Homes for Sale near The Country School

• 

  

  

  /37

  $3,100,000

  • 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
• 

  

  

  /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
• 

  

  

  /15

  $750,000

  • Land
  • 1.00 Acre
  • $750,000 per Acre

  00 Stone Rd, Madison, CT 06443

  Discover the perfect opportunity to build your dream home on this exceptional buildable lot, offering coveted deeded beach rights. Nestled in a prime location, this property provides direct access to pristine Madison shore, allowing you to enjoy the beauty of coastal living every day. Whether you're looking to create a private retreat, or a vacation/second home, this lot offers unlimited

  

  Betsy Anderson

  William Pitt Sotheby's Int'l

  (475) 472-9564

  00 Stone Rd, Madison, CT 06443
• 

  

  

  /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
• 

  

  

  /40

  $3,350,000

  • 6 Beds
  • 6 Baths
  • 8,097 Sq Ft

  37 Lantern Hill Rd, Madison, CT 06443

  Experience the perfect combination of luxury and convenience with this exceptional 8,000-square-foot home, ideally situated within walking distance of the beaches, town center, and Madison Country Club. Nestled in the sought-after Lantern Hill neighborhood, this premier residence is surrounded by brick sidewalks and charming lanterns that evoke timeless elegance and in-town living at its finest.

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 252-4695

  37 Lantern Hill Rd, Madison, CT 06443
• 

  

  /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
• 

  

  /3

  $1,150,000 Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 3,792 Sq Ft

  59 Copperfield Dr, Madison, CT 06443

  Graciously Remodeled Colonial located in a highly desirable neighborhood at the end of a peaceful cul-de-sac, this beautifully remodeled 4-bedroom colonial offers timeless charm with modern updates. Step into a welcoming two-story foyer that opens to a sunlit, open-concept layout with soaring cathedral ceilings-perfect for entertaining. The remodeled kitchen flows seamlessly into the family room,

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 244-6745

  59 Copperfield Dr, Madison, CT 06443
• 

  

  /40

  $850,000

  • 3 Beds
  • 2.5 Baths
  • 3,488 Sq Ft

  31 Christopher Ln, Guilford, CT 06437

  Tucked into a quiet, picturesque cul-de-sac, this beautifully maintained colonial radiates timeless charm and effortless grace. From the moment you arrive, its regal presence, inviting curb appeal, and welcoming atmosphere create just the right feeling-making a lasting impression and instantly putting you at ease. Centrally located and thoughtfully designed for both lively entertaining and

  Nicole White William Raveis Real Estate

  31 Christopher Ln, Guilford, CT 06437
• 

  

  /40

  $779,900

  • 5 Beds
  • 3.5 Baths
  • 3,892 Sq Ft

  94 Sportsman Hill Rd, Madison, CT 06443

  Welcome to 94 Sportsman Hill Road! Nestled on a 1.66-acre lot on a quiet cul-de-sac, this newly renovated colonial offers over 3,800 sq ft of versatile living space with 5 bedrooms, 3.5 bathrooms, a family room, an entertainment room, and more. Step inside to a bright center hall with a neutral palette and gleaming hardwood floors throughout. The kitchen features a center island with storage and

  Alejandro Pabon-Rey Dow Della Valle

  94 Sportsman Hill Rd, Madison, CT 06443
• 

  

  /35

  $1,250,000

  • 4 Beds
  • 2.5 Baths
  • 2,310 Sq Ft

  50 Oak Ave, Madison, CT 06443

  "The beach is calling, and I must go". Located on a quiet, private, street with views of the Long Island Sound. This beautiful home was designed by one Madison's own well respected architects Duo Dickinson. Architectual design was implemented by custom builder Calvin Page and later modified by Matthew Fogarty. The site plan was created by Waldo and Associates. A lot of expertise and experience

  Heather Clinton Berkshire Hathaway NE Prop.

  50 Oak Ave, Madison, CT 06443
• 

  

  /40

  $1,395,000

  • 3 Beds
  • 2.5 Baths
  • 2,538 Sq Ft

  908 Boston Post Rd, Madison, CT 06443

  THE GENERAL'S RESIDENCES at Fence Creek, the perfect & rare combination of location, luxury & comfort in the heart of charming small town Madison w/ it's nationally recognized independent R J Julia Booksellers, 2 screens Madison Arts Cinema, specialty shops & numerous fine dining establishments. There is a glorious & sandy Town Beach for residents only literally just a walk down the street w/ not

  Todd Gould William Pitt Sotheby's Int'l

  908 Boston Post Rd, Madison, CT 06443
• 

  

  /31

  $999,999

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

  15 Briarwood Dr, Guilford, CT 06437

  Located in a beautiful Guilford neighborhood, no through road, this exceptional home offers a vacation inspired lifestyle with a pool and sauna inside, and a 5-mile drive to the beach! Many thoughtful improvements throughout the spacious flexible layout, with the opportunity to still make it your own. Major systems have been updated, including the septic, central air, hot water tank, electrical,

  Melanie Taylor Berkshire Hathaway NE Prop.

  15 Briarwood Dr, Guilford, CT 06437
• 

  

  /28

  $1,050,000

  • 2 Beds
  • 2.5 Baths
  • 2,418 Sq Ft

  5 Evarts Ln, Madison, CT 06443

  Nestled in the heart of downtown Madison, this stunning townhouse with a freshly painted interior offers the perfect blend of luxury and convenience-just a short stroll from sandy beaches, the library, a cinema, a charming independent bookstore, and an array of shops and restaurants. The beautifully designed kitchen boasts soaring 9'+ ceilings, a SubZero refrigerator, and an inviting eat-in space

  Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

  5 Evarts Ln, Madison, CT 06443
• 

  

  /40

  $889,900

  • 4 Beds
  • 2.5 Baths
  • 2,882 Sq Ft

  387 N River St, Guilford, CT 06437

  Charming Historic Home built for Peter Chapman in 1851 by William Weld according to Keeping Society (town has different date). Currently has renovations throughout providing inviting elegance and modern conveniences. Main level renovated to include main level BR with ADA compliant full bath, new enlarged upgraded kitchen w/SS appliances, quartz counter and nearby wet bar area adjacent to den with

  Diane Beckwith Popolizio William Raveis Real Estate

  387 N River St, Guilford, CT 06437
• 

  

  /40

  $925,000

  • 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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  /33

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 3,232 Sq Ft

  141 Meadow Ridge Ln, Guilford, CT 06437

  WOW! This stunning contemporary colonial is bathed in sunlight and packed with incredible features from top to bottom. Step into the dramatic new two-story entry and be amazed. The huge family room boasts beamed cathedral ceilings, skylights, a cozy fireplace, and an abundance of windows. Gleaming hardwood floors flow throughout, leading to a banquet-sized dining room perfect for hosting. The

  Susan Santoro William Pitt Sotheby's Int'l

  141 Meadow Ridge Ln, Guilford, CT 06437
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  /27

  $1,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,435 Sq Ft

  675 Durham Rd, Madison, CT 06443

  Stunning 4-Bedroom 3 1/2bathroom cape perfectly situated in Madison for convenience and privacy. This home offers both comfort and elegance in every corner with its open floor plan and top of the line kitchen and baths. Enjoy the ease of a private primary suite on the main floor, complete with a massive walk-in shower and plenty of storage space. This open floor plan offers endless possibilities

  Meig Walz Newcomb Coldwell Banker Realty

  675 Durham Rd, Madison, CT 06443
• 

  

  /39

  $1,950,000

  • 3 Beds
  • 2.5 Baths
  • 2,194 Sq Ft

  66 High St Unit 36, Guilford, CT 06437

  66 HIGH STREET - 3 bedroom, 2.5-bath condominium, boasting an impressive 2,194 SF on the 2nd floor. The views are western exposure, of marsh and Long Island Sound. Located in the prestigious community of Guilford, CT, this residence offers a harmonious blend of modern design and natural beauty. The open concept includes a sun filled Living Room, with a cozy gas fireplace, Dining Room and Kitchen,

  Kirsten Adams William Pitt Sotheby's Int'l

  66 High St Unit 36, Guilford, CT 06437
• 

  

  /38

  $885,000

  • 4 Beds
  • 3.5 Baths
  • 3,625 Sq Ft

  765 Durham Rd, Guilford, CT 06437

  Nestled on a spacious and serene .92-acre lot, this fully renovated 4-bedroom, 3.5-bath contemporary home has the perfect blend of modern design and functional living. The thoughtfully designed layout features a luxurious primary suite on the main level, ideal for convenience and privacy. Upstairs, discover a second primary suite, complete with its own private balcony, providing a peaceful

  Adam Negri Venus and Mars Properties, LLC

  765 Durham Rd, Guilford, CT 06437
• 

  

  /31

  $935,000

  • 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
• 

  

  /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
• 

  

  /35

  $499,999

  • 3 Beds
  • 1.5 Baths
  • 1,541 Sq Ft

  567 Nut Plains Rd, Guilford, CT 06437

  Tucked away in the scenic town of Guilford, 567 Nut Plains Road is a perfect blend of classic New England charm and modern updates. This beautifully maintained 1941 home sits on a 0.22-acre corner lot and offers 3-4 bedrooms, 1.5 bathrooms, and a detached garage. Step inside to a bright and inviting living room, complete with a cozy fireplace and an abundance of natural light streaming through

  Lauren Freedman Coldwell Banker Realty

  567 Nut Plains Rd, Guilford, CT 06437
• 

  

  /35

  $369,900

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

  16 Copper Hill Dr, Guilford, CT 06437

  Move right in to your own free-standing Cape Cod style condo without even picking up a paint brush. This home has been completely remodeled from top to bottom with high-end flooring, bathroom fixtures, appliances, kitchen cabinets and countertops, bathrooms, exterior and interior doors and more. It is located on a cul-de-sac of three homes in Copper Hill Village and is only a short distance from

  Doris Fallon William Raveis Real Estate

  16 Copper Hill Dr, Guilford, CT 06437
• 

  

  /25

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,125 Sq Ft

  55 Woodland Rd, Madison, CT 06443

  Bright, fully renovated, one-story home within walking distance to Madison Town Green. New kitchen, baths, floors, roof, and heater! Three bedrooms. Two full baths. Full basement.

  Pam Kadamus William Pitt Sotheby's Int'l

  55 Woodland Rd, Madison, CT 06443
• 

  

  /40

  $640,000

  • 4 Beds
  • 2.5 Baths
  • 2,081 Sq Ft

  231 Whitethorn Dr, Guilford, CT 06437

  Multiple offers have been received- Highest & Best due by Wednesday 5/7 5:00. This sun-filled 4 bedroom home offers charming details throughout & a magical backyard bordering the Guilford Land Trust & Timberland trails. The sunfilled living room, currently being used as a home office, offers built-ins & a large picture window.Through the french doors is found the dining room w/ access to the

  Sue Knapp William Pitt Sotheby's Int'l

  231 Whitethorn Dr, Guilford, CT 06437
• 

  

  /27

  $615,000

  • 2 Beds
  • 3 Baths
  • 1,680 Sq Ft

  11 Strathmore Ln, Madison, CT 06443

  Meticulously maintained townhouse condo now available. Two bedrooms (office serving as a 3rd bedroom) bright & sunny kitchen, combined living & dining room, family room w/sliders out to private patio, one car attached garage w/additional parking. Savor the best of indoor and outdoor living minutes to beaches, restaurants, world famous RJ Julia Bookstore, library, train and commuter routes. Just

  Pam Kadamus William Pitt Sotheby's Int'l

  11 Strathmore Ln, Madison, CT 06443
• 

  

  /40

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,027 Sq Ft

  197 Meadow Hills Dr, Guilford, CT 06437

  Lake Community Living at Meadow Hills! Welcome to 197 Meadow Hills, a beautifully maintained home tucked within a charming subdivision offering lake and beach access. Lovingly cared for, this home blends comfort, convenience, and stylish updates throughout. Open Concept Living: The main floor features 3 bedrooms, a full bathroom, and a spacious kitchen/dining/living room - perfect for gatherings

  Melissa DiPiazza RE/MAX One

  197 Meadow Hills Dr, Guilford, CT 06437
• 

  

  /40

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 1,986 Sq Ft

  81 Colonial Rd, Madison, CT 06443

  Move right in to this beautifully renovated 4-bedroom, 2.5-bath Saltbox Colonial offering over 2,600 sq. ft. of stylish living space, just minutes from town and beaches. Set on 1.63 lightly wooded acres, the property backs up to land trust and 33 acres of Cockaponsett State Forest, with seasonal views of Madison Lakes to the east. Designer touches throughout include walnut-stained wide board

  Willard Finkle Coldwell Banker Realty

  81 Colonial Rd, Madison, CT 06443
• 

  

  /39

  $575,000

  • 2 Beds
  • 2 Baths
  • 1,374 Sq Ft

  46 Legend Hill Rd, Madison, CT 06443

  Highly coveted ranch style end unit in Legend Hill with partial ocean views. Vaulted ceilings, bright light throughout, a finished walkout basement and brand new carpet make this unit a must-see! The sun-drenched 3 season room boasts bucolic views. Features of the community include a large in-ground pool with a community gathering historic clubhouse with patios, terraces & professionally

  Meg Farmer Coldwell Banker Choice Properties

  46 Legend Hill Rd, Madison, CT 06443
• 

  

  /40

  $749,900

  • 4 Beds
  • 3 Baths
  • 3,037 Sq Ft

  76 Horse Pond Rd, Madison, CT 06443

  This spacious Cape-style home with a modern twist offers over 3,000 sq ft of thoughtfully designed living space-plus an additional 300 sq ft finished rec room in the basement. The heart of the home is the expansive kitchen, featuring granite countertops, a center island with a built-in microwave drawer, and premium stainless steel appliances including a Wolf 6-burner dual fuel range, Viking

  James Didato Berkshire Hathaway NE Prop.

  76 Horse Pond Rd, Madison, CT 06443
• 

  

  /40

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,027 Sq Ft

  182 Durham Rd, Madison, CT 06443

  Welcome to this beautifully maintained 4-bedroom, 2-bathroom home that blends comfort, style, and thoughtful upgrades. Inside, you'll find a spacious living area with eye-catching exposed wood beams, and an updated kitchen featuring modern finishes and appliances-perfect for everyday living and entertaining. This home is move-in ready with key updates including a new well pump, a new pool filter

  Timothy Johnson KW Legacy Partners

  182 Durham Rd, Madison, CT 06443
• 

  

  /25

  $454,000

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

  42 Lake Dr, Madison, CT 06443

  Charming 4-Bedroom Colonial in Serene Neighborhood Setting Step into timeless colonial charm with this spacious 4-bedroom, 2.5-bath home, nestled in a peaceful neighborhood surrounded by nature. Inside, you'll find wide plank hardwood floors in the living room, complemented by a cozy fireplace-perfect for relaxing evenings. The main level offers the convenience of a laundry room and a layout

  Roberta Whalen LAER Realty Partners

  42 Lake Dr, Madison, CT 06443
• 

  

  /38

  $459,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  46 Sperry Dr, Guilford, CT 06437

  Beautifully Renovated 3-Bedroom Home in Guilford, CT - Move-In Ready! Welcome to this stunning, fully renovated single-family home located in the desirable shoreline town of Guilford. Boasting 2 spacious bedrooms, 1 full bathroom, and an additional room that can be used as your home office. This charming property has been completely updated in 2025 with modern finishes and high-quality

  Christopher Wihbey Dave Jones Realty, LLC

  46 Sperry Dr, Guilford, CT 06437
• 

  

  /21

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,125 Sq Ft

  24 Echo Point Rd, Guilford, CT 06437

  This waterfront home offers beautiful lake views, stunning stone work and terraces throughout the property. It has 3 bedrooms and two and half baths with a 2 car garage. There is a fire pit with built in stone seating overlooking the water with a private dock. The large deck off the garage is another spectacular area with sweeping views of the water. The living room offers a wall of windows with

  Susan Fair Fair Realty

  24 Echo Point Rd, Guilford, CT 06437
• 

  

  /40

  $2,300,000

  • 5 Beds
  • 6 Baths
  • 5,795 Sq Ft

  584 Boston Post Rd, Madison, CT 06443

  Elegant European-Style home in the Heart of Madison. A perfect blend of luxury, privacy, and convenience in this remarkable 4,700+ sq ft home, ideally located just steps from the Madison Town Green, downtown shops, and stunning beaches. This five-bedroom home offers a host of exceptional features. Step through the front door into a dramatic two-story great room with an open floor plan, bathed in

  Kate Jasko Coldwell Banker Realty

  584 Boston Post Rd, Madison, CT 06443
• 

  

  /40

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 1,866 Sq Ft

  84 Roast Meat Hill Rd, Killingworth, CT 06419

  The warmth and character of this beautifully preserved circa 1860 antique home, located on one of Killingworth's most storied roads, will surprise and please you! Set on a picturesque and level 2-acre lot, this 3-bedroom, 2.5-bath farmhouse was tastefully expanded by the master craftsman Drexel Frye in the late 80's, who perfectly blended historic charm with comfort that is still appreciated in

  Shelly Cumpstone Coldwell Banker Realty

  84 Roast Meat Hill Rd, Killingworth, CT 06419
• 

  

  /40

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  259 Weatherly Trail, Guilford, CT 06437

  Set on a peaceful and private 1.36-acre lot, this Contemporary Colonial home offers comfort, style, and a connection to nature. As you enter, you'll notice the home's open layout and soaring vaulted ceilings that create a bright and airy feel. The spacious living room includes beautiful hardwood floors, a pellet stove for cozy winter nights, and sliding doors that lead to a wraparound deck -

  Daniel Lussier eXp Realty

  259 Weatherly Trail, Guilford, CT 06437
• 

  

  /40

  $2,900,000

  • 5 Beds
  • 4 Baths
  • 3,397 Sq Ft

  25 Seaview Ave, Madison, CT 06443

  Stunning, custom architectural designed home in the desirable Seaview Beach area. Situated on the high point of Seaview Ave on a corner lot, with deeded access rights to Long Island Sound & sandy beach by a dedicated waterway with cabana. This home was entirely rebuilt in 2010 and boasts numerous amenities, including custom woodworking, built-ins and cabinetry throughout, automated skylights,

  Alison Gould Gould Group LLC

  25 Seaview Ave, Madison, CT 06443
• 

  

  /38

  $649,900

  • 2 Beds
  • 1 Bath
  • 1,369 Sq Ft

  7 Meadow Ln, Madison, CT 06443

  "The River House" -serene vistas of the river and marsh from most every room in this precious, year round ranch. Brand new engineered septic w/1000 gal tank & roof are major improvements. Large windows bring the outside in where you can enjoy the abundant wildlife that thrives here. Meandering Neck River leads you to Long Island Sound; tidal in nature but allows for a shallow-bottom boat, kayak

  Amy Kirst William Pitt Sotheby's Int'l

  7 Meadow Ln, Madison, CT 06443
• 

  

  /6

  $2,000,000

  • 7 Beds
  • 7 Baths
  • 5,547 Sq Ft

  675 & 677 Durham Rd, Madison, CT 06443

  Your private estate awaits. This is the price for both the white cape built in 2020 and the gray home built in 2023. Absolutely stunning and meticulously maintained, these beautiful homes have an open and airy feel. Walk in and you immediately notice the exceptional quality of both homes. The main home is complete with a first-floor primary suite and spacious upstairs. The guest home is open

  Meig Walz Newcomb Coldwell Banker Realty

  675 & 677 Durham Rd, Madison, CT 06443

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