Southport, CT Homes for Sale

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  /38

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 2,556 Sq Ft

  4 Highland Rd, Westport, CT 06880

  Welcome to this timeless Colonial in sought-after Coleytown, where modern living meets classic charm. Move in before the holidays and enjoy over 2 acres of lush privacy with large composite deck and yard in this sought after cul-de-sac neighborhood. Step inside the craftsman-style entry to a welcoming center hall framed by hardwood floors and airy sight-lines that flow seamlessly from front to

  Kim Tromba Keller Williams Realty

  4 Highland Rd, Westport, CT 06880
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  /33

  $580,000

  • 6 Beds
  • 2.5 Baths
  • 2,579 Sq Ft

  1158 Howard Ave, Bridgeport, CT 06605

  Fully remodeled Multifamily with Two Spacious Units! The first floor offers 2 bedroom unit, a living room, kitchen with pantry, and full bath. The second & third floor unit features 4 bedrooms, a large living room, family room, bright office, kitchen with pantry, and 1.5 baths. Recent upgrades include brand new roof, windows, kitchen, bathrooms, flooring, doors, appliances, outlets & lights,

  Stephanie Ferreira BHGRE Gaetano Marra Homes

  1158 Howard Ave, Bridgeport, CT 06605
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  /40

  $4,435,000

  • 4 Beds
  • 4 Baths
  • 4,446 Sq Ft

  11 Sterling Dr, Westport, CT 06880

  Nestled in privacy by nearly 100 arborvitaes, this ultimate retreat on a rare double lot is just steps from Old Mill Beach & Compo Beach. The home distinguishes itself by offering water views from nearly every room & from the expansive decks located on multiple levels. Fully remodeled & expanded in 2018, this thoughtfully designed home features oversized windows to enjoy spectacular sunrises &

  Janice McGrath O'Brien William Raveis Real Estate

  11 Sterling Dr, Westport, CT 06880
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  /40

  $1,695,000 Open Sun 12PM - 2PM

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

  101 Brambley Hedge Cir, Fairfield, CT 06824

  Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury

  Akenmisire Musa The Agency

  101 Brambley Hedge Cir, Fairfield, CT 06824
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  /39

  $1,539,000

  • 5 Beds
  • 4.5 Baths
  • 4,073 Sq Ft

  1207 Stillson Rd, Fairfield, CT 06824

  Come home to your own private retreat tucked away in the sought after University area location and settle right in to enjoy the holidays! Over 4,000 sq ft of living area along with an exceptionally designed flexible floor plan featuring 5 bedrooms, 4.5 bathrooms, custom culinary kitchen including quartz countertops, Z Line appliances, butler's pantry and dining area with fireplace. Open concept 2

  John Hackett William Raveis Real Estate

  1207 Stillson Rd, Fairfield, CT 06824
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  /39

  $775,000

  • 4 Beds
  • 2 Baths
  • 2,376 Sq Ft

  221 Hunyadi Ave, Fairfield, CT 06824

  Beautifully maintained brick two-family in Fairfield's sought-after Holland Hill neighborhood. Each unit features 2 bedrooms plus a heated extra room-ideal for a third bedroom, office, or flex space. The first-floor unit is move-in ready; the second floor is occupied and will transfer with the sale. Both units offer hardwood floors, updated kitchens with quartz countertops, subway tile

  amaryllis rodriguez RE/MAX Right Choice

  221 Hunyadi Ave, Fairfield, CT 06824
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  /40

  $1,689,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 3,159 Sq Ft

  226 Ruane St, Fairfield, CT 06824

  Welcome to your dream come true lifestyle in the heart of Fairfield's coveted beach/town community-where coastal charm meets everyday convenience. This brand-new modern Colonial is more than a home, it's an upgraded living experience. Imagine morning walks to South Pine Creek Beach, afternoons on the tennis courts or golf course & evenings dining at vibrant restaurants, live music & theatres

  Julie Vanderblue Higgins Group Real Estate

  226 Ruane St, Fairfield, CT 06824
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  /39

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,104 Sq Ft

  26 Crescent Park Rd, Westport, CT 06880

  Welcome to this beautifully maintained single-family home offering 3 bedrooms and 2 full bathrooms, with hardwood floors throughout, perfectly move-in ready, this home provides comfortable living with a thoughtful layout, over 1100 sq ft, a great condo alternative. Located in the heart of Westport, you'll enjoy convenient access to all the town's amenities-shops, restaurants, beaches, and

  Karim Douich William Raveis Real Estate

  26 Crescent Park Rd, Westport, CT 06880
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  /18

  $899,000

  • 4 Beds
  • 3 Baths
  • 2,912 Sq Ft

  153 Longview Ave, Fairfield, CT 06824

  Live and invest in the heart of Fairfield, CT - Fantastic opportunity to own a duplex in a prime location. This newly updated 2-family home offers a great combination of modern living and investment potential. Main unit features 3 bedrooms and 2 full baths, with recent renovations that include new hardwood floors and central air. The updated eat-in kitchens are a chef's delight, complete with

  Christine Ricci Keller Williams NY Realty

  153 Longview Ave, Fairfield, CT 06824
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  /40

  $4,995,000

  • 5 Beds
  • 4.5 Baths
  • 4,191 Sq Ft

  2281 Redding Rd, Fairfield, CT 06824

  Feels like Litchfield. Lives like Fairfield. Tucked behind a private gate in Greenfield Hill, this estate offers what few properties can: sweeping space, true privacy, and serene beauty-just 60 miles from Manhattan. A long stone drive leads to the 1941 main residence, reimagined with timeless craftsmanship. Sunlight floods rooms finished with reclaimed wood beams and wide-plank floors. The

  Cindy Raney Coldwell Banker Realty

  2281 Redding Rd, Fairfield, CT 06824
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  /33

  $1,775,000

  • 3 Beds
  • 2.5 Baths
  • 1,805 Sq Ft

  7 Wild Rose Rd, Westport, CT 06880

  Every plank, beam, and finish in this 3BR, 2.5 bath was selected with intention. A masterclass in design with warmth, quality, and craftsmanship in every detail, and finishes typically reserved for homes at much higher price points. Reimagined by Alex Brandfon, founder of ZIBA Hardwoods, the home reflects a vision of luxury and ease, where reclaimed character and modern precision come together

  Cindy Raney Coldwell Banker Realty

  7 Wild Rose Rd, Westport, CT 06880
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  /12

  $699,000

  • 6 Beds
  • 3 Baths
  • 3,069 Sq Ft

  195 Lenox Ave Unit 197, Bridgeport, CT 06605

  Welcome to 195 Lenox Avenue - a modern and versatile 3-family home perfect for both investors and first-time buyers. With 6 bedrooms, 3 full bathrooms, and a full basement, this property offers plenty of space and excellent rental potential. The first and second floors each allow for an extra bedroom conversion, maximizing cash flow. Inside, the units are updated and well-maintained, providing

  Shafran Salim Guy Bocicaut Real Estate

  195 Lenox Ave Unit 197, Bridgeport, CT 06605
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  /23

  $520,000

  • 6 Beds
  • 2 Baths
  • 2,099 Sq Ft

  1059 Hancock Ave Unit 1061, Bridgeport, CT 06605

  Welcome to this exceptional multi-family property located in the highly sought-after West End of Connecticut! This building presents a fantastic investment opportunity with easy access to public transportation, local stores, and major highways, making it ideal for both tenants and owners alike. The property features spacious units with ample natural light, providing a comfortable living

  Oswaldo Torres Las Americas Real Estate

  1059 Hancock Ave Unit 1061, Bridgeport, CT 06605
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  /33

  $1,149,000

  • 4 Beds
  • 3.5 Baths
  • 5,081 Sq Ft

  480 Riders Ln, Fairfield, CT 06824

  Welcome to 480 Riders Lane, a timeless mid-century contemporary residence situated at the end of a charming cul-de-sac in the desirable Greenfield Hill neighborhood. This home features 4 to 5 bedrooms and 4 updated bathrooms, offering over 5,000 square feet of carefully crafted living space on a beautiful 2-acre lot, complete with a peaceful pond and fountain. Upon arrival, you'll be welcomed by

  Courtney McManus The Agency

  480 Riders Ln, Fairfield, CT 06824
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  /39

  $1,495,000

  • 5 Beds
  • 2.5 Baths
  • 3,469 Sq Ft

  478 Crestwood Rd, Fairfield, CT 06824

  Classic Colonial in Prime University Area Location. This 1937 Colonial offers four finished levels of living space and a rare combination of character, flexibility, and outdoor living-all set on one of the University Area's most desirable streets. The interior features a thoughtful blend of formal and casual spaces, providing the ideal layout for both everyday living and entertaining. Original

  Wendy Ryan Brown Harris Stevens

  478 Crestwood Rd, Fairfield, CT 06824
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  /31

  $3,499,000

  • 6 Beds
  • 6.5 Baths
  • 7,899 Sq Ft

  3 Bolton Ln, Westport, CT 06880

  This beautiful home with undeniable curb appeal crafted by Andy Frank, sits on a flat, centrally located acre in the heart of Westport. Designed with light-filled spaces and an open, eat in kitchen, the home is finished across 4 levels, offering versatile living for today's lifestyle. The primary suite flows into a large sitting area with a lovely deck overlooking the pristine backyard. Enjoy 5

  Jen Kass Higgins Group Bedford Square

  3 Bolton Ln, Westport, CT 06880
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  /10

  $340,000

  • 6 Beds
  • 2 Baths
  • 1,920 Sq Ft

  1050 Hancock Ave Unit 1052, Bridgeport, CT 06605

  Investment opportunity awaits with this spacious multi-family property featuring two up-and-down units. Offering just under 2,000 square feet of total living space, each unit includes 3 bedrooms and 1 full bathroom ideal for rental income or multi-generational living. Residents will appreciate the convenience of off-street parking and the added bonus of a fully fenced front and backyard,

  Jonathan Gineo Silver and Oak Realty

  1050 Hancock Ave Unit 1052, Bridgeport, CT 06605
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  /38

  $4,000,000

  • 5 Beds
  • 6.5 Baths
  • 5,789 Sq Ft

  221 Greens Farms Rd, Westport, CT 06880

  THE BEDFORD HOUSE - Architecturally and historically significant estate in coveted Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's most superb homes. Set on 2.33 acres with a gunite pool/spa, court and a 2400 sq ft barn featuring a 3-car garage, loft & more, the estate blends timeless elegance with modern comfort. Originally built in 1904 and designed by

  Leslie Riback Coldwell Banker Realty

  221 Greens Farms Rd, Westport, CT 06880
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  /14

  $1,169,000

  • 3 Beds
  • 2 Baths
  • 1,813 Sq Ft

  14 Northfield Dr, Westport, CT 06880

  PLEASE present ALL OFFERS by Sunday, Sept. 21st, 5:00pm. Amazing opportunity to live in desirable Coleytown neighborhood. Spacious Ranch with an open kitchen/living floorpan and light filled sunroom (extra 322 sqft not included in total footage) 3 bedrooms, and 2 full baths with pool. Flat yard walking distance to elementary and middle school. Wonderful chance to move right in, renovate and

  Deirdre Andreoli Compass Connecticut, LLC

  14 Northfield Dr, Westport, CT 06880
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  /37

  $1,275,000

  • 2 Beds
  • 2.5 Baths
  • 2,050 Sq Ft

  144 Lansdowne Unit 144, Westport, CT 06880

  One of the most sought-after complexes in Westport, Lansdowne offers the perfect blend of comfort, security, convenience, and luxury. This spacious home with a highly desired first-floor Primary Suite is bathed in natural light and designed to provide the feel of single-family living while enjoying the benefits of a condominium community. The main level features a welcoming foyer, an eat-in

  Amy Waugh Curry ABR CRS GRI Berkshire Hathaway NE Prop.

  144 Lansdowne Unit 144, Westport, CT 06880
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  /15

  $899,999

  • 3 Beds
  • 1.5 Baths
  • 1,224 Sq Ft

  196 Catherine Terrace, Fairfield, CT 06824

  Nestled close to picturesque beaches, downtown with its award-winning restaurants, and Metro North trains, this charming home is a rare find, offered in as-is condition by the original family owner. A perfect canvas for those looking to create their dream beach area home, with ample potential to modernize and make it your own

  Jim Stobie Berkshire Hathaway NE Prop.

  196 Catherine Terrace, Fairfield, CT 06824
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  /16

  $529,900

  • 4 Beds
  • 2 Baths
  • 1,994 Sq Ft

  51 Princeton St, Bridgeport, CT 06605

  Great Black Rock two family home, both apartments are in good condition and has been well maintained, the rear yard offers good off street parking. It is conveniently located in walking distance to the Black Rock Train Station, Restaurants, Pubs, Music Venues, Waterfront Social Clubs, St. Mary's By The Sea and is minutes to I-95. Tenants are month to month.

  John Kleps Berkshire Hathaway NE Prop.

  51 Princeton St, Bridgeport, CT 06605
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  /40

  $1,179,999

  • 4 Beds
  • 3 Baths
  • 2,012 Sq Ft

  115 Mayfair Rd, Fairfield, CT 06824

  Welcome to 115 Mayfair Road This stunning 4-bedroom, 3-bath home has been fully renovated, right down to the studs, with top-quality finishes and thoughtful design. Step inside to find gleaming plank white oak hardwood floors and an open-concept layout that seamlessly connects the living room, dining area, and chef's kitchen. The gourmet kitchen is a true showpiece with sleek black onyx quartz

  Kenny Bascon Real Broker CT, LLC

  115 Mayfair Rd, Fairfield, CT 06824
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  /23

  $515,000

  • 4 Beds
  • 4 Baths
  • 2,045 Sq Ft

  90 2nd St, Fairfield, CT 06825

  Nestled on a quiet street in Fairfield's Tunxis Hill neighborhood, this spacious 4-bedroom residence offers comfort, and convenience. Featuring 2 full baths and 2 half baths, the home has engineered hardwood floors throughout the kitchen, living room, and dining room, with easy-care vinyl laminate in the bedrooms. The fully fenced yard provides a private outdoor space. Please note: all MLS

  Jaime Pote Coldwell Banker Realty

  90 2nd St, Fairfield, CT 06825
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  /40

  $1,399,000

  • 4 Beds
  • 4.5 Baths
  • 4,590 Sq Ft

  327 Lucille St, Fairfield, CT 06825

  Few things are more inviting than a front porch, and 327 Lucille St delivers that and more in terms of curb appeal, which this home has in spades. This Colonial pairs classic architectural beauty with almost 5,000 sq ft across 4 levels, offering 4 bedrooms, an office, 4.5 baths, 2 car garage, and a fenced-in .46 acre yard. Inside, the foyer is flanked by the dining and living rooms, both with

  Sarah Pritchard William Raveis Real Estate

  327 Lucille St, Fairfield, CT 06825
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  /37

  $1,749,000 Open Sun 2:30AM - 4:30PM

  • 4 Beds
  • 3.5 Baths
  • 3,397 Sq Ft

  61 Edgewater Commons Ln, Westport, CT 06880

  COMPO BEACH NEIGHBORHOOD * WATER VIEWS * ROOM FOR A POOL This coastal gem sits on one of the largest lots near Compo Beach and has been thoughtfully renovated by skilled artisans and craftsmen, combining beachside charm with modern comfort. Located at the end of a quiet cul-de-sac, the property features equestrian fencing leading to an oil-and-stone driveway and a flat, partially fenced yard with

  Maria Tziolis William Pitt Sotheby's Int'l

  61 Edgewater Commons Ln, Westport, CT 06880
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  /31

  $2,065,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 4,255 Sq Ft

  158 Coventry Ln, Fairfield, CT 06824

  Discover this Connecticut Colonial, now with a dramatic price improvement, nestled on a peaceful cul-de-sac. This gem sits on two acres of meticulously landscaped, flat grounds, free from wetlands, showcasing vibrant gardens, stone walls & bluestone walkways. Indulge in the heated saltwater pool and spa with a waterfall feature, and unwind in the inviting cabana/pool house. A full house generator

  Veronica Monahan Compass Connecticut, LLC

  158 Coventry Ln, Fairfield, CT 06824
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  /40

  $1,949,000

  • 6 Beds
  • 5.5 Baths
  • 3,847 Sq Ft

  45 Robin Cir, Fairfield, CT 06824

  Award-Winning Luxury in Fairfield! Recipient of the 2025 HOBI Award for Outstanding Fairfield County Spec Home $1-2 Million, 45 Robin Circle showcases timeless design, refined craftsmanship, and effortless livability. The sunlit main level features an open-concept chef's kitchen with professional appliances and an oversized island flowing to an elegant great room with fireplace and custom

  Jennifer DeLaurentis Compass Connecticut, LLC

  45 Robin Cir, Fairfield, CT 06824
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  /40

  $4,700,000

  • 8 Beds
  • 9 Baths
  • 8,412 Sq Ft

  32 Webb Rd, Westport, CT 06880

  This 2025 Colonial at 32 Webb Road offers 8,412 sq ft of open-concept living on a 0.64-acre lot. Eight bedrooms and nine bathrooms include a spacious primary suite with walk-in closet and private balcony. The gourmet kitchen features top-tier appliances and custom cabinetry, flowing seamlessly into sun-filled living and dining areas with high ceilings. Multiple living spaces allow flexible

  Judy Michaelis Coldwell Banker Realty

  32 Webb Rd, Westport, CT 06880
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  /40

  $3,649,000

  • 5 Beds
  • 4.5 Baths
  • 4,771 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 offers a rare opportunity in one of Fairfield's most coveted locations. Set on more than two acres of beautifully landscaped grounds with distant views of Long Island Sound, the property reflects timeless elegance and a sense of place that is hard to replicate today. Across from a distinguished

  Tara Hawley Coldwell Banker Realty

  2683 Bronson Rd, Fairfield, CT 06824
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  /33

  $389,900

  • 2 Beds
  • 2 Baths
  • 1,340 Sq Ft

  65 Ellsworth St Unit 302, Bridgeport, CT 06605

  Great two bedroom, two full bath end unit townhouse located steps to Black Rock Harbor and Seabright Beach! A new kitchen is being installed with white cabinets and white countertops, the unit has been freshly painted, new carpeting and new stove installed and is available for quick occupancy. The main level has an open kitchen and living room with a vaulted ceiling, bedroom, full bathroom and

  John Kleps Berkshire Hathaway NE Prop.

  65 Ellsworth St Unit 302, Bridgeport, CT 06605
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  /40

  $1,249,000

  • 2 Beds
  • 1.5 Baths
  • 1,424 Sq Ft

  1135 Mill Hill Rd, Southport, CT 06890

  The Sherwood Farmhouse set in Southport's Mill Hill area, Circa 1720, is tucked away on a picturesque .48-acre lot in an enchanting country setting. This beautifully preserved and thoughtfully updated historic treasure blends 18th-century charm with modern comforts. Original features such as wide plank floors, hand-hewn beams, custom cupboards, and three working fireplaces speak to the home's

  Amy Waugh Curry ABR CRS GRI Berkshire Hathaway NE Prop.

  1135 Mill Hill Rd, Southport, CT 06890
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  /40

  $3,750,000 Open Sun 12PM - 3PM

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

  111 Sturges Hwy, Westport, CT 06880

  Welcome to 111 Sturges Highway, the pinnacle of refined elegance and timeless design. A circular drive framed by majestic stone walls sets a distinguished tone upon arrival, while a second driveway provides access from a coveted quiet street. Graceful columns evoke the grandeur of a Southern mansion, while sweeping lawns and specimen plantings create a park-like setting that ensures privacy and

  Julie Vanderblue Higgins Group Real Estate

  111 Sturges Hwy, Westport, CT 06880
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  /34

  $985,000

  • 4 Beds
  • 2.5 Baths
  • 2,044 Sq Ft

  68 Center St, Westport, CT 06880

  Welcome to 68 Center Street - a rustic retreat nestled in beautiful Greens Farms. This character-rich 1920s Cottage, cherished by the same family for over 50 years, is now ready to begin a new chapter - with you. You will find charming nooks, thoughtful details and two wood burning fireplaces perfect for quiet mornings or hosting friends, on three finished levels. The glass solarium entry invites

  David Kinyon Coldwell Banker Realty

  68 Center St, Westport, CT 06880
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  /40

  $1,900,000

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

  305 S Gate Ln, Southport, CT 06890

  Tucked away on a serene street in the heart of Southport, this 4-bedroom, 4-bath Colonial invites you to experience the perfect balance of elegance, comfort, and privacy. From the moment you arrive, the home's setting feels special - an expansive property framed by mature trees, offering a sense of peace and seclusion. Step inside, and natural light floods the main level, where formal living and

  Elizabeth Tritschler William Raveis Real Estate

  305 S Gate Ln, Southport, CT 06890
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  /36

  $1,795,000

  • 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
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  /40

  $1,495,000

  • 4 Beds
  • 2.5 Baths
  • 3,597 Sq Ft

  153 Pease Ave, Southport, CT 06890

  Newly Renovated Colonial in Prime Southport Location. Beautifully updated colonial offering modern comfort and timeless style. Featuring a stunning new custom kitchen with a large center island, professional Thermador appliances, and separate butlers pantry, this home is perfect for both everyday living and entertaining. The open floor plan is filled with natural light and has 9ft ceilings

  Basil Amso RE/MAX Right Choice

  153 Pease Ave, Southport, CT 06890
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  /31

  $1,999,000

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

  137 Millard St, Fairfield, CT 06824

  Stunning NEW construction the desirable Fairfield Beach neighborhood. This gorgeous home is crafted by premier 43 year Fairfield County builder. Premium materials, thoughtful design, and masterful workmanship are showcased throughout. Step inside to find a clean lined, open living space with 9' ceilings. The inviting living room, featuring a captivating 54" cool wall gas fireplace, seamlessly

  Katie O'Grady Compass Connecticut, LLC

  137 Millard St, Fairfield, CT 06824
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  /40

  $1,999,999

  • 5 Beds
  • 3 Baths
  • 4,106 Sq Ft

  215 Old Post Rd, Fairfield, CT 06824

  Old Post Road perfection! Step on to the gracious front porch and be swept away by timeless architecture, graceful design and superb finishes. Beautifully renovated home with so many improvements/amenities including gorgeous expanded kitchen, renovated bathrooms, plantation shutters, new windows, new roof, fresh exterior paint, fencing and more. The inviting foyer welcomes you to a living room

  Katie O'Grady Compass Connecticut, LLC

  215 Old Post Rd, Fairfield, CT 06824
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  /38

  $739,900

  • 4 Beds
  • 3.5 Baths
  • 2,268 Sq Ft

  42 Fairway Green, Fairfield, CT 06825

  Charming and Fresh-Painted Colonial with Modern Upgrades. This freshly painted colonial home boasts 4 spacious bedrooms, 3.5 baths, a brand-new HVAC system, and a wood-burning fireplace. With 2268 sq ft of living space plus a 520 sq ft finished basement, it includes a large deck, an office or in-law suite and a tall 2-car garage. Built in 1987 on a 0.24-acre lot, this home is in a

  David White OwnerEntry.com

  42 Fairway Green, Fairfield, CT 06825

Showing Results 81 - 120, Page 3 of 6