Southport, CT Homes for Sale

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  /40

  $2,650,000

  • 4 Beds
  • 5 Baths
  • 5,394 Sq Ft

  3007 Redding Rd, Fairfield, CT 06824

  A gorgeous Farmhouse Colonial tucked away on 2+ picturesque acres & minutes to Fairfield & Westport town await. Natural beauty, brilliant architecture, craftmanship & updates combine to make this home a standout. Featuring 12 rooms flooded w/ light over 3 levels of living. Enjoy views of a serene fallow field, a gentle stream, wildlife & stunning seasonal changes from vibrant autumn colors to

  

  Jackie Davis

  William Raveis Real Estate

  3007 Redding Rd, Fairfield, CT 06824
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  /39

  $2,800,000

  Open Sat 1PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,241 Sq Ft

  7 Short St, Westport, CT 06880

  Premier in-town location & exceptional craftsmanship come together in this stunning custom-built home by a respected local luxury builder. Just 2 years young, this exquisite home is ideally situated at the end of a quiet cul-de-sac, offering privacy & convenience while only 4 minutes from town - Welcome home to 7 Short Street. Presenting 3 levels of beautifully finished living space, this

  

  Jackie Davis

  William Raveis Real Estate

  7 Short St, Westport, CT 06880
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  /40

  $1,995,000

  Open Sun 1PM - 3PM

  • 5 Beds
  • 3.5 Baths
  • 6,310 Sq Ft

  71 High Point Rd, Westport, CT 06880

  Tucked at the end of one of Westport's most coveted cul-de-sacs, this 5-bedroom contemporary offers 6,310 sq ft of finished living space on just over a private acre, with a backyard path leading directly to Bedford Middle and Staples High School. From the foyer, a dramatic vaulted living room with skylights, built-ins and a floor-to-ceiling stone fireplace sets the tone. The glass-wrapped sunroom

  

  Hyleri Katzenberg

  Compass Connecticut, LLC

  71 High Point Rd, Westport, CT 06880
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  /37

  $565,000

  $34K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 1,155 Sq Ft

  50 Stone Ridge Way Unit 2A, Fairfield, CT 06824

  Luxury living in a gated community across from the Fairfield-Blackrock Train Station, close to the Whole Foods Shopping Center and restaurants. This sophisticated 1 Bedroom 1.5 Bathroom unit includes a sunny deck overlooking the community. Extraordinary appointments and impeccable design elements such as 9'+ ceilings throughout, hardwood floors, and a gourmet kitchen with stainless steel Viking

  

  Maria Graham-Baptist

  Coldwell Banker Realty

  50 Stone Ridge Way Unit 2A, Fairfield, CT 06824
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  /40

  $1,574,999

  $25K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,443 Sq Ft

  313 Old Post Rd, Fairfield, CT 06824

  Welcome to 313 Old Post Road, a timeless Fairfield residence blending classic charm with an unbeatable location in one of the town's most desirable coastal neighborhoods. This beautifully maintained home offers inviting living spaces, abundant natural light, and the perfect balance of comfort and convenience. Recent improvements include updated AC units in 2023, new wiring in the detached heated

  

  Joel Grispino

  Drawbridge Realty

  313 Old Post Rd, Fairfield, CT 06824
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  /40

  $1,799,900

  $75K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,032 Sq Ft

  82 Lee Dr, Fairfield, CT 06824

  Ideally located in the highly sought-after Sasco Hill neighborhood, this exceptional coastal home offers the rare advantage of beach-area living outside the flood zone-no flood insurance required. Perfectly positioned between town and shoreline, the property features a stunning second-floor addition completed in 2025 with over $200,000 invested, including a rooftop deck with beautiful Long Island

  

  Jacek Mikolajczyk

  Berkshire Hathaway NE Prop.

  82 Lee Dr, Fairfield, CT 06824
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  /40

  $3,650,000

  • 6 Beds
  • 6.5 Baths
  • 6,751 Sq Ft

  9 N Ridge Rd, Westport, CT 06880

  In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined

  

  Susan Lieberman

  The Riverside Realty Group

  9 N Ridge Rd, Westport, CT 06880
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  /21

  $949,000

  • 3 Beds
  • 1.5 Baths
  • 1,684 Sq Ft

  54 Elm St, Fairfield, CT 06824

  Rare opportunity to live on one of the most coveted streets in the (Fairfield )University area, and on one of the largest parcels. A short stroll to train , beach and downtown / Post Rd. Nestled off road with beautiful curb appeal including stone and wood exterior , mature growth trees surround property , along with a vintage barn - like garage at street level predating home , affording 2

  

  Thomas Bepko

  YellowBrick Real Estate LLC

  54 Elm St, Fairfield, CT 06824
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  /19

  $1,699,000

  • 3 Beds
  • 1 Bath
  • 1,450 Sq Ft

  173 Puritan Rd, Fairfield, CT 06824

  Located in the highly desirable beach area of Fairfield, this charming and beautifully maintained 3-bedroom Cape, situated on a corner lot, offers the perfect blend of classic character and modern convenience. The newly remodeled eat-in kitchen features granite countertops and stylish finishes throughout. Enjoy entertaining in the formal dining room with beautiful built-in hutches or relax in the

  

  Glenn Marr

  Marr Caruso Realty Group

  173 Puritan Rd, Fairfield, CT 06824
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  /3

  $450,000

  • Land
  • 6,969 Sq Ft
  • $2,812,500 per Acre

  37 Bartram Ave, Bridgeport, CT 06605

  St Mary's by the Sea flat and cleared building lot. Single family and multifamily possible at this location. Beautiful tree lined street close to the water.

  

  David Krasnoff

  Compass Connecticut, LLC

  37 Bartram Ave, Bridgeport, CT 06605
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  /40

  $755,000

  Open Sun 1PM - 3PM $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,524 Sq Ft

  241 Old Stratfield Rd, Fairfield, CT 06825

  Completely renovated and thoughtfully updated from top to bottom, this beautifully renovated home offers a rare opportunity to own a turnkey two-family home in Fairfield with stylish modern finishes and carefree ownership for years to come. Ideal for owner-occupants, investors, or multi-generational living, the property features a beautifully updated 1 bedroom, 1 bath apartment on the first floor

  

  Andrei Balaj

  Higgins Group Real Estate

  241 Old Stratfield Rd, Fairfield, CT 06825
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  /36

  $2,395,000

  Open Sat 12AM - 2PM $100K PRICE DROP

  • 6 Beds
  • 5.5 Baths
  • 3,700 Sq Ft

  40 Richmondville Ave, Westport, CT 06880

  Built in 2022, 40 Richmondville Avenue offers generous scale, a thoughtful layout, and true move-in-ready ease. Bright, open-concept main level connects kitchen, dining, and living spaces, with high ceilings and oversized windows throughout. The kitchen features a full Thermador appliance suite, large island with integrated outlets, extensive cabinetry, walk-in pantry, and mudroom with built-ins.

  Jessica Lane

  Serhant Connecticut, LLC

  40 Richmondville Ave, Westport, CT 06880
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  /34

  $950,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 2,100 Sq Ft

  102 Geneva Terrace, Fairfield, CT 06824

  Rare opportunity in Fairfield's highly sought-after Beach Area! This 3-bedroom, 1,400 SF ranch offers an exceptionally rare combination of location, lot, and future potential. Just a short walk to South Pine Creek Beach and only a quarter mile from the prestigious Sasco Hill neighborhood, you'll also enjoy easy access to downtown Fairfield, the train station, restaurants, shops, and beaches.

  

  Judy Szablak

  Coldwell Banker Realty

  102 Geneva Terrace, Fairfield, CT 06824
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  /7

  $995,000

  New Construction

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

  53 Sterling St, Fairfield, CT 06825

  New construction townhome built by a respected local builder known for quality craftsmanship and clean, modern design. This residence offers approximately 2,300 square feet of above-grade living plus a finished lower level, thoughtfully laid out across three levels. The main floor features an open-concept design anchored by a well-appointed kitchen with white and white oak cabinetry, quartz

  Jessica Lane

  Serhant Connecticut, LLC

  53 Sterling St, Fairfield, CT 06825
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  /7

  $995,000

  New Construction

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

  45 Sterling St, Fairfield, CT 06825

  New construction townhome built by a respected local builder known for quality craftsmanship and clean, modern design. This residence offers approximately 2,300 square feet of above-grade living plus a finished lower level, thoughtfully laid out across three levels. The main floor features an open-concept design anchored by a well-appointed kitchen with white and white oak cabinetry, quartz

  Jessica Lane

  Serhant Connecticut, LLC

  45 Sterling St, Fairfield, CT 06825
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  /7

  $995,000

  New Construction

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

  51 Sterling St, Fairfield, CT 06825

  New construction townhome built by a respected local builder known for quality craftsmanship and clean, modern design. This residence offers approximately 2,300 square feet of above-grade living plus a finished lower level, thoughtfully laid out across three levels. The main floor features an open-concept design anchored by a well-appointed kitchen with white and white oak cabinetry, quartz

  Jessica Lane

  Serhant Connecticut, LLC

  51 Sterling St, Fairfield, CT 06825
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  /7

  $995,000

  New Construction

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

  47 Sterling St, Fairfield, CT 06825

  New construction townhome built by a respected local builder known for quality craftsmanship and clean, modern design. This residence offers approximately 2,300 square feet of above-grade living plus a finished lower level, thoughtfully laid out across three levels. The main floor features an open-concept design anchored by a well-appointed kitchen with white and white oak cabinetry, quartz

  Jessica Lane

  Serhant Connecticut, LLC

  47 Sterling St, Fairfield, CT 06825
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  /19

  $4,250,000

  New Construction

  • 6 Beds
  • 9 Baths
  • 7,499 Sq Ft

  6 Janson Dr, Westport, CT 06880

  Exceptional new construction by AR Luxury Homes with 7,500+/- square feet of thoughtfully designed living space across four finished levels in a prime Westport location. This 6-bedroom, 6 full and 3 half bath residence blends refined craftsmanship with modern functionality, featuring an open-concept layout ideal for both everyday living and entertaining. The heart of the home is a custom-designed

  

  Brett Lieberman

  The Riverside Realty Group

  6 Janson Dr, Westport, CT 06880
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  /15

  $7,926,000

  New Construction

  • 6 Beds
  • 7 Baths
  • 7,200 Sq Ft

  0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880

  Set within Westport's most prestigious private estate enclave, surrounded by grand coastal estates and quintessential antique treasures, this exceptional Greens Farms 2+ acre* new construction offering is poised to become one of Fairfield County's most coveted addresses. Perfectly positioned, moments from beaches, downtown boutiques, vibrant dining scene, and just an express train to Manhattan,

  

  Brett Lieberman

  The Riverside Realty Group

  0 Clapboard Hill Rd Unit (New Build), Westport, CT 06880
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  /39

  $1,599,000

  Open Sun 11AM - 1:30PM

  • 4 Beds
  • 4 Baths
  • 3,290 Sq Ft

  694 Jennings Rd, Fairfield, CT 06824

  Exceptional opportunity to own what is essentially a brand-new home in Fairfield University area. Expanded with a full second-story addition and reconstructed from the original foundation up, this remarkable residence offers 3,290 square feet of beautifully finished living space with virtually every major component newly built. Designed for today's lifestyle, the open-concept floor plan features

  Karim Douich William Raveis Real Estate

  694 Jennings Rd, Fairfield, CT 06824
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  /25

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  119 Kings Hwy N, Westport, CT 06880

  House and land are fully available. Build your dream house on this beautiful lot in the Old Hill section of Westport. The small single-family home was converted into two apartments in the 1930s by its then-owners. The land is in a Residential AA zone and any construction needs to follow all the towns regulations. Walk to town from this generous .87 acre lot that has views of the town and river in

  Helen Cusa Brown Harris Stevens

  119 Kings Hwy N, Westport, CT 06880
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  /20

  $550,000

  • 8 Beds
  • 3 Baths
  • 2,679 Sq Ft

  18-20 Clinton Ave, Bridgeport, CT 06605

  This very large 2,679 sqft 2 family property is perfect for any home owner or investor. The 1st floor unit consists of 3 bedrooms and 1 bathroom. The 2nd unit is a very spacious two floor apartment that has 5 bedrooms and 2 bathrooms that was recently updated. Conveniently located just minutes from I-95 and I-91. Schedule your showing today!!!

  Thomas Payne Century 21 Scala Group

  18-20 Clinton Ave, Bridgeport, CT 06605
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  /19

  $319,900

  $26K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,145 Sq Ft

  3250 Fairfield Ave Unit 206, Bridgeport, CT 06605

  Welcome to The Village at Black Rock. This bright 2BR/2BA second-floor unit offers serene water views from nearly every room and a private deck ideal for morning coffee or sunset unwinding. The open layout features a combined living/dining area with a wall of windows overlooking Ash Creek and a spacious kitchen with ample storage, great counter space, and a breakfast bar. The primary bedroom

  Patrick Laufer Laufer Real Estate

  3250 Fairfield Ave Unit 206, Bridgeport, CT 06605
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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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  /40

  $11,995,000

  New Construction Open Sun 1PM - 3PM

  • 5 Beds
  • 7 Baths
  • 6,050 Sq Ft

  14 Owenoke Park, Westport, CT 06880

  Summer starts here. Set on prestigious Owenoke Park steps from Compo Beach, this brand-new 6,050 sqft coastal masterpiece delivers the ultimate Westport lifestyle - pool and spa, Gray's Creek waterfront access, Long Island Sound views throughout, and a rare 3-car garage. Five ensuite bedrooms, double-island kitchen with scullery, elevator, primary suite sauna, and a lower-level loggia built for

  Deirdre Andreoli Compass Connecticut, LLC

  14 Owenoke Park, Westport, CT 06880
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  /40

  $2,650,000

  Open Sun 12PM - 2PM

  • 5 Beds
  • 5.5 Baths
  • 7,055 Sq Ft

  53 Clinton Ave, Westport, CT 06880

  Incredibly located moments from town and convenient to schools, shopping, commuting options and more, this sparkling home showcases pride of ownership. A new 2026 driveway leads to the landscaped setting, where this gracious home with an in-ground Wagner pool is set amid .74+/- acre. The two-story foyer introduces crisp, timeless spaces, and a home that has been impeccably maintained. The living

  Alex Chingas Coldwell Banker Realty

  53 Clinton Ave, Westport, CT 06880
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  /32

  $2,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,381 Sq Ft

  125 Battery Park Dr, Bridgeport, CT 06605

  Perched on a quiet cul-de-sac, this exceptional home offers breathtaking 220-degree panoramic views of Long Island Sound, Black Rock Harbor, and Fayerweather lighthouse. Designed for effortless main-level living, the residence captures stunning water views from the living room, dining room, and luxurious primary bedroom suite. The remodeled primary bath features elegant marble flooring with

  Gail Robinson William Raveis Real Estate

  125 Battery Park Dr, Bridgeport, CT 06605
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  /2

  $699,000

  • Land
  • 16,117 Sq Ft
  • $1,889,189 per Acre

  1 Battery Park Dr, Bridgeport, CT 06605

  Welcome to an exceptional opportunity in the highly sought after enclave at Black Rock! Nestled on a .37 acre lot this parcel boasts unparrelled vistas of the majestic Long Island Sound a canvas for your visionary masterpiece. This prime location beckons investors and builders alike to sieze the potential of coastal living at its finest. Edmbrace the allur of seaside living and capitalize on this

  Steven Koleno Beycome of Connecticut

  1 Battery Park Dr, Bridgeport, CT 06605
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  /20

  $642,000

  Open Sat 12PM - 2PM $5K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,310 Sq Ft

  781 Tunxis Hill Rd, Fairfield, CT 06825

  Welcome Home, Charming 4-bedroom, 2-full-bath cape offering the perfect blend of suburban comfort and town convenience in the Tunxis Hill area of Fairfield. This residence sits on a manageable level lot, making it an incredible opportunity for first-time buyers, downsizers, or anyone looking to establish roots in one of Fairfield County's most sought-after communities. Step inside to a bright

  Amy Vaupel William Pitt Sotheby's Int'l

  781 Tunxis Hill Rd, Fairfield, CT 06825
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  /40

  $6,795,000

  • 7 Beds
  • 6.5 Baths
  • 9,209 Sq Ft

  21 Compo Pkwy, Westport, CT 06880

  A rare offering in Westport's coveted Compo Beach neighborhood, this extraordinary estate sits on a prized double lot just moments from Compo Beach, Longshore Club, train & vibrant downtown. Featured in Westport Magazine, the property masterfully blends the charm of a beautifully preserved historic residence from 1928 w/ a remarkable 6,000 sq ft addition completed in 2008. The result is a

  Sarah Fair William Raveis Real Estate

  21 Compo Pkwy, Westport, CT 06880
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  /5

  $769,000

  • Land
  • 2.07 Acres
  • $371,498 per Acre

  180 Catamount Rd, Fairfield, CT 06824

  Approvals in place for this 2+ acre shovel ready lot in prestigious Greenfield Hill. 193 feet of frontage plus city water available in the street. This is an excellent opportunity to build your dream home on a beautiful cleared and leveled lot. All necessary inland wetland, conservation and septic/health department permits have been established. Located minutes to the Patterson Club and less then

  Mona Cascella William Raveis Real Estate

  180 Catamount Rd, Fairfield, CT 06824
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  /40

  $5,549,000

  • 4 Beds
  • 5 Baths
  • 7,105 Sq Ft

  80 Compo Rd N, Westport, CT 06880

  Timeless design meets modern sustainability in this stunning shingle-style home, set on 1.5 private in-town acres. Sunlight fills every room through oversized Kolbe windows, showcasing park-like grounds and mature plantings. The kitchen impresses with custom cabinetry, a handcrafted zinc island, and top-tier Wolf and Sub-Zero appliances. Step outside to a spectacular bluestone patio with an

  Adrienne Durkin Compass Connecticut, LLC

  80 Compo Rd N, Westport, CT 06880
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  /39

  $2,799,000

  $151K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 2,188 Sq Ft

  1235 Fairfield Beach Rd, Fairfield, CT 06824

  TWO incredible waterside opportunities await! That's right, not one, but TWO fantastic beach area homes are offered! With their direct waterfront locations (1235 - beachfront/LI Sound; 1236 - canal side), both homes have amazing water views, beach access and a convenient, fantastic location all in one! Both homes also offer excellent investment/rental opportunities. #1235 is rented for the

  John Foran Compass Connecticut, LLC

  1235 Fairfield Beach Rd, Fairfield, CT 06824
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  /34

  $5,499,000

  • 6 Beds
  • 8 Baths
  • 7,748 Sq Ft

  359 Greens Farms Rd, Westport, CT 06880

  Tucked behind elegant wrought-iron gates at the end of a long private driveway, this exceptional Greens Farms estate offers the perfect blend of privacy, luxury, and convenience in one of Westport's most coveted neighborhoods. Surrounded by mature landscaping, this meticulously maintained residence feels like a private retreat while remaining steps from the Greens Farms train station, Burying

  Judy Michaelis Coldwell Banker Realty

  359 Greens Farms Rd, Westport, CT 06880
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  /40

  $12,000,000

  • 7 Beds
  • 10 Baths
  • 9,129 Sq Ft

  4800 Congress St, Fairfield, CT 06824

  This offering is for 4800 Congress St, a one of a kind estate consists of main residence on 10.92 acres, pool, barn pool house/gym, heated paddle court, and an office pavilion. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street,offering seclusion with proximity to NYC. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century

  Leslie Razook William Pitt Sotheby's Int'l

  4800 Congress St, Fairfield, CT 06824
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  /19

  $10,500,000

  • 4 Beds
  • 5.5 Baths
  • 10,522 Sq Ft

  47 Charcoal Hill Rd, Westport, CT 06880

  Designed by renowned architect and builder Frazier Forman Peters, this stone estate is set on nearly 3.5 private, meticulously landscaped acres in Westport. Crafted over more than two decades, the residence reflects exceptional artistry, scale, and craftsmanship. A gated entry and winding stone drive arrive at a stately porte-cochere and attached two-car garage, establishing a grand sense of

  Jonathan Ducharme Serhant Connecticut, LLC

  47 Charcoal Hill Rd, Westport, CT 06880
• 

  

  /27

  $939,000

  $36K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,361 Sq Ft

  43 Green Knolls Ln, Fairfield, CT 06824

  Welcome home to this beautifully maintained 3-bedroom Cape, ideally situated on a quiet cul-de-sac. Filled with natural light and surrounded by mature plantings and professionally landscaped grounds, this home offers the perfect blend of comfort, convenience, and lifestyle. Just minutes from the Merritt Parkway, I-95, Metro North, vibrant downtown Fairfield, exceptional restaurants, shopping, and

  Carol Frattaroli William Pitt Sotheby's Int'l

  43 Green Knolls Ln, Fairfield, CT 06824
• 

  

  /36

  $6,499,000

  • 5 Beds
  • 7 Baths
  • 6,189 Sq Ft

  775 Sasco Hill Rd, Fairfield, CT 06824

  775 Sasco Hill Road is an extraordinary estate where timeless elegance meets modern luxury. Impeccably renovated and beautifully curated by the current owners, this sophisticated residence offers three full levels of refined living set across five private, park-like acres. A dramatic cathedral foyer and soaring 9-foot ceilings create an immediate sense of scale and light, while the thoughtfully

  Suzy Ryan William Raveis Real Estate

  775 Sasco Hill Rd, Fairfield, CT 06824
• 

  

  /22

  $625,000

  Open Sat 1PM - 4PM

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  439 Stillson Rd, Fairfield, CT 06824

  Ideally situated in a highly convenient location, this home offers easy access to shopping, dining, schools, parks, transportation and everyday essentials within easy reach. Enjoy the ideal balance of comfort and accessibility, with everything you need just moments from your front door. This home has an open floor plan that connects the kitchen to the dining area with an easy entrance from the

  Rima Bishuti William Raveis Real Estate

  439 Stillson Rd, Fairfield, CT 06824
• 

  

  /40

  $2,749,000

  Open Sat 11AM - 1PM

  • 5 Beds
  • 7 Baths
  • 7,317 Sq Ft

  3080 Sturges Hwy, Westport, CT 06880

  Welcome to 3080 Sturges - Fully Renovated Home set on 2.44 private acres in Fairfield's Greenfield Hill enclave on the Westport border. Offering a Westport mailing address together with Fairfield's acclaimed schools and amenities, this 7,317-square-foot modern residence blends architectural scale with contemporary comfort and luxury. A dramatic two-story foyer introduces interiors defined by

  Ryan Sullivan Berkshire Hathaway NE Prop.

  3080 Sturges Hwy, Westport, CT 06880

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