Southport, CT Homes

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  /10

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,460 Sq Ft

  500 Dewey St, Bridgeport, CT 06605

  Please DO NOT DISTURB the occupant. Contact with occupants is prohibited. Opportunity to own a charming colonial-style home constructed in 1937. Offering over 1,400 square feet of living space, features 3 bedrooms and 1 full bathroom. This property includes the added benefit of off-street parking, ensuring ease and accessibility. Step outside into your own private fenced backyard ideal for family

  Jonathan Gineo Silver and Oak Realty

  500 Dewey St, Bridgeport, CT 06605
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  /40

  $50,000 total monthly price

  • 5 Beds
  • 5 Baths
  • 3,955 Sq Ft
  • House for Rent

  50 Compo Mill Cove, Westport, CT 06880

  Fully Furnished, WATERFRONT PARADISE! Tranquil location offers unrivaled access to Panoramic Ocean views of Long Island Sound. A short walk across the Wooden Footbridge w/ Sherwood Mill Pond on your left and LI Sound on your right leads to the gated private Island of Compo Mill Cove & a handful of unique waterfront homes. The property itself has been customized from top to bottom w/ exceptional

  Robert Perriello Century 21 AllPoints Realty

  50 Compo Mill Cove, Westport, CT 06880
• 

  $2,700,000 Sold Oct 30, 2025

  • 3,703 Sq Ft
  • $729/SF
  • 42 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1835

  2821 Congress St, Fairfield, CT 06824

  Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A

  Andrew Whiteley Brown Harris Stevens

  2821 Congress St, Fairfield, CT 06824
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  Est $3,712,022 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,456 Sq Ft

  9 Murvon Ct, Westport, CT 06880

  9 Murvon Ct, Westport, CT 06880
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  /14

  $149,900

  • 1 Bath
  • 629 Sq Ft

  80 Cartright St Unit 8B, Bridgeport, CT 06604

  Discover a rare opportunity to own a beautifully updated studio unit in Cartright Towers, a well-maintained building on the Fairfield/Bridgeport line. Whether you're an investor seeking strong rental potential or a buyer looking for a move-in ready home, this immaculate unit checks every box. Enjoy the convenience and security of full-time doorman service, plus amenities including elevators,

  Hillary Waite William Raveis Real Estate

  80 Cartright St Unit 8B, Bridgeport, CT 06604
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  /55

  $6,950 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  116 Sherman St, Fairfield, CT 06824

  Embrace the ultimate in sophistication, exclusivity, and style with this stunning two-bedroom, two-bath apartment located in the heart of Downtown Fairfield. With breathtaking panoramic views and an abundance of natural light streaming through a full wall of windows, this home is designed to impress from every angle. Inside, enjoy contemporary features including integrated lighting that creates a

  116 Sherman St, Fairfield, CT 06824
• 

  $1,450,000 Sold Oct 30, 2025

  • 2,794 Sq Ft
  • $519/SF
  • 14 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2024

  175 Alma Dr, Fairfield, CT 06824

  Beautiful new colonial in the University neighborhood situated on the serene Mill River. Completely rebuilt in 2024-with only the foundation and one wall remaining-this stunning home blends timeless design with modern luxury. Every detail has been thoughtfully crafted, showcasing high-end finishes throughout. The heart of the home is the luxury Christopher Peacock kitchen, featuring a spacious

  Annie Kruger Brown Harris Stevens

  175 Alma Dr, Fairfield, CT 06824
• 

  Est $1,174,561 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,540 Sq Ft

  18 Highland Rd, Westport, CT 06880

  18 Highland Rd, Westport, CT 06880
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  /40

  $699,999

  • 3 Beds
  • 2 Baths
  • 1,382 Sq Ft

  53 Hilltop Dr, Southport, CT 06890

  Step into 53 Hilltop Drive - your entrance into the Southport community. This lovingly maintained 1949 Cape Cod brimming with charm, natural light, and classic New England character. This inviting home offers 3 bedrooms, 2 full bathrooms, and 1,382 sq. ft. of comfortable living, with timeless hardwood floors, a partially finished basement, and an attached garage. Flooded with sunlight, the living

  Kaitlin Fulco Coldwell Banker Realty

  53 Hilltop Dr, Southport, CT 06890
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  /40

  $28,000 total monthly price

  • 5 Beds
  • 4.5 Baths
  • 14,038 Sq Ft
  • House for Rent

  11 Beachside Common, Westport, CT 06880

  Short term fully furnished rental. Direct waterfront in Greens Farms. A true Westport icon, 11 Beachside Common is one of the most architecturally distinctive homes on the Connecticut coast-known to anyone who's ever strolled Burying Hill Beach. Set on 2.6 waterfront acres, the property offers sweeping southern views over Sherwood Island and Long Island Sound, with sunsets that rival the Low

  Andrew Whiteley Brown Harris Stevens

  11 Beachside Common, Westport, CT 06880
• 

  $4,850,000 Sold Oct 30, 2025

  • 10,906 Sq Ft
  • $445/SF
  • 46 Days On Market

  • 6 Beds
  • 8 Baths
  • Built 2000

  14 Mayflower Pkwy, Westport, CT 06880

  Stunning, grandly-scaled & remarkably-built stone & shingle classic located in THE quintessential, Compo Beach neighborhood (quieter & NOT in the flood plain) w/expansive, private, level property, embraced by stone walls & scenic entertaining opportunities 2nd to none. Just a short walk to celebrated Westport beaches, Longshore Club, Saugatuck Center & Metro Nth Station footpath, in coveted AA

  Joni Usdan Coldwell Banker Realty

  14 Mayflower Pkwy, Westport, CT 06880
• 

  Est $1,808,739 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,773 Sq Ft

  337 Greens Farms Rd, Westport, CT 06880

  337 Greens Farms Rd, Westport, CT 06880
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  /39

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  28 Crescent Park Rd, Westport, CT 06880

  3-bedroom ranch-style home completely remodeled in coveted Westport. Featuring an inviting open floor plan, this thoughtfully renovated residence creates a perfect flow for modern living and entertaining. The home showcases a private master suite with contemporary finishes, and a large primary bathroom, while the open-concept main living areas are bathed in natural light. Following a complete

  Karim Douich William Raveis Real Estate

  28 Crescent Park Rd, Westport, CT 06880
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  /25

  $2,650 total monthly price

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft
  • House for Rent

  100 Silliman St Unit 1, Fairfield, CT 06824

  A bright and cheerful 2-bedroom 1-bath condo tucked in a wonderfully convenient location on cue de sac. The home opens into living room with dining area, kitchen with gas range, refrigerator and microwave, Both bedrooms offer comfortable space and full bath with tub. Coin Laundry facilities in basement. The building sits to everyday essentials: shopping, dining, and commuter routes. 1 dedicated

  Cristy Schnauffer Coldwell Banker Realty

  100 Silliman St Unit 1, Fairfield, CT 06824
• 

  $780,000 Sold Oct 30, 2025

  • 1,728 Sq Ft
  • $451/SF
  • 28 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  55 Thorpe St, Fairfield, CT 06824

  Tucked away in the heart of Fairfield Center you have found 55 Thorpe St. This tri-level townhouse is deceivingly spacious. Entry way provides access from the Tandem two car garage, long hall way with ample storage leading you to the rear bonus Den/office with walk out to private green space. As you walk up the staircase to the main level you are greeted with an amazing open concept space and 9ft

  Ashley Petrides William Raveis Real Estate

  55 Thorpe St, Fairfield, CT 06824
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  Est $3,165,138 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,381 Sq Ft

  29 Fairfield Ave, Westport, CT 06880

  29 Fairfield Ave, Westport, CT 06880
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  /33

  $112,000

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  217 Alsace St, Bridgeport, CT 06604

  Move-in ready two bedroom Townhouse in Desirable Historic Seaside Village, offers a spacious eat-in kitchen, living room, full bath on main floor and two bedroom on second floor. Very clean basement with washer and dryer. Privacy and serenity of spacious fenced-in yard, perfect for out door activities and entertaining. walk to Seaside Park with beautifull beach and University Bridgeport campus.

  Victoria Bui Larracuente & Johnson Realty, LLC

  217 Alsace St, Bridgeport, CT 06604
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  /6

  $2,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 5,824 Sq Ft
  • Apartment for Rent

  25 Whittier St Unit 5, Bridge Port, CT 06605

  Be the first to enjoy this brand-newly renovated 2-bedroom apartment in Bridgeport's highly sought-after Black Rock neighborhood. This unit features all-new modern finishes and is designed for convenient living, being located steps away from all local amenities and major bus lines. A huge bonus is the dedicated off-street parking spot available.

  Pape Ndao RE/MAX Right Choice

  25 Whittier St Unit 5, Bridge Port, CT 06605
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  $1,075,000 Sold Oct 30, 2025

  • 1,450 Sq Ft
  • $741/SF
  • 17 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1910

  9 Clinton Ave, Westport, CT 06880

  Full of character and cottage-style comfort, this farmhouse offers an inviting blend of vintage charm and modern living. The large, welcoming front porch sets the tone-a perfect spot to sip coffee, greet neighbors, or simply unwind. Inside, the main level features an open country kitchen-perfect for gathering with family and friends-while natural sunlight fills every corner. The cozy living room

  Linda Dunsmore Keller Williams Realty

  9 Clinton Ave, Westport, CT 06880
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  Est $2,430,198 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,648 Sq Ft

  8 Darbrook Rd, Westport, CT 06880

  8 Darbrook Rd, Westport, CT 06880
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  /40

  $4,435,000

  • 4 Beds
  • 4 Baths
  • 4,446 Sq Ft

  11 Sterling Dr, Westport, CT 06880

  Nestled in privacy by nearly 100 arborvitaes, this ultimate retreat on a rare double lot is just steps from Old Mill Beach & Compo Beach. The home distinguishes itself by offering water views from nearly every room & from the expansive decks located on multiple levels. Fully remodeled & expanded in 2018, this thoughtfully designed home features oversized windows to enjoy spectacular sunrises &

  Janice McGrath O'Brien William Raveis Real Estate

  11 Sterling Dr, Westport, CT 06880
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  /18

  $4,500 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,145 Sq Ft
  • Townhouse for Rent

  301 Post Rd E Unit 8, Westport, CT 06880

  Centrally located, Playhouse Condominiums are just steps from town, Winslow Park, shops, restaurants, and more. This unit features beautiful hardwood floors throughout. The main living and dining area offers sky-high ceilings, large windows, and a wood-burning fireplace. The updated kitchen includes granite countertops and stainless-steel appliances. The first-floor bath also includes in-unit

  Mary Ann Lindwall The Riverside Realty Group

  301 Post Rd E Unit 8, Westport, CT 06880
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  $1,200,000 Sold Oct 30, 2025

  • 2,164 Sq Ft
  • $555/SF
  • 20 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1950

  115 Dwight St, Fairfield, CT 06824

  PLEASE SUBMIT OFFERS BY 6/3/25 AT 11:00 AM Welcome to "The Sunshine House"- that's what the current owner lovingly calls this charming and tastefully expanded Cape located at the end of one of the few cul-de-sacs in the coveted Fairfield Beach area. This 4 bedroom / 2full bath home offers over 2,100 square feet of light-filled living space and has been freshly painted throughout. Step into a

  Christine Ward Berkshire Hathaway NE Prop.

  115 Dwight St, Fairfield, CT 06824
• 

  Est $2,357,900 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,620 Sq Ft

  5 Thomas Rd, Westport, CT 06880

  5 Thomas Rd, Westport, CT 06880
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  /40

  $1,600,000

  • 5 Beds
  • 4.5 Baths
  • 3,159 Sq Ft

  226 Ruane St, Fairfield, CT 06824

  Welcome to your dream come true lifestyle in the heart of Fairfield's coveted beach/town community-where coastal charm meets everyday convenience. This brand-new modern Colonial is more than a home, it's an upgraded living experience. Imagine morning walks to South Pine Creek Beach, afternoons on the tennis courts or golf course & evenings dining at vibrant restaurants, live music & theatres

  Julie Vanderblue Higgins Group Real Estate

  226 Ruane St, Fairfield, CT 06824
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  /6

  $2,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 5,824 Sq Ft
  • Apartment for Rent

  25 Whittier St Unit 6, Bridge Port, CT 06605

  Be the first to enjoy this brand-newly renovated 2-bedroom apartment in Bridgeport's highly sought-after Black Rock neighborhood. This unit features all-new modern finishes and is designed for convenient living, being located steps away from all local amenities and major bus lines. A huge bonus is the dedicated off-street parking spot available.

  Pape Ndao RE/MAX Right Choice

  25 Whittier St Unit 6, Bridge Port, CT 06605
• 

  $1,290,000 Sold Oct 30, 2025

  • 3,360 Sq Ft
  • $384/SF
  • 39 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1967

  545 Surrey Ln, Fairfield, CT 06824

  Classic four bedroom, 2.5 bath colonial strikes a rare balance, offering turnkey charm, space and modern updates on a superb, manicured acre - all within one of Fairfield's most coveted neighborhoods. Set on a quiet tree-lined street in lower Greenfield Hill with a new roof, newer windows and air conditioner paired with fresh paint ensures lasting curb appeal and peace of mind. The well-appointed

  Kelly Finn Coldwell Banker Realty

  545 Surrey Ln, Fairfield, CT 06824
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  Est $1,142,580 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,044 Sq Ft

  6 Pondside Dr, Westport, CT 06880

  6 Pondside Dr, Westport, CT 06880
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  /27

  $975,000

  • 3 Beds
  • 3.5 Baths
  • 2,456 Sq Ft

  21 Beaumont St, Fairfield, CT 06824

  Luxury end-unit 3 bedroom / 3.5 bath townhouse in downtown Fairfield! This home offers a private 4-story in-unit elevator, attached 2-car garage, 2 primary suite options, 9+ foot ceilings, walk-in closets, abundant natural light, and more. The main level features a chef's kitchen with island seating, quartz countertops, Thermador appliances, and a pantry. The kitchen opens to a spacious great

  Carrie Sakey Coldwell Banker Realty

  21 Beaumont St, Fairfield, CT 06824
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  /4

  $2,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 5,824 Sq Ft
  • Apartment for Rent

  31 Whittier St Unit 2B, Bridge Port, CT 06605

  Be the first to enjoy this brand-newly renovated 2-bedroom apartment in Bridgeport's highly sought-after Black Rock neighborhood. This unit features all-new modern finishes and is designed for convenient living, being located steps away from all local amenities and major bus lines. A huge bonus is the dedicated off-street parking spot available.

  Pape Ndao RE/MAX Right Choice

  31 Whittier St Unit 2B, Bridge Port, CT 06605
• 

  $4,275,000 Sold Oct 30, 2025

  • 7,468 Sq Ft
  • $572/SF
  • 96 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2025

  86 Old Rd, Westport, CT 06880

  Magnificent move-in ready new construction brought to you by Sound Home Builders. Centrally located in the heart of Westport's coveted Long Lots, Hunt Club and Greens Farms neighborhoods. Elegant design and finishing detail, soaring ceilings and master craftsmanship throughout. Oversized European windows and doors fill the home with natural light. The kitchen features custom cabinetry, warm hues,

  Tom Preston Keller Williams Realty

  86 Old Rd, Westport, CT 06880
• 

  Est $958,962 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,472 Sq Ft

  25 Crescent Rd, Westport, CT 06880

  25 Crescent Rd, Westport, CT 06880
• 

  

  /40

  $4,995,000

  • 5 Beds
  • 4.5 Baths
  • 4,191 Sq Ft

  2281 Redding Rd, Fairfield, CT 06824

  Feels like Litchfield. Lives like Fairfield. Tucked behind a private gate in Greenfield Hill, this estate offers what few properties can: sweeping space, true privacy, and serene beauty-just 60 miles from Manhattan. A long stone drive leads to the 1941 main residence, reimagined with timeless craftsmanship. Sunlight floods rooms finished with reclaimed wood beams and wide-plank floors. The chef's

  Cindy Raney Coldwell Banker Realty

  2281 Redding Rd, Fairfield, CT 06824
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  /5

  $2,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 5,824 Sq Ft
  • Apartment for Rent

  31 Whittier St Unit 3B, Bridge Port, CT 06605

  Be the first to enjoy this brand-newly renovated 2-bedroom apartment in Bridgeport's highly sought-after Black Rock neighborhood. This unit features all-new modern finishes and is designed for convenient living, being located steps away from all local amenities and major bus lines. A huge bonus is the dedicated off-street parking spot available.

  Pape Ndao RE/MAX Right Choice

  31 Whittier St Unit 3B, Bridge Port, CT 06605
• 

  $1,390,000 Sold Oct 29, 2025

  • 1,416 Sq Ft
  • $982/SF
  • 51 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2025

  785 Post Rd E Unit 203, Westport, CT 06880

  AMAZING NEW CONSTRUCTION! Located in the heart of Westport, The Gables of Westport presents a collection of eight townhomes and five flats, blending sophisticated design with the ease of in-town living. Enjoy close proximity to Metro-North, major highways, Longshore Club & Park, Compo Beach, Levitt Pavilion, Westport Country Playhouse, fine dining, shopping, and entertainment. Crafted by local

  Todd Gibbons Boost Real Estate Group

  785 Post Rd E Unit 203, Westport, CT 06880
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  Est $1,984,821 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,548 Sq Ft

  25 Colony Rd, Westport, CT 06880

  25 Colony Rd, Westport, CT 06880
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  /12

  $685,000

  • 6 Beds
  • 3 Baths
  • 3,069 Sq Ft

  195 Lenox Ave Unit 197, Bridgeport, CT 06605

  Welcome to 195 Lenox Avenue - a modern and versatile 3-family home perfect for both investors and first-time buyers. With 6 bedrooms, 3 full bathrooms, and a full basement, this property offers plenty of space and excellent rental potential. The first and second floors each allow for an extra bedroom conversion, maximizing cash flow. Inside, the units are updated and well-maintained, providing

  Shafran Salim Guy Bocicaut Real Estate

  195 Lenox Ave Unit 197, Bridgeport, CT 06605
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  /5

  $2,000 total monthly price

  • 2 Beds
  • 1 Bath
  • 5,824 Sq Ft
  • Apartment for Rent

  31 Whittier St Unit 3A, Bridge Port, CT 06605

  Be the first to enjoy this brand-newly renovated 2-bedroom apartment in Bridgeport's highly sought-after Black Rock neighborhood. This unit features all-new modern finishes and is designed for convenient living, being located steps away from all local amenities and major bus lines. A huge bonus is the dedicated off-street parking spot available.

  Pape Ndao RE/MAX Right Choice

  31 Whittier St Unit 3A, Bridge Port, CT 06605
• 

  $582,500 Sold Oct 29, 2025

  • 1,124 Sq Ft
  • $518/SF
  • 83 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1918

  130 Massachusetts Ave, Fairfield, CT 06824

  Charming 2-Bedroom Colonial in Fairfield's Grasmere Neighborhood Welcome to this beautifully maintained 2-bedroom, 2-bath Colonial in the desirable Grasmere neighborhood of Fairfield, just blocks from the train station for an easy NYC/New Haven commute! Combining classic charm with thoughtful updates, this home is move-in ready and full of modern conveniences. Step inside to a bright and inviting

  Tiffany French Berkshire Hathaway NE Prop.

  130 Massachusetts Ave, Fairfield, CT 06824
• 

  Est $4,310,857 Not Listed For Sale

  • 6 Beds
  • 7.5 Baths
  • 11,231 Sq Ft

  11 Over Rock Ln, Westport, CT 06880

  11 Over Rock Ln, Westport, CT 06880

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