Southport, CT Homes for Sale

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  /17

  $185,000 Coming Soon

  • 1 Bed
  • 1 Bath
  • 939 Sq Ft

  25 Cartright St Unit 3K, Bridgeport, CT 06604

  Enjoy easy one-level living in this spacious and sun-filled large 1 bedroom condo, ideally located on the 3rd floor of an elevator building. This move-in-ready and freshly painted bright unit features a oversized screened terrace overlooking a peaceful garden area-perfect for relaxing or entertaining. Inside, you'll find a large living room and dining area, a generously-sized kitchen with newer

  Ellen Fusco Compass Connecticut, LLC

  25 Cartright St Unit 3K, Bridgeport, CT 06604
• 

  

  

  /40

  $4,150,000 New Construction

  • 7 Beds
  • 7.5 Baths
  • 6,679 Sq Ft

  102 Compo Rd S, Westport, CT 06880

  THE ESTATES AT COMPO SOUTH - SIR Development presents the last of two luxury residences set back on beautiful property, each with their own distinct Modern style and pool. Officially designated by the State of CT as a Scenic Roadway, this location offers ultimate convenience to every amenity that makes Westport one of the most highly desired towns in the nation. This elevator-ready home begins

  Doug Bross Coldwell Banker Realty

  102 Compo Rd S, Westport, CT 06880
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  /40

  $4,585,000

  • 7 Beds
  • 10 Baths
  • 7,933 Sq Ft

  282 North Ave, Westport, CT 06880

  Welcome to 282 North Avenue, a timeless Westport residence set on a beautifully landscaped parcel in one of the town's most desirable locations. This inviting home blends classic New England charm with modern comfort, offering bright, well-proportioned living spaces designed for both everyday living and entertaining. Sun-filled interiors feature hardwood floors, oversized windows, and a flowing

  Thomas Mele Dorrance Realty

  282 North Ave, Westport, CT 06880
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  /35

  $689,900

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft

  250 Szost Dr, Fairfield, CT 06824

  Well-maintained and ideally located in a convenient University Area setting, this inviting 3-bedroom home offers a functional layout and comfortable living spaces throughout. The main level features a bright living room with hardwood floors, a dining room with hardwood floors and a sliding glass door leading to the deck, and a kitchen with a dedicated eating area, perfect for everyday living and

  Steven Lage Coldwell Banker Realty

  250 Szost Dr, Fairfield, CT 06824
• 

  

  

  /40

  $949,000 Open Thu 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,956 Sq Ft

  1478 Jennings Rd, Fairfield, CT 06824

  Private, peaceful, and perfectly located, this University-area home offers a serene natural setting just minutes from Fairfield's town center, train, and beaches. Set in Fairfield's highly sought-after University area, this beautifully updated 3-bedroom, 2.5-bath home offers two levels of living with a cozy fireplace and a rare connection to nature. Surrounded by mature trees, stone walls, a

  Michael Jabick Keller Williams Realty

  1478 Jennings Rd, Fairfield, CT 06824
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  /35

  $1,299,000

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

  12 Sugar Plum Ln, Fairfield, CT 06824

  Coming Soon! This stunning 4-bedroom, 4-full-bath Contemporary Modern Colonial-style home has been fully rebuilt from the foundation up and offers the perfect blend of modern luxury and thoughtful design. The bright open-concept main level features a designer kitchen equipped with Thermador appliances, quartz countertops, and an oversized island that flows seamlessly into the spacious and

  Karim Douich William Raveis Real Estate

  12 Sugar Plum Ln, Fairfield, CT 06824
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  /34

  $2,450,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 4 Baths
  • 3,218 Sq Ft

  86 Maple Ave S, Westport, CT 06880

  Renovated, refreshed, and move-in ready, this sunfilled Greens Farms gem offers the perfect blend of charm, style, and modern comfort. Set on a beautifully landscaped, level acre with gunite pool and expansive patio, the outdoor living experience is exceptional. Fresh paint inside and out, a new pergola, and thoughtful landscaping create irresistible curb appeal. Step inside and feel instantly at

  Jaclyn Picarillo Higgins Group Bedford Square

  86 Maple Ave S, Westport, CT 06880
• 

  

  /14

  $1,475,000

  • Land
  • 1.05 Acres
  • $1,404,762 per Acre

  50 Sylvan Rd N, Westport, CT 06880

  DREAM YOUR TOMORROW This 1.05 acre of dry, level land that is available for sale, is beautifully sited in the middle of Westport's Old Hill and awaits your imagination. Enter through the original gates of the 1928 Arthur Whiteside Estate at 50 Sylvan North --- the park-like entry to the 25-acre estate built for Whiteside, who founded and headed the commercial credit rating firm of Dun &

  Martha Eidman Coldwell Banker Realty

  50 Sylvan Rd N, Westport, CT 06880
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  /40

  $5,200,000

  • 6 Beds
  • 12 Baths
  • 13,979 Sq Ft

  2959 Congress St, Fairfield, CT 06824

  Prepare to be wowed by this extraordinary estate featuring six bedrooms and ten-and-a-half bathrooms, spanning four meticulously designed floors. Enter through a breathtaking two-story grand foyer, leading into beautifully appointed formal and informal rooms perfect for entertaining and a gourmet kitchen that any discerning chef would envy. The luxurious primary suite serves as a private retreat,

  Anissa Paolillo Redfin Corporation

  2959 Congress St, Fairfield, CT 06824
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  /32

  $2,399,000

  • 3 Beds
  • 3.5 Baths
  • 3,328 Sq Ft

  2 Elmwood Dr Unit 2, Southport, CT 06890

  Rare opportunity in sought-after Southport Green-just steps to Southport Village and Metro-North. One of only two stand-alone residences in this 24-unit enclave, this home offers the privacy of a single-family lifestyle with the ease of condominium living. The townhouse-style residence spans three levels and features 3 bedrooms, 3 renovated full and 1 half baths, plus a coveted attached two-car

  Wendy Ryan Brown Harris Stevens

  2 Elmwood Dr Unit 2, Southport, CT 06890
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  /40

  $5,500,000

  • 5 Beds
  • 7 Baths
  • 5,198 Sq Ft

  1410 S Pine Creek Rd, Fairfield, CT 06824

  Imagine starting each day with breathtaking sunrises over the water, the salty breeze on your face, and your toes in the sand. This magnificent custom-built waterfront estate offers 126 feet of direct beachfront along Fairfield's highly sought-after South Pine Creek Beach Area. Perfectly situated on nearly an acre of property, this stately Federal Colonial was custom built in 2005 and showcases

  Melissa Montagno Higgins Group Real Estate

  1410 S Pine Creek Rd, Fairfield, CT 06824
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  /37

  $999,999

  • 2 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  972 S Pine Creek Rd, Fairfield, CT 06824

  Nestled in a serene, beautifully landscaped community, this gracious townhouse at Pine Ridge offers the perfect blend of privacy and lifestyle. Set around a center green and gazebo, it creates a tranquil and inviting atmosphere. Located within a short walk to the beach, par 3 golf and tennis center. The bright and spacious living room, perfect for entertaining, has nine foot ceilings, a

  Harriet Stone William Pitt Sotheby's Int'l

  972 S Pine Creek Rd, Fairfield, CT 06824
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  /37

  $4,299,000 Open Thu 12PM - 2PM

  • 5 Beds
  • 7 Baths
  • 7,409 Sq Ft

  13 Rockyfield Rd, Westport, CT 06880

  Your staycation starts here. Pristine 2006 Colonial delivering timeless Westport luxury and effortless living, set on 1.12 flat, manicured acres with stone walls in a coveted, quiet neighborhood just one hour from NYC. This five-bedroom home offers five full and two half baths, two dedicated offices, and two flexible bonus spaces-ideal for today's work-from-home, wellness, and entertaining

  Danna Rogers Higgins Group Bedford Square

  13 Rockyfield Rd, Westport, CT 06880
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  /40

  $5,800,000

  • 4 Beds
  • 5 Baths
  • 7,105 Sq Ft

  80 Compo Rd N, Westport, CT 06880

  Set on a private, in-town 1.5-acre parcel, this custom shingle-style home offers refined design and exceptional craftsmanship throughout. Thoughtfully sited to capture southern, western, and eastern exposures, the home captures natural light from sunrise to sunset. Architectural highlights include intricate millwork, wide oak-plank flooring, dramatic ceilings, arched doorways, and extensive

  Adrienne Durkin Compass Connecticut, LLC

  80 Compo Rd N, Westport, CT 06880
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  /39

  $2,200,000

  • 6 Beds
  • 2 Baths
  • 2,180 Sq Ft

  2142 Fairfield Beach Rd, Fairfield, CT 06824

  OPPORTUNITY KNOCKS TWICE - A unique investment awaits with the only two-family home on the Fairfield Beach Road Peninsula featuring private beach access. This fully furnished property offers excellent rental income during the academic season and serves as a relaxing summer retreat for owners-or an additional rental opportunity. Unit 2142 is a spacious four-bedroom residence, each room furnished

  Michael Menillo Collage Realty

  2142 Fairfield Beach Rd, Fairfield, CT 06824
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  /18

  $9,995,000 New Construction

  • 7 Beds
  • 10 Baths
  • 10,800 Sq Ft

  688 Hulls Farm Rd, Southport, CT 06890

  This is the iconic property everyone is talking about! Introducing an extraordinary new custom residence set in the beloved estate area of Upper Southport near private equestrian facilities and public trails, beaches, restaurants, train, and shopping. Masterfully designed and customized to YOUR every whim with exquisite main house, separate party barn and/or guest house, pool with spa, tennis

  Jaclyn Picarillo Higgins Group Bedford Square

  688 Hulls Farm Rd, Southport, CT 06890
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  /40

  $1,999,000

  • 4 Beds
  • 4 Baths
  • 4,152 Sq Ft

  218 Lower Farm Rd, Fairfield, CT 06824

  Highest and Best Bid Deadline Sunday, Feb. 1, by 9:00 pm. Offers will be reviewed on Monday, Feb. 2nd. New construction, Light, bright, sunny, pristine 4/5 bedroom, 4 full bath colonial built in 2025 on a beautiful cul-de-sac enclave of 7 new homes meticulously constructed by Sanddollar Development, known for their stellar designs, quality materials and next-level craftsmanship. Luxurious

  Cindy Searight Compass Connecticut, LLC

  218 Lower Farm Rd, Fairfield, CT 06824
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  /40

  $1,049,000 Open Thu 1:30PM - 3:30PM

  • 3 Beds
  • 2.5 Baths
  • 1,819 Sq Ft

  25 Maplewood Ave, Westport, CT 06880

  LOVE IT TODAY AND DREAM YOUR TOMORROW! WOW!!! This light-filled cozy cape with 1800sf living space on 3-levels, 3-bedrooms and 2-1/2 baths (this includes the legal accessory apt with a separate kitchen, 1 bedroom and 1 bath) is INDEED A RARE FIND in its sought-after neighborhood --- and yields so much flexibility for the new owner to supplement income as needed! Where else in town do you have a

  Martha Eidman Coldwell Banker Realty

  25 Maplewood Ave, Westport, CT 06880
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  /29

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 1,406 Sq Ft

  97 Fayerweather Terrace, Bridgeport, CT 06605

  Fabulous Remodeled 4 Bedroom main house with Open floor plan. Partially finished basement. New Energy Star Appliances, Solar and beautifully appointed. Detached 2 Car Garage with One bedroom one bath unit above. Close to train, restaurants, St. Mary's by the Sea.

  Steven Koleno Beycome of Connecticut

  97 Fayerweather Terrace, Bridgeport, CT 06605
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  /14

  $149,900

  • 1 Bath
  • 629 Sq Ft

  80 Cartright St Unit 8B, Bridgeport, CT 06604

  Discover a rare opportunity to own a beautifully updated studio unit in Cartright Towers, a well-maintained building on the Fairfield/Bridgeport line. Whether you're an investor seeking strong rental potential or a buyer looking for a move-in ready home, this immaculate unit checks every box. Enjoy the convenience and security of full-time doorman service, plus amenities including elevators,

  Hillary Waite William Raveis Real Estate

  80 Cartright St Unit 8B, Bridgeport, CT 06604
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  /15

  $5,472,860 New Construction

  • 7 Beds
  • 8 Baths
  • 6,660 Sq Ft

  1 Sturges Hwy Unit 2, Westport, CT 06880

  Design Your Dream Home with an Award-Winning Builder Step into a world of elegance and sophistication with a soon-to-be-built 6,100 sq. ft. masterpiece by Coastal Luxury Homes. Known for their innovative designs, sleek modern lines, and unparalleled craftsmanship, Coastal Luxury Homes has earned a reputation for creating some of the most sought-after residences. With a focus on prime location,

  Annie Klyver Higgins Group Real Estate

  1 Sturges Hwy Unit 2, Westport, CT 06880
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  /40

  $4,899,000 Open Sat 1PM - 4PM

  • 5 Beds
  • 8 Baths
  • 7,400 Sq Ft

  10 Tierney Ln, Westport, CT 06880

  This is the second of 2 custom homes, beautifully sited at the end of a private lane in the heart of Greens Farms. Combining classic design with modern detailing by an established local builder of premier residences, this masterfully crafted home is sure to delight even the most discerning buyer. The main level showcases expert millwork and warm white oak accents throughout, flowing from the

  Laurie Crouse Coldwell Banker Realty

  10 Tierney Ln, Westport, CT 06880
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  /21

  $885,000

  • 3 Beds
  • 3 Baths
  • 1,930 Sq Ft

  35 Knapps Hwy, Fairfield, CT 06825

  Welcome home to this beautifully remodeled cape which boasts 3 bedrooms, 3 full bathrooms, walk-in closets, stainless steel appliances, a finished lower level, a sun room and much more! The new, efficient mechanicals really keep energy costs down. The home is close to parks, shopping, golf, tennis courts, Fairfield's excellent schools and has a private, fenced back yard. There is plenty of

  Thomas Chanaca Chanaca Real Estate

  35 Knapps Hwy, Fairfield, CT 06825
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  /40

  $900,000

  • 5 Beds
  • 4 Baths
  • 2,192 Sq Ft

  489 Main St, Westport, CT 06880

  Single Family with legal accessory apartment. New 5 bedroom septic system- just installed and new furnace and hot water heater in apartment. Let your imagination soar in creating your ideal situation. The main house and the accessory apartment each has a fireplace, The main house has 3 bedrooms and the apartment 2 bedrooms and each has 2 full baths. Hardwood Floors, laminate floor, vinyl floor,

  Gabrielle DiBianco Higgins Group Bedford Square

  489 Main St, Westport, CT 06880
• 

  

  /23

  $425,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  220 Melville Dr, Fairfield, CT 06825

  Welcome to 220 Melville Drive in Fairfield, a charming brick half duplex. Hardwood floors run throughout the home, beginning on the main level where a comfortable living room flows into the eat in kitchen perfect for everyday living and entertaining. Upstairs, the bedrooms offer a quiet retreat with natural light and updated bathroom with skylight. Outside, enjoy the convenience of a private two

  Lauren Iraeta KW Legacy Partners

  220 Melville Dr, Fairfield, CT 06825
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  /37

  $695,000

  • 3 Beds
  • 2 Baths
  • 1,382 Sq Ft

  53 Hilltop Dr, Southport, CT 06890

  Welcome to this charming Cape Cod-style home, offering an inviting entry into the quaint, historic village of Southport. Recently refreshed with a full interior repaint in a crisp, clean white palette, the home feels bright, open, and thoughtfully updated, with sparsely furnished spaces that highlight the light, flow, and flexibility. Recent improvements include a brand-new furnace, a new

  Kaitlin Fulco Coldwell Banker Realty

  53 Hilltop Dr, Southport, CT 06890
• 

  

  /23

  $649,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,190 Sq Ft

  378 High St, Fairfield, CT 06824

  Charming and well-maintained 3-bedroom, 2 full bath cape offering 1,190 sq ft of living space plus an additional 850 sq ft in the walk-out basement, ready to be finished for expanded living or recreation space. Step inside to a welcoming living room featuring a wood-burning fireplace, perfect for cozy evenings. The main level offers a bedroom and full bath, an eat-in kitchen/dining area, and a

  Liz Moretti BHGRE Gaetano Marra Homes

  378 High St, Fairfield, CT 06824
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  /16

  $4,299,000 New Construction

  • 5 Beds
  • 6 Baths
  • 4,879 Sq Ft

  5 Franklin Ave, Westport, CT 06880

  Nestled in one of Westport's most desirable walk-to-town neighborhoods, this exceptional new construction home combines timeless charm with modern luxury. Designed by acclaimed architect Judith Larson and crafted by trusted builder Redcoat Homes, this residence offers the perfect balance of style and functionality. Located on a level third-acre on a quiet cul-de-sac, the property is beautifully

  James Lanzaro Compass Connecticut, LLC

  5 Franklin Ave, Westport, CT 06880
• 

  

  /4

  $1,850,000

  • Land
  • 0.2 Acre
  • $9,250,000 per Acre

  31 Franklin St, Westport, CT 06880

  This transformative site is located on quaint street lined with early 1900s properties in the Historic Saugatuck area of Westport. One block away from train station I-95. Adjacent to the recently developed Saugatuck Center and Saugatuck River with restaurants, Cafes and luxury residential. Potential to acquire adjacent 19 Ketchum that is fully occupied as well as 31 Franklin. Please do not walk

  Peter Lane Ogents, LLC

  31 Franklin St, Westport, CT 06880
• 

  

  /4

  $2,149,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,250 Sq Ft

  2 Mellow St, Fairfield, CT 06824

  New Construction! Beautiful Beach area home to be built on a double cul de sac by one of Fairfield's premier builders. Just over 3000 sq ft on three levels with 4 bedrooms, 4.5 bathrooms and a finished 3rd floor. Open concept kitchen and family room as well as a formal dining room and living room to finish off the first floor. Exceptional finishes and fine craftsmanship throughout the house.

  Dawn Gitman William Raveis Real Estate

  2 Mellow St, Fairfield, CT 06824
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  /10

  $2,600,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,288 Sq Ft

  2 Fairport Rd, Westport, CT 06880

  Experience a new standard of modern elegance in this brand new luxury home in the heart of Westport. Spanning over 4,200 square feet of finished living space across four beautifully appointed levels, this residence features stunning white oak floors and premium finishes throughout. The main level features a bright open floor plan that seamlessly integrates a gourmet kitchen with large center

  Kristi Law William Pitt Sotheby's Int'l

  2 Fairport Rd, Westport, CT 06880
• 

  

  /3

  $4,795,000 New Construction

  • 5 Beds
  • 7.5 Baths
  • 7,809 Sq Ft

  110 Long Lots Rd, Westport, CT 06880

  110 Long Lots is an exceptional new construction home showcasing timeless coastal architecture, set within one of Westport's most coveted neighborhoods. The exterior features a classic white cedar shingle siding, complemented by a three-car garage, private pool, and expansive bluestone patio designed for effortless outdoor entertaining and everyday living. Thoughtfully designed for a seamless

  Amanda Spatola Houlihan Lawrence

  110 Long Lots Rd, Westport, CT 06880
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  /2

  $149,000

  • Land
  • 0.09 Acre
  • $1,655,556 per Acre

  90 Lee Ave, Bridgeport, CT 06605

  Build your next project in Bridgeport's West End! 90 Lee Avenue is a level lot located on a residential street just minutes from Black Rock, Seaside Park, the Metro-North station, and University of Bridgeport. This parcel offers a fantastic opportunity for development in a growing area with strong rental demand. All public utilities are available at the street. Excellent potential for investors,

  Melanie Billie BHGRE Gaetano Marra Homes

  90 Lee Ave, Bridgeport, CT 06605
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  /38

  $3,999,000 Open Sun 12PM - 2PM

  • 6 Beds
  • 7 Baths
  • 7,092 Sq Ft

  18 Woodhill Rd, Westport, CT 06880

  Nestled near the end of an upscale cul-de-sac in prime Greens Farms, the newest SIR SIGNATURE Home blends timeless design with modern luxury on beautifully flat, private grounds. A heated gunite pool with auto cover anchors the expansive backyard w/ two connecting raised patios creates a true indooroutdoor retreat. Inside, sunfilled spaces showcase the craftsmanship SIR is known for. High

  Doug Bross Coldwell Banker Realty

  18 Woodhill Rd, Westport, CT 06880
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  /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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  /36

  $1,695,000

  • 6 Beds
  • 4.5 Baths
  • 5,325 Sq Ft

  212 Fence Row Dr, Fairfield, CT 06824

  Set on over two private acres in the gated community of The Ridge, this stunning estate combines modern comfort with timeless design. Residents enjoy resort-style amenities including a clubhouse, pool, tennis courts, playground, basketball court, private recreation facilities, and 24/7 gate security. Step inside through a soaring vaulted foyer that opens to a sun-filled living room framed by a

  Adele Higgins Higgins Group Real Estate

  212 Fence Row Dr, Fairfield, CT 06824
• 

  

  /40

  $2,395,000

  • 4 Beds
  • 4.5 Baths
  • 3,620 Sq Ft

  783 Reef Rd, Fairfield, CT 06824

  Welcome to 783 Reef Road, a beautifully crafted home in the highly desirable Penfield Beach area of Fairfield. This elegant residence combines refined design with modern comfort, offering four bedrooms, four and a half bathrooms, and approximately 3,620 square feet of interior living space and an additional nearly 1,400 square feet of basement storage space. Inside, the foyer opens to a layout

  Daniel Durante Criterion Real Estate LLC

  783 Reef Rd, Fairfield, CT 06824
• 

  

  /28

  $975,000

  • 3 Beds
  • 2.5 Baths
  • 1,998 Sq Ft

  88 Veres St, Fairfield, CT 06824

  Coastal charm meets modern living in this exceptional beach-area home, perfectly positioned in a coveted walk-to-everything neighborhood. Cherished by the same family for generations, the residence was taken down to the studs and thoughtfully rebuilt in 1994, creating a home that blends classic character with today's standards of comfort and finishes. The location is truly unbeatable - just steps

  Karen Cross William Raveis Real Estate

  88 Veres St, Fairfield, CT 06824
• 

  

  /40

  $1,430,000 Open Sat 1PM - 4PM

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

  781 Post Rd E Unit 104, 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

  781 Post Rd E Unit 104, Westport, CT 06880
• 

  

  /40

  $2,498,000 Open Sun 1PM - 3PM

  • 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

Showing Results 81 - 120, Page 3 of 4