Southport, CT Homes for Sale with Acreage

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  /40

  $2,995,000

  • 5 Beds
  • 5.5 Baths
  • 5,965 Sq Ft

  2015 Redding Rd, Fairfield, CT 06824

  Majestically sited on 2 private acres of professionally landscaped grounds, this exceptional SMART modern farmhouse surpasses new construction standards with uncompromising attention to detail. This 5,500+ SF estate exemplifies architectural integrity with handcrafted millwork and bespoke finishes throughout. Superior craftsmanship shines in every detail-from rich white oak hardwood floors to

  

  Susan Lieberman

  The Riverside Realty Group

  (475) 252-9450

  2015 Redding Rd, Fairfield, CT 06824
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  /5

  $4,895,000 New Construction

  • 6 Beds
  • 9 Baths
  • 9,224 Sq Ft

  21 Warnock Dr, Westport, CT 06880

  Expected for completion Fall 2025, this striking architectural design meets refined luxury in a meticulously crafted 9,200+/- sq ft, 6-bedroom, 6 full, & 3 half bath new residence. Showcasing the collaborative excellence of AR Luxury Homes w/ interior design by Mary Beth Woods & architectural vision by Donald William Fairbanks, this exceptional property represents the pinnacle of modern

  

  Brett Lieberman

  The Riverside Realty Group

  (475) 255-6647

  21 Warnock Dr, 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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  /40

  $3,895,000

  • 4 Beds
  • 3.5 Baths
  • 3,418 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

  Julie Vanderblue Higgins Group Real Estate

  61 Clapboard Hill Rd, Westport, CT 06880
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  /40

  $3,950,000

  • 5 Beds
  • 7 Baths
  • 5,771 Sq Ft

  116 Roseville Rd, Westport, CT 06880

  Tucked away on a picturesque property with a peaceful pond and complete privacy, this custom-built home is truly exceptional. From the moment you step onto the welcoming front porch, you'll feel the warmth and quality throughout. The sunlit kitchen is beautifully appointed with top-of-the-line appliances and a built-in banquette by the cozy fireplace, opening seamlessly to the inviting family

  Julie Vanderblue Higgins Group Real Estate

  116 Roseville Rd, Westport, CT 06880
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  /40

  $3,750,000

  • 7 Beds
  • 9 Baths
  • 10,104 Sq Ft

  249 Greens Farms Rd, Westport, CT 06880

  Storied and superbly restored, 'The Lookout' at 249 Greens Farms Rd blends the grandeur of a 1907 Victorian with todays modern luxury. Privately set among perennial gardens and antique copper beeches, this iconic 16-room residence offers a gracious floor plan with elegant formal spaces, a chefs eat-in kitchen, media room, wine cellar, and inviting family areas. Original architectural details

  Kim Harizman Compass Connecticut, LLC

  249 Greens Farms Rd, Westport, CT 06880
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  /40

  $5,500,000

  • 6 Beds
  • 9 Baths
  • 9,601 Sq Ft

  10 Debra Ln, Westport, CT 06880

  Stunning 6 Bedroom 9600SF (including all 4 levels) Colonial in the heart of Westport. Built by Bluewater Home Builders, this stunning custom residence is situated on a private cul-de-sac in the central Hunt Club area. The traditional design boasts exceptional interior details, including soaring ceilings, beamed and coffered accents, shiplap paneling, and sleek millwork throughout all finished

  Linda Skolnick Coldwell Banker Realty

  10 Debra Ln, Westport, CT 06880
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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 chef's

  Cindy Raney Coldwell Banker Realty

  2281 Redding Rd, Fairfield, CT 06824
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  /39

  $3,500,000

  • 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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  /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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  /40

  $3,550,000

  • 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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  /14

  $3,395,000

  • 5 Beds
  • 4.5 Baths
  • 5,056 Sq Ft

  16 Burr School Rd, Westport, CT 06880

  A masterful full renovation by acclaimed Coastal Luxury Homes, this extraordinary modern residence redefines sophistication in the heart of Westport. Set on a pristine, private acre on a coveted cul-de-sac, the home dazzles with soaring ceilings, dramatic walls of glass, and exquisite luxury finishes throughout. Designed for the way you live today, it offers two primary suite options, an

  Danna Rogers Higgins Group Bedford Square

  16 Burr School Rd, Westport, CT 06880
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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. "Sturges Manor" is an exceptional 6-bedroom, 8-bath estate that offers a rare combination of privacy, elegance, and resort-style amenities - just minutes from the Post Road and 50 miles from NYC. Enjoy multiple town centers and restaurants. The house features expansive, sun-filled interiors ideal for everyday living and entertaining. Recently

  Andrew Whiteley Brown Harris Stevens

  1084 Sturges Hwy, 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

  $4,600,000

  • 4 Beds
  • 3.5 Baths
  • 4,636 Sq Ft

  87 Red Coat Rd, Westport, CT 06880

  MOST UNIQUE HOUSE IN WESTPORT LARGE LOG HOME ON THE RIVER THAT IS STOCKED WITH TROUT. INGROUND GUNITE POOL BEAUTIFUL GROUNDS VERY PRIVATE ONE FLOOR LIVING. 4 BEDROOMS 3.5 BATHS. 1 HOUR TO NYC BEACH ACCESS. WONDERFUL RARE OPPORTUNITY TO OWN THE HOME YOU HAVE ALWAYS WONDERED ABOUT. THE BEAUTIFUL TRANQUIL RIVERVIEW LODGE LOG HOME THAT SITS ON THE MAJESTIC SAUGATUCK RIVER. WITH OVER 500+ FEET OF

  Rebecca Ellsley Higgins Group Bedford Square

  87 Red Coat Rd, Westport, CT 06880
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  /9

  $3,750,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,000 Sq Ft

  22 Brett Rd, Fairfield, CT 06824

  Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among

  Andrew Whiteley Brown Harris Stevens

  22 Brett Rd, Fairfield, CT 06824
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  /26

  $3,999,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 5,710 Sq Ft

  13 Terhune Dr, Westport, CT 06880

  Welcome to this beautifully crafted new construction home in the heart of Westport, where timeless design and thoughtful details come together to create a luxurious space. From the moment you step inside, you're welcomed by a bright and open floor plan with high ceilings and wide-plank flooring that runs throughout the main living space. Natural light fills every room, highlighting the custom

  Sara Santos Coldwell Banker Realty

  13 Terhune Dr, Westport, CT 06880
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  /31

  $1,999,000

  • 3 Beds
  • 2.5 Baths
  • 2,844 Sq Ft

  24 Warnock Dr, Westport, CT 06880

  Located in one of Westport's most desirable Coleytown neighborhoods surrounded by multi-million dollar homes 24 Warnock is the perfect blend of style comfort & convenience This turnkey 2851sf home on 4 floors offers close proximity to Westport's top rated schools vibrant downtown & beautiful beaches-an exceptional opportunity at this price point Thoughtfully renovated & impeccably maintained this

  Elaine Schanzenbach William Raveis Real Estate

  24 Warnock Dr, Westport, CT 06880
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  /40

  $1,899,000

  • 4 Beds
  • 2.5 Baths
  • 4,237 Sq Ft

  5 Willow Walk, Westport, CT 06880

  SELLER IS REQUESTING HIGHEST AND BEST OFFERS BE SUBMITTED BY SUNDAY, NOVEMBER 23RD AT 8PM. Nestled on a quiet, picturesque cul-de-sac, this beautifully maintained home enjoys a prime Westport location-just steps from Staples High School and Bedford Middle School, with direct gated access for ultimate convenience. A short drive brings you to all the amenities Westport has to offer, from shopping

  Wendy Ryan Brown Harris Stevens

  5 Willow Walk, Westport, CT 06880
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  /6

  $7,995,000

  • Land
  • 12.3 Acres
  • $650,000 per Acre

  109 Morningside Dr S, Westport, CT 06880

  109 Morningside Drive South is an exceptional and rare offering in the highly sought- after Greens Farms neighborhood in Westport CT. Spanning 12.3 acres, this expansive property presents a unique opportunity to create a one-of-a-kind estate in one of Fairfield county's most desirable locations. Nestled amongst prestigious homes, this property offers endless potential for those seeking to build

  Jenny Bentley The Riverside Realty Group

  109 Morningside Dr S, Westport, CT 06880
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  /24

  $1,699,000

  • 4 Beds
  • 2.5 Baths
  • 3,074 Sq Ft

  42 Kings Hwy S, Westport, CT 06880

  Step into this beautifully renovated modern home, where refined craftsmanship meets contemporary elegance. The grand foyer opens to a stunning living room with soaring double-height ceilings and a dramatic floor-to-ceiling stone fireplace. The gourmet chef's kitchen impresses with custom cabinetry, Viking appliances, quartz countertops, and a spacious eat-in area. Designed for effortless

  Dannel Malloy NestSeekers International

  42 Kings Hwy S, Westport, CT 06880
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  /40

  $9,495,000

  • 6 Beds
  • 11 Baths
  • 11,445 Sq Ft

  5 Hidden Hill Rd, Westport, CT 06880

  Stunning, one-of-one custom home on a private Compo Beach hilltop with sweeping views of Long Island Sound. This Lucien Vita estate was comprehensively refurbished in 2024 to include designer paint treatments, wall coverings, all new lighting and custom window treatments. Luxurious spaces merge impeccable architectural detail and craftsmanship to create distinctive indoor and outdoor living on 4

  Cyd Hamer William Pitt Sotheby's Int'l

  5 Hidden Hill Rd, Westport, CT 06880
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  /40

  $2,850,000

  • 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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  /40

  $2,799,999

  • 5 Beds
  • 6.5 Baths
  • 7,269 Sq Ft

  342 Midlock Rd, Fairfield, CT 06824

  Welcome to an unrivaled sanctuary of sophistication at 342 Midlock Road, gracefully situated in the prestigious enclave of Greenfield Hill. This stately residence, perched on a coveted cul-de-sac off Burr Street, unfurls over two lush acres of meticulously manicured, fully fenced grounds. Upon entry, be enveloped in luxury as you traverse through spaces adorned with custom millwork, nine ft

  AJ Letterman Compass Connecticut, LLC

  342 Midlock Rd, Fairfield, CT 06824
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  /39

  $1,100,000

  • 3 Beds
  • 3 Baths
  • 3,670 Sq Ft

  2190 Sturges Hwy, Westport, CT 06880

  Welcome to Pepperidge Acres - a unique enclave of four homes tucked away on a private cul-de-sac ideally located on the Westport line. Conveniently to both Westport & Fairfield town amenities, this classic home sits peacefully on two level acres, offering a serene and picturesque setting. Step into the grand living room featuring a vaulted ceiling and a dramatic floor-to-ceiling, double-sided

  Jeanne Bracken Coldwell Banker Realty

  2190 Sturges Hwy, Westport, CT 06880
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  /36

  $7,995,000

  • 5 Beds
  • 7 Baths
  • 4,998 Sq Ft

  775 Sasco Hill Rd, Fairfield, CT 06824

  Exceptional listing at 775 Sasco Hill Road - a home that seamlessly blends timeless elegance with modern luxury. Completely updated and impeccably decorated by the current owners, this residence offers three full levels of sophisticated living. Upon entering, you're greeted by a stunning cathedral ceiling in the foyer, with 9-foot ceilings throughout the main levels that create an airy, open

  Suzy Ryan William Raveis Real Estate

  775 Sasco Hill Rd, Fairfield, CT 06824
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  /40

  $2,498,000

  • 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
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  /40

  $2,785,000

  • 4 Beds
  • 3.5 Baths
  • 5,434 Sq Ft

  6 Nutcracker Ln, Westport, CT 06880

  A rare Westport retreat blending serenity, sophistication & resort-style living. Privately set at the end of a quiet cul-de-sac off Bayberry Lane, this elegant four-bedroom, three-and-a-half-bath home offers over 4,600 sq ft of sun-filled living space surrounded by beautifully landscaped grounds. The property's two private acres feel like a personal park-complete with mature trees, curated

  Michelle Sperry Coldwell Banker Realty

  6 Nutcracker Ln, Westport, CT 06880
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  /36

  $2,999,999

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

  3 Country Rd, Westport, CT 06880

  Located in the heart of one of Westports most coveted walk to town cul-de-sac locations on 1+ac. This sun-drenched 6 bdrm home blends timeless charm w/sophisticated modern renovations. Spanning over 5,000 sqft on stunning flat lush 1.02ac lot this home is perfectly situated for live-in child care/extended family members and effortless entertaining.Step inside to a reimagined custom kitchen

  Elizabeth Forrest Douglas Elliman of Connecticut

  3 Country Rd, Westport, CT 06880
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  /28

  $19,800,000

  • 8 Beds
  • 8.5 Baths
  • 9,995 Sq Ft

  92 Beachside Ave, Westport, CT 06880

  Once-in-a-Generation Historic Estate set on a most coveted stretch of Fairfield County's Gold Coast, with a remarkable provenance as a former Bedford family estate. This extraordinary property is a rare offering that blends timeless architecture with iconic waterfront living. With sweeping views of Long Island Sound, the home's stately presence is matched only by its stunning 3.55 acres of

  Cyd Hamer William Pitt Sotheby's Int'l

  92 Beachside Ave, Westport, CT 06880
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  /11

  $1,699,900

  • 3 Beds
  • 2 Baths
  • 3,171 Sq Ft

  40 Maple Ave N, Westport, CT 06880

  Prime location a few houses down from the Hunt Club three bedrooms with two additional bounus rooms and two bathrooms home with a fully finished walkout on a level one acre of land surrounded by multi million dollars homes.

  Sayed Ibrahim Nationwide Homes

  40 Maple Ave N, Westport, CT 06880
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  /40

  $1,695,000

  • 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

  $2,195,000

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

  17 Clover Ln, Westport, CT 06880

  SOPHISTICATED CONTEMPORARY RETREAT - CLOVER LANE Exciting opportunity to own a beautifully reimagined Contemporary home on an expansive 1.27 acres at the end of a peaceful Westport cul-de-sac. This thoughtfully renovated 3000 square-foot residence features open concept living areas with streaming natural light and captivating views of mature lush greenery. A sleek, designer kitchen serves as the

  Lisa Hartmann William Pitt Sotheby's Int'l

  17 Clover Ln, Westport, CT 06880
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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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  /14

  $1,169,000

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

  14 Northfield Dr, Westport, CT 06880

  Amazing opportunity! Move Right In or Renovate this Spacious 3BR Ranch in wonderful Coleytown neighborhood. Spacious 3BR one floor living with an open 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 be in A+ location! House is being sold as is.

  Deirdre Andreoli Compass Connecticut, LLC

  14 Northfield Dr, Westport, CT 06880
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  /30

  $2,065,000

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

  158 Coventry Ln, Fairfield, CT 06824

  Discover this Connecticut Colonial 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 ensures your peace of mind. Inside, the

  Veronica Monahan Compass Connecticut, LLC

  158 Coventry Ln, Fairfield, CT 06824
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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
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  /14

  $749,000

  • Land
  • 1.02 Acres
  • $734,314 per Acre

  844 Mill Hill Terrace, Fairfield, CT 06890

  This 1.02 acre parcel offers the rare combination of privacy and premier location. Tucked away in a quiet Southport neighborhood, yet just minutes to the harbor, beaches, train, restaurants, and charming village shops - it's the best of both worlds. The possibilities are endless - City water, City sewer and Natural Gas are available in the street. Whether you envision a timeless New England

  Barbara Sweeney Coldwell Banker Realty

  844 Mill Hill Terrace, Fairfield, CT 06890
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  /18

  $1,800,000

  • 4 Beds
  • 2 Baths
  • 1,925 Sq Ft

  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 or rebuild 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 secluded acres, are

  Harriet Stone William Pitt Sotheby's Int'l

  20 Ermine St, Fairfield, CT 06824
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  /40

  $2,850,000

  • 6 Beds
  • 8 Baths
  • 7,354 Sq Ft

  19A Darbrook Rd, Westport, CT 06880

  Discover this stunning 6-bedroom single-family home-a modern masterpiece designed for today's lifestyle. Perched on a private cul-de-sac just minutes from downtown Westport, dog parks, beaches, award-winning restaurants, and even a 24-hour CVS for those late-night essentials, this residence perfectly blends convenience with serenity. Step inside and experience Westport luxury redefined-a striking

  Nanci Lewis Keller Williams Realty

  19A Darbrook Rd, Westport, CT 06880

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