Southport, CT Homes for Sale

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  /35

  $1,289,000

  • 4 Beds
  • 3.5 Baths
  • 2,166 Sq Ft

  20 Whetstone Hill Ct, Fairfield, CT 06824

  Some homes simply grow with you - and this is one of them. Nestled on a quiet cul-de-sac in a sought-after beach neighborhood, this inviting home has been the backdrop for years of cherished memories. Designed with both comfort and flexibility in mind, its thoughtful layout easily adapts to changing lifestyles. A legal studio - with a private entrance, full bathroom and kitchenette - offers

  Alina Rodescu-Pitchon William Raveis Real Estate

  20 Whetstone Hill Ct, Fairfield, CT 06824
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  /24

  $175,000

  • 1 Bed
  • 1 Bath
  • 629 Sq Ft

  80 Cartright St Unit 8E, Bridgeport, CT 06604

  Here's one that won't sit on the market long. This 1-bedroom in Cartright Towers sits right on the Fairfield/Bridgeport line and offers a rare combination for the price point: move-in ready condition, low-maintenance living, and a location that puts everything within reach. Inside, you'll find newer LVP flooring throughout, a ceiling fan in the bedroom, and a kitchen outfitted with stainless

  Daniel Durante Criterion Real Estate LLC

  80 Cartright St Unit 8E, Bridgeport, CT 06604
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  /9

  $599,000

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  11 Redfield Rd, Fairfield, CT 06824

  Located on a cul-de-sac, walking distance to Fairfield's desirable downtown which offers great shopping, restaurants & easy access to the Metro North Train Station that brings you into Grand Central Station, the heart of NYC, in @ 70 minutes! Walk to the Town Gazebo which hosts Sunday Farmer's Market & live music in the summer! A Short bike ride to the Fairfield coastline with beautiful beaches

  Heidi Cinder William Raveis Real Estate

  11 Redfield Rd, Fairfield, CT 06824
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  /39

  $5,925,000

  • 6 Beds
  • 9 Baths
  • 6,561 Sq Ft

  3 Stony Point W, Westport, CT 06880

  Located within the highly desirable Stony Point association, this exceptional home offers a rare combination of privacy, water views, and convenience just moments from the train, local restaurants, and everyday amenities. This particular home enjoys private dock membership, providing summer boat access just steps from your door. Completely transformed and expanded in 2016, the home features over

  Debra Shaughnessy Coldwell Banker Realty

  3 Stony Point W, Westport, CT 06880
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  /27

  $1,995,000

  • 3 Beds
  • 3.5 Baths
  • 3,328 Sq Ft

  2 Elmwood Dr Unit 2, Southport, CT 06890

  Enjoy the privacy of a stand-alone home with the effortless convenience of condominium living in coveted Southport Green. One of only two detached residences in this desirable 24-home community, the three-level property offers three bedrooms, three renovated full baths, a powder room, and an attached two-car garage. A private patio-an uncommon amenity within the enclave-provides a peaceful

  Wendy Ryan Brown Harris Stevens

  2 Elmwood Dr Unit 2, Southport, CT 06890
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  /16

  $1,899,000

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

  36 Lyons Plain Rd, Westport, CT 06880

  Rarely does an opportunity like this become available in Westport. Set on 2.36 private acres with approximately 300 feet along the scenic Aspetuck River, this exceptional property offers a remarkable setting to renovate, expand, or create the custom estate you've always envisioned. The existing four-bedroom residence features a spacious primary suite with fireplace, an expansive kitchen, and a

  Charlotte Cotton William Raveis Real Estate

  36 Lyons Plain Rd, Westport, CT 06880
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  /20

  $6,495,000

  New Construction

  • 6 Beds
  • 8 Baths
  • 9,062 Sq Ft

  5 Baldwin Place, Westport, CT 06880

  Rarely does a new construction home and property like this come on the market in Westport. Set at the end of a cul-de-sac, in the coveted Long Lots neighborhood, this 2.3-acre, flat property offers a rare combination of privacy and convenience to town. The property features a resort-style, saltwater pool w/spa and automatic safety cover, expansive covered and open-air patios, and a fully equipped

  Lori Popkin Coldwell Banker Realty

  5 Baldwin Place, Westport, CT 06880
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  /40

  $5,499,000

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

  2268 Fairfield Beach Rd, Fairfield, CT 06824

  Experience the pinnacle of coastal luxury at this extraordinary waterfront builder's own residence on prestigious Fairfield Beach Road. Designed with uncompromising craftsmanship and impeccable attention to detail, this one-of-a-kind modern masterpiece offers the ultimate waterfront lifestyle with a private sandy beach and your own private dock. Showcasing over-the-top custom finishes throughout,

  Sara Santos Coldwell Banker Realty

  2268 Fairfield Beach Rd, Fairfield, CT 06824
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  /2

  $2,650,000

  • Land
  • 1.23 Acres
  • $2,154,472 per Acre

  4 Lantern Hill Rd, Westport, CT 06880

  Rare opportunity to build a custom residence on 1.2 acres in Westport. The previous home has been demolished, and the property is offered with approved architectural plans. Bring your preferred builder and collaborate with the project architect to tailor the design to your vision. Also listed as a to-be-built single-family residence.

  Ian Defronze Serhant Connecticut, LLC

  4 Lantern Hill Rd, Westport, CT 06880
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  /34

  $970,000

  Open Sat 11AM - 1PM

  • 2 Beds
  • 2 Baths
  • 1,792 Sq Ft

  134 Shoreham Village Dr, Fairfield, CT 06824

  Water Views! Unforgettable sunsets and a front-row seat to Fairfield's Fourth of July fireworks-this is the Fairfield Beach community lifestyle! Designed for everyday living and effortless entertaining, this move-in-ready two-bedroom home offers an inviting flow from the living and dining rooms to the newly renovated sunroom and spacious, newly refurbished AZEK deck. Whether hosting summer

  John Harvey Compass Connecticut, LLC

  134 Shoreham Village Dr, Fairfield, CT 06824
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  /40

  $2,790,000

  • 5 Beds
  • 3 Baths
  • 3,072 Sq Ft

  56 Charcoal Hill Rd, Westport, CT 06880

  A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail,

  Doug Bross Coldwell Banker Realty

  56 Charcoal Hill Rd, Westport, CT 06880
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  /15

  $1,179,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1646 Jennings Rd, Fairfield, CT 06824

  Completely renovated from top to bottom, this stunning 4-bedroom, 2-bath home blends modern luxury with timeless charm in Fairfield's desirable University area. Offering 1,814 sq ft of finished living space plus an 884 sq ft unfinished basement, this move-in-ready home delivers style, comfort, and future potential. The open-concept layout centers on a designer kitchen with custom cabinetry, an

  Nijat Binnatov Realty ONE Group Connect

  1646 Jennings Rd, Fairfield, CT 06824
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  /19

  $199,000

  • 1 Bed
  • 1 Bath
  • 764 Sq Ft

  25 Ellsworth St Unit 6, Bridgeport, CT 06605

  Welcome to life at HARBOR HOUSE: Because WHERE you life should be a reflection of HOW you live. Directly across the street, enjoy pristine Ellsworth Park with pickleball/tennis courts, playground, splash pad, ball fields, yoga classes, and picnic area. Just down the road, join friends at Fayerweather Yacht Club for social events, boating, or dinner and drinks at sunset along the waterfront. If

  Kaitlyn Walsh William Raveis Real Estate

  25 Ellsworth St Unit 6, Bridgeport, CT 06605
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  /37

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,074 Sq Ft

  430 Berkeley Rd, Fairfield, CT 06825

  Lovely 4 Bedrooms and 3 Full Bath Cape built in 1986 is ready to move-in. House has many updates including new Kitchen countertops, Newer roof, water heater and much more. Private deck converted to paved parking and play area for children and finished basement. The house offers Spacious primary bedroom and full bathroom on first floor along with updated kitchen - new Quartz countertops, newer

  Aziz Seyal William Raveis Real Estate

  430 Berkeley Rd, Fairfield, CT 06825
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  /27

  $2,100,000

  $100K PRICE DROP

  • 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
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  /39

  $2,699,000

  Coming Soon

  • 5 Beds
  • 5.5 Baths
  • 5,014 Sq Ft

  1123 Round Hill Rd, Fairfield, CT 06824

  There's a certain kind of iconic home that settles over you the moment you step inside, because the craftsmanship was never meant to be temporary. Nine-foot ceilings in the living & dining rooms, 3 wood-burning fireplaces, solid proportions & large windows & glass doors that still frame the light the way they were designed to nearly a century ago. The kind of quiet authority that newer

  Veronica Monahan Compass Connecticut, LLC

  1123 Round Hill Rd, Fairfield, CT 06824
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  /36

  $5,750,000

  • 5 Beds
  • 8 Baths
  • 6,503 Sq Ft

  31 Stonybrook Rd, Westport, CT 06880

  Tucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a rare blend of elegance, privacy and natural beauty. The property has multiple serene water features-a heated saltwater gunite pool with hot tub, a tranquil private pond with fountain and picturesque Stony Brook. The stately stone and wood exterior blends seamlessly with the lush surroundings, while inside, an

  Kristi Law William Pitt Sotheby's Int'l

  31 Stonybrook Rd, Westport, CT 06880
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  /7

  $479,500

  • 6 Beds
  • 2 Baths
  • 3,419 Sq Ft

  52-54 Clinton Ave, Bridgeport, CT 06605

  INVESTMENT OPPORTUNITY!! Don't miss this versatile two-family offering strong income potential. Featuring six Bedrooms Two full baths. Offers flexible with expansion. Attic offers added value. Roof is two years old. Mechanics all in working order. Property being sold As-Is. Bring your ideas and unlock the full potential this income-producing property!

  William Ferguson Brown Harris Stevens

  52-54 Clinton Ave, Bridgeport, CT 06605
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  /39

  $2,225,000

  $25K PRICE INCREASE

  • 6 Beds
  • 2 Baths
  • 2,180 Sq Ft

  2142 Fairfield Beach Rd, Fairfield, CT 06824

  OPPORTUNITY KNOCKS TWICE - A unique investment awaits with the only two-family home on the Fairfield Beach Road Peninsula featuring private beach access. This fully furnished property offers excellent rental income during the academic season and serves as a relaxing summer retreat for owners-or an additional rental opportunity. Unit 2142 is a spacious four-bedroom residence, each room furnished

  Michael Menillo Collage Realty

  2142 Fairfield Beach Rd, Fairfield, CT 06824
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  /31

  $1,189,000

  • 3 Beds
  • 2.5 Baths
  • 1,738 Sq Ft

  150 Sherman Ct, Fairfield, CT 06824

  First time on the market in over 25 years! This exceptional Victorian-style townhouse is tucked away on a quiet cul-de-sac in the heart of Downtown Fairfield, offering timeless character, thoughtful updates, and an unbeatable location. A dramatic two-story foyer with a skylight welcomes you into the spacious living and dining rooms featuring wide-plank wood floors, deep crown moldings, and a

  Pat Conroy Higgins Group Bedford Square

  150 Sherman Ct, Fairfield, CT 06824
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  /17

  $259,900

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  65 Ellsworth St Unit 303, Bridgeport, CT 06605

  The Cove Of Black Rock! Move in condition first floor, one bedroom unit with an open floor plan, newer kitchen, bathroom, heating and ac and offers an in unit washer and dryer and a full basement for storage. This affordable unit is located between Captain's Cove Seaport, Fayerweather Yacht Club, Port 5 Naval Veterans Club, S.S. Norden Club and the Black Rock Yacht Club, a boater's paradise.

  John Kleps Berkshire Hathaway NE Prop.

  65 Ellsworth St Unit 303, Bridgeport, CT 06605
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  /22

  $995,000

  $100K PRICE DROP

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

  18 Hurd St, Fairfield, CT 06824

  Welcome home to this charming and beautifully maintained 3-bedroom, 2-full-bath ranch offering the perfect blend of comfort, convenience, and lifestyle. Ideally situated just moments from the beach, downtown, and the train, this home puts everything you love right at your fingertips. Step inside to discover a warm and inviting floor plan designed for easy everyday living. The spacious living area

  Adam Wagner Keller Williams Prestige Prop.

  18 Hurd St, Fairfield, CT 06824
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  /29

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 1,406 Sq Ft

  97 Fayerweather Terrace, Bridgeport, CT 06605

  Fabulous BlackRock Remodeled 4 Bedroom main house with Open floor plan. Partially finished basement. New Energy Star Appliances, Solar and beautifully appointed. Detached 2 Car Garage with One bedroom one bath unit above. Close to train, restaurants, St. Mary's by the Sea. Not available until July of 2027.

  Steven Koleno Beycome of Connecticut

  97 Fayerweather Terrace, Bridgeport, CT 06605
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  /29

  $1,899,000

  • 3 Beds
  • 2.5 Baths
  • 3,338 Sq Ft

  23 Old Dam Rd, Fairfield, CT 06824

  Wonderful waterfront oasis offers direct access to Long Island Sound via a private dock and includes deeded Fairfield beach access. The home features a bright, open floor plan, creating an inviting coastal atmosphere. The primary bedroom boasts a sitting room, a walk-in closet, and a balcony overlooking the waterfront, providing stunning views of LI Sound & Pine Creek. The property promises

  Katie O'Grady Compass Connecticut, LLC

  23 Old Dam Rd, Fairfield, CT 06824
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  /40

  $3,499,000

  • 5 Beds
  • 4.5 Baths
  • 3,778 Sq Ft

  240 North Ave, Westport, CT 06880

  "MEADOW WOOD" - Nearly two acres of Westport's most spectacular land is the setting for this storied estate, which has been completely remodeled, expanded and transformed for modern living. Totally fenced & screened w/privacy trees, this unique property offers rare sophistication with a stunning main residence, gunite pool, and a 2,447+/- sqft barn. Gated driveways lead to both the main house &

  Doug Bross Coldwell Banker Realty

  240 North Ave, Westport, CT 06880
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  /40

  $2,950,000

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft

  679 Rowland Rd, Fairfield, CT 06824

  Ideally located in one of Fairfield's most desirable beach neighborhoods, this beautiful custom-built FEMA compliant home combines premium construction and efficiency with high-end finishes throughout. Unique features include 2x6 framing, steel beam support, energy efficient foam insulation, dual HVAC and tankless hot water systems, a gorgeous custom kitchen with Thermador appliances and honed

  Amie Belile William Raveis Real Estate

  679 Rowland Rd, Fairfield, CT 06824
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  /2

  $1,150,000

  • Land
  • 37,897 Sq Ft
  • $1,321,839 per Acre

  119 Kings Highway North Rd, Westport, CT 06880

  Don't miss this great opportunity close to town. The .87Acre lot is elevated ,rolling and ideally positioned off Kings Highway. There are distance views of the river and town through the trees. There is an older small 1400 sq ft. single family home that has been a rental for many years. The previous owners in the 30's made each floor into apartments. Each level with its own entrance features a

  Helen Cusa Brown Harris Stevens

  119 Kings Highway North Rd, Westport, CT 06880
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  /32

  $1,329,000

  • 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 shopping, dining & recreation, this lovely in-town home offers a rare blend of comfort, flexibility, and location. The inviting living room with wood-burning fireplace sets the tone for relaxed gatherings and quiet evenings alike. The open-concept kitchen features granite countertops and flows

  Barbara Bross Coldwell Banker Realty

  310 Main St, Westport, CT 06880
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  /40

  $5,750,000

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

  69 Birch Rd, Fairfield, CT 06824

  Your new fully custom near beach luxury residence is ready for you now... Introducing "White Birch", a masterfully executed collaboration between Fairfield County's premier Architect, Builder, & Designer, sets a new benchmark for bespoke coastal living and the effortless estate lifestyle. Every detail has been thoughtfully curated, every finish intentionally elevated, every inch built with

  Jaclyn Picarillo Higgins Group Bedford Square

  69 Birch Rd, Fairfield, CT 06824
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  /32

  $1,495,000

  Coming Soon

  • 1 Bed
  • 1.5 Baths
  • 1,026 Sq Ft

  236 Main St Unit 236, Southport, CT 06890

  A rare opportunity to own in the heart of historic Southport Village for under $1.5 million. Beautifully redesigned by the renowned Michael Greenberg & Associates of Westport, this sophisticated two-level residence is located within a landmark building overlooking Southport Harbor. Offering one of the few opportunities to own in Southport Village at this price point, it is ideally suited as a

  Andrew Whiteley Brown Harris Stevens

  236 Main St Unit 236, Southport, CT 06890
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  /27

  $1,495,000

  • 1 Bed
  • 1 Bath
  • 1,551 Sq Ft

  11 Hitchcock Rd, Westport, CT 06880

  An exceptional offering on 1.38 private acres in the heart of Westport. Ideally situated just moments from vibrant Main Street, this centrally located property offers convenient access to shopping, dining, parks, tennis courts, beaches, the train, and Westport's award-winning schools. It provides an outstanding foundation for creating a one-of-a-kind estate. At the heart of this property stands

  Kelley Long Thrush Berkshire Hathaway NE Prop.

  11 Hitchcock Rd, Westport, CT 06880
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  /15

  $300,000

  • 2 Beds
  • 1 Bath
  • 624 Sq Ft

  11 Knapps Park Dr, Fairfield, CT 06825

  Rare opportunity to own a strong-performing investment property or simply enjoy the ease of one-level living in this charming ranch-style duplex that lives very much like a single-family home! A wonderful condo alternative with no HOA fees or restrictions, enjoy a spacious private fenced backyard, charming patio for outdoor dining, and a quiet setting in coveted Fairfield. This home offers

  Melissa Montagno Higgins Group Real Estate

  11 Knapps Park Dr, Fairfield, CT 06825
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  /24

  $724,900

  $25K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,350 Sq Ft

  385 Unquowa Rd Unit 385, Fairfield, CT 06824

  Welcome to 385 Unquowa Road, a beautifully maintained 2-bedroom, 2.5-bath townhouse in the heart of Fairfield that truly stands apart from the rest. Thoughtfully upgraded throughout, this turnkey home showcases a beautifully redesigned kitchen with an expanded, more open layout that offers significantly more counter space and functionality than comparable units. Renovated cabinetry, updated

  Michael DeGrosse Luxe Realty LLC

  385 Unquowa Rd Unit 385, Fairfield, CT 06824
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  /13

  $142,900

  $12K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft

  78 Haddon St Unit 1, Bridgeport, CT 06605

  Vibrant Black Rock community convenient to all. Unusually large square footage. Convenient 1st floor end unit. In need of updates but generally in good condition. Great opportunity to refresh to your taste. Please review coop sales process document; it is integral to completely understanding procedure & costs involved with this property's purchase.

  Todd Debek Debek Real Estate Services LLC

  78 Haddon St Unit 1, Bridgeport, CT 06605
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  /34

  $1,399,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,300 Sq Ft

  30 Country Rd, Fairfield, CT 06824

  This brand-new construction masterpiece showcases an elite architectural design that prioritizes complete autonomy. The two separate units share absolutely no living space walls-the only common point of contact is the garage structure, ensuring the noise control and privacy of a fully detached single-family home. Each residence features its own distinct, privately sectioned, and fully fenced

  Denise Daniels-biagi Coldwell Banker Realty

  30 Country Rd, Fairfield, CT 06824
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  /40

  $4,850,000

  • 5 Beds
  • 5 Baths
  • 5,103 Sq Ft

  22 Evergreen Ave, Westport, CT 06880

  Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate

  Valerie Alvarez Serhant Connecticut, LLC

  22 Evergreen Ave, Westport, CT 06880
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  /34

  $925,000

  $24K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,166 Sq Ft

  7 Lincoln St, Westport, CT 06880

  A wonderful opportunity to make this home your own. The property offers the potential to be converted back into a single-family residence and is ideally located just moments from vibrant Main Street, Saugatuck Village, the train station, and local schools. Two washers Two dryers Three dishwashers

  Georgia Wasserman Coldwell Banker Realty

  7 Lincoln St, Westport, CT 06880
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  /36

  $3,999,500

  $2M PRICE DROP

  • 3 Beds
  • 4.5 Baths
  • 2,528 Sq Ft

  1681 Fairfield Beach Rd, Fairfield, CT 06824

  Rarely does a property offer frontage on both Long Island Sound and South Pine Creek. Positioned along a naturally elevated stretch of Fairfield Beach framed by protective dunes, the property enjoys a broad sandy beach at both high and low tide. Located within a residential section of Fairfield Beach away from many public beach access points, the setting offers a unique combination of beach,

  Stephanie Barnes William Raveis Real Estate

  1681 Fairfield Beach Rd, Fairfield, CT 06824
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  /14

  $8,696,000

  New Construction

  • 7 Beds
  • 8 Baths
  • 9,422 Sq Ft

  688 Hulls Farm Rd, Southport, CT 06890

  Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 688 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury

  Jaclyn Picarillo Higgins Group Bedford Square

  688 Hulls Farm Rd, Southport, CT 06890
• 

  

  /40

  $1,949,000

  • 4 Beds
  • 3.5 Baths
  • 4,492 Sq Ft

  125 Coleman Rd, Fairfield, CT 06825

  Inspired by today's most sought-after Organic Modern homes, this custom residence blends clean architectural lines, warm natural materials, and highly functional living spaces to create a home that is as beautiful as it is livable. This newly constructed 4-bedroom, 3.5-bath custom home offers approximately 4,500 square feet of refined living on a private, level lot, showcasing exceptional

  Amanda Foss Keller Williams Prestige Prop.

  125 Coleman Rd, Fairfield, CT 06825

Showing Results 121 - 160, Page 4 of 5