Homes for Sale near Fairfield Country Day School

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  /15

  $460,000

  • 2 Beds
  • 1.5 Baths
  • 1,852 Sq Ft

  86 Vanguard St, Bridgeport, CT 06606

  This recently renovated house is currently rented through May 31, 2026. On an oversized lot of more than 1/3 acre there is plenty to enjoy open space. If financing, please include an appraisal gap clause.

  Robert Rosenfeld Keller Williams Prestige Prop.

  86 Vanguard St, Bridgeport, CT 06606
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  /21

  $174,900

  • 1 Bed
  • 1 Bath
  • 604 Sq Ft

  2370 North Ave Unit 4C, Bridgeport, CT 06604

  Spacious, bright one-bedroom condo at The Regency, located in Bridgeport's desirable Brooklawn/St. Vincent's district. This well-maintained high-rise, with 24-hour doorman service, secure lobby and on-site laundry, offers modern urban living in a historic setting. Inside, find an open layout with abundant natural light, full-size bedroom with large closet, and generous living/dining area. The

  Sandy Chang Century 21 Scala Group

  2370 North Ave Unit 4C, Bridgeport, CT 06604
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  /28

  $799,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,655 Sq Ft

  14 Windsor Place, Fairfield, CT 06824

  Home sweet home! This beautifully updated split-level sits on a quiet street in the sought-after University area. The spacious, open layout welcomes you into the living room, featuring hardwood floors and a wood-burning fireplace. The updated kitchen includes hardwood floors, custom cabinetry, granite countertops, recessed lighting, and stainless-steel appliances, and it adjoins the dining area -

  Sara Fowler Coldwell Banker Realty

  14 Windsor Place, Fairfield, CT 06824
• 

  

  

  /13

  $390,500

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  122 Indian Field Rd, Bridgeport, CT 06606

  Charming 3-Bedroom North End Home - Move-In Ready or perfect investment property! Welcome to this nicely updated 3-bedroom, 1-bathroom home offering convenient one-level living in a highly desirable North End neighborhood. Located within walking distance to parks, shops and John Winthrop school. Just 1.5 miles from Sacred Heart, this home combines location, comfort, and functionality. Step inside

  Amy Thomas Houlihan Lawrence

  122 Indian Field Rd, Bridgeport, CT 06606
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  /11

  $260,000

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  2625 Park Ave Unit 14N, Bridgeport, CT 06604

  Best panoramic views of the city from this corner unit! See the LI Sound from this 14th floor Embassy Towers condominium with balcony. Unit is offering 2 BR, 2 baths, and lots of closet space. Major renovations just completed including new paint throughout the unit, new kitchen fully equipped with new appliances. Spacious Primary bedroom with attached bath and large closets. Huge Living Room with

  Aziz Seyal William Raveis Real Estate

  2625 Park Ave Unit 14N, Bridgeport, CT 06604
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  /39

  $625,000 Open Thu 4PM - 6PM

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft

  125 Vesper St, Fairfield, CT 06825

  Nestled on a charming tree-lined street, this sun-filled 3-bedroom Colonial offers a perfect blend of character, space, and location. Sitting proudly on a corner lot in a quiet, walkable neighborhood, the home features hardwood floors, high ceilings, and an easy flowing layout ideal for everyday living and entertaining. The spacious eat-in kitchen boasts solid wood cabinetry, a gas stove, cozy

  Max Dober Keller Williams Prestige Prop.

  125 Vesper St, Fairfield, CT 06825
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  /9

  $795,000

  • 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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  /40

  $1,050,000 Open Sat 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,552 Sq Ft

  98 Cambridge St, Fairfield, CT 06824

  Picture Perfect Expanded Cape on quiet side street in Fairfield's Beach & Marina Neighborhood! Enjoy life and living with access to coveted beach with boating, bonfires, and clambakes or walk to train and downtown with award winning restaurants and shopping! Many new upgrades and expansion to make this home all ready to move in! Gorgeous Kitchen with huge Island with seating. New Trex Deck via

  Terry Keegan Fairfield County Real Estate

  98 Cambridge St, Fairfield, CT 06824
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  /20

  $229,900

  • 1 Bed
  • 1 Bath
  • 825 Sq Ft

  2625 Park Ave Unit 15G, Bridgeport, CT 06604

  Welcome to this beautifully one-bedroom, one-bath condo. Situated in a 24 hour full-service high-rise building. Combines modern comfort with unbeatable convenience. The unit features an open-concept layout filling the space with natural light.

  Jacquelyn Santini Ardent Trust Property Mngmnt

  2625 Park Ave Unit 15G, Bridgeport, CT 06604
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  /40

  $580,000 Open Sat 1PM - 4PM

  • 3 Beds
  • 3 Baths
  • 2,764 Sq Ft

  520 Savoy St, Bridgeport, CT 06606

  Step inside this captivating home in A1 Zone in North End where classic tradition meets modern convenience. A solidly built 1932 Colonial is thoughtfully remodeled and updated for contemporary living. Enjoy abundant natural light throughout, creating a bright and airy ambiance perfect for entertaining and everyday life. The heart of the home, the kitchen, is fully equipped with all new

  Daniel Williams William Raveis Real Estate

  520 Savoy St, Bridgeport, CT 06606
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  /28

  $800,000

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

  38 Pepperbush Ln, Fairfield, CT 06824

  Wonderful University center hall colonial conveniently located to everything. This well cared for home includes a formal living room and dining room, updated eat-in-kitchen with granite counters and st / st appliances and a bright and spacious family room with a terrific fireplace. The second floor includes a primary bedroom with a bath and walk-in closet, a hall bath and 3 additional bedrooms.

  John Shea William Raveis Real Estate

  38 Pepperbush Ln, Fairfield, CT 06824
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  /38

  $3,375,000

  • 5 Beds
  • 6 Baths
  • 4,668 Sq Ft

  91 Turkey Hill Rd S, Westport, CT 06880

  Welcome to a home that lives as beautifully as it looks. In the heart of Greens Farms, this timeless 5 bedroom, 6 bath Colonial is where classic elegance meets modern ease, designed for how you live, work, and entertain today. A circular drive, stone walls, and a charming front porch create an inviting first impression. Inside, a sun-filled double-height entry sets the tone for open, gracious

  Chrissie Rodriguez Higgins Group Real Estate

  91 Turkey Hill Rd S, Westport, CT 06880
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  /17

  $649,900

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  142 Doreen Dr, Fairfield, CT 06824

  Charming 3-bedroom, 1-bath Ranch nestled on a private lot surrounded by mature privacy hedges in a phenomenal Fairfield neighborhood. Hardwood floors lie beneath all carpeting (excluding kitchen and porch), offering excellent potential for easy updates. The spacious 3-season porch provides opportunity for year-round use with a simple conversion. The finished lower level adds 480 sq ft of living

  Frank D'Ostilio Houlihan Lawrence WD

  142 Doreen Dr, Fairfield, CT 06824
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  /13

  $220,000

  • 1 Bed
  • 1 Bath
  • 1,046 Sq Ft

  48 Riverview Dr Unit 48, Bridgeport, CT 06606

  Welcome to 48 Riverview Drive! Pristine, light-filled, first-floor end-unit condo! Updated kitchen with granite countertops and stainless steel appliances. Spacious open floor plan with dark laminate flooring throughout. Living room is both comfortable and functional with sliders leading out to private sunny deck. Perfect spot to enjoy morning coffee or afternoon sun. The Primary bedroom is large

  Christine Howard William Raveis Real Estate

  48 Riverview Dr Unit 48, Bridgeport, CT 06606
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  /38

  $540,000

  • 3 Beds
  • 1.5 Baths
  • 1,553 Sq Ft

  311 Westfield Ave, Bridgeport, CT 06606

  WELCOME TO WESTFIELD AVENUE! This lovely colonial located in the desirable North End of Bridgeport has been totally remodeled, including the kitchen with brand new cabinets, new quartz counter tops, new tiled back splash, new engineered hardwood floor and all new stainless-steel appliances. Newly updated half bath on the first floor and newly updated full bath on the second floor with tiled floor

  Steven Lage Coldwell Banker Realty

  311 Westfield Ave, Bridgeport, CT 06606
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  /27

  $520,000

  • 4 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  301 Weeping Willow Ln, Fairfield, CT 06825

  Welcome to 301 Weeping Willow, a rare opportunity in a prime Fairfield location tucked away on a peaceful cul-de-sac. Whether you're an investor searching for a high-demand Sacred Heart University rental, a flipper ready for your next project, or a buyer looking to create your dream home, this property is filled with potential. This 4-bedroom, 2.5-bath home offers 1,300 square feet of finished

  Matthew Hyde William Raveis Real Estate

  301 Weeping Willow Ln, Fairfield, CT 06825
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  /20

  $599,000

  • 4 Beds
  • 1 Bath
  • 1,446 Sq Ft

  261 Colony St, Fairfield, CT 06824

  Welcome to 261 Colony Street. Ideally located for convenient Fairfield living, this home offers a flexible layout and room to grow. The main level features two bedrooms and a full bath, along with an updated, eat-in kitchen that flows into the dining area and living room. The screened-in porch-perfect for morning coffee or quiet evenings. Upstairs, you'll find two spacious bedroom and there's

  Christine Howard William Raveis Real Estate

  261 Colony St, Fairfield, CT 06824
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  /31

  $775,000 Open Thu 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 2,200 Sq Ft

  363 Lake Ave, Bridgeport, CT 06605

  Welcome to 363 Lake Avenue, where classic charm meets modern updates in the heart of Black Rock's sought-after St. Mary's by the Sea community. This sun-drenched 3-bedroom, 1.5-bath Colonial offers a blend of timeless detail and contemporary comfort-just steps from scenic waterfront paths, kayaking, biking, and the vibrant local dining scene. Beautifully maintained, this home features original

  Geo Crume Keller Williams Prestige Prop.

  363 Lake Ave, Bridgeport, CT 06605
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  /40

  $2,399,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3 Baths
  • 3,157 Sq Ft

  260 Birch Rd, Fairfield, CT 06824

  Experience Coastal Luxury in this Brand New Custom Colonial just steps away from the soothing sands & sea breeze of Penfield Beach, featuring a brand-new pavilion for the ultimate Gold Coast lifestyle! Perfectly situated on one of Fairfield's most coveted streets, this FEMA-compliant custom home offers 4 Bedrooms, 3 Full bathrooms & over 3,000 square feet of thoughtfully designed living space

  Melissa Montagno Higgins Group Real Estate

  260 Birch Rd, Fairfield, CT 06824
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  /39

  $699,000 Open Thu 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,533 Sq Ft

  114 Castle Ave, Fairfield, CT 06825

  A beautiful, COMPLETELY REMODELED in 2025 Colonial awaits - welcome home to 114 Castle Avenue. Offering four spacious bedrooms two of which are on the first floor (a rare find) and two full bathrooms, one on the first level and one on the second - blending modern updates with easy living. The stunning all new eat-in kitchen, featuring a large center island, sleek quartz countertops, brand new

  Lisa Mancini William Raveis Real Estate

  114 Castle Ave, Fairfield, CT 06825
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  /28

  $525,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  132 Toll House Ln, Fairfield, CT 06825

  Cute as a button. This adorable ranch has all the charm you can imagine. Living room with hardwood floors. Spacious kitchen with breakfast bar and room for a table with a back door to the cozy screened in porch. There are 3 bedrooms and a bath. The lower level has a large basement with high ceilings and would be great space to finish. The level yard is nicely landscaped. The roof was replaced in

  Elaine Parruccini William Raveis Real Estate

  132 Toll House Ln, Fairfield, CT 06825
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  /40

  $499,900

  • 3 Beds
  • 2 Baths
  • 2,480 Sq Ft

  547 Anton St, Bridgeport, CT 06606

  Sacred Heart Investors Alert!!! This house lives like a 2 family with a Living Room, Eat In Kitchen, Dining Room, 2 Bedrooms and a remodeled bath on the main level....2 Bedrooms with a huge eat in kitchen and laundry on the 2nd floor with 2 separate entrances....and a lower level with a laundry, 2 bedrooms, mechanical room and bilco doors. Plus there is a 2 car garage, a yard that is just the

  Karin Stocknoff Century 21 AllPoints Realty

  547 Anton St, Bridgeport, CT 06606
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  /34

  $1,299,000

  • 3 Beds
  • 2.5 Baths
  • 2,449 Sq Ft

  6 Janson Dr, Westport, CT 06880

  PRESENT OFFERS BY NOON MONDAY, 8/4. Nestled on a quiet cul-de-sac just minutes from town, this well-maintained contemporary colonial offers the perfect blend of comfort, style and convenience. Set on a beautifully landscaped half-acre lot with mature plantings, this house has privacy while remaining close to shopping, restaurants, commuter routes and local amenities including town tennis courts

  Tamarra Pincavage William Pitt Sotheby's Int'l

  6 Janson Dr, Westport, CT 06880
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  /14

  $399,999

  • 3 Beds
  • 2 Baths
  • 1,060 Sq Ft

  Unlisted Address

  EXPANSIVE BACKYARD - PERFECT FOR CONTRACTORS, LANDSCAPERS, OR EXTRA PARKING! Located in the highly desirable Brooklawn neighborhood, this charming home beautifully blends classic character with modern comfort. The spacious backyard offers endless potential, ideal for storing equipment, parking multiple vehicles, or enjoying the outdoors.

  Andrew Cevasco Las Americas Real Estate

  Unlisted Address
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  /34

  $799,999

  • Land
  • 16 Acres
  • $50,955 per Acre

  90 Redding Rd, Easton, CT 06612

  Parklike, serene, rural, 15.7 acres of open land, mostly cleared and adjacent to the Aspetuck Country Club Golf Course. The Aspetuck River is between the property and the country club. Owner has cleared most of the acreage and built beautiful stone walls. There is the possibility of additional land being included in the purchase. This land is in a 100 year flood zone, and the setback from the

  Charlotte Cotton William Raveis Real Estate

  90 Redding Rd, Easton, CT 06612
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  /24

  $3,500,000

  • 5 Beds
  • 3 Baths
  • 4,170 Sq Ft

  70 Redding Rd, Easton, CT 06612

  This magnificent country estate includes the historic Thorp House on 24.5 acres of riverfront property, as well as a charming 1 bedroom rental cottage with attached 2 car garage. The main house, built in 1750, is listed on the National Register of Historic Places. Authentic period details grace the home with unique old world charm. Cathedral ceilings in the kitchen and great room make a stately

  Charlotte Cotton William Raveis Real Estate

  70 Redding Rd, Easton, CT 06612
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  /31

  $394,500

  • 3 Beds
  • 1 Bath
  • 1,320 Sq Ft

  669 Clark St, Bridgeport, CT 06606

  Location! Great opportunity in quiet North End neighborhood. Charming curb appeal. Lovingly maintained by original owner for 70 years! Spacious foyer with center hall staircase. Open floorplan formal dining room and living room featuring wood burning fireplace clad in stone. Nicely appointed eat in kitchen offers tons of cabinets and steps out to quaint sun porch overlooking manicured level yard

  Patricia Walker Coldwell Banker Realty

  669 Clark St, Bridgeport, CT 06606
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  /40

  $435,000

  • 3 Beds
  • 2.5 Baths
  • 1,438 Sq Ft

  385 Burnsford Ave, Bridgeport, CT 06606

  Approximately 1500 square feet of thoughtfully designed living space await in this well-appointed house. The three bedroom, two and a half bathroom floor plan offers versatile accommodations and ample room to comfortable suit a variety of living needs. The primary bedroom features an abundance of natural light. Two additional bedrooms provide comfortable secondary sleeping quarters. The two and a

  Robert Richter Coldwell Banker Realty

  385 Burnsford Ave, Bridgeport, CT 06606
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  /5

  $1,300,000

  • Land
  • 2.65 Acres
  • $490,566 per Acre

  22 Brett Rd, Fairfield, CT 06824

  An exceptional opportunity to build your dream home on one of the most desirable and scenic settings in Fairfield. This beautiful, flat 2.65-acre parcel-approved by the Wetlands Commission for a 5-bedroom, 5-bathroom residence with a pool and pool house-offers both privacy and prestige. The property is situated in the estate section of Greenfield Hill, directly across Congress Street from one of

  Andrew Whiteley Brown Harris Stevens

  22 Brett Rd, Fairfield, CT 06824
• 

  

  /19

  $899,000

  • 9 Beds
  • 6 Baths
  • 5,740 Sq Ft

  1659 Fairfield Ave, Bridge Port, CT 06605

  Prime Mixed-Use Investment Opportunity! This well-maintained building features 4 residential apartments and 2 ground-level storefronts, all in a high-visibility, high-traffic location right across from Starbucks, just minutes from the beach, and with immediate access to the highway. With many recent updates throughout the property, it offers strong income and even greater potential-current rents

  Karim Douich William Raveis Real Estate

  1659 Fairfield Ave, Bridge Port, CT 06605
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  /10

  $189,900

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  252 Harlem Ave Unit B6, Bridgeport, CT 06606

  Welcome to this spacious and sun-filled one-bedroom, one-bath unit located in the desirable North End of Bridgeport. Nestled in a quiet, residential neighborhood, this top-floor unit offers peaceful living with no one above you and the convenience of secured underground parking. Step inside to discover a bright and airy open-concept living and dining room that flows seamlessly onto a private

  Tasha Woodford IPSG Real Estate LLC

  252 Harlem Ave Unit B6, Bridgeport, CT 06606
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  /39

  $499,823

  • 4 Beds
  • 2 Baths
  • 1,381 Sq Ft

  88 Plankton St, Bridgeport, CT 06606

  "Classic Cape in Desirable North End Neighborhood!" Looking for classic charm in a great location? This sweet Cape-Cod checks all the boxes. Set on a fully fenced corner lot, this 4 bedroom, 2 bath home features a number of recent touch-ups & updates. The entry opens to a cozy living room, where a wood-burning fireplace sets the tone for relaxing nights in, and a large picture window brings in

  Cindy Cox William Raveis Real Estate

  88 Plankton St, Bridgeport, CT 06606
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  /3

  $475,000

  • 4 Beds
  • 3 Baths
  • 1,507 Sq Ft

  200 Stratfield Place, Bridgeport, CT 06606

  200 Stratfield Place has undergone a remarkable transformation over the past two years, elevating this North End property to a whole new level. Major upgrades include: *all three bathrooms fully renovated, brand-new windows throughout, full exterior repaint, repaved foundation, relined chimney, new heating zones on the boiler, and a 50-gallon hot water heater.* Inside, enjoy four spacious

  Ralph Lewis Coldwell Banker Realty

  200 Stratfield Place, Bridgeport, CT 06606
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  /37

  $1,050,000

  • 3 Beds
  • 2 Baths
  • 2,388 Sq Ft

  7 Ambler Rd W, Westport, CT 06880

  Nestled on a peaceful private cul-de-sac in the heart of Westport, this delightful 3-bedroom, 2-bath home combines comfort, charm, and thoughtful updates! Step inside to find a sun-filled layout with a welcoming flow, perfect for both everyday living and entertaining. The updated kitchen is a highlight, offering modern style and functionality with easy access to the dining and living areas.

  Linda Skolnick Coldwell Banker Realty

  7 Ambler Rd W, Westport, CT 06880
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  /29

  $599,000

  • 2 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  48 Bywater Ln Unit 48, Bridgeport, CT 06605

  Rare opportunity to own an exquisite townhouse in the Historic Black Rock. Completely interior has been freshly painted. One of the most coveted condominium complexes Bywatyr Town Homes, a small complex o 24 units located on the cut-de-sac across from Fayerweather Yacht Club and Black Rock Harbor. This unit was the original model unit with many upgrades throughout. Year round water views from all

  Cristy Schnauffer Coldwell Banker Realty

  48 Bywater Ln Unit 48, Bridgeport, CT 06605
• 

  

  /22

  $849,000

  • 4 Beds
  • 1.5 Baths
  • 2,107 Sq Ft

  107 Rockland Rd, Fairfield, CT 06825

  Welcome to this beautifully updated 4 bedroom home nestled in the heart of Fairfield's coveted Stratfield neighborhood. Perfectly blending classic charm with modern updates, this residence offers a chef's kitchen complete with Sub-Zero, Wolf, and Bosch appliances, custom cabinetry, and abundant counter space, ideal for entertaining or everyday living. The bright and spacious floor plan includes a

  Eric Sundman Higgins Group Real Estate

  107 Rockland Rd, Fairfield, CT 06825
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  /10

  $1,000,000

  • 4 Beds
  • 2.5 Baths
  • 2,644 Sq Ft

  647 Bronson Rd, Southport, CT 06890

  First Time on the Market - A Southport Treasure with Endless Possibilities For the first time since 1912, this cherished Southport residence is being offered for sale. Passed down through generations, this classic colonial has been a cornerstone of one family's legacy for over a century - and now it's ready for its next chapter. Set on nearly a half-acre in the heart of Southport, this property

  Vienna DiPiave William Pitt Sotheby's Int'l

  647 Bronson Rd, Southport, CT 06890
• 

  

  /40

  $950,000

  • 3 Beds
  • 2.5 Baths
  • 1,404 Sq Ft

  3 Parsell Ln, Westport, CT 06880

  Spacious home on Cul-de-sac. Large rooms with an abundance of wonderful natural light ! A solid home that offers the perfect canvas to renovate. Gorgeous hardwood floors under carpet in living room, dining room and bedrooms on upper level . Set on 1 acre offering a fantastic opportunity for expansion or a new build. Being sold 'as is".

  Sandra Calise Cenatiempo Settlers & Traders

  3 Parsell Ln, Westport, CT 06880
• 

  

  /31

  $419,900 Open Sat 11AM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,795 Sq Ft

  222 Ellsworth St, Bridgeport, CT 06605

  Don't miss this rare opportunity in the heart of Black Rock! This beautifully updated 1/2 duplex is tucked away from the main street for maximum privacy and tranquility-complete with a large private 0.17 acre yard. Enjoy many modern updates, charming character, and peaceful surroundings just steps from all that Black Rock offers. Home Features: *3 bedrooms, 1.5 updated bathrooms *New roof (3

  Luis Sanchez Sanchez Asset Realty

  222 Ellsworth St, Bridgeport, CT 06605
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  /36

  $499,000

  • 4 Beds
  • 2 Baths
  • 2,036 Sq Ft

  3165 Old Town Rd, Bridgeport, CT 06606

  Turnkey Ranch in Prime North End Bridgeport - Ideal for Investors or Future Homeowners. This renovated single-family home is located in the highly desirable North End of Bridgeport and is just under 3 minutes to Sacred Heart University Campus and Trumbull Mall. This 4 bedroom, 2 bath home nestled on a spacious corner lot offers the perfect balance of quiet suburban living and unbeatable

  Catherine Aaron Berkshire Hathaway NE Prop.

  3165 Old Town Rd, Bridgeport, CT 06606

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