Southport, CT Homes

• 

  

  

  /39

  $3,250,000 Pending

  • 5 Beds
  • 6 Baths
  • 6,027 Sq Ft

  99 Hillspoint Rd, Westport, CT 06880

  This better than new modern farmhouse nestled on 1.28 acres is a masterpiece of architectural design and sophistication and just steps from the beach, train, and shopping. Every detail of this 6,000 SF 5 Bedroom home has been meticulously curated, from the high-end materials to the advanced technology offering a modern, refined aesthetic to deliver unparalleled comfort. The double-height entry

  

  Susan Lieberman

  The Riverside Realty Group

  (203) 884-0386

  99 Hillspoint Rd, Westport, CT 06880
• 

  

  

  /23

  $3,200 per month

  • 2 Beds
  • 1.5 Baths
  • 1,134 Sq Ft
  • House for Rent

  70 Stephens Ln Unit 2, Fairfield, CT 06824

  Newly updated - this immaculate and beautiful open floor plan condo with all new appliances is available for rent. The home boast a fully updated EIK Kitchen, a living room with bay bow windows and hardwood floors, a half bath,laundry and storage on the main level. The econd floor has two bedrooms and a full bath. The primary bedroom has a walk-in-closet. Plenty of natural light and recess

  

  Hy Natarajan

  Keller Williams Prestige Prop.

  (203) 987-4651

  70 Stephens Ln Unit 2, Fairfield, CT 06824
• 

  $1,762,000 Sold Jul 11, 2025

  • 3,077 Sq Ft
  • $573/SF
  • 63 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1954

  10 Dover Rd, Westport, CT 06880

  Welcome to 10 Dover Road- Ideally situated on a peaceful cul-de-sac with a beautiful flat backyard, perfect for outdoor living and entertaining. Thoughtfully expanded and renovated for today's lifestyle, with white oak hardwood floors throughout, this home features a sun drenched living room with vaulted ceilings with a striking fireplace, a formal dining room perfect for entertaining, and an

  Georgia Wasserman Coldwell Banker Realty

  10 Dover Rd, Westport, CT 06880
• 

  Est $2,024,130 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 5,000 Sq Ft

  177 High Meadow Rd, Southport, CT 06890

  177 High Meadow Rd, Southport, CT 06890
• 

  

  

  /33

  $997,000

  • 4 Beds
  • 3.5 Baths
  • 2,434 Sq Ft

  1 Ruta Ct, Westport, CT 06880

  Seller are asking for HIGHEST AND BEST OFFERS BY MONDAY 7/14/25 at 5PM Welcome to this charming Contemporary Colonial in the sought-after Long Lots area. Nestled on a serene cul-de-sac, this bright home offers the trifecta of natural gas, city water, and sewer. 3/4 acre lot extends all the way to Long Lots Rd! Enjoy the convenience of being just minutes from town, the train, beaches, and major

  

  Hyleri Katzenberg

  Compass Connecticut, LLC

  (203) 871-0406

  1 Ruta Ct, Westport, CT 06880
• 

  

  /38

  $2,235 - $3,107 per month

  Canfield Park at Fairfield Metro

  Studio-2 Beds

  306 Canfield Ave, Bridgeport, CT 06605

  Tucked along the winding shores of Ash Creek, Canfield Park at Fairfield Metro is just a five-minute walk to the Fairfield Metro Train Station, with express rides to and from NYC and Stamford.Head a few blocks in the other direction on foot or by bike, and find yourself in the heart of Black Rock, with its charming coffee shops, fabled restaurants, bars and more.Now Leasing!

  306 Canfield Ave, Bridgeport, CT 06605
• 

  $10,250,000 Sold Jul 11, 2025

  • 12,440 Sq Ft
  • $824/SF
  • 87 Days On Market

  • 6 Beds
  • 10 Baths
  • Built 2025

  5 Fraser Rd, Westport, CT 06880

  Prepare to experience the extraordinary and discover the future at this new residence by Skyview Builders. Now complete and ready for immediate enjoyment, this world-class estate elevates the standard against which all others are measured. Set on two spectacular, level acres in the heart of Westport's premier estate section, long considered a haven for celebrities & influential figures. The gated

  Doug Bross Coldwell Banker Realty

  5 Fraser Rd, Westport, CT 06880
• 

  Est $2,783,840 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,500 Sq Ft

  2015 Redding Rd, Fairfield, CT 06824

  2015 Redding Rd, Fairfield, CT 06824
• 

  

  /29

  $849,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,638 Sq Ft

  130 Sturbridge Ln, Southport, CT 06890

  LOCATION, LOCATION, LOCATION! Perched graciously on a coveted cul-de-sac in Southport on over an acre of property, this 2,600 square foot+ home features the best of all worlds - privacy and yet just minutes from everything that Fairfield has to offer. Classic and welcoming, this first time on the market, rambling home with fabulous bones features 4 bedrooms, 2 full and 1 half bathrooms.

  

  Susan Lieberman

  The Riverside Realty Group

  (203) 633-7346

  130 Sturbridge Ln, Southport, CT 06890
• 

  

  /12

  $4,000 per month

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

  205 Hillspoint Rd, Westport, CT 06880

  WESTPORT DIRECT WATER FRONT. BEAUTIFUL SUNFILLED COTTAGE ON THE MILL POND PRESERVE.ONE BEDROOM APARTMENT ON THE SECOND FLOOR OF A PRIVATELY OWNED HOME,NEW KITCHEN WITH STAINLESS STEEL APPLIANCES,GRANITE COUNTERS, LIVING ROOM WITH GAS FIREPLACE, DINING AREA, OFFICE, LAUNDRY, STUNNING VIEWS OF THE MILL POND. ENJOY 4 SEASONS OF SERENE LIVING. MORNING COFFEE ON YOUR PRIVATE DECK, SHARED DOCK. WALK TO

  Carol Alexander Berkshire Hathaway NE Prop.

  205 Hillspoint Rd, Westport, CT 06880
• 

  $700,000 Sold Jul 10, 2025

  • 2,988 Sq Ft
  • $234/SF
  • 55 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1937

  8 Lynnbrook Rd, Fairfield, CT 06825

  Beautiful 4-bedroom, 3.5-bath Colonial located in the heart of Fairfield, just a short walk to Tunxis Hill Park with its newly updated tennis and pickleball courts, playground, and baseball fields. This home offers the perfect blend of space, comfort, and convenience. The large kitchen is full of potential and ready for your personal touch. Just off the kitchen is a spacious yet cozy living

  Lindsay Violette Houlihan Lawrence

  8 Lynnbrook Rd, Fairfield, CT 06825
• 

  Est $1,767,092 Not Listed For Sale

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

  170 Windsor Rd, Fairfield, CT 06824

  170 Windsor Rd, Fairfield, CT 06824
• 

  

  /40

  $3,879,000 Pending

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

  19 Center St, Westport, CT 06880

  Nestled on a sought-after cul-de-sac in the heart of Greens Farms, this exceptional Colonial offers beautifully finished living space across 4 levels. With 6 bedrooms, 6 full & 2 half baths, & superior craftsmanship throughout, this home is the perfect blend of timeless design & everyday comfort. Just a short walk to Greens Farms Elementary & minutes to Compo Beach, local shops, & the train, the

  

  Brett Lieberman

  The Riverside Realty Group

  (475) 262-8614

  19 Center St, Westport, CT 06880
• 

  

  /90

  $2,429 - $5,380 per month

  597 Westport Apartments

  Studio-2 Beds

  597 Westport Ave, Norwalk, CT 06851

  Situated in historic Norwalk, bordering Westport, and along Connecticut's captivating coastline, 597 Westport is the heart of all you desire in a residence. When location is of the essence, 597 Westport delivers with elegant apartment homes so perfectly set in Fairfield County, in close proximity to the train station and New York City, and thus destinations worldwide. Inspired by this backdrop,

  597 Westport Ave, Norwalk, CT 06851
• 

  $415,000 Sold Jul 10, 2025

  • 1,372 Sq Ft
  • $302/SF
  • 45 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1973

  193 Knapps Hwy, Fairfield, CT 06825

  Wonderful entry level townhouse offering open floor plan, 2 large bedrooms each with 2 large closets. Berber carpeting, 2 sliders in living room open to balcony/deck. 1.5 updated baths, and newer full size washer & dryer. Beautifully landscaped with mature plantings and trees. Common charge covers most expenses! Convenient to shopping, schools, and I-95, RTE 15, and Ffld. Metro station. 1-car

  Al DelVecchio William Raveis Real Estate

  193 Knapps Hwy, Fairfield, CT 06825
• 

  Est $320,833 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 910 Sq Ft

  90 Silliman St Unit 4B, Fairfield, CT 06824

  90 Silliman St Unit 4B, Fairfield, CT 06824
• 

  

  /28

  $6,995,000

  • 6 Beds
  • 6 Baths
  • 5,190 Sq Ft

  2 Bluewater Hill S, Westport, CT 06880

  Discover unparalleled living at 2 Bluewater Hill South, a magnificent 5000+ SF estate on one of Westport's most prestigious street just steps from Compo Beach. This exceptional home combines sophisticated coastal elegance with resort-style amenities, offering 6 bedrooms, 6 baths, and breathtaking LI Sound views. The coveted Bluewater Hill location provides exclusive private beach access while

  

  Susan Lieberman

  The Riverside Realty Group

  (203) 350-0478

  2 Bluewater Hill S, Westport, CT 06880
• 

  

  /36

  $3,250 per month

  • 3 Beds
  • 2 Baths
  • 1,755 Sq Ft
  • Apartment for Rent

  25 Cartright St Unit 5D, Bridgeport, CT 06604

  Rent this spacious 3-bedroom, 2-bathroom condo offering 1,755 square feet of living space on the 5th floor of a well-maintained building located in the desirable Brooklawn neighborhood near the Fairfield town line. The unit opens into a large foyer and features a bright, open-concept living and dining area with direct access to a private balcony overlooking mature trees. The condo comes partially

  Judes Joseph Prestige Prorealty Group

  25 Cartright St Unit 5D, Bridgeport, CT 06604
• 

  $4,200,000 Sold Jul 10, 2025

  • 6,898 Sq Ft
  • $609/SF
  • 58 Days On Market

  • 7 Beds
  • 9 Baths
  • Built 2008

  11 Gault Park Dr, Westport, CT 06880

  Elegant 8,794 Sq Ft Custom Colonial with Resort-Style Outdoor Living: Set behind stone walls and approached by a tree-lined drive, this extraordinary 8,794 sq ft custom Colonial blends timeless design with luxurious living. Finished on four impeccably crafted levels, the home showcases thoughtful design with extensive millwork and custom wall covering that add depth, texture and character, as

  Imke Lohs Compass Connecticut, LLC

  11 Gault Park Dr, Westport, CT 06880
• 

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 930 Sq Ft

  318 Knapps Hwy Unit 318, Fairfield, CT 06825

  318 Knapps Hwy Unit 318, Fairfield, CT 06825
• 

  

  /36

  $2,647,000

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

  11 Old Hill Rd, Westport, CT 06880

  Nestled in the heart of Westport's coveted Old Hill neighborhood, this home offers the charm of an English cottage and a thoughtful design that blends classic character with the modern desire for open, connected living. Encompassing nearly 4,000 square feet, it features four ensuite bedrooms, walk-in closets, and a curated layout that combines timeless architectural details with contemporary

  

  Susan Lieberman

  The Riverside Realty Group

  (203) 858-9411

  11 Old Hill Rd, Westport, CT 06880
• 

  

  /25

  $2,356 - $3,901 per month

  Creekline at Fairfield

  Studio-2 Beds

  219 Ash Creek Blvd, Fairfield, CT 06824

  Creekline, a brand new luxury apartment community in the heart of Fairfield, CT. Step into a world of unparalleled elegance and sophistication with our meticulously designed residences, where every detail speaks of quality and refinement. Located just moments from vibrant downtown Fairfield, Creekline offers a perfect blend of urban convenience and suburban tranquility. Elevate your lifestyle at

  219 Ash Creek Blvd, Fairfield, CT 06824
• 

  $160,000 Sold Jul 10, 2025

  • 755 Sq Ft
  • $212/SF
  • 66 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1918

  2811 Fairfield Ave Unit 1, Bridgeport, CT 06605

  First floor 4 room unit in desirable Black Rock Gardens. Features include bedroom, living room with two closets - can be used as extra bedroom, dining room and kitchen. Screened porch overlooking the largest courtyard in the complex. Unit has replacement windows, and large storage bin in basement. Common charges include heat, property taxes, hot water, water and sewer. Parking lot reserved for

  Gail Robinson William Raveis Real Estate

  2811 Fairfield Ave Unit 1, Bridgeport, CT 06605
• 

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  670 Kings Hwy W Unit 670, Fairfield, CT 06890

  670 Kings Hwy W Unit 670, Fairfield, CT 06890
• 

  

  /22

  $625,000

  • 3 Beds
  • 1.5 Baths
  • 1,567 Sq Ft

  58 Post Rd, Fairfield, CT 06824

  Fabulous opportunity to own this mixed-use, high profile corner residential/business property in bustling commuter friendly neighborhood of restaurants, shops, businesses and boutiques. This sidewalk and tree lined hot spot location is just mere minutes to the train station and steps to the commuter bus line. Admire tranquil water views from across the Post Road as you gaze out of the expansive

  

  Tammy Edwards

  Coldwell Banker Realty

  (203) 813-4826

  58 Post Rd, Fairfield, CT 06824
• 

  

  /17

  $1,500 per month

  • 1 Bath
  • 585 Sq Ft
  • House for Rent

  80 Cartright St Unit 6L, Bridgeport, CT 06604

  Freshly painted, gorgeous Studio in very desirable doorman building. *** Heat and Hot Water included in Rent. *** Kitchen with pass through! Lots of closets! Nice balcony for relaxing! Partially furnished with shelving unit . Assigned parking space. Laundry in lower level of building. Excellent credit and references a must....

  Paul Krumins Higgins Group Real Estate

  80 Cartright St Unit 6L, Bridgeport, CT 06604
• 

  $425,000 Sold Jul 09, 2025

  • 1,161 Sq Ft
  • $366/SF
  • 18 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1986

  57 Edge Hill Ct Unit 57, Fairfield, CT 06824

  Lovely townhome situated on a private cul-de-sac in the University area. Pristine end unit with 2 bedrooms, 1.5 bath and 1161 Sq ft. Living and Dining area have hardwood floors and a lovely Bay Window that brings in natural light. The galley kitchen has granite counters and overlooks the deck and patio (2023). Upstairs there are 2 bedrooms generous in size with properly fitted closets and access

  Lynn Dolan William Pitt Sotheby's Int'l

  57 Edge Hill Ct Unit 57, Fairfield, CT 06824
• 

  Est $1,042,532 Not Listed For Sale

  1120 Hulls Hwy, Southport, CT 06890

  1120 Hulls Hwy, Southport, CT 06890
• 

  

  /38

  $3,150,000

  • 3 Beds
  • 2.5 Baths
  • 2,554 Sq Ft

  5 Compo Hill Ave, Westport, CT 06880

  Where serenity meets luxury. Nestled into Westport's Compo Hill neighborhood, this well designed 2,500+/- SF home offers a unique blend of tranquility and sophistication. With breathtaking Long Island Sound views and a design that seamlessly integrates with the seascape, this 3-bedroom, 2 1/2 bathroom oasis redefines coastal living. Wake up to the soothing sound of waves and soak in the stunning

  

  Susan Lieberman

  The Riverside Realty Group

  (475) 267-4729

  5 Compo Hill Ave, Westport, CT 06880
• 

  

  /15

  $1,750 per month

  Blackrock Homes Apartments

  1 Bed

  45 Monroe St, Bridgeport, CT 06605

  Welcome to the NEWLY RENOVATED Blackrock Homes Apartments! The Blackrock neighborhood of Bridgeport, CT is a desirable location with a bohemian vibe. Blackrock features great restaurants and bars, with live music and an engaging crowd, not to mention the beautiful waterfront. You are only minutes to the Metro North station and Fairfield, CT. This vintage building is being renovated

  45 Monroe St, Bridgeport, CT 06605
• 

  $1,888,000 Sold Jul 09, 2025

  • 2,912 Sq Ft
  • $648/SF
  • 48 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1947

  18 Stoneboat Rd, Westport, CT 06880

  Quietly set near the end of a scenic cul-de-sac on an acre of park-like property, this sophisticated home blends dramatic modern flair with Connecticut charm, in a flexible package which includes an accessory apartment. The unique features of this home make it ideal for multi-generational living, home office use, or for anyone seeking ample space in beautiful surroundings. Specimen plantings,

  Barbara Bross Coldwell Banker Realty

  18 Stoneboat Rd, Westport, CT 06880
• 

  Est $1,216,507 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,072 Sq Ft

  41 Reynolds Dr, Fairfield, CT 06824

  41 Reynolds Dr, Fairfield, CT 06824
• 

  

  /24

  $609,999

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  449 High St, Fairfield, CT 06824

  Welcome to your dream home in the heart of Fairfield! This beautifully renovated 3-bedroom, 2-bathroom gem offers the perfect blend of classic charm and modern updates. Step inside to find a bright, open floor plan with gleaming hardwood floors, a brand-new kitchen featuring stainless steel appliances and quartz countertops, and two stylishly updated bathrooms. Enjoy morning coffee on the front

  

  Gary Crawford

  RE/MAX RISE

  (475) 252-5285

  449 High St, Fairfield, CT 06824
• 

  

  /36

  $12,000 per month

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft
  • House for Rent

  53 Sylvan Rd N, Westport, CT 06880

  Nestled on 1.36 picturesque acres in Old Hill, this renovated antique home is brimming with character and modern comforts. Just moments from town, Post Road, and schools, the enchanting professional landscaped grounds feature specimen and fruit trees, a built-in BBQ and fireplace, and a wisteria-draped pergola over a stone patio. A charming barn offers additional storage or creative use. Inside,

  Erica Acheychek Coldwell Banker Realty

  53 Sylvan Rd N, Westport, CT 06880
• 

  $360,000 Sold Jul 09, 2025

  • 2,598 Sq Ft
  • $139/SF
  • 53 Days On Market

  • 6 Beds
  • 3.5 Baths
  • Built 1910

  599 Laurel Ave, Bridgeport, CT 06605

  This Half Duplex is notary spacious, comparable is size to two average single-family homes combined. The inclusion of a finish basement enhances its appeal, providing additional living or recreation space. Giving its generous size and layout, 599 Laurel presents a versatile opportunity, suitable to accommodating a large family or as a potential investment property.

  Ocilene De-Carvalho Century 21 Scala Group

  599 Laurel Ave, Bridgeport, CT 06605
• 

  Est $2,379,475 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 5,094 Sq Ft

  3270 Sturges Hwy, Westport, CT 06880

  3270 Sturges Hwy, Westport, CT 06880
• 

  

  /25

  $3,999,000

  • 6 Beds
  • 8 Baths
  • 6,000 Sq Ft

  57 Evergreen Ave, Westport, CT 06880

  Walk to downtown shops and restaurants from this stunning, reimagined, & rebuilt 1920 Dutch colonial home, situated on a spacious 1.17-acre in-town property.This is truly a work of art, as 2 properties have been seamlessly combined into one, creating a private oasis set way back from the road.Upon entering the home, you will be captivated by the meticulous attention to detail & the perfect blend

  

  Hyleri Katzenberg

  Compass Connecticut, LLC

  (475) 253-3404

  57 Evergreen Ave, Westport, CT 06880
• 

  

  /35

  $1,955 per month

  Cypress Apartments

  1 Bed

  585 Ellsworth St, Bridgeport, CT 06605

  Mid-Rise Building with Elevator Spacious 4th floor 1 bedroom. This apartment offers vinyl flooring throughout, large closets and comes fully equipped with appliances. All of our apartments include Heat, Hot water, and cooking gas. Comes with 1 free assigned parking spot. Cypress Apartments is ideally located just minutes from top-tier restaurants, trendy bistros, and vibrant nightlife.

  585 Ellsworth St, Bridgeport, CT 06605
• 

  $1,190,000 Sold Jul 08, 2025

  • 2,740 Sq Ft
  • $434/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1954

  94 Orchard Hill Dr, Fairfield, CT 06824

  *HIGHEST & BEST IS DUE BY MONDAY, JUNE 9 @ 3:00 P.M. Nestled on charming Orchard Hill Drive, this lovingly maintained colonial home offers timeless appeal and everyday comfort. Featuring 4 bedrooms and 3 full baths on a picturesque, level lot, the home welcomes you with classic curb appeal and a bright, spacious interior. The living room centers around a cozy wood-burning fireplace, creating a

  Tammy Edwards Coldwell Banker Realty

  94 Orchard Hill Dr, Fairfield, CT 06824
• 

  Est $4,796,561 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 7,250 Sq Ft

  41 North Ave, Westport, CT 06880

  41 North Ave, Westport, CT 06880

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