Homes for Sale near The Country School

• 

  

  

  /40

  $699,000

  • 3 Beds
  • 2 Baths
  • 2,035 Sq Ft

  80 Deer Ln, Guilford, CT 06437

  Designed by renowned local architect Gus Dudley and interior designer John Gerson, this striking contemporary home is peacefully nestled among the trees in the private enclave of Robinson's Woods in Guilford. A true retreat, the home features soaring cathedral ceilings in the living room, anchored by a stunning native fieldstone fireplace. Expansive windows fill the space with incredible natural

  

  Wojtek Borowski

  Pearce Real Estate

  (203) 651-7529

  80 Deer Ln, Guilford, CT 06437
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  /31

  $550,000

  • 3 Beds
  • 3 Baths
  • 2,640 Sq Ft

  108 Sandlewood Dr, Madison, CT 06443

  Welcome to easy living with this delightful one-story home in Madison, CT. Located 2.5 miles from the scenic Madison Surf Club! This oversized ranch offers a seamless blend of comfort and potential. Picture yourself unwinding by the fireplace in the cozy living room or enjoying the versatility of the expansive den with plenty of room for flex space or entertaining. This home offers three

  

  Jennifer Bordonaro

  William Pitt Sotheby's Int'l

  (203) 769-9348

  108 Sandlewood Dr, Madison, CT 06443
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  /37

  $2,875,000

  • 4 Beds
  • 4.5 Baths
  • 6,194 Sq Ft

  24 Indigo Trail, Madison, CT 06443

  Come see this stately custom Brick English Georgian home in sought after Madison CT, nestled on a sprawling 5.65 acre lot with Neck River frontage. This exquisite 6,194 square foot colonial offers an unparalleled blend of luxury, privacy and natural beauty. With 4 bedrooms and 4.5 baths, it is designed for those who appreciate both elegance and tranquility. This unique residence is surrounded by

  

  Ron Stewart

  Houlihan Lawrence WD

  (475) 405-2519

  24 Indigo Trail, Madison, CT 06443
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  /37

  $679,000

  • 4 Beds
  • 1.5 Baths
  • 2,458 Sq Ft

  29 Flintlock Rd, Madison, CT 06443

  Welcome to 29 Flintlock Road! This 4-bedroom colonial provides a seamless blend of open design and cozy space. The first floor has hardwood floors, an open floor plan, a welcoming living room with fireplace, and a bright family room set just off the kitchen-perfect for gatherings. Upstairs, you'll find four spacious bedrooms with hardwood floors and an updated full bathroom. The finished basement

  

  Betsy Anderson

  William Pitt Sotheby's Int'l

  (203) 875-0286

  29 Flintlock Rd, Madison, CT 06443
• 

  

  

  /40

  $789,900

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

  472 Saw Mill Rd, Guilford, CT 06437

  Park like setting in one of the shoreline's most vibrant towns. This private location is still close to commute , shopping, and historic Town Center. School yards with tennis, soccer fields, and golf course are just a few of the benefits of Guilford living. Beaches, and fine restaurant scene as well. Your new HOME here features a large updated kitchen, hardwood flooring, stone fireplaces,

  

  Clayton Janer

  Clayton Property Brokers L.L.C

  (203) 896-8851

  472 Saw Mill Rd, Guilford, CT 06437
• 

  

  /40

  $3,000,000

  • 6 Beds
  • 4.5 Baths
  • 6,300 Sq Ft

  37 Lantern Hill Rd, Madison, CT 06443

  Welcome to 37 Lantern Hill Road, a luxurious residence nestled in the heart of Madison's most coveted neighborhood. Just a short stroll from pristine beaches, the charming town center, and the Madison Country Club, this home offers an unparalleled lifestyle of comfort and convenience. Tucked away along picturesque brick-lined sidewalks and illuminated by classic lanterns, this exceptional

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 283-9847

  37 Lantern Hill Rd, Madison, CT 06443
• 

  

  /13

  $115,000

  • Land
  • 2.07 Acres
  • $55,556 per Acre

  78 & 80 Airline Rd, Clinton, CT 06413

  Wonderful opportunity to build your dream home on 2 acres of property in this serene and tranquil setting. Enjoy the sounds of the babbling brook, and feel at peace! Frontage on both Airline Rd and Walkley Mill offer the potential for easy access into the land! A beautiful and natural site for a home to sit on, yet still close to downtown Clinton and Madison, fishing, Hammonassett State Park,

  

  Dylan Walter

  William Raveis Real Estate

  (860) 935-6383

  78 & 80 Airline Rd, Clinton, CT 06413
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  /40

  $2,650,000

  • 5 Beds
  • 7.5 Baths
  • 8,476 Sq Ft

  75 Half Mile Rd, Guilford, CT 06437

  Introducing a custom-built Adirondack-style masterpiece, set on over 5 acres of pristine land. Designed with care by the current owners, this home boasts a seamless layout, ideal for entertaining. Spacious, elegantly appointed rooms feature a custom-designed kitchen, soaring ceilings, and a stunning two-sided stone fireplace. Each bedroom is en suite, offering both privacy and luxury. The

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 255-6899

  75 Half Mile Rd, Guilford, CT 06437
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  /40

  $625,000

  • 3 Beds
  • 3,768 Sq Ft

  36 Jannas Ln, Madison, CT 06443

  Hey there! Check out this stunning contemporary house located just a few houses north of Rt 1. It's sitting on a knoll and has so much potential, but it does need a complete remodeling. This is your chance to redesign the interior and make it your own! The location is perfect - close to town, the Long Island Sound, and even a golf course. This could be your ideal summer retreat or a cozy

  

  Harry Finer

  William Raveis Real Estate

  (203) 580-6329

  36 Jannas Ln, Madison, CT 06443
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  /39

  $2,750,000

  • 10 Beds
  • 8.5 Baths
  • 4,734 Sq Ft

  10 & 12 Firetower Rd, Killingworth, CT 06419

  Turn into the driveway and the stunning surroundings will melt your stress away. A rare find of two properties on 20+ acres of exquisite grounds bordered by Chatfield Hollow Park and includes a private residence, caretaker's dwelling, and a cabin that feels like you're miles away in a wilderness lodge. The primary residence, a 5 bedroom, 3 bath mid-century modern with an infinity-edge pool that

  

  Betsy Anderson

  William Pitt Sotheby's Int'l

  (860) 431-3151

  10 & 12 Firetower Rd, Killingworth, CT 06419
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  /25

  $450,000

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  36 State St, Guilford, CT 06437

  Don't miss this extraordinary opportunity to own a picture-perfect retreat just steps from the Guilford Green. Whether you're seeking a charming pied-a-terre, a weekend escape, or a sophisticated condo alternative, this well maintained residence checks every box. Thoughtful updates and modern upgrades blend with the simple character of this home. Enjoy peace of mind with a brand-new septic

  

  Janet Cronin-Rumanoff

  William Pitt Sotheby's Int'l

  (475) 445-1124

  36 State St, Guilford, CT 06437
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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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  /40

  $1,595,000

  • 4 Beds
  • 3.5 Baths
  • 5,219 Sq Ft

  12 Stanton Ct, Madison, CT 06443

  Just minutes from Madison's beautiful beaches and vibrant town center, this exceptional architect-designed home sits at the end of a quiet cul-de-sac. Light-filled and thoughtfully designed, it features a newly remodeled custom kitchen and an open, airy floor plan ideal for modern living. With 4 bedrooms and 3.5 baths, the home includes a spacious primary suite showcasing a wall of windows that

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 303-6867

  12 Stanton Ct, Madison, CT 06443
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  /40

  $1,995,000

  • 5 Beds
  • 3.5 Baths
  • 3,912 Sq Ft

  30 Meeting House Ln, Madison, CT 06443

  Once known as "Hartsbourne," this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the neighboring Congregational Church, the home

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 442-9594

  30 Meeting House Ln, Madison, CT 06443
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  /39

  $990,000

  • 3 Beds
  • 2.5 Baths
  • 2,558 Sq Ft

  659 Summer Hill Rd, Madison, CT 06443

  Have Fun! Summer: pool, large deck, fenced yard, and central AC! Winter: Fireplaces, holiday meals, room for guests. Yesterday's charm & all the conveniences of today (new roof, new boiler, new central AC, Updated Kitchen) With wide plank Chestnut floors and 3 fireplaces on the first floor: the vintage house charm with current comfort is inviting! Access to the deck from the Dining Room and

  Leigh Whiteman William Raveis Real Estate

  659 Summer Hill Rd, Madison, CT 06443
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  /38

  $850,000

  • 3 Beds
  • 3 Baths
  • 2,220 Sq Ft

  330 Foxwood Rd, Guilford, CT 06437

  Set on a serene .92-acre lot in one of Guilford's most desirable neighborhoods, this impeccably maintained 3-bedroom, 3-bath home offers 2,220 square feet of thoughtfully designed living space. With numerous upgrades and attention to detail throughout, this property perfectly blends comfort, functionality, and style. Step inside to find a warm and inviting layout featuring spacious living areas,

  Eric Ryalls William Pitt Sotheby's Int'l

  330 Foxwood Rd, Guilford, CT 06437
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  /40

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 2,517 Sq Ft

  45 Graves Ave, Guilford, CT 06437

  This stunning Light and Bright 9 room, 2517 SQ FT historic gem is located in the heart of Guilford on a small, quiet street mere steps from the charming Guilford Green. This spacious home was built in 1906, with room for 4 bedrooms, 2.5 fully remodeled baths and a huge 25X20 Bonus Room in the finished attic with additional unfinished space for expansion or extra storage. With a mix of historic

  Debbie Robinson Pearce Real Estate

  45 Graves Ave, Guilford, CT 06437
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  /40

  $1,389,000

  • 4 Beds
  • 3.5 Baths
  • 4,072 Sq Ft

  14 Ely Ln, Killingworth, CT 06419

  Killingworth CT-Stunning 4072 sf 4 bedroom, 3 1/2 bath masterfully built Colonial. This beyond compare property must be seen. Owners have created an outstanding wellness retreat. Tour it by appointment to understand the PRIVACY, joy of nature + obvious lifestyle amenities: Gunite salt water heated pool, several patio areas, beautiful fenced in established gardens plus an additional fenced in area

  Laurie McCann William Pitt Sotheby's Int'l

  14 Ely Ln, Killingworth, CT 06419
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  /40

  $1,469,000

  • 2 Beds
  • 2 Baths
  • 2,035 Sq Ft

  66 High St Unit 31, Guilford, CT 06437

  Spectacular Marsh Views and Refined Living at 66 High Street - Guilford, CT! Perfectly positioned on the first floor of the Leete Building, Step into unit 31, a thoughtfully designed open floor plan that blends historic charm with contemporary style. To the right of the welcoming hallway, the chef's kitchen is outfitted with premium stainless-steel appliances-including a Wolf gas range, Sub-Zero

  Nicole White William Raveis Real Estate

  66 High St Unit 31, Guilford, CT 06437
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  /39

  $995,000

  • 3 Beds
  • 3 Baths
  • 2,728 Sq Ft

  109 Boston Post Rd, Madison, CT 06443

  Built in 1854 for the Chittenden family, this historic Madison home sits on a beautifully landscaped, level one-acre lot and blends classic New England charm with modern upgrades. The main residence features three bedrooms on the second floor, plus a finished third-floor loft that serves as a fourth bedroom, office, or playroom. A highlight is the detached oversized garage with a connected studio

  Jack Hill Seabury Hill REALTORS

  109 Boston Post Rd, Madison, CT 06443
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  /40

  $1,175,000

  • 3 Beds
  • 2.5 Baths
  • 4,994 Sq Ft

  45 Shaker Ct, Guilford, CT 06437

  Introducing 45 Shaker Court, Guilford - experience the Art of Living in This One-of-a-Kind Custom Estate! Discover a stunning blend of Californian, Tuscan, and Ranch-style architecture in this uniquely spacious and beautifully designed home, nestled in one of the area's most desirable neighborhoods. Offering exceptional privacy and timeless elegance, this stunning residence features a coveted

  Nicole White William Raveis Real Estate

  45 Shaker Ct, Guilford, CT 06437
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  /26

  $850,000

  • 3 Beds
  • 1.5 Baths
  • 1,116 Sq Ft

  57 Circle Beach Rd, Madison, CT 06443

  Nestled along the shores of Long Island Sound, this classic 3-bedroom, 1.5-bath, this 1116 sq.ft cottage offers a rare opportunity to own a true waterfront retreat with panoramic views-including Faulkner's Island-and a separate deep water dock on the Neck River just across the street. From the moment you step inside, you're welcomed by sweeping, unobstructed water views and endless potential.

  Cheryl Kebalo ENRG Global Realty, LLC

  57 Circle Beach Rd, Madison, CT 06443
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  /9

  $1,375,000

  • 6 Beds
  • 5 Baths
  • 8,265 Sq Ft

  7 Hart Rd, Guilford, CT 06437

  A Literary Legacy Meets Architectural Elegance! After publishing her best-selling novel The Thorn Birds, author Colleen McCullough designed and built this extraordinary residence as her personal sanctuary-a place that balanced proximity to New York with the peaceful seclusion of forested hills and a gently flowing brook. Nestled at the end of a winding private drive, the home welcomes you with a

  Gaetano Marra BHGRE Gaetano Marra Homes

  7 Hart Rd, Guilford, CT 06437
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  /40

  $875,000

  • 4 Beds
  • 2.5 Baths
  • 4,879 Sq Ft

  48 Shepherds Trail, Madison, CT 06443

  Welcome to your private oasis-This one-of-a-kind Contemporary Colonial home offers 4 bedrooms, 2.5 baths, and a versatile floor plan designed for both grand entertaining & everyday comfort. Step into the impressive foyer, where an expansive living room & formal dining area set the stage for elegant gatherings. The kitchen at the heart of the main level gleams with granite countertops,

  Erin Connelly Coldwell Banker Realty

  48 Shepherds Trail, Madison, CT 06443
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  /40

  $950,000

  • 3 Beds
  • 4 Baths
  • 4,448 Sq Ft

  3 Arrowhead Rd, Madison, CT 06443

  Welcome to Madison and the magic of Shoreline Living at its best. Nestled in a small community of homes living with immediate access to the river is 3 Arrowhead. As you enter your home you are greeted with sun filled rooms that bring the outside in, along with all of the beautiful sounds of chirping birds. The easy flow of your designer kitchen, adjacent dinning room and spacious living room

  Diana Hartman William Pitt Sotheby's Int'l

  3 Arrowhead Rd, Madison, CT 06443
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  /33

  $995,000

  • 4 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  15 Briarwood Dr, Guilford, CT 06437

  Located on a quiet, no-through street, in a Guilford desirable neighborhood, this home offers the perfect blend of convenience, and vacation-inspired lifestyle-just 5 miles from the beach, marinas, eateries, golfing, shopping, I95, and more. Ideal for year-round living or a weekend retreat. Inside, the home has been extensively upgraded including mechanical systems, new septic system, central

  Melanie Taylor Berkshire Hathaway NE Prop.

  15 Briarwood Dr, Guilford, CT 06437
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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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  /31

  $899,000

  • 3 Beds
  • 3.5 Baths
  • 3,772 Sq Ft

  13 Longview Terrace, Madison, CT 06443

  Privately sited at the end of Longview Terrace with expansive marsh and river views this larger than most free-standing colonial at over 3700 sf offers luxurious condo living. With a three-story generous layout this unit is south facing and full of light and custom details. The oversized kitchen with breakfast area is open to a 22x17 private deck. The primary suite offers a fireplace, a very

  Margaret Muir William Pitt Sotheby's Int'l

  13 Longview Terrace, Madison, CT 06443
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  /15

  $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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  /9

  $789,900 New Construction

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

  16 Village Cir Unit 16, Guilford, CT 06437

  Welcome to Guilford's newest luxury community, Village on State. This development features 25 - 2 bedroom townhomes, each having over 2000 square feet of living space, 2 car garages and full basements. The road for the development has recently been paved! Several floor plans are available to choose from which allow for primary bedroom suites on the first or second floor, spacious eat-in kitchens

  Vincent Engingro William Raveis Real Estate

  16 Village Cir Unit 16, Guilford, CT 06437
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  /7

  $879,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,428 Sq Ft

  876 Nut Plains Rd Unit Lot 3, Guilford, CT 06437

  LAST LOT AVAILABLE - Introducing an exquisite gem nestled just a couple miles from our charming Town Green - the epitome of modern living awaits you in our brand-new, 3-home subdivision. These homes represent a harmonious blend of contemporary aesthetics, soaring ceilings, 8ft windows, and a sense of elegance, designed to captivate both your senses and your heart. Step into a world of refined

  Adrian Price Sunset Creek Realty, LLC

  876 Nut Plains Rd Unit Lot 3, Guilford, CT 06437
• 

  /2

  $929,000 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.

  Vincent Engingro William Raveis Real Estate

  28 Village Cir Unit 28, Guilford, CT 06437
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  /40

  $1,000,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,513 Sq Ft

  423 Whitfield St, Guilford, CT 06437

  Truly exceptional turnkey property sits on a peaceful 1-acre lot along the desirable, sidewalk-lined Whitfield Street. This fully renovated and thoughtfully reimagined home offers light-filled living spaces, beautiful hardwood flooring, and crown molding throughout. Charming curb appeal welcomes you with an inviting front porch that leads into a living room with a gas fireplace. The open-concept

  Rose Ciardiello William Raveis Real Estate

  423 Whitfield St, Guilford, CT 06437
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  /39

  $1,665,000

  • 5 Beds
  • 6 Baths
  • 5,779 Sq Ft

  110 Randi Dr, Madison, CT 06443

  Welcome to 110 Randi Drive, where a stately circular driveway ushers you into a realm of elegance & comfort. This grand & classic 5,779 sf residence is a testament to luxurious living, offering a harmonious blend of expansive open areas. As you step through the front door, you're greeted by a formal living room adorned w/ French doors & the first of 3 fireplaces, a space that could effortlessly

  Amy Kirst William Pitt Sotheby's Int'l

  110 Randi Dr, Madison, CT 06443
• 

  

  /26

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,260 Sq Ft

  34 Joyce St, Guilford, CT 06437

  Pristine 4 bedroom, 2 full bath contemporary style home located in a well kept neighborhood close to the Guilford Town Green, shops, restaurants, Yale Hospital, as well as easy highway access! From the moment you enter, you'll appreciate how picture-perfect and well maintained this home truly is. Highly desirable 1 floor living with 3 bedrooms on the main floor, plus a beautifully appointed

  Lisa Rollins Team Compass Connecticut, LLC

  34 Joyce St, Guilford, CT 06437
• 

  

  /27

  $465,000

  • 3 Beds
  • 1.5 Baths
  • 1,468 Sq Ft

  20 Robin Ridge Dr, Madison, CT 06443

  Welcome to 20 Robin Ridge Drive, a charming ranch-style home located in the highly sought-after Robin Ridge neighborhood! Ideally located just over 2 miles from Downtown Madison and approximately 3 miles to the Madison Beach Hotel, West Wharf Beach, and the Surf Club, this property combines comfort, convenience, and coastal living. This inviting home offers 3 generously sized bedrooms with

  Anne Marie Straka Compass Connecticut, LLC

  20 Robin Ridge Dr, Madison, CT 06443
• 

  

  /39

  $700,000

  • 4 Beds
  • 2.5 Baths
  • 2,424 Sq Ft

  310 Opening Hill Rd, Madison, CT 06443

  Welcome to this charming and extensively updated colonial home that embodies comfort and style. With a wealth of improvements completed in 2014, including new windows, roof, driveway and a beautiful kitchen, this home is move-in ready. Recent enhancements in 2024 include an updated primary bath and half bath, making it even more inviting for you and your guests. The added Ring doorbell, newly

  Barbara Goetsch William Pitt Sotheby's Int'l

  310 Opening Hill Rd, Madison, CT 06443
• 

  

  /38

  $575,000

  • 3 Beds
  • 2 Baths
  • 2,159 Sq Ft

  9 Madrina Ln, Madison, CT 06443

  Tucked away at the end of a quiet cul-de-sac, this 3-bedroom, 2-bath contemporary style home sits on a private .6-acre lot in a desirable location; just minutes from beaches, Hammonasset State Park, the scenic Shoreline walking trails, and the vibrant center of town. Steps lead up to the front deck and entry foyer, opening to a light-filled, open-concept living space. Cathedral ceilings with

  Rose Ciardiello William Raveis Real Estate

  9 Madrina Ln, Madison, CT 06443
• 

  

  /22

  $899,900

  • Land
  • 0.19 Acre
  • $4,736,316 per Acre

  885 Boston Post Rd, Madison, CT 06443

  Fully approved and ready to go, this exceptional commercial lot is situated in the heart of vibrant downtown Madison. Boasting approvals for a 5,000 square foot building the property includes a brand-new septic system, 13 designated parking spaces with additional parking options, and unbeatable proximity to restaurants, shopping, the train station, and I-95. Imagine welcoming clients or customers

  Michael Hvizdo Coldwell Banker Realty

  885 Boston Post Rd, Madison, CT 06443
• 

  

  /35

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 3,120 Sq Ft

  41 Sportsman Hill Rd, Madison, CT 06443

  Welcome to this spacious and versatile Colonial home located less than 2 miles from charming downtown Madison, CT. With 4-5 bedrooms, 3.1 baths, and three fireplaces, this home offers the perfect blend of classic elegance and modern functionality. The large living room with fireplace is ideal for gatherings, while the inviting family room features built-in cabinetry, bookshelves, a cozy

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  41 Sportsman Hill Rd, Madison, CT 06443

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