Homes for Sale near The Country School

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  /39

  $1,895,000

  • 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

  (475) 252-9212

  30 Meeting House Ln, Madison, CT 06443
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  Explore The Country School

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  /40

  $1,299,000

  • 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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  /34

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,459 Sq Ft

  4 Copper Ridge Cir, Guilford, CT 06437

  Nestled on a quiet cul-de-sac in the sought-after Copper Hill Village, this detached Cape-style condo offers the privacy of a single-family home with the effortless lifestyle of a managed community. Boasting 1,459 square feet of bright, airy living space, this 2-bedroom, 2-bathroom residence is designed for comfort and versatility.The heart of the home features a living area with a cozy

  

  Rob McConville

  RE/MAX Heritage

  (203) 941-7511

  4 Copper Ridge Cir, Guilford, CT 06437
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  /37

  $999,000

  • 3 Beds
  • 2.5 Baths
  • 1,837 Sq Ft

  461 Green Hill Rd, Madison, CT 06443

  Rare 7-Acre Madison Estate: Equestrian Dream Meets Modern Antique Charm Discover the perfect blend of tranquility and coastal convenience at this stunning 7.02-acre estate, located just 1.9 miles from the heart of downtown Madison. Whether you are a dedicated equestrian, a nature lover, this property offers a rare combination of level, lightly wooded land and functional luxury. The Land &

  

  Cory Tyler

  Berkshire Hathaway NE Prop.

  (475) 262-9624

  461 Green Hill Rd, Madison, CT 06443
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  /40

  $2,199,000

  • 4 Beds
  • 4 Baths
  • 2,850 Sq Ft

  81 Strawberry Hill Rd, Madison, CT 06443

  Modern luxury in a premier location. Set on over two private acres in a highly desirable neighborhood, this brand-new contemporary home offers an open, light filled floor plan designed for both comfort and style. The chef's kitchen is a standout, featuring a Subzero refrigerator, Wolf appliances, custom cabinetry, and elegant quartzite countertops. It flows seamlessly into the expansive great

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 265-5747

  81 Strawberry Hill Rd, Madison, CT 06443
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  /35

  $719,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,589 Sq Ft

  21 Little Hollow Rd, Madison, CT 06443

  Beautifully maintained classic cape offering charm and privacy and convenience. Set at the end of a cul-de-sac, the property features a private, garden-filled backyard and is just moments from town and beaches. Sun drenched rooms and many updates and improvements make this exceptional home completely move in ready. Recent upgrades include , New roof October 2025, updated energy efficient windows,

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 774-4212

  21 Little Hollow Rd, 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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  /37

  $1,110,000

  • 3 Beds
  • 3.5 Baths
  • 3,545 Sq Ft

  11 Longview Terrace, Madison, CT 06443

  An exceptional stand-alone condominium that captures the essence of luxurious coastal living. Tucked away on a peaceful cul-de-sac in the highly desirable Strathmore Farms community. Thoughtfully designed interior features a spacious first-floor primary suite with walk-in closets, custom built-ins, and a dressing room that exudes comfort and convenience. The kitchen is a true delight, offering

  Bonnie Foster William Pitt Sotheby's Int'l

  11 Longview Terrace, Madison, CT 06443
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  /32

  $1,595,000

  • 4 Beds
  • 4 Baths
  • 2,966 Sq Ft

  147 Boston St, Guilford, CT 06437

  Discover the vibrant energy of the historic town green just outside your doorstep. The inviting sidewalk guides you to the lively center, only 600 yards away. There, you'll find a treasure trove of quaint shops, restaurants, the recreational center, and cozy coffee spots to enjoy. Join in the community spirit at concerts and local events, and explore the area's rich history and character-all

  Vicky Welch William Raveis Real Estate

  147 Boston St, Guilford, CT 06437
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  /38

  $2,595,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 4,700 Sq Ft

  23 Sheep Pasture Rd, Madison, CT 06443

  Built by a highly regarded shoreline builder known for uncompromising attention to detail, this residence is designed for buyers who appreciate elevated finishes, enduring quality, and effortless livability. The home features an open floor plan with white oak hardwood floors, 9-foot ceilings, custom millwork, and oversized Pella windows throughout. A stunning bluestone entry leads to an elegant

  Steve Wollman Wollman Realty

  23 Sheep Pasture Rd, Madison, CT 06443
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  /32

  $715,000

  • 3 Beds
  • 1.5 Baths
  • 1,672 Sq Ft

  294 Church St, Guilford, CT 06437

  Mixed-use zoning (convertible to full commercial with town permits) 2,005 sq ft total / 1,672 sq ft finished living space..30 acre lot with generous parking (10+ vehicles) Year built: 1893 with numerous modern updates. Rare to find a house in Guilford with "public water". Current layout: First Floor: Professional medical office space, 4 office space + half bath Second Floor: 1-bedroom apartment,

  Jason Saphire www.HomeZu.com

  294 Church St, Guilford, CT 06437
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  /4

  $989,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,814 Sq Ft

  0 Long Hill Rd Unit 24156467, Guilford, CT 06437

  Here is your opportunity to build this beautifully designed 2,814 sq ft Cape-style home privately situated on a rear lot! This thoughtfully crafted To Be Built home blends classic New England charm with today's clean farmhouse aesthetic - board-and-batten accents, striking black windows, and timeless architectural lines. The open-concept main level is designed for today's lifestyle, featuring a

  Dori Degennaro William Raveis Real Estate

  0 Long Hill Rd Unit 24156467, Guilford, CT 06437
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  /40

  $2,600,000

  • 4 Beds
  • 3.5 Baths
  • 5,543 Sq Ft

  137 Liberty St, Madison, CT 06443

  Rare opportunity to own in desirable Liberty Street area. This 1816 Federal-style residence & new detached historically designed barn, renovated and built by prominent historical design/build specialists Gulick & Co., creates a harmonious blend of formality and comfort. The main residence has 3,784 sq ft of living space, and the detached barn boasts 1,776 sq ft. The main residence is a

  Alison Gould Gould Group LLC

  137 Liberty St, Madison, CT 06443
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  /2

  $889,900 New Construction

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

  35 Village Walk Unit 35, 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

  35 Village Walk Unit 35, Guilford, CT 06437
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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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  /39

  $2,495,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,143 Sq Ft

  92 Scotland Ave, Madison, CT 06443

  Less than one mile from downtown Madison, this new construction home offers refined living with white oak floors, custom millwork, coffered ceilings, and abundant natural light throughout. The main level features 9-foot ceilings, a dramatic floor-to-ceiling gas stone fireplace with built-ins, a chef's kitchen with Sub-Zero and Wolf appliances, double ovens, pot filler, wet bar with wine chiller,

  Steve Wollman Wollman Realty

  92 Scotland 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

  $84,900

  • Land
  • 2.7 Acres
  • $31,444 per Acre

  115 Hemlock Dr, Killingworth, CT 06419

  2.7 Acre Lot located on the corner of Hemlock Drive + Route 80. Not far from the circle and Chatfield Hollow. Previously approved for a 2-3 Bedroom home. Test hole data and previous house plan available.

  Craig Milton Re/Max Valley Shore

  115 Hemlock Dr, Killingworth, CT 06419
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  /31

  $425,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft

  296 Valley Shore Dr, Guilford, CT 06437

  Welcome to 296 Valley Shores Drive. Easy living in this 3-bedroom, 2 bath ranch style home in a water area community awaits! This property invites you in through the double front doors, impressive floor to ceiling brick fireplace, vaulted ceilings, and expansive back deck with access from living room, kitchen and primary bedroom. The charm doesn't stop with a lightly treed lot and babbling brook

  Claire Kilmer Coldwell Banker Realty

  296 Valley Shore Dr, Guilford, CT 06437
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  /40

  $729,000

  • 4 Beds
  • 1,804 Sq Ft

  26 Water St, Guilford, CT 06437

  Ideally located in the heart of downtown Guilford, 26 Water Street is now officially available. Situated within the Guilford Green District, this property offers exceptional versatility with a wide range of permitted uses (see attached zoning regulations, Section 4.1). The existing use may continue as a non-conforming use if desired. The current layout is configured similarly to a multi-family

  Lauren Freedman Coldwell Banker Realty

  26 Water St, Guilford, CT 06437
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  /2

  $26,250

  • 756 Sq Ft

  379 Whitfield St Unit AN2542, Guilford, CT 06437

  42' boat slip on A dock at the Gorgeous Guilford Yacht Club. Includes heated pool and tennis. Beautiful location on the West River

  Debbie Robinson Pearce Real Estate

  379 Whitfield St Unit AN2542, Guilford, CT 06437
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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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  /40

  $620,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,687 Sq Ft

  223 Water St, Guilford, CT 06437

  Turn-key with peaceful marsh views, just 0.5 mi from the vibrant Guilford Town Green! Enter through the picture-perfect front screened porch- an idyllic spot to sip morning coffee or unwind in the evening while overlooking cascades of hydrangeas and serene West River marsh scenery. Inside, this meticulously maintained and thoughtfully updated Cape Cod blends timeless charm with modern comfort.

  Katie Westrin William Raveis Real Estate

  223 Water St, Guilford, CT 06437
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  /40

  $825,000

  • 4 Beds
  • 3 Baths
  • 3,462 Sq Ft

  40 Hull Rd, Madison, CT 06443

  Seldom-available offering in one of Madison's premier neighborhoods. This versatile split-level home sits on a double lot spanning over 2 acres, offering exceptional privacy and room to grow. Set back from the street with a circular driveway, the property unfolds to reveal 4+ bedrooms, 3 full baths, and flexible living spaces designed for how you live today. The kitchen, which is the heart of the

  Sue Woods William Pitt Sotheby's Int'l

  40 Hull Rd, Madison, CT 06443
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  /40

  $799,000

  • 4 Beds
  • 2 Baths
  • 2,174 Sq Ft

  402 Boston St, Guilford, CT 06437

  Antique charming house, modern quality updates with preserved antique charm and character, beautiful details, quality, character, and lovingly well-maintained. Stainless steel appliances, tiled bathrooms, bookcases galore, FENCED YARD. Upgrades include ducted central air, 4 heat zones, newer landscaping; many rooms with beautiful antique oak flooring; newer windows, roof, garage doors; vaulted

  Gloria Gibney Gibney Real Estate

  402 Boston St, Guilford, CT 06437
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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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  /40

  $1,450,000 Coming Soon

  • 4 Beds
  • 5 Baths
  • 3,779 Sq Ft

  395 Boston Post Rd, Madison, CT 06443

  Introducing the historic Ebenezer Dudley Home, circa 1828, a beautifully preserved residence set along the iconic stretch of Boston Post Road in the charming shoreline town of Madison, Connecticut. Situated on nearly an acre of picturesque grounds, this special property seamlessly blends early New England character with thoughtful modern updates, offering both historic charm and everyday comfort.

  Laurie Mazzeo William Pitt Sotheby's Int'l

  395 Boston Post Rd, Madison, CT 06443
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  /35

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,256 Sq Ft

  258 Nut Plains Rd, Guilford, CT 06437

  Welcome to 258 Nut Plains Road, a beautifully updated home offering over 2,000 square feet of comfortable living space. Freshly painted throughout, this inviting property features Luxury Vinyl Plank floors that flow seamlessly from room to room, creating a warm and cohesive feel. The updated kitchen is designed for both style and functionality, highlighted by sleek quartz countertops and modern

  Matt Healy Coldwell Banker Realty

  258 Nut Plains Rd, Guilford, CT 06437
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  /4

  $21,000

  • 680 Sq Ft

  379 Whitfield St Unit BN334, Guilford, CT 06437

  Enjoy convenient and carefree boating from this safely located boat slip. Guilford Yacht Club has been recently dredged for improved depth and accessibility. This ideal easy access to Long Island Sound provides the most of your time on the water. Ownership includes club membership with a vibrant community of boaters. Take advantage of the club pool and year round social activities. The pump-out

  Rod Cross Coldwell Banker Realty

  379 Whitfield St Unit BN334, Guilford, CT 06437
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  /40

  $649,900

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

  80 Seaview Terrace Unit 31, Guilford, CT 06437

  Coastal Living Reimagined at Seaview Terrace Welcome to your completely renovated waterside retreat where modern luxury meets the ultimate Shoreline lifestyle. This stunning 2-bedroom, 2.5-bath condominium has been meticulously transformed within the past five years into a showcase of contemporary elegance. GOURMET KITCHEN: Chef-inspired kitchen featuring gleaming quartz countertops, stainless

  Nikki Travaglino William Pitt Sotheby's Int'l

  80 Seaview Terrace Unit 31, Guilford, CT 06437
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  /34

  $499,900

  • 4 Beds
  • 2 Baths
  • 2,192 Sq Ft

  1281 Durham Rd, Madison, CT 06443

  Positioned in a highly desirable Madison location just minutes from town, shoreline beaches, and local shops, 1281 Durham Road delivers space, versatility, and opportunity on approximately half an acre. This property offers a flexible layout rarely found at this value point in the shoreline market. The main level showcases a generously sized living room centered around a fireplace, creating a

  Michelle Lorenzetti Premier Re Group LLC

  1281 Durham Rd, Madison, CT 06443
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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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  /32

  $850,000 Open Sat 12PM - 2PM

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

  46A Beach Ave, Madison, CT 06443

  Charming ranch set on a picturesque 0.92-acre property spanning from Beach Avenue to Pleasant View Avenue, with deeded beach access at the end of Beach Avenue. Originally built in the 1940s and thoughtfully renovated and expanded in 2001, this home blends classic character with comfortable living. The primary bedroom features windows that capture lovely views of the surrounding property, along

  Dana Weinstein Coldwell Banker Realty

  46A Beach Ave, Madison, CT 06443
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  /31

  $22,500

  • 490 Sq Ft

  379 Whitfield St Unit AN236, Guilford, CT 06437

  Absolutely gorgeous sunsets over the West River and an incredible view awaits you at The Guilford Yacht Club. Don't miss your opportunity to own a 36 foot boat slip in an excellent location on A Dock at a great price at the stunningly beautiful Guilford Yacht Club. Within 5 minutes of leaving your slip and the channel, you are already in Long Island Sound and on your way to your favorite

  Debbie Robinson Pearce Real Estate

  379 Whitfield St Unit AN236, Guilford, CT 06437
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  /4

  $22,000

  • 680 Sq Ft

  379 Whitfield St Unit BN2534, Guilford, CT 06437

  Guilford Yacht Club has been recently dredged to allow easy access to Long Island Sound. This Private club has a vibrant community of boaters waiting for you to join in on the fun. Just a few minutes and you are on the water making the best of your times with family and friends. Take advantage of the club pool and amenities. Pump out and fuel are nearby or on premises. Water, electricity and

  Rod Cross Coldwell Banker Realty

  379 Whitfield St Unit BN2534, Guilford, CT 06437
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  /39

  $2,375,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,517 Sq Ft

  132 Summer Hill Rd, Madison, CT 06443

  PRISTINE NEW CONSTRUCTION where thoughtful design meets high end craftsmanship. This newly built four-bedroom, four-and-a-half bathroom home offers the perfect blend of style and comfort. Inside, an open floor plan creates a seamless flow from room to room, anchored by a soaring two-story great room with a stunning gas fireplace. Large oversized doors spill out onto a 580 SF covered deck where

  Diane Dupont William Pitt Sotheby's Int'l

  132 Summer Hill Rd, Madison, CT 06443
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  /40

  $2,495,000

  • 3 Beds
  • 3.5 Baths
  • 3,306 Sq Ft

  61 Hartford Ave, Madison, CT 06443

  Own an architectural masterpiece with waterviews! Rarely is a Robert Page (AIA) designed coastal home available and this is one of his most compelling. A collaboration with master builders Baldwin and Baldwin and executed with precision, this 3300 sf home with three exterior decks, (including a "Skydeck"), unfolds over four levels. Finished in 2010, this 3(+) bedroom, 3.1 bath gem offers 3300

  Margaret Muir William Pitt Sotheby's Int'l

  61 Hartford Ave, Madison, CT 06443
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  /38

  $2,875,000

  • 5 Beds
  • 4.5 Baths
  • 6,319 Sq Ft

  37 Lantern Hill Rd, Madison, CT 06443

  An unbeatable location, 37 Lantern Hill is set in one of Madison's most desirable in-town neighborhoods. Close to sandy beaches, charming town center and the Madison Country Club, recreation and everyday conveniences are right at your doorstep. Traditional by design with ten foot ceilings, abundant natural light and generously scaled rooms that create an airy feel, ideal for relaxing or

  Margaret Muir William Pitt Sotheby's Int'l

  37 Lantern Hill Rd, Madison, CT 06443
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  /30

  $325,000

  • 0.5 Baths
  • 1,200 Sq Ft

  51 Mill Rd, Guilford, CT 06437

  This property would require a change-of-use from commercial to single-family for homeowners, buyer to do due diligence. Well-located antique commercial building overlooking the Guilford Mill Pond. The property features an approximately 1,200 SF ground-floor showroom with office space and restroom, currently operating as a tile showroom. Large windows provide excellent visibility and natural

  Tim Galvin William Raveis Real Estate

  51 Mill Rd, Guilford, CT 06437
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  /35

  $469,900

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  18 Saint Francis Woods Rd, Madison, CT 06443

  Spacious Split-level home with deck, open porch and patio overlooking large, level lot. Three levels of living space plus unfinished basement and partial attic for storage. Main level includes Living room, Dining room w/sliders to deck and Kitchen with all newer appliances. Upper level with 3 bedrooms and 2 full baths. Third level has Family room with fireplace and access to garage, patio and

  Christine Fappiano Shoreline Real Estate Company

  18 Saint Francis Woods Rd, Madison, CT 06443

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