Southport, CT Homes

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  /36

  $3,550,000

  • 6 Beds
  • 6.5 Baths
  • 6,751 Sq Ft

  9 N Ridge Rd, Westport, CT 06880

  In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined

  

  Susan Lieberman

  The Riverside Realty Group

  9 N Ridge Rd, Westport, CT 06880
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  /28

  $17,000 Per Month

  • 6 Beds
  • 6 Baths
  • 5,190 Sq Ft
  • House for Rent

  2 Bluewater Hill S, Westport, CT 06880

  Steps from Compo Beach sits this 5000 Square Foot 6 Bedroom and 6 Bath Home with Water Views from most rooms. Incredible open floor plan with great entertaining spaces inside & out including a fabulous pool with spa. Finished Lower Level with Bed, Bath and Playroom. Term is September 3, 2026 - thru June 10, 2027.THIS IS AN ACADEMIC TERM FURNISHED RENTAL ONLY. Price is per month.

  

  Susan Lieberman

  The Riverside Realty Group

  2 Bluewater Hill S, Westport, CT 06880
• 

  $590,000

  Sold Oct 02, 2025

  293 Barryscott Dr, Fairfield, CT 06825

  • 3 Beds
  • 1.5 Baths
  • 1,412 Sq Ft
  • Built 1953

  Last Sold Summary

  • 12% Above List Price
  • $418/SF
  • 71 Days On Market

  Current Estimated Value $519,709

  Last Listing Agent Stacey DiDio Coldwell Banker Realty

  293 Barryscott Dr, Fairfield, CT 06825
• 

  Est $1,771,080

  Not Listed For Sale

  2 Donald Dr, Westport, CT 06880

  • 4 Beds
  • 2.5 Baths
  • 3,419 Sq Ft
  • Built 1983

  2 Donald Dr, Westport, CT 06880

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent Robert Grodman The Riverside Realty Group
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  /39

  $2,295,000

  $100K PRICE DROP Pending

  • 4 Beds
  • 4.5 Baths
  • 3,978 Sq Ft

  298 S Benson Rd, Fairfield, CT 06824

  Savor the coastal lifestyle in this beautifully designed, light-filled home in Fairfield's sought-after Beach neighborhood. Ideally located just a half-mile stroll from Jennings Beach, Jennings Pavilion, the Fairfield Marina, and Sand Castle park, this home offers the perfect blend of comfort & convenience. The open-concept main level features a spacious living room that flows seamlessly into the

  

  Katie O'Grady

  Compass Connecticut, LLC

  298 S Benson Rd, Fairfield, CT 06824
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  /28

  Starting at $2,487 Plus Fees

  • Studio - 1 Bed

  1177 Post Rd E, Westport, CT 06880

  Suburban comfort mixed with urban convenience. Ideally located north of the Long Island Sound and one hour away from New York, our studio and one-bedroom homes are the perfect place to live and thrive. These Westport, CT, apartments are ready to satisfy all your needs through a wide range of amenities and services. Flexible lease terms are also available!Modern and airy – our residences recreate

  1177 Greens Farms

  

  1177 Post Rd E, Westport, CT 06880
• 

  $642,000

  Sold Apr 17, 2026

  115 King St Unit 117, Bridgeport, CT 06605

  • 4 Beds
  • 2 Baths
  • 2,632 Sq Ft
  • Built 1970

  Last Sold Summary

  • 1% Below List Price
  • $244/SF
  • 44 Days On Market

  Current Estimated Value $512,860

  Last Listing Agent Jeff Romatzick William Raveis Real Estate

  115 King St Unit 117, Bridgeport, CT 06605
• 

  Est $2,393,787

  Not Listed For Sale

  41 Burr Farms Rd, Westport, CT 06880

  • 4 Beds
  • 3.5 Baths
  • 4,753 Sq Ft
  • Built 1954

  41 Burr Farms Rd, Westport, CT 06880

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Meredith Cohen Serhant Connecticut, LLC
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  /22

  $1,175,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft

  119 Old Dam Rd, Fairfield, CT 06824

  Delightful waterfront oasis offering direct access to Long Island Sound and includes deeded Fairfield beach access. This jewel box home has a bright, open floor plan, fully renovated with a coastal style. The kitchen flows seamlessly to the dining area and living room. Glass doors bring the outside in an lead to a spacious deck and property that culminates at the waterfront and dock. The primary

  

  Katie O'Grady

  Compass Connecticut, LLC

  119 Old Dam Rd, Fairfield, CT 06824
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  /38

  $4,400 Per Month

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft
  • House for Rent

  111 Mill Hill Rd, Fairfield, CT 06824

  Nestled on one of Southport's most beloved streets, 111 Mill Hill Road blends classic charm with turnkey comfort. This 3-bed, 2-bath Cape offers ~2,746 sq ft of living space on nearly an acre-so you get room to breathe, entertain, and unwind. The first level features newly finished hardwood floors and a newer kitchen, with updated baths that keep the day-to-day effortless. A flexible main-floor

  

  Alan Stewart Jr.

  ASJ Realty Partners

  111 Mill Hill Rd, Fairfield, CT 06824
• 

  $1,640,000

  Sold Sep 12, 2025

  248 Mayweed Rd, Fairfield, CT 06824

  • 4 Beds
  • 4.5 Baths
  • 4,075 Sq Ft
  • Built 2019

  Last Sold Summary

  • 4% Below List Price
  • $402/SF
  • 49 Days On Market

  Current Estimated Value $1,830,773

  Last Listing Agent Christopher Maroc Coldwell Banker Realty

  248 Mayweed Rd, Fairfield, CT 06824
• 

  Est $2,709,476

  Not Listed For Sale

  38 Tamarac Rd, Westport, CT 06880

  • 5 Beds
  • 4.5 Baths
  • 2,976 Sq Ft
  • Built 1950

  38 Tamarac Rd, Westport, CT 06880

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Jen Kass Higgins Group Bedford Square
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  /37

  $2,395,000

  $100K PRICE DROP Under Contract

  • 6 Beds
  • 5.5 Baths
  • 3,700 Sq Ft

  40 Richmondville Ave, Westport, CT 06880

  Built in 2022, 40 Richmondville Avenue offers generous scale, a thoughtful layout, and true move-in-ready ease. Bright, open-concept main level connects kitchen, dining, and living spaces, with high ceilings and oversized windows throughout. The kitchen features a full Thermador appliance suite, large island with integrated outlets, extensive cabinetry, walk-in pantry, and mudroom with built-ins.

  Jessica Lane

  Serhant Connecticut, LLC

  40 Richmondville Ave, Westport, CT 06880
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  /35

  Starting at $4,991

  Total Monthly Price

  • Studio - 2 Beds

  333 Unquowa Rd, Fairfield, CT 06824

  Built by a team of award-winning architects, designers, and developers, The Anchorage was created to bring a new kind of living to Fairfield—one where you can kick back on a column-lined porch, host an outdoor dinner party, or take a quick drive to a sandy dune-lined beach… and at the end of the day, settle back in a modern luxury apartment community where everything's taken care of.The Anchorage

  The Anchorage

  

  333 Unquowa Rd, Fairfield, CT 06824
• 

  $875,000

  Sold Jan 06, 2026

  162 Country Rd Unit 162, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 2,516 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Above List Price
  • $348/SF
  • 54 Days On Market

  Last Listing Agent Maria Tziolis William Pitt Sotheby's Int'l

  162 Country Rd Unit 162, Fairfield, CT 06824
• 

  Est $1,245,101

  Not Listed For Sale

  23 Hale St, Westport, CT 06880

  • 4 Beds
  • 3 Baths
  • 1,509 Sq Ft
  • Built 1963

  23 Hale St, Westport, CT 06880

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Christy Syrrist Higgins Group Bedford Square
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  /40

  $4,500,000

  $490K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,144 Sq Ft

  1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824

  A rare opportunity to own a premier BEACHFRONT residence offering compelling value in today's luxury market with updated guest home....All BEAUTIFULLY appointed & MOVE IN READY! 60 MINS to NYC! WATERFRONT Home~1149 Walk-Out-To-Sand Waterfront AND Guest Home ~1148 fun & updated (2022) just steps to your Private BEACH. Enjoy true beachfront living w/no steps from your main level family room to an

  

  Christine Magliocco

  Higgins Group Real Estate

  1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824
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  /18

  $3,500 Per Month

  • 2 Beds
  • 1 Bath
  • 2,065 Sq Ft
  • House for Rent

  115 Wilton Rd Unit 1 (front 1st floor), Westport, CT 06880

  Move right into this completely renovated, like-new first-floor 2-bedroom rental in one of Westport's most convenient locations. Every detail has been thoughtfully updated, offering modern finishes, stylish design, and the comfort of an all-new living space. Ideally situated directly across from the picturesque Saugatuck River and just minutes from vibrant Westport Center, shopping, dining, train

  

  Richard Breglia

  Coldwell Banker Realty

  115 Wilton Rd Unit 1 (front 1st floor), Westport, CT 06880
• 

  $3,400,000

  Sold Feb 03, 2026

  1 Boxwood Ln, Westport, CT 06880

  • 5 Beds
  • 8 Baths
  • 7,359 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $462/SF
  • 11 Days On Market

  Last Listing Agent Julie Vanderblue Higgins Group Real Estate

  1 Boxwood Ln, Westport, CT 06880
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  Not Listed For Sale

  1226 Pequot Ave, Southport, CT 06890

  • 4 Beds
  • 4.5 Baths
  • 3,280 Sq Ft
  • Built 1919

  1226 Pequot Ave, Southport, CT 06890

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Michelle Genovesi William Raveis Real Estate
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  /29

  $1,899,000

  • 3 Beds
  • 2.5 Baths
  • 3,338 Sq Ft

  23 Old Dam Rd, Fairfield, CT 06824

  Wonderful waterfront oasis offers direct access to Long Island Sound via a private dock and includes deeded Fairfield beach access. The home features a bright, open floor plan, creating an inviting coastal atmosphere. The primary bedroom boasts a sitting room, a walk-in closet, and a balcony overlooking the waterfront, providing stunning views of LI Sound & Pine Creek. The property promises

  

  Katie O'Grady

  Compass Connecticut, LLC

  23 Old Dam Rd, Fairfield, CT 06824
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  /35

  Starting at $3,400

  Total Monthly Price

  • 1 - 2 Beds

  793 Post Rd E, Westport, CT 06880

  Welcome future Ezra resident! Your carefree modern lifestyle awaits. Elegantly designed and finished high-tech Smart-Townhomes offer the best of every world! These stylish condominium-level finishes boast quartz kitchen islands and upgraded stainless steel appliance packages. Plenty of natural light shines through floor-to-ceiling windows. State-of-the-art Smarthome technology includes full

  The Ezra

  

  793 Post Rd E, Westport, CT 06880
• 

  $750,000

  Sold Jul 31, 2026

  524 Nonopoge Rd, Fairfield, CT 06825

  • 3 Beds
  • 1.5 Baths
  • 1,849 Sq Ft
  • Built 1970

  Last Sold Summary

  • $406/SF
  • 41 Days On Market

  Current Estimated Value $756,197

  Last Listing Agent Judy Mitchell William Pitt Sotheby's Int'l

  524 Nonopoge Rd, Fairfield, CT 06825
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  Est $3,873,272

  Not Listed For Sale

  987 Pequot Ave, Southport, CT 06890

  • 6 Beds
  • 5.5 Baths
  • 5,200 Sq Ft
  • Built 1958

  987 Pequot Ave, Southport, CT 06890

  Last Sold Summary

  • 411 Days On Market

  Last Listing Agent Jaclyn Picarillo Higgins Group Bedford Square
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  /36

  $950,000

  • 3 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  102 Geneva Terrace, Fairfield, CT 06824

  Rare opportunity in Fairfield's highly sought-after Beach Area! This 3-bedroom, 1,400 SF ranch offers an exceptionally rare combination of location, lot, and future potential. Just a short walk to South Pine Creek Beach and only a quarter mile from the prestigious Sasco Hill neighborhood, you'll also enjoy easy access to downtown Fairfield, the train station, restaurants, shops, and beaches.

  

  Judy Szablak

  Coldwell Banker Realty

  102 Geneva Terrace, Fairfield, CT 06824
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  /39

  $11,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • House for Rent

  135 Old Dam Rd, Fairfield, CT 06824

  WATERFRONT PROPERTY ON SOUTH PINE CREEK! This inlet leads to the sound. Nature paths lead to South Pine Creek Beach. Bring your boat and dock it right here. All inclusive rental with landscaping included, plus cleaning service twice a month. Furnished with everything you need including linens if you would like. All utilities included, including internet, electric water, gas, 2 large screen tv's,

  

  Bette Gigliotti

  William Raveis Real Estate

  135 Old Dam Rd, Fairfield, CT 06824
• 

  $1,500,000

  Sold Feb 13, 2026

  101 Brambley Hedge Cir, Fairfield, CT 06824

  • 5 Beds
  • 6 Baths
  • 5,136 Sq Ft
  • Built 1990

  Last Sold Summary

  • 12% Below List Price
  • $292/SF
  • 86 Days On Market

  Current Estimated Value $1,685,888

  Last Listing Agent Akenmisire Musa The Agency

  101 Brambley Hedge Cir, Fairfield, CT 06824
• 

  Est $1,822,522

  Not Listed For Sale

  110 Wellington Dr, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 2,970 Sq Ft
  • Built 1982

  110 Wellington Dr, Fairfield, CT 06824

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Cindy Raney Coldwell Banker Realty
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  /36

  $1,799,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,602 Sq Ft

  114 Lee Dr, Fairfield, CT 06824

  Rare opportunity in Fairfield's sought-after Sasco Hill/South Pine Creek neighborhood, ideally located between town and the beach. Set on a private, level 1/3-acre lot bordering the Sasco Hill estates, this beautifully expanded and renovated home offers stylish finishes and an easy, open layout designed for today's lifestyle. The custom kitchen flows seamlessly into the dining area and inviting

  

  Katie O'Grady

  Compass Connecticut, LLC

  114 Lee Dr, Fairfield, CT 06824
• 

  

  /25

  Starting at $2,425

  Total Monthly Price

  • Studio - 2 Beds

  665 Commerce Dr, Fairfield, CT 06825

  Trademark living is quintessentially connected; adjacent to the Fairfield Metro station,atop a curated collection of shops, and moments from downtown Fairfield's restaurant-lined main street.

  Trademark Fairfield

  

  665 Commerce Dr, Fairfield, CT 06825
• 

  $605,000

  Sold Oct 01, 2025

  261 Colony St, Fairfield, CT 06824

  • 4 Beds
  • 1 Bath
  • 1,446 Sq Ft
  • Built 1936

  Last Sold Summary

  • 1% Above List Price
  • $418/SF
  • 49 Days On Market

  Current Estimated Value $696,394

  Last Listing Agent Christine Howard William Raveis Real Estate

  261 Colony St, Fairfield, CT 06824
• 

  Est $2,704,055

  Not Listed For Sale

  30 Wellington Dr, Fairfield, CT 06824

  • 5 Beds
  • 7 Baths
  • 5,485 Sq Ft
  • Built 2005

  30 Wellington Dr, Fairfield, CT 06824

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent William J. Gill Compass Connecticut, LLC
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  /34

  $1,689,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,138 Sq Ft

  10 Grist Mill Ln, Westport, CT 06880

  Welcome to 10 Grist Mill Lane, a move-in ready home set on a beautiful, level acre at the end of a quiet Long Lots cul-de-sac. Thoughtfully updated throughout, this 3-4 bedroom, 2.5 bath residence offers an open and versatile floor plan designed for today's lifestyle. The dramatic living room features a vaulted ceiling and fireplace, creating a warm and inviting gathering space filled with

  

  Brett Lieberman

  The Riverside Realty Group

  10 Grist Mill Ln, Westport, CT 06880
• 

  

  /10

  $4,250

  Total Monthly Price

  • 4 Beds
  • 2.5 Baths
  • 1,550 Sq Ft
  • Townhouse for Rent

  100 Castle Ave Unit 94, Fairfield, CT 06825

  The 100 Castle Avenue townhomes feature large luxury townhouse style apartments. The newly refinished units are either 3 Bed/ 2.5 Bathroom , or 4 Bed/2.5 Bath, each unit has its own 2 car garage and additional storage space. Each unit features hardwood floors, granite kitchen counter tops, stainless steel kitchen appliances, walk in closets, in-unit washer & dryer, an outside

  100 Castle Ave Unit 94, Fairfield, CT 06825
• 

  $1,100,000

  Sold May 01, 2026

  20 Ermine St, Fairfield, CT 06824

  • 4 Beds
  • 2 Baths
  • 1,925 Sq Ft
  • Built 1950

  Last Sold Summary

  • 45% Below List Price
  • $571/SF
  • 230 Days On Market

  Current Estimated Value $1,221,969

  Last Listing Agent Harriet Stone William Pitt Sotheby's Int'l

  20 Ermine St, Fairfield, CT 06824
• 

  Est $2,448,718

  Not Listed For Sale

  975 Flintlock Rd, Southport, CT 06890

  • 4 Beds
  • 3.5 Baths
  • 4,386 Sq Ft
  • Built 1993

  975 Flintlock Rd, Southport, CT 06890

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Timothy Dailey Higgins Group Real Estate
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  /39

  $4,500,000

  $490K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,144 Sq Ft

  1149 Fairfield Beach Rd, Fairfield, CT 06824

  A rare opportunity to own a premier BEACHFRONT residence offering compelling value in today's luxury market with updated guest home....All BEAUTIFULLY appointed & MOVE IN READY! 60 MINS to NYC! BEACHFRONT Home~1149 Walk-Out-To-Sand Waterfront AND Guest Home ~1148 fun & updated (2022) just steps to your Private BEACH. Enjoy true beachfront living w/no steps from your main level family room to an

  

  Christine Magliocco

  Higgins Group Real Estate

  1149 Fairfield Beach Rd, Fairfield, CT 06824
• 

  

  /35

  Starting at $2,752

  Total Monthly Price

  • 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

  Creekline at Fairfield

  

  219 Ash Creek Blvd, Fairfield, CT 06824
• 

  $3,750,000

  Sold Jun 18, 2026

  312 Compo Rd S, Westport, CT 06880

  • 4 Beds
  • 3.5 Baths
  • 3,215 Sq Ft
  • Built 2012

  Last Sold Summary

  • 7% Above List Price
  • $1,166/SF
  • 12 Days On Market

  Current Estimated Value $3,644,490

  Last Listing Agent Jillian Klaff Coldwell Banker Realty

  312 Compo Rd S, Westport, CT 06880
• 

  Est $2,224,623

  Not Listed For Sale

  1369 S Pine Creek Rd, Fairfield, CT 06824

  • 4 Beds
  • 2.5 Baths
  • 2,521 Sq Ft
  • Built 2025

  1369 S Pine Creek Rd, Fairfield, CT 06824

  Last Sold Summary

  • 141 Days On Market

  Last Listing Agent Veronica Monahan Compass Connecticut, LLC

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