Homes for Sale near Fairfield Ludlowe High School

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  /33

  $799,900

  • 3 Beds
  • 2 Baths
  • 1,665 Sq Ft

  274 High St, Fairfield, CT 06824

  Welcome to 274 High Street, Fairfield, CT-where timeless elegance meets modern convenience. This beautifully renovated home boasts a fresh and inviting open-concept design, with a stunning new Trex deck just off the kitchen, perfect for relaxing or entertaining. The spacious kitchen features a large island with extra seating, complemented by a stylish design table for additional dining space.

  Karly Worth Call It Closed Realty

  274 High St, Fairfield, CT 06824
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  Explore Fairfield Ludlowe High School

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  /40

  $1,849,000

  • 3 Beds
  • 3.5 Baths
  • 2,760 Sq Ft

  1001 Hulls Farm Rd, Southport, CT 06890

  Situated on 2 manicured acres in Southport and surrounded by multi-million-dollar estates, this gated, European-inspired country home blends timeless charm with modern elegance. A white-pebble drive, stone walls, and sweeping lawns with mature trees create a private estate feel. Inside, the home balances warmth with sophistication. Offering 3 bedrooms on the main level and a 4th bedroom option in

  Ken Banks William Raveis Real Estate

  1001 Hulls Farm Rd, Southport, CT 06890
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  /24

  $999,000

  • 3 Beds
  • 3.5 Baths
  • 2,456 Sq Ft

  21 Beaumont St, Fairfield, CT 06824

  Luxury end-unit 3 bedroom / 3.5 bath townhouse in downtown Fairfield! This home offers a private 4-story in-unit elevator, attached 2-car garage, 2 primary suite options, 9+ foot ceilings, walk-in closets, abundant natural light, and more. The main level features a chef's kitchen with island seating, quartz countertops, Thermador appliances, and a pantry. The kitchen opens to a spacious great

  Carrie Sakey Coldwell Banker Realty

  21 Beaumont St, Fairfield, CT 06824
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  /8

  $1,949,000

  • 6 Beds
  • 5.5 Baths
  • 3,847 Sq Ft

  42 Robin Cir, Fairfield, CT 06824

  Available now for Spring occupancy, with the option to select custom touches that make this home distinctly yours. A brand new home that feels rooted in tradition, yet perfectly suited for modern living. With 6 bedrooms, 5 full baths, 1 half bath, and 3,847 sq. ft. above grade plus the ability to finish additional space in the unfinished lower level with 9' ceilings, this home sits on a sprawling

  Jennifer DeLaurentis Compass Connecticut, LLC

  42 Robin Cir, Fairfield, CT 06824
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  /40

  $1,949,000

  • 6 Beds
  • 5.5 Baths
  • 3,847 Sq Ft

  45 Robin Cir, Fairfield, CT 06824

  SELLER OFFERING RATE BUYDOWN! Secure a lower mortgage rate and reduce your monthly payment--available to buyers who go under contract by November 1, 2025. Don't miss this limited-time opportunity to own a brand-new luxury home with affordable financing. Experience refined living in Fairfield's University Neighborhood. This brand-new construction home by multi HOBI Award-Winning builder

  Jennifer DeLaurentis Compass Connecticut, LLC

  45 Robin Cir, Fairfield, CT 06824
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  /40

  $3,649,000

  • 5 Beds
  • 4.5 Baths
  • 6,607 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 offers a rare opportunity in one of Fairfield's most coveted locations. Set on more than two acres of beautifully landscaped grounds with distant views of Long Island Sound, the property reflects timeless elegance and a sense of place that is hard to replicate today. Across from a distinguished

  Tara Hawley Coldwell Banker Realty

  2683 Bronson Rd, Fairfield, CT 06824
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  /39

  $2,499,000

  • 4 Beds
  • 6 Baths
  • 3,726 Sq Ft

  634 S Benson Rd, Fairfield, CT 06824

  From the moment you arrive, you are captivated w/ blooming gardens & privacy trees that create an inviting curb appeal that welcomes you in. Architecturally gorgeous w/ brilliant craftmanship, this coastal home is a rare find in the Beach neighborhood. Featuring 4 spacious en-suite bedrooms, 12 rooms, 3 levels & an elevator servicing all floors, this home sets a new standard for exceptional

  Jackie Davis William Raveis Real Estate

  634 S Benson Rd, Fairfield, CT 06824
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  /40

  $1,900,000

  • 4 Beds
  • 4.5 Baths
  • 5,283 Sq Ft

  305 S Gate Ln, Southport, CT 06890

  Tucked away on a serene street in the heart of Southport, this 4-bedroom, 4-bath Colonial invites you to experience the perfect balance of elegance, comfort, and privacy. From the moment you arrive, the home's setting feels special - an expansive property framed by mature trees, offering a sense of peace and seclusion. Step inside, and natural light floods the main level, where formal living and

  Elizabeth Tritschler William Raveis Real Estate

  305 S Gate Ln, Southport, CT 06890
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  /31

  $1,999,000

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  137 Millard St, Fairfield, CT 06824

  Stunning NEW construction the desirable Fairfield Beach neighborhood. This gorgeous home is crafted by premier 43 year Fairfield County builder. Premium materials, thoughtful design, and masterful workmanship are showcased throughout. Step inside to find a clean lined, open living space with 9' ceilings. The inviting living room, featuring a captivating 54" cool wall gas fireplace, seamlessly

  Katie O'Grady Compass Connecticut, LLC

  137 Millard St, Fairfield, CT 06824
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  /40

  $1,999,999

  • 5 Beds
  • 3 Baths
  • 4,106 Sq Ft

  215 Old Post Rd, Fairfield, CT 06824

  Old Post Road perfection! Step on to the gracious front porch and be swept away by timeless architecture, graceful design and superb finishes. Beautifully renovated home with so many improvements/amenities including gorgeous expanded kitchen, renovated bathrooms, plantation shutters, new windows, new roof, fresh exterior paint, fencing and more. The inviting foyer welcomes you to a living room

  Katie O'Grady Compass Connecticut, LLC

  215 Old Post Rd, Fairfield, CT 06824
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  /39

  $3,250,000

  • 6 Beds
  • 7.5 Baths
  • 14,110 Sq Ft

  21 Queens Grant Dr, Fairfield, CT 06824

  There are houses you tour, and then there are estates that capture your imagination. This extraordinary Greenfield Hill Colonial is the latter-a 9,700+ sq. ft. residence set on a pristine 2-acre corner lot in one of Fairfield's most prestigious neighborhoods. A paver-stone drive winds past manicured gardens to a grand two-story entry with a sweeping staircase, setting the tone for elegant living.

  Elizabeth Tritschler William Raveis Real Estate

  21 Queens Grant Dr, Fairfield, CT 06824
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  /40

  $1,899,000 Open Sun 1PM - 4PM

  • 5 Beds
  • 4.5 Baths
  • 4,079 Sq Ft

  68 Figlar Ave, Fairfield, CT 06824

  A rare find in today's market & a stunning example of high-end new construction in the sought-after University area awaits - Welcome to 68 Figlar Avenue. This beautifully designed 5 bedroom, 4.5 bath, 11 room home offers 4 levels of living space filled w/ great light & thoughtful details. From the natural white oak flooring to the exquisite millwork & custom built-ins, craftsmanship is evident.

  Jackie Davis William Raveis Real Estate

  68 Figlar Ave, Fairfield, CT 06824
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  /38

  $1,899,000

  • 6 Beds
  • 4.5 Baths
  • 4,344 Sq Ft

  15 Barton Rd, Fairfield, CT 06824

  SELLER OFFERING RATE BUYDOWN! Secure a lower mortgage rate and reduce your monthly payment--available to buyers who go under contract by November 1, 2025. Don't miss this limited-time opportunity to own a brand-new luxury home with affordable financing. Your storybook home-complete with a classic white picket fence-awaits! Where natural light fills inviting spaces, every detail is intentional, &

  Jennifer DeLaurentis Compass Connecticut, LLC

  15 Barton Rd, Fairfield, CT 06824
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  /18

  $2,000,000

  • 4 Beds
  • 2 Baths
  • 1,925 Sq Ft

  20 Ermine St, Fairfield, CT 06824

  Endless opportunities await at this property-whether a buyer envisions their ideal home, a buyer interested in constructing a multigenerational family residence, someone looking to renovate the current home or rebuild and take advantage of the surrounding land, or a builder looking for a new project, this is the perfect place for you, Three individual lots, totaling three secluded acres, are

  Harriet Stone William Pitt Sotheby's Int'l

  20 Ermine St, Fairfield, CT 06824
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  /38

  $3,950,000

  • 5 Beds
  • 4 Baths
  • 4,060 Sq Ft

  353 Old Dam Rd, Fairfield, CT 06824

  Extraordinary waterfront sanctuary offering unmatched privacy and expansive 1.5 acre property in Pine Creek Beach neighborhood. Net Zero, architecturally award-winning home stunningly designed with materials selected for visual appeal, efficiency, longevity. The striking open floorplan flows seamlessly from kitchen to living room and dining area, walls of floor to ceiling windows offer

  Katie O'Grady Compass Connecticut, LLC

  353 Old Dam Rd, Fairfield, CT 06824
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  /32

  $1,075,000

  • 2 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  972 S Pine Creek Rd, Fairfield, CT 06824

  Nestled in a serene, beautifully landscaped community, this gracious townhouse at Pine Ridge offers the perfect blend of privacy and lifestyle. Set around a center green and gazebo, it creates a tranquil and inviting atmosphere. Located within a short walk to the beach, par 3 golf and tennis center. The bright and spacious living room, perfect for entertaining, has nine foot ceilings, a

  Harriet Stone William Pitt Sotheby's Int'l

  972 S Pine Creek Rd, Fairfield, CT 06824
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  /40

  $1,898,500

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

  359 Reid St, Fairfield, CT 06824

  Brand new construction in highly desired Fairfield University area. Beautiful open floor plan includes large kitchen with high end appliances, center island, 36" gas range with hood, wine chiller, microwave drawer, 9 foot ceiling, hardwood floors. The bright airy family room with gas fireplace and a double slider walk out to large deck that overlooks grassy level yard. (The perfect spot for a

  Robert Richter Coldwell Banker Realty

  359 Reid St, Fairfield, CT 06824
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  /40

  $2,349,000

  • 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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  /25

  $1,699,000

  • 4 Beds
  • 3.5 Baths
  • 3,648 Sq Ft

  60 Eleanor Terrace, Fairfield, CT 06824

  Savor the coastal lifestyle in this chic, modern 2021 construction home in the highly desirable Fairfield Beach neighborhood. Just a quick stroll to the beach with pavillion, Fairfield town marina & Sand Castle Park. Hard to find beach area NOT in Flood Zone! No flood insurance required. Thoughtfully designed for open & airy living. Step into open concept living with a spacious living room that

  Katie O'Grady Compass Connecticut, LLC

  60 Eleanor Terrace, Fairfield, CT 06824
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  /38

  $2,199,999

  • 6 Beds
  • 5.5 Baths
  • 5,256 Sq Ft

  59 Thornhill Rd, Fairfield, CT 06824

  Located on one of the most coveted cul-de-sacs in Fairfield's University area, this Newly Built Colonial offers a perfect blend of classic charm & modern luxury. A welcoming stone-trimmed front porch sets the stage for quiet mornings with coffee, while inside, 5-7 bedrooms and 5.5 bathrooms provide ample space for comfortable living and entertaining. The gorgeous open-concept Kitchen with eating

  Julie Vanderblue Higgins Group Real Estate

  59 Thornhill Rd, Fairfield, CT 06824
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  /40

  $1,900,000

  • 4 Beds
  • 4 Baths
  • 4,950 Sq Ft

  260 Range Rd, Southport, CT 06890

  Located on a quiet cul-de-sac in one of Southport's premier family neighborhoods, this elegant 4-bedroom, 2 full and 2 half-bath Colonial by Toll Brothers combines timeless design with modern comfort. The stately "Cedarbrook" Federal Colonial model welcomes you with a grand two-story foyer, setting the stage for the sophisticated interiors. Formal living and dining rooms are ideal for

  Julie Vanderblue Higgins Group Real Estate

  260 Range Rd, Southport, CT 06890
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  /25

  $1,849,000 New Construction

  • 5 Beds
  • 6 Baths
  • 4,150 Sq Ft

  706 Judd St, Fairfield, CT 06824

  Custom New Construction home boasting sophisticated & timeless design in the coveted University area of Fairfield nearing completion September 2025! Carefully crafted by established family owned builders: Coppola & Sons, this home showcases everything from architectural brilliance to intentional functionality for the modern family. The interior includes an open-concept layout that is as versatile

  Melissa Montagno Higgins Group Real Estate

  706 Judd St, Fairfield, CT 06824
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  /18

  $899,000

  • 4 Beds
  • 3 Baths
  • 2,912 Sq Ft

  153 Longview Ave, Fairfield, CT 06824

  Live and invest in the heart of Fairfield, CT - Fantastic opportunity to own a duplex in a prime location. This newly updated 2-family home offers a great combination of modern living and investment potential. Main unit features 3 bedrooms and 2 full baths, with recent renovations that include new hardwood floors and central air. The updated eat-in kitchens are a chef's delight, complete with

  Christine Ricci Keller Williams NY Realty

  153 Longview Ave, Fairfield, CT 06824
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  /24

  $365,000

  • 2 Beds
  • 1 Bath
  • 762 Sq Ft

  633 Black Rock Turnpike, Fairfield, CT 06825

  A single family home close to town with spacious bedrooms and living space. Plenty of storage and parking. Close to all forms of transportation, schools and shopping. Come check it out today!!

  Thomas Mele Dorrance Realty

  633 Black Rock Turnpike, Fairfield, CT 06825
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  /33

  $1,149,000

  • 4 Beds
  • 3.5 Baths
  • 5,081 Sq Ft

  480 Riders Ln, Fairfield, CT 06824

  Welcome to 480 Riders Lane, a timeless mid-century contemporary residence situated at the end of a charming cul-de-sac in the desirable Greenfield Hill neighborhood. This home features 4 to 5 bedrooms and 4 updated bathrooms, offering over 5,000 square feet of carefully crafted living space on a beautiful 2-acre lot, complete with a peaceful pond and fountain. Upon arrival, you'll be welcomed by

  Courtney McManus The Agency

  480 Riders Ln, Fairfield, CT 06824
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  /39

  $1,495,000

  • 5 Beds
  • 2.5 Baths
  • 3,469 Sq Ft

  478 Crestwood Rd, Fairfield, CT 06824

  Classic Colonial in Prime University Area Location. This 1937 Colonial offers four finished levels of living space and a rare combination of character, flexibility, and outdoor living-all set on one of the University Area's most desirable streets. The interior features a thoughtful blend of formal and casual spaces, providing the ideal layout for both everyday living and entertaining. Original

  Wendy Ryan Brown Harris Stevens

  478 Crestwood Rd, Fairfield, CT 06824
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  /31

  $700,000

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft

  225 Papermill Ln, Fairfield, CT 06824

  Enjoy the convenience of walking to town and the train from this charming 3-bedroom, 2-bath home in the highly sought-after University area. Situated on an oversized lot, the property is perfect for entertaining. The living and dining rooms open through sliders to a covered patio, seamlessly connecting indoor and outdoor living. All three bedrooms feature hardwood floors and share easy access to

  Karen Cross William Raveis Real Estate

  225 Papermill Ln, Fairfield, CT 06824
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  /30

  $599,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  270 Oakwood Dr, Fairfield, CT 06824

  Fantastic Opportunity to Update and Make Your Own! This 3-bedroom, 1-bath ranch with an oversized 2-car garage is ready for its next chapter. Featuring hardwood floors, a newer furnace (2021), oil tank (2017), and vinyl siding, the big-ticket items are already in place. With some cosmetic updates and vision, this property offers excellent upside potential-ideal for all end users, investors,

  Elizabeth Altobelli William Raveis Real Estate

  270 Oakwood Dr, Fairfield, CT 06824
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  /37

  $975,000

  • 3 Beds
  • 3 Baths
  • 2,141 Sq Ft

  214 Henry St, Fairfield, CT 06824

  Step inside to an open layout where the big kitchen island steals the show-ideal for casual mornings or hosting friends. Upstairs, the primary suite has great closet space and a private en-suite bath. The finished basement adds even more flexibility, complete with a bonus room that can double as a fourth guest bedroom or an office. With two living rooms, everyone can find their own spot to relax.

  Sean Dobel Houlihan Lawrence

  214 Henry St, Fairfield, CT 06824
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  /37

  $985,900

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft

  294 Catherine Terrace, Fairfield, CT 06824

  Welcome to one of Fairfield's most convienient beach neighborhood locations-where coastal living meets access to town center. Nestled on a quiet wrap around street with no through traffic, this property offers the rare combination of beach proximity and quick access to Fairfield Center. Residents here enjoy the luxury of block parties, neighborly gatherings, and peace of mind that comes with

  Kim Gomes Coldwell Banker Realty

  294 Catherine Terrace, Fairfield, CT 06824
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  /23

  $398,000

  • 2 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  120 Beachview Ave Unit 246, Bridgeport, CT 06605

  Your view everyday ! Welcome to waterfront living in the heart of trendy Black Rock near St Mary's by the Sea. This updated 2-bedroom, 1.5-bath townhouse offers the perfect blend of chic updates and coastal charm. Experience breezy seaside living from your own private deck. Sliding glass doors frame the updated, eat-in kitchen with new quartz counters, stainless steel appliances, new flooring and

  Kelly Finn Coldwell Banker Realty

  120 Beachview Ave Unit 246, Bridgeport, CT 06605
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  /15

  $899,999

  • 3 Beds
  • 1.5 Baths
  • 1,224 Sq Ft

  196 Catherine Terrace, Fairfield, CT 06824

  Nestled close to picturesque beaches, downtown with its award-winning restaurants, and Metro North trains, this charming home is a rare find, offered in as-is condition by the original family owner. A perfect canvas for those looking to create their dream beach area home, with ample potential to modernize and make it your own

  Jim Stobie Berkshire Hathaway NE Prop.

  196 Catherine Terrace, Fairfield, CT 06824
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  /26

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  55 Thorpe St, Fairfield, CT 06824

  Tucked away in the heart of Fairfield Center you have found 55 Thorpe St. This tri-level townhouse is deceivingly spacious. Entry way provides access from the Tandem two car garage, long hall way with ample storage leading you to the rear bonus Den/office with walk out to private green space. As you walk up the staircase to the main level you are greeted with an amazing open concept space and 9ft

  Ashley Petrides William Raveis Real Estate

  55 Thorpe St, Fairfield, CT 06824
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  /40

  $1,199,999

  • 4 Beds
  • 3 Baths
  • 2,012 Sq Ft

  115 Mayfair Rd, Fairfield, CT 06824

  Welcome to 115 Mayfair Road This stunning 4-bedroom, 3-bath home has been fully renovated, right down to the studs, with top-quality finishes and thoughtful design. Step inside to find gleaming plank white oak hardwood floors and an open-concept layout that seamlessly connects the living room, dining area, and chef's kitchen. The gourmet kitchen is a true showpiece with sleek black onyx quartz

  Kenny Bascon Real Broker CT, LLC

  115 Mayfair Rd, Fairfield, CT 06824
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  /40

  $1,289,000

  • 2 Beds
  • 1.5 Baths
  • 1,424 Sq Ft

  1135 Mill Hill Rd, Southport, CT 06890

  The Sherwood Farmhouse set in Southport's Mill Hill area, Circa 1720, is tucked away on a picturesque .48-acre lot in an enchanting country setting. This beautifully preserved and thoughtfully updated historic treasure blends 18th-century charm with modern comforts. Original features such as wide plank floors, hand-hewn beams, custom cupboards, and three working fireplaces speak to the home's

  Amy Waugh Curry ABR CRS GRI Berkshire Hathaway NE Prop.

  1135 Mill Hill Rd, Southport, CT 06890
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  /40

  $890,000

  • 3 Beds
  • 3 Baths
  • 1,709 Sq Ft

  2180 Kings Hwy Unit 1, Fairfield, CT 06824

  Welcome to this like-new, end-unit townhouse offering a blend of timeless elegance and modern comfort, all within walking distance to downtown Fairfield, the train, and beautiful Jennings Beach. This 3 bedroom, 3 full bathroom home is filled with natural light and thoughtfully designed with custom high-end finishes throughout, including shiplap accents, designer lighting and plantation shutters.

  Audrey Ayers William Raveis Real Estate

  2180 Kings Hwy Unit 1, Fairfield, CT 06824
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  /40

  $1,545,000

  • 4 Beds
  • 2.5 Baths
  • 3,597 Sq Ft

  153 Pease Ave, Southport, CT 06890

  Newly Renovated Colonial in Prime Southport Location. Beautifully updated colonial offering modern comfort and timeless style. Featuring a stunning new custom kitchen with a large center island, professional Thermador appliances, and separate butlers pantry, this home is perfect for both everyday living and entertaining. The open floor plan is filled with natural light and has 9ft ceilings

  Basil Amso RE/MAX Right Choice

  153 Pease Ave, Southport, CT 06890
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  /38

  $849,000

  • 4 Beds
  • 2.5 Baths
  • 2,267 Sq Ft

  1009 High St, Fairfield, CT 06824

  Nestled in the heart of Fairfield's sought after University Neighborhood, this timeless Colonial style home, built in 1977, unfolds across 2,267 sq/ft of thoughtfully arranged living space and features incredible storage areas (including a double car garage with loft!) Four well appointed bedrooms and two and a half baths offer a comfortable sanctuary for homeowners. The primary bedroom also

  Francis O'Driscoll Higgins Group Bedford Square

  1009 High St, Fairfield, CT 06824
• 

  

  /14

  $749,000

  • Land
  • 1.02 Acres
  • $734,314 per Acre

  844 Mill Hill Terrace, Fairfield, CT 06890

  This 1.02 acre parcel offers the rare combination of privacy and premier location. Tucked away in a quiet Southport neighborhood, yet just minutes to the harbor, beaches, train, restaurants, and charming village shops - it's the best of both worlds. The possibilities are endless - City water, City sewer and Natural Gas are available in the street. Whether you envision a timeless New England

  Barbara Sweeney Coldwell Banker Realty

  844 Mill Hill Terrace, Fairfield, CT 06890
• 

  

  /20

  $624,900

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  261 High St, Fairfield, CT 06824

  Beautifully updated home ready for its new owners. Featuring a bright open concept floor plan. Gorgeous custom kitchen with shaker cabinets, center island with waterfall countertop and inlay lighting, and new SS appliance package. New paint and hardwood floors throughout. New hardware and LED lighting. Stunning modern tile bath on main level. Finished walk-out lower level adds 600sf of additional

  Basil Amso RE/MAX Right Choice

  261 High St, Fairfield, CT 06824

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