Southport, CT Homes for Sale with Basement

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  $22,825,000

  • 8 Beds
  • 10 Baths
  • 12,946 Sq Ft

  11 Beachside Common, Westport, CT 06880

  Direct Waterfront | Greens Farms An extraordinary new waterfront estate by award-winning Coastal Luxury Homes is coming to one of the most coveted stretches of the Connecticut shoreline. Set in the heart of Greens Farms, this spectacular 12,948 square foot modern residence will span four levels and capture sweeping, unobstructed views across Sherwood Island, Burying Hill Beach, and Long Island

  Andrew Whiteley Brown Harris Stevens

  11 Beachside Common, Westport, CT 06880
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  /37

  $3,990,000

  • 5 Beds
  • 7 Baths
  • 7,409 Sq Ft

  13 Rockyfield Rd, Westport, CT 06880

  This pristine Colonial offers timeless Westport elegance and effortless living, set on 1.12 flat, manicured acres framed by classic stone walls in a coveted, quiet neighborhood just one hour from NYC. The five-bedroom home features five full and two half baths, two dedicated offices, two versatile bonus spaces, custom millwork throughout, and abundant storage-perfect for today's work-from-home,

  Danna Rogers Higgins Group Bedford Square

  13 Rockyfield Rd, Westport, CT 06880
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  /24

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  75 Hemlock St, Bridgeport, CT 06605

  Beautifully remodeled in 2024 1,300 SQFT cape cod right on the border of Fairfield. Take a look at the completely new home from the bottom up. New roof, new siding, new windows, new doors, new patio, new kitchen, new appliances, new hardwood floors, new insulation, new sheetrock, new wiring, new plumbing, new furnace, new hot water heater, new central air, new bathrooms. New vinyl fencing

  Jose Montilla eXp Realty

  75 Hemlock St, Bridgeport, CT 06605
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  /33

  $2,295,000

  • 4 Beds
  • 3 Baths
  • 3,099 Sq Ft

  140 Roseville Rd, Westport, CT 06880

  Perfectly sited on 1.59 acres, this 4-bedroom, 3-bath antique home invites a lifestyle defined by warmth, ease, and understated elegance. Original wideboard floors, an impressive hearth fireplace, and beautifully preserved details create a sense of history, while the open, light-filled layout supports a modern way of living-whether hosting gatherings or enjoying quiet moments at home. The main

  Emily Gordon Coldwell Banker Realty

  140 Roseville Rd, Westport, CT 06880
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  /32

  $5,185,000

  • 6 Beds
  • 8 Baths
  • 8,190 Sq Ft

  19 Mortar Rock Rd, Westport, CT 06880

  Stunning modern transitional home built by Compo Luxury Homes in 2024 and ideally located just minutes to downtown Westport, Compo Beach, and the train. Set on .65 acres with city water, sewer, and natural gas, this beautifully designed residence offers over 8,000 square feet across four finished levels with 6 bedrooms, 6 full and 2 half baths. The open floor plan features a chef's kitchen with

  Danna Rogers Higgins Group Bedford Square

  19 Mortar Rock Rd, Westport, CT 06880
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  /40

  $8,999,000

  • 7 Beds
  • 9 Baths
  • 10,482 Sq Ft

  19 Beachside Common, Westport, CT 06880

  Like-new custom modern home with open-concept living designed for comfort and entertaining. The main level connects the family room, dining room, office, and chef's kitchen featuring Sub-Zero and Wolf appliances, invisible speakers, quartzite countertops, custom cabinetry, two large islands and multiple sliding glass doors leading to an outdoor oasis. The spacious pantry includes custom shelving,

  Gina Hackett Compass Connecticut, LLC

  19 Beachside Common, Westport, CT 06880
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  /39

  $3,449,000

  • 5 Beds
  • 7 Baths
  • 5,515 Sq Ft

  2683 Bronson Rd, Fairfield, CT 06824

  In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate presents a rare opportunity in one of Fairfield's most coveted locations. Set on just over two acres of beautifully landscaped, professionally photographed grounds, the property reflects a timeless elegance that would be costly to replicate today. Across from a distinguished equestrian family

  Tara Hawley Coldwell Banker Realty

  2683 Bronson Rd, Fairfield, CT 06824
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  /40

  $1,975,000

  • 4 Beds
  • 3.5 Baths
  • 4,018 Sq Ft

  39 Marion Rd, Westport, CT 06880

  Nestled in the coveted Old Hill section of Westport, this exceptional residence offers a rare blend of space, serenity, & timeless appeal. With over 3,200 square feet, the home unfolds beautifully-beginning with a gracious entry foyer, leading into the living room with hardwood floors and anchored by a classic fireplace. The large eat-in kitchen offers double ovens, an abundance of cabinets and

  Stacy Pfannkuch Century 21 AllPoints Realty

  39 Marion Rd, Westport, CT 06880
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  /35

  $1,885,000

  • 3 Beds
  • 3.5 Baths
  • 3,805 Sq Ft

  491 Westway Rd Unit 491, Fairfield, CT 06890

  Located within the only gated enclave in the heart of Southport Village, this exceptional townhome offers a rare blend of privacy, convenience, and refined design. ELEVATOR READY! Just steps from Southport's charming shops, restaurants, train station, and beach, the setting is as desirable as it is walkable. This home spans three thoughtfully designed levels, each showcasing sophisticated,

  Denise Walsh William Raveis Real Estate

  491 Westway Rd Unit 491, Fairfield, CT 06890
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  /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
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  /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
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  /25

  $780,000

  • 2 Beds
  • 2 Baths
  • 1,733 Sq Ft

  206 Sterling St, Fairfield, CT 06825

  This charming cape has been beautifully maintained and thoughtfully updated, providing peace of mind and comfort throughout. Ideally located near all of the great amenities that Fairfield has to offer, with easy access to the Merritt and 95. The cozy dining area opens into a bright modern kitchen featuring marble countertops, updated appliances and a dry bar which is perfect for everyday living

  Sarah Callands Coldwell Banker Realty

  206 Sterling St, Fairfield, CT 06825
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  /36

  $559,900 Open Sat 12PM - 12:30PM

  • 5 Beds
  • 2.5 Baths
  • 2,403 Sq Ft

  1036-1038 Maplewood Ave, Bridgeport, CT 06605

  Renovated in 2025 this 2 family home features 11 Rooms, 5 Bedrooms, 2 Full & 1 Half Bathrooms. Apartment 1 features 5 Rooms, 2 Bedrooms, 1 Bathroom. Apartment 2 features 2 floors of living with 6 Rooms, 3 Bedrooms, 1 Full & 1 Half Bathroom. You are within a few minutes drive to everything including | 0.45 miles to I-95 | 0.5 miles to all major shopping | 1.1 miles to St Vincent hospital | 1.1

  Paul Ferreira RE/MAX Right Choice

  1036-1038 Maplewood Ave, Bridgeport, CT 06605
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  /40

  $3,000,000

  • 6 Beds
  • 5.5 Baths
  • 5,952 Sq Ft

  70 Meadow Ridge Rd, Fairfield, CT 06824

  Nestled on a picturesque cul-de-sac street in the heart of Southport, 70 Meadow Ridge Rd offers the perfect blend of classic charm and modern convenience. This custom home boasts 6 bedrooms and 5, Bathrooms providing ample space for comfortable living and entertaining. Step inside to discover sun-drenched living spaces featuring gleaming hardwood floors, a cozy fireplace, and an open-concept

  David Krasnoff Compass Connecticut, LLC

  70 Meadow Ridge Rd, Fairfield, CT 06824
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  $609,000

  • 5 Beds
  • 3 Baths
  • 2,328 Sq Ft

  8-10 Jetland Place, Bridge Port, CT 06605

  Located in the heart of Black Rock, this home is a fully rented multi-family opportunity in one of Bridgeport's most walkable and desirable neighborhoods. Two units are at or near market rent, with one unit currently below market offering immediate upside potential. Recent improvements include a new kitchen, bathroom, and flooring in the second-floor unit, a finished third-floor living area with

  Eric Garces BHGRE Gaetano Marra Homes

  8-10 Jetland Place, Bridge Port, CT 06605
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  /40

  $6,750,000

  • 6 Beds
  • 4 Baths
  • 3,572 Sq Ft

  27 Owenoke Park, Westport, CT 06880

  Welcome to 27 Owenoke Park, a timeless direct waterfront retreat, offering sweeping views where history, nature and Long Island Sound converge. Tucked away from NYC's hustle, yet close enough to commute, Owenoke Park has always been one of Westport's most coveted neighborhoods. Set directly on the Long Island Sound shoreline with over 80' of water frontage, including private access to the tidal

  Karen Scott Compass Connecticut, LLC

  27 Owenoke Park, Westport, CT 06880
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  /40

  $2,575,000

  • 6 Beds
  • 4.5 Baths
  • 5,083 Sq Ft

  4 the Fenway, Westport, CT 06880

  Timeless elegance in Westport's renowned Old Hill. Set on 2.22 bucolic acres w/a heated Gunite pool & picturesque pond, this expansive 5-6 bedroom,4.5 bath farmhouse blends classic charm w/thoughtful recent enhancements that delivers a renewed sense of style & energy to the home. A renovated kitchen remains the heart of the home, featuring a generous center island & a stunning, glass-walled

  Mary Kate Klemish-Boehm Brown Harris Stevens

  4 the Fenway, Westport, CT 06880
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  /40

  $2,800,000

  • 4 Beds
  • 2.5 Baths
  • 4,243 Sq Ft

  118 Roseville Rd, Westport, CT 06880

  This Westport residence is a meticulously executed Passive House retrofit of a modernist concrete home originally built in 1938. Few properties achieve this level of energy efficiency while also prioritizing non-toxic, health-conscious building materials. As you pass through the home's front entry gate and hear the gentle rhythm of tires over gravel, a striking and handsome facade comes into

  Tyler Della Valle Dow Della Valle

  118 Roseville Rd, Westport, CT 06880
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  /10

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,326 Sq Ft

  412 Dewey St, Bridgeport, CT 06605

  Welcome to this well-maintained single-family home in Bridgeport, CT featuring 4 spacious bedrooms and 2 full bathrooms. Enjoy an open and comfortable layout with central air, a finished basement perfect for additional living space or entertainment, and a nice backyard ideal for gatherings or relaxation. Conveniently located near schools, shopping, and major highways-this move-in-ready home

  Rosania Melo Rosania Melo Broker

  412 Dewey St, Bridgeport, CT 06605
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  /40

  $4,300,000

  • 6 Beds
  • 9 Baths
  • 9,525 Sq Ft

  278 North Ave, Westport, CT 06880

  Set in a coveted estate enclave prized by CEOs and captains of industry, this exceptional, shingle-style residence embodies timeless architecture, extraordinary craftsmanship, and meticulous attention to detail. Built custom for a CEO, the home showcases uncompromising quality and gracious curb appeal that leave a lasting impression. Designed for seamless indoor-outdoor living and grand-scale

  Cyd Hamer William Pitt Sotheby's Int'l

  278 North Ave, Westport, CT 06880
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  /16

  $240,000

  • 2 Beds
  • 2 Baths
  • 1,648 Sq Ft

  80 Cartright St Unit PHA, Bridgeport, CT 06604

  Very Rare Penthouse Unit on Top Floor with Large Balcony. Largest Unit in Complex, Over 1,600 Sq Ft. Two Large Bedrooms. Two Large Full Bathrooms. Picture Frame Molding Throughout unit. Crown Molding in Many Rooms. Hardwood and Parquet floors Throughout. Large Dining Room which opens up to Cozy Living Room with Sliders to the Balcony Providing Nice Vistas of the Surrounding Area. Storage Area and

  Christopher Ziko Higgins Group Real Estate

  80 Cartright St Unit PHA, Bridgeport, CT 06604
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  /38

  $1,799,000

  • 3 Beds
  • 3.5 Baths
  • 3,141 Sq Ft

  127 Spruce St, Southport, CT 06890

  Enjoy stylish and easy living in this spectacular townhome on Southport's storybook Spruce Street. Move in and enjoy or purchase as a reliable rental option, easy to manage with low HOA fees. Thoughtful design by renowned local architect Jack Franzen ensures a sophisticated and smart floor plan featuring top-quality finishes, high ceilings and beautiful wood floors. A great home for entertaining

  Ellen Fusco Compass Connecticut, LLC

  127 Spruce St, Southport, CT 06890
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  /40

  $3,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,283 Sq Ft

  1053 Fairfield Beach Rd, Fairfield, CT 06824

  Direct waterfront on premier Fairfield Beach with rare sandy frontage and sweeping, panoramic coastline views of the Long Island Sound. This sophisticated 3278sqft 4-bedroom residence offers an exceptional combination of elevation, privacy, and protection by two jetties. Extensively improved with over $400K in recent upgrades, the home is engineered for low-maintenance coastal luxury, featuring

  Mikhail Faifman William Raveis Real Estate

  1053 Fairfield Beach Rd, Fairfield, CT 06824
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  /31

  $874,999

  • 8 Beds
  • 4 Baths
  • 3,360 Sq Ft

  301 Poplar St Unit 303, Bridgeport, CT 06605

  Welcome to 301 Poplar Street, a well-maintained 4-unit multifamily property located in the sought-after Black Rock section of Bridgeport. This income-producing property includes a total of 8 bedrooms and 4 bathrooms, with each unit featuring 2 bedrooms and 1 bathroom. The building provides spacious layouts, separate utilities, and strong rental potential in a high-demand location. Ideal for

  Justin Sudol Alpha Capital Realty, LLC

  301 Poplar St Unit 303, Bridgeport, CT 06605
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  /24

  $399,000

  • 2 Beds
  • 1 Bath
  • 806 Sq Ft

  220 Melville Dr, Fairfield, CT 06825

  Welcome to 220 Melville Drive in Fairfield, a charming brick half duplex. Hardwood floors run throughout the home, beginning on the main level where a comfortable living room flows into the eat in kitchen perfect for everyday living and entertaining. Upstairs, the bedrooms offer a quiet retreat with natural light and updated bathroom with skylight. Outside, enjoy the convenience of a private two

  Lauren Iraeta KW Legacy Partners

  220 Melville Dr, Fairfield, CT 06825
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  /35

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 1,930 Sq Ft

  65 Benton St, Fairfield, CT 06825

  ATTENTION ALL!! This is 3 level townhouse in mint condition. Shining hardwood floors,large open kitchen with granite counters,stainless appliances and dining area plus a spacious family room. This stylish home offers three bedrooms, two and a half updated baths with marble floors and a roomy private master suite. Two other bedrooms are bright and sunny w/ lots of natural light through the entire

  Juan Garcia Sunbelt Sales & Development

  65 Benton St, Fairfield, CT 06825
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  /40

  $5,800,000

  • 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 acres just a short walk from town. 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

  Adrienne Durkin Compass Connecticut, LLC

  80 Compo Rd N, Westport, CT 06880
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  /34

  $249,900

  • 1 Bed
  • 1 Bath
  • 755 Sq Ft

  27 Nash Ln Unit 5, Bridgeport, CT 06605

  High end renovations that retain the charm of the historic Black Rock Garden Co-op complex! Custom kitchen with exposed brick, quartz countertops, stainless steel GE appliances, washer in hallway nook, floating glass shower, gorgeous hardwood floors throughout, hot water baseboard heat, insulated, tilt-in windows, and office with transom windows off living room/dining room. Open porch to enjoy

  Gail Robinson William Raveis Real Estate

  27 Nash Ln Unit 5, Bridgeport, CT 06605
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  /29

  $1,200,000

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

  97 Fayerweather Terrace, Bridgeport, CT 06605

  Fabulous 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.

  Steven Koleno Beycome of Connecticut

  97 Fayerweather Terrace, Bridgeport, CT 06605
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  /40

  $4,400,000

  • 5 Beds
  • 8 Baths
  • 9,819 Sq Ft

  1 Flower Farm Ln, Westport, CT 06880

  Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room

  Heather Fitzgerald Coldwell Banker Realty

  1 Flower Farm Ln, Westport, CT 06880
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  /16

  $789,000

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  37 Biro St, Fairfield, CT 06825

  Well-maintained two-family home in desirable Fairfield. Both units feature brand-new appliances and separate in-unit laundry, offering convenience and efficiency for owners or tenants. The roof is approximately 6 years old, and furnaces are about 10 years old, providing peace of mind and reduced capital expenses. Ideal for owner-occupants or investors seeking a solid multi-family property with

  Carlos Ventura Ventura Group Realty LLC

  37 Biro St, Fairfield, CT 06825
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  /19

  $850,000

  • 3 Beds
  • 3 Baths
  • 1,930 Sq Ft

  35 Knapps Hwy, Fairfield, CT 06825

  Welcome home to this beautifully remodeled cape which boasts 3 bedrooms, 3 full bathrooms, walk-in closets, stainless steel appliances, a finished lower level, a sun room and new, efficient mechanicals that keep energy costs down. The home is close to parks, shopping, golf, tennis courts, Fairfield's excellent schools and has a private, fenced back yard. There is plenty of parking in the attached

  Thomas Chanaca Chanaca Real Estate

  35 Knapps Hwy, Fairfield, CT 06825
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  /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
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  $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
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  /24

  $199,000

  • 1 Bed
  • 1 Bath
  • 1,093 Sq Ft

  80 Cartright St Unit 5D, Bridgeport, CT 06604

  Welcome to this bright and well-maintained condo offering comfort, convenience, and long-term value in one of the area's most established communities. This spacious unit features an open-concept living and dining area, an updated kitchen, generous bedroom space, and a private patio perfect for relaxing or entertaining. The building is in the midst of a major improvement plan that includes a

  Theresa Goulet Century 21 AllPoints Realty

  80 Cartright St Unit 5D, Bridgeport, CT 06604
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  /36

  $319,000

  • 3 Beds
  • 2 Baths
  • 1,755 Sq Ft

  25 Cartright St Unit 5D, Bridgeport, CT 06604

  Stunning End-Unit 3-Bedroom, 2-Bath NYC-Style Condo - Nestled in the heart of the highly sought-after Brooklawn community, this spacious 1,755 sq ft New York City-style condominium blends contemporary comfort with urban sophistication. Located just steps from the Fairfield town line, Unit 5D offers the perfect balance of city convenience and suburban tranquility. Step into a welcoming large foyer

  Pamela Williams Real Broker CT, LLC

  25 Cartright St Unit 5D, Bridgeport, CT 06604
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  $1,749,999

  • 16 Beds
  • 8 Baths
  • 5,824 Sq Ft

  25 Whittier St, Bridge Port, CT 06605

  Exceptional investment opportunity in Bridgeport's desirable Black Rock neighborhood. This 8-unit multifamily property features eight 2-bedroom, 1-bathroom units, each with spacious layouts ideal for tenants seeking comfort and convenience. The building is well-maintained, with separate utilities and strong rental history, making it a turnkey addition to any portfolio. Located just minutes from

  Zach Pinto Alpha Capital Realty, LLC

  25 Whittier St, Bridge Port, CT 06605
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  /40

  $2,395,000

  • 4 Beds
  • 4.5 Baths
  • 3,620 Sq Ft

  783 Reef Rd, Fairfield, CT 06824

  Welcome to 783 Reef Road, a beautifully crafted home in the highly desirable Penfield Beach area of Fairfield. This elegant residence combines refined design with modern comfort, offering four bedrooms, four and a half bathrooms, and approximately 3,620 square feet of interior living space and an additional nearly 1,400 square feet of basement storage space. Inside, the foyer opens to a layout

  Daniel Durante Criterion Real Estate LLC

  783 Reef Rd, Fairfield, CT 06824
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  /34

  $1,749,999

  • 16 Beds
  • 8 Baths
  • 5,824 Sq Ft

  31 Whittier St, Bridge Port, CT 06605

  Excellent investment opportunity in the heart of Bridgeport's Black Rock neighborhood. This 8-unit multifamily building features eight 2-bedroom, 1-bathroom units, each with spacious layouts and strong rental potential. The property includes separate utilities for each unit and has been well-maintained, making it ideal for investors seeking a stable, income-producing asset. Located just minutes

  Zach Pinto Alpha Capital Realty, LLC

  31 Whittier St, Bridge Port, CT 06605
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  /22

  $599,000

  • 2 Beds
  • 1.5 Baths
  • 930 Sq Ft

  376 Knapps Hwy, Fairfield, CT 06825

  Discover this impeccably remodeled townhouse, where every detail has been curated with a designer's eye. Wide-plank Brazilian hardwood floors set a sophisticated tone throughout, complemented by custom millwork, abundant natural light, and two balconies. The main living level offers a seamless, open flow. The kitchen blends modern lines with thoughtful craftsmanship, featuring an island, newer

  Dominika Wojciechowski Houlihan Lawrence

  376 Knapps Hwy, Fairfield, CT 06825

Showing Results 41 - 80, Page 2 of 4