35,315

Southport, CT Homes

Section Image
  • /31

    $1,795,000

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,884 Sq Ft

    5 Drumlin Rd, Westport, CT 06880

    Offers due by 5PM Monday, 7/27. Tucked into one of Westport's most treasured beach neighborhoods, this sun-filled Colonial is where people ride bikes until dinner, neighbors become lifelong friends, and an evening walk to Compo Beach can become part of your daily routine. From the moment you step inside, soaring ceilings, natural light, and beautifully connected living spaces create a home that

    Cindy Raney Coldwell Banker Realty

    5 Drumlin Rd, Westport, CT 06880
  • /12

    $3,250 Per Month

    • 2 Beds
    • 1 Bath
    • 1,075 Sq Ft
    • House for Rent

    1903 Post Rd Unit 1917, Fairfield, CT 06824

    Modern Second floor 2 bedroom / 1 bathroom apartment in the heart of Downtown Fairfield-CT with in unit laundry. Walking distance to Manhattan train, Fairfield University campus, Fairfield beaches, and all shopping. Have your own reserved parking, and enjoy the lifestyle of Fairfield. Tenant responsible for electric & Internet. 2 Months security deposit required.

    Amru Abo-Alaial RE/MAX One

    1903 Post Rd Unit 1917, Fairfield, CT 06824
  • 329 Bronson Rd, Southport, CT 06890

    $613,300

    Sold Jul 13, 2026

    329 Bronson Rd, Southport, CT 06890

    • 4 Beds
    • 3 Baths
    • 1,984 Sq Ft
    • Built 1946

    Last Sold Summary

    • 18% Below List Price
    • $309/SF
    • 8 Days On Market

    Current Estimated Value $670,375

    Last Listing Agent Masooma Ali Connecticut Choice Realty

    329 Bronson Rd, Southport, CT 06890
    • 232 Bayberry Ln, Westport, CT 06880

      Est $3,568,586

      Not Listed For Sale

      232 Bayberry Ln, Westport, CT 06880

      • 5 Beds
      • 4.5 Baths
      • 5,432 Sq Ft
      • Built 2021
      232 Bayberry Ln, Westport, CT 06880

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Cyd Hamer William Pitt Sotheby's Int'l

  • /39

    $5,499,000

    Pending
    • 4 Beds
    • 6 Baths
    • 3,855 Sq Ft

    1657 Fairfield Beach Rd, Fairfield, CT 06824

    Exceptional, one of a kind property, with direct beach frontage, panoramic views, inground pool, elevator, and a magnificent 2-story elliptical staircase to resemble a seashell. Best of all this home is better than new & FEMA compliant. The elevator extends from the garage to 3 floors more. The residence has 7 outdoor decks to enjoy breathtaking sunrises, sunsets, LI ferry and Penfield

    Joanne Landino Berkshire Hathaway NE Prop.

    1657 Fairfield Beach Rd, Fairfield, CT 06824
  • /31

    $2,500 Per Month

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

    324 Villa Ave, Fairfield, CT 06825

    All utilities are included-electricity, central air, gas, heat, hot water and Internet. Enjoy the comfort and privacy of a single-family home at a one-bedroom condo budget. This beautifully maintained and updated home offers a spacious layout with one bedroom and one full bath, plus additional usable living and storage space beyond the recorded square footage. The updated, oversized kitchen is

    Gloria Shao Keller Williams Prestige Prop.

    324 Villa Ave, Fairfield, CT 06825
  • 709 Tunxis Hill Rd, Fairfield, CT 06825

    $540,000

    Sold Dec 18, 2025

    709 Tunxis Hill Rd, Fairfield, CT 06825

    • 3 Beds
    • 1.5 Baths
    • 1,409 Sq Ft
    • Built 1919

    Last Sold Summary

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

    Current Estimated Value $560,503

    Last Listing Agent Joseph Muratori Coldwell Banker Realty

    709 Tunxis Hill Rd, Fairfield, CT 06825
    • 21 Sturges Commons, Westport, CT 06880

      Est $3,087,847

      Not Listed For Sale

      21 Sturges Commons, Westport, CT 06880

      • 4 Beds
      • 3.5 Baths
      • 3,158 Sq Ft
      • Built 1949
      21 Sturges Commons, Westport, CT 06880

      Last Sold Summary

      • 63 Days On Market

      Last Listing Agent Patricia Shea Coldwell Banker Realty

  • /22

    $3,995,000

    $305K PRICE DROP Pending
    • 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
  • /16

    $1,850 Per Month

    • 4 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    81 Longfellow Ave Unit 2nd flr, Fairfield, CT 06825

    This inviting 2nd-floor ranch unit boasts a bright and airy open floor plan, featuring four bedrooms, a single bathroom, and a well-appointed eat-in kitchen with a pantry and white cabinetry. The interior is painted in a trendy gray lending a modern touch to the space. The unit is equipped with gas heating, and it benefits from public water and sewer. Ample off-street parking is available in the

    Joan Hainsworth Berkshire Hathaway NE Prop.

    81 Longfellow Ave Unit 2nd flr, Fairfield, CT 06825
  • 84-86 Dewey St, Bridgeport, CT 06605

    $415,000

    Sold Sep 17, 2025

    84-86 Dewey St, Bridgeport, CT 06605

    • 4 Beds
    • 2 Baths
    • 1,628 Sq Ft
    • Built 1918

    Last Sold Summary

    • 3% Below List Price
    • $255/SF
    • 103 Days On Market

    Last Listing Agent Robert Ganim RE/MAX Heritage

    84-86 Dewey St, Bridgeport, CT 06605
    • 298 Pansy Rd, Fairfield, CT 06824

      Est $1,109,843

      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

      • 189 Days On Market

      Last Listing Agent Catherine Cardell Yarmosh Coldwell Banker Realty

  • /40

    $12,000,000

    • 7 Beds
    • 10 Baths
    • 9,129 Sq Ft

    4800 Congress St, Fairfield, CT 06824

    This offering is for 4800 Congress St, a one of a kind estate consists of main residence on 10.92 acres, pool, barn pool house/gym, heated paddle court, and an office pavilion. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street,offering seclusion with proximity to NYC. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century

    Leslie Razook William Pitt Sotheby's Int'l

    4800 Congress St, Fairfield, CT 06824
  • /23

    $6,000 Per Month

    • 4 Beds
    • 1 Bath
    • 1,267 Sq Ft
    • House for Rent

    27 Reef Ct, Fairfield, CT 06824

    Welcome to this newly refreshed coastal home, ideally situated in the desirable Fairfield Beach area. Bright, spacious, and filled with natural light, this 4-bedroom, 1-bath gem offers the perfect blend of comfort and convenience. Just a short walk to Penfield Beach and the Post Road, the location is unbeatable-enjoy beachside living while staying close to great restaurants, shops, and local

    Carla Foote William Raveis Real Estate

    27 Reef Ct, Fairfield, CT 06824
  • 259 Wilton Rd, Westport, CT 06880

    $1,475,000

    Sold Dec 19, 2025

    259 Wilton Rd, Westport, CT 06880

    • 5 Beds
    • 4.5 Baths
    • 3,589 Sq Ft
    • Built 1940

    Last Sold Summary

    • $411/SF
    • 23 Days On Market

    Current Estimated Value $1,429,506

    Last Listing Agent Inna Agujen Coldwell Banker Realty

    259 Wilton Rd, Westport, CT 06880
    • 170 Windsor Rd, Fairfield, CT 06824

      Est $1,979,081

      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

      • 13 Days On Market

      Last Listing Agent Julie Vanderblue Higgins Group Real Estate

  • /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
  • /29

    $7,950 Per Month

    • 2 Beds
    • 2 Baths
    • 2,720 Sq Ft
    • House for Rent

    51 Maple Ave S, Westport, CT 06880

    Experience the best of Westport living in this beautifully FULLY FURNISHED contemporary retreat, ideally located near Green's Farms Train Station and Burying Hill Beach, and everything the area has to offer. Bathed in natural light, the open, airy floor plan features soaring ceilings, a gourmet eat-in kitchen with professional appliances, and inviting living spaces that flow effortlessly to the

    Elizabeth Steffen Higgins Group Bedford Square

    51 Maple Ave S, Westport, CT 06880
  • 1846 Mill Plain Rd, Fairfield, CT 06824

    $1,699,000

    Sold Aug 20, 2025

    1846 Mill Plain Rd, Fairfield, CT 06824

    • 5 Beds
    • 4 Baths
    • 4,250 Sq Ft
    • Built 2025

    Last Sold Summary

    • $400/SF
    • 28 Days On Market

    Current Estimated Value $1,597,686

    Last Listing Agent Jacob Bivona Keller Williams Prestige Prop.

    1846 Mill Plain Rd, Fairfield, CT 06824
    • 318 Knapps Hwy Unit 318, Fairfield, CT 06825

      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

      • 46 Days On Market

      Last Listing Agent Mary Edeen Berkshire Hathaway NE Prop.

  • /19

    $10,500,000

    • 4 Beds
    • 5.5 Baths
    • 10,522 Sq Ft

    47 Charcoal Hill Rd, Westport, CT 06880

    Designed by renowned architect and builder Frazier Forman Peters, this stone estate is set on nearly 3.5 private, meticulously landscaped acres in Westport. Crafted over more than two decades, the residence reflects exceptional artistry, scale, and craftsmanship. A gated entry and winding stone drive arrive at a stately porte-cochere and attached two-car garage, establishing a grand sense of

    Jonathan Ducharme Serhant Connecticut, LLC

    47 Charcoal Hill Rd, Westport, CT 06880
  • /23

    $2,100 Per Month

    • 2 Beds
    • 1 Bath
    • 742 Sq Ft
    • Apartment for Rent

    124 Thorpe St, Fairfield, CT 06824

    This rental offers comfort and convenience, located in town with easy access to everything you need. The second-floor unit features 2 bedrooms, 1 full bathroom, and a small bonus room off the living room that can serve as an office, extra closet space, or however you see fit. Kitchen has recently been updated with new granite countertops. New vinyl flooring in living room and the 2 bedrooms.

    Denise Napoleone William Raveis Real Estate

    124 Thorpe St, Fairfield, CT 06824
  • 15 Wright St, Westport, CT 06880

    $1,450,000

    Sold Mar 13, 2026

    15 Wright St, Westport, CT 06880

    • 3 Beds
    • 3 Baths
    • 1,998 Sq Ft
    • Built 1851

    Last Sold Summary

    • 13% Above List Price
    • $726/SF
    • 23 Days On Market

    Current Estimated Value $1,466,703

    Last Listing Agent Laurie Morris Compass Connecticut, LLC

    15 Wright St, Westport, CT 06880
    • 226 Lansdowne Unit 226, Westport, CT 06880

      Not Listed For Sale

      226 Lansdowne Unit 226, Westport, CT 06880

      • 3 Beds
      • 2 Baths
      • 1,969 Sq Ft
      • Built 1985
      226 Lansdowne Unit 226, Westport, CT 06880

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Debra Grant Show to Sell Homes, LLC

  • /29

    $939,000

    $36K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 2,361 Sq Ft

    43 Green Knolls Ln, Fairfield, CT 06824

    Welcome home to this beautifully maintained 3-bedroom Cape, ideally situated on a quiet cul-de-sac. Filled with natural light and surrounded by mature plantings and professionally landscaped grounds, this home offers the perfect blend of comfort, convenience, and lifestyle. Just minutes from the Merritt Parkway, I-95, Metro North, vibrant downtown Fairfield, exceptional restaurants, shopping, and

    Carol Frattaroli William Pitt Sotheby's Int'l

    43 Green Knolls Ln, Fairfield, CT 06824
  • /7

    $2,850 Per Month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    1916 Post Rd, Fairfield, CT 06824

    Discover the best of Fairfield living at 1916 Post Road. These newly developed one-bedroom, one-bath apartments offer bright spacious living. Inside, you'll find a modern kitchen with stainless steel appliances, granite countertops, and sleek cabinetry. The bathroom is beautifully updated with granite finishes, while the large bedroom provides plenty of space to relax and unwind. New flooring

    Salvatore Dinardo Westfair Realty Group, LLC

    1916 Post Rd, Fairfield, CT 06824
  • 114 Cross Hwy, Westport, CT 06880

    $2,550,000

    Sold Aug 06, 2026

    114 Cross Hwy, Westport, CT 06880

    • 5 Beds
    • 4.5 Baths
    • 4,179 Sq Ft
    • Built 1964

    Last Sold Summary

    • 6% Below List Price
    • $610/SF
    • 36 Days On Market

    Current Estimated Value $2,635,106

    Last Listing Agent Robert Appell Coldwell Banker Realty

    114 Cross Hwy, Westport, CT 06880
    • 127 Lansdowne Unit 127, Westport, CT 06880

      Not Listed For Sale

      127 Lansdowne Unit 127, Westport, CT 06880

      • 2 Beds
      • 2.5 Baths
      • 2,100 Sq Ft
      • Built 1985
      127 Lansdowne Unit 127, Westport, CT 06880

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Joan Wright Compass Connecticut, LLC

  • /37

    $1,949,000

    Pending
    • 5 Beds
    • 5.5 Baths
    • 4,606 Sq Ft

    1680 Cross Hwy, Fairfield, CT 06824

    1680 Cross Highway is a nod to all of the pristine, old-school colonials in leafy Greenfield Hill, however, its interiors and landscape have been beautifully updated to reflect the needs of the current owners, a modern family of four, with a nanny and friends continuously coming and going. The chef's kitchen was masterfully streamlined with new GE Monogram appliances, an oversized center island,

    Michael Mombello Compass Connecticut, LLC

    1680 Cross Hwy, Fairfield, CT 06824
  • /23

    $8,200 Per Month

    • 4 Beds
    • 3 Baths
    • 2,408 Sq Ft
    • House for Rent

    5 Turtleback Ln, Westport, CT 06880

    Available August 19. Welcome to this charming, sun-filled four-bedroom, three-bath home tucked away on a peaceful Westport cul-de-sac. The inviting main level features a spacious living room with recessed lighting and a wood-burning fireplace, an elegant formal dining room with wainscoting, and an updated eat-in kitchen. A separate family room offers a second wood-burning fireplace, tile

    Suzanne Fitzmaurice Sholes The Riverside Realty Group

    5 Turtleback Ln, Westport, CT 06880
  • 99 Acorn Ln, Southport, CT 06890

    $2,200,000

    Sold Jun 24, 2026

    99 Acorn Ln, Southport, CT 06890

    • 4 Beds
    • 3.5 Baths
    • 2,993 Sq Ft
    • Built 1953

    Last Sold Summary

    • 38% Above List Price
    • $735/SF
    • 15 Days On Market

    Current Estimated Value $1,763,716

    Last Listing Agent Tara Hawley Coldwell Banker Realty

    99 Acorn Ln, Southport, CT 06890
    • 1986 Kings Hwy, Fairfield, CT 06824

      Est $634,683

      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

      • 20 Days On Market

      Last Listing Agent Lani Liu-Helisch Sovereign Properties

  • /36

    $5,995,000

    $504K PRICE DROP
    • 5 Beds
    • 7 Baths
    • 6,189 Sq Ft

    775 Sasco Hill Rd, Fairfield, CT 06824

    775 Sasco Hill Road is an extraordinary estate where timeless elegance meets modern luxury. Impeccably renovated and beautifully curated by the current owners, this sophisticated residence offers three full levels of refined living set across five private, park-like acres. A dramatic cathedral foyer and soaring 9-foot ceilings create an immediate sense of scale and light, while the thoughtfully

    Suzy Ryan William Raveis Real Estate

    775 Sasco Hill Rd, Fairfield, CT 06824
  • /14

    $3,000 Per Month

    • 4 Beds
    • 1 Bath
    • 1,386 Sq Ft
    • House for Rent

    25-27 Jetland Place Unit 27, Bridgeport, CT 06605

    Spacious 4-bedroom, 1-bath second-floor rental located in the desirable Black Rock area of Bridgeport, CT. This bright and well-maintained unit features generous living space and plenty of natural light throughout. Conveniently located near shopping, restaurants, parks, public transportation, and just minutes from the Black Rock waterfront and Fairfield Metro station. Perfect for families or

    Jason Brown YellowBrick Real Estate LLC

    25-27 Jetland Place Unit 27, Bridgeport, CT 06605
  • 84 Algonquin Rd, Fairfield, CT 06825

    $1,007,500

    Sold Apr 21, 2026

    84 Algonquin Rd, Fairfield, CT 06825

    • 4 Beds
    • 4 Baths
    • 3,257 Sq Ft
    • Built 1920

    Last Sold Summary

    • 12% Above List Price
    • $309/SF
    • 19 Days On Market

    Current Estimated Value $1,022,225

    Last Listing Agent Carol McCullough Berkshire Hathaway NE Prop.

    84 Algonquin Rd, Fairfield, CT 06825
    • 64 Sterling St, Fairfield, CT 06825

      Est $809,592

      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

      • 55 Days On Market

      Last Listing Agent Michael Jabick Keller Williams Realty

  • /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 Keller Williams Realty Prtnrs.

    203 Lenox Ave Unit 205, Bridgeport, CT 06605
  • /26

    $20,000 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,998 Sq Ft
    • House for Rent

    69 Richmondville Ave, Westport, CT 06880

    Escape to your own private sanctuary in this sun-filled, flexible layout home located in the highly desirable In-Town neighborhood, close to all of Westport's amenities. Offering a rare blend of dramatic natural beauty and everyday convenience, this property features breathtaking, unobstructed views of a waterfall on Lee's Pond, which flows directly into the historic Saugatuck River. This is a

    Deborah Kulback William Pitt Sotheby's Int'l

    69 Richmondville Ave, Westport, CT 06880
  • 26 Hitchcock Rd, Westport, CT 06880

    $2,700,000

    Sold Jan 26, 2026

    26 Hitchcock Rd, Westport, CT 06880

    • 5 Beds
    • 5 Baths
    • 4,549 Sq Ft
    • Built 2025

    Last Sold Summary

    • $594/SF
    • 224 Days On Market

    Current Estimated Value $2,693,891

    Last Listing Agent Mar Jennings Higgins Group Bedford Square

    26 Hitchcock Rd, Westport, CT 06880
    • 1120 Hulls Hwy, Southport, CT 06890

      Est $1,056,053

      Not Listed For Sale

      1120 Hulls Hwy, Southport, CT 06890

      1120 Hulls Hwy, Southport, CT 06890

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Patty Eilenberg Berkshire Hathaway NE Prop.

Showing Results 241 - 280, Page 7 of 18

How to Buy a Home How to Finance a Home How to Sell a Home