Southport, CT Homes 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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  /23

  $199,900

  • 1 Bed
  • 1 Bath
  • 1,093 Sq Ft

  80 Cartright St Unit GC, Bridgeport, CT 06604

  Exceptional Condo Living at 80 Cartright Street, Bridgeport Where Historic Charm Meets Modern Convenience in the Brooklawn-St. Vincent Neighborhood Located in the sought-after Brooklawn-St. Vincent section of Bridgeport, 80 Cartright Street offers the perfect combination of comfort, convenience, and timeless appeal. Set within the well-maintained Cartright Towers condominium complex, this

  

  Alan Stewart Jr.

  ASJ Realty Partners

  (203) 871-0948

  80 Cartright St Unit GC, Bridgeport, CT 06604
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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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  /35

  $885,000

  • 5 Beds
  • 3 Baths
  • 2,600 Sq Ft

  4 Robert Ln, Westport, CT 06880

  Nestled on a secluded cul-de-sac just off Hogan Trail, this peaceful residence sits on a spacious 0.45-acre plot. Enjoy the convenience of walking distance access to the train station, downtown shopping, Saugatuck restaurants, and 5 min ride to the beach. The main level features a spacious living room, connected to the kitchen, dining area, and a deck, creating an ideal space for relaxation.

  Inna Agujen Coldwell Banker Realty

  4 Robert Ln, 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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  /38

  $1,125,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,764 Sq Ft

  992 S Pine Creek Rd Unit 992, Fairfield, CT 06824

  Perfection personified! This owner has spared no expense in upgrading this private unit, installing new Brazilian cherry floors, recessed lighting, wood window shutters, new high end appliances and painting the entire interior. The heating and AC systems are new. A sunken living room has a fireplace and a large deck accessed through sliders and has room for a dining table. The kitchen has all new

  Nancy Thorne Berkshire Hathaway NE Prop.

  992 S Pine Creek Rd Unit 992, 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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  /23

  $599,000

  • 2 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  48 Bywater Ln Unit 48, Bridgeport, CT 06605

  Rare opportunity to own an exquisite townhouse in the Historic Black Rock. Completely interior has been freshly painted. One of the most coveted condominium complexes Bywatyr Town Homes, a small complex o 24 units located on the cut-de-sac across from Fayerweather Yacht Club and Black Rock Harbor. This unit was the original model unit with many upgrades throughout. Year round water views from all

  Cristy Schnauffer Coldwell Banker Realty

  48 Bywater Ln Unit 48, Bridgeport, CT 06605
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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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  /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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  /36

  $620,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,362 Sq Ft

  6 Hills Ln Unit 6, Westport, CT 06880

  Beautifully renovated and impeccably decorated 3 bed, 2 bath condo located on the border of Westport and Norwalk in the desirable Birchwood complex. Set at the highest point in the community, this unit offers peaceful treetop views with a glimpse of the water in the distance, a rare and special setting! This spacious home lives entirely on one level and features gleaming hardwood floors, a cozy

  Erin Bremen melson The Agency

  6 Hills Ln Unit 6, Westport, CT 06880
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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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  /40

  $3,300,000

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

  750 Burr St, Fairfield, CT 06824

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

  Julie Vanderblue Higgins Group Real Estate

  750 Burr St, Fairfield, CT 06824
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  /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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  /31

  $2,249,000

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

  130 Easton Rd, Westport, CT 06880

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

  David Weber Compass Connecticut, LLC

  130 Easton Rd, Westport, CT 06880
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  /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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  /39

  $3,300,000 Open Thu 11AM - 2PM

  • 4 Beds
  • 5 Baths
  • 3,800 Sq Ft

  171 & 169 Compo Rd S, Westport, CT 06880

  REDUCED Below market value! Stunning new construction w/ 3900+SF tucked well away from the road offering a serene private setting nestled on a conforming .50 acre parcel with REMARKABLE and UNEQUALED potential. Offering fabulous convenience to Saugatuck train, Longshore town-golf club, Compo Beach and Downtown all via sidewalks. Combined and purchased together, 171 & 169 Compo Rd. S., can make

  Tanya Sprague William Raveis Real Estate

  171 & 169 Compo Rd S, Westport, CT 06880
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  /37

  $3,250,000

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

  450 Penfield Rd, Fairfield, CT 06824

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

  Julie Vanderblue Higgins Group Real Estate

  450 Penfield Rd, Fairfield, CT 06824
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  /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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  /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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  /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 Sun 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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