Southport, CT Houses for Sale

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  /29

  $450,000

  • 5 Beds
  • 1.5 Baths
  • 2,507 Sq Ft

  47 Lenox Ave, Bridgeport, CT 06605

  Welcome to 47 Lenox Avenue, a generously sized Colonial full of charm and character. This home offers 5 bedrooms, with the flexibility to use the 5th as a private office or den. The first floor features a living room with a classic fireplace, a kitchen, a half bath, and a dining room currently being used as a bedroom-but easily converted back for traditional dining. Upstairs, you'll find four

  Lucy Billini-Artis BHGRE Gaetano Marra Homes

  47 Lenox Ave, Bridgeport, CT 06605
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  /40

  $3,899,000

  • 4 Beds
  • 4.5 Baths
  • 3,500 Sq Ft

  61 Clapboard Hill Rd, Westport, CT 06880

  Located in prestigious Greens Farms, this European-inspired Colonial captures the timeless romance of the countryside in a coveted Westport location. Enter through private gates into a tranquil sanctuary, where meadow views & the soft outline of the home's romantic arched windows set a tone of understated elegance. The warm and inviting interiors offer flexibility & ideal flow, with a formal

  Lorelei Atwood Higgins Group Real Estate

  61 Clapboard Hill Rd, Westport, CT 06880
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  /40

  $3,499,000

  • 5 Beds
  • 7 Baths
  • 8,110 Sq Ft

  4 Jennings Ct, Westport, CT 06880

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

  Linda Skolnick Coldwell Banker Realty

  4 Jennings Ct, Westport, CT 06880
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  /38

  $3,899,000

  • 4 Beds
  • 4.5 Baths
  • 4,693 Sq Ft

  11 Edgewater Hillside, Westport, CT 06880

  COMPO BEACH WATER VIEWS at this picture-perfect beach house. Edgewater Hillside is the best-kept secret at Compo Beach, a private Hamptons-style cul de sac where each home is prettier than the next and water views abound. This exceptional residence combines timeless design with high-end amenities and so much space to live and entertain, walking distance to Compo Beach and Old Mill Beach, and

  Cyd Hamer William Pitt Sotheby's Int'l

  11 Edgewater Hillside, Westport, CT 06880
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  /17

  $3,575,000

  • 5 Beds
  • 4.5 Baths
  • 3,200 Sq Ft

  26 Treadwell Ave, Westport, CT 06880

  A masterful reinvention by Michael Greenberg of a historic 1894 Victorian Farmhouse, 26 Treadwell Avenue is a rare blend of old-world character and modern luxury. Completely rebuilt in 2025, this one-of-a-kind residence honors its roots with exposed antique beams, white oak floors, and curated architectural details while embracing a clean, contemporary sensibility throughout. Set on a

  Michael Greenberg The Source Realty

  26 Treadwell Ave, Westport, CT 06880
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  /14

  $399,999

  • 3 Beds
  • 2 Baths
  • 1,060 Sq Ft

  Unlisted Address

  EXPANSIVE BACKYARD - PERFECT FOR CONTRACTORS, LANDSCAPERS, OR EXTRA PARKING! Located in the highly desirable Brooklawn neighborhood, this charming home beautifully blends classic character with modern comfort. The spacious backyard offers endless potential, ideal for storing equipment, parking multiple vehicles, or enjoying the outdoors.

  Andrew Cevasco Las Americas Real Estate

  Unlisted Address
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  /40

  $4,250,000

  • 6 Beds
  • 8.5 Baths
  • 6,897 Sq Ft

  1084 Sturges Hwy, Westport, CT 06880

  Luxury Living on the Fairfield/Westport Border Set in the heart of Greenfield Hill, this exceptional 6-bedroom, 8-bath estate offers a rare combination of privacy, elegance, and resort-style amenities-just minutes from the Post Road and 50 miles from NYC. Thoughtfully positioned on the Fairfield/Westport line, the residence features expansive, sun-filled interiors ideal for everyday living and

  Andrew Whiteley Brown Harris Stevens

  1084 Sturges Hwy, Westport, CT 06880
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  /34

  $1,495,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,166 Sq Ft

  17 Grays Farm Rd, Weston, CT 06883

  Stonehaven: This meticulous home was rebuilt and expanded in 2015, refinished floors and fresh paint in 2025, and is located on 2 sunny acres in lower Weston. Professionally crafted stone pillars, walls, and patios, and a sweeping circular driveway create exceptional curb appeal in a serene cul-de-sac setting. The renovation and expansion transformed the property-adding a charming front porch and

  Mary Palmieri Gai Berkshire Hathaway NE Prop.

  17 Grays Farm Rd, Weston, CT 06883
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  /10

  $1,000,000

  • 4 Beds
  • 2.5 Baths
  • 2,644 Sq Ft

  647 Bronson Rd, Southport, CT 06890

  First Time on the Market - A Southport Treasure with Endless Possibilities For the first time since 1912, this cherished Southport residence is being offered for sale. Passed down through generations, this classic colonial has been a cornerstone of one family's legacy for over a century - and now it's ready for its next chapter. Set on nearly a half-acre in the heart of Southport, this property

  Vienna DiPiave William Pitt Sotheby's Int'l

  647 Bronson Rd, Southport, CT 06890
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  /39

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  28 Crescent Park Rd, Westport, CT 06880

  Completely remodeled 3-bedroom ranch-style home in coveted Westport. Featuring an inviting open floor plan, this thoughtfully renovated residence creates a perfect flow for modern living and entertaining. The home showcases a private master suite with contemporary finishes, and a large primary bathroom, while the open-concept main living areas are bathed in natural light. Following a complete

  Karim Douich William Raveis Real Estate

  28 Crescent Park Rd, Westport, CT 06880
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  /40

  $5,950,000

  • 5 Beds
  • 7.5 Baths
  • 14,038 Sq Ft

  11 Beachside Common, Westport, CT 06880

  A true Westport icon, 11 Beachside Common is one of the most architecturally distinctive homes on the Connecticut coast-known to anyone who's ever strolled Burying Hill Beach. Set on 2.6 waterfront acres, the property offers sweeping southern views over Sherwood Island and Long Island Sound, with sunsets that rival the Low Country and birdlife that fills the surrounding marsh with movement and

  Wendy Ryan Brown Harris Stevens

  11 Beachside Common, Westport, CT 06880
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  /39

  $520,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,510 Sq Ft

  155 Moody Ave, Fairfield, CT 06825

  WELCOME HOME! Step inside and feel the warmth of family life in the eat-in kitchen, where meals and laughter come together. Curl up by the crackling fireplace, soak in sunlight in the cozy den, or gather in the spacious dining room. Escape to the serene storybook garden-breathe deeply, feel the sun, and let the calm envelop you. Sunlit rooms, spacious bedrooms, and a walk-up attic await. The

  Joy Serafin-Cehovsky Higgins Group Real Estate

  155 Moody Ave, Fairfield, CT 06825
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  /35

  $684,500

  • 4 Beds
  • 2 Baths
  • 1,152 Sq Ft

  10 Crescent Park Rd, Westport, CT 06880

  Enjoy the renovation, attention to detail and all that Westport offers from your 4-bedroom, 2 full bath home featuring designer kitchen, fireplace, custom built-ins/shelving, vaulted ceilings and new, finished hardwood flooring throughout. Gas hot air heating with central air, new windows and fenced yard with oversized shed situated on private neighborhood road for your nightly stroll or bike

  John Hackett William Raveis Real Estate

  10 Crescent Park Rd, Westport, CT 06880
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  /21

  $450,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  67 Campfield Dr, Fairfield, CT 06825

  Recently updated Spacious half-duplex in the heart of Fairfield where you'll enjoy the privacy and feel of single-family living. It has 3 bedrooms and 1.5 baths, with open floor plan concept on first floor. ideal for comfortable living. Recent updates include a new roof, fresh paint inside and out, and remodeled 1/2 bathroom. Central air ensures comfort during hot summer nights, while the cozy

  Aziz Seyal William Raveis Real Estate

  67 Campfield Dr, Fairfield, CT 06825
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  /34

  $1,399,000

  • 3 Beds
  • 2.5 Baths
  • 2,265 Sq Ft

  109 Greens Farms Rd, Westport, CT 06880

  Located in sought-after Greens Farms, this wonderful and renovated Colonial-style Farmhouse, perfectly blends classic charm + modern updates. Nestled on a serene + picturesque flat acre, the residence offers a central location just moments from beaches, shopping, dining + two convenient train stations. Step inside to a sunlit first floor designed for effortless entertaining. The open floor plan

  Karen Scott Compass Connecticut, LLC

  109 Greens Farms Rd, Westport, CT 06880
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  /37

  $3,399,000

  • 5 Beds
  • 5 Baths
  • 3,961 Sq Ft

  318 320 Pine Creek Ave, Fairfield, CT 06824

  Welcome to a truly exceptional opportunity-a direct waterfront compound offering expansive views of Long Island Sound, a dock, &endless showstopping sunsets. This remarkable property features 2 residences: a fully renovated, FEMA-compliant main house AND a charming, income-generating guest cottage.The Main Residence (320)is a modern coastal retreat offering 3,129 sq ft of sun-drenched living

  Deirdre Andreoli Compass Connecticut, LLC

  318 320 Pine Creek Ave, Fairfield, CT 06824
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  /20

  $1,395,000

  • 4 Beds
  • 5.5 Baths
  • 4,906 Sq Ft

  3853 Congress St, Fairfield, CT 06824

  Sprawling ten room ranch style residence offering 3 acres on a prime estate street in Greenfield Hill. This stately home is discreetly positioned behind a brick wall and approached by a sweeping circular drive creating a grand sense of arrival. Inside this impressive home discover a striking Indoor Pool housed in its own sun lit pavilion. This dramatic recreation space adjoins the Kitchen and

  Paul Triantafel William Pitt Sotheby's Int'l

  3853 Congress St, Fairfield, CT 06824
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  /29

  $1,699,000

  • 4 Beds
  • 3.5 Baths
  • 3,648 Sq Ft

  60 Eleanor Terrace, Fairfield, CT 06824

  Savor the coastal lifestyle in this chic, modern 2021 construction home in the highly desirable Fairfield Beach neighborhood. Just a quick stroll to the beach with pavillion, Fairfield town marina & Sand Castle Park. Hard to find beach area NOT in Flood Zone! No flood insurance required. Thoughtfully designed for open & airy living. Step into open concept living with a spacious living room that

  Katie O'Grady Compass Connecticut, LLC

  60 Eleanor Terrace, Fairfield, CT 06824
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  /40

  $12,000,000

  • 7 Beds
  • 6.5 Baths
  • 8,119 Sq Ft

  260 Willow St, Southport, CT 06890

  Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every

  Elizabeth Tritschler William Raveis Real Estate

  260 Willow St, Southport, CT 06890
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  /37

  $1,599,000

  • 4 Beds
  • 5 Baths
  • 4,277 Sq Ft

  175 Battery Park Dr, Bridgeport, CT 06605

  Experience breathtaking views of St. Mary's by the Sea from this beautifully updated Colonial nestled on a hilltop in the highly desirable neighborhood of Black Rock. The spectacular vistas of Long Island Sound are enhanced by the multi-level decks and patio providing calming sunrises and colorful sunsets. The outdoor kitchen is great for entertaining with a grill, oven and fire pit. Perfect for

  Lori Di Bartholomeo William Raveis Real Estate

  175 Battery Park Dr, Bridgeport, CT 06605
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  /40

  $1,799,999

  • 6 Beds
  • 3.5 Baths
  • 4,318 Sq Ft

  312 Towne House Rd, Fairfield, CT 06824

  A gracious front porch welcomes you to this sophisticated colonial where comfort and luxury abound. The entry hall with striking floor to ceiling picture frame molding, setting the tone for the refined details found throughout the home. The family room greets you with many carefully curated features including book shelves framing the entry, coffered ceiling, gas fireplace flanked by built in

  Paulette Cuozzo William Raveis Real Estate

  312 Towne House Rd, Fairfield, CT 06824
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  /14

  $288,000

  • 2 Beds
  • 2 Baths
  • 931 Sq Ft

  96 Davis Ave, Bridgeport, CT 06605

  This property is truly an investor's dream! 96 Davis Avenue is nestled in the very desirable Black Rock section of Bridgeport, CT. Situated perfectly for all that Black Rock has to offer. Within walking distance to the Fairfield Black Rock Train Station or the iconic Saint Mary's by the Sea with beautiful views of Long Island Sound. Just a few minutes' from Elicit Brewery, local shops and

  Bogdan Stefanide KW Legacy Partners

  96 Davis Ave, Bridgeport, CT 06605
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  /40

  $15,000,000

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

  4800 Congress St, Fairfield, CT 06824

  Surrounded by stone walls, this storied, spectacular and private 38.91-acre Greenfield Hill country compound has had a stunning top-level transformation, creating a one of a kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was restored and expanded to incorporate 7 bedrooms and 7 full baths, all with views over the

  Leslie Razook William Pitt Sotheby's Int'l

  4800 Congress St, Fairfield, CT 06824
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  /40

  $3,300,000

  • 5 Beds
  • 8 Baths
  • 6,414 Sq Ft

  750 Burr St, Fairfield, CT 06824

  Lions Gate: No need to move to the south of France as this extraordinary residence is right here in coveted Fairfield. Enter through grand gates into a world of privacy where character, convenience, security & serenity magically meet. Magazine-worthy grounds are the soul of the estate-lush, expansive, & exquisitely curated. With a shimmering pool, spectacular California Redwood Pool House with

  Julie Vanderblue Higgins Group Real Estate

  750 Burr St, Fairfield, CT 06824
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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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  /40

  $4,999,000

  • 5 Beds
  • 4.5 Baths
  • 4,669 Sq Ft

  216 Hillspoint Rd, Westport, CT 06880

  Compo Beach Coastal Compound+Water Views+Approved Lot! A rare Compo Beach opportunity-beautifully rebuilt, expanded 5 bed/4.5 bath home on a .47-acre parcel-INCLUDES AN APPROVED BUILDABLE .14 ACRE LOT. Enjoy stunning water views, privacy & unmatched lifestyle just steps from Old Mill & Compo Beaches! Discover a rare blend of timeless character & sophisticated living in this coastal estate.

  Sarah Fair William Raveis Real Estate

  216 Hillspoint Rd, Westport, CT 06880
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  /37

  $4,895,000

  • 7 Beds
  • 7.5 Baths
  • 9,035 Sq Ft

  26 Morningside Dr S, Westport, CT 06880

  Welcome to 26 Morningside Drive South, the first completed home in Sherwood Estates at Greens Farms. Builder has recently added over $150,000 in exterior upgrades into the final plans!!!! This newly built four-level residence blends timeless design with modern luxury in one of Westport's most desirable neighborhoods. The main level features a chef's kitchen with custom island and pantry, open

  John Schiaroli Coldwell Banker Realty

  26 Morningside Dr S, Westport, CT 06880
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  /40

  $3,450,000

  • 5 Beds
  • 5 Baths
  • 3,561 Sq Ft

  6 Over Rock Ln, Westport, CT 06880

  Welcome to 6 Over Rock Lane - a stunning 1920s colonial retreat in the heart of Westport, Connecticut blending timeless New England charm with sophisticated modern living. A unique move-in opportunity with curated designer furniture offered. Set on a quiet, luxurious street in one of Westport's most desirable neighborhoods, this property offers peace, privacy, and proximity - just minutes from

  Judy Michaelis Coldwell Banker Realty

  6 Over Rock Ln, Westport, CT 06880
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  /31

  $1,850,000

  • 6 Beds
  • 5.5 Baths
  • 5,489 Sq Ft

  130 Easton Rd, Westport, CT 06880

  Unique opportunity to renovate this classic Westport estate on three professionally landscaped acres with a pool. You will love the great room with views of the pond and property. Six bedrooms makes space for everyone with a separate guest wing that is perfect for an au-pair.

  David Weber Compass Connecticut, LLC

  130 Easton Rd, Westport, CT 06880
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  /21

  $699,000

  • 3 Beds
  • 3 Baths
  • 1,586 Sq Ft

  11 Twin Brooks Ln, Fairfield, CT 06824

  Opportunity Knocks for this perfect opportunity for renovation or expansion in prime Location! Nestled on a quiet lower Greenfield Hill cul-de-sac with a peaceful yard, this solidly built home is being sold as-is, where-is with no representation of electric, plumbing, or mechanical systems. TOWN VARIANCE IS IN PLACE FOR EXPANSION and for adding a second story, providing incredible potential to

  Michael Traum RE/MAX Heritage

  11 Twin Brooks Ln, Fairfield, CT 06824
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  /37

  $3,100,000 Open Sat 1PM - 3PM

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

  450 Penfield Rd, Fairfield, CT 06824

  New Construction in coveted BEACH AREA! This 4,000 sqft custom Colonial blends coastal charm with modern luxury-just a short walk to Penfield Beach, Fairfield Beach Club, vibrant downtown, the train, and top-rated schools. With 5-6 bedrooms, 4.5 baths, and 3 finished levels, this elevator-ready home offers exceptional design, flow, and comfort. The open concept kitchen is both functional and

  Julie Vanderblue Higgins Group Real Estate

  450 Penfield Rd, Fairfield, CT 06824
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  /40

  $1,900,000

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

  260 Range Rd, Southport, CT 06890

  Located on a quiet cul-de-sac in one of Southport's premier family neighborhoods, this elegant 4-bedroom, 2 full and 2 half-bath Colonial by Toll Brothers combines timeless design with modern comfort. The stately "Cedarbrook" Federal Colonial model welcomes you with a grand two-story foyer, setting the stage for the sophisticated interiors. Formal living and dining rooms are ideal for

  Julie Vanderblue Higgins Group Real Estate

  260 Range Rd, Southport, CT 06890
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  /40

  $2,895,000

  • 6 Beds
  • 4.5 Baths
  • 6,856 Sq Ft

  5 Northside Ln, Westport, CT 06880

  A true Westport landmark, Staffordshire Hall is an extraordinary gated stone estate blending timeless grandeur with modern luxury. Privately nestled on manicured grounds, this bespoke manor spans three levels of meticulously crafted living space. A sweeping circular drive leads to the columned entrance. The Great Hall stuns with a stone hearth, coffered ceilings, and French doors opening to the

  Alex Chingas Coldwell Banker Realty

  5 Northside Ln, Westport, CT 06880
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  /26

  $4,900,000

  • 7 Beds
  • 5.5 Baths
  • 7,995 Sq Ft

  37 Green Acre Ln, Westport, CT 06880

  A rare investment opportunity to own a storied 1936 estate on a desirable, private street in the heart of Westport. Set on 4.3 acres at the end of a tranquil cul-de-sac, this legacy property offers the ultimate in privacy and location, just one mile from both Westport's vibrant town center and the beach. The primary residence spans approximately 8,000 square feet, rich with timeless architecture

  Lisa Bortz William Pitt Sotheby's Int'l

  37 Green Acre Ln, Westport, CT 06880
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  /31

  $6,500,000

  • 6 Beds
  • 6.5 Baths
  • 6,585 Sq Ft

  69 Beachside Ave, Westport, CT 06880

  Nestled along Westport's prestigious 'Gold Coast,' this architecturally magnificent estate on 4+ acres of park-like grounds with a breathtaking pool and professional-grade Har-Tru tennis court is a haven for luxury living and distinguished entertaining. Surrounded by major estates in one of the most sought-after coastal regions in the Northeast, it boasts access to pristine beaches, sophisticated

  Doug Bross Coldwell Banker Realty

  69 Beachside Ave, Westport, CT 06880
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  /40

  $25,000,000

  • 6 Beds
  • 11 Baths
  • 19,569 Sq Ft

  1131 Sasco Hill Rd, Fairfield, CT 06824

  Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding

  Andrew Whiteley Brown Harris Stevens

  1131 Sasco Hill Rd, Fairfield, CT 06824
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  /38

  $650,000

  • 3 Beds
  • 2 Baths
  • 1,001 Sq Ft

  60 Meadowbrook Rd, Fairfield, CT 06824

  Coastal Charm Meets Modern Luxury in Fairfield, CT Looking for that perfect mix of classic charm and modern sophistication? Welcome to this stunning brick beauty in the heart of Fairfield, where luxury meets effortless coastal living. From the moment you arrive, you'll be captivated by the beautifully landscaped yard, framed by an elegant stone wall and a paver-lined driveway leading to a

  Marrisa Gilbertie Keller Williams Prestige Prop.

  60 Meadowbrook Rd, Fairfield, CT 06824
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  /5

  $2,350,000

  • 1 Bed
  • 1 Bath
  • 767 Sq Ft

  238 Hillspoint Rd, Westport, CT 06880

  Experience the pinnacle of waterfront living with this unique opportunity to custom design and build your dream beach house on the tranquil shores of Long Island Sound. With direct water frontage, this exceptional property offers breathtaking, uninterrupted views of the Sound and the iconic Old Mill Beach. Envision starting your day with a serene sunrise over the water, taking a refreshing

  Karen Scott Compass Connecticut, LLC

  238 Hillspoint Rd, Westport, CT 06880
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  /40

  $4,375,000

  • 6 Beds
  • 11 Baths
  • 10,414 Sq Ft

  5 Boxwood Ln, Westport, CT 06880

  Refined living awaits on Boxwood Lane, a prime Hunt Club cul-de-sac featuring tranquil private entrances to stately colonial style homes. From its cobblestone-lined, semi-circular driveway to the backyard pool and bluestone patio oasis, the grounds of 5 Boxwood Lane are simply spectacular. The home itself stands apart, meticulously designed with exquisite details and custom amenities. Four

  Karen Scott Compass Connecticut, LLC

  5 Boxwood Ln, Westport, CT 06880
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  /10

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,460 Sq Ft

  500 Dewey St, Bridgeport, CT 06605

  Please DO NOT DISTURB the occupant. Contact with occupants is prohibited. Opportunity to own a charming colonial-style home constructed in 1937. Offering over 1,400 square feet of living space, features 3 bedrooms and 1 full bathroom. This property includes the added benefit of off-street parking, ensuring ease and accessibility. Step outside into your own private fenced backyard ideal for family

  Jonathan Gineo Silver and Oak Realty

  500 Dewey St, Bridgeport, CT 06605

Showing Results 81 - 120, Page 3 of 4