Southport, CT Homes

• 

  

  

  /17

  $1,450,000

  • 3 Beds
  • 2.5 Baths
  • 1,549 Sq Ft

  113 Kings Hwy N, Westport, CT 06880

  Amazing Opportunity! Charming 1920"s colonial with wonderful 1416 sq ft legal rental cottage. Bright sunny front house freshly painted and beautifully maintained. Hardwood floors throughout, newer kitchen, delightful sun room, perfect for home office. MBR w/charming dressing room and w/i closet plus 2 additional brs and hall bath. Cottage features a great 2 bedroom apartment with vaulted ceiling

  Regina Kendig William Raveis Real Estate

  113 Kings Hwy N, Westport, CT 06880
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  /14

  $1,300 total monthly price

  • 1 Bed
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  122 Hansen Ave Unit 3, Bridgeport, CT 06605

  Lovely 1 bed / 1 bath 3rd floor apartment/studio for rent in Blackrock. Clean and move in condition. Utilities included, (heat, hot water & electricity. Tenant pays gas for cooking only and cable/internet. On street parking. Close to I-95, bus routes, Metro North and all Black Rock shops & restaurants. Ready for immediate occupancy. No smoking or pets. 1 year lease minimum. 2 deposits & 1st

  Sergio Bedoya William Raveis Real Estate

  122 Hansen Ave Unit 3, Bridgeport, CT 06605
• 

  $708,500 Sold Nov 06, 2025

  • 1,682 Sq Ft
  • $421/SF
  • 50 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  225 Papermill Ln, Fairfield, CT 06824

  Enjoy the convenience of walking to town and the train from this charming 3-bedroom, 2-bath home in the highly sought-after University area. Situated on an oversized lot, the property is perfect for entertaining. The living and dining rooms open through sliders to a covered patio, seamlessly connecting indoor and outdoor living. All three bedrooms feature hardwood floors and share easy access to

  Karen Cross William Raveis Real Estate

  225 Papermill Ln, Fairfield, CT 06824
• 

  Est $3,711,021 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,955 Sq Ft

  5 Country Ln, Westport, CT 06880

  5 Country Ln, Westport, CT 06880
• 

  

  

  /18

  $325,000

  • 2 Beds
  • 1.5 Baths
  • 715 Sq Ft

  89 Grace St, Fairfield, CT 06825

  Amazing Fairfield opportunity at 89 Grace St. Prime location close to downtown, I-95, and the Merritt Parkway. 2 bedrooms, 1 bath, with an English Pub-styled kitchen. Great bones and plenty of character. Hardwood floors, off street parking, and strong potential for updates and personalization. Ideal for buyers seeking location and value. Selling as is.

  RJ Radcliff Coldwell Banker Realty

  89 Grace St, Fairfield, CT 06825
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  /10

  $1,700 total monthly price

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft
  • Condo for Rent

  2979 Fairfield Ave Unit R1, Bridgeport, CT 06605

  Renovated 1st floor Black Rock apartment features high efficiency air conditioning and heating, fully applianced including washer and dryer, extra storage along with off street parking. Conveniently located steps to restaurants/dining/nightlife, shopping, St. Mary's by the Sea with easy access to Metro North train station and I-95. Tenant to provide complete RentSpree application, proof of income

  2979 Fairfield Ave Unit R1, Bridgeport, CT 06605
• 

  $1,175,000 Sold Nov 06, 2025

  • 3,131 Sq Ft
  • $375/SF
  • 27 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1952

  300 Winnepoge Dr, Fairfield, CT 06825

  Welcome to 300 Winnepoge, a beautifully appointed home in Fairfield's desirable Lake Hills community. Set on a sun-filled corner lot with a large flat yard, this property combines classic charm with thoughtful updates and private association amenities. Step inside to find a spacious kitchen anchored by a 9' center island, granite countertops, and abundant skylights that flood the space with

  Geo Crume Keller Williams Prestige Prop.

  300 Winnepoge Dr, Fairfield, CT 06825
• 

  Est $1,000,791 Not Listed For Sale

  • 4 Beds

  32 Hale St, Westport, CT 06880

  32 Hale St, Westport, CT 06880
• 

  

  /7

  $4,700,000

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

  11 Wake Robin Rd, Westport, CT 06880

  Welcome to 11 Wake Robin Road Located in the sought-after Greens Farms area of Westport, this dramatic new construction sits on a quiet, desirable cul-de-sac. This 6,000+ sq ft contemporary colonial spans three finished levels with 9-foot ceilings throughout and will feature 6 bedrooms and 5.5 bathrooms. Meticulous craftsmanship, elegant finishes, and abundant natural light combine to create a

  Judi Lake The Riverside Realty Group

  11 Wake Robin Rd, Westport, CT 06880
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  /33

  $2,200 total monthly price

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

  174 Brentwood Ave Unit 1st Floor, Fairfield, CT 06825

  Fairfield First Floor, 4 room apartment, wood flooring throughout, eat in kitchen with walk in pantry, living room, bedroom, 4th room-flex space as 2nd bedroom/dining room/office space, new kitchen cabinets, countertops, and dishwasher, secure private storage area, front balcony, plenty of private parking, backyard. Rent includes water/sewer/garbage, laundry hook ups in basement. $2200/month.

  Nathaniel Rodriguez YellowBrick Real Estate LLC

  174 Brentwood Ave Unit 1st Floor, Fairfield, CT 06825
• 

  $2,337,500 Sold Nov 06, 2025

  • 3,156 Sq Ft
  • $741/SF
  • 88 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1948

  11 Dogwood Ln, Westport, CT 06880

  Experience the best of Westport living in this stunning Mid Century Modern residence set on 1.87 prime acres in the heart of town. This is all about the property! Tucked away on a beautifully landscaped property, this 4-bedroom home offers the perfect blend of privacy, modern design, and everyday convenience. Inside, expansive windows bathe the open living spaces in natural light, with soaring

  Linda Skolnick Coldwell Banker Realty

  11 Dogwood Ln, Westport, CT 06880
• 

  Est $1,540,960 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,419 Sq Ft

  37 Park Ln, Westport, CT 06880

  37 Park Ln, Westport, CT 06880
• 

  

  /40

  $1,550,000

  • 4 Beds
  • 4 Baths
  • 2,484 Sq Ft

  5A Sunrise Rd, Westport, CT 06880

  Discover this stylish contemporary home in Westport's highly desired Saugatuck area - just a 7-minute walk to the train station, making it a commuter's dream. Enjoy being steps from Saugatuck Rowing Club, top restaurants, and the town's most vibrant spots. The open-concept main level features recessed lighting, a living room with fireplace, dining area with deck access, and a modern U-shaped

  Louise Petersen Century 21 AllPoints Realty

  5A Sunrise Rd, Westport, CT 06880
• 

  

  /13

  $10,000 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. Subject to credit report and employment verification; co-signers accepted.

  296 Reef Rd, Fairfield, CT 06824
• 

  $265,000 Sold Nov 05, 2025

  • 931 Sq Ft
  • $285/SF
  • 102 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1905

  96 Davis Ave, Bridgeport, CT 06605

  This property is truly an investor's dream! 96 Davis Avenue is nestled in the very desirable Black Rock section of Bridgeport, CT. Situated perfectly for all that Black Rock has to offer. Within walking distance to the Fairfield Black Rock Train Station or the iconic Saint Mary's by the Sea with beautiful views of Long Island Sound. Just a few minutes' from Elicit Brewery, local shops and

  Bogdan Stefanide KW Legacy Partners

  96 Davis Ave, Bridgeport, CT 06605
• 

  Est $1,478,458 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,283 Sq Ft

  9 Highland Rd, Westport, CT 06880

  9 Highland Rd, Westport, CT 06880
• 

  

  /40

  $2,799,999

  • 5 Beds
  • 6.5 Baths
  • 7,269 Sq Ft

  342 Midlock Rd, Fairfield, CT 06824

  Welcome to an unrivaled sanctuary of sophistication at 342 Midlock Road, gracefully situated in the prestigious enclave of Greenfield Hill. This stately residence, perched on a coveted cul-de-sac off Burr Street, unfurls over two lush acres of meticulously manicured, fully fenced grounds. Upon entry, be enveloped in luxury as you traverse through spaces adorned with custom millwork, nine ft

  AJ Letterman Compass Connecticut, LLC

  342 Midlock Rd, Fairfield, CT 06824
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  /16

  $8,500 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 2,774 Sq Ft
  • Townhouse for Rent

  504 Harvest Commons Unit 504, Westport, CT 06880

  This beautifully renovated townhouse combines effortless one level living with dual primary suites on both the first and second floors. The main level features a chef's kitchen with high-end finishes, an open dining area with room for 6-8 guests and a built-in buffet/bar, plus a welcoming living room with custom built-ins, fireplace, and sliding doors that open to a private bluestone patio. The

  Jessica Kolomondos RE/MAX Heritage

  504 Harvest Commons Unit 504, Westport, CT 06880
• 

  $500,000 Sold Nov 05, 2025

  • 1,282 Sq Ft
  • $390/SF
  • 41 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1951

  143 Sawyer Rd, Fairfield, CT 06824

  Perfect for Fairfield starter or sizing down. Long time owner and very well cared for, requiring no immediate repairs. Great convenient location. Rear deck overlooks level private yard. Exterior maintenance free. Opportunity to customize your remodel and decor. Eat-in kitchen along-side formal dining room. Living room with wood burning fireplace. 3rd bedroom presently used as den.

  Joseph Almeida The Almeida Group

  143 Sawyer Rd, Fairfield, CT 06824
• 

  Est $4,289,145 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 6,112 Sq Ft

  4 Peach Lot Place, Westport, CT 06880

  4 Peach Lot Place, Westport, CT 06880
• 

  

  /39

  $1,100,000

  • 3 Beds
  • 3 Baths
  • 3,670 Sq Ft

  2190 Sturges Hwy, Westport, CT 06880

  Welcome to Pepperidge Acres - a unique enclave of four homes tucked away on a private cul-de-sac ideally located on the Westport line. Conveniently to both Westport & Fairfield town amenities, this classic home sits peacefully on two level acres, offering a serene and picturesque setting. Step into the grand living room featuring a vaulted ceiling and a dramatic floor-to-ceiling, double-sided

  Jeanne Bracken Coldwell Banker Realty

  2190 Sturges Hwy, Westport, CT 06880
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  /9

  $1,950 total monthly price

  • 1 Bed
  • 1 Bath
  • 676 Sq Ft
  • Condo for Rent

  255 Fairfield Woods Rd Unit 2, Fairfield, CT 06825

  255 Fairfield Woods Rd Unit 2, Fairfield, CT 06825
• 

  $3,700,000 Sold Nov 05, 2025

  • 4,856 Sq Ft
  • $762/SF
  • 30 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2018

  254 Penfield Rd, Fairfield, CT 06824

  Rare beach area gem that checks ALL the boxes! With almost 5,000 square feet of living space on a rare and very private .43-acre lot, this highly custom home features a heated saltwater pool, spa/hot tub, 4-floor elevator, and so many high-end amenities. With an exceptionally wide footprint, this home offers 5-6 bedrooms, 4.5 bathrooms, 9-foot ceilings, front and back decks, a full-house

  Ava Fisher Coldwell Banker Realty

  254 Penfield Rd, Fairfield, CT 06824
• 

  Est $2,421,075 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 4,281 Sq Ft

  12 Overlook Rd, Westport, CT 06880

  12 Overlook Rd, Westport, CT 06880
• 

  

  /25

  $270,000

  • 2 Beds
  • 2 Baths
  • 1,096 Sq Ft

  2370 North Ave Unit 3F, Bridgeport, CT 06604

  Enjoy modern comfort and style fully renovated spacious 2-bedroom, 2-bath condominium in desirable Brooklawn at The Regency offers the perfect blend of comfort, style, and convenience, all on one level with elevator access. The open concept living and dining area features high ceilings, an island kitchen with premium appliances, and sliding doors to a large private balcony. Both bedrooms are

  Pilar Camacho Keller Williams Realty Prtnrs.

  2370 North Ave Unit 3F, Bridgeport, CT 06604
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  /12

  $22,500 total monthly price

  • 4 Beds
  • 4 Baths
  • 1,900 Sq Ft
  • House for Rent

  29 Soundview Dr, Westport, CT 06880

  Welcome to Compo Beach, Summer 2026! Charming furnished rental with gorgeous waterviews from almost every room, and your beach is a few steps away. A perfect location with a short walk to Longshore Club with golf and tennis and 3 pools (with Parks and Rec permit). Have lunch or dinner at Rizzuto's at the beach, and then see a play at the famed Westport Country Playhouse. Enjoy all that Westport

  Charlotte Cotton William Raveis Real Estate

  29 Soundview Dr, Westport, CT 06880
• 

  $810,000 Sold Nov 04, 2025

  • 2,267 Sq Ft
  • $357/SF
  • 54 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1977

  1009 High St, Fairfield, CT 06824

  Nestled in the heart of Fairfield's sought after University Neighborhood, this timeless Colonial style home, built in 1977, unfolds across 2,267 sq/ft of thoughtfully arranged living space and features incredible storage areas (including a double car garage with loft!) Four well appointed bedrooms and two and a half baths offer a comfortable sanctuary for homeowners. The primary bedroom also

  Francis O'Driscoll Higgins Group Bedford Square

  1009 High St, Fairfield, CT 06824
• 

  Est $1,032,772 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,348 Sq Ft

  45 Drumlin Rd, Westport, CT 06880

  45 Drumlin Rd, Westport, CT 06880
• 

  

  /37

  $639,900

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  130 Brentwood Ave, Fairfield, CT 06825

  Beautiful 3-bedroom 2.5 bath townhouse with a bonus room, perfect for extra living space or a home office. This home features central air, a gas stove, black stainless steel appliances, a tankless water heater, and beautiful hardwood floors throughout. Enjoy the convenience of a spacious 3-car garage and the benefit of no HOA fees - a fantastic opportunity for comfortable and affordable living!

  Cristina Lu YellowBrick Real Estate LLC

  130 Brentwood Ave, Fairfield, CT 06825
• 

  

  /15

  $2,650 total monthly price

  • 3 Beds
  • 1 Bath
  • 1,482 Sq Ft
  • Condo for Rent

  96 Seaview Terrace Unit 2, Bridgeport, CT 06605

  MOVE RIGHT IN AND ENJOY ALL BLACK ROCK OFFERS FROM YOUR SPACIOUS 3 BEDROOM 2ND FLOOR APARTMENT FEATURING FORMAL DINING ROOM, EAT IN KITCHEN, OFFICE/DEN, PRIVATE REAR DECK AND OFF STREET PARKING. FRESHLY PAINTED, HARDWOOD FLOORING WITH NATURAL SUNLIGHT THROUGHOUT, ALL STEPS TO ST. MARY'S BY THE SEA, ELLSWORTH PARK, HARBORVIEW MARKET, RESTAURANTS/DINING, METRO NORTH TRAIN STATION WITH EASY ACCESS

  96 Seaview Terrace Unit 2, Bridgeport, CT 06605
• 

  $1,600,000 Sold Nov 04, 2025

  • 3,707 Sq Ft
  • $432/SF
  • 140 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1980

  174 Cross Hwy, Westport, CT 06880

  Private getaway just 1 hour from NYC! Bathed in natural light and surrounded by mature landscaping, this 3-bedroom, 3.5 bath contemporary offers a rare blend of privacy, beauty and lifestyle. Set on 2 level acres with an oversized Har-Tru tennis court, the home features an open, airy floor plan with expansive windows that frame the natural surroundings. Vaulted ceilings and generous entertaining

  Emily Gordon Coldwell Banker Realty

  174 Cross Hwy, Westport, CT 06880
• 

  Est $1,711,923 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,450 Sq Ft

  215 Lansdowne, Westport, CT 06880

  215 Lansdowne, Westport, CT 06880
• 

  

  /36

  $7,995,000

  • 5 Beds
  • 7 Baths
  • 4,998 Sq Ft

  775 Sasco Hill Rd, Fairfield, CT 06824

  Exceptional listing at 775 Sasco Hill Road - a home that seamlessly blends timeless elegance with modern luxury. Completely updated and impeccably decorated by the current owners, this residence offers three full levels of sophisticated living. Upon entering, you're greeted by a stunning cathedral ceiling in the foyer, with 9-foot ceilings throughout the main levels that create an airy, open

  Suzy Ryan William Raveis Real Estate

  775 Sasco Hill Rd, Fairfield, CT 06824
• 

  

  /26

  $5,000 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,784 Sq Ft
  • House for Rent

  425 Judd St, Fairfield, CT 06824

  Welcome to your future home in the desirable University Are, an updated raised ranch offering a wonderful blend of style and convenience. The main level showcases hardwood flooring throughout the formal living and dining rooms, along with three bright bedrooms and two full bathrooms. From the kitchen, step directly onto a generously sized deck, perfect for entertaining and summer BBQs. Downstairs

  Karen Cross William Raveis Real Estate

  425 Judd St, Fairfield, CT 06824
• 

  $825,000 Sold Nov 04, 2025

  • 1,344 Sq Ft
  • $614/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1915

  52 Glover St, Fairfield, CT 06824

  Tucked away on a quiet dead-end street in Fairfield's desirable University neighborhood, this classic 3-bedroom, 2-bath Colonial blends comfort, charm, and convenience. Freshly painted interiors and a beautifully landscaped lawn enhance its timeless curb appeal. The inviting main level offers a spacious living area filled with natural light - perfect for relaxing or entertaining. A well-appointed

  Ava Fisher Coldwell Banker Realty

  52 Glover St, Fairfield, CT 06824
• 

  Est $1,229,623 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  205 Lansdowne, Westport, CT 06880

  205 Lansdowne, Westport, CT 06880
• 

  

  /40

  $2,498,000

  • 5 Beds
  • 8 Baths
  • 8,136 Sq Ft

  88 Merry Meet Cir, Fairfield, CT 06824

  Modern elegance meets estate living at 88 Merry Meet Circle, set on 3+ manicured acres in Fairfield's premier gated community, The Ridge. Perfectly positioned where Fairfield meets Westport, this gracious colonial manor offers 5+ bedrooms, 6 full and 2 half baths, and 4 beautifully finished levels-just minutes from vibrant downtowns, beaches, dining, and trains. A grand two-story foyer with a

  Erin Bremen melson The Agency

  88 Merry Meet Cir, Fairfield, CT 06824
• 

  

  /55

  $6,950 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  116 Sherman St, Fairfield, CT 06824

  Embrace the ultimate in sophistication, exclusivity, and style with this stunning two-bedroom, two-bath apartment located in the heart of Downtown Fairfield. With breathtaking panoramic views and an abundance of natural light streaming through a full wall of windows, this home is designed to impress from every angle. Inside, enjoy contemporary features including integrated lighting that creates a

  116 Sherman St, Fairfield, CT 06824
• 

  $2,000,000 Sold Nov 03, 2025

  • 2,856 Sq Ft
  • $700/SF
  • 0 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1934

  5 Maple Grove Ave, Westport, CT 06880

  Beautifully remodeled cape with great curb appeal located on desirable cul-de- sac, walking distance to train, farmer's market , library, town & minutes to beach. Front door opens to spacious entry, that greets one with an amazing open- plan main floor, flooded with light with views of the stunning back yard.The Chef's kitchen has custom cabinetry, floating shelves & professional grade

  Jillian Klaff Coldwell Banker Realty

  5 Maple Grove Ave, Westport, CT 06880
• 

  Est $667,749 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  24 Oakview Cir, Westport, CT 06880

  24 Oakview Cir, Westport, CT 06880

Showing Results 281 - 320, Page 8 of 18