartment for Rent

  2260 Fairfield Ave, Bridgeport, CT 06605

  This exceptional one bedroom apartment features included heating and hot water, has been recently remodeled, and is ready for immediate occupancy.

  

  Lisa Nussbaum

  Top Tier Realty Group, LLC

  (475) 255-3165

  2260 Fairfield Ave, Bridgeport, CT 06605
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  $1,075,000 Sold Oct 30, 2025

  9 Clinton Ave, Westport, CT 06880

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 1910

  Last Sold Summary

  • 2% Above List Price
  • $741/SF
  • 17 Days On Market

  Last Listing Agent Linda Dunsmore Coldwell Banker Realty

  9 Clinton Ave, Westport, CT 06880
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  Est $905,899 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,737 Sq Ft

  499 Main St, Westport, CT 06880

  499 Main St, Westport, CT 06880
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  /40

  $1,900,000

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

  9 Victoria Ln, Westport, CT 06880

  Highest and Best offers to be submitted by Wednesday, 1/14 at 5pm. 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

  

  Fredda Takacs

  Higgins Group Real Estate

  (203) 599-7484

  9 Victoria Ln, Westport, CT 06880
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  /25

  $4,500 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  28 Mill Hill Rd Unit 28, Fairfield, CT 06890

  Welcome home to 28 Mill Hill Road #28! This first-floor ranch style condo in Southport Woods presents a great opportunity to enjoy living in a sought-after community. Designed for effortless one level living, this move-in ready home offers both a gracious front entrance and a private exterior entry, providing comfort, privacy, and ease. The interior has been updated with fresh paint and newer

  

  Jackie Davis

  William Raveis Real Estate

  (475) 222-1217

  28 Mill Hill Rd Unit 28, Fairfield, CT 06890
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  $3,500,000 Sold Sep 22, 2025

  6 Florian Ct, Westport, CT 06880

  • 5 Beds
  • 6.5 Baths
  • 7,970 Sq Ft
  • Built 2007

  Last Sold Summary

  • 10% Below List Price
  • $439/SF
  • 88 Days On Market

  Current Estimated Value $3,432,729

  Last Listing Agent Lori Popkin Coldwell Banker Realty

  6 Florian Ct, Westport, CT 06880
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  Est $3,818,047 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,058 Sq Ft

  97 S Gate Ln, Southport, CT 06890

  97 S Gate Ln, Southport, CT 06890
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  /40

  $699,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,902 Sq Ft

  30 Osborne Place, Southport, CT 06890

  Welcome to 30 Osborne Place, ideally situated in one of Southport's premier neighborhoods. This beautifully maintained Townhome offers three levels of spacious, light-filled living designed for both comfort and flexibility. The main level features an open-concept floor plan with a dedicated office and an eat-in kitchen that flows seamlessly into the dining area. Sliding doors lead to a private

  

  Lisa Mancini

  William Raveis Real Estate

  (203) 312-7996

  30 Osborne Place, Southport, CT 06890
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  /15

  $6,250 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  437 Hulls Farm ~Carriage House~ Rd, Fairfield, CT 06890

  Tucked away on a picturesque six-acre estate between Fairfield and Westport, this restored vintage Carriage House offers a rare blend of privacy, charm, and modern convenience just minutes from Southport Harbor, area beaches, and vibrant dining, shopping, and entertainment. This energy-efficient 2,000-square-foot residence is available beautifully furnished or unfurnished, making it an ideal

  

  Amy Waugh Curry ABR CRS GRI

  Berkshire Hathaway NE Prop.

  (203) 439-5035

  437 Hulls Farm ~Carriage House~ Rd, Fairfield, CT 06890
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  $715,000 Sold Apr 10, 2025

  64 Papermill Ln, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 2,163 Sq Ft
  • Built 1958

  Last Sold Summary

  • 1% Below List Price
  • $331/SF
  • 92 Days On Market

  Current Estimated Value $767,228

  Last Listing Agent Jill Taylor RE/MAX Right Choice

  64 Papermill Ln, Fairfield, CT 06824
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  Est $1,779,996 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 976 Sq Ft

  380 Pine Creek Ave, Fairfield, CT 06824

  380 Pine Creek Ave, Fairfield, CT 06824
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  /27

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  145 Brentwood Ave, Fairfield, CT 06825

  Welcome to 145 Brentwood. This beautiful Fairfield townhome offers over 1,800 square feet of modern living across three levels. As you walk up to the main level, you're greeted with tons of natural light, 9 foot ceilings, and beautiful hardwood floors. The sleek kitchen features granite countertops and stainless steel appliances. Your private deck opens right off of your dining area- perfect for

  

  Thomas Bepko

  YellowBrick Real Estate LLC

  (475) 242-4693

  145 Brentwood Ave, Fairfield, CT 06825
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  /28

  $6,000 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,048 Sq Ft
  • House for Rent

  132 Pequot Ave, Southport, CT 06890

  132 Pequot Avenue offers a rare opportunity to rent in the heart of Southport Village. Perfectly positioned just moments from the harbor, shops, dining, and the train station, this beautifully updated two-bedroom home delivers effortless walkability in one of Fairfield County's most sought after neighborhoods. The residence has been thoughtfully renovated with quality finishes throughout.

  

  Jackie Davis

  William Raveis Real Estate

  (203) 693-8342

  132 Pequot Ave, Southport, CT 06890
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  $5,575,000 Sold Aug 26, 2025

  29 Sturges Commons, Westport, CT 06880

  • 6 Beds
  • 9 Baths
  • 8,817 Sq Ft
  • Built 2012

  Last Sold Summary

  • 6% Below List Price
  • $632/SF
  • 110 Days On Market

  Current Estimated Value $5,601,735

  Last Listing Agent Doug Bross Coldwell Banker Realty

  29 Sturges Commons, Westport, CT 06880
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  Est $742,572 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  130 Partridge Ln, Fairfield, CT 06824

  130 Partridge Ln, Fairfield, CT 06824
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  /34

  $2,527,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,935 Sq Ft

  11 Old Hill Rd, Westport, CT 06880

  Nestled in the heart of Westport's coveted Old Hill neighborhood, this home offers the charm of an English cottage and a thoughtful design that blends classic character with the modern desire for open, connected living. Encompassing nearly 4,000 square feet, it features four ensuite bedrooms, walk-in closets, and a curated layout that combines timeless architectural details with contemporary

  

  Susan Lieberman

  The Riverside Realty Group

  (475) 219-2239

  11 Old Hill Rd, Westport, CT 06880
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  /40

  $8,950 total monthly price

  • 4 Beds
  • 4.5 Baths
  • 3,436 Sq Ft
  • House for Rent

  96 Kings Hwy N, Westport, CT 06880

  Historic charm meets refined living in this award-winning Old Hill residence. Charming, sophisticated, and rich with history, this exceptional 4-5 BR vintage residence is one of Westport's most notable homes, ideally situated in the prestigious Old Hill area. Known as the David Judah House, the property has been painstakingly and lovingly preserved and restored and is the recipient of the Helen

  

  Judy Szablak

  Coldwell Banker Realty

  (203) 815-1968

  96 Kings Hwy N, Westport, CT 06880
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  $827,500 Sold May 05, 2025

  58 Southfield Rd, Fairfield, CT 06824

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • Built 1938

  Last Sold Summary

  • 10% Above List Price
  • $663/SF
  • 59 Days On Market

  Current Estimated Value $833,953

  Last Listing Agent Ken Banks William Raveis Real Estate

  58 Southfield Rd, Fairfield, CT 06824
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  Est $494,870 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  8 Hazel St, Fairfield, CT 06825

  8 Hazel St, Fairfield, CT 06825
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  /15

  $645,000 Pending

  • 8 Beds
  • 2 Baths
  • 2,849 Sq Ft

  74 Carleton Ave, Bridgeport, CT 06604

  Fully renovated two-family home with new floors and fresh paint. Each unit offers a bright living room with high ceilings and in-unit laundry hookups. The location is ideal and close to schools, shopping, and public transportation. Minutes from Metro North, I-95, grocery stores, restaurants, bus lines, and near Fairfield amenities. Seaside Park is a short drive for waterfront views and outdoor

  

  Rudy Pierre

  YellowBrick Real Estate LLC

  (475) 242-5962

  74 Carleton Ave, Bridgeport, CT 06604
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  /2

  $2,450 total monthly price

  • 3 Beds
  • 1 Bath
  • 22,736 Sq Ft
  • Apartment for Rent

  1589 Fairfield Ave Unit f15, Bridgeport, CT 06605

  Stunning, modern 3 bedroom apartment with heat and hot water included. Move in ready!

  

  Lisa Nussbaum

  Top Tier Realty Group, LLC

  (475) 323-4817

  1589 Fairfield Ave Unit f15, Bridgeport, CT 06605
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  $2,265,000 Sold Jul 16, 2025

  111 Pratt St, Fairfield, CT 06824

  • 4 Beds
  • 3.5 Baths
  • 3,248 Sq Ft
  • Built 2017

  Last Sold Summary

  • 14% Above List Price
  • $697/SF
  • 10 Days On Market

  Current Estimated Value $2,238,206

  Last Listing Agent Jen Kass Higgins Group Bedford Square

  111 Pratt St, Fairfield, CT 06824
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  Est $1,058,314 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,055 Sq Ft

  78 Oakwood Dr, Fairfield, CT 06824

  78 Oakwood Dr, Fairfield, CT 06824
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  /40

  $899,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft

  7 High Gate Rd, Westport, CT 06880

  A Greens Farms Opportunity with Character and Possibility Set in the heart of sought-after Greens Farms, this charming home offers both comfort today and exciting possibilities for tomorrow. With its Cape-to-Colonial design, the home combines character with a flexible layout-featuring two bedrooms on the main level and two upstairs. One of the spacious second-floor bedrooms could easily serve as

  

  Toni Mickiewicz

  William Pitt Sotheby's Int'l

  (203) 457-8947

  7 High Gate Rd, Westport, CT 06880
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  /19

  $3,800 total monthly price

  • 3 Beds
  • 3 Baths
  • 3,204 Sq Ft
  • House for Rent

  144 Rakoczy Ave, Fairfield, CT 06824

  Sprawling 3 Bedroom, 3 Bath, corner unit, mulit level unit in desirable Fairfield. Conveniently right off Black Rock Turnpike, between 95 & 15. Sq footage shown is per public records and is for full structure, this unit is approx half of that. Fully remodeled in 2022. Recently refreshed.

  

  Marc Walowitz

  Equity Realty Group, LLC

  (475) 255-3817

  144 Rakoczy Ave, Fairfield, CT 06824
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  $200,000 Sold Mar 26, 2025

  25 Cartright St, Bridgeport, CT 06604

  • 2 Beds
  • 1 Bath
  • 939 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Below List Price
  • $213/SF
  • 25 Days On Market

  Last Listing Agent Kashaine Ferryman U S Asset Realty LLC

  25 Cartright St, Bridgeport, CT 06604
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  Est $637,696 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,282 Sq Ft

  157 Oakwood Dr, Fairfield, CT 06824

  157 Oakwood Dr, Fairfield, CT 06824
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  /2

  $1,100,000 Open Mon 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 1,965 Sq Ft

  139 Field Point Dr, Fairfield, CT 06824

  This is the one you've been waiting for- they RARELY come up for sale! ... Welcome to The Meadows, where a hard to find one-level ranch living meets stunning, unobstructed marsh views,.... and this one checks every box! Enjoy easy single-level living with a spacious floor plan, hardwood floors throughout, crown molding, and sunlight pouring in from every angle. Step into a fabulous large foyer,

  

  Judy Szablak

  Coldwell Banker Realty

  (203) 693-9114

  139 Field Point Dr, Fairfield, CT 06824
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  /29

  $10,000 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 2,950 Sq Ft
  • House for Rent

  10 Tupelo Rd, Westport, CT 06880

  Step into a place where everyday living feels calm, comfortable, and connected to nature. This Coleytown home offers 4 bedrooms, 3.5 baths, and about 2,950 square feet of flexible space, including a finished lower level that adds room for hobbies, entertainment, or quiet work time. From the moment you pull into the cul-de-sac, you notice the low-traffic setting that gives the property a peaceful

  

  Pam Toner

  Berkshire Hathaway NE Prop.

  (475) 255-1469

  10 Tupelo Rd, Westport, CT 06880
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  $360,000 Sold Jul 09, 2025

  599 Laurel Ave, Bridgeport, CT 06605

  • 6 Beds
  • 3.5 Baths
  • 2,598 Sq Ft
  • Built 1910

  Last Sold Summary

  • 15% Below List Price
  • $139/SF
  • 53 Days On Market

  Current Estimated Value $391,370

  Last Listing Agent Ocilene De-Carvalho Century 21 Scala Group

  599 Laurel Ave, Bridgeport, CT 06605
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  Est $893,165 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,805 Sq Ft

  80 Sasapequan Rd, Fairfield, CT 06824

  80 Sasapequan Rd, Fairfield, CT 06824

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