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Homes for Sale near Capital Prep Harbor Upper School

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  • /40

    $499,900

    • 3 Beds
    • 1 Bath
    • 1,291 Sq Ft

    5167 Main St, Trumbull, CT 06611

    Completely reimagined, this 1920 charmer pairs century-old character with a brand-new 2026 renovation. A welcoming covered front porch opens to a sun-drenched living space with wide-plank waterproof laminate wood flooring, recessed lighting, sleek black triple-pane windows, and a stone-accented fireplace. The showstopper kitchen features custom sage green cabinetry with brushed gold hardware and

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    Kristin Egmont

    Coldwell Banker Realty

    5167 Main St, Trumbull, CT 06611
  • /40

    $649,900

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    1770 Stratfield Rd, Fairfield, CT 06825

    A beautifully refreshed home with classic New England charm that meets thoughtful modern upgrades. The moment you arrive, you're greeted by curated yard plantings, a freshly seeded, level, fenced backyard that invites everything from weekend gatherings to quiet mornings outdoors. Inside, the first floor opens up into a bright, open floor plan layout designed for how you actually live-connecting

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    Alan Stewart Jr.

    ASJ Realty Partners

    1770 Stratfield Rd, Fairfield, CT 06825
  • /26

    $379,900

    • 1 Bed
    • 1.5 Baths
    • 1,080 Sq Ft

    53 Ferry Ct, Stratford, CT 06615

    Beautifully renovated potential 2BR townhouse in Stratford's hidden waterfront community, Village Square. Modern kitchen with white shaker cabinets, quartz counters, tiled backsplash, stainless steel appliances, and 5burner gas cooktop. Luxury vinyl plank flooring, smooth ceilings, and updated baths create a clean, move-in ready interior. Enjoy afternoon sunshine from your private deck.

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    Elizabeth Heatter

    YellowBrick Real Estate LLC

    53 Ferry Ct, Stratford, CT 06615
  • /36

    $435,000

    • 3 Beds
    • 2 Baths
    • 1,783 Sq Ft

    144 Mary Ave, Stratford, CT 06614

    Welcome to your new chapter in real estate! This currently, single family home offers more potential than meets the eye...read on! It is a 3 bedroom home at this time featuring hardwood flooring, a main level bedroom and full bathroom and a living room and dining room. You have a completely separate entrance that can work for the upstairs 2 bedrooms if that is more of what you have in mind. The

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    Mary Beth Grasso

    Keller Williams Realty

    144 Mary Ave, Stratford, CT 06614
  • /30

    $419,000

    Open Sat 2PM - 4PM
    • 2 Beds
    • 1.5 Baths
    • 1,784 Sq Ft

    62 Winter St, Stratford, CT 06614

    Welcome to this charming 2-bedroom, 1.5-bath Colonial offering approximately 1,784 square feet of living space and a spacious lot. The classic two-story layout provides comfortable living areas and timeless Colonial character, while the full basement offers valuable additional space for storage, hobbies, a workshop, or future possibilities. A fireplace adds warmth and character to the home, while

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    Eric Bergers

    William Raveis Real Estate

    62 Winter St, Stratford, CT 06614
  • /38

    $399,900

    • 3 Beds
    • 1.5 Baths
    • 1,634 Sq Ft

    64 Glendale Ave, Bridgeport, CT 06606

    A Rare North End Treasure, Ready for Its Next Chapter. Available for the first time ever, this cherished North End Colonial presents a rare opportunity to own a home rich in history and potential. Solidly built and lovingly maintained through generations, the home features a remodeled kitchen, newer windows, updated mechanicals, and hardwood floors in the living and dining rooms. Upstairs offers

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    Victoria Stillings

    Coldwell Banker Realty

    64 Glendale Ave, Bridgeport, CT 06606
  • /37

    $725,000

    $50K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,524 Sq Ft

    241 Old Stratfield Rd, Fairfield, CT 06825

    !!!ASSUMABLE 3% VA LOAN - APPROX. $468,000 BALANCE!!! A rare opportunity to secure a substantial portion of your financing at just 3% on this fully renovated Fairfield two-family! Current rents total $4,650/month and are believed to be below market, creating a compelling opportunity for owner-occupants and investors alike. Live in one unit and let the other help offset your housing costs or add a

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    Andrei Balaj

    Higgins Group Real Estate

    241 Old Stratfield Rd, Fairfield, CT 06825
  • /27

    $524,900

    Open Sun 2PM - 4PM
    • 4 Beds
    • 1.5 Baths
    • 2,140 Sq Ft

    26 Powell Terrace, Bridgeport, CT 06604

    Welcome to 26 Powell Terrace! This spacious 4-bedroom, 1.5-bath home offers a comfortable layout with plenty of room to spread out. The main-level primary bedroom provides added convenience, while the generously sized living room creates an inviting space for relaxing, entertaining, and everyday living. The 1.5 baths include a convenient shower in the half bath. Downstairs, the full basement

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    Kostas Travisano

    Sailpoint Property Group

    26 Powell Terrace, Bridgeport, CT 06604
  • /40

    $1,049,900

    Open Sun 1PM - 3PM
    • 4 Beds
    • 4 Baths
    • 3,828 Sq Ft

    24 Plum Tree Ln, Trumbull, CT 06611

    Set on a beautifully private, level 1.01-acre lot on the Fairfield/Easton line, this custom-built 2007 Colonial offers an exceptional combination of space, style, flexibility, and location. With 4 bedrooms, 4 full baths, a 3-car garage, public water and sewer, and a fabulous level backyard with excellent pool potential, this is the Fairfield County gem you have been hoping to find! A dramatic

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    Fredda Takacs

    Higgins Group Real Estate

    24 Plum Tree Ln, Trumbull, CT 06611
  • /38

    $485,000

    $40K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    292 Naugatuck Ave, Milford, CT 06460

    Step out of the ordinary and into this amazing Mediterranean-style Ranch, featuring a bright, sunny open floor plan with gleaming hardwood floors and a cozy fireplace. The remodeled eat-in kitchen offers granite counters, stainless steel appliances including a top of the line, Wolf gas stove and Thermador dishwasher, the sliders lead to a covered backyard patio-perfect for relaxing or

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    Pam Famiglietti

    William Raveis Real Estate

    292 Naugatuck Ave, Milford, CT 06460
  • /35

    $329,900

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

    3250 Fairfield Ave Unit 110, Bridgeport, CT 06605

    Cash Sale Only: Easy living in the heart of Black Rock! Tucked into a desirable rear corner of the Village at Black Rock, this 2-bedroom, 2-full-bath condo offers approximately 1,145 square feet of comfortable one-level living with peaceful views overlooking Ash Creek. Step inside and you'll immediately appreciate the bright, open layout where the kitchen, dining, and living spaces come

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    Alan Stewart Jr.

    ASJ Realty Partners

    3250 Fairfield Ave Unit 110, Bridgeport, CT 06605
  • /40

    $499,900

    $30K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,562 Sq Ft

    2 Chatham Terrace, Bridgeport, CT 06606

    Rarely does an opportunity come along to live on one of the North End's most desirable cul-de-sacs just off beautiful Lake Forest-a place where neighbors move in and never want to leave. With peaceful water views overlooking the Lake Forest Association park, this well-maintained home offers the perfect blend of comfort, lifestyle, and location. The optional association provides access to a

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    Alan Stewart Jr.

    ASJ Realty Partners

    2 Chatham Terrace, Bridgeport, CT 06606
  • /36

    $649,000

    • 2 Beds
    • 2.5 Baths
    • 1,731 Sq Ft

    80 Bywater Ln, Bridgeport, CT 06605

    ACT FAST UNIT 54 JUST CLOSED FOR $825K, THIS IS THE BEST VALUE IN BLACK ROCK - Welcome Home to 80 Bywater Lane. Move right into this Voguish, NY chic styled, completely updated townhouse offering 3 spacious levels of comfortable living. Nestled in & surrounded by both nature & seasonal water views. This peaceful home offers total serenity while lounging on 1 of your 3 decks. Featuring 6 generous

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    Jackie Davis

    William Raveis Real Estate

    80 Bywater Ln, Bridgeport, CT 06605
  • /39

    $680,000

    • 3 Beds
    • 3 Baths
    • 1,146 Sq Ft

    126 Roberton Crossing Unit 126, Fairfield, CT 06825

    Welcome to effortless living at sought-after Woodfield Village! This beautifully renovated 2-bedroom, 3-full-bath second-floor ranch offers the ease of single-level living in a desirable setting with peaceful wooded views. Hardwood floors and vaulted ceilings enhance the bright, open main living area, where the Living Room and Dining Room flow seamlessly together. The updated Kitchen offers

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    Susan Lieberman

    The Riverside Realty Group

    126 Roberton Crossing Unit 126, Fairfield, CT 06825
  • /25

    $299,000

    • 3 Beds
    • 1 Bath
    • 1,001 Sq Ft

    332 Palisade Ave, Bridgeport, CT 06610

    Opportunity Alert at 332 Palisade! ... If you've been waiting for a home you can truly make your own, THIS is the one. Bring your ideas, bring your style - this place is ready for a full glow-up! Inside, you'll find three bedrooms (one on the main level and two upstairs), plus a full bathroom and laundry hookups conveniently located on the main floor. There's a very large living room and a bright

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    Lisa Nussbaum

    Top Tier Realty Group, LLC

    332 Palisade Ave, Bridgeport, CT 06610
  • /19

    $1,575,000

    $124K PRICE DROP
    • 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

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    Glenn Marr

    Marr Caruso Realty Group

    173 Puritan Rd, Fairfield, CT 06824
  • /20

    $249,900

    Coming Soon
    • 2 Beds
    • 1 Bath
    • 984 Sq Ft

    520 Vincellette St Unit C1, Bridgeport, CT 06606

    Tucked away in Bridgeport's desirable North End, this beautifully maintained end-unit condo at 520 Vincellette St offers rare privacy, sunlight, and style. As you arrive, you're greeted by a quiet, tree-lined complex with plenty of parking and a welcoming community feel. Being an end unit means fewer shared walls and more natural light-plus added peace and quiet. Inside, you'll immediately notice

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    Alan Stewart Jr.

    ASJ Realty Partners

    520 Vincellette St Unit C1, Bridgeport, CT 06606
  • /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.

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    David Krasnoff

    Compass Connecticut, LLC

    37 Bartram Ave, Bridgeport, CT 06605
  • /9

    $235,000

    • 1 Bed
    • 1 Bath
    • 707 Sq Ft

    115 Short Beach Rd Unit 104, Stratford, CT 06615

    Welcome to 115 Short Beach Road #104, a beautifully maintained 1-bedroom, 1-bath condominium offering comfortable, low-maintenance living in a convenient Stratford location. This bright and inviting unit features a spacious open layout, generous natural light, and a well-appointed kitchen that flows seamlessly into the living and dining areas, creating an ideal space for both everyday living and

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    Javyn Roundtree

    Roundtree Realty LLC

    115 Short Beach Rd Unit 104, Stratford, CT 06615
  • /28

    $435,000

    • 3 Beds
    • 1.5 Baths
    • 1,106 Sq Ft

    146 Wood Ave, Stratford, CT 06614

    3-bedroom, 1.5-bath Colonial featuring original 1930s wood finishes, beautiful arched doorways, and 9-foot ceilings that give the home an airy, spacious feel. Enter through the welcoming sunroom and sip your morning coffee as the breeze comes in through the adjustable glass panel walls. Natural light streams into the window-lined, open-concept sitting room and adjacent living room with a tiled,

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    Todd Auslander

    Keller Williams Prestige Prop.

    146 Wood Ave, Stratford, CT 06614
  • /3

    $799,000

    $51K PRICE DROP
    • 8 Beds
    • 5.5 Baths
    • 2,400 Sq Ft

    Unlisted Address

    Fantastic Investment Property for Sale in Bridgeport!Located at 156 Columbia Street, this versatile investment property is a prime opportunity in a growing area. With easy access to major roadways, this site benefits from strong visibility and traffic flow. The property features spacious interiors suitable for various business types, including retail, offices, or service-oriented establishments.

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    Alexander Galvez

    Century 21 Galvez

    Unlisted Address
  • /30

    $95,000

    • 2 Beds
    • 1 Bath
    • 622 Sq Ft

    317 Court D B-46 Ct Unit 317, Bridgeport, CT 06610

    Beautifully updated from top to bottom, this townhouse-style cooperative offers an affordable opportunity for homeownership. The bright and inviting interior has been thoughtfully renovated throughout and is move-in ready. Outside, enjoy your own fenced front and rear yard areas featuring garden space, a patio for outdoor entertaining, and a storage shed. Off-street parking adds to the home's

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    Sue Varrone

    Coldwell Banker Realty

    317 Court D B-46 Ct Unit 317, Bridgeport, CT 06610
  • /2

    $475,000

    • 3 Beds
    • 1.5 Baths
    • 1,967 Sq Ft

    866 Merritt St, Bridgeport, CT 06606

    Welcome to this spacious 3-bedroom, 1.5-bath Colonial offering nearly 2,000 square feet of living space and plenty of opportunity to make it your own. The main level features a comfortable living room highlighted by a fireplace, a generously sized kitchen with ample cabinetry, and a dedicated dining area. Upstairs, you'll find three well-proportioned bedrooms and a full bath. A full basement and

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    Eric Bergers

    William Raveis Real Estate

    866 Merritt St, Bridgeport, CT 06606
  • /36

    $695,000

    • 2 Beds
    • 2.5 Baths
    • 1,858 Sq Ft

    170 Glengarry Rd, Fairfield, CT 06825

    Fairfield's sought-after Woodfield Village community, 170 Glengarry Road is an exceptional corner end-unit offering space, natural light, and effortless living. At 1,858 square feet-the largest unit in the complex-this beautifully maintained home features two bedrooms, two full and one half baths, a versatile den which is unique to the units, and the rare convenience of a two-car attached garage.

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    Amy Waugh Curry ABR CRS GRI

    Berkshire Hathaway NE Prop.

    170 Glengarry Rd, Fairfield, CT 06825
  • /2

    $950,000

    • 18 Beds
    • 4 Baths
    • 4,744 Sq Ft

    1014 Noble Ave, Bridgeport, CT 06608

    Incredible income-generating opportunity with this 18-room legal rooming house, fully compliant and positioned for maximum return. Projected annual income at full capacity $189,000. One room occupied rent-free by on-site property manager. Ideal for investors seeking steady cash flow and minimal vacancies features 16 private rooms 2 efficiency units and 2 shared bathrooms. Average room size: 14' x

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    Latasha Eaddy

    Eaddy Associates

    1014 Noble Ave, Bridgeport, CT 06608
  • /32

    $474,900

    Open Sat 1PM - 3PM
    • 3 Beds
    • 1.5 Baths
    • 1,578 Sq Ft

    704 W Taft Ave, Bridgeport, CT 06604

    Welcome to this inviting 3-bedroom, 1.5-bath Colonial located in Bridgeport's desirable Brooklawn area! Offering plenty of space inside and out, this home features a comfortable traditional layout along with a finished lower level providing additional living, recreation or flex space. With potential for future expansion and customization, there's plenty of opportunity to make this home your own.

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    Khaliq Brown

    CLMA Realty

    704 W Taft Ave, Bridgeport, CT 06604
  • /2

    $2,299,000

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

    446 Wormwood Rd, Fairfield, CT 06824

    Exceptional New Construction in the University Area. Nestled on a quiet, low-traffic street in the heart of the desirable university neighborhood, this stunning new construction home perfectly blends luxury craftsmanship, modern functionality, and unmatched convenience. Currently under construction with a planned completion for May, this property offers a rare window of opportunity for buyers to

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    Bette Gigliotti

    William Raveis Real Estate

    446 Wormwood Rd, Fairfield, CT 06824
  • /32

    $439,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    41 Quince St, Bridgeport, CT 06606

    Updated and move-in ready, this well-maintained home offers a refreshed kitchen, fresh interior paint, and a versatile floor plan. The finished lower level includes an additional bedroom, second kitchen, full bath, and separate living space, providing excellent flexibility for extended household living or a potential in-law setup (buyer to perform their own due diligence regarding permitted use).

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    Rudy Pierre

    YellowBrick Real Estate LLC

    41 Quince St, Bridgeport, CT 06606
  • /2

    $675,000

    • 4 Beds
    • 2 Baths
    • 3,211 Sq Ft

    32-34 Autumn St, Bridgeport, CT 06608

    Great for owner occupied. Both floors have been rehab. Close to shopping centers, restaurants, public transportation, parks. A must see

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    Matthew Langston

    Rising Legacy Realty

    32-34 Autumn St, Bridgeport, CT 06608
  • /7

    $599,900

    • Land
    • 11,325 Sq Ft
    • $2,307,308 per Acre

    2152 Barnum Ave, Stratford, CT 06615

    Exceptional development opportunity in Stratford. This fully approved site for 34 residential units is designed with covered parking, lobby access, and a layout tailored for today's renters seeking convenience and accessibility. Located near Interstate 95, public transportation, and the Metro-North Railroad, this location offers easy commuting throughout Fairfield County and into New York City.

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    Alan Stewart Jr.

    ASJ Realty Partners

    2152 Barnum Ave, Stratford, CT 06615
  • /5

    $649,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,826 Sq Ft

    460 Stonybrook Rd Unit 1, Stratford, CT 06614

    Welcome to 460 Stony Brook Road, Stratford, CT, where modern living meets the convenience of brand-new construction. These townhouse-style single-family homes offer the privacy of homeownership. Situated on a level lot, you'll appreciate the welcoming curb appeal, a sleek look of light siding and black trim compliments thew private setting, and attached two-car garage-no more clearing snow off

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    Alan Stewart Jr.

    ASJ Realty Partners

    460 Stonybrook Rd Unit 1, Stratford, CT 06614
  • /35

    $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
  • /37

    $2,399,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,950 Sq Ft

    96 Clinton St, Fairfield, CT 06824

    One of only two new construction homes currently available in Fairfield's coveted Beach neighborhood, an incredible opportunity w/ outstanding market value & just steps to the beach - Welcome Home to 96 Clinton Street. 4 levels of living w/ 2950 sf, elevator shaft ready, 4 bedrooms, 3.5 bath & high end finishes throughout. The open concept main level features custom finishes w/ a chef's kitchen

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    Jackie Davis

    William Raveis Real Estate

    96 Clinton St, Fairfield, CT 06824
  • /29

    $599,000

    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft

    110 Minturn Rd, Bridgeport, CT 06606

    Welcome to 110 Minturn Road, a beautifully updated 3-bedroom, 2-bath home ideally situated on a desirable corner lot along the Trumbull/Fairfield border. Move-in ready and thoughtfully renovated, this home features a brand-new kitchen and updated bathrooms, with gorgeous hardwood floors flowing throughout. Enjoy year-round comfort with central heat and air conditioning. The finished lower level

    Alexia Andrade US Asset Realty

    110 Minturn Rd, Bridgeport, CT 06606
  • /27

    $899,900

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,898 Sq Ft

    39 Wildemere Ave, Milford, CT 06460

    Just five homes from the shoreline, this is the kind of beach living that feels effortless year-round! Perfectly positioned in Wildermere Beach, this sun-filled colonial beautifully blends coastal charm with everyday comfort, moments from the sand and all that Milford has to offer. Natural light pours through the open-concept layout, highlighting the designer kitchen, dining area, and living

    Amber Blake Stacy Blake Realty LLC

    39 Wildemere Ave, Milford, CT 06460
  • /32

    $549,000

    • 2 Beds
    • 2 Baths
    • 1,430 Sq Ft

    193 Wilson St, Bridgeport, CT 06605

    Amazing opportunity to own this cute-as-a-button 2-family home in the center of Black Rock! Both 1-bedroom apartments have been thoroughly updated over the years, including kitchen and bath cabinets and countertops, plumbing fixtures, appliances, flooring, recessed lighting, HVAC systems, and landscaping/stonework. The property also includes a private driveway with large gravel area in the rear

    Kaitlyn Walsh William Raveis Real Estate

    193 Wilson St, Bridgeport, CT 06605
  • /31

    $890,000

    • 10 Beds
    • 5 Baths
    • 3,530 Sq Ft

    80-82 Poplar St, Bridgeport, CT 06605

    Exceptional investment opportunity in Bridgeport's desirable Black Rock neighborhood! This well-maintained three-family property offers strong cash flow with a current gross monthly rental income of $8,600, making it an excellent addition to any investor's portfolio or an ideal owner-occupied opportunity. The first and second floor units each feature 3 bedrooms and 1 full bathroom, while the

    Alexia Andrade US Asset Realty

    80-82 Poplar St, Bridgeport, CT 06605
  • /35

    $719,000

    • 5 Beds
    • 3 Baths
    • 3,234 Sq Ft

    244 Bennett St Unit 246, Bridgeport, CT 06605

    Black Rock living at its finest! This pristine 2-family property offers three finished levels that have been thoroughly updated over the years including flooring, kitchen cabinetry, countertops, appliances, bathroom vanities and plumbing fixtures, recessed lighting, sheetrock, trim, HVAC, electrical, and more. Enjoy low maintenance landscaping with crushed stone and mature perennial and evergreen

    Kaitlyn Walsh William Raveis Real Estate

    244 Bennett St Unit 246, Bridgeport, CT 06605
  • /40

    $1,399,000

    • 4 Beds
    • 4 Baths
    • 4,290 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
  • /38

    $3,695,000

    • 4 Beds
    • 4.5 Baths
    • 3,744 Sq Ft

    110 Judson Rd, Fairfield, CT 06824

    Nestled on one of Fairfield Beach's most coveted streets, this exceptional new construction blends timeless coastal architecture with sophisticated design in a location that's simply hard to duplicate. Just moments from the beach, town, train, schools, and parks, 110 Judson offers the rare convenience today's buyers seek without sacrificing privacy or tranquility. Thoughtfully positioned at a

    Cindy Raney Coldwell Banker Realty

    110 Judson Rd, Fairfield, CT 06824

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