Southport, CT Homes

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  /38

  $2,095,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,328 Sq Ft

  32 Berndale Dr, Westport, CT 06880

  OFFERS DUE AT NOON ON MONDAY APRIL 13TH! In the heart of Westport, where charm meets modern living, the expanded cape at 32 Berndale Drive delivers the perfect blend of space, style, and location. Nestled on a quiet, sought-after street just moments from Bedford Middle School and Staples High School, this 5-bedroom, 4-bath residence offers exceptional versatility for today's lifestyle. A

  Kim Harizman Compass Connecticut, LLC

  32 Berndale Dr, Westport, CT 06880
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  /26

  $2,700 Per Month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  528 Black Rock Turnpike Unit 108, Fairfield, CT 06825

  Experience all-inclusive, maintenance-free living in this brand-new 23-unit apartment building just a short walk from the Fairfield Metro Train Station. This spacious two-bedroom, one-bath residence features an open floor plan with sleek, modern finishes. Enjoy a stylish eat-in kitchen complete with quartz countertops and stainless-steel appliances, as well as a generously sized bathroom. The

  Sara Santos Coldwell Banker Realty

  528 Black Rock Turnpike Unit 108, Fairfield, CT 06825
• 

  $589,000 Sold Oct 02, 2025

  157 Brentwood Ave Unit 157, Fairfield, CT 06825

  • 4 Beds
  • 3.5 Baths
  • 1,901 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Above List Price
  • $310/SF
  • 77 Days On Market

  Current Estimated Value $614,596

  Last Listing Agent Shoshana Snyder William Raveis Real Estate

  157 Brentwood Ave Unit 157, Fairfield, CT 06825
• 

  Est $4,217,536 Not Listed For Sale

  11 Over Rock Ln, Westport, CT 06880

  • 6 Beds
  • 7.5 Baths
  • 11,231 Sq Ft
  • Built 2004

  11 Over Rock Ln, Westport, CT 06880

  Last Sold Summary

  • 16% Below List Price
  • $445/SF
  • 47 Days On Market

  • Last Sold Price $5,000,000
  • Jun 16, 2023

  Last Listing Agent Karen Scott Compass Connecticut, LLC
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  /40

  $2,799,999 Pending

  • 5 Beds
  • 6.5 Baths
  • 7,269 Sq Ft

  342 Midlock Rd, Fairfield, CT 06824

  Welcome to an unrivaled sanctuary of sophistication at 342 Midlock Road, gracefully situated in the prestigious enclave of Greenfield Hill. This stately residence, perched on a coveted cul-de-sac off Burr Street, unfurls over two lush acres of meticulously manicured, fully fenced grounds. Upon entry, be enveloped in luxury as you traverse through spaces adorned with custom millwork, nine ft

  AJ Letterman Compass Connecticut, LLC

  342 Midlock Rd, Fairfield, CT 06824
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  /33

  $2,800 Per Month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  66 Hillandale Rd Unit 2, Fairfield, CT 06825

  Kitchen updated w/quartz counters, hi-arc faucet and ss sink, new vinyl plank floor, plus Samsung, programable. convection, air fryer range. Refrigerator, dishwasher and microwave included. Refinished hardwood floors and freshly painted throughout, updated bath, CAC and newer windows. Beautiful views from the newly refurbished sunroom. Square footage is approximate. Owner/agent. Owner will credit

  Judith Higgins Coldwell Banker Realty

  66 Hillandale Rd Unit 2, Fairfield, CT 06825
• 

  $2,060,000 Sold Jul 30, 2025

  180 Merwins Ln, Fairfield, CT 06824

  • 4 Beds
  • 5 Baths
  • 5,081 Sq Ft
  • Built 1958

  Last Sold Summary

  • 6% Above List Price
  • $405/SF
  • 11 Days On Market

  Current Estimated Value $2,107,592

  Last Listing Agent Shoshana Snyder William Raveis Real Estate

  180 Merwins Ln, Fairfield, CT 06824
• 

  Est $1,941,751 Not Listed For Sale

  6 River Oaks Rd, Westport, CT 06880

  • 4 Beds
  • 3 Baths
  • 2,364 Sq Ft
  • Built 1953

  6 River Oaks Rd, Westport, CT 06880

  Last Sold Summary

  • 8% Above List Price
  • $761/SF
  • 12 Days On Market

  • Last Sold Price $1,800,000
  • Jun 11, 2024

  Last Listing Agent Barbara Bross Coldwell Banker Realty
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  /40

  $429,900 Pending

  • 2 Beds
  • 1 Bath
  • 791 Sq Ft

  165 Bennett St, Bridgeport, CT 06605

  Nestled in the heart of Black Rock.......Welcome to Evergreen Cottage! The perfect blend of Simplicity, comfort & Tranquility! Beautifully maintained and rich in details such as high ceilings, craftsman-style moldings , crisp decor & an abundance of natural light in every room. Updated kitchen and bath, gas furnace & sewer line. Roof fully replaced 2021. Original cedar clapboards and trim

  Mary Amenda William Pitt Sotheby's Int'l

  165 Bennett St, Bridgeport, CT 06605
• 

  

  /23

  $4,750 Per Month

  • 2 Beds
  • 2 Baths
  • 1,182 Sq Ft
  • House for Rent

  20 Cross St Unit 5, Westport, CT 06880

  Turnkey two-bedroom, two-bath townhouse in Riverside Walk puts you in the heart of Westport. Walk to Starbucks, Bedford Square dining, Main Street shops, and summer concerts at the Levitt Pavilion. A private elevator brings you from your reserved garage space to bright single-level living with ceilings over nine feet high on both floors and hardwood throughout. The white kitchen offers granite

  Inna Agujen Coldwell Banker Realty

  20 Cross St Unit 5, Westport, CT 06880
• 

  $1,185,000 Sold Sep 10, 2025

  11 Catamount Rd, Westport, CT 06880

  • 5 Beds
  • 3 Baths
  • 2,564 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $462/SF
  • 89 Days On Market

  Current Estimated Value $1,268,718

  Last Listing Agent Kathleen O'Connell Coldwell Banker Realty

  11 Catamount Rd, Westport, CT 06880
• 

  Est $2,032,198 Not Listed For Sale

  1 Stone Dr, Westport, CT 06880

  • 5 Beds
  • 5 Baths
  • 3,800 Sq Ft
  • Built 1965

  1 Stone Dr, Westport, CT 06880

  Last Sold Summary

  • 25% Above List Price
  • $428/SF
  • 39 Days On Market

  • Last Sold Price $1,625,000
  • Jul 12, 2023

  Last Listing Agent Meredith Cohen Serhant Connecticut, LLC
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  /39

  $2,100,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 4.5 Baths
  • 4,494 Sq Ft

  276 Flintlock Rd, Southport, CT 06890

  Stunning in Southport! Nestled in a sought-after enclave of quiet streets and cul-de-sacs, lined with blooming Dogwood trees, this beautifully renovated 4 bed, 4.5 bath Colonial is ready to be enjoyed! The dream kitchen boasts a massive island, top of the line appliances, and a large sunny eating area with sliders to the deck! The open kitchen flows to the airy family room, living room and

  Leslie Clarke Compass Connecticut, LLC

  276 Flintlock Rd, Southport, CT 06890
• 

  

  /23

  $1,950 Per Month

  • 3 Beds
  • 1 Bath
  • 1,765 Sq Ft
  • House for Rent

  784 Howard Ave Unit 2nd Floor, Bridgeport, CT 06605

  Welcome to 784 Howard Avenue, 2nd floor, where timeless charm meets everyday convenience in this spacious and inviting rental set in a highly walkable Bridgeport location. From the moment you step inside, you are greeted by warm hardwood floors, abundant natural light, and a layout that feels both open and comfortable, creating the perfect backdrop for daily living and entertaining. The kitchen

  Daniel Leyden KW Legacy Partners

  784 Howard Ave Unit 2nd Floor, Bridgeport, CT 06605
• 

  $4,775,000 Sold Aug 04, 2025

  165 Bayberry Ln, Westport, CT 06880

  • 6 Beds
  • 9 Baths
  • 7,594 Sq Ft
  • Built 2015

  Last Sold Summary

  • 4% Below List Price
  • $629/SF
  • 143 Days On Market

  Current Estimated Value $4,958,462

  Last Listing Agent Pamela Cornfield Coldwell Banker Realty

  165 Bayberry Ln, Westport, CT 06880
• 

  Est $922,678 Not Listed For Sale

  4 Willowbrook Dr, Westport, CT 06880

  • 2 Beds
  • 2 Baths
  • 1,376 Sq Ft
  • Built 1962

  4 Willowbrook Dr, Westport, CT 06880

  Last Sold Summary

  • 22% Above List Price
  • $549/SF
  • 32 Days On Market

  • Last Sold Price $755,000
  • Mar 05, 2024

  Last Listing Agent Daniel Martin Higgins Group Real Estate
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  /14

  $999,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,756 Sq Ft

  201 Bradley Ln Unit 201, Westport, CT 06880

  Welcome to Bradley Commons, a private gated enclave in the heart of Westport's vibrant Saugatuck neighborhood-just minutes to the train, Compo Beach, top-rated schools, and premier dining and shopping. This exceptional end-unit townhome features a bright open floor plan with hardwood floors, high ceilings, and abundant natural light. The chef's kitchen offers granite countertops, gas range,

  Maxxwell Crowley S.C.A. Crowley Real Estate

  201 Bradley Ln Unit 201, Westport, CT 06880
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  /26

  $7,500 Per Month

  • 4 Beds
  • 2.5 Baths
  • 1,542 Sq Ft
  • House for Rent

  18 Hales Rd, Westport, CT 06880

  XXXXX

  Scott Kelland CLS Group

  18 Hales Rd, Westport, CT 06880
• 

  $2,210,000 Sold Apr 01, 2026

  204 Glen Ridge Rd, Fairfield, CT 06825

  • 5 Beds
  • 4.5 Baths
  • 4,474 Sq Ft
  • Built 2026

  Last Sold Summary

  • 11% Above List Price
  • $494/SF
  • 4 Days On Market

  Current Estimated Value $1,922,332

  Last Listing Agent Jennifer DeLaurentis Compass Connecticut, LLC

  204 Glen Ridge Rd, Fairfield, CT 06825
• 

  Est $1,381,568 Not Listed For Sale

  38 Hillspoint Rd, Westport, CT 06880

  • 4 Beds
  • 4 Baths
  • 2,112 Sq Ft
  • Built 1983

  38 Hillspoint Rd, Westport, CT 06880

  Last Sold Summary

  • 37% Above List Price
  • $476/SF
  • 135 Days On Market

  • Last Sold Price $1,005,000
  • Jan 19, 2024

  Last Listing Agent Todd Debek Debek Real Estate Services LLC
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  /17

  $249,999

  • 2 Beds
  • 2 Baths
  • 1,363 Sq Ft

  25 Cartright St Unit 7E, Bridgeport, CT 06604

  Stunning end unit 2-bedroom, 2-bath condo located in the desirable Brooklawn area of Bridgeport near the Fairfield line. This spacious 1,363 sq ft 7th-floor unit features wood flooring throughout and a bright, open-concept living and dining area. Enjoy treetop views from your private balcony. The unit offers an updated kitchen and bathrooms, a large primary suite with full bath, and generous

  Sasha Iyamu ERIS, LLC

  25 Cartright St Unit 7E, Bridgeport, CT 06604
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  /16

  $2,875 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,310 Sq Ft
  • Townhouse for Rent

  42 Ferris St, Bridgeport, CT 06605

  Terrific cul-de-sac location. Light, bright and spacious Duplex unit with views of Black Rock Harbor. Welcoming front porch. Open layout first floor with Kitchen and Family Room, Half Bath with new washer & dryer. Slider to rear deck and partially fenced back yard. The second floor features the primary bedroom with deck offering views of Black Rock Harbor and an additional nice size bedroom and

  Sandy Ruta Higgins Group Real Estate

  42 Ferris St, Bridgeport, CT 06605
• 

  $605,000 Sold Aug 15, 2025

  350 Grovers Ave Unit 11A, Bridgeport, CT 06605

  • 3 Beds
  • 1.5 Baths
  • 1,284 Sq Ft
  • Built 1975

  Last Sold Summary

  • 4% Above List Price
  • $471/SF
  • 10 Days On Market

  Current Estimated Value $609,689

  Last Listing Agent John Kleps Berkshire Hathaway NE Prop.

  350 Grovers Ave Unit 11A, Bridgeport, CT 06605
• 

  Est $2,261,756 Not Listed For Sale

  4 Country Rd, Westport, CT 06880

  • 4 Beds
  • 4 Baths
  • 3,912 Sq Ft
  • Built 1972

  4 Country Rd, Westport, CT 06880

  Last Sold Summary

  • 13% Above List Price
  • $512/SF
  • 13 Days On Market

  • Last Sold Price $2,003,500
  • Aug 30, 2024

  Last Listing Agent Heather Zito Carbutti & Co., Realtors
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  /3

  $1,699,000 New Construction

  • 4 Beds
  • 4 Baths
  • 3,700 Sq Ft

  217 Fairland Dr, Fairfield, CT 06825

  This stunning 3,700 square foot new construction Colonial features 4 spacious bedrooms and 4 full baths. The home is thoughtfully designed for today's lifestyle. The open-concept kitchen boasts a large quartz center island and flows seamlessly into the eating area and dramatic cathedral-ceiling family room. The primary suite is a true retreat, featuring cathedral ceilings, oversized walk-in

  Madeline O'Shea Coldwell Banker Realty

  217 Fairland Dr, Fairfield, CT 06825
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  /14

  $1,700 Per Month

  • 2 Beds
  • 1 Bath
  • 2,332 Sq Ft
  • Apartment for Rent

  7 Wilson St Unit 3, Bridgeport, CT 06605

  This well-maintained 3rd-floor apartment offers a comfortable and spacious layout featuring two generously sized bedrooms and ample living space. Finished in, great condition, the unit provides a clean, modern feel with plenty of natural light. Located in a desirable area, it offers convenience, accessibility, and a welcoming neighborhood atmosphere--making it an excellent rental option.

  Angel Mora eXp Realty

  7 Wilson St Unit 3, Bridgeport, CT 06605
• 

  $1,650,000 Sold Jul 02, 2025

  101 Mailands Rd, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 4,241 Sq Ft
  • Built 1998

  Last Sold Summary

  • 5% Above List Price
  • $389/SF
  • 22 Days On Market

  Current Estimated Value $1,710,126

  Last Listing Agent Eva Preuss William Raveis Real Estate

  101 Mailands Rd, Fairfield, CT 06824
• 

  Est $3,985,400 Not Listed For Sale

  146 North Ave, Westport, CT 06880

  • 6 Beds
  • 6.5 Baths
  • 7,400 Sq Ft
  • Built 2023

  146 North Ave, Westport, CT 06880

  Last Sold Summary

  • 12% Above List Price
  • $482/SF
  • 22 Days On Market

  • Last Sold Price $3,564,000
  • Jan 22, 2024

  Last Listing Agent Brett Lieberman The Riverside Realty Group
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  /20

  $2,800,000 New Construction

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

  53 Cross Hwy, Westport, CT 06880

  Proposed New Construction, build this beautiful home or let's design your dream home!! 1 acre lot with a brook sets up perfectly for a walk-out basement. Great location close to everything. Quality custom home builder with 25 years experience and over 150 homes built. Existing home to be torn down, taxes shown reflect existing home.

  Phil Pedros Philips Real Estate

  53 Cross Hwy, Westport, CT 06880
• 

  

  /15

  $8,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • House for Rent

  799 Rowland Rd, Fairfield, CT 06824

  Spend the month of August at a desirable Long Island Sound Location! Excellent condition property located directly across from sandy beach, 6 rooms, 3 bedrooms, 2 baths, all appliances and utilities included, lots of town amenities. Please note: this rental is available for the month of August 2026 only. Don't miss this opportunity to relax and enjoy the Summer!

  Barbara Whelan Coldwell Banker Realty

  799 Rowland Rd, Fairfield, CT 06824
• 

  $390,000 Sold Sep 08, 2025

  102 Hansen Ave Unit 104, Bridgeport, CT 06605

  • 6 Beds
  • 2 Baths
  • 2,511 Sq Ft
  • Built 1917

  Last Sold Summary

  • 5% Above List Price
  • $155/SF
  • 9 Days On Market

  Current Estimated Value $539,689

  Last Listing Agent John Armellino William Raveis Real Estate

  102 Hansen Ave Unit 104, Bridgeport, CT 06605
• 

  Est $4,892,249 Not Listed For Sale

  31 Soundview Dr, Westport, CT 06880

  • 4 Beds
  • 4 Baths
  • 2,821 Sq Ft
  • Built 1946

  31 Soundview Dr, Westport, CT 06880

  Last Sold Summary

  • 10% Above List Price
  • $1,580/SF
  • 127 Days On Market

  • Last Sold Price $4,456,250
  • Oct 02, 2023

  Last Listing Agent steven girden Compass Connecticut, LLC
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  /38

  $1,599,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 3.5 Baths
  • 3,012 Sq Ft

  71 Aberdeen Way Unit 71, Southport, CT 06890

  Beautiful End Unit, Perfectly situated in Southport, this beautifully appointed 3-bedroom, 3.5-bath Colonial townhouse end unit offers an exceptional lifestyle just moments from village shops, restaurants, Southport Harbor, and the Metro-North train. Thoughtfully updated, the remodeled kitchen features quartz countertops, a sleek backsplash, and premium Bosch appliances, centered around a

  Michael Ferraro Compass Connecticut, LLC

  71 Aberdeen Way Unit 71, Southport, CT 06890
• 

  

  /13

  $2,800 Per Month

  • 3 Beds
  • 1 Bath
  • 2,889 Sq Ft
  • House for Rent

  82-86 Waldorf Ave, Bridgeport, CT 06605

  Welcome to this beautifully renovated 3 bedroom apartment, where modern finishes meet unbeatable convenience. Enjoy a sleek kitchen with stainless steel appliances, the ease of laundry in unit, and a thoughtfully updated layout. Ideally located just minutes from I-95, grocery stores and popular dining options, everything you need is right at your doorstep. A perfect blend of comfort, style and

  Nadia Almezy Larracuente & Johnson Realty, LLC

  82-86 Waldorf Ave, Bridgeport, CT 06605
• 

  $1,800,000 Sold Aug 08, 2025

  91 Open Gate Ln, Southport, CT 06890

  • 5 Beds
  • 5.5 Baths
  • 4,709 Sq Ft
  • Built 1919

  Last Sold Summary

  • 6% Above List Price
  • $382/SF
  • 32 Days On Market

  Current Estimated Value $1,851,676

  Last Listing Agent Victoria Fingelly Higgins Group Real Estate

  91 Open Gate Ln, Southport, CT 06890
• 

  Est $2,820,545 Not Listed For Sale

  28 Spicer Rd, Westport, CT 06880

  • 5 Beds
  • 4.5 Baths
  • 5,437 Sq Ft
  • Built 2023

  28 Spicer Rd, Westport, CT 06880

  Last Sold Summary

  • 22% Above List Price
  • $425/SF
  • 59 Days On Market

  • Last Sold Price $2,310,000
  • Apr 01, 2024

  Last Listing Agent John Schiaroli Coldwell Banker Realty
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  /7

  $725,000

  • 5 Beds
  • 3 Baths
  • 2,483 Sq Ft

  855 Brewster St Unit 857, Bridgeport, CT 06605

  An incredible investment opportunity in a highly desirable Black Rock Neighborhood. This well maintained 3 Family property is perfect for investors or owner occupied. Ideally located within walking distance to the Fairfield Metro Train Station, shops and restaurants along Fairfield Ave. It's a short drive to I-95 and Downtown Fairfield and Black Rock Turnpike. This 3 Family home has 5 Bedrooms, 3

  Doug Munson Munson Real Estate

  855 Brewster St Unit 857, Bridgeport, CT 06605
• 

  

  /4

  $2,200 Per Month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Apartment for Rent

  206 Scofield Ave, Bridgeport, CT 06605

  Charming 2-bedroom, 1st floor Apartment in BlackRock, Connecticut. This Inviting apartment offers central air for your comfort and a dishwasher for easy cleanup. Nestled in the vibrant Blackrock Area, you're just steps away from shops, eateries, and parks. This apartment is perfect for those seeking a blend of convenience and comfort. Reach out today to schedule a viewing

  Lacie Malcolm Keller Williams Realty Prtnrs.

  206 Scofield Ave, Bridgeport, CT 06605
• 

  $6,650,000 Sold Jul 03, 2025

  51 Compo Beach Rd, Westport, CT 06880

  • 4 Beds
  • 3 Baths
  • 2,880 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $2,309/SF
  • 28 Days On Market

  Current Estimated Value $6,776,819

  Last Listing Agent Carol Cutler Higgins Group Bedford Square

  51 Compo Beach Rd, Westport, CT 06880
• 

  Est $1,818,078 Not Listed For Sale

  1 Pilgrim Trail, Westport, CT 06880

  • 4 Beds
  • 2.5 Baths
  • 3,844 Sq Ft
  • Built 1977

  1 Pilgrim Trail, Westport, CT 06880

  Last Sold Summary

  • 23% Above List Price
  • $384/SF
  • 38 Days On Market

  • Last Sold Price $1,476,000
  • Aug 28, 2023

  Last Listing Agent Regina Kendig William Raveis Real Estate

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