Southport, CT Homes

• 

  

  

  /40

  $9,495,000

  • 6 Beds
  • 11 Baths
  • 11,445 Sq Ft

  5 Hidden Hill Rd, Westport, CT 06880

  Stunning, one-of-one custom home on a private Compo Beach hilltop with sweeping views of Long Island Sound. This Lucien Vita estate was comprehensively refurbished in 2024 to include designer paint treatments, wall coverings, all new lighting and custom window treatments. Luxurious spaces merge impeccable architectural detail and craftsmanship to create distinctive indoor and outdoor living on 4

  Cyd Hamer William Pitt Sotheby's Int'l

  5 Hidden Hill Rd, Westport, CT 06880
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  /3

  $1,775 total monthly price

  • 1 Bed
  • 1 Bath
  • 1,428 Sq Ft
  • Apartment for Rent

  45 Monroe St Unit A4, 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 throughout,

  Tania Pinzon CLS Group

  45 Monroe St Unit A4, Bridgeport, CT 06605
• 

  $760,000 Sold Nov 07, 2025

  • 1,244 Sq Ft
  • $611/SF
  • 27 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1968

  276 Carroll Rd, Fairfield, CT 06824

  Discover this beautifully updated 3 BR ranch home featuring one-level living, situated in one of Fairfield University's most desirable neighborhoods. Nestled on a quiet lot just beneath the bells of the university campus, this home offers breathtaking sunset views. It serves as a tranquil retreat while still being conveniently close to downtown Fairfield, the train station, shops, and

  Helene Daly Compass Connecticut, LLC

  276 Carroll Rd, 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
• 

  

  

  /40

  $2,795,000 Open Sat 9:30AM - 11AM

  • 4 Beds
  • 5 Baths
  • 5,207 Sq Ft

  123 Greens Farms Rd, Westport, CT 06880

  Classic Greens Farms Colonial - Timeless Elegance Meets Modern Comfort ~ Nestled in one of Westport's most desirable neighborhoods, this beautifully updated Center Hall Colonial offers the perfect blend of timeless charm and modern luxury. Ideally located just minutes from Sherwood Island State Park-with its miles of golden sand beaches, scenic picnic areas, and sweeping views-this home provides

  Shalini Madaras Silver Pine Real Estate

  123 Greens Farms 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
• 

  $811,000 Sold Nov 07, 2025

  • 1,440 Sq Ft
  • $563/SF
  • 26 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1943

  46 Middlebrook Dr, Fairfield, CT 06824

  Welcome to the University Area of Fairfiled, CT! This well-maintained three-bedroom, two-bath Colonial is perfectly situated in one of the most sought-after neighborhoods in town. Step inside to find a spacious front-to-back living room, dining room, and updated kitchen with quartz countertops, solid wood cabinets and stainless steel appliances. The large primary bedroom offers ample comfort,

  Tina Ciufo William Raveis Real Estate

  46 Middlebrook Dr, Fairfield, CT 06824
• 

  Est $1,000,791 Not Listed For Sale

  • 4 Beds

  32 Hale St, Westport, CT 06880

  32 Hale St, Westport, CT 06880
• 

  

  /23

  $599,000

  • 3 Beds
  • 1.5 Baths
  • 920 Sq Ft

  9 Crescent Park Rd, Westport, CT 06880

  Welcome to this charming 3-bedroom, 1.5-bath ranch in the heart of Westport - the perfect blend of comfort, convenience, and low-maintenance living. With a brand-new roof and vinyl siding, this home is ready for years of worry-free enjoyment. The inviting living room features a cozy fireplace, creating a warm and welcoming space to relax or entertain. Thoughtfully designed for one-level living,

  Karim Douich William Raveis Real Estate

  9 Crescent Park Rd, Westport, CT 06880
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  /32

  $2,700 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft
  • Apartment for Rent

  2660 North Ave Unit 238, Bridgeport, CT 06604

  (PICTURES WILL BE AVAILABLE SOON) This freshly painted, move-in-ready condo in Bridgeport's desirable North End features 2 full bathrooms and a bright, open-concept layout. The first-floor living room boasts beautiful hardwood floors, while the updated kitchen and spacious bedrooms offer comfort and style. One bedroom includes a bonus 3rd-floor loft-perfect as a home office, playroom, or extra

  Rafael Suarez Yellowbrick Real Estate LLC

  2660 North Ave Unit 238, Bridgeport, CT 06604
• 

  $1,940,000 Sold Nov 06, 2025

  • 4,440 Sq Ft
  • $437/SF
  • 34 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2025

  93 Millspaugh Dr, Fairfield, CT 06824

  **Open house 10/11-10/12 CANCELLED** Absolutely GORGEOUS new construction, /elegantly crafted, that blends modern sophistication with coastal -charm in this 5-BDR, 5 Full Bath home. The main level offers a -balance of open-concept living and defined spaces, featuring 9' ceilings, white oak floors, custom millwork, and curated designer fixtures. The gourmet kitchen is a showstopper, featuring

  Ken Betza Higgins Group Real Estate

  93 Millspaugh Dr, Fairfield, CT 06824
• 

  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
• 

  

  /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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  /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
• 

  $3,100,000 Sold Nov 06, 2025

  • 8,110 Sq Ft
  • $382/SF
  • 63 Days On Market

  • 5 Beds
  • 7 Baths
  • Built 2007

  4 Jennings Ct, Westport, CT 06880

  Tucked away on a sought-after Westport cul-de-sac, this elegant 5-bedroom home offers the perfect blend of luxury, comfort, and convenience. Set on over an acre of beautifully landscaped property, enjoy resort-style living with a stunning gunite pool, private patio, and lush lawn-ideal for summer entertaining or peaceful relaxation. The spacious first-floor primary suite is a true retreat,

  Linda Skolnick Coldwell Banker Realty

  4 Jennings Ct, Westport, CT 06880
• 

  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
• 

  

  /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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  /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 $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
• 

  

  /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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  /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
• 

  $1,175,000 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 $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
• 

  

  /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
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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 $1,032,772 Not Listed For Sale

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

  45 Drumlin Rd, Westport, CT 06880

  45 Drumlin Rd, Westport, CT 06880
• 

  

  /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
• 

  

  /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
• 

  $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 $1,711,923 Not Listed For Sale

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

  215 Lansdowne, Westport, CT 06880

  215 Lansdowne, Westport, CT 06880
• 

  

  /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
• 

  

  /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 $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
• 

  

  /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
• 

  

  /8

  $2,350 total monthly price

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

  15 Welch Terrace, Fairfield, CT 06824

  In Town Location! .... Walk to TRAIN/TOWN/RESTAURANTS... Bike to BEACH... SUNNY & Bright Open Floor Plan ... Spacious Bedroom fit for a King Bed .... Recently Updated .... Gas Heat ..... Hardwood Floors Throughout ... S/S Appliances... Washer/Dryer in Unit ..... Quiet Street .... Private Yard Space .... Storage Area .... Homeowner pays for lawn care/water ....No Pets, No Smoking, Good Credit

  15 Welch Terrace, Fairfield, CT 06824
• 

  $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 $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