Southport, CT Homes

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  /19

  $4,250,000 New Construction

  • 6 Beds
  • 9 Baths
  • 7,499 Sq Ft

  6 Janson Dr, Westport, CT 06880

  Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed

  

  Brett Lieberman

  The Riverside Realty Group

  (475) 330-3787

  6 Janson Dr, Westport, CT 06880
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  /14

  $12,000

  Total Monthly Price

  • 4 Beds
  • 3 Baths
  • 1,700 Sq Ft
  • House for Rent

  296 Reef Rd, Fairfield, CT 06824

  Tastefully FURNISHED 9 month rental beginning September 2027. Viking appliances. Spa showers. Patio. Easy stroll to downtown, train, shopping and beach. Up to 5 unrelated tenants. Co-signers accepted.

  296 Reef Rd, Fairfield, CT 06824
• 

  $1,000,000 Sold Nov 14, 2025

  74 Westford Dr, Southport, CT 06890

  • 3 Beds
  • 2.5 Baths
  • 2,609 Sq Ft
  • Built 1947

  Last Sold Summary

  • 5% Above List Price
  • $383/SF
  • 14 Days On Market

  Current Estimated Value $1,090,675

  Last Listing Agent Lauren Dunne Berkshire Hathaway NE Prop.

  74 Westford Dr, Southport, CT 06890
• 

  Est $604,373 Not Listed For Sale

  126 Churchill St, Fairfield, CT 06824

  • 4 Beds
  • 1 Bath
  • 1,787 Sq Ft
  • Built 1953

  126 Churchill St, Fairfield, CT 06824

  Last Sold Summary

  • 4% Above List Price
  • $325/SF
  • 16 Days On Market

  • Last Sold Price $580,000
  • Apr 25, 2025

  Last Listing Agent Benjamin Howell Coldwell Banker Realty
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  /7

  $995,000 New Construction

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

  53 Sterling St, Fairfield, CT 06825

  New construction townhome built by a respected local builder known for quality craftsmanship and clean, modern design. This residence offers approximately 2,300 square feet of above-grade living plus a finished lower level, thoughtfully laid out across three levels. The main floor features an open-concept design anchored by a well-appointed kitchen with white and white oak cabinetry, quartz

  Jessica Lane

  Serhant Connecticut, LLC

  (475) 269-4997

  53 Sterling St, Fairfield, CT 06825
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  /33

  $3,700 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,750 Sq Ft
  • Townhouse for Rent

  2 Beacon Square Unit 6, Fairfield, CT 06825

  Welcome to this lovely complex at Beacon Square in Fairfield. Each unit has its own individual garage with interior entrance to the first level. On the entry level, you'll find a large room that can be used as a guest bedroom, office, playroom...whatever you need. This ground level has a generous foyer with ample closets. Up one level is the main living area with a large open concept. The

  Lauren Dunne Berkshire Hathaway NE Prop.

  2 Beacon Square Unit 6, Fairfield, CT 06825
• 

  $565,000 Sold Dec 15, 2025

  670 Clinton Ave, Bridge Port, CT 06605

  • 1 Bed
  • 5,050 Sq Ft
  • Built 1916

  Last Sold Summary

  • 13% Below List Price
  • $112/SF
  • 84 Days On Market

  Current Estimated Value $566,752

  Last Listing Agent Carrie Braley Compass Connecticut, LLC

  670 Clinton Ave, Bridge Port, CT 06605
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  Est $772,703 Not Listed For Sale

  124 Szost Dr, Fairfield, CT 06824

  • 3 Beds
  • 2.5 Baths
  • 1,415 Sq Ft
  • Built 1953

  124 Szost Dr, Fairfield, CT 06824

  Last Sold Summary

  • 11% Above List Price
  • $492/SF
  • 23 Days On Market

  • Last Sold Price $695,800
  • May 01, 2025

  Last Listing Agent Cassandra Fowler BHGRE Gaetano Marra Homes
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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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  /15

  $2,000

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  21 Davenport Ave Unit 3, Westport, CT 06880

  Spacious one bedroom apartment, large bedroom with huge closet, separate eat-in kitchen. Convenient Westport location, access to compo Beach close to train, private, quiet neighborhood.

  21 Davenport Ave Unit 3, Westport, CT 06880
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  $1,900,000 Sold Jul 29, 2025

  53 Lower Farm Rd Unit lot 1, Fairfield, CT 06824

  • 4 Beds
  • 4.5 Baths
  • 4,147 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $458/SF
  • 130 Days On Market

  Last Listing Agent Linda Blackwell Houlihan Lawrence

  53 Lower Farm Rd Unit lot 1, Fairfield, CT 06824
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  Est $696,849 Not Listed For Sale

  296 Sigwin Dr, Fairfield, CT 06824

  • 3 Beds
  • 1.5 Baths
  • 1,444 Sq Ft
  • Built 1961

  296 Sigwin Dr, Fairfield, CT 06824

  Last Sold Summary

  • 11% Above List Price
  • $436/SF
  • 13 Days On Market

  • Last Sold Price $630,000
  • May 02, 2025

  Last Listing Agent Kathleen Eigenrauch Coldwell Banker Realty
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  /38

  $6,195,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,550 Sq Ft

  22 Apple Tree Trail, Westport, CT 06880

  Located on a quiet private lane just two blocks from Compo Beach, this newly built coastal residence at 22 Appletree Trail offers a rare combination of modern craftsmanship, thoughtful design, and effortless beach living in the heart of Westport. Spanning approximately 4,791 sq ft of living space, the home blends timeless architectural elements with refined contemporary finishes. White oak

  Deborah Aulfinger Gold & Home Realty

  22 Apple Tree Trail, Westport, CT 06880
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  /21

  $3,900 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,538 Sq Ft
  • House for Rent

  429 Round Hill Rd, Fairfield, CT 06824

  Welcome to 429 Round Hill Road, a beautifully updated Colonial rental that blends classic Fairfield charm with modern finishes and comfortable living. Inside, the home features a bright open layout with warm wood tone flooring, recessed lighting, and a spacious living and dining area that flows seamlessly into the updated kitchen. The kitchen is designed for both everyday living and entertaining

  Shane Mason-Fryer KW Legacy Partners

  429 Round Hill Rd, Fairfield, CT 06824
• 

  $725,000 Sold Jul 02, 2025

  179 Sterling St, Fairfield, CT 06825

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Above List Price
  • $340/SF
  • 17 Days On Market

  Current Estimated Value $738,582

  Last Listing Agent Carol Langeland William Pitt Sotheby's Int'l

  179 Sterling St, Fairfield, CT 06825
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  Est $1,031,178 Not Listed For Sale

  120 Mountain Laurel Rd, Fairfield, CT 06824

  • 4 Beds
  • 3 Baths
  • 2,800 Sq Ft
  • Built 1968

  120 Mountain Laurel Rd, Fairfield, CT 06824

  Last Sold Summary

  • 6% Above List Price
  • $348/SF
  • 19 Days On Market

  • Last Sold Price $975,000
  • Apr 30, 2025

  Last Listing Agent Polly Sykes Compass Connecticut, LLC
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  /34

  $2,450,000 Open Sat 1PM - 4PM

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

  171 Compo Rd S, Westport, CT 06880

  Tucked away in a peaceful, private setting, Hidden Ledge offers the best of Westport living in an ideal Saugatuck/Compo location. This stunning brand-new 4-5 bedroom home combines thoughtful design, quality craftmanship, and effortless access to the area's most loved destinations. Walk along sidewalks or bike the designated bike routes to Compo Beach, Longshore, Saugatuck, downtown shops,

  Tanya Sprague Coldwell Banker Realty

  171 Compo Rd S, Westport, CT 06880
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  /5

  $950

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,066 Sq Ft
  • Condo for Rent

  2660 North Ave Unit 114, Bridgeport, CT 06604

  Private room with private bathroom. Washer dryer in the unit. The condo is gated parking. All utilities included. Can be a longer lease if needed. Fully furnished.

  2660 North Ave Unit 114, Bridgeport, CT 06604
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  $750,000 Sold Mar 11, 2026

  41 Pepperbush Ln, Fairfield, CT 06824

  • 3 Beds
  • 2.5 Baths
  • 2,045 Sq Ft
  • Built 1976

  Last Sold Summary

  • $367/SF
  • 85 Days On Market

  Current Estimated Value $775,255

  Last Listing Agent Danielle Rownin Keller Williams Realty

  41 Pepperbush Ln, Fairfield, CT 06824
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  Est $780,492 Not Listed For Sale

  165 Halley Ave, Fairfield, CT 06825

  • 6 Beds
  • 2,761 Sq Ft
  • Built 1916

  165 Halley Ave, Fairfield, CT 06825

  Last Sold Summary

  • 4% Above List Price
  • $272/SF
  • 25 Days On Market

  • Last Sold Price $750,000
  • Apr 29, 2025

  Last Listing Agent Shan Guan Coraland Realty
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  /9

  $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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  /25

  $7,000 Per Month

  • 4 Beds
  • 2 Baths
  • 1,893 Sq Ft
  • House for Rent

  151 Sasapequan Rd, Fairfield, CT 06824

  Available for Winter/AY Rental August of 2027-June 2028. Rent could increase for future summer months depending on terms and contract length. Kayaks and Stand Up Paddle Boards available for lakeside fun! Conveniently located just minutes from the train station, shops, and restaurants and just 3 miles from Fairfield and Sacred Heart Universities. This newly updated waterfront home is located

  Cheryl Cusa Brown Harris Stevens

  151 Sasapequan Rd, Fairfield, CT 06824
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  $1,115,000 Sold Mar 06, 2026

  915 S Pine Creek Rd, Fairfield, CT 06824

  • 3 Beds
  • 1.5 Baths
  • 1,239 Sq Ft
  • Built 1960

  Last Sold Summary

  • 13% Above List Price
  • $900/SF
  • 6 Days On Market

  Current Estimated Value $968,524

  Last Listing Agent Celie Campbell Compass Connecticut, LLC

  915 S Pine Creek Rd, Fairfield, CT 06824
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  Est $1,857,854 Not Listed For Sale

  127 Lakeview Dr, Fairfield, CT 06825

  • 5 Beds
  • 4.5 Baths
  • 5,000 Sq Ft
  • Built 2025

  127 Lakeview Dr, Fairfield, CT 06825

  Last Sold Summary

  • 2% Below List Price
  • $380/SF
  • 48 Days On Market

  • Last Sold Price $1,900,000
  • May 02, 2025

  Last Listing Agent Kaitlyn Walsh William Raveis Real Estate
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  $3,899,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 4,693 Sq Ft

  11 Edgewater Hillside, Westport, CT 06880

  COMPO BEACH WATER VIEWS at this picture-perfect beach house. Edgewater Hillside is the best-kept secret at Compo Beach, a private Hamptons-style cul de sac where each home is prettier than the next and water views abound. This exceptional residence combines timeless design with high-end amenities and so much space to live and entertain, walking distance to Compo Beach and Old Mill Beach, and

  Cyd Hamer William Pitt Sotheby's Int'l

  11 Edgewater Hillside, Westport, CT 06880
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  /18

  $2,500

  Total Monthly Price

  • Studio
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  289 Spruce St, Southport, CT 06890

  Desirable Southport area off Post Road with close easy access to I95 on ramp and MetroNorth train station. Convenient to downtown Fairfield, Southport Harbor and shopping. Access to Fairfield beaches. Bottom floor apartment with garage and backyard access included.Owner pays for water only. All other utilities not included. First month rent, last and security deposit due at lease signing.

  289 Spruce St, Southport, CT 06890
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  $430,000 Sold Aug 21, 2025

  245 Unquowa Rd Unit 35, Fairfield, CT 06824

  • 1 Bed
  • 1 Bath
  • 902 Sq Ft
  • Built 1964

  Last Sold Summary

  • $477/SF
  • 12 Days On Market

  Current Estimated Value $441,044

  Last Listing Agent Mark Pires Coldwell Banker Realty

  245 Unquowa Rd Unit 35, Fairfield, CT 06824
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  Est $548,722 Not Listed For Sale

  515 Melville Ave, Fairfield, CT 06825

  • 3 Beds
  • 1.5 Baths
  • 960 Sq Ft
  • Built 1955

  515 Melville Ave, Fairfield, CT 06825

  Last Sold Summary

  • $573/SF
  • 8 Days On Market

  • Last Sold Price $550,000
  • May 01, 2025

  Last Listing Agent Kaitlin Fulco Coldwell Banker Milford
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  /39

  $2,799,000

  • 5 Beds
  • 4 Baths
  • 2,188 Sq Ft

  1235 Fairfield Beach Rd, Fairfield, CT 06824

  TWO incredible waterside opportunities await! That's right, not one, but TWO fantastic beach area homes are offered! With their direct waterfront locations (1235 - beachfront/LI Sound; 1236 - canal side), both homes have amazing water views, beach access and a convenient, fantastic location all in one! Both homes also offer excellent investment/rental opportunities. #1235 is rented for the

  John Foran Compass Connecticut, LLC

  1235 Fairfield Beach Rd, Fairfield, CT 06824
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  /24

  $60,000 Per Month

  • 6 Beds
  • 5.5 Baths
  • 3,989 Sq Ft
  • House for Rent

  23 Sterling Dr, Westport, CT 06880

  SUMMER RENTAL Overlooking Compo Cove beach. Water views from all rooms. Available for 2 periods: June 25th to July 25th and July 25th to August 23rd (there is some schedule flexibility). This recently built 5-bedroom home has a light-filled gourmet kitchen with 2 sinks, 2 dishwashers, and Sub-Zero/Wolf appliances. The Living area and kitchen open to the pool, fenced in yard (perfect for young

  Derek Greene Derek Greene

  23 Sterling Dr, Westport, CT 06880
• 

  $1,750,000 Sold Nov 14, 2025

  130 Easton Rd, Westport, CT 06880

  • 6 Beds
  • 5.5 Baths
  • 5,489 Sq Ft
  • Built 1958

  Last Sold Summary

  • 22% Below List Price
  • $319/SF
  • 130 Days On Market

  Current Estimated Value $1,827,883

  Last Listing Agent David Weber Compass Connecticut, LLC

  130 Easton Rd, Westport, CT 06880
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  Est $816,681 Not Listed For Sale

  220 King St, Bridgeport, CT 06605

  • 6 Beds
  • 3 Baths
  • 3,189 Sq Ft
  • Built 1960

  220 King St, Bridgeport, CT 06605

  Last Sold Summary

  • 2% Above List Price
  • $251/SF
  • 23 Days On Market

  • Last Sold Price $801,000
  • May 02, 2025

  Last Listing Agent Timothy Dailey Higgins Group Real Estate
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  $2,200,000

  • 5 Beds
  • 4.5 Baths
  • 6,330 Sq Ft

  25 Old Rd, Westport, CT 06880

  Set in Westport's sought-after Hunt Club neighborhood, this European-inspired Colonial offers over 6,300 square feet across three finished levels, including expansive recreation spaces and a dedicated home theater. A dramatic two-story entry introduces refined formal and informal rooms, including a fireplaced living room, formal dining room, private office, and an expansive eat-in kitchen with

  Zach Wright William Pitt Sotheby's Int'l

  25 Old Rd, Westport, CT 06880
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  /21

  $2,500

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  27 Harborview Ave Unit 2nd Floor, Bridgeport, CT 06605

  Coastal Living in Black Rock – Fully Renovated 2BR with Off Street Parking!Rent: $2,500/monthAvailable: June 1st, 2026Location: 27 Harborview Ave, 2nd Floor (Black Rock)The OpportunityRarely available! Secure a beautiful, fully renovated apartment on one of Black Rock’s most desirable residential streets. This second-floor unit in a quiet 3-family home offers

  27 Harborview Ave Unit 2nd Floor, Bridgeport, CT 06605
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  $315,000 Sold Sep 12, 2025

  850 Brewster St, Bridgeport, CT 06605

  • 2 Beds
  • 1 Bath
  • 1,224 Sq Ft
  • Built 1937

  Last Sold Summary

  • 7% Above List Price
  • $257/SF
  • 35 Days On Market

  Current Estimated Value $348,294

  Last Listing Agent Cisco Borres RE/MAX Right Choice

  850 Brewster St, Bridgeport, CT 06605
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  Est $402,996 Not Listed For Sale

  87 Ellsworth St, Bridgeport, CT 06605

  • 2 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1856

  87 Ellsworth St, Bridgeport, CT 06605

  Last Sold Summary

  • 7% Above List Price
  • $221/SF
  • 17 Days On Market

  • Last Sold Price $376,000
  • Apr 25, 2025

  Last Listing Agent Susan Frederico Aspen Realty Group
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  /40

  $2,199,000 Open Sat 1PM - 4PM

  • 5 Beds
  • 4.5 Baths
  • 3,380 Sq Ft

  24 Burr School Rd, Westport, CT 06880

  Tucked away towards the end of a quiet cul-de-sac in a prime central Westport location, this beautifully updated home offers the perfect blend of privacy, convenience, and lifestyle. Set on 1.05 acres and just moments from town, close to schools, shopping, and commuting options, this five-bedroom residence is designed for both everyday living and effortless entertaining. The heart of the home is

  Julia Broder Coldwell Banker Realty

  24 Burr School Rd, Westport, CT 06880
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  /17

  $5,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft
  • House for Rent

  788 Reef Rd, Fairfield, CT 06824

  Welcome to your dream beach getaway! This beautifully renovated three-bedroom, one-bathroom beach home is ideally situated just a short walk to the beach, town, shopping, and more! With a fresh update in 2025, this fully furnished retreat combines comfort and style, making it perfect for both relaxing weekends and year-round living. Three Spacious Bedrooms: Ample space for family and guests.

  Meg Schwanhausser Compass Connecticut, LLC

  788 Reef Rd, Fairfield, CT 06824
• 

  $1,450,000 Sold Mar 05, 2026

  785 Post Rd E Unit 301, Westport, CT 06880

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Built 2025

  Last Sold Summary

  • $1,115/SF
  • 90 Days On Market

  Last Listing Agent Todd Gibbons Boost Real Estate Group

  785 Post Rd E Unit 301, Westport, CT 06880
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  Est $625,300 Not Listed For Sale

  80 Beachview Ave, Bridgeport, CT 06605

  • 3 Beds
  • 1 Bath
  • 1,090 Sq Ft
  • Built 1980

  80 Beachview Ave, Bridgeport, CT 06605

  Last Sold Summary

  • $573/SF
  • 20 Days On Market

  • Last Sold Price $625,000
  • May 07, 2025

  Last Listing Agent Katie O'Grady Compass Connecticut, LLC

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