Southport, CT Homes for Sale

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  /40

  $4,500,000

  • 5 Beds
  • 4 Baths
  • 4,142 Sq Ft

  1149 Fairfield Beach Rd, Fairfield, CT 06824

  TOES IN THE SAND & SUMMER EVERY DAY. There are waterfront homes-& then there are homes where the water becomes part of everyday life. Welcome to 1149 Fairfield Beach Road, a truly special direct beachfront home appprox 60+/- min from NYC. Thoughtfully designed by a builder for his own family, with an emphasis on capturing the extraordinary waterfront setting. Walls of windows fill the open living

  

  Christine Magliocco

  Higgins Group Real Estate

  1149 Fairfield Beach Rd, Fairfield, CT 06824
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  /37

  $725,000

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,524 Sq Ft

  241 Old Stratfield Rd, Fairfield, CT 06825

  !!!ASSUMABLE 3% VA LOAN - APPROX. $468,000 BALANCE!!! A rare opportunity to secure a substantial portion of your financing at just 3% on this fully renovated Fairfield two-family! Current rents total $4,650/month and are believed to be below market, creating a compelling opportunity for owner-occupants and investors alike. Live in one unit and let the other help offset your housing costs or add a

  

  Andrei Balaj

  Higgins Group Real Estate

  241 Old Stratfield Rd, Fairfield, CT 06825
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  /35

  $329,900

  • 2 Beds
  • 2 Baths
  • 1,145 Sq Ft

  3250 Fairfield Ave Unit 110, Bridgeport, CT 06605

  Cash Sale Only: Easy living in the heart of Black Rock! Tucked into a desirable rear corner of the Village at Black Rock, this 2-bedroom, 2-full-bath condo offers approximately 1,145 square feet of comfortable one-level living with peaceful views overlooking Ash Creek. Step inside and you'll immediately appreciate the bright, open layout where the kitchen, dining, and living spaces come

  

  Alan Stewart Jr.

  ASJ Realty Partners

  3250 Fairfield Ave Unit 110, Bridgeport, CT 06605
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  /36

  $649,000

  • 2 Beds
  • 2.5 Baths
  • 1,731 Sq Ft

  80 Bywater Ln, Bridgeport, CT 06605

  ACT FAST UNIT 54 JUST CLOSED FOR $825K, THIS IS THE BEST VALUE IN BLACK ROCK - Welcome Home to 80 Bywater Lane. Move right into this Voguish, NY chic styled, completely updated townhouse offering 3 spacious levels of comfortable living. Nestled in & surrounded by both nature & seasonal water views. This peaceful home offers total serenity while lounging on 1 of your 3 decks. Featuring 6 generous

  

  Jackie Davis

  William Raveis Real Estate

  80 Bywater Ln, Bridgeport, CT 06605
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  /39

  $4,500,000

  $505K PRICE INCREASE

  • 6 Beds
  • 5.5 Baths
  • 5,682 Sq Ft

  1061 Cedar Rd, Southport, CT 06890

  Tucked behind mature landscaping on a beautifully private 1 acre setting, this extraordinary Southport residence is a home that reveals itself slowly, filled with warmth, character, and timeless craftsmanship. Designed for both everyday living and effortless entertaining, the nearly 6,000 SF home offers 6 bedrooms, 5.5 baths, soaring beamed ceilings, reclaimed wood, antique doors, wide-plank

  

  Libby Tritschler

  William Raveis Real Estate

  1061 Cedar Rd, Southport, CT 06890
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  /36

  $2,885,000

  • 5 Beds
  • 4 Baths
  • 3,255 Sq Ft

  4 Bradley St, Westport, CT 06880

  Just 383 steps from the sands of Compo Beach, this storied 1920s residence claims one of Westport's most sought-after addresses. Approximately 3,255 square feet hold five bedrooms and four baths. An open, updated kitchen with top-tier appliances flows into the living and gathering areas. The primary suite is a generous retreat with vaulted ceilings, a spa bath, and a walk-in closet. Four

  

  Hyleri Katzenberg

  Compass Connecticut, LLC

  4 Bradley St, Westport, CT 06880
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  /40

  $2,549,000

  • 4 Beds
  • 3.5 Baths
  • 5,394 Sq Ft

  3007 Redding Rd, Fairfield, CT 06824

  Gorgeous Farmhouse Colonial tucked away on 2+ picturesque acres & minutes to Fairfield & Westport center. Timeless natural beauty, distinctive architecture, exquisite craftsmanship & sophisticated updates combine to create a home that truly stands apart. Featuring 12 rooms flooded w/ brilliant light over 3 levels of living. Enjoy views of a serene fallow field, a gentle stream, wildlife &

  

  Jackie Davis

  William Raveis Real Estate

  3007 Redding Rd, Fairfield, CT 06824
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  /39

  $1,949,000

  Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,670 Sq Ft

  999 Bronson Rd, Fairfield, CT 06824

  Enchanting Victorian Farmhouse ideally set on 1.25 picturesque acres w/ in-ground heated Pool. Welcome to 999 Bronson Road, where antique living has been remodeled & redesigned eloquently to create a chic modern farmhouse lifestyle. This remarkable historic farmhouse has been lovingly updated while preserving its character & integrity. The inviting wraparound front porch & oversized door greet &

  

  Jackie Davis

  William Raveis Real Estate

  999 Bronson Rd, Fairfield, CT 06824
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  /19

  $1,575,000

  $124K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,450 Sq Ft

  173 Puritan Rd, Fairfield, CT 06824

  Located in the highly desirable beach area of Fairfield, this charming and beautifully maintained 3-bedroom Cape, situated on a corner lot, offers the perfect blend of classic character and modern convenience. The newly remodeled eat-in kitchen features granite countertops and stylish finishes throughout. Enjoy entertaining in the formal dining room with beautiful built-in hutches or relax in the

  

  Glenn Marr

  Marr Caruso Realty Group

  173 Puritan Rd, Fairfield, CT 06824
• 

  

  /40

  $4,500,000

  • 5 Beds
  • 4 Baths
  • 4,142 Sq Ft

  1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824

  TOES IN THE SAND & SUMMER EVERY DAY. There are waterfront homes-& then there are homes where the water becomes part of everyday life. Welcome to 1149 Fairfield Beach Road, a truly special direct beachfront home appprox 60+/- min from NYC. Thoughtfully designed by a builder for his own family, with an emphasis on capturing the extraordinary waterfront setting. Walls of windows fill the open living

  

  Christine Magliocco

  Higgins Group Real Estate

  1149 & 1148 Fairfield Beach Rd, Fairfield, CT 06824
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  /3

  $450,000

  • Land
  • 6,969 Sq Ft
  • $2,812,500 per Acre

  37 Bartram Ave, Bridgeport, CT 06605

  St Mary's by the Sea flat and cleared building lot. Single family and multifamily possible at this location. Beautiful tree lined street close to the water.

  

  David Krasnoff

  Compass Connecticut, LLC

  37 Bartram Ave, Bridgeport, CT 06605
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  /40

  $1,379,000

  • 4 Beds
  • 2 Baths
  • 2,684 Sq Ft

  233 Beaumont St, Fairfield, CT 06824

  Tucked away at the end of in-town Beaumont Street cul-de-sac with unobstructed marsh views and adjacent to a neighborhood park, this home is a rare find in the heart of Fairfield. This beautifully renovated and expanded home offers a rare combination of privacy and convenience. Walk to everything-Fairfield's vibrant town center, train, shops, restaurants and more-then come home to your own

  

  Katie O'Grady

  Compass Connecticut, LLC

  233 Beaumont St, Fairfield, CT 06824
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  /2

  $2,299,000

  • 4 Beds
  • 3.5 Baths
  • 3,800 Sq Ft

  446 Wormwood Rd, Fairfield, CT 06824

  Exceptional New Construction in the University Area. Nestled on a quiet, low-traffic street in the heart of the desirable university neighborhood, this stunning new construction home perfectly blends luxury craftsmanship, modern functionality, and unmatched convenience. Currently under construction with a planned completion for May, this property offers a rare window of opportunity for buyers to

  

  Bette Gigliotti

  William Raveis Real Estate

  446 Wormwood Rd, Fairfield, CT 06824
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  /40

  $7,500,000

  • 5 Beds
  • 9 Baths
  • 11,999 Sq Ft

  541 Sasco Hill Rd, Fairfield, CT 06824

  Prestigious location. Stately presence. Exceptional living. Presenting a Premier 1.25-acre Sasco Hill estate w/ unrivaled luxury across 4 levels of living. This magnificent home features 5 bedrooms, 9 baths & an uncompromised commitment to fine detail. Outside, a private resort awaits featuring a heated pool & spa, a fully equipped outdoor kitchen & an expansive terrace overlooking gorgeous

  

  Jackie Davis

  William Raveis Real Estate

  541 Sasco Hill Rd, Fairfield, CT 06824
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  /37

  $3,400,000

  • 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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  /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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  /19

  $1,799,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,794 Sq Ft

  615 S Pine Creek Rd, Fairfield, CT 06824

  Customize your own beautifully crafted new construction in Fairfield's highly desirable Sasco Hill/South Pine Creek neighborhood, perfectly positioned between town and the beach. Enjoy an exceptional lifestyle just minutes from Pine Creek and Sasco Beaches, Southport Harbor, golf, tennis, the train, and Fairfield's vibrant town center-all within approximately one mile or less. Thoughtfully

  

  Katie O'Grady

  Compass Connecticut, LLC

  615 S Pine Creek Rd, Fairfield, CT 06824
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  /2

  $2,275,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,744 Sq Ft

  75 Spinning Wheel Rd, Fairfield, CT 06824

  Another exceptional new construction by a well-known local builder! Now is the perfect opportunity to meet with the builder and customize this beautifully designed home to suit your lifestyle. Offering approximately 2700 square feet of thoughtfully designed living space, plus additional finished space in the basement, this home features 4 levels of living, 4 spacious bedrooms, and 3.5 luxurious

  

  Bette Gigliotti

  William Raveis Real Estate

  75 Spinning Wheel Rd, Fairfield, CT 06824
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  /35

  $995,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft

  47 Sterling St, Fairfield, CT 06825

  New construction townhome built by a respected local builder known for quality craftsmanship and clean, modern design. This residence offers approximately 2,300 square feet of above-grade living plus a finished lower level, thoughtfully laid out across three levels. The main floor features an open-concept design anchored by a well-appointed kitchen with white and white oak cabinetry, quartz

  Jessica Lane

  Serhant Connecticut, LLC

  47 Sterling St, Fairfield, CT 06825
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  /37

  $2,399,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,950 Sq Ft

  96 Clinton St, Fairfield, CT 06824

  One of only two new construction homes currently available in Fairfield's coveted Beach neighborhood, an incredible opportunity w/ outstanding market value & just steps to the beach - Welcome Home to 96 Clinton Street. 4 levels of living w/ 2950 sf, elevator shaft ready, 4 bedrooms, 3.5 bath & high end finishes throughout. The open concept main level features custom finishes w/ a chef's kitchen

  

  Jackie Davis

  William Raveis Real Estate

  96 Clinton St, Fairfield, CT 06824
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  /19

  $4,250,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 7,499 Sq Ft

  6 Janson Dr, Westport, CT 06880

  Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed

  

  Brett Lieberman

  The Riverside Realty Group

  6 Janson Dr, Westport, CT 06880
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  /17

  $7,926,000

  New Construction

  • 6 Beds
  • 7 Baths
  • 7,200 Sq Ft

  0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880

  Set within Westport's most prestigious private estate enclave, surrounded by grand coastal estates and quintessential antique treasures, this exceptional Greens Farms 2+ acre* new construction offering is poised to become one of Fairfield County's most coveted addresses. Perfectly positioned, moments from beaches, downtown boutiques, vibrant dining scene, and just an express train to Manhattan,

  

  Brett Lieberman

  The Riverside Realty Group

  0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880
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  /32

  $549,000

  • 2 Beds
  • 2 Baths
  • 1,430 Sq Ft

  193 Wilson St, Bridgeport, CT 06605

  Amazing opportunity to own this cute-as-a-button 2-family home in the center of Black Rock! Both 1-bedroom apartments have been thoroughly updated over the years, including kitchen and bath cabinets and countertops, plumbing fixtures, appliances, flooring, recessed lighting, HVAC systems, and landscaping/stonework. The property also includes a private driveway with large gravel area in the rear

  Kaitlyn Walsh William Raveis Real Estate

  193 Wilson St, Bridgeport, CT 06605
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  /31

  $890,000

  • 10 Beds
  • 5 Baths
  • 3,530 Sq Ft

  80-82 Poplar St, Bridgeport, CT 06605

  Exceptional investment opportunity in Bridgeport's desirable Black Rock neighborhood! This well-maintained three-family property offers strong cash flow with a current gross monthly rental income of $8,600, making it an excellent addition to any investor's portfolio or an ideal owner-occupied opportunity. The first and second floor units each feature 3 bedrooms and 1 full bathroom, while the

  Alexia Andrade US Asset Realty

  80-82 Poplar St, Bridgeport, CT 06605
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  /35

  $719,000

  • 5 Beds
  • 3 Baths
  • 3,234 Sq Ft

  244 Bennett St Unit 246, Bridgeport, CT 06605

  Black Rock living at its finest! This pristine 2-family property offers three finished levels that have been thoroughly updated over the years including flooring, kitchen cabinetry, countertops, appliances, bathroom vanities and plumbing fixtures, recessed lighting, sheetrock, trim, HVAC, electrical, and more. Enjoy low maintenance landscaping with crushed stone and mature perennial and evergreen

  Kaitlyn Walsh William Raveis Real Estate

  244 Bennett St Unit 246, Bridgeport, CT 06605
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  /38

  $1,595,000

  • 3 Beds
  • 3.5 Baths
  • 2,650 Sq Ft

  891 Oldfield Rd, Fairfield, CT 06824

  Better than new. Built in 2018 and enhanced with over $175K in recent custom upgrades, this 3-4 bedroom sophisticated three-story residence offers a level of finish, customization and outdoor living rarely found in new construction. Designer interiors feature elevated materials throughout, including a beautifully appointed chef's kitchen and thoughtful custom details. The third-floor flex space

  Mark Ciano Brown Harris Stevens

  891 Oldfield Rd, Fairfield, CT 06824
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  /40

  $1,399,000

  • 4 Beds
  • 4 Baths
  • 4,290 Sq Ft

  694 Jennings Rd, Fairfield, CT 06824

  Exceptional opportunity to own what is essentially a brand-new home in Fairfield University area. Expanded with a full second-story addition and reconstructed from the original foundation up, this remarkable residence offers 3,290 square feet of beautifully finished living space with virtually every major component newly built. Designed for today's lifestyle, the open-concept floor plan features

  Karim Douich William Raveis Real Estate

  694 Jennings Rd, Fairfield, CT 06824
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  /38

  $3,695,000

  • 4 Beds
  • 4.5 Baths
  • 3,744 Sq Ft

  110 Judson Rd, Fairfield, CT 06824

  Nestled on one of Fairfield Beach's most coveted streets, this exceptional new construction blends timeless coastal architecture with sophisticated design in a location that's simply hard to duplicate. Just moments from the beach, town, train, schools, and parks, 110 Judson offers the rare convenience today's buyers seek without sacrificing privacy or tranquility. Thoughtfully positioned at a

  Cindy Raney Coldwell Banker Realty

  110 Judson Rd, Fairfield, CT 06824
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  /39

  $5,495,000

  • 6 Beds
  • 9 Baths
  • 6,561 Sq Ft

  3 Stony Point W, Westport, CT 06880

  Located within the highly desirable Stony Point Association, this exceptional home offers a rare combination of privacy and convenience just moments from the train, local restaurants, and everyday amenities. This particular home enjoys private dock membership, providing summer boat access just steps from your door. Completely transformed and expanded in 2016, the home features over 6,500sf of

  Debra Shaughnessy Coldwell Banker Realty

  3 Stony Point W, Westport, CT 06880
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  /40

  $2,000,000

  Open Sun 11AM - 1PM

  • 4 Beds
  • 4.5 Baths
  • 5,283 Sq Ft

  305 S Gate Ln, Southport, CT 06890

  Set on one of Southport's most coveted streets, this gracious 4 bedroom, 4 bath Colonial offers over 5,200 square feet of finished living space on more than a half acre. Thoughtfully designed for both everyday living and entertaining, the main level features a formal living room and dining room, custom millwork throughout, a spacious eat in kitchen with a dedicated dining area, an inviting family

  Brandy Hall Higgins Group Real Estate

  305 S Gate Ln, Southport, CT 06890
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  /37

  $6,495,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,260 Sq Ft

  16 Westport Ave, Westport, CT 06880

  Experience the future of coastal living in this brand-new smart home located just steps from the sands of Compo Beach. This is the only just-completed residence on the Compo Beach side of Westport delivered as a fully integrated, self-monitoring home: rooftop solar power w/battery storage, intelligent load management, leak detection w/automatic water shutoff, energy-recovery ventilation, radiant

  Karen Scott Compass Connecticut, LLC

  16 Westport Ave, Westport, CT 06880
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  /6

  $455,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,210 Sq Ft

  141 Berwick Ave, Fairfield, CT 06825

  Situated on a quiet dead-end street in the desirable town of Fairfield, this well-maintained 3-bedroom, 2 full-bath single-family home offers comfort, efficiency, and convenience. With approximately 1,200 square feet of living space, the home features a functional layout with bright, inviting rooms throughout. The first-floor living room includes a wood-burning stove, creating a warm and

  Derek Greene Derek Greene

  141 Berwick Ave, Fairfield, CT 06825
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  /31

  $390,000

  • 2 Beds
  • 2.5 Baths
  • 1,410 Sq Ft

  2612 North Ave Unit A6, Bridgeport, CT 06604

  The River's Edge is a gated complex in the Brooklawn Section of Bridgeport, Near the Fairfield town line. Located 1.5 Miles From the Metro Station and also close to I-95. The Two Bedroom Plus Office Space Triplex, Two Full Bathrooms And A Half Bathroom Townhouse Style. There is 5-Closets, Stainless Steel Appliance, And A 2-Car Garage.

  Hakeem Shahid Buyers Capital Brokerage

  2612 North Ave Unit A6, Bridgeport, CT 06604
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  /40

  $8,450,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,893 Sq Ft

  10 Beltas Farm Ln, Westport, CT 06880

  Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling

  Linda Skolnick Coldwell Banker Realty

  10 Beltas Farm Ln, Westport, CT 06880
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  /11

  $669,000

  $120K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,195 Sq Ft

  225 Winnepoge Dr, Fairfield, CT 06825

  Endless opportunities clean up, move in, expand or build your new dream house. Lake Hills Association...enjoy all the beautiful beaches, kayaking, swimming, etc.

  Stacey DiDio Coldwell Banker Realty

  225 Winnepoge Dr, Fairfield, CT 06825
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  /40

  $2,499,000

  $151K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 7,055 Sq Ft

  53 Clinton Ave, Westport, CT 06880

  Incredibly located moments from town and convenient to schools, shopping, commuting options and more, this sparkling home showcases pride of ownership. A new 2026 driveway leads to the landscaped setting, where this gracious home with an in-ground Wagner pool is set amid .74+/- acre. The two-story foyer introduces crisp, timeless spaces, and a home that has been impeccably maintained. The living

  Alex Chingas Coldwell Banker Realty

  53 Clinton Ave, Westport, CT 06880
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  /32

  $1,999,900

  $250K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,381 Sq Ft

  125 Battery Park Dr, Bridgeport, CT 06605

  Perched on a quiet cul-de-sac, this exceptional home offers breathtaking 220-degree panoramic views of Long Island Sound, Black Rock Harbor, and Fayerweather lighthouse. Designed for effortless main-level living, the residence captures stunning water views from the living room, dining room, and luxurious primary bedroom suite. The remodeled primary bath features elegant marble flooring with

  Gail Robinson William Raveis Real Estate

  125 Battery Park Dr, Bridgeport, CT 06605
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  /2

  $950,000

  • 6 Beds
  • 6 Baths
  • 5,304 Sq Ft

  50 Carleton Ave, Bridgeport, CT 06604

  On the market for the first time in nearly 20 years. This legal 6 family is a cash cow with loads of growth potential. Each unit boasts a living room, dining room, eat-in-kitchen, one bedroom and a full bathroom. There is potential to convert each unit into a two bedroom. The property is currently fully occupied, so new owners will have immediate cash flow. The long standing tenants are currently

  Thomas Chanaca Chanaca Real Estate

  50 Carleton Ave, Bridgeport, CT 06604
• 

  

  /25

  $985,000

  • 3 Beds
  • 2 Baths
  • 1,337 Sq Ft

  914 S Pine Creek Rd, Fairfield, CT 06824

  Whether you are seeking a weekend retreat or a year-round residence, this welcoming home is ideal. In the coveted beach area of Fairfield, enjoy the end-of-street beach access, indoor and outdoor tennis, and golf course just moments from your door, with Fairfield Center only a short ride away. A charming 3 bed, 2 full bath Cape Cod with sun-filled spaces throughout. Open floor plan on the main

  Rhoda Yee Berkshire Hathaway NE Prop.

  914 S Pine Creek Rd, Fairfield, CT 06824
• 

  

  /39

  $2,699,000

  $251K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,188 Sq Ft

  1235 Fairfield Beach Rd, Fairfield, CT 06824

  TWO incredible waterside opportunities await! That's right, not one, but TWO fantastic beach area homes are offered! With their direct waterfront locations (1235 - beachfront/LI Sound; 1236 - canal side), both homes have amazing water views, beach access and a convenient, fantastic location all in one! Both homes also offer excellent investment/rental opportunities. #1235 is rented for the

  John Foran Compass Connecticut, LLC

  1235 Fairfield Beach Rd, Fairfield, CT 06824

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