Southport, CT Homes

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  /22

  $3,995,000

  • 6 Beds
  • 7.5 Baths
  • 5,628 Sq Ft

  11 Clapboard Hill Rd, Westport, CT 06880

  An antique jewel set on 3.5 extraordinary acres in the heart of Greens Farms, ready to be transformed into your forever home. Brimming with timeless charm and endless potential, this rare offering showcases beautiful period details, including arched doorways, custom built-ins, and charming deep-set windows that reflect the home's historic character. The gracious main house is complemented by a

  Meredith Cohen Serhant Connecticut, LLC

  11 Clapboard Hill 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
• 

  $1,595,000 Sold Jun 23, 2025

  41 Richmondville Ave Unit 211, Westport, CT 06880

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $1,181/SF
  • 138 Days On Market

  Last Listing Agent Doug Bross Coldwell Banker Realty

  41 Richmondville Ave Unit 211, Westport, CT 06880
• 

  Not Listed For Sale

  18 Siacus Place, Fairfield, CT 06825

  • 5 Beds
  • 6 Baths
  • 4,100 Sq Ft
  • Built 2025

  18 Siacus Place, Fairfield, CT 06825

  Last Sold Summary

  • $476/SF
  • 100 Days On Market

  • Last Sold Price $1,950,000
  • May 02, 2025

  Last Listing Agent Basil Amso RE/MAX
• 

  

  

  /27

  $1,150,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  41 Richmondville Ave Unit 104, Westport, CT 06880

  The Mill Westport offers high-end luxury living with all the amenities of a fine custom home in the heart of downtown Westport. With a concierge on-site and approximately 10,000 square feet of spectacular interior and exterior amenity spaces such as The Great Room & Cafe, Pool, Health & Wellness Center, Patio & Rooftop Deck, residents will enjoy carefree, 5-star living. The 31 residences feature

  Doug Bross Coldwell Banker Realty

  41 Richmondville Ave Unit 104, Westport, CT 06880
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  /8

  $2,800

  Total Monthly Price

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

  292 Berkeley Rd Unit 292 BERKELEY RD, Fairfield, CT 06825

  This property is an amazing 2 bedroom 1 bathroom apartment with all new appliances and vinyl flooring. It is 900 square foot with plenty of room. Ideal for singles and couples. Furthermore, there is ALDI, Planet Fitness, Subway, Dunkin Donuts, and Stop & Shop within walking distance. This rental is available starting September 1, 2025.

  292 Berkeley Rd Unit 292 BERKELEY RD, Fairfield, CT 06825
• 

  $650,000 Sold Oct 31, 2025

  192 Scofield Ave, Bridgeport, CT 06605

  • 6 Beds
  • 2 Baths
  • 2,441 Sq Ft
  • Built 1923

  Last Sold Summary

  • 6% Below List Price
  • $266/SF
  • 56 Days On Market

  Current Estimated Value $677,036

  Last Listing Agent Marissa Papa Preston Gray Real Estate

  192 Scofield Ave, Bridgeport, CT 06605
• 

  Not Listed For Sale

  52 Deerfield St, Fairfield, CT 06825

  • 4 Beds
  • 3.5 Baths
  • 2,500 Sq Ft
  • Built 2025

  52 Deerfield St, Fairfield, CT 06825

  Last Sold Summary

  • $374/SF
  • 47 Days On Market

  • Last Sold Price $935,000
  • Apr 28, 2025

  Last Listing Agent John Shea William Raveis Real Estate
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  /40

  $1,980,000 Under Contract

  • 4 Beds
  • 3 Baths
  • 3,244 Sq Ft

  28 Turkey Hill Rd N, Westport, CT 06880

  Ideally located in the heart of Westport and close to all schools, this exceptional Contemporary Ranch has been thoughtfully renovated, offering one-level living with effortless sophistication. A welcoming foyer leads to a stunning kitchen, appointed with a generous center island, heated floors, premium appliances and an elegant coffee station with dedicated water supply. The kitchen opens

  Yulka Markevich Iron Gates Realty

  28 Turkey Hill Rd N, Westport, CT 06880
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  /30

  $12,850 Per Month

  • 5 Beds
  • 4 Baths
  • 2,882 Sq Ft
  • House for Rent

  18 Bridge St, Westport, CT 06880

  Historic just renovated Rufus Wakeman home is strategically located in Westport, CT on a beautiful, level, professionally landscaped, and private 0.82-acre lot. This cherished residence blends historic character with modern-day comfort. High ceilings and intricate moldings showcase the craftsmanship of a bygone era, while oversized windows flood the home with natural light. The inviting entryway

  Elizabeth Anrig Coach Lamp Living

  18 Bridge St, Westport, CT 06880
• 

  $2,700,000 Sold Oct 30, 2025

  2821 Congress St, Fairfield, CT 06824

  • 5 Beds
  • 4.5 Baths
  • 3,703 Sq Ft
  • Built 1835

  Last Sold Summary

  • 2% Above List Price
  • $729/SF
  • 42 Days On Market

  Last Listing Agent Andrew Whiteley Brown Harris Stevens

  2821 Congress St, Fairfield, CT 06824
• 

  Not Listed For Sale

  18 Fresenius Rd, Westport, CT 06880

  • 7 Beds
  • 8 Baths
  • 6,200 Sq Ft
  • Built 2024

  18 Fresenius Rd, Westport, CT 06880

  Last Sold Summary

  • $556/SF
  • 25 Days On Market

  • Last Sold Price $3,450,000
  • Apr 25, 2025

  Last Listing Agent Patricia Shea Coldwell Banker Realty
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  /27

  $535,000

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  12 Hulls Hwy Unit 12, Southport, CT 06890

  This first-floor, 2BR, 2-bath unit is in a quiet Southport complex with in-ground pool. Just a short walk to the grocery store, shopping, train, public bus line, bank, and more. The updated unit features a living room with vinyl plank flooring, ceiling fan, wood-burning fireplace with raised marble hearth, plus attractive millwork. Sliding glass doors open to a covered porch with lawn space for

  Sherri Steeneck Higgins Group Real Estate

  12 Hulls Hwy Unit 12, Southport, CT 06890
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  /26

  $2,575

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Condo for Rent

  79 2nd St Unit 2nd, Fairfield, CT 06825

  2 Bedroom, 1 Full Bathroom, 1 Kitchen, 1 Living Room, and 1 Dining Room, over 1000 SF on the 2nd floor with a front porch and back deckWith Washer and Dryer, Fridge, Stove, Microwave, Partial Cellar Storage and YardEnergy Efficient Hot Air Heating and Double Pane Windows Not far from a park with tennis courts, a baseball field, a soccer field, Fairfield Warde High School,

  79 2nd St Unit 2nd, Fairfield, CT 06825
• 

  $915,000 Sold Mar 27, 2026

  65 Thorpe St Unit 65, Fairfield, CT 06824

  • 3 Beds
  • 2.5 Baths
  • 2,303 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Above List Price
  • $397/SF
  • 63 Days On Market

  Current Estimated Value $876,080

  Last Listing Agent David Harmuth Coldwell Banker Realty

  65 Thorpe St Unit 65, Fairfield, CT 06824
• 

  Est $293,214 Not Listed For Sale

  2660 North Ave Unit 117, Bridgeport, CT 06604

  • 2 Beds
  • 2 Baths
  • 1,081 Sq Ft
  • Built 2010

  2660 North Ave Unit 117, Bridgeport, CT 06604

  Last Sold Summary

  • 7% Above List Price
  • $254/SF
  • 35 Days On Market

  • Last Sold Price $275,000
  • May 08, 2025

  Last Listing Agent Katie O'Grady Compass Connecticut, LLC
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  /25

  $672,000

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  245 Unquowa Rd Unit 44, Fairfield, CT 06824

  Welcome to Mosswood condominiums: A must see updated second floor residence in this Fairfield sought-after well maintained complex. Perfectly located within walking distance to train and area restaurants. Interior was just repainted. Beautifully updated, renovated kitchen and two full bathrooms. New window treatments and lighting. Impeccably maintained. Large rear deck overlooking courtyard.

  Ed Pinto The Pinto Group R. E. Services

  245 Unquowa Rd Unit 44, Fairfield, CT 06824
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  /16

  $4,900 Per Month

  • 4 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • House for Rent

  608 Stillson Rd, Fairfield, CT 06824

  Pristine Cape in Osborn Hill / University Area with Exceptional Backyard. This well-maintained home is ideally located and set on an amazing half acre lot. Surrounded by nature, this outdoor space offers peace, privacy, and ample room for entertaining, relaxing, and enjoying all your favorite summer activities. Inside, the home features a warm and inviting living room with hardwood floors, an eat

  Catherine Cardell Yarmosh Coldwell Banker Realty

  608 Stillson Rd, Fairfield, CT 06824
• 

  $1,905,000 Sold Jul 01, 2025

  15 Lone Pine Ln, Westport, CT 06880

  • 3 Beds
  • 2.5 Baths
  • 2,263 Sq Ft
  • Built 1953

  Last Sold Summary

  • 12% Above List Price
  • $842/SF
  • 11 Days On Market

  Current Estimated Value $1,960,411

  Last Listing Agent Mary Ellen Gallagher Compass Connecticut, LLC

  15 Lone Pine Ln, Westport, CT 06880
• 

  Est $432,966 Not Listed For Sale

  270 Melody Ln Unit 270, Fairfield, CT 06824

  • 1 Bed
  • 1 Bath
  • 1,557 Sq Ft
  • Built 1974

  270 Melody Ln Unit 270, Fairfield, CT 06824

  Last Sold Summary

  • 8% Above List Price
  • $258/SF
  • 72 Days On Market

  • Last Sold Price $401,000
  • Apr 29, 2025

  Last Listing Agent Nina Nyrop RE/MAX
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  /38

  $1,775,000 Open Sat 12PM - 3PM

  • 5 Beds
  • 6 Baths
  • 4,150 Sq Ft

  706 Judd St, Fairfield, CT 06824

  Opportunity knocks! Don't miss this fabulous NEW construction home in Fairfield's highly desirable University area, built by established local builders Coppola & Sons. This custom home set upon a perfect flat corner lot with beautiful patio and newly fully fenced yard offers 4,100 sqft+ of designer living space with an open-concept layout, encompassed by gorgeous Marvin windows providing abundant

  Melissa Montagno Higgins Group Real Estate

  706 Judd St, Fairfield, CT 06824
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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
• 

  $1,835,000 Sold Jul 18, 2025

  32 Middlebrook Dr, Fairfield, CT 06824

  • 6 Beds
  • 5.5 Baths
  • 5,109 Sq Ft
  • Built 2014

  Last Sold Summary

  • 2% Above List Price
  • $359/SF
  • 47 Days On Market

  Current Estimated Value $1,897,410

  Last Listing Agent Kate Cacciatore William Raveis Real Estate

  32 Middlebrook Dr, Fairfield, CT 06824
• 

  Est $944,200 Not Listed For Sale

  298 Pansy Rd, Fairfield, CT 06824

  • 5 Beds
  • 5 Baths
  • 2,271 Sq Ft
  • Built 2011

  298 Pansy Rd, Fairfield, CT 06824

  Last Sold Summary

  • 22% Above List Price
  • $341/SF
  • 189 Days On Market

  • Last Sold Price $775,000
  • Dec 10, 2024

  Last Listing Agent Catherine Cardell Yarmosh Coldwell Banker Realty
• 

  

  /35

  $2,100,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,231 Sq Ft

  677 Eleven O Clock Rd, Fairfield, CT 06824

  SELLER REQUESTS HIGHEST & BEST OFFERS BY 4PM MONDAY 3/16. Set on two private, park-like acres in one of Fairfield's most sought after neighborhoods, this beautifully updated home offers over 4,000 square feet of thoughtfully designed living space with 5 bedrooms and 4.5 baths, including a dedicated home office for today's flexible lifestyle and gunite pool. The heart of the home is a chef's

  Clyde Wauchope Coldwell Banker Realty

  677 Eleven O Clock Rd, Fairfield, CT 06824
• 

  

  /26

  $3,100 Per Month

  • 2 Beds
  • 2 Baths
  • 1,029 Sq Ft
  • Apartment for Rent

  245 Unquowa Rd Unit 46, Fairfield, CT 06824

  Light, bright and airy are the perfect words to describe this 2nd floor 2 bedroom, 2 bath condo. The ultra desirable Mosswood Complex is ideally located just steps from downtown Fairfield, the train station, the best eateries, shops, schools, library, beach, entertainment and theaters...making it the ultimate location! Hardwood floors guide you throughout the condo, which welcomes in tons of

  Dawn Gitman William Raveis Real Estate

  245 Unquowa Rd Unit 46, Fairfield, CT 06824
• 

  $1,650,000 Sold Sep 05, 2025

  550 Davis Rd, Fairfield, CT 06825

  • 5 Beds
  • 4.5 Baths
  • 3,927 Sq Ft
  • Built 2025

  Last Sold Summary

  • $420/SF
  • 50 Days On Market

  Current Estimated Value $1,676,797

  Last Listing Agent Carmen Desiato Serhant Connecticut, LLC

  550 Davis Rd, Fairfield, CT 06825
• 

  Est $1,827,773 Not Listed For Sale

  170 Windsor Rd, Fairfield, CT 06824

  • 5 Beds
  • 4.5 Baths
  • 4,975 Sq Ft
  • Built 2019

  170 Windsor Rd, Fairfield, CT 06824

  Last Sold Summary

  • 10% Above List Price
  • $335/SF
  • 13 Days On Market

  • Last Sold Price $1,665,000
  • Jun 27, 2024

  Last Listing Agent Julie Vanderblue Higgins Group Real Estate
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  /39

  $2,495,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 6,022 Sq Ft

  790 Cedar Brook Ln, Southport, CT 06890

  Set along a storybook private drive, where a gently winding brook passes beneath charming stone bridges, this is a home defined as much by its setting as by the way it lives. There's a quiet magic here-a sense of privacy and calm that feels rare, yet a warmth that makes it easy to imagine putting down roots and staying awhile. Inside, the home unfolds with an easy, natural flow. The spaces are

  Cindy Raney Coldwell Banker Realty

  790 Cedar Brook Ln, Southport, CT 06890
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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
• 

  $963,000 Sold Nov 07, 2025

  109 Green Acre Ln, Fairfield, CT 06824

  • 3 Beds
  • 3 Baths
  • 1,980 Sq Ft
  • Built 1959

  Last Sold Summary

  • 11% Above List Price
  • $486/SF
  • 9 Days On Market

  Current Estimated Value $968,250

  Last Listing Agent Lynn Dolan William Pitt Sotheby's Int'l

  109 Green Acre Ln, Fairfield, CT 06824
• 

  Not Listed For Sale

  318 Knapps Hwy Unit 318, Fairfield, CT 06825

  • 2 Beds
  • 1.5 Baths
  • 930 Sq Ft
  • Built 1973

  318 Knapps Hwy Unit 318, Fairfield, CT 06825

  Last Sold Summary

  • $414/SF
  • 46 Days On Market

  • Last Sold Price $385,000
  • Jul 02, 2024

  Last Listing Agent Mary Edeen Berkshire Hathaway Home Services
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  /40

  $2,099,000 Pending

  • 5 Beds
  • 4 Baths
  • 5,158 Sq Ft

  165 Hemlock Hills Rd S, Fairfield, CT 06824

  Enchanting countrystyle retreat offering the warmth of a welcoming neighborhood with the luxury of natural privacy, nestled amid professionally landscaped gardens and mature trees. Designed for gracious living and effortless entertaining, 165 Hemlock Hills S blends refined upgrades with modern comfort throughout. Featuring two primary suites, five bedrooms, and four beautifully renovated baths,

  Lois Lehman William Raveis Real Estate

  165 Hemlock Hills Rd S, Fairfield, CT 06824
• 

  

  /19

  $3,500 Per Month

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

  87 Southport Woods Dr, Southport, CT 06890

  This sun-filled and spacious first-floor residence offers two bedrooms and two full bathrooms. The updated kitchen opens to a private, inviting patio with tranquil views of mature trees and landscaped gardens. The primary suite features an en-suite bath and a walk-in closet. Additional highlights include an in-unit washer and dryer and a one-car garage. Set within the desirable Southport Woods

  Karen Cross William Raveis Real Estate

  87 Southport Woods Dr, Southport, CT 06890
• 

  $3,470,000 Sold Dec 02, 2025

  3 Bolton Ln, Westport, CT 06880

  • 6 Beds
  • 6.5 Baths
  • 7,899 Sq Ft
  • Built 2008

  Last Sold Summary

  • 9% Below List Price
  • $439/SF
  • 35 Days On Market

  Current Estimated Value $3,535,932

  Last Listing Agent Jen Kass Higgins Group Bedford Square

  3 Bolton Ln, Westport, CT 06880
• 

  Est $613,513 Not Listed For Sale

  1986 Kings Hwy, Fairfield, CT 06824

  • 4 Beds
  • 2 Baths
  • 1,668 Sq Ft
  • Built 1918

  1986 Kings Hwy, Fairfield, CT 06824

  Last Sold Summary

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

  • Last Sold Price $580,000
  • Jan 08, 2025

  Last Listing Agent Lani Liu-Helisch Sovereign Properties
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  /12

  $2,149,999 New Construction

  • 6 Beds
  • 5.5 Baths
  • 4,709 Sq Ft

  280 Tuckahoe Ln, Fairfield, CT 06824

  Exceptional new construction in the desirable University area, scheduled for completion in Fall 2026. Built by an experienced local builder known for quality craftsmanship and thoughtful design, this impressive home offers 4,709 square feet across four levels, including a walk-out lower level. Designed for modern living, the home features 6 bedrooms and 5.5 baths, providing flexibility for

  Elizabeth Casey William Raveis Real Estate

  280 Tuckahoe Ln, Fairfield, CT 06824
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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
• 

  $3,879,000 Sold Aug 15, 2025

  19 Center St, Westport, CT 06880

  • 6 Beds
  • 8 Baths
  • 7,861 Sq Ft
  • Built 2017

  Last Sold Summary

  • $493/SF
  • 18 Days On Market

  Current Estimated Value $3,967,546

  Last Listing Agent Brett Lieberman The Riverside Realty Group

  19 Center St, Westport, CT 06880
• 

  Est $783,240 Not Listed For Sale

  64 Sterling St, Fairfield, CT 06825

  • 3 Beds
  • 2.5 Baths
  • 2,197 Sq Ft
  • Built 2017

  64 Sterling St, Fairfield, CT 06825

  Last Sold Summary

  • 3% Above List Price
  • $346/SF
  • 55 Days On Market

  • Last Sold Price $760,000
  • Aug 07, 2024

  Last Listing Agent Michael Jabick Keller Williams Realty

Showing Results 161 - 200, Page 5 of 18