Homes for Sale near J. Milton Jeffrey Elementary School

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  /40

  $1,350,000

  • 3 Beds
  • 2.5 Baths
  • 2,368 Sq Ft

  908 Boston Post Rd Unit 908, Madison, CT 06443

  Experience luxury living in the heart of Madison. This beautifully designed 3-bedroom, 2.5-bath townhouse offers an open layout with 9' ceilings, beautiful, oversized windows, and a gorgeous chef's kitchen equipped with Sub-Zero and Wolf appliances. The light-filled living and dining areas feature a cozy fireplace and seamless flow. The vaulted, south-facing primary suite includes a walk-in

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 354-7246

  908 Boston Post Rd Unit 908, Madison, CT 06443
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  Explore J. Milton Jeffrey Elementary School

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  /33

  $699,500

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

  73 Airline Rd, Clinton, CT 06413

  Discover privacy and space on 3.17acres at 73 Airline Road, just minutes to Clinton or Madison. The upper level of this bright and spacious raised ranch features 3 bedrooms, an office, and 2 full baths. On the main level, there is a complete 1-bedroom apartment with its own laundry and full bath. The home boasts hardwood floors throughout and a beautiful kitchen with GE Profile appliances,

  

  Matt Diamond

  Houlihan Lawrence WD

  (860) 926-5173

  73 Airline Rd, Clinton, CT 06413
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  /15

  $173,500

  • Land
  • 1.55 Acres
  • $111,935 per Acre

  728 Durham Rd, Madison, CT 06443

  Imagine building your dream home on this picturesque 1.55-acre lot in Madison, Connecticut, offering seasonal views of the serene Hog Pond. Throughout the year, enjoy the changing scenery and abundant wildlife, with opportunities for ice skating and hockey on the pond during winter months. The property includes a recent survey with topographical details and a septic design, pending only perc

  

  Gene Pica

  RE/MAX Alliance

  (475) 290-6060

  728 Durham Rd, Madison, CT 06443
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  /34

  $359,000

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft

  313 Bradley Corners Rd, Madison, CT 06443

  Lots of potential in this 4-bedroom 2 full bath colonial in Madison. Private yard, kitchen with adjoining family room, large screen porch leading to deck and backyard, living room with fireplace and dining room. The upstairs as 4 bedrooms all with hardwood floors. A full basement and 2 car garage. Investors take notice. This home needs updating and is being sold as. Great quiet street. With some

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 941-6912

  313 Bradley Corners Rd, Madison, CT 06443
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  /40

  $995,000

  • 4 Beds
  • 2.5 Baths
  • 2,632 Sq Ft

  97 Kelsey Springs Dr, Madison, CT 06443

  Beautiful 4-Bedroom Colonial in a Prime Madison Location! This immaculate home has been thoughtfully upgraded nothing left to do but move in and enjoy. The living room blends contemporary design with classic appeal, while the dedicated office provides the perfect space for working from home. A cozy family room with custom built-ins, a fantastic mud/laundry room, and four spacious bedrooms

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 323-6765

  97 Kelsey Springs Dr, Madison, CT 06443
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  /38

  $340,000

  • 4 Beds
  • 1 Bath
  • 1,756 Sq Ft

  30 Chestnut Hill Rd, Killingworth, CT 06419

  ** A Unique Opportunity at 30 Chestnut Hill Road, Killingworth** Step into a piece of history with this charming antique home, circa 1820-now available from a seasoned preservationist and architect with decades of experience restoring historic homes and barns. This property has already undergone critical structural repairs and has a watertight roof, setting the stage for the next phase of

  Nutan Pawar DreamHomes Realty LLC

  30 Chestnut Hill Rd, Killingworth, CT 06419
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  /39

  $2,295,000

  • 4 Beds
  • 3.5 Baths
  • 4,010 Sq Ft

  64 Webster Point Rd, Madison, CT 06443

  Spacious with amazing waterfront quality views! Sited one house from Long Island Sound on a quiet cul de sac, 64 Webster Point is a private, classic Colonial with spacious, high ceilinged (10' on the first floor), light filled rooms and beautiful hardwood floors throughout the house. A double height foyer flows into the large living room highlighted by a handsome, wood burning fireplace. Adjacent

  Margaret Muir William Pitt Sotheby's Int'l

  64 Webster Point Rd, Madison, CT 06443
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  /40

  $1,499,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 5,267 Sq Ft

  625 State St, Guilford, CT 06437

  Welcome to State Street Haven, an exquisite Georgian-inspired mansion at 625 State Street in the heart of Guilford. Ideally located just minutes from town and nearby neighborhoods, this home offers both convenience and a prestigious address. Every detail exudes sophistication-from the sweeping staircase and soaring ceilings to the updated kitchen and luxurious bathrooms with chandeliers. Four

  Paige Slocum William Raveis Real Estate

  625 State St, Guilford, CT 06437
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  /34

  $670,000

  • 4 Beds
  • 2.5 Baths
  • 3,057 Sq Ft

  39 Stepping Stone Ln, Madison, CT 06443

  New price and $20,000 seller credit offered. Set on over 2 private acres at the end of a quiet cul de sac, this classic Madison Colonial offers space, privacy, and flexible living options. The kitchen features stainless steel appliances and a pantry, and new flooring throughout the main level significantly enhances the home's feel. A screened in porch extends the living space outdoors,

  Cindy Breckheimer Forever Homes Real Estate LLC

  39 Stepping Stone Ln, Madison, CT 06443
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  /10

  $919,900 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,246 Sq Ft

  22 Village Cir Unit 22, Guilford, CT 06437

  Welcome to Guilford's newest luxury community, Village on State. This development features 25 -2 bedroom townhomes each having over 2000 sqft of living space, full basements and 2 car garages. This unit has sweeping views of the grassland adjacent to the complex. This complex has stunning curb appeal with black windows,metal roof accents,and decorative stone. Interior finishes are above and

  Vincent Engingro William Raveis Real Estate

  22 Village Cir Unit 22, Guilford, CT 06437
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  /36

  $140,000

  • 3 Beds
  • 1 Bath
  • 1,128 Sq Ft

  133 W Main St Unit MV1, Clinton, CT 06413

  Welcome to this beautifully updated mobile home offering nearly 1,200 sq. ft. of comfortable living space. With 3 spacious bedrooms and 1 full bath, this home has been thoughtfully renovated to provide modern style and ease of living. Bright and inviting, the open floor plan is filled with natural light, creating a warm and welcoming atmosphere. The kitchen and living areas have been refreshed

  Matt Donafrio GRL & Realtors, LLC

  133 W Main St Unit MV1, Clinton, CT 06413
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  /11

  $385,000

  • Land
  • 26.2 Acres
  • $14,695 per Acre

  247 C Old Toll Rd, Madison, CT 06443

  Two parcels of raw land in North Madison are being offered together as they adjoin. The piece that runs along Old Toll Rd has 535ft of road frontage and is 15.86 acres. The second 10.34 acre piece adjoins along the northern back border and is accessed through the front parcel for a total of 26.2 acres. The front parcel has a level area with small fir trees dotting a field. The parcels have a

  Allyson Cotton William Pitt Sotheby's Int'l

  247 C Old Toll Rd, Madison, CT 06443
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  /28

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,476 Sq Ft

  4 Currycross Rd Unit 4, Madison, CT 06443

  Welcome to highly desirable Windermere East. Windermere is nestled in a private picture perfect setting along the Madison Shoreline. 4 Currycross Road is a charming free standing home with 2 spacious bedrooms and one detached garage just steps to your front door. Home has been freshly painted and boast a lovely open floor plan with a wood burning fireplace, cathedral ceiling, extra attic storage

  Terry Morgan CT Realty Exchange, LLC

  4 Currycross Rd Unit 4, Madison, CT 06443
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  /37

  $2,400,000

  • 4 Beds
  • 2 Baths
  • 3,083 Sq Ft

  153 Middle Beach Rd, Madison, CT 06443

  Charming beach home with full guest apartment above garage across the street from Long Island Sound. Perfect opportunity for personal use, 1031 exchange or investment property. Main house and guest apartment both enjoy decks that overlook beautiful marshes with abundant wildlife. Main house has views of Long Island Sound from the second floor. Guest apartment embraces a full kitchen, family room

  John Campbell Compass Connecticut, LLC

  153 Middle Beach Rd, Madison, CT 06443
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  /40

  $2,190,000 Pre-Foreclosure

  • 5 Beds
  • 3 Baths
  • 3,172 Sq Ft

  15 Highland Terrace, Madison, CT 06443

  COME SEE THIS ONE OF KIND FULLY RENOVATED MADISON HOME WITH PRIVATE BEACH RIGHTS!!! Just 300 feet from the sand, this home was once a traditional raised ranch and now has been brilliantly redesigned into a spacious 'elevated ranch' with an open-concept floor plan that feels airy, bright, and made for entertaining! Step into coastal luxury with this fully reimagined Madison home, where every

  John Cronin Century 21 AllPoints Realty

  15 Highland Terrace, Madison, CT 06443
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  /31

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft

  106 Glenwood Rd, Clinton, CT 06413

  Welcome to 106 Glenwood Road - a long-time family home ready for its next chapter. Owned by the same family since it was built in 1950, this 3-bedroom, 2-bath ranch offers a solid footprint and excellent potential in one of Clinton's quiet residential neighborhoods. The home sits on a spacious 0.84-acre lot just minutes from town beaches, local shops, and commuter routes. Inside, you'll find

  Chaz Koch Coldwell Banker Realty

  106 Glenwood Rd, Clinton, CT 06413
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  /16

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,419 Sq Ft

  75 Fairview Dr, Madison, CT 06443

  3 bedroom 2 full baths close to town private road, close to Bower Park, 2 car garage attached. Totally renovated, Hardwood floors and wood composite laminate's where not oak, bow and bay Anderson windows, a must see!

  Derek Eisenberg Continental Real Estate

  75 Fairview Dr, Madison, CT 06443
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  /25

  $475,000 Open Sat 1PM - 3PM

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft

  24 Railroad Ave, Madison, CT 06443

  Welcome to this charming 2-bedroom Colonial located in the heart of Madison! Filled with character and warmth, this well-maintained home offers a bright and inviting layout perfect for everyday living or a peaceful shoreline retreat. Step inside to discover beautiful hardwood floors, classic Colonial detailing, and sun-filled spaces throughout. The main level features a comfortable living room, a

  Remi Tremblay William Raveis Real Estate

  24 Railroad Ave, Madison, CT 06443
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  /2

  $350,000

  • Land
  • 2.05 Acres
  • $170,732 per Acre

  92 Scotland Rd Unit Lot. 3, Madison, CT 06443

  Build your dream home in the upscale shoreline community of Madison CT! Featured in Yankee Magazine as "Best Beach Towns" in Connecticut and not many land opportunities like this. Centrally located this approved lot is a very large 2.05 acre lot that is level, wooded, and private in a well established upscale neighborhood ONLY 1.2 miles from downtown and approximately 2 miles from Hammonasset

  Stacy Bucci Coldwell Banker Realty

  92 Scotland Rd Unit Lot. 3, Madison, CT 06443
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  /2

  $275,000

  • Land
  • 2.29 Acres
  • $120,087 per Acre

  268 Durham Rd, Madison, CT 06443

  SEEKING TO BUILD YOUR DREAM HOME? Sellers worked with CT Valley Homes who designed a 4 bedroom house + another 2 bedroom guest house. This prime parcel of land offers 2.29 acre with frontage on Rt 79, Durham Road, just north of the Temple Beth Tikvah and just north of Exit 61. You are minutes from I-95, all Madison schools, downtown Madison and beaches. Plans available for review for qualified

  Kirsten Adams William Pitt Sotheby's Int'l

  268 Durham Rd, Madison, CT 06443
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  /2

  $125,000

  • Land
  • 2.7 Acres
  • $46,296 per Acre

  0 Old Toll Rd Unit 24109109, Madison, CT 06443

  Build your dream home in Madison!! 2.7 raw acre lot available in the North Madison section of town. Minutes from Chatfield Hollow State Park and Hammonasset Beach. Extends far enough beyond the main road to enjoy wooded seclusion. Lot has been surveyed, boundary sketch is available.

  Karen Kesten William Raveis Real Estate

  0 Old Toll Rd Unit 24109109, Madison, CT 06443
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  /23

  $164,900

  • 1 Bed
  • 1 Bath
  • 441 Sq Ft

  7 3rd St, Madison, CT 06443

  Madison, SEASHORE! - STEAL OF THE YEAR! REDUCED! SHOWING IN NOV/DEC! Coastal living adjacent to glorious Hammonassett Beach State Park! Turnkey, masterfully updated in 2023. Well-built circa 1958 cottage is the perfect vacation retreat! Looks are deceiving. Open floor plan living room w/vaulted ceiling is wonderfully spacious! Deck is large @412 sf! Young's Village is seasonal providing a 7-month

  Laurie McCann William Pitt Sotheby's Int'l

  7 3rd St, Madison, CT 06443
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  /39

  $850,000

  • 5 Beds
  • 3 Baths
  • 3,992 Sq Ft

  16 Forest Hills Dr, Madison, CT 06443

  Located in one of Madison's most desirable neighborhoods, 16 Forest Hills Drive offers exceptional space and potential. Just minutes from the town center and beaches. This expansive five-bedroom Colonial features an large eat-in kitchen with a cozy fireplace, a spacious formal living room with its own fireplace, and a versatile den/office with extensive built-in cabinets or family room-also with

  Rod Cross Coldwell Banker Realty

  16 Forest Hills Dr, Madison, CT 06443
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  /40

  $875,000

  • 3 Beds
  • 4 Baths
  • 2,279 Sq Ft

  1054 Boston Post Rd, Guilford, CT 06437

  RARE OPPORTUNITY TO OWN TWO BUILDINGS IN GUILFORD ~ Unlock the potential of this prime commercial property on the bustling Boston Post Road, just one block from Guilford's historic town Green. Within the PV zone (Post Road Village Zone District, this offering includes 2 buildings (see listing #1058 Boston Post Road) that share a driveway and provide dedicated parking; an ideal setup for

  Rose Ciardiello William Raveis Real Estate

  1054 Boston Post Rd, Guilford, CT 06437
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  /40

  $345,000

  • 3 Beds
  • 1.5 Baths
  • 1,040 Sq Ft

  15 Egypt Ln, Clinton, CT 06413

  Charming 3-bedroom, 1.5-bath ranch set on a spacious and private 0.68-acre lot in a quiet Clinton neighborhood. This freshly painted, move-in-ready home offers 1,040 sq ft of bright one-level living (not including the large sunroom) with a brand-new roof (2024), new septic system (2024), and a 2-car detached garage. Enjoy the expansive 0.68-acre lot with plenty of room for gardens, play, or

  Sean Seigel RE/MAX Coast and Country

  15 Egypt Ln, Clinton, CT 06413
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  /2

  $949,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,625 Sq Ft

  28 Village Cir Unit 28, Guilford, CT 06437

  New Development. 25 units. Now under construction, Units over 2200 sqft. Full Basement and 2 car garages. Walking distance to town. 3 models to pick from with various locations throughout subdivision.

  Vincent Engingro William Raveis Real Estate

  28 Village Cir Unit 28, Guilford, CT 06437
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  /38

  $410,000

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

  248 Cow Hill Rd, Clinton, CT 06413

  Tucked away in the charming shoreline town of Clinton, this hidden gem welcomes you with a long, private driveway framed by natural grasses and stone outcroppings-setting the stage for ultimate privacy and tranquility. Step inside and be captivated by the main level's airy, open feel, featuring soaring pine cathedral ceilings that bring warmth and character to the family and dining rooms. Sliding

  Kathleen Moniello Coldwell Banker Realty

  248 Cow Hill Rd, Clinton, CT 06413
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  /9

  $1,375,000 New Construction

  • 5 Beds
  • 3.5 Baths
  • 4,357 Sq Ft

  454 Horse Pond Rd Unit B, Madison, CT 06443

  2025 is the year to have the home of your dreams! Come see this gorgeous enclave of five to-be-built houses on a private road in the charming coastal town of Madison. Ideally located just two hours from both NYC and Boston, Madison is beloved for its award-winning schools, restaurants, shops, and of course, beautiful beaches! Constructed by a well-established local Madison builder, these houses

  Karen Rosenthal William Raveis Real Estate

  454 Horse Pond Rd Unit B, Madison, CT 06443
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  /39

  $749,900 Open Sat 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft

  244 Cow Hill Rd, Clinton, CT 06413

  Completely rebuilt in 2025, this stunning home blends modern comfort with thoughtful design on a beautiful 2+ acre setting. Offering 3 spacious bedrooms and 3 full bathrooms, the home features a large eat-in kitchen ideal for gatherings, along with a dedicated dining room complete with a wet bar and beverage refrigerator, perfect for entertaining. The living room showcases soaring cathedral

  Amy Jo Fitzgerald Yellowbrick Real Estate LLC

  244 Cow Hill Rd, Clinton, CT 06413
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  /40

  $1,950,000

  • 5 Beds
  • 9 Baths
  • 5,414 Sq Ft

  173 Highwoods Dr, Guilford, CT 06437

  A MAGNIFICENT REVIVAL & TIMELESS BLEND OF SOMETHING OLD & SOMETHING NEW. One of the finest restorations in New England, the Pitkin mansion is a true historical treasure. Carefully dismantled & moved to its current site in 1955, the property is nestled within nearly 4 acres of mature trees, manicured lawns, & magical gardens. This classic revival will be celebrated by the most discerning antique

  Kiara Rusconi William Raveis Real Estate

  173 Highwoods Dr, Guilford, CT 06437
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  /14

  $869,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,625 Sq Ft

  14 Village Cir Unit 14, Guilford, CT 06437

  Introducing the Dalton! 14 Village Circle is located at Guilford's newest luxury community, Village on State. 14 Village Circle is an end unit and construction is well under way! This model features 2,625 square feet of beautiful living space. The main floor is open concept with a large great room and dining room and kitchen, which is perfect for entertaining. On the upper level you will find the

  Vincent Engingro William Raveis Real Estate

  14 Village Cir Unit 14, Guilford, CT 06437
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  /40

  $540,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,346 Sq Ft

  43 Fort Path Rd, Madison, CT 06443

  Welcome to this adorable ranch in Madison! Stellar location! Just 1 mile from the historic Town Green. Easy access: 1.4 miles to the Madison Surf Club and Train Station, plus close proximity to schools (including the brand new Neck River Elementary) and the picturesque Bauer Park. This 3 bedroom, ONE LEVEL living home with newer appliances is set on nearly an acre of beautifully landscaped

  Lisa Rollins Team Compass Connecticut, LLC

  43 Fort Path Rd, Madison, CT 06443
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  /38

  $549,900

  • 3 Beds
  • 2 Baths
  • 2,034 Sq Ft

  90 Boston Post Rd, Madison, CT 06443

  Great downtown location with beautiful salt marsh views. This lovely 3-bedroom home offers easy living and stunning scenery throughout. The main level includes two bedrooms with a shared full bath, while the private primary suite upstairs features vaulted ceilings, a gas fireplace, full bath, and a balcony overlooking the marsh. The bright living room opens to an oversized deck with serene views

  Kate Jasko Coldwell Banker Realty

  90 Boston Post Rd, Madison, CT 06443
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  /14

  $1,195,000

  • 4 Beds
  • 4 Baths
  • 2,392 Sq Ft

  51 Pearl St, Guilford, CT 06437

  One-of-a-Kind Opportunity in Guilford! Rarely available, this 4-unit multi-family property is ideally located on a large in-town lot in the beautiful shoreline community of Guilford. Built in 1900 and offering 2,392 sq. ft. of living space, the property features one 2-bedroom unit and three 1-bedroom units. Each unit has been thoughtfully updated and includes its own washer/dryer. Three of the

  Philip Warner William Pitt Sotheby's Int'l

  51 Pearl St, Guilford, CT 06437
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  /35

  $745,000

  • 3 Beds
  • 2.5 Baths
  • 2,071 Sq Ft

  141 State St, Guilford, CT 06437

  Welcome to this delightful 3-bedroom Cape Cod on historic State Street, just a short stroll from Guilford's beautiful town green, local shops, and restaurants. Enjoy all the benefits of in-town living in a home that's full of warmth and character. The first-floor primary suite makes everyday living easy, and the updated kitchen and bathrooms add a fresh, modern touch. You'll love the hardwood

  Dana Weinstein Coldwell Banker Realty

  141 State St, Guilford, CT 06437
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  /36

  $1,000,000

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft

  62 Cedar Island Ave, Clinton, CT 06413

  RARE OFFERING It's not often a property like this becomes available! Nicely situated in a prime location just steps to multiple marinas and some of the shoreline's favorite waterfront restaurants, this better-than-new 2-bedroom, 2 full bath, 1-car garage ranch is a standout. Completely rebuilt from the ground up by the current owner, this thoughtfully designed home offers luxurious one-level

  Rose Ciardiello William Raveis Real Estate

  62 Cedar Island Ave, Clinton, CT 06413
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  /9

  $1,425,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,085 Sq Ft

  454 Horse Pond Rd Unit D, Madison, CT 06443

  Gorgeous 4/5BR 3.5BA home in an enclave of five to-be-built houses on a private road in the charming coastal town of Madison. Constructed by a well-established local Madison builder, this home includes all the details you would expect from a meticulously-built brand new home, such as gleaming hardwood floors, 9ft ceilings, energy efficient features, and exceptional craftmanship throughout. This

  Karen Rosenthal William Raveis Real Estate

  454 Horse Pond Rd Unit D, Madison, CT 06443
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  /35

  $739,500

  • 4 Beds
  • 2.5 Baths
  • 3,212 Sq Ft

  174 Concord Dr, Madison, CT 06443

  Step into this exquisitely renovated colonial-style residence, where classic charm seamlessly blends with contemporary sophistication. Gleaming hardwood floors flow throughout the main living spaces, reflecting natural light and enhancing the home's warm ambiance. The heart of the home is a stunning chef's kitchen, thoughtfully designed with state-of-the-art appliances, quartz countertops, and

  Terence Dominick Exceptional Real Estate LLC

  174 Concord Dr, Madison, CT 06443
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  /35

  $330,000

  • 3 Beds
  • 1.5 Baths
  • 2,151 Sq Ft

  3 Medley Ln, Clinton, CT 06413

  Welcome to 3 Medley Lane, a spacious 2,151 sq. ft. ranch-style home nestled in a residential neighborhood just moments to town parks, schools, and the Clinton Crossing Premium Outlets. This 2-3 bedroom home features a flexible layout with a den that can easily serve as a third bedroom, along with 1.5 baths and an inviting open living area where the generous eat-in kitchen flows into the living

  Cheryl Keithan Coldwell Banker Realty

  3 Medley Ln, Clinton, CT 06413
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  /7

  $40,000

  • 776 Sq Ft

  379 Whitfield St Unit CN946, Guilford, CT 06437

  Waterfront - Guilford. Set Sail in Style and experience the charm of Guilford Yacht Club, a premier marina in one of Connecticut's most picturesque coastal towns. This 46-foot slip offers ample space and immediate access to Long Island Sound, ensuring effortless adventures on the water. Guilford is rich in history and natural beauty, making it an ideal destination for boaters. At the Guilford

  Linda Coyle William Raveis Real Estate

  379 Whitfield St Unit CN946, Guilford, CT 06437

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