Southport, CT Homes

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  /39

  $9,750,000

  • 6 Beds
  • 9 Baths
  • 5,920 Sq Ft

  828 Sasco Hill Rd, Fairfield, CT 06824

  "Pebbles" | Iconic Sasco Hill Estate Timeless Design. Storied Past. Unrivaled Views. A distinguished Georgian Revival estate set on nearly 3 acres, the largest lot along this coveted stretch of Sasco Hill. With sweeping, unobstructed views of the Country Club of Fairfield, Southport Harbor, Long Island Sound, and the Manhattan skyline, this iconic property offers an extraordinary blend of

  Wendy Ryan Brown Harris Stevens

  828 Sasco Hill Rd, Fairfield, CT 06824
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  /10

  $2,350 total monthly price

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

  181 Longview Ave, Fairfield, CT 06824

  Beautifully renovated 2-bedroom, 1-bath apartment. The spacious eat-in kitchen and bathroom feature brand-new white shaker cabinets, new appliances, quartz counters, and stainless steel sinks and fixtures. The unit has refinished hardwood floors throughout. The spacious living room has an abundance of light, and both bedrooms are large, one with double closets. There is a dedicated laundry room

  Lindsey Rosen William Pitt Sotheby's Int'l

  181 Longview Ave, Fairfield, CT 06824
• 

  $2,825,000 Sold Oct 17, 2025

  • 3,015 Sq Ft
  • $937/SF
  • 15 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1959

  4 Budner Ln, Westport, CT 06880

  Featured in New England Home, Luxe Magazine, and Westport Lifestyle, 4 Budner Lane is an award-winning home located on a private street in Westport's coveted Greens Farms neighborhood. Taken to the studs in 2019, this 4-bedroom, 3-bathroom residence was completely reimagined with the highest level of craftsmanship, design, and functionality. Every detail of this four bedroom, three full bath home

  Carly Woodard William Raveis Real Estate

  4 Budner Ln, Westport, CT 06880
• 

  Est $4,783,111 Not Listed For Sale

  • 5 Beds
  • 6.5 Baths
  • 7,200 Sq Ft

  13 Caccamo Ln, Westport, CT 06880

  13 Caccamo Ln, Westport, CT 06880
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  /6

  $390,000

  • Land
  • 2 Acres
  • $195,000 per Acre

  6 Fox Run Ln, Westport, CT 06880

  This secluded property in Westport, CT at 6 Fox Run Lane offers an opportunity to submit your desired dream home plans to Westport on this picturesque 2 acres of rare undeveloped land. The lot is nestled in a prestigious upscale neighborhood and offers a tranquil bucolic setting, and is surrounded by nature. The new owner may design a custom home to suit your family's needs and preferences

  Derek Greene Derek Greene

  6 Fox Run Ln, Westport, CT 06880
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  /38

  $4,800 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,225 Sq Ft
  • House for Rent

  93 Catherine Terrace, Fairfield, CT 06824

  Commuter's dream location close to train station, I-95, town center & beaches. Quiet inner side of horseshoe-shaped road with no through traffic. Desirable neighborhood in sought after school district. Fenced, flat back yard. Freshly painted 3 BR, 1.5 BA with EIK, dining room, living room, large eat-in-kitchen with plenty of cabinets. 1-car garage, new a/c (2025), new refrigerator (2025), new

  Heidi Cinder William Raveis Real Estate

  93 Catherine Terrace, Fairfield, CT 06824
• 

  $415,000 Sold Oct 17, 2025

  • 1,036 Sq Ft
  • $401/SF
  • 17 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1984

  120 Beachview Ave Unit 246, Bridgeport, CT 06605

  Your view everyday ! Welcome to waterfront living in the heart of trendy Black Rock near St Mary's by the Sea. This updated 2-bedroom, 1.5-bath townhouse offers the perfect blend of chic updates and coastal charm. Experience breezy seaside living from your own private deck. Sliding glass doors frame the updated, eat-in kitchen with new quartz counters, stainless steel appliances, new flooring and

  Kelly Finn Coldwell Banker Realty

  120 Beachview Ave Unit 246, Bridgeport, CT 06605
• 

  Est $1,787,254 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 3,706 Sq Ft

  38 Bauer Place Extension, Westport, CT 06880

  38 Bauer Place Extension, Westport, CT 06880
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  /35

  $4,300,000

  • 7 Beds
  • 5 Baths
  • 6,000 Sq Ft

  378 Penfield Rd, Fairfield, CT 06824

  Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with

  Helene Salerno Preoh, LLC

  378 Penfield Rd, Fairfield, CT 06824
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  /23

  $3,200 total monthly price

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

  44 Roseville Rd, Westport, CT 06880

  Nestled in a serene, landscaped setting, this enchanting 1-bedroom, 1-bath cottage offers an idyllic retreat where tranquility meets storybook charm. Located next to a shimmering pond with calming water fountain, this intimate cottage boasts a delightful bedroom, the perfect sanctuary for rest and relaxation. Next to the bedroom is the bathroom with a walk-in shower. The open-concept living area

  Stephen Pratt Keller Williams Realty

  44 Roseville Rd, Westport, CT 06880
• 

  $550,000 Sold Oct 17, 2025

  • 924 Sq Ft
  • $595/SF
  • 38 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1920

  67 Rakoczy Ave, Fairfield, CT 06824

  Bring your builders. Beautiful level lot in convenient location. Located near I-95, Merritt Parkway, shopping & restaurants. B Zone

  Gail Williams Coldwell Banker Realty

  67 Rakoczy Ave, Fairfield, CT 06824
• 

  Est $2,323,916 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,934 Sq Ft

  181 Long Lots Rd, Westport, CT 06880

  181 Long Lots Rd, Westport, CT 06880
• 

  

  /37

  $4,300,000

  • 7 Beds
  • 5.5 Baths
  • 6,000 Sq Ft

  394 Penfield Rd, Fairfield, CT 06824

  Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7 bedrooms, 5 baths, library with

  Helene Salerno Preoh, LLC

  394 Penfield Rd, Fairfield, CT 06824
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  /40

  $5,000 total monthly price

  • 3 Beds
  • 1.5 Baths
  • 1,363 Sq Ft
  • House for Rent

  31 Hillandale Rd, Westport, CT 06880

  Here is the perfect opportunity to enjoy the charm and beauty of Westport and everything this sought-after town has to offer. This wonderfully maintained 3-bedroom, 1.5-bath home is located on a quiet road in a convenient Westport neighborhood. The light filled eat-in kitchen has new stainless steel appliances and quartz countertops. There is a spacious living room, a formal dining room and an

  Sandra Calise Cenatiempo Settlers & Traders

  31 Hillandale Rd, Westport, CT 06880
• 

  $2,112,500 Sold Oct 16, 2025

  • 5,256 Sq Ft
  • $402/SF
  • 133 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2025

  59 Thornhill Rd, Fairfield, CT 06824

  Located on one of the most coveted cul-de-sacs in Fairfield's University area, this Newly Built Colonial offers a perfect blend of classic charm & modern luxury. A welcoming stone-trimmed front porch sets the stage for quiet mornings with coffee, while inside, 5-7 bedrooms and 5.5 bathrooms provide ample space for comfortable living and entertaining. The gorgeous open-concept Kitchen with eating

  Julie Vanderblue Higgins Group Real Estate

  59 Thornhill Rd, Fairfield, CT 06824
• 

  Est $2,877,943 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,704 Sq Ft

  52 Center St, Westport, CT 06880

  52 Center St, Westport, CT 06880
• 

  

  /22

  $198,000

  • 1 Bed
  • 1 Bath
  • 911 Sq Ft

  2370 North Ave Unit 5A, Bridgeport, CT 06604

  Spacious 1-bedroom condo in sought-after Brooklawn, perfectly located near I-95! This 5th-floor gem boasts a bright, semi-open layout, a private balcony for relaxing, and a custom-designed closet. Enjoy the convenience of a 24-hour doorman, assigned parking, and on-site laundry. It's dog-friendly, too! Your dream condo awaits-schedule a tour today!

  Johan Tola Keller Williams Realty Group

  2370 North Ave Unit 5A, Bridgeport, CT 06604
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  /19

  $6,000 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 2,553 Sq Ft
  • House for Rent

  90 Sasco Hill Terrace, Fairfield, CT 06824

  Wonderful home on cherished Sasco Hill Cul-de-Sac in fantastic location. Freshly painted, light and bright with excellent space. In addition to 3 bedrooms on Upper Level (including large Primary Suite), the Main Level offers Guest Space. Living Room has a cozy gas fireplace. Family room has sliders that open to large deck and a fantastic private property. Eat-in-Kitchen has large windows with

  Ellen Fusco Compass Connecticut, LLC

  90 Sasco Hill Terrace, Fairfield, CT 06824
• 

  $400,000 Sold Oct 16, 2025

  • 1,075 Sq Ft
  • $372/SF
  • 22 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1959

  27 Bloomfield Dr, Fairfield, CT 06825

  OFFER DEADLINE MON. 9/22 AT 2:00PM HIGHEST & BEST Prime Opportunity to live in Fairfield on Exceptional Land - Rebuild or Renovate! The house sits on an expansive, double-sized (.3 acre) lot in the Fairfield Wood's section of Fairfield - a rare and valuable piece of land offering incredible potential for builders, investors, or buyers ready to create their dream home from the ground up. This

  Kathleen DeRossi William Pitt Sotheby's Int'l

  27 Bloomfield Dr, Fairfield, CT 06825
• 

  Est $822,698 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,216 Sq Ft

  17 Richmondville Ave, Westport, CT 06880

  17 Richmondville Ave, Westport, CT 06880
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  /40

  $4,600,000

  • 4 Beds
  • 3.5 Baths
  • 4,636 Sq Ft

  87 Red Coat Rd, Westport, CT 06880

  MOST UNIQUE HOUSE IN WESTPORT LARGE LOG HOME ON THE RIVER THAT IS STOCKED WITH TROUT. INGROUND GUNITE POOL BEAUTIFUL GROUNDS VERY PRIVATE ONE FLOOR LIVING. 4 BEDROOMS 3.5 BATHS. 1 HOUR TO NYC BEACH ACCESS. WONDERFUL RARE OPPORTUNITY TO OWN THE HOME YOU HAVE ALWAYS WONDERED ABOUT. THE BEAUTIFUL TRANQUIL RIVERVIEW LODGE LOG HOME THAT SITS ON THE MAJESTIC SAUGATUCK RIVER. WITH OVER 500+ FEET OF

  Rebecca Ellsley Higgins Group Bedford Square

  87 Red Coat Rd, Westport, CT 06880
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  /36

  $6,100 total monthly price

  • 2 Beds
  • 3.5 Baths
  • 2,692 Sq Ft
  • House for Rent

  135 Regents Park, Westport, CT 06880

  Welcome to this bright and spacious 2-bedroom, 3.5-bath condo in one of Westport's most desirable communities! With nearly 2,700 sq. ft. across three levels, this rental offers comfort, style, and space in a peaceful, natural setting. The sun-filled main level features an open floor plan with a Living Room and Dining Room that both open to a wraparound deck-perfect for entertaining or relaxing

  Linda Skolnick Coldwell Banker Realty

  135 Regents Park, Westport, CT 06880
• 

  $1,210,000 Sold Oct 15, 2025

  • 2,659 Sq Ft
  • $455/SF
  • 23 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1947

  14 Dill Rd, Fairfield, CT 06824

  Welcome to Dill Cottage! This sun-filled, expanded Cape Cod home is loaded with custom architectural details, including vaulted ceilings, arched doorways, elegant moldings, and hardwood floors throughout. Ideally located in the sought-after University area, close to town and train, this home is an entertainer's dream. The stunning eat-in kitchen with a cozy sitting area features custom cabinetry,

  Carrie Sakey Coldwell Banker Realty

  14 Dill Rd, Fairfield, CT 06824
• 

  Est $4,614,574 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 7,032 Sq Ft

  6 James Ln, Westport, CT 06880

  6 James Ln, Westport, CT 06880
• 

  

  /3

  $799,000

  • Land
  • 0.37 Acre
  • $2,159,459 per Acre

  0 Battery Park Dr, Bridgeport, CT 06605

  Owner is Agent. Financing Available. Welcome to an exceptional opportunity in the highly sought after enclave of Black Rock! Nestled on a .37 acre lot, this parcel boasts unparalleled vistas of the majestic Long Island Sound, offering a canvas for your visionary masterpiece. With sweeping views that stretch across the horizon, this prime location beckons investors and builders alike to seize the

  Lydia. Gach eRealty Advisors, Inc.

  0 Battery Park Dr, Bridgeport, CT 06605
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  /27

  $8,200 total monthly price

  • 4 Beds
  • 3 Baths
  • 4,544 Sq Ft
  • House for Rent

  177 Brett Rd, Fairfield, CT 06824

  Beautifully updated FURNISHED colonial in Greenfield Hill. Designers own home. A gorgeous entry foyer greets you & opens to a large living room with cathedral ceilings, fireplace & large picture window.Continue into an absolutely fabulous, sun-filled eat-in kitchen w/ full dining area, large island for entertaining, a cozy window seat and sliders which lead to a spacious deck, gorgeous & very

  Carol Alexander Berkshire Hathaway NE Prop.

  177 Brett Rd, Fairfield, CT 06824
• 

  $625,000 Sold Oct 15, 2025

  • 1,567 Sq Ft
  • $399/SF
  • 95 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1955

  4 Heather Hill, Westport, CT 06880

  Welcome to 4 Heather Hill in Westport! This charming 4 bedroom, 1.5 bath Cape Cod-style home is ideally located on a private road right in the heart of Central Westport. Nestled on a serene quarter-acre lot that is bordered in the rear by a classic stone wall, this property offers both privacy and promise. This home awaits your personal touches and updates. Several key improvements have already

  Matthew Loverci Coldwell Banker Realty

  4 Heather Hill, Westport, CT 06880
• 

  Est $2,688,102 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,534 Sq Ft

  2 Florian Ct, Westport, CT 06880

  2 Florian Ct, Westport, CT 06880
• 

  /2

  $4,999,000

  • 6 Beds
  • 8 Baths
  • 8,988 Sq Ft

  22 Morningside Dr S, Westport, CT 06880

  This 9000+ SQFT timeless home boasts an enormous kitchen complete with custom cabinetry, a double island, walk-in pantry, and butler's pantry-a chef's dream come true. The open floor plan integrates the kitchen with the inviting family room and adjacent library, creating a perfect space for intimate gatherings and grand entertaining. Upstairs, the primary suite features two walk-in closets and a

  John Schiaroli Coldwell Banker Realty

  22 Morningside Dr S, Westport, CT 06880
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  /30

  $6,750 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Apartment for Rent

  5 Church Ln Unit 410, Westport, CT 06880

  ~HIGH END LIVING~ This home is located in the "Golden Triangle" of downtown Westport. Bedford Square is a unique multi-purpose destination that includes premier residences, beautiful public areas, high-end retail and dining. Bedford Square is the culmination of the renovation and restoration of the stately 1923 Bedford Mansion and historic Firehouse. Bedford Square is ideally situated in the

  Matt Murray Higgins Group Bedford Square

  5 Church Ln Unit 410, Westport, CT 06880
• 

  $2,125,000 Sold Oct 15, 2025

  • 6,596 Sq Ft
  • $322/SF
  • 59 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1966

  92 Hornbeam Rd, Fairfield, CT 06824

  Perfectly sited on a quiet cul-de-sac in the Greenfield Hill neighborhood, this exquisite farmhouse-style home offers over 5,000 sq ft of elegant living space on a spectacular, level property. The classic character and contemporary elegance defines this home offering 5 bedrooms, 5 baths, custom millwork, refined designer details and exceptional outdoor living. Step into a gracious foyer flanked

  Jennifer Lockwood Coldwell Banker Realty

  92 Hornbeam Rd, Fairfield, CT 06824
• 

  Est $934,066 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 2,291 Sq Ft

  20 Rumpenmile Ave, Westport, CT 06880

  20 Rumpenmile Ave, Westport, CT 06880
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  /16

  $6,785,000 New Construction

  • 6 Beds
  • 9 Baths
  • 7,888 Sq Ft

  14 Burr School Rd, Westport, CT 06880

  RARE OPPORTUNITY TO CUSTOMIZE NEW CONSTRUCTION BY COASTAL LUXURY HOMES. PLANS APPROVED & PERMITS IN PLACE. CONSTRUCTION CAN BEGIN IMMEDIATELY, SAVE 6+ MOS ON NEW BUILD TIMELINE. This ultra luxury modern cul-de-sac residence features stucco exterior, DaVinci Boral roof, and expansive windows up to 10ft high. Main level includes luxe chef's kitchen w/ breakfast room opening to the great room with

  Jennifer Tanner The Riverside Realty Group

  14 Burr School Rd, Westport, CT 06880
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  /38

  $4,500 total monthly price

  • 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
• 

  $5,499,000 Sold Oct 15, 2025

  • 9,550 Sq Ft
  • $576/SF
  • 112 Days On Market

  • 6 Beds
  • 9 Baths
  • Built 2025

  11 Tierney Ln, Westport, CT 06880

  Combining classic design with modern detailing, this masterfully crafted home by an established local builder of premier residences is sure to delight even the most discerning buyer. Impressively positioned at the end of a private lane in the heart of the Greens Farms, this one of 2 exceptional custom homes. The main level exudes luxury, showcasing the expert millwork that flows throughout the

  Laurie Crouse Coldwell Banker Realty

  11 Tierney Ln, Westport, CT 06880
• 

  Est $3,718,788 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 6,885 Sq Ft

  4 Willow Walk, Westport, CT 06880

  4 Willow Walk, Westport, CT 06880
• 

  

  /40

  $1,950,000 New Construction

  • 5 Beds
  • 6 Baths
  • 4,239 Sq Ft

  309 Hunyadi Ave, Fairfield, CT 06824

  Welcome to 309 Hunyadi Avenue, a spectacular 5-bedroom, 6-bath custom Colonial on a quiet cul-de-sac road. Built as the builder's personal home, it showcases extraordinary commitment to quality materials, thoughtful craftsmanship, & exceptional lighting design. Primary suite is like nothing else-featuring 18ft white oak backlit cathedral ceilings, stunning 11ft custom window, 9ft crystal

  Julie Vanderblue Higgins Group Real Estate

  309 Hunyadi Ave, Fairfield, CT 06824
• 

  

  /19

  $4,800 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,285 Sq Ft
  • House for Rent

  1023 Black Rock Turnpike Unit 1023, Fairfield, CT 06825

  A townhouse that feels like a stand-alone home! This Colonial/Townhouse has high ceilings and hardwood floors throughout. The open floor plan leads to a spacious eat-in kitchen with granite counters, stainless appliances, and gas cooking! The second level has a large master suite with a full bath, double sinks, and an oversized walk-in closet. Three more bedrooms plus a hall bath and laundry

  Katerina Hendrickson Coldwell Banker Realty

  1023 Black Rock Turnpike Unit 1023, Fairfield, CT 06825
• 

  $1,829,700 Sold Oct 15, 2025

  • 4,710 Sq Ft
  • $388/SF
  • 11 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2006

  297 Romanock Rd, Fairfield, CT 06825

  A spectacular custom Colonial combining timeless elegance and modern comfort, set on a beautifully landscaped and fully fenced 0.6-acre lot in Fairfield's coveted Lake Hills community. With over 4,700 sqft of refined living space, this 4bedroom, 3.5bath home offers the perfect mix of classic charm, thoughtful updates, and exceptional functionality. Step into a grand entry foyer and light-filled

  Robin Righter Houlihan Lawrence

  297 Romanock Rd, Fairfield, CT 06825
• 

  Est $5,226,717 Not Listed For Sale

  • 6 Beds
  • 7.5 Baths
  • 8,080 Sq Ft

  39 Maple Ave S, Westport, CT 06880

  39 Maple Ave S, Westport, CT 06880

Showing Results 521 - 560, Page 14 of 18