Southport, CT Homes for Sale

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  $1,490,000

  • Land
  • 0.15 Acre
  • $9,933,333 per Acre

  15 Gorham Ave, Westport, CT 06880

  Nestled on a charming historic street in one of Westport's most desirable neighborhoods, 15 Gorham Avenue offers a rare opportunity to build your dream home just moments from the heart of town. This exceptional property allows for the construction of a approximately 2,500+/- square foot residence, perfectly suited for today's lifestyle while blending beautifully with the character of the

  Peter Lane Ogents, LLC

  15 Gorham Ave, Westport, CT 06880
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  /40

  $1,975,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 4,018 Sq Ft

  39 Marion Rd, Westport, CT 06880

  Nestled in the coveted Old Hill section of Westport, this exceptional residence offers a rare blend of space, serenity, & timeless appeal. With over 3,200 square feet, the home unfolds beautifully-beginning with a gracious entry foyer, leading into the living room with hardwood floors and anchored by a classic fireplace. The large eat-in kitchen offers double ovens, an abundance of cabinets and

  Stacy Pfannkuch Century 21 AllPoints Realty

  39 Marion Rd, Westport, CT 06880
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  /40

  $4,610,000

  • 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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  /18

  $899,000

  • 4 Beds
  • 2 Baths
  • 1,243 Sq Ft

  20 Benson Place, Fairfield, CT 06824

  Location, Location, Location! Offered for the first time in generations, this character-filled home is a rare opportunity to create something special. Ideally located near the beach, marina, parks, trails, and town. Lovingly maintained with all mechanicals in working order. The layout includes 4 bedrooms and 2 full baths--2 bedrooms and 1 bath on the main level, along with a living room, kitchen,

  Anthony Capalbo BHHS New England Properties

  20 Benson Place, Fairfield, CT 06824
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  $15,000,000

  • 7 Beds
  • 10 Baths
  • 9,129 Sq Ft

  4800 Congress St, Fairfield, CT 06824

  The Ultimate East Coast Sanctuary-Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is engineered for the world's most discerning icons who demand seclusion with proximity to NYC. This 38.91-acre compound ,is the mid century former home of Richard Rodgers, composer of The Sound of Music. Restored and expanded to incorporate 7 bedrooms and 7

  Leslie Razook William Pitt Sotheby's Int'l

  4800 Congress St, Fairfield, CT 06824
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  /2

  $4,300,000

  • 6 Beds
  • 6 Baths
  • 6,000 Sq Ft

  394 Penfield Rd, Fairfield, CT 06824

  IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7

  Helene Salerno Ogents, LLC

  394 Penfield Rd, Fairfield, CT 06824
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  $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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  $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

  $2,150,000

  • 4 Beds
  • 3.5 Baths
  • 3,023 Sq Ft

  234 Wilton Rd, Westport, CT 06880

  Wilton Road places you minutes from town and the shoreline. At 234, convenience and privacy coexist. A turn onto a side lane and a set-back approach behind mature trees create a setting that feels distinctly separate from the street. Originally built in 1884, the home has been fully renovated and thoughtfully expanded. A 2024 addition reshaped the main level, enlarging the kitchen and introducing

  Cindy Raney Coldwell Banker Realty

  234 Wilton Rd, Westport, CT 06880
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  /40

  $3,000,000

  • 6 Beds
  • 5.5 Baths
  • 5,952 Sq Ft

  70 Meadow Ridge Rd, Fairfield, CT 06824

  Nestled on a picturesque cul-de-sac street in the heart of Southport, 70 Meadow Ridge Rd offers the perfect blend of classic charm and modern convenience. This custom home boasts 6 bedrooms and 5, Bathrooms providing ample space for comfortable living and entertaining. Step inside to discover sun-drenched living spaces featuring gleaming hardwood floors, a cozy fireplace, and an open-concept

  David Krasnoff Compass Connecticut, LLC

  70 Meadow Ridge Rd, Fairfield, CT 06824
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  /27

  $299,000

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

  3250 Fairfield Ave Unit 302, Bridgeport, CT 06605

  Fully-furnished, stylish, sunny 2-bed, 2-bath Black Rock condo delivers the ultimate fun, hassle-free lifestyle in one of Fairfield County's most vibrant seaside communities. Ideal for investors, down-sizers or first-time buyers, this home features in-unit laundry, central air, and efficient natural gas heat-keeping monthly bills manageable and eliminating concerns about rising oil costs. Chic,

  Cindy Searight Compass Connecticut, LLC

  3250 Fairfield Ave Unit 302, Bridgeport, CT 06605
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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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  $3,990,000

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

  13 Rockyfield Rd, Westport, CT 06880

  This pristine Colonial offers timeless Westport elegance and effortless living, set on 1.12 flat, manicured acres framed by classic stone walls in a coveted, quiet neighborhood just one hour from NYC. The five-bedroom home features five full and two half baths, two dedicated offices, two versatile bonus spaces, custom millwork throughout, and abundant storage-perfect for today's work-from-home,

  Danna Rogers Higgins Group Bedford Square

  13 Rockyfield Rd, Westport, CT 06880
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  /40

  $2,995,000

  • 6 Beds
  • 5.5 Baths
  • 4,322 Sq Ft

  598 S Benson Rd, Fairfield, CT 06824

  RARE BEACH PROPERTY ~ Steps to Sandcastle Playground, Jennings Beach and South Benson Marina - this striking Colonial delivers a unique blend of luxurious beach living and exceptional build quality. Homes of this caliber seldom become available along the shoreline. ~ EXPANSIVE FIRST FLOOR ~ The house features a sprawling first floor Great Room and show stopping Chef's Kitchen which combine in a

  Julie Vanderblue Higgins Group Real Estate

  598 S Benson Rd, Fairfield, CT 06824
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  /19

  $3,900,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,100 Sq Ft

  1008 Fairfield Beach Rd, Fairfield, CT 06824

  1008 Fairfield Beach Road- A Masterpiece on Fairfield's Iconic Coastline. Where modern luxury meets coastal elegance. Presented by one of Fairfield County's premier celebrity developers, this extraordinary new construction beach home offers an unparalleled lifestyle with panoramic, unobstructed views of the Long Island Sound with jaw-dropping sunsets. Stand out in the neighborhood with one of the

  Valerie Alvarez Serhant Connecticut, LLC

  1008 Fairfield Beach Rd, Fairfield, CT 06824
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  /24

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  75 Hemlock St, Bridgeport, CT 06605

  Beautifully remodeled in 2024 1,300 SQFT cape cod right on the border of Fairfield. Take a look at the completely new home from the bottom up. New roof, new siding, new windows, new doors, new patio, new kitchen, new appliances, new hardwood floors, new insulation, new sheetrock, new wiring, new plumbing, new furnace, new hot water heater, new central air, new bathrooms. New vinyl fencing

  Jose Montilla eXp Realty

  75 Hemlock St, Bridgeport, CT 06605
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  /40

  $5,800,000

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

  80 Compo Rd N, Westport, CT 06880

  Timeless design meets modern sustainability in this stunning shingle-style home, set on 1.5 private acres just a short walk from town. Sunlight fills every room through oversized Kolbe windows, showcasing park-like grounds and mature plantings. The kitchen impresses with custom cabinetry, a handcrafted zinc island, and top-tier Wolf and Sub-Zero appliances. Step outside to a spectacular bluestone

  Adrienne Durkin Compass Connecticut, LLC

  80 Compo Rd N, Westport, CT 06880
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  /40

  $979,000

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

  25 Maplewood Ave, Westport, CT 06880

  LOVE IT TODAY, DREAM YOUR TOMORROW! WOW!!! This snuggly 1800sf bungalow is ready for you to move right in with 3-bedrooms, 2-1/2 baths total on 3 levels (which includes the 1 bedroom/1bath Lower Level legal accessory apartment). Guests feel welcomed the minute they step through the 25 Maplewood front door into the light-filled main level where entertainment feels easy-peasy! The open floor plan

  Martha Eidman Coldwell Banker Realty

  25 Maplewood Ave, Westport, CT 06880
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  $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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  /15

  $5,474,945 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 6,660 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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  $4,899,000 New Construction

  • 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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  $5,499,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 7,387 Sq Ft

  36 Maple Ave S, Westport, CT 06880

  Beautiful Georgian Colonial style home in desired Greens Farms neighborhood design by renowned architect Judith Larson. A fabulous Redcoat design team make this home a must, perfect for todays's lifestyle with a classic feel. This 6 bedroom residence is set on a flat, level.70 acre property embodying a perfect synergy of architectural excellence and an enviable location. Crafted for modern living

  Kelly Loucas Compass Connecticut, LLC

  36 Maple Ave S, Westport, CT 06880
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  /19

  $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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  $1,799,000

  • 3 Beds
  • 3.5 Baths
  • 3,141 Sq Ft

  127 Spruce St, Southport, CT 06890

  Enjoy stylish and easy living in this spectacular townhome on Southport's much-loved, storybook Spruce Street. Thoughtful design by renowned local architect Jack Franzen ensures a sophisticated and smart floor plan featuring top-quality finishes, high ceilings and beautiful wood floors. A great home for entertaining or very comfortable living - the Great Room enjoys a gas fireplace and opens

  Ellen Fusco Compass Connecticut, LLC

  127 Spruce St, Southport, CT 06890
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  $1,599,000

  • 5 Beds
  • 3.5 Baths
  • 3,229 Sq Ft

  164 Wakeman Rd, Fairfield, CT 06824

  Nestled in Fairfield's highly sought-after University neighborhood, this exceptional home beautifully blends timeless vintage charm with a warm, modern aesthetic. Set on a private, arborvitae-lined property, the outdoor space features a stone patio and gas fire rock seating area. Inside, the inviting layout offers effortless flow and abundant natural light. The living room, anchored by a

  Katie O'Grady Compass Connecticut, LLC

  164 Wakeman Rd, Fairfield, CT 06824
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  /40

  $872,000

  • 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
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  /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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  /40

  $2,695,000

  • 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
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  $319,000

  • 3 Beds
  • 2 Baths
  • 1,755 Sq Ft

  25 Cartright St Unit 5D, Bridgeport, CT 06604

  Stunning End-Unit 3-Bedroom, 2-Bath NYC-Style Condo - Nestled in the heart of the highly sought-after Brooklawn community, this spacious 1,755 sq ft New York City-style condominium blends contemporary comfort with urban sophistication. Located just steps from the Fairfield town line, Unit 5D offers the perfect balance of city convenience and suburban tranquility. Step into a welcoming large foyer

  Pamela Williams Real Broker CT, LLC

  25 Cartright St Unit 5D, Bridgeport, CT 06604
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  $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
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  $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
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  $3,449,000

  • 5 Beds
  • 7 Baths
  • 5,515 Sq Ft

  2683 Bronson Rd, Fairfield, CT 06824

  In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate presents a rare opportunity in one of Fairfield's most coveted locations. Set on just over two acres of beautifully landscaped, professionally photographed grounds, the property reflects a timeless elegance that would be costly to replicate today. Across from a distinguished equestrian family

  Tara Hawley Coldwell Banker Realty

  2683 Bronson Rd, Fairfield, CT 06824
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  $2,295,000

  • 4 Beds
  • 3 Baths
  • 3,099 Sq Ft

  140 Roseville Rd, Westport, CT 06880

  Perfectly sited on 1.59 acres, this 4-bedroom, 3-bath antique home invites a lifestyle defined by warmth, ease, and understated elegance. Original wideboard floors, an impressive hearth fireplace, and beautifully preserved details create a sense of history, while the open, light-filled layout supports a modern way of living-whether hosting gatherings or enjoying quiet moments at home. The main

  Emily Gordon Coldwell Banker Realty

  140 Roseville Rd, Westport, CT 06880
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  $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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  /18

  $1,400,000

  • Land
  • 3 Acres
  • $466,667 per Acre

  20 Ermine St, Fairfield, CT 06824

  Endless opportunities await at this property-whether a, buyer envisions their ideal home, a buyer interested in constructing a multigenerational family residence, someone looking to renovate the current home and take advantage of the surrounding land, or a builder looking for a new project, this is the perfect place for you. Three individual lots, totaling three acres, are available for purchase

  Harriet Stone William Pitt Sotheby's Int'l

  20 Ermine St, Fairfield, CT 06824
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  $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
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  $619,000

  • 5 Beds
  • 3 Baths
  • 2,328 Sq Ft

  8-10 Jetland Place, Bridge Port, CT 06605

  Located in the heart of Black Rock, this home is a fully rented multi-family opportunity in one of Bridgeport's most walkable and desirable neighborhoods. Two units are at or near market rent, with one unit currently below market offering immediate upside potential. Recent improvements include a new kitchen, bathroom, and flooring in the second-floor unit, a finished third-floor living area with

  Eric Garces BHGRE Gaetano Marra Homes

  8-10 Jetland Place, Bridge Port, CT 06605
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  $5,185,000

  • 6 Beds
  • 8 Baths
  • 8,190 Sq Ft

  19 Mortar Rock Rd, Westport, CT 06880

  Stunning modern transitional home built by Compo Luxury Homes in 2024 and ideally located just minutes to downtown Westport, Compo Beach, and the train. Set on .65 acres with city water, sewer, and natural gas, this beautifully designed residence offers over 8,000 square feet across four finished levels with 6 bedrooms, 6 full and 2 half baths. The open floor plan features a chef's kitchen with

  Danna Rogers Higgins Group Bedford Square

  19 Mortar Rock Rd, Westport, CT 06880
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  /32

  $995,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  20 Hickory Dr, Westport, CT 06880

  Tucked on a cul-de-sac in the heart of Long Lots, this light-filled ranch offers the ease of single-level living within a thoughtfully composed floor plan. Well-proportioned rooms and seamless flow create a home that feels both comfortable and refined. The living room, framed by a large picture window, is bathed in natural light throughout the day and anchored by a custom fireplace surround. An

  Barbara Sweeney Coldwell Banker Realty

  20 Hickory Dr, Westport, CT 06880
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  $1,699,000

  • 2 Beds
  • 1.5 Baths
  • 2,131 Sq Ft

  160 Cedar Rd, Southport, CT 06890

  Embrace the tranquility of this exceptional equestrian estate, nestled on 4.45 acres of private beautiful land. This serene property is a haven for horse and animal lovers, featuring expansive pastures, barn, stable, shed, paddocks and sand riding ring. This one-of-a-kind property borders the Aspetuck Land Trust, offering unmatched natural beauty and privacy. The renovated and well-maintained

  Ellen Fusco Compass Connecticut, LLC

  160 Cedar Rd, Southport, CT 06890

Showing Results 81 - 120, Page 3 of 4