Homes for Sale in Southport, CT with 5-Bedrooms

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  /40

  $2,995,000

  • 6 Beds
  • 7 Baths
  • 9,664 Sq Ft

  91 Algonquin Rd, Fairfield, CT 06825

  Iconic Georgian Manor. A rare offering of architectural significance, this distinguished 1922 Georgian Colonial is set on 1.88 acres of level, park-like grounds in a desirable Fairfield enclave. Encompassing over 10,000 square feet, this 6-bedroom estate seamlessly blends historic grandeur with elevated, modern living. A stately presence is immediately felt through classic Georgian symmetry,

  

  Danielle Malloy

  Serhant Connecticut, LLC

  (475) 271-2961

  91 Algonquin Rd, Fairfield, CT 06825
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  /34

  $869,900

  • 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

  

  Jorge Cintron

  Vylla Home (CT) LLC

  (475) 473-8158

  219 Orland St Unit 221, Bridgeport, CT 06605
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  /34

  $3,550,000

  • 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

  

  Susan Lieberman

  The Riverside Realty Group

  (475) 255-2758

  10 Winding Ln, Westport, CT 06880
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  /40

  $12,000,000

  • 7 Beds
  • 6.5 Baths
  • 8,119 Sq Ft

  260 Willow St, Southport, CT 06890

  Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every

  

  Libby Tritschler

  William Raveis Real Estate

  (203) 350-0943

  260 Willow St, Southport, CT 06890
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  /40

  $4,495,000 New Construction

  • 6 Beds
  • 9 Baths
  • 9,700 Sq Ft

  21 Warnock Dr, Westport, CT 06880

  This striking architectural design meets refined luxury in a meticulously crafted 9,700+/- 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 sophistication w/ premium finishes,

  

  Brett Lieberman

  The Riverside Realty Group

  (203) 717-5836

  21 Warnock Dr, Westport, CT 06880
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  /40

  $4,650,000

  • 5 Beds
  • 7 Baths
  • 8,550 Sq Ft

  49 Hillspoint Rd, Westport, CT 06880

  Tucked away in the heart of Westport, Hillspoint offers the perfect blend of luxury, lifestyle and location. Minutes to Longshore Club Park, Compo Beach, town and train, it delivers rare privacy with exceptional convenience. Inside, soaring ceilings and sun-filled spaces create a light, airy flow enhanced by high-end finishes throughout. Designed for everyday living and effortless entertaining,

  Michelle Genovesi William Raveis Real Estate

  49 Hillspoint Rd, Westport, CT 06880
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  /38

  $6,195,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,550 Sq Ft

  22 Apple Tree Trail, Westport, CT 06880

  Located on a quiet private lane just two blocks from Compo Beach, this newly built coastal residence at 22 Appletree Trail offers a rare combination of modern craftsmanship, thoughtful design, and effortless beach living in the heart of Westport. Spanning approximately 4,791 sq ft of living space, the home blends timeless architectural elements with refined contemporary finishes. White oak

  Deborah Aulfinger Gold & Home Realty

  22 Apple Tree Trail, Westport, CT 06880
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  /40

  $2,850,000

  • 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
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  /25

  $500,000

  • 7 Beds
  • 3 Baths
  • 2,784 Sq Ft

  36 Lee Ave Unit 38, Bridgeport, CT 06605

  This well-maintained two-family home features two spacious units, each with three bedrooms, offering ample living space and comfortable layouts. In excellent condition, the property presents a versatile opportunity for owner-occupants seeking rental income or investors pursuing a strong, income-producing asset. Located in a highly desirable area with solid appreciation and future growth

  Angel Mora eXp Realty

  36 Lee Ave Unit 38, Bridgeport, CT 06605
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  /27

  $680,000

  • 6 Beds
  • 4 Baths
  • 2,860 Sq Ft

  5 Durando Place, Bridgeport, CT 06605

  Exceptional Black Rock Two-Family | Bridgeport, CT A rare opportunity in one of Bridgeport's most sought-after neighborhoods Welcome to this beautifully expanded two-family home nestled in the heart of Black Rock - a charming 1936 residence that masterfully blends timeless period character with thoughtful modern updates. First Floor Unit offers 2 spacious bedrooms and 2 full baths, plus a

  Shelly Olivadoti Berkshire Hathaway NE Prop.

  5 Durando Place, Bridgeport, CT 06605
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  /40

  $2,999,000

  • 5 Beds
  • 6 Baths
  • 5,924 Sq Ft

  127 Field Rock Rd, Southport, CT 06890

  Welcome to this exceptional newer Colonial nestled in a highly desirable Southport location, where timeless elegance meets modern luxury. Custom built with impeccable attention to detail, this stunning home offers three expansive levels of beautifully finished living space, perfectly designed for both everyday living and entertaining. Set on 1.68 acres of lush, manicured grounds, the property

  Sara Santos Coldwell Banker Realty

  127 Field Rock Rd, Southport, CT 06890
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  /40

  $2,800,000

  • 5 Beds
  • 5.5 Baths
  • 8,925 Sq Ft

  145 Galloping Hill Rd, Fairfield, CT 06824

  Exceptional scale and timeless elegance define this impressive 5-bedroom, 6-bath residence offering over 8,200 square feet of refined living space in one of Fairfield's most desirable locations. Thoughtfully designed for both grand entertaining and comfortable everyday living, the home features expansive sun-filled rooms, high ceilings, and a seamless flow throughout the main living areas. A

  Susan Gardella William Pitt Sotheby's Int'l

  145 Galloping Hill Rd, Fairfield, CT 06824
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  /22

  $1,400,000

  • 6 Beds
  • 4 Baths
  • 4,485 Sq Ft

  135 Grace St, Fairfield, CT 06825

  Tucked away at the end of a quiet dead-end street, this beautifully maintained property consists of two half duplex units, offering in each approximately 1,950 square feet of thoughtfully designed, open-concept living space - perfect for both everyday living and entertaining. The property features a spacious, private fenced-in yard, ideal for outdoor gatherings, or simply relaxing in your own

  Matt Lahey Higgins Group Real Estate

  135 Grace St, Fairfield, CT 06825
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  /40

  $2,950,000

  • 6 Beds
  • 5.5 Baths
  • 5,938 Sq Ft

  36 Bauer Place, Westport, CT 06880

  Better than new! This beautifully appointed 4-level home blends contemporary design with warmth, comfort, and thoughtful upgrades throughout. The heart of the home is a cook's dream kitchen with gourmet appliances, a full pantry, and a massive center island showcasing stunning finishes. Designed for both beauty and function, it opens seamlessly to the bright, welcoming family room. Together,

  Jennifer Twombly Compass Connecticut, LLC

  36 Bauer Place, Westport, CT 06880
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  /30

  $840,000

  • 6 Beds
  • 3 Baths
  • 2,142 Sq Ft

  65 Mason St, Fairfield, CT 06825

  Excellent investment opportunity at the end of a quiet cul-de-sac! This well-maintained 2-family property offers strong rental potential and a highly desirable location with convenient access to transportation, Route 1 shopping, and I-95. First Floor Unit: This 3-bedroom, 1-bath unit features hardwood floors, a bright white kitchen with stainless steel appliances, full-size washer and dryer, and

  Matt Lahey Higgins Group Real Estate

  65 Mason St, Fairfield, CT 06825
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  /26

  $8,995,000

  • 8 Beds
  • 10 Baths
  • 15,172 Sq Ft

  2 Judy Point Ln, Westport, CT 06880

  Set on over 3 private acres with sweeping water views, 2 Judy Point Lane is a remarkable Westport waterfront estate offering approximately 14,000 square feet of living space and a rare compound-style layout. The property consists of two substantial residences connected by a breezeway, creating exceptional flexibility for multi-generational living, extended guests, or a private guest house.

  Daniel Kramp Christie's International Real Estate

  2 Judy Point Ln, Westport, CT 06880
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  /6

  $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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  /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

  $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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  /40

  $2,850,000

  • 6 Beds
  • 5.5 Baths
  • 4,322 Sq Ft

  598 S Benson Rd, Fairfield, CT 06824

  Rare Beach Property~ Steps to Sandcastle Playground, Jennings Beach and South Benson Marina - this striking Colonial delivers a unique blend of luxurious beach living and exceptional build quality. Homes of this caliber seldom become available along the shoreline. ~ EXPANSIVE FIRST FLOOR ~ The house features a sprawling first floor Great Room and show stopping Chef's Kitchen which combine in a

  Julie Vanderblue Higgins Group Real Estate

  598 S Benson Rd, Fairfield, CT 06824
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  /36

  $559,900

  • 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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  /32

  $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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  /2

  $4,300,000

  • 6 Beds
  • 6 Baths
  • 6,000 Sq Ft

  394 Penfield Rd, Fairfield, CT 06824

  IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7

  Helene Salerno Ogents, LLC

  394 Penfield Rd, Fairfield, CT 06824
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  /2

  $4,300,000

  • 6 Beds
  • 6 Baths
  • 6,000 Sq Ft

  378 Penfield Rd, Fairfield, CT 06824

  IMAGES FROM BUILDER'S PORTFOLIO.Remarkable CUSTOMIZABLE approx 6,000 Sqft New Beach Construction Home on a very RARE OVERSIZED 0.31 acre lot with a non-pareil luxurious Open floor plan on the Premier street in beach area ! Situated just two blocks away from Penfield Beach. Created by Master Local Builder; NEW GENERATION HEALTHY HOMES. Custom designed to offer state of the art amenities, 7

  Helene Salerno Ogents, LLC

  378 Penfield Rd, Fairfield, CT 06824
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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

  $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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  /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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  /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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  /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
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  /39

  $2,950,000

  • 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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  /33

  $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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  /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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  /12

  $630,000

  • 6 Beds
  • 3 Baths
  • 3,069 Sq Ft

  195 Lenox Ave Unit 197, Bridgeport, CT 06605

  Welcome to 195 Lenox Avenue - a modern and versatile 3-family home perfect for both investors and first-time buyers. With 6 bedrooms, 3 full bathrooms, and a full basement, this property offers plenty of space and excellent rental potential. The first and second floors each allow for an extra bedroom conversion, maximizing cash flow. Inside, the units are updated and well-maintained, providing

  Shafran Salim Guy Bocicaut Real Estate

  195 Lenox Ave Unit 197, Bridgeport, CT 06605
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  /7

  $755,000

  • 5 Beds
  • 3 Baths
  • 2,483 Sq Ft

  855 Brewster St Unit 857, Bridgeport, CT 06605

  An incredible investment opportunity in a highly desirable Black Rock Neighborhood. This well maintained 3 Family property is perfect for investors or owner occupied. Ideally located within walking distance to the Fairfield Metro Train Station, shops and restaurants along Fairfield Ave. It's a short drive to I-95 and Downtown Fairfield and Black Rock Turnpike. This 3 Family home has 5 Bedrooms, 3

  Doug Munson Munson Real Estate

  855 Brewster St Unit 857, Bridgeport, CT 06605
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  /39

  $2,200,000

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

  2142 Fairfield Beach Rd, Fairfield, CT 06824

  OPPORTUNITY KNOCKS TWICE with the only two-family home on Fairfield beach road Peninsula. Great rental income. Newly painted inside and out and completely furnished. This duplex features a spacious four-bedroom unit and a two-bedroom unit on the creek side with private gate access to the beach just across the road. Features include a wrap-around deck on the creek side with boat access to Long

  Michael Menillo Collage Realty

  2142 Fairfield Beach Rd, Fairfield, CT 06824

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