20

Southport, CT Open Houses

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  • /34

    $3,550,000 Open Sat 1PM - 3PM

    • 5 Beds
    • 4.5 Baths
    • 4,602 Sq Ft

    10 Winding Ln, Westport, CT 06880

    Experience the pinnacle of luxury living in this exceptional 4,600 sq ft, 5-bedroom home, ideally located in highly sought-after Old Hill. Perfectly positioned on a pristine 1-acre lot, this stunning home offers a rare "walk-to-everything" lifestyle-just steps from shopping, top-rated restaurants, and Earthplace. Designed for both elegant entertaining and everyday comfort, the home features an

    Agent Photo

    Susan Lieberman

    The Riverside Realty Group

    (475) 255-2758

    10 Winding Ln, Westport, CT 06880
  • /2

    $869,900 Open Sat 12PM - 2PM

    • 9 Beds
    • 3 Baths
    • 2,922 Sq Ft

    219 Orland St Unit 221, Bridgeport, CT 06605

    Exceptional opportunity to own a well-maintained 3-family home in the highly sought-after Black Rock section of Bridgeport. Situated on a rare double lot, this property offers abundant outdoor space along with ample off-street parking-an uncommon and valuable feature in the area. Roof, siding, windows and all 3 high efficiency Navien boilers were replaced 2 years ago. All apartments were recently

    Agent Photo

    Jorge Cintron

    Vylla Home (CT) LLC

    (475) 473-8158

    219 Orland St Unit 221, Bridgeport, CT 06605
  • /40

    $2,850,000 Open Sat 1PM - 3PM

    • 5 Beds
    • 5 Baths
    • 4,922 Sq Ft

    55 Center St, Westport, CT 06880

    Located in Westport's coveted Greens Farms neighborhood, this light-filled home is perfectly sited high and dry on a private park-like acre with room for a pool and pool house. A renovated kitchen with top-of-the-line appliances and sunny breakfast nook opens to a spacious great room with stone fireplace and expansive deck overlooking the property, ideal for indoor-outdoor living. The flexible

    Mary Ann Lindwall The Riverside Realty Group

    55 Center St, Westport, CT 06880
  • /32

    $1,329,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 2,029 Sq Ft

    310 Main St, Westport, CT 06880

    Spacious sophistication in the heart of Downtown Westport. Perfectly positioned just moments from vibrant shopping, dining and recreation, this lovely in-town residence offers a rare blend of comfort, flexibility, and location. Bathed in natural light, the inviting living room with wood-burning fireplace sets the tone for relaxed gatherings and quiet evenings alike. The open-concept kitchen

    Barbara Bross Coldwell Banker Realty

    310 Main St, Westport, CT 06880
  • /40

    $899,000 Open Sun 12:30PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,614 Sq Ft

    81 Old Stratfield Rd, Fairfield, CT 06825

    Located in the heart of Tunxis Hill-one of Fairfield's most convenient neighborhoods-this beautifully maintained Colonial blends classic design with modern living. Featuring 3 bedrooms and 2.1 bathrooms, the home has been freshly painted throughout and is truly move-in ready. Just minutes from shopping, dining, and everyday essentials, 81 Old Stratfield Road offers the perfect balance of comfort

    Young Lee Houlihan Lawrence WD

    81 Old Stratfield Rd, Fairfield, CT 06825
  • /25

    $745,000 Open Sun 3PM - 4PM

    • 4 Beds
    • 3 Baths
    • 1,984 Sq Ft

    329 Bronson Rd, Southport, CT 06890

    Location, location and location! Here is a chance to build some sweet equity that you have been waiting for! With 4 Bedrooms and 3 full bathrooms there is room for all. Living room with a fireplace along with two additional sitting room to accommodate all your guests. Partially fenced in yard, detached garage. Central air, gas heat, tankless hot water heater , 2 car detached garage, drive way

    Masooma Ali Connecticut Choice Realty

    329 Bronson Rd, Southport, CT 06890
  • /30

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

    • 4 Beds
    • 2.5 Baths
    • 3,728 Sq Ft

    757 Galloping Hill Rd, Fairfield, CT 06824

    This is not just a house-it's a home with soul. Lovingly cared for and impeccably maintained by the same family for nearly 30 years, this 4-bedroom, 3.5-bath Colonial unfolds in ways you don't expect, each space more surprising than the last. The kitchen is extraordinary-a centerpiece that captivates and performs. Anchored by a single-slab Carrera marble island and a premium Thermador suite, it

    Colleen Gennari William Raveis Real Estate

    757 Galloping Hill Rd, Fairfield, CT 06824
  • /40

    $1,295,000 Open Sat 12PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 2,959 Sq Ft

    185 Windsor Rd, Fairfield, CT 06824

    Tucked away on a quiet cul-de-sac in the desirable University area of Fairfield, this move-in-ready Colonial combines thoughtful updates, flexible living space, and an impressive, detached studio. Offering nearly 3,000 square feet of finished living space across three levels, this 4-bedroom, 3.5-bath home features a remodeled eat-in kitchen with new appliances, quartz countertops, farmhouse sink,

    Carrie Sakey Coldwell Banker Realty

    185 Windsor Rd, Fairfield, CT 06824
  • /38

    $1,599,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 3.5 Baths
    • 3,012 Sq Ft

    71 Aberdeen Way Unit 71, Southport, CT 06890

    Perfectly situated in Southport, this beautifully appointed 3-bedroom, 3.5-bath Colonial townhouse end unit offers an exceptional lifestyle just moments from village shops, restaurants, Southport Harbor, and the Metro-North train. Thoughtfully updated, the remodeled kitchen features quartz countertops, a sleek backsplash, and premium Bosch appliances, centered around a generous island-opening

    Michael Ferraro Compass Connecticut, LLC

    71 Aberdeen Way Unit 71, Southport, CT 06890
  • /28

    $999,900 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 3,515 Sq Ft

    22 Knollwood Dr, Fairfield, CT 06824

    Warm and inviting Colonial located in the highly sought-after University neighborhood of Fairfield. This 4-bedroom, 3.5-bath home offers exceptional flexibility with a fully finished walk-out basement featuring a full bathroom and separate entrance, ideal for multigenerational living or a potential in-law setup. From the moment you arrive, the home's beautiful exterior, attractive color palette,

    Melanie LeRoy William Raveis Real Estate

    22 Knollwood Dr, Fairfield, CT 06824
  • /38

    $2,095,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 5 Baths
    • 3,921 Sq Ft

    2177 Cross Hwy, Fairfield, CT 06824

    A special property with pool & tennis court, on the Westport border, minutes to shops, restaurants and train. Experience refined luxury in this picturesque setting, situated back from the road down a long, lighted driveway, winding past a serene pond. Nearly 4000 sq ft with 4 bedrooms & 4.5 baths, this open floor plan home features city water, sewer, natural gas, oil heat and central A/C for

    Mary Ellen Gallagher Compass Connecticut, LLC

    2177 Cross Hwy, Fairfield, CT 06824
  • /40

    $3,950,000 Open Sat 2PM - 4PM

    • 5 Beds
    • 9 Baths
    • 7,040 Sq Ft

    44 Pumpkin Hill Rd, Westport, CT 06880

    Set in one of Westport's most sought-after central neighborhoods, this gracious 5+ bedroom custom Colonial with a stunning gunite pool and spa offers the perfect balance of timeless elegance and modern comfort. Sun-filled interiors and thoughtful design create seamless flow for both entertaining and everyday living. The main level features a private office, elegant dining room with butler's

    Christine Oleynick Keller Williams Realty

    44 Pumpkin Hill Rd, Westport, CT 06880
  • /22

    $600,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    49 Southport Woods Dr, Southport, CT 06890

    Enjoy Southport Woods - community lifestyle with pool, clubhouse, paddle tennis and beautifully landscaped grounds in the heart of Southport. Convenient to Fairfield and Southport train stations, I-95, shopping, restaurants, schools and miles of beautiful shoreline, this location offers much. Privately located end unit features slate patio/yard area, two bedrooms (primary with full bath),

    Andrea Morelli Higgins Group Real Estate

    49 Southport Woods Dr, Southport, CT 06890
  • /38

    $950,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,205 Sq Ft

    198 Castle Ave, Fairfield, CT 06825

    Refined and thoughtfully updated 4-bedroom, 2.5-bath Colonial blending timeless architecture with over 1,300+ sq ft of new construction. Originally built in 1941 and significantly expanded, the home offers approximately 2,205 sq ft of living space upon completion (anticipated January 2026). The main level features a bright, open layout with remodeled living and dining areas and hardwood flooring

    Tatiana Mendoza Coldwell Banker Realty

    198 Castle Ave, Fairfield, CT 06825
  • /29

    $2,200,000 Open Sat 2PM - 4PM

    • 5 Beds
    • 4.5 Baths
    • 6,330 Sq Ft

    25 Old Rd, Westport, CT 06880

    Set in Westport's sought-after Hunt Club neighborhood, this European-inspired Colonial offers over 6,300 square feet across three finished levels, including expansive recreation spaces and a dedicated home theater. A dramatic two-story entry introduces refined formal and informal rooms, including a fireplaced living room, formal dining room, private office, and an expansive eat-in kitchen with

    Zach Wright William Pitt Sotheby's Int'l

    25 Old Rd, Westport, CT 06880
  • /40

    $7,500,000 Open Sun 1PM - 3PM

    • 6 Beds
    • 9 Baths
    • 9,576 Sq Ft

    8 Loretta Ct, Westport, CT 06880

    Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning three and a half levels, this six-bedroom home features an airy layout with refined finishes

    Lianne Owen Coldwell Banker Realty

    8 Loretta Ct, Westport, CT 06880
  • /39

    $1,775,000 Open Sat 1PM - 3PM

    • 5 Beds
    • 6 Baths
    • 4,150 Sq Ft

    706 Judd St, Fairfield, CT 06824

    Stunning move-in-ready NEW construction home in Fairfield's highly desirable University area, thoughtfully built by established local builders Coppola & Sons. This custom home set upon a perfect flat corner lot with lovely outdoor patio offers over 4,100 sqft of beautifully designed living space with an open-concept layout, encompassed by gorgeous Marvin windows providing abundant natural light,

    Melissa Montagno Higgins Group Real Estate

    706 Judd St, Fairfield, CT 06824
  • /40

    $1,430,000 Open Sat 11AM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 1,416 Sq Ft

    783 Post Rd E Unit 201, Westport, CT 06880

    AMAZING NEW CONSTRUCTION! Located in the heart of Westport, The Gables of Westport presents a collection of eight townhomes and five flats, blending sophisticated design with the ease of in-town living. Enjoy close proximity to Metro-North, major highways, Longshore Club & Park, Compo Beach, Levitt Pavilion, Westport Country Playhouse, fine dining, shopping, and entertainment. Crafted by local

    Todd Gibbons Boost Real Estate Group

    783 Post Rd E Unit 201, Westport, CT 06880
  • /40

    $1,395,000 Open Sat 11AM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 1,416 Sq Ft

    785 Post Rd E Unit 102, Westport, CT 06880

    AMAZING NEW CONSTRUCTION INCLUDING $25,000 IN EXTRAS! Located in the heart of Westport, The Gables of Westport presents a collection of eight townhomes and five flats, blending sophisticated design with the ease of in-town living. Enjoy close proximity to Metro-North, major highways, Longshore Club & Park, Compo Beach, Levitt Pavilion, Westport Country Playhouse, fine dining, shopping, and

    Todd Gibbons Boost Real Estate Group

    785 Post Rd E Unit 102, Westport, CT 06880
  • /37

    $1,099,000 Open House 4/11

    • 4 Beds
    • 2.5 Baths
    • 1,439 Sq Ft

    87 James St, Fairfield, CT 06824

    Welcome to 87 James Street, a beautifully renovated Cape Cod nestled on one of the most sought-after streets in Fairfield's coveted beach/town neighborhood. James St. is one of the "gems" of this community, where lifestyle & location come together effortlessly. Enjoy the convenience of walking to vibrant downtown Fairfield, the train station & the beach. Spend evenings strolling to the Town Green

    Heidi Cinder William Raveis Real Estate

    87 James St, Fairfield, CT 06824
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