Southport, CT Homes

• 

  

  

  /29

  $599,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 920 Sq Ft

  9 Crescent Park Rd, Westport, CT 06880

  Welcome to this charming 3-bedroom, 1.5-bath ranch in the heart of Westport - the perfect blend of comfort, convenience, and low-maintenance living. With a brand-new roof and vinyl siding, this home is ready for years of worry-free enjoyment. The inviting living room features a cozy fireplace, creating a warm and welcoming space to relax or entertain. Thoughtfully designed for one-level living,

  Karim Douich William Raveis Real Estate

  9 Crescent Park Rd, Westport, CT 06880
• 

  

  

  /21

  $1,895 Per Month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  2806 Fairfield Ave Unit 103, Bridgeport, CT 06605

  The Newly Renovated Wanis Building! Spectacular first floor, one bedroom, one bathroom end unit available for immediate occupancy! The unit has been freshly painted and cleaned and offers an open living, dining, kitchen area, the appliances are stainless steel and there is also a stackable washer and dryer. This nice and bright end unit with exposed brick is ideally located in the Black Rock

  John Kleps Berkshire Hathaway NE Prop.

  2806 Fairfield Ave Unit 103, Bridgeport, CT 06605
• 

  $635,000 Sold Sep 25, 2025

  125 Vesper St, Fairfield, CT 06825

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • Built 1919

  Last Sold Summary

  • 2% Above List Price
  • $335/SF
  • 21 Days On Market

  Current Estimated Value $650,355

  Last Listing Agent Max Dober Keller Williams Prestige Prop.

  125 Vesper St, Fairfield, CT 06825
• 

  Est $1,737,918 Not Listed For Sale

  76 Terra Nova Cir, Westport, CT 06880

  • 3 Beds
  • 2.5 Baths
  • 2,358 Sq Ft
  • Built 2004

  76 Terra Nova Cir, Westport, CT 06880

  Last Sold Summary

  • 9% Above List Price
  • $679/SF
  • 36 Days On Market

  • Last Sold Price $1,600,000
  • Sep 09, 2024

  Last Listing Agent Alex Chingas Coldwell Banker Realty
• 

  

  

  /33

  $2,495,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,760 Sq Ft

  41 Richmondville Ave Unit Duplex 2, Westport, CT 06880

  IMMEDIATE OCCUPANCY! The FInal opportunity to own at The Mill Westport! This impressive home has floor-to-ceiling windows, wood floors and a linear gas fireplace. The kitchen has an oversized island, high-end appliances, and is complete with custom cabinetry. The 2 bedrooms are on opposites sides of the home for maximum privacy. The primary suite has a generous walk-in closet and a luxurious

  Ashlei De Souza Serhant LLC

  41 Richmondville Ave Unit Duplex 2, Westport, CT 06880
• 

  

  /38

  $15,000 Per Month

  • 4 Beds
  • 4 Baths
  • 2,473 Sq Ft
  • House for Rent

  11 Guyer Rd, Westport, CT 06880

  Nestled in the coveted Greens Farms neighborhood, this impeccably updated residence offers a refined rental experience with every detail considered. The chef's kitchen commands attention with a dramatic waterfall island and premium appliances, seamlessly transitioning from intimate dinners to sophisticated entertaining. Retreat to the generous primary suite, where a spa caliber bath, complete

  Demetrios Dassouras Coldwell Banker Realty

  11 Guyer Rd, Westport, CT 06880
• 

  $1,000,000 Sold Dec 15, 2025

  2492 Congress St, Fairfield, CT 06824

  • 4 Beds
  • 3 Baths
  • 2,273 Sq Ft
  • Built 1929

  Last Sold Summary

  • 16% Above List Price
  • $440/SF
  • 47 Days On Market

  Current Estimated Value $976,514

  Last Listing Agent Tracie and Vicki Team William Raveis Real Estate

  2492 Congress St, Fairfield, CT 06824
• 

  Est $3,927,826 Not Listed For Sale

  4 Michele Ln, Westport, CT 06880

  • 5 Beds
  • 8 Baths
  • 9,240 Sq Ft
  • Built 2005

  4 Michele Ln, Westport, CT 06880

  Last Sold Summary

  • 7% Above List Price
  • $396/SF
  • 63 Days On Market

  • Last Sold Price $3,655,000
  • Jan 21, 2025

  Last Listing Agent Mary Ann Lindwall The Riverside Realty Group
• 

  

  /12

  $630,000 Pending

  • 9 Beds
  • 3 Baths
  • 3,047 Sq Ft

  203 Lenox Ave Unit 205, Bridgeport, CT 06605

  Three family mainly occupied as the third floor was recently renovated. Owners are ready to pass the baton to the next owner. Take a look and present your best offer. AS IS SALE.

  Ruth-Ann Mitchell Larracuente & Johnson Realty, LLC

  203 Lenox Ave Unit 205, Bridgeport, CT 06605
• 

  

  /29

  $4,200 Per Month

  • 3 Beds
  • 3 Baths
  • 1,109 Sq Ft
  • House for Rent

  709 Tunxis Hill Rd, Fairfield, CT 06825

  Welcome to 709 Tunxis Hill Road! Experience refined rental living in this beautifully updated three-bedroom single-family home, offering exceptional charm, abundant natural light, and thoughtfully designed living spaces throughout. This property showcases an expansive, private backyard and large patio/deck for entertaining or relaxation that seamlessly extends your living space into the outdoors.

  Jocelyn Baum Coldwell Banker Realty

  709 Tunxis Hill Rd, Fairfield, CT 06825
• 

  $1,900,000 Sold Aug 11, 2025

  1369 S Pine Creek Rd, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 2,521 Sq Ft
  • Built 2025

  Last Sold Summary

  • $754/SF
  • 141 Days On Market

  Current Estimated Value $1,849,715

  Last Listing Agent Veronica Monahan Compass Connecticut, LLC

  1369 S Pine Creek Rd, Fairfield, CT 06824
• 

  Est $3,298,998 Not Listed For Sale

  38 Whitney St, Westport, CT 06880

  • 6 Beds
  • 7.5 Baths
  • 5,417 Sq Ft
  • Built 2004

  38 Whitney St, Westport, CT 06880

  Last Sold Summary

  • 18% Above List Price
  • $518/SF
  • 54 Days On Market

  • Last Sold Price $2,805,000
  • Nov 30, 2023

  Last Listing Agent Michelle Genovesi William Raveis Real Estate
• 

  

  /40

  $4,300,000

  • 6 Beds
  • 7 Baths
  • 7,170 Sq Ft

  129 Quarter Horse Ln, Fairfield, CT 06824

  Tucked away on a quiet cul-de-sac in the heart of Greenfield Hill,this exceptional 7,100-sqft estate is set on two meticulously landscaped acres,offering a rare blend of timeless elegance & modern luxury.A sweeping two-tiered bluestone terrace frames the stunning 20'x40' heated gunite pool,creating a private outdoor sanctuary designed for both relaxation & grand-scale entertaining.Completely

  Julie Vanderblue Higgins Group Real Estate

  129 Quarter Horse Ln, Fairfield, CT 06824
• 

  

  /30

  $3,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft
  • House for Rent

  234 N Pine Creek Rd, Fairfield, CT 06824

  Looking for a convenient location? Look no further. This well maintained home is close to town, train, shopping and restaurants. Interior includes a fabulous kitchen with breakfast bar & granite counter tops, dining room with wet bar, living room with fireplace, sun room, mud room and half bath complete the main floor. Upper level has 3 bedrooms and 2 full bathrooms. Primary bedroom features

  Gail Williams Coldwell Banker Realty

  234 N Pine Creek Rd, Fairfield, CT 06824
• 

  $185,000 Sold Dec 26, 2025

  26 Rowsley St Unit 3, Bridgeport, CT 06605

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Built 1918

  Last Sold Summary

  • $218/SF
  • 113 Days On Market

  Last Listing Agent Jennifer Wilson Berkshire Hathaway NE Prop.

  26 Rowsley St Unit 3, Bridgeport, CT 06605
• 

  Est $2,505,846 Not Listed For Sale

  14 Sandy Hill Terrace, Westport, CT 06880

  • 5 Beds
  • 4.5 Baths
  • 5,084 Sq Ft
  • Built 2002

  14 Sandy Hill Terrace, Westport, CT 06880

  Last Sold Summary

  • 6% Above List Price
  • $464/SF
  • 12 Days On Market

  • Last Sold Price $2,360,000
  • Oct 30, 2024

  Last Listing Agent Kathleen O'Connell Coldwell Banker Realty
• 

  

  /25

  $675,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,984 Sq Ft

  329 Bronson Rd, Southport, CT 06890

  Reduced!! Location, location and Location! Here is a chance to build some sweet equity that you have been waiting for! With 4 Bedrooms and 3 full bathrooms there is room for all. Living room with a fireplace along with two additional sitting room to accommodate all your guests. Partially fenced in yard, detached garage. Central air, gas heat, tankless hot water heater , 2 car detached garage,

  Masooma Ali Connecticut Choice Realty

  329 Bronson Rd, Southport, CT 06890
• 

  

  /12

  $2,500 Per Month

  • 2 Beds
  • 1 Bath
  • 3,350 Sq Ft
  • House for Rent

  2449-2451 North Ave Unit 1, Bridgeport, CT 06604

  Spacious and light-filled 2-bedroom rental located in a well-maintained multi-family home. This large unit features high ceilings that create an open, airy feel throughout. Enjoy comfortable living in a convenient location close to shopping, dining, and everyday amenities. A great opportunity for those seeking space, charm, and easy access to everything you need.

  Bobbie Poeltl Abagnale William Pitt Sotheby's Int'l

  2449-2451 North Ave Unit 1, Bridgeport, CT 06604
• 

  $2,645,000 Sold Feb 17, 2026

  11 Old Hill Rd, Westport, CT 06880

  • 4 Beds
  • 4.5 Baths
  • 3,935 Sq Ft
  • Built 1928

  Last Sold Summary

  • 5% Above List Price
  • $672/SF
  • 16 Days On Market

  Current Estimated Value $2,581,938

  Last Listing Agent Susan Lieberman The Riverside Realty Group

  11 Old Hill Rd, Westport, CT 06880
• 

  Est $3,678,158 Not Listed For Sale

  10 Tranquility Ln, Westport, CT 06880

  • 5 Beds
  • 6 Baths
  • 5,643 Sq Ft
  • Built 1999

  10 Tranquility Ln, Westport, CT 06880

  Last Sold Summary

  • 20% Above List Price
  • $541/SF
  • 6 Days On Market

  • Last Sold Price $3,055,000
  • Aug 25, 2023

  Last Listing Agent Krista Alecia Coldwell Banker Realty
• 

  

  /39

  $2,700,000

  • 5 Beds
  • 4.5 Baths
  • 4,179 Sq Ft

  114 Cross Hwy, Westport, CT 06880

  Welcome to a one-of-a-kind home in the heart of Westport - where timeless Colonial charm meets the elegance of a Parisian Estate. Set on an acre+ this home offers sophistication, space, and serenity throughout. The light-filled LR stuns with vaulted ceilings, HW floors, a wood-burning fireplace, and French doors opening directly to the deck and pool - the perfect setting for everyday living or

  Robert Appell Coldwell Banker Realty

  114 Cross Hwy, Westport, CT 06880
• 

  

  /40

  $4,500 Per Month

  • 2 Beds
  • 1.5 Baths
  • 830 Sq Ft
  • Apartment for Rent

  201 Main St Unit 203, Westport, CT 06880

  Welcome to Belden Place! Casual Luxury living personified in this boutique complex offering exquisite in-town living. This secure building with elevator access on the Saugatuck River is pet friendly. These luxury apartments are perfectly appointed and designed: plenty of closet space and storage, custom cabinetry, high-end appliances, in-unit washer and dryer, and private balconies. Enjoy the

  Mar Jennings Higgins Group Bedford Square

  201 Main St Unit 203, Westport, CT 06880
• 

  $1,450,000 Sold Sep 12, 2025

  60 Walbin Ct, Fairfield, CT 06824

  • 4 Beds
  • 3.5 Baths
  • 3,497 Sq Ft
  • Built 1997

  Last Sold Summary

  • $415/SF
  • 33 Days On Market

  Current Estimated Value $1,524,823

  Last Listing Agent Chrissie Rodriguez Higgins Group Real Estate

  60 Walbin Ct, Fairfield, CT 06824
• 

  Est $3,557,745 Not Listed For Sale

  8 Tranquility Ln, Westport, CT 06880

  • 4 Beds
  • 5 Baths
  • 6,225 Sq Ft
  • Built 1999

  8 Tranquility Ln, Westport, CT 06880

  Last Sold Summary

  • 24% Above List Price
  • $462/SF
  • 129 Days On Market

  • Last Sold Price $2,875,000
  • May 12, 2023

  Last Listing Agent Michelle Genovesi William Raveis Real Estate
• 

  

  /35

  $1,590,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 2,993 Sq Ft

  99 Acorn Ln, Southport, CT 06890

  Welcome to 99 Acorn Lane, a desirable Southport address set on a quiet cul-de-sac just minutes to Westport, Southport Village, and Downtown Fairfield. This expanded Cape sits on 1.24 beautiful acres, offering privacy within a charming neighborhood and ample opportunity for expansion or a pool, subject to approvals. Thoughtfully upgraded, the home offers more than 3,000 square feet of flexible

  Tara Hawley Coldwell Banker Realty

  99 Acorn Ln, Southport, CT 06890
• 

  

  /18

  $2,600 Per Month

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

  40 Beacon View Dr Unit 2, Fairfield, CT 06825

  Beautifully renovated and ready for you to make it a home. Kitchen has new stainless appliances, including range, refrigerator and dishwasher. White cabinets and gorgeous quartz counter tops are both complimented by the subway tile backsplash. You wont be able to wait to cook your first meal! The spacious living/dining area has a lot of natural light and is open to the kitchen. Two good size

  Silva Christov Keller Williams Prestige Prop.

  40 Beacon View Dr Unit 2, Fairfield, CT 06825
• 

  $899,000 Sold Nov 10, 2025

  153 Longview Ave, Fairfield, CT 06824

  • 4 Beds
  • 3 Baths
  • 2,912 Sq Ft
  • Built 1920

  Last Sold Summary

  • $309/SF
  • 48 Days On Market

  Current Estimated Value $914,138

  Last Listing Agent Christine Ricci Keller Williams NY Realty

  153 Longview Ave, Fairfield, CT 06824
• 

  Est $1,887,613 Not Listed For Sale

  44 Bridge St, Westport, CT 06880

  • 4 Beds
  • 3.5 Baths
  • 4,549 Sq Ft
  • Built 1999

  44 Bridge St, Westport, CT 06880

  Last Sold Summary

  • 37% Above List Price
  • $303/SF
  • 37 Days On Market

  • Last Sold Price $1,380,000
  • Sep 01, 2023

  Last Listing Agent Adrienne Durkin Compass Connecticut, LLC
• 

  

  /16

  $169,000

  • 1 Bed
  • 1 Bath
  • 604 Sq Ft

  2370 North Ave Unit 4C, Bridgeport, CT 06604

  Welcome to The Regency, where comfort, simplicity, and convenience come together in Bridgeport's desirable Brooklawn neighborhood. This bright and well-maintained one-bedroom condo offers an easy, low-maintenance lifestyle with a layout that feels open and inviting from the moment you step inside. Natural light fills the spacious living and dining area, complemented by hardwood floors and a

  Shane Mason-Fryer KW Legacy Partners

  2370 North Ave Unit 4C, Bridgeport, CT 06604
• 

  

  /12

  $2,500 Per Month

  • 3 Beds
  • 1 Bath
  • 1,068 Sq Ft
  • House for Rent

  898 Hancock Ave Unit 3, Bridgeport, CT 06605

  Beautifully renovated 3rd-floor apartment offering a bright, airy layout with modern finishes throughout. This move-in-ready unit features updated flooring, a refreshed kitchen, and a clean, contemporary bathroom. The spacious primary bedroom stands out with a versatile walk-in closet or bonus sitting area-perfect for a home office, dressing space, or cozy retreat. Located on the top floor, the

  Vanessa Cabrera US Asset Realty

  898 Hancock Ave Unit 3, Bridgeport, CT 06605
• 

  $1,210,000 Sold Oct 15, 2025

  14 Dill Rd, Fairfield, CT 06824

  • 3 Beds
  • 2.5 Baths
  • 2,659 Sq Ft
  • Built 1947

  Last Sold Summary

  • 3% Above List Price
  • $455/SF
  • 23 Days On Market

  Current Estimated Value $1,220,858

  Last Listing Agent Carrie Sakey Coldwell Banker Realty

  14 Dill Rd, Fairfield, CT 06824
• 

  Est $3,681,954 Not Listed For Sale

  19 Woody Ln, Westport, CT 06880

  • 6 Beds
  • 9 Baths
  • 8,928 Sq Ft
  • Built 1997

  19 Woody Ln, Westport, CT 06880

  Last Sold Summary

  • 19% Above List Price
  • $347/SF
  • 36 Days On Market

  • Last Sold Price $3,100,000
  • Apr 23, 2024

  Last Listing Agent Linda Skolnick Coldwell Banker Realty
• 

  

  /40

  $3,395,000 Pending

  • 5 Beds
  • 6 Baths
  • 8,192 Sq Ft

  91 Turkey Hill Rd S, Westport, CT 06880

  Beautifully sited in prestigious Greens Farms this timeless 5 BR, 6BA clapboard-and-stone Colonial offers stunning architecture & resort like privacy just moments from train, town & beaches. A gracious front porch & exquisite landscaping create an immediate sense of presence; classic, composed & quietly impressive. Inside, a soaring entry filled w/natural light introduces interiors defined by

  Kate Cacciatore William Raveis Real Estate

  91 Turkey Hill Rd S, Westport, CT 06880
• 

  

  /21

  $2,800 Per Month

  • 3 Beds
  • 1 Bath
  • 1,309 Sq Ft
  • House for Rent

  557 Colorado Ave Unit Second Floor, Bridgeport, CT 06605

  **UTILITIES INCLUDED** Step into this recently updated 3-bedroom, 1-bathroom second-floor unit in the vibrant West End of Bridgeport! Enjoy modern living with stylish finishes throughout, including a bright kitchen with sleek granite countertops and contemporary appliances. Each bedroom offers a comfortable retreat, while the refreshed bathroom boasts elegant fixtures. In-Unit laundry a huge

  Donjae Sampson YellowBrick Real Estate LLC

  557 Colorado Ave Unit Second Floor, Bridgeport, CT 06605
• 

  $1,600,000 Sold Mar 02, 2026

  105 Charter Oak Rd, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 3,900 Sq Ft
  • Built 1975

  Last Sold Summary

  • 7% Above List Price
  • $410/SF
  • 138 Days On Market

  Current Estimated Value $1,511,985

  Last Listing Agent Julie Vanderblue Higgins Group Real Estate

  105 Charter Oak Rd, Fairfield, CT 06824
• 

  Est $581,359 Not Listed For Sale

  14 Cross Hwy Unit B, Westport, CT 06880

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Built 1900

  14 Cross Hwy Unit B, Westport, CT 06880

  Last Sold Summary

  • 9% Above List Price
  • $669/SF
  • 40 Days On Market

  • Last Sold Price $535,000
  • May 07, 2024

  Last Listing Agent Sandra Calise Cenatiempo Settlers & Traders
• 

  

  /40

  $3,200,000 Open Sat 12PM - 2PM

  • 5 Beds
  • 5.5 Baths
  • 7,048 Sq Ft

  123 Cross Hwy, Westport, CT 06880

  A sophisticated blend of past & present, this private sanctuary offers the ultimate in modern design in the heart of Westport. Designed for effortless indoor-outdoor living, the property features 5 BRs, 4.5 BAs, a separate guest house, expansive decking & a gunite pool set on private 1.35 acres. The home retains its massive original central chimney now the striking centerpiece of the open main

  Patricia Shea Coldwell Banker Realty

  123 Cross Hwy, Westport, CT 06880
• 

  

  /38

  $4,500 Per Month

  • 1 Bed
  • 1 Bath
  • 935 Sq Ft
  • House for Rent

  205 Hillspoint Rd Unit 2nd Floor, Westport, CT 06880

  Wake up to sunlight dancing across the water and end your day wrapped in the calm of coastal living. Nestled within Westport's coveted Hillspoint/Compo Beach enclave, this 1-bedroom, second-floor apartment offers direct waterfront living on the serene pond preserve - a peaceful retreat where every moment feels like a getaway. Expansive walls of windows flood the almost 950 sq ft interior with

  Jessica Christ Coldwell Banker Realty

  205 Hillspoint Rd Unit 2nd Floor, Westport, CT 06880
• 

  $3,250,000 Sold Jun 06, 2025

  27 Old Hill Farms Rd, Westport, CT 06880

  • 5 Beds
  • 3.5 Baths
  • 4,298 Sq Ft
  • Built 1931

  Last Sold Summary

  • 8% Above List Price
  • $756/SF
  • 8 Days On Market

  Current Estimated Value $3,348,551

  Last Listing Agent Debra Grant Show to Sell Homes, LLC

  27 Old Hill Farms Rd, Westport, CT 06880
• 

  Est $769,761 Not Listed For Sale

  12 Cross Hwy Unit C, Westport, CT 06880

  • 2 Beds
  • 1 Bath
  • 1,074 Sq Ft
  • Built 1900

  12 Cross Hwy Unit C, Westport, CT 06880

  Last Sold Summary

  • 29% Above List Price
  • $554/SF
  • 45 Days On Market

  • Last Sold Price $595,000
  • Feb 20, 2024

  Last Listing Agent Doug Rose Scalzo Real Estate

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