Southport, CT Houses for Sale

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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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  /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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  /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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  /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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  /39

  $3,250,000

  • 4 Beds
  • 4.5 Baths
  • 5,092 Sq Ft

  36 Bonnie Brook Rd, Westport, CT 06880

  Welcome to your dream home in one of Westport's most desirable and charming neighborhoods. This beautifully crafted residence includes a sparkling pool and is perfectly nestled in a peaceful, walkable community-for bike rides and evening strolls. This home seamlessly blends modern design with a fresh take on the timeless Modern Farmhouse, offering both style and function. A spacious front porch

  Michael Ferraro Compass Connecticut, LLC

  36 Bonnie Brook 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

  $3,375,000

  • 5 Beds
  • 6 Baths
  • 4,668 Sq Ft

  91 Turkey Hill Rd S, Westport, CT 06880

  Welcome to a home that lives as beautifully as it looks. In the heart of Greens Farms, this timeless 5 bedroom, 6 bath Colonial is where classic elegance meets modern ease, designed for how you live, work, and entertain today. A circular drive, stone walls, and a charming front porch create an inviting first impression. Inside, a sun-filled double-height entry sets the tone for open, gracious

  Chrissie Rodriguez Higgins Group Real Estate

  91 Turkey Hill Rd S, Westport, CT 06880
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  /40

  $2,399,000

  • 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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  /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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  /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

  $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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  /39

  $2,545,000

  • 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

  $2,299,000

  • 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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  /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

  • 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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  /3

  $2,199,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,700 Sq Ft

  180 Catamount Rd, Fairfield, CT 06824

  New Construction of a shingle style colonial in the prestigious Greenfield Hill section of Fairfield. Approvals in place for this home on a designated scenic road. 193 feet of frontage plus city water available in the street. This is an excellent opportunity to customize your dream home on a beautiful, cleared and leveled Greenfield Hill lot surrounded by nature, charming New England stone walls

  Mona Cascella William Raveis Real Estate

  180 Catamount Rd, Fairfield, CT 06824
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  /40

  $2,900,000 New Construction

  • 6 Beds
  • 6.5 Baths
  • 6,351 Sq Ft

  158 Compo Rd N, Westport, CT 06880

  Come see the latest CCO Habitats new construction home - located at the end of a private road - 1 Hubbel's Lane - and buffered by non developable land for privacy. Only one mile to downtown/Main Street (.6 mile to Coffee An' for the best donuts in town!!) with sidewalks to make the stroll even easier! Walk the other way, and you're 1.5 miles from the newly renovated Coleytown school district.

  Maryann Levanti Higgins Group Bedford Square

  158 Compo Rd N, Westport, CT 06880
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  /4

  $2,295,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,514 Sq Ft

  96 Clinton St, Fairfield, CT 06824

  Enjoy the beach life year round at this perfect walk everywhere location .. just steps to Jennings Beach, Sand Castle Park and the Fairfield Marina. Located on a quiet cul-de-sac with privacy. Don't miss this opportunity to customize your gorgeous New home which will be underway soon and should be complete by the end of the year. Meet with the builders and choose your finishes! 4 bedrooms, 3.5

  Bette Gigliotti William Raveis Real Estate

  96 Clinton St, Fairfield, CT 06824
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  /40

  $1,050,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,552 Sq Ft

  98 Cambridge St, Fairfield, CT 06824

  Picture Perfect Expanded Cape on quiet side street in Fairfield's Beach & Marina Neighborhood! Enjoy life and living with access to coveted beach with boating, bonfires, and clambakes or walk to train and downtown with award winning restaurants and shopping! Many new upgrades and expansion to make this home all ready to move in! Gorgeous Kitchen with huge Island with seating. New Trex Deck via

  Terry Keegan Fairfield County Real Estate

  98 Cambridge St, Fairfield, CT 06824
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  /28

  $800,000

  • 4 Beds
  • 2.5 Baths
  • 2,860 Sq Ft

  38 Pepperbush Ln, Fairfield, CT 06824

  Wonderful University center hall colonial conveniently located to everything. This well cared for home includes a formal living room and dining room, updated eat-in-kitchen with granite counters and st / st appliances and a bright and spacious family room with a terrific fireplace. The second floor includes a primary bedroom with a bath and walk-in closet, a hall bath and 3 additional bedrooms.

  John Shea William Raveis Real Estate

  38 Pepperbush Ln, Fairfield, CT 06824
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  /17

  $649,900

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  142 Doreen Dr, Fairfield, CT 06824

  Charming 3-bedroom, 1-bath Ranch nestled on a private lot surrounded by mature privacy hedges in a phenomenal Fairfield neighborhood. Hardwood floors lie beneath all carpeting (excluding kitchen and porch), offering excellent potential for easy updates. The spacious 3-season porch provides opportunity for year-round use with a simple conversion. The finished lower level adds 480 sq ft of living

  Frank D'Ostilio Houlihan Lawrence WD

  142 Doreen Dr, Fairfield, CT 06824
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  /39

  $1,999,000

  • 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

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

  114 Castle Ave, Fairfield, CT 06825

  A beautiful, COMPLETELY REMODELED in 2025 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

  Lisa Mancini William Raveis Real Estate

  114 Castle Ave, Fairfield, CT 06825
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  /40

  $1,749,000

  • 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

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

  6 Janson Dr, Westport, CT 06880

  PRESENT OFFERS BY NOON MONDAY, 8/4. 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

  Tamarra Pincavage William Pitt Sotheby's Int'l

  6 Janson Dr, Westport, CT 06880
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  /25

  $995,000

  • 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

  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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