Southport, CT Houses for Sale

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  /25

  $3,999,000

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

  57 Evergreen Ave, Westport, CT 06880

  Walk to downtown shops and restaurants from this stunning, reimagined, & rebuilt 1920 Dutch colonial home, situated on a spacious 1.17-acre in-town property.This is truly a work of art, as 2 properties have been seamlessly combined into one, creating a private oasis set way back from the road.Upon entering the home, you will be captivated by the meticulous attention to detail & the perfect blend

  

  Hyleri Katzenberg

  Compass Connecticut, LLC

  (475) 253-3404

  57 Evergreen Ave, Westport, CT 06880
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  /36

  $2,647,000

  • 4 Beds
  • 4.5 Baths
  • 3,935 Sq Ft

  11 Old Hill Rd, Westport, CT 06880

  Nestled in the heart of Westport's coveted Old Hill neighborhood, this home offers the charm of an English cottage and a thoughtful design that blends classic character with the modern desire for open, connected living. Encompassing nearly 4,000 square feet, it features four ensuite bedrooms, walk-in closets, and a curated layout that combines timeless architectural details with contemporary

  

  Susan Lieberman

  The Riverside Realty Group

  (203) 858-9411

  11 Old Hill Rd, Westport, CT 06880
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  /24

  $609,999

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

  449 High St, Fairfield, CT 06824

  Welcome to your dream home in the heart of Fairfield! This beautifully renovated 3-bedroom, 2-bathroom gem offers the perfect blend of classic charm and modern updates. Step inside to find a bright, open floor plan with gleaming hardwood floors, a brand-new kitchen featuring stainless steel appliances and quartz countertops, and two stylishly updated bathrooms. Enjoy morning coffee on the front

  

  Gary Crawford

  RE/MAX RISE

  (475) 252-5285

  449 High St, Fairfield, CT 06824
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  /2

  $4,895,000 New Construction

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

  21 Warnock Dr, Westport, CT 06880

  Expected for completion end of summer 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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  /34

  $849,900

  • 3 Beds
  • 2 Baths
  • 1,665 Sq Ft

  274 High St, Fairfield, CT 06824

  Welcome to 274 High Street, Fairfield, CT-where timeless elegance meets modern convenience. This beautifully renovated home boasts a fresh and inviting open-concept design, with a stunning new Trex deck just off the kitchen, perfect for relaxing or entertaining. The spacious kitchen features a large island with extra seating, complemented by a stylish design table for additional dining space.

  Karly Worth Call It Closed Realty

  274 High St, Fairfield, CT 06824
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  /36

  $1,795,000

  • 4 Beds
  • 2 Baths
  • 2,190 Sq Ft

  7 Morningside Ln, Westport, CT 06880

  A Westport treasure, this c.1900 beauty enchants with timeless charm and a magical warmth. Once the homestead of one of Westport's largest onion farms, you may still find one growing wild on the lawn. The wrap-around screened porch is perfect for summer mornings or unwinding at sunset. Inside, sunlit living spaces are filled with original character, and the chef's kitchen offers high-end

  Michelle Genovesi William Raveis Real Estate

  7 Morningside Ln, Westport, CT 06880
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  /40

  $3,750,000

  • 6 Beds
  • 7.5 Baths
  • 14,110 Sq Ft

  21 Queens Grant Dr, Fairfield, CT 06824

  Welcome to one of Greenfield Hill's most distinguished residences-an extraordinary 9,700+ sq. ft. Colonial estate nestled on 2 pristine acres in one of Fairfield's most prestigious enclaves. This 5-6 bedroom architectural masterpiece combines timeless elegance with modern luxury, offering an unparalleled lifestyle just moments from town. From first look, the home's unrivaled curb appeal

  Michael Debiase Keller Williams Realty

  21 Queens Grant Dr, Fairfield, CT 06824
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  /40

  $2,995,000

  • 4 Beds
  • 4.5 Baths
  • 5,629 Sq Ft

  166 Long Lots Rd, Westport, CT 06880

  Your private oasis awaits! This beautifully renovated home offers an ideal location with easy access to town, shopping, and the beach. Designed with comfort and style in mind, the home features inviting living spaces including a two-story family room with an open staircase. The gourmet eat-in kitchen is open to a sitting area with a corner fireplace. Two family bedrooms with en-suite baths

  Michelle Genovesi William Raveis Real Estate

  166 Long Lots Rd, Westport, CT 06880
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  /40

  $6,980,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,791 Sq Ft

  22 Apple Tree Trail, Westport, CT 06880

  PRICE ADJUSTED! Compo Beach living, 2 short blocks from beach on private road! Luxury construction, just completed. 5 bed, 4.5 bath modern home w/ all of the lush amenities seen in the finest resorts both inside & out. Custom Italian cabinetry by L'Ottocento in kitchen, butler's pantry, bathrooms, and mudroom. 9ft.+ ceilings, open stairs w/ glass railings & oak floors. Entry hall w/ crystal

  Deborah Aulfinger Goldan Home Realty, LLC.

  22 Apple Tree Trail, Westport, CT 06880
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  /40

  $2,399,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 3,157 Sq Ft

  260 Birch Rd, Fairfield, CT 06824

  Experience Coastal Luxury in this Brand New Custom Colonial just steps away from the soothing sands & sea breeze of Penfield Beach, featuring a brand-new pavilion for the ultimate Gold Coast lifestyle! Perfectly situated on one of Fairfield's most coveted streets, this FEMA-compliant custom home offers 4 Bedrooms, 3 Full bathrooms & over 3,000 square feet of thoughtfully designed living space

  Melissa Montagno Higgins Group Real Estate

  260 Birch Rd, Fairfield, CT 06824
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  /40

  $6,899,000

  • 4 Beds
  • 7 Baths
  • 5,979 Sq Ft

  195 Fairfield Beach Rd, Fairfield, CT 06824

  Introducing a breathtaking & architecturally striking waterfront estate on the Gold Coast - a treasure combining elevated design, top tier craftsmanship & smart luxury. Set on a rare .53 acre beachfront lot w/ 80+ ft of direct shoreline, this exceptional home offers 5,400sf of elegant living across 3 levels + a 560sf studio w/ a half bath - ideal for a guest suite or creative retreat. Wrapped in

  Jackie Davis William Raveis Real Estate

  195 Fairfield Beach Rd, Fairfield, CT 06824
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  /38

  $2,695,000

  • 4 Beds
  • 4 Baths
  • 3,076 Sq Ft

  158 Hillspoint Rd, Westport, CT 06880

  Discover this exceptional, cozy abode nestled in a coveted location just a leisurely stroll away from the beach. Boasting its very own charming guest cottage and delightful in-ground pool, this residence offers unparalleled warmth and hospitality, and promises to be a haven of relaxation and entertainment for all who visit. Steeped in history dating back to 1803, and most recently updated in

  Karen Liss-uomoleale William Raveis Real Estate

  158 Hillspoint Rd, Westport, CT 06880
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  /39

  $3,750,000

  • 5 Beds
  • 7 Baths
  • 6,406 Sq Ft

  12 Old Hill Farms Rd, Westport, CT 06880

  Beautifully renovated vintage home offers timeless character on a professionally landscaped acre in coveted Old Hill. With 5 bedrooms, 5 full and 2 half baths with generous space and classic charm. The formal living room and elegant library both with fireplaces and hardwood floors create a warm and welcoming space for relaxing and entertaining. A spacious kitchen featuring a large center island,

  Emily Gordon Coldwell Banker Realty

  12 Old Hill Farms Rd, Westport, CT 06880
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  /40

  $6,950,000

  • 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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  /40

  $5,725,000

  • 7 Beds
  • 9 Baths
  • 13,615 Sq Ft

  9 Greenbrier Rd, Westport, CT 06880

  Charming. Unique. Soulful. These are the words the current owner uses to describe this exceptional estate-and from the moment you arrive, you'll understand why. Poised on 2.85 private acres, this exceptional estate seamlessly weaves timeless heritage with modern luxury. At its core: a preserved 1930 Frazier Peters stone cottage-now a 2-bed, 2-bath guest house. At its heart: a 2007 custom-built

  Cindy Raney Coldwell Banker Realty

  9 Greenbrier Rd, Westport, CT 06880
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  /40

  $2,650,000

  • 5 Beds
  • 4.5 Baths
  • 3,703 Sq Ft

  2821 Congress St, Fairfield, CT 06824

  Located in the heart of Greenfield Hill, "Upper Meadow Farm" is a rare blend of timeless character and modern comfort. Originally dating back to 1835, this storied property at 2821 Congress Street has been thoughtfully expanded and updated over the years, most recently in 2019 by the current owners. The result is a warm, welcoming home where historic details meet a fresh, refined palette. A

  Andrew Whiteley Brown Harris Stevens

  2821 Congress St, Fairfield, CT 06824
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  /34

  $2,499,000

  • 5 Beds
  • 4.5 Baths
  • 4,847 Sq Ft

  3A Iris Ln, Westport, CT 06880

  Nestled on 2 private acres in a prime, convenient location, this impeccably maintained 5BR, 4.5 BA colonial offers a timeless elegance with modern comfort. Soaring 9-foot ceilings and an open floor plan create an airy, inviting atmosphere, while French doors lead to a stone terrace, cocktail pool and romantic perennial gardens-perfect for entertaining or peaceful relaxation. Inside, hardwood

  Emily Gordon Coldwell Banker Realty

  3A Iris Ln, 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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  /39

  $2,545,000 Open Sun 12PM - 2PM

  • 5 Beds
  • 4.5 Baths
  • 3,510 Sq Ft

  81 Birch Rd, Fairfield, CT 06824

  Live the ultimate coastal lifestyle in this sensational 5-6 bedroom, 4.5 bathroom Nantucket-style Colonial w/brand new Gunite pool. Set on an oversized, wide lot, this home was recently reimagined by one of Fairfield County's most acclaimed interior designers. Sun-flooded w/9' ceilings & a breezy beach-inspired layout, every detail feels custom & elevated: coffered ceilings, transom doorways,

  Kate Cacciatore William Raveis Real Estate

  81 Birch Rd, Fairfield, CT 06824
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  /34

  $2,599,000

  • 4 Beds
  • 4.5 Baths
  • 3,985 Sq Ft

  35 Millard St, Fairfield, CT 06824

  A Rare Opportunity in the Beach Area- Set on an oversized .42-acre lot at the end of a quiet cul-de-sac, this custom-built home offers a rare combination of space, quality, and location. Uniquely positioned with a deep front setback and an expansive backyard-this property stands apart from typical neighborhood lots. Ample room for a pool and more! Thoughtfully designed for both comfort and

  Wendy Ryan Brown Harris Stevens

  35 Millard St, Fairfield, CT 06824
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  /40

  $2,465,000

  • 4 Beds
  • 3 Baths
  • 4,412 Sq Ft

  8 Northfield Dr, Westport, CT 06880

  This is the perfect house in the perfect location-just minutes from top-rated schools, playgrounds, ballfields, and houses of worship. Set on a picture-perfect acre of lush, manicured lawn, this Colonial style home offers serene views of a large pond while overlooking 8+ acres of private, protected meadowland. A gas-fired, whole-house generator provides seamless backup power for year-round peace

  Helen Cusa Brown Harris Stevens

  8 Northfield Dr, Westport, CT 06880
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  /37

  $2,300,000

  • 4 Beds
  • 3 Baths
  • 2,695 Sq Ft

  19 Sherwood Dr, Westport, CT 06880

  Welcome to 19 Sherwood Drive, where beach lifestyle meets contemporary comfort in one of Westport's most desirable enclaves. This home is just a short stroll from the picturesque Old Mill Beach, offering the ultimate in coastal living. Step inside to a sun-drenched, open-concept first floor featuring a renovated kitchen ideal for both everyday living and entertaining. The main level also includes

  Kim Harizman Compass Connecticut, LLC

  19 Sherwood Dr, Westport, CT 06880
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  /40

  $2,649,000

  • 6 Beds
  • 4.5 Baths
  • 5,083 Sq Ft

  4 the Fenway, Westport, CT 06880

  Timeless elegance in Westport's prestigious Old Hill. First time on the market in 29 years! This expansive 5-6 bedroom, 4.5 bath farmhouse is gracefully set on 2.22 serene acres, featuring a heated gunite pool, picturesque pond, and a very rare blend of privacy and proximity to town. The sun-drenched primary suite is a true retreat with a fireplace, spa-like bath, and generous walk-in closet. A

  Mary Kate Klemish-Boehm Brown Harris Stevens

  4 the Fenway, Westport, CT 06880
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  /38

  $2,300,000 Open Sun 12PM - 2PM

  • 6 Beds
  • 5.5 Baths
  • 5,256 Sq Ft

  59 Thornhill Rd, Fairfield, CT 06824

  Located on one of the most coveted cul-de-sacs in Fairfield's University area, this Newly Built Colonial offers a perfect blend of classic charm & modern luxury. A welcoming stone-trimmed front porch sets the stage for quiet mornings with coffee, while inside, 5-7 bedrooms and 5.5 bathrooms provide ample space for comfortable living and entertaining. The gorgeous open-concept Kitchen with eating

  Julie Vanderblue Higgins Group Real Estate

  59 Thornhill Rd, Fairfield, CT 06824
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  /35

  $2,799,000

  • 4 Beds
  • 3 Baths
  • 3,156 Sq Ft

  11 Dogwood Ln, Westport, CT 06880

  Experience the best of Westport living in this stunning Mid Century Modern residence set on 1.87 prime acres in the heart of town. This is all about the property! Tucked away on a beautifully landscaped property, this 4-bedroom home offers the perfect blend of privacy, modern design, and everyday convenience. Inside, expansive windows bathe the open living spaces in natural light, with soaring

  Linda Skolnick Coldwell Banker Realty

  11 Dogwood Ln, Westport, CT 06880
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  /29

  $2,249,000

  • 4 Beds
  • 3 Baths
  • 4,231 Sq Ft

  10 Twin Falls Ln, Westport, CT 06880

  Beyond Beautiful - Welcome to 10 Twin Falls Lane, a striking property and home filled with natural light from floor-to-ceiling windows. Step into the sun-drenched foyer with terracotta tile. Throughout the years the home has been updated and modernized with soaring ceilings, serene views, and inspiring design. The expansive family room features a dramatic picture window and flows seamlessly into

  Kit Tingley Higgins Group Bedford Square

  10 Twin Falls Ln, Westport, CT 06880
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  /32

  $2,175,000

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

  137 Millard St, Fairfield, CT 06824

  Stunning NEW construction nestled in the desirable Fairfield Beach neighborhood. This fabulous home is crafted by premier Fairfield County builder with over 43 years of esteemed reputation and results. Premium materials, thoughtful design, and masterful workmanship are showcased throughout. Step inside to find a clean, modern, open living space with 9' ceilings. The inviting living room,

  Katie O'Grady Compass Connecticut, LLC

  137 Millard St, Fairfield, CT 06824
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  /39

  $2,597,000

  • 5 Beds
  • 5 Baths
  • 4,549 Sq Ft

  26 Hitchcock Rd, Westport, CT 06880

  Welcome to Brookside, the sensational new construction by GreenDay and Co., making its grand debut in the enchanting town of Westport! Prepare to be dazzled by our very first home transformation-a stunning fusion of old-world charm and modern luxury that's sure to leave you in awe. This isn't just another modern farmhouse; it's a magnificent reimagining of a European-style residence, meticulously

  Mar Jennings Higgins Group Bedford Square

  26 Hitchcock Rd, Westport, CT 06880
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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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  /40

  $2,799,000

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

  342 Midlock Rd, Fairfield, CT 06824

  Welcome to Summer Tree Gardens, an extraordinary stately home nestled on over 2 acres of meticulously maintained grounds in the prestigious Greenfield Hill neighborhood of Fairfield, CT. This expansive 7,269 sq. ft. home boasts 5 en-suite bedrooms, 8.5 baths, and an array of luxurious features that blend timeless elegance with modern updates. The home was built by builder Christer Krook. Step

  Ken Osborn Higgins Group Bedford Square

  342 Midlock 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

  $2,599,000

  • 11 Beds
  • 10 Baths
  • 15,118 Sq Ft

  124 Old Battery Rd, Bridgeport, CT 06605

  A very special Fairfield County Connecticut Gold Coast mansion at St. Mary's-by-the-Sea and Long Island Sound. Experience The Chimneys, an architectural gem designed by Charles Wellington Walker in 1928. This Georgian Revival home won America's Finest Home Award in 2015. The 54-foot Grand Hall features a sweeping staircase with hand-wrought iron balustrades. Eleven artful fireplaces add warmth

  Gail Robinson William Raveis Real Estate

  124 Old Battery Rd, Bridgeport, CT 06605
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  /33

  $2,595,000

  • 7 Beds
  • 6 Baths
  • 7,843 Sq Ft

  125 Brett Ln, Fairfield, CT 06824

  Discover your private sanctuary at the end of a serene cul-de-sac in Greenfield Hill. This country compound spans 4.5 acres, enveloping a French-inspired main house with 6 BRs, 4.2 baths, and an enchanting English garden. Go into the elegant formal living and dining rooms, both warmed by inviting FPs, setting the stage for memorable moments. The custom gourmet kitchen, designed for living, opens

  Linna Yuen Coldwell Banker Realty

  125 Brett Ln, Fairfield, CT 06824
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  /39

  $1,999,000 Open Sun 12PM - 3PM

  • 6 Beds
  • 4.5 Baths
  • 4,344 Sq Ft

  15 Barton Rd, Fairfield, CT 06824

  Your storybook home-complete with a classic white picket fence-awaits! Where natural light fills inviting spaces, every detail is intentional, & comfort meets elegance. From quiet mornings on the sun-drenched porch to lively evenings around the large kitchen island, this home offers beauty, privacy, & seamless indoor-outdoor living. This newly finished, meticulously custom crafted, all new

  Jennifer DeLaurentis Compass Connecticut, LLC

  15 Barton Rd, Fairfield, CT 06824
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  /39

  $699,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,533 Sq Ft

  114 Castle Ave, Fairfield, CT 06825

  A beautifully fully remodeled Colonial awaits - welcome home to 114 Castle Avenue. Offering four spacious bedrooms two of which are on the first floor (a rare find) and two full bathrooms, one on the first level and one on the second blending modern updates with easy living. The stunning all new eat-in kitchen, featuring a large center island, sleek quartz countertops, brand new appliances and

  Lisa Mancini William Raveis Real Estate

  114 Castle Ave, Fairfield, CT 06825
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  /40

  $1,749,000 Open Sun 11:30AM - 2PM

  • 5 Beds
  • 4.5 Baths
  • 4,420 Sq Ft

  332 Szost Dr, Fairfield, CT 06824

  Stunning new construction in Fairfield's desirable University area! Re-Built from foundation up with taste, blends thoughtful design with quality craftsmanship. Privately set yet close to town, train, beaches, and top schools, the home features an ideal layout for modern living. Step into a welcoming foyer with open sightlines. Main level features a mudroom with built-ins and pet/boot wash, a

  Karim Douich William Raveis Real Estate

  332 Szost Dr, Fairfield, CT 06824
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  /34

  $1,299,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,449 Sq Ft

  6 Janson Dr, Westport, CT 06880

  Nestled on a quiet cul-de-sac just minutes from town, this well-maintained contemporary colonial offers the perfect blend of comfort, style and convenience. Set on a beautifully landscaped half-acre lot with mature plantings, this house has privacy while remaining close to shopping, restaurants, commuter routes and local amenities including town tennis courts and ball fields. Inside the open

  Tamarra Pincavage William Pitt Sotheby's Int'l

  6 Janson Dr, Westport, CT 06880
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  /25

  $995,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,995 Sq Ft

  18 Calumet Rd, Westport, CT 06880

  Located in a one of Westport's favorite neighborhood close to downtown Westport, schools, and commuter routes, this split-level gem offers both character and practicality.Discover the perfect blend of function and comfort in this split-level home. Featuring 3 bedrooms and 2 bathrooms across approximately 2,258 square feet, this versatile layout is ideal for families. Step inside to a bright

  Sophia Maragos Coldwell Banker Realty

  18 Calumet Rd, Westport, CT 06880
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  /14

  $399,999

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

  Unlisted Address

  Located in the heart of the highly sought-after Brooklawn neighborhood, this charming and spacious home offers the perfect blend of classic character and modern comfort. Enjoy a generous backyard, perfect for summer gatherings or peaceful mornings, and take advantage of proximity to schools, shopping, parks, and major highways. Whether you're commuting or working from home. Don't miss this

  Andrew Cevasco Las Americas Real Estate

  Unlisted Address
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  /40

  $1,595,000 Open Sat 1PM - 4PM

  • 2 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  69 River St, Southport, CT 06890

  Situated near the head of Southport Harbor and within walking distance to the village, train station, and all the charm of Southport life, this 1904 jewel-box home blends historic character with elevated, designer-informed updates. With two bedrooms, two full and one half baths, charming public rooms, a finished third floor (ideal to use for additional bedroom or home office), and an attached

  Wendy Ryan Brown Harris Stevens

  69 River St, Southport, CT 06890

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