Southport, CT Homes

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  /40

  $639,000

  • 4 Beds
  • 1 Bath
  • 1,760 Sq Ft

  342 Fairfield Woods Rd, Fairfield, CT 06825

  Handyman Special - Huge potential is found at this 4 bedroom Colonial within walking distance to Stratfield Elementary, Owen Fish Park, Fairfield Woods Public Library and shopping conveniences at Stratfield Four Corners. Home needs extensive updates and will be sold in AS IS Condition but is ready for the buyer who has vision to modernize this gem that has been in the same family for over 60

  Kate Meyer William Raveis Real Estate

  342 Fairfield Woods Rd, Fairfield, CT 06825
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  /24

  $2,450 per month

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

  2806 Fairfield Ave Unit 207, Bridgeport, CT 06605

  The Newly Renovated Wanis Building! Spectacular second floor, two bedroom, one bathroom end unit! The unit has 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 restaurant and entertainment district and is convenient to the Black Rock Train

  John Kleps Berkshire Hathaway NE Prop.

  2806 Fairfield Ave Unit 207, Bridgeport, CT 06605
• 

  $2,945,000 Sold Aug 22, 2025

  • 5,454 Sq Ft
  • $540/SF
  • 28 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1958

  41 Cherry Ln, Fairfield, CT 06824

  EXQUISITE COUNTRY COLONIAL - Located on one of the most desirable streets in all of Fairfield County, this absolutely exquisite, breathtakingly beautiful 4760 square foot (additional 700 square feet in the finished Lower Level), 4 Bedroom, three and one-half Bath Colonial features superb, custom millwork, classical architecture and proportions, designer finishes and elements, a stunning Terrace

  Victoria Fingelly Higgins Group Real Estate

  41 Cherry Ln, Fairfield, CT 06824
• 

  Est $1,529,599 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
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  /33

  $689,900

  • 6 Beds
  • 2 Baths
  • 2,441 Sq Ft

  192 Scofield Ave, Bridgeport, CT 06605

  An incredible investment opportunity in the highly desirable Black Rock neighborhood! This well-maintained two-unit multifamily property is perfect for investors or owner-occupants looking to generate rental income. 1st floor apartment features updated kitchen, dining room, living room, 3 bedrooms and 1 full bath. Laundry in unit. 2nd floor apartment features kitchen, dining room, 3/4 bedrooms, 1

  Marissa Papa Preston Gray Real Estate

  192 Scofield Ave, Bridgeport, CT 06605
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  /36

  $13,500 per month

  • 4 Beds
  • 3 Baths
  • 2,542 Sq Ft
  • House for Rent

  660 Penfield Rd, Fairfield, CT 06824

  Steps to miles of sandy beaches, breath taking water views, newly remodeled to perfection, and set on an oversized and level .41 acre lot - 660 Penfield Road is a coastal haven! This spacious 8 room, 4 bedroom, 3 full bath rental has features that make it a stand-out; new hardwood white oak flooring throughout, custom shiplap millwork, 2 fireplaces, multiple decks with water views, an open floor

  Jackie Davis William Raveis Real Estate

  660 Penfield Rd, Fairfield, CT 06824
• 

  $771,000 Sold Aug 22, 2025

  • 2,609 Sq Ft
  • $296/SF
  • 60 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1932

  96 Kenwood Ave, Fairfield, CT 06824

  Fantastic Investment Opportunity on Ash Creek! Beautifully situated on a generous 0.26-acre lot in the desirable B Zone, this 2-family property offers exceptional potential - with room to expand if desired. Enjoy stunning views of Ash Creek from the backyard and select rooms, plus the convenience of 2 detached garages offering a total of 4 bays. Each unit features 2 to 3 bedrooms including a

  Carrie Sakey Coldwell Banker Realty

  96 Kenwood Ave, Fairfield, CT 06824
• 

  Est $4,589,026 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
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  /24

  $109,900

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  221 Alsace St, Bridgeport, CT 06604

  Welcome to this charming 1-bedroom, 1-bathroom co-op, ideally situated just a short walk from the waterfront and beautiful Seaside Park. This move-in ready home offers a bright layout with the convenience of in-unit laundry and plenty of storage. Enjoy peaceful mornings with walks to the park and to the community garden. The community features an enclosed dog run perfect for pet lovers. Whether

  Anthony Fabrizio Coldwell Banker Realty

  221 Alsace St, Bridgeport, CT 06604
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  /15

  $1,900 per month

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

  55 Greenlawn Dr Unit 55, Fairfield, CT 06825

  This meticulously maintained 1st floor ranch unit with private entrance is ready for immediate occupancy. The interior has been freshly painted and is enhanced with oak hardwood floors. Living room w/ entry closet; charming fully-applianced kitchen w/ oak cabinets; 1st floor laundry; bedroom w/ double closet & linen closet; & remodeled bathroom with pedestal sink, bathtub with subway tile

  Joan Hainsworth Berkshire Hathaway NE Prop.

  55 Greenlawn Dr Unit 55, Fairfield, CT 06825
• 

  $1,150,000 Sold Aug 22, 2025

  • 3,937 Sq Ft
  • $292/SF
  • 46 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1997

  26 Hamilton Ct Unit 26, Fairfield, CT 06824

  Greenfield Hunt is a unique community of 100 single family homes set on 56 lush acres surrounded by nature and anchored by a sparkling swimming pool. This beautifully maintained & perfectly laid out house on a quiet cul de sac, features a welcoming foyer, large Eat In Kitchen w/center island, granite counters, Brazilian hardwood flooring, lots of cabinetry w/custom storage and an eating area

  Rita Tanis Berkshire Hathaway NE Prop.

  26 Hamilton Ct Unit 26, Fairfield, CT 06824
• 

  Est $3,346,582 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,367 Sq Ft

  42 Danbury Ave, Westport, CT 06880

  42 Danbury Ave, Westport, CT 06880
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  /40

  $1,545,000

  • 4 Beds
  • 2.5 Baths
  • 3,597 Sq Ft

  153 Pease Ave, Southport, CT 06890

  Newly Renovated Colonial in Prime Southport Location. Beautifully updated colonial offering modern comfort and timeless style. Featuring a stunning new custom kitchen with a large center island, professional Thermador appliances, and separate butlers pantry, this home is perfect for both everyday living and entertaining. The open floor plan is filled with natural light and has 9ft ceilings

  Basil Amso RE/MAX Right Choice

  153 Pease Ave, Southport, CT 06890
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  /9

  $2,700 per month

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft
  • Apartment for Rent

  255 Jennings Rd Unit 257, Fairfield, CT 06825

  Bright and airy second-floor unit with 6 Rooms | 3-Bedrooms - Prime Fairfield Location! featuring an open-concept kitchen, dining, and living area that opens to a newly constructed private deck with slider door access, perfect for outdoor enjoyment. Freshly painted throughout, this home boasts beautiful hardwood floors, three generous-sized bedrooms, plenty of natural light. Ideally located just

  Karim Douich CT Asset Realty LLC

  255 Jennings Rd Unit 257, Fairfield, CT 06825
• 

  $925,000 Sold Aug 22, 2025

  • 4,602 Sq Ft
  • $201/SF
  • 46 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1949

  440 Hilltop Rd, Bridgeport, CT 06605

  Located up on the top of the "hill" and only steps to the most picturesque walking park along the Connecticut coast (St. Mary's By The Sea which follows along the coast of the very desirable Black Rock section of Bridgeport, CT) - sits an incredibly special home and property with seasonal water views *that is not only livable as is, but most certainly offers endless opportunities to create

  Christi McEldowney William Raveis Real Estate

  440 Hilltop Rd, Bridgeport, CT 06605
• 

  Est $1,645,039 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,759 Sq Ft

  8 Ridge Dr, Westport, CT 06880

  8 Ridge Dr, Westport, CT 06880
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  /38

  $1,345,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 3,360 Sq Ft

  545 Surrey Ln, Fairfield, CT 06824

  Classic four bedroom, 2.5 bath colonial strikes a rare balance, offering turnkey charm, space and modern updates on a superb, manicured acre - all within one of Fairfield's most coveted neighborhoods. Set on a quiet tree-lined street in lower Greenfield Hill with a new roof, newer windows and air conditioner paired with fresh paint ensures lasting curb appeal and peace of mind. The well-appointed

  Kelly Finn Coldwell Banker Realty

  545 Surrey Ln, Fairfield, CT 06824
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  /12

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • House for Rent

  20 Hulls Hwy Unit 20, Southport, CT 06890

  This unit is located very conveniently in Southport. Newly renovated, this first floor unit is one of the only units in the complex with its own garage which is included in the monthly rent. This unit spares no expense, a wood burning fireplace and a screened in porch overlooking the lawn is perfect for summer and winter days and nights. Speaking of summer, residents will enjoy the Quincy complex

  Jen Kass Higgins Group Bedford Square

  20 Hulls Hwy Unit 20, Southport, CT 06890
• 

  $1,132,500 Sold Aug 22, 2025

  • 3,656 Sq Ft
  • $310/SF
  • 53 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1917

  399 N Benson Rd, Fairfield, CT 06824

  This elegant Dutch Colonial, built in 1917, sits 150 feet off the road providing serene privacy & picturesque surroundings. Situated in Fairfield's University area, a short walk to the train, town, public schools, and Fairfield University. Loved by only three owners, this home boasts exquisite craftsmanship: carved fireplace mantels w/dental moldings, plate rails, pocket doors, hardwood floors

  Nannette Fatigate Berkshire Hathaway NE Prop.

  399 N Benson Rd, Fairfield, CT 06824
• 

  Est $2,324,655 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
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  /38

  $739,900

  • 4 Beds
  • 3.5 Baths
  • 2,268 Sq Ft

  42 Fairway Green, Fairfield, CT 06825

  Charming and Fresh-Painted Colonial with Modern Upgrades. This freshly painted colonial home boasts 4 spacious bedrooms, 3.5 baths, a brand-new HVAC system, and a wood-burning fireplace. With 2268 sq ft of living space plus a 520 sq ft finished basement, it includes a large deck, an office or in-law suite and a tall 2-car garage. Built in 1987 on a 0.24-acre lot, this home is in a

  David White OwnerEntry.com

  42 Fairway Green, Fairfield, CT 06825
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  /31

  $4,500 per month

  • 2 Beds
  • 1.5 Baths
  • 1,048 Sq Ft
  • House for Rent

  132 Pequot Ave, Southport, CT 06890

  LOCATION, LOCATION, LOCATION! AMAZING RENTAL OPPORTUNITY for downsizers, commuters, or anyone seeking a condo alternative! This enchanting, completely renovated and move-in ready Farmhouse, perched gracefully atop a hill, offers rare privacy and unbeatable convenience-just steps from Southport Harbor, beaches, village shops, restaurants, and the Metro-North train. Location, charm, and

  Jackie Davis William Raveis Real Estate

  132 Pequot Ave, Southport, CT 06890
• 

  $1,102,500 Sold Aug 22, 2025

  • 2,538 Sq Ft
  • $434/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1929

  344 Lake Ave, Bridgeport, CT 06605

  Your dream home awaits at 344 Lake Avenue, ideally located on one of Black Rock's most beloved and sought-after streets. This fully reimagined and beautifully updated Colonial blends timeless charm with modern design for effortless, stylish living. Step into a stunning chef's kitchen with dual islands, leathered and honed granite counters, sleek custom cabinetry, and premium appliances. The

  Amy Desel Compass Connecticut, LLC

  344 Lake Ave, Bridgeport, CT 06605
• 

  Est $562,989 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 760 Sq Ft

  70 Whitney Glen, Westport, CT 06880

  70 Whitney Glen, Westport, CT 06880
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  /40

  $1,545,000 Open Sat 11AM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,416 Sq Ft

  785 Post Rd E Unit 201, Westport, CT 06880

  AMAZING NEW CONSTRUCTION! Located in the heart of Westport, The Gables of Westport presents a collection of eight townhomes and five flats, blending sophisticated design with the ease of in-town living. Enjoy close proximity to Metro-North, major highways, Longshore Club & Park, Compo Beach, Levitt Pavilion, Westport Country Playhouse, fine dining, shopping, and entertainment. Crafted by local

  Todd Gibbons Boost Real Estate Group

  785 Post Rd E Unit 201, Westport, CT 06880
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  /24

  $2,100 per month

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

  124 Thorpe St, Fairfield, CT 06824

  This in-town rental offers the perfect blend of comfort and convenience, ideally located in the heart of one of the best downtown areas around. Just a short walk to the train, shops, and restaurants, and only minutes from I-95 and the Merritt Parkway, it's a commuter's dream. The second-floor unit features two spacious bedrooms, one full bathroom, and an eat-in kitchen. There's also a small bonus

  Denise Napoleone William Raveis Real Estate

  124 Thorpe St, Fairfield, CT 06824
• 

  $1,875,000 Sold Aug 22, 2025

  • 5,737 Sq Ft
  • $327/SF
  • 161 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1993

  215 Paddock Hill Ln, Fairfield, CT 06824

  Paddock Hill Manor is a stunning French Colonial home on 2.03 lush-green acres in the area's pre-eminent gated community, The Ridge. Majestically located on a quiet cul-de-sac steps from Patterson Country Club Golf C. The home blends grandeur and sophistication for entertaining and daily living. Natural light floods the newly painted interiors and refinished hardwood flrs. The grand two-story

  Sholeh Janati Weinbaum Higgins Group Bedford Square

  215 Paddock Hill Ln, Fairfield, CT 06824
• 

  Est $1,632,101 Not Listed For Sale

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

  215 Lansdowne, Westport, CT 06880

  215 Lansdowne, Westport, CT 06880
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  /39

  $1,390,000 Open Sat 11AM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,416 Sq Ft

  785 Post Rd E Unit 203, Westport, CT 06880

  AMAZING NEW CONSTRUCTION! Located in the heart of Westport, The Gables of Westport presents a collection of eight townhomes and five flats, blending sophisticated design with the ease of in-town living. Enjoy close proximity to Metro-North, major highways, Longshore Club & Park, Compo Beach, Levitt Pavilion, Westport Country Playhouse, fine dining, shopping, and entertainment. Crafted by local

  Todd Gibbons Boost Real Estate Group

  785 Post Rd E Unit 203, Westport, CT 06880
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  /30

  $9,500 per month

  • 4 Beds
  • 2 Baths
  • 1,107 Sq Ft
  • House for Rent

  22 Oldfield Dr, Fairfield, CT 06824

  ACADEMIC 2028-2029 ONLY. Luxury rental fully furnished situated south of the Post Rd. between two of the most coveted beaches in Fairfield. Large kitchen with 5 seat island, GE Cafe appliances and quartz countertops opens up into the living room with hardwood floors throughout. Outside offers a rear private patio accompanied by a completely level and fully fenced in yard and grill. Less than 5

  Ryan Ciambriello Houlihan Lawrence

  22 Oldfield Dr, Fairfield, CT 06824
• 

  $1,250,000 Sold Aug 21, 2025

  • 1,980 Sq Ft
  • $631/SF
  • 15 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1938

  204 Eastlawn St, Fairfield, CT 06824

  LOCATION, LOCATION, LOCATION! Welcome to 204 Eastlawn Street! This beautiful 4 bedroom, 3 bath Colonial is located in one of the most popular neighborhoods in the Beach Area. The spacious first level offers a bright and open layout, perfect for both everyday living and entertaining. Relax in the living room with a fireplace or gather in the open-concept kitchen that flows seamlessly into the

  Eileen Brown William Raveis Real Estate

  204 Eastlawn St, Fairfield, CT 06824
• 

  Est $1,220,730 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,875 Sq Ft

  208 Lansdowne, Westport, CT 06880

  208 Lansdowne, Westport, CT 06880
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  /37

  $4,249,000

  • 5 Beds
  • 5 Baths
  • 3,390 Sq Ft

  179 Compo Rd S, Westport, CT 06880

  Welcome to 179 Compo Road South, in the heart of Westport-super close to Longshore, Compo Beach, downtown, the train station-everything Westport has to offer. This Tudor-style gem, originally built in the 1920s, has been thoroughly renovated to honor its heritage while offering every contemporary comfort. Situated high on the hillside, sweeping property views enchant. The classic slate roof is

  Judy Michaelis Coldwell Banker Realty

  179 Compo Rd S, Westport, CT 06880
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  /26

  $7,500 per month

  • 3 Beds
  • 2 Baths
  • 1,348 Sq Ft
  • House for Rent

  45 Drumlin Rd, Westport, CT 06880

  Yearly unfurnished rental in a "walk to Compo Beach" neighborhood. This fully renovated home lives big with 3 bedrooms plus 2 full baths, a family room with fireplace, and an office/den w French doors to a private patio. The dining room, with built -in glass hutch, is large for entertaining or every day dining -right off the kitchen. The kitchen has granite surfaces and handsome stainless steel

  Sally Bohling Coldwell Banker Realty

  45 Drumlin Rd, Westport, CT 06880
• 

  $430,000 Sold Aug 21, 2025

  • 902 Sq Ft
  • $477/SF
  • 12 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1964

  245 Unquowa Rd Unit 35, Fairfield, CT 06824

  DOWNTOWN FAIRFIELD LIVING - STEPS FROM TRAIN & EVERYTHING! Prime location just steps from Fairfield Center Train Station and all downtown shops, dining, and entertainment! This stunning first-floor end unit offers spacious comfort with seamless living/dining flow, large kitchen with pantry, updated bathroom, and oversized primary bedroom with walk-in closet. In-unit laundry plus commercial

  Mark Pires Coldwell Banker Realty

  245 Unquowa Rd Unit 35, Fairfield, CT 06824
• 

  Est $1,321,659 Not Listed For Sale

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

  205 Lansdowne, Westport, CT 06880

  205 Lansdowne, Westport, CT 06880
• 

  

  /40

  $1,495,000 Open Sat 11AM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,416 Sq Ft

  785 Post Rd E Unit 102, Westport, CT 06880

  AMAZING NEW CONSTRUCTION! Located in the heart of Westport, The Gables of Westport presents a collection of eight townhomes and five flats, blending sophisticated design with the ease of in-town living. Enjoy close proximity to Metro-North, major highways, Longshore Club & Park, Compo Beach, Levitt Pavilion, Westport Country Playhouse, fine dining, shopping, and entertainment. Crafted by local

  Todd Gibbons Boost Real Estate Group

  785 Post Rd E Unit 102, Westport, CT 06880
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  /7

  $2,950 per month

  • 1 Bed
  • 1 Bath
  • 11,207 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
• 

  $3,100,000 Sold Aug 21, 2025

  • 3,495 Sq Ft
  • $887/SF
  • 11 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1946

  19 Old Hill Rd, Westport, CT 06880

  Step into a home where every detail tells a story of timeless elegance and masterful transformation. This 4-bedroom, 3-bath Colonial-reimagined through a multi-year, designer-led renovation-seamlessly marries historic charm with modern sophistication. Original Southern Pine floors and exposed beams ground the home in authenticity, while a stunning new kitchen by Shore & Country elevates everyday

  Cindy Raney Coldwell Banker Realty

  19 Old Hill Rd, Westport, CT 06880
• 

  Est $655,145 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 321 - 360, Page 9 of 18