Madison, CT Homes

• 

  Est $807,894 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,962 Sq Ft

  197 Dorset Ln, Madison, CT 06443

  197 Dorset Ln, Madison, CT 06443
• 

  

  

  /39

  $995,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 4,168 Sq Ft

  66 Beaver Pond Rd, Madison, CT 06443

  Spacious Colonial close to Town Center boasting unique first floor, handicap accessible, in-law apartment with separate entrance, full kitchen, large family room and bedroom suite. Main house embraces a renovated granite kitchen, 4 additional second floor bedrooms including primary suite and great room with fireplace. Floor plan is tailor made for large gatherings. The home's kitchen and

  John Campbell Compass Connecticut, LLC

  66 Beaver Pond Rd, Madison, CT 06443
• 

  $628,000 Sold Oct 24, 2025

  • 1,792 Sq Ft
  • $350/SF
  • 34 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1968

  338 Opening Hill Rd, Madison, CT 06443

  Extensively updated ranch offering effortless one-level living! This charming 4-bedroom, 2.5-bath home features many recent improvements, including a new roof with skylights, extensive landscaping, LeafGuard gutters, refinished floors, updated kitchen and bathrooms, garage doors, fresh paint, a new well tank and pump and more. Enjoy central air, a bonus three-season room (perfect office), fire

  Barbara Goetsch William Pitt Sotheby's Int'l

  338 Opening Hill Rd, Madison, CT 06443
• 

  Est $710,376 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft

  15 Bentwater Ln, Madison, CT 06443

  15 Bentwater Ln, Madison, CT 06443
• 

  

  

  /29

  $1,025,000 Under Contract

  • 5 Beds
  • 2.5 Baths
  • 3,136 Sq Ft

  148 Country Way, Madison, CT 06443

  Perched high on a hill at the end of a cul-de-sac, this one-of-a-kind home offers both privacy and elegance. Step into a dramatic two-story foyer, where a sparkling glass chandelier welcomes you into an open, airy layout. The flow of the home makes it easy to move from room to room-or step outside to enjoy the professionally landscaped grounds and in-ground saltwater pool. With nearly two acres

  Janet Peckinpaugh William Pitt Sotheby's Int'l

  148 Country Way, Madison, CT 06443
• 

  $690,000 Sold Oct 24, 2025

  • 3,999 Sq Ft
  • $173/SF
  • 30 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1991

  42 Buck Hill Rd, Madison, CT 06443

  This is the Madison home you have been waiting for!! Tucked away on 1.88 acres of level land in one of the area's most beautiful neighborhoods, this 4-bedroom colonial offers the perfect blend of privacy & convenience. Inside, natural light floods the home through skylights and oversized windows. The dramatic two-story entry opens to a bright living room with soaring ceilings, creating an

  Susan Santoro William Pitt Sotheby's Int'l

  42 Buck Hill Rd, Madison, CT 06443
• 

  Est $758,191 Not Listed For Sale

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

  67 Devonshire Ln, Madison, CT 06443

  67 Devonshire Ln, Madison, CT 06443
• 

  

  /24

  $499,900

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

  1281 Durham Rd, Madison, CT 06443

  Welcome to 1281 Durham Road in Madison, CT. This beautifully maintained home offers just under 2,200 sq ft of living space and sits on nearly half an acre in a highly desirable neighborhood. The main level features two bedrooms, a spacious living room with a fireplace, a large kitchen, a full bathroom, a laundry room, and a huge bonus room that extends the entire length of the house. The windows

  Danny Hernandez CLMA Realty

  1281 Durham Rd, Madison, CT 06443
• 

  $815,000 Sold Oct 23, 2025

  • 3,039 Sq Ft
  • $268/SF
  • 29 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1994

  72 Kelsey Springs Dr, Madison, CT 06443

  Welcome to 72 Kelsey Springs Dr in beautiful Madison, CT! This charming 4-bedroom, 2.5-bath colonial offers over 2,500 sq ft of living space with serene pond views and a peaceful 1-acre level lot in a sought-after neighborhood. Step inside to find a warm and inviting layout perfect for everyday living and entertaining. The spacious kitchen flows into a cozy family room, while the formal dining

  Nick Prevost William Raveis Real Estate

  72 Kelsey Springs Dr, Madison, CT 06443
• 

  Est $577,940 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,354 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /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
• 

  $560,000 Sold Oct 20, 2025

  • 784 Sq Ft
  • $714/SF
  • 25 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1920

  24 Pent Rd, Madison, CT 06443

  Fulfill your dream of having a beach cottage just steps to one of Madison's finest beaches. This precious little home has been loved by the same family for decades and now it is ready for someone new to cherish. With one bedroom and bathroom on the main floor and finished attic space for overflow guests, you won't want to be anywhere else during summer months. You may access the Shoreline

  Julie Ovian William Pitt Sotheby's Int'l

  24 Pent Rd, Madison, CT 06443
• 

  Est $599,746 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,928 Sq Ft

  1956 Durham Rd, Madison, CT 06443

  1956 Durham Rd, Madison, CT 06443
• 

  

  /40

  $600,000

  • 3 Beds
  • 2.5 Baths
  • 2,542 Sq Ft

  25 Copperstone Ln, Madison, CT 06443

  Welcome home to this charming 3-bedroom Cape-style Colonial, perfectly set back on a peaceful cul-de-sac. Offering over 2,500 sq ft of living space, this home blends warmth, functionality, and privacy, complete with a sparkling in-ground pool and stamped concrete patio that create a true backyard retreat. Step inside to a bright, open main level featuring a spacious kitchen with wraparound

  Nicholas Tarquino Carbutti & Co., Realtors

  25 Copperstone Ln, Madison, CT 06443
• 

  $745,000 Sold Oct 20, 2025

  • 2,564 Sq Ft
  • $291/SF
  • 72 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1975

  23 Forest Hills Dr, Madison, CT 06443

  Welcome to this classic 5-bedroom Colonial on highly sought-after Forest Hills Drive. This beautifully maintained home offers 5 spacious bedrooms and 3.5 baths, including a finished walkout lower level with a game room, guest bedroom, and full bath-perfect for entertaining or hosting overnight guests. The heart of the home is a newly renovated kitchen featuring quartz countertops, stainless steel

  Cathy Lynch Coldwell Banker Realty

  23 Forest Hills Dr, Madison, CT 06443
• 

  Est $705,042 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,323 Sq Ft

  25 Summit Ln, Madison, CT 06443

  25 Summit Ln, Madison, CT 06443
• 

  

  /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
• 

  $530,000 Sold Oct 17, 2025

  • 2,159 Sq Ft
  • $245/SF
  • 83 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  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
• 

  Est $760,287 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,614 Sq Ft

  272 County Rd, Madison, CT 06443

  272 County Rd, Madison, CT 06443
• 

  

  /40

  $825,000

  • 3 Beds
  • 4 Baths
  • 2,160 Sq Ft

  3 Arrowhead Rd, Madison, CT 06443

  Embrace the enchantment of Shoreline Living at its finest with this sun-drenched haven at 3 Arrowhead, a jewel nestled in a quaint community with the river at your doorstep. As you step into this radiant abode, you're welcomed by a symphony of natural light and the serene melodies of local birdsong. The home's design harmoniously blends the outdoors with the indoors, creating a tranquil retreat.

  Diana Hartman William Pitt Sotheby's Int'l

  3 Arrowhead Rd, Madison, CT 06443
• 

  $130,000 Sold Oct 17, 2025

  • 476 Sq Ft
  • $273/SF
  • 124 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1940

  16 North St, Madison, CT 06443

  If you're dreaming of summers by the shoreline, this charming cottage in Dud's Village, Madison, offers the perfect seasonal escape. Less than a mile from Hammonasset Beach State Park-Connecticut's largest shoreline park-this move-in-ready cottage offers easy access to two miles of sandy beaches, scenic walking and biking paths, and endless outdoor activities. A private path from the village

  Margaret Curry William Raveis Real Estate

  16 North St, Madison, CT 06443
• 

  Est $640,969 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  237 County Rd, Madison, CT 06443

  237 County Rd, Madison, CT 06443
• 

  

  /40

  $435,000

  • 2 Beds
  • 1.5 Baths
  • 1,110 Sq Ft

  779 Summer Hill Rd, Madison, CT 06443

  Welcome home to this picture-perfect ranch in peaceful North Madison-where comfort, charm, and convenience come together beautifully. With just over 1,100 square feet of thoughtfully designed living space, this home offers two bedrooms plus flexible office space, ideal for working from home or creating a cozy guest space. The open floor plan fills the home with natural light and makes everyday

  Diane Devries William Pitt Sotheby's Int'l

  779 Summer Hill Rd, Madison, CT 06443
• 

  $144,000 Sold Oct 10, 2025

  • 630 Sq Ft
  • $229/SF
  • 70 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1940

  33 North St, Madison, CT 06443

  Charming Seasonal Cottage in Madison, CT - Steps from the Beach! Welcome to your perfect summer getaway! This cozy and comfortable seasonal cottage offers 629 square feet of well-utilized living space in a family and pet-friendly community, just a short stroll from Hammonasset Beach, a scenic salt pond, and the Hammonasset River. Tucked away in one of Madison's most desirable cottage villages,

  Joe Rodorigo Keystone Realty, LLC

  33 North St, Madison, CT 06443
• 

  Est $738,877 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,954 Sq Ft

  31 Lakewood Dr, Madison, CT 06443

  31 Lakewood Dr, Madison, CT 06443
• 

  

  /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 Complete Real Estate

  174 Concord Dr, Madison, CT 06443
• 

  $1,200,000 Sold Oct 09, 2025

  • 1,580 Sq Ft
  • $759/SF
  • 11 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1930

  110 E Wharf Rd, Madison, CT 06443

  Steps to the Shoreline - Four-Bedroom Beach Retreat with Deeded Beach Right Away! Tucked away on a serene interior lot in Madison's coveted East Wharf neighborhood, this four-bedroom, two-bath coastal gem blends timeless seaside charm with modern comfort-plus valuable income-producing potential. With a deeded beach right away, your days can begin and end just steps from a sandy, private,

  Lisa Daniele William Raveis Real Estate

  110 E Wharf Rd, Madison, CT 06443
• 

  Est $767,780 Not Listed For Sale

  • 6 Beds
  • 3.5 Baths
  • 3,146 Sq Ft

  35 Lakewood Dr, Madison, CT 06443

  35 Lakewood Dr, Madison, CT 06443
• 

  

  /34

  $690,000

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

  39 Stepping Stone Ln, Madison, CT 06443

  Classic Madison Colonial with Pool, Privacy and Expansion Potential Set back from the road at the end of a small cul-de-sac, this inviting 3-bedroom, 2.5-bath Colonial offers privacy, space, and flexible living options. Originally a 4-bedroom home, it can easily be converted back since the fourth bedroom was transformed into a large dressing room connected to the primary bedroom. The two

  Cindy Breckheimer Forever Homes Real Estate LLC

  39 Stepping Stone Ln, Madison, CT 06443
• 

  $726,200 Sold Oct 08, 2025

  • 1,296 Sq Ft
  • $560/SF
  • 140 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1925

  11 Pent Rd, Madison, CT 06443

  LOCATION!!! One of Madison's most desirable beach neighborhoods awaits you. This charming beach community home has it's own separate cottage! Walk to the beautiful beach or the popular "Greenway Trail" that leads into Hammonasset State Park. Enjoy swimming, paddle boarding, kayaking or just relaxing in the warm Summer sun. The main house boasts a first floor full bath, kitchen, dining area,

  Maggie Bartels Coldwell Banker Realty

  11 Pent Rd, Madison, CT 06443
• 

  Est $866,899 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,025 Sq Ft

  235 Devonshire Ln, Madison, CT 06443

  235 Devonshire Ln, Madison, CT 06443
• 

  

  /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
• 

  $537,500 Sold Oct 07, 2025

  • 1,864 Sq Ft
  • $288/SF
  • 14 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1967

  40 Green Acres Dr, Madison, CT 06443

  Welcome to 40 Green Acres Drive, an adorable home on a side street located close to all Madison and Guilford amenities, including the beach! This adorable split level has been lovingly maintained through the years by only the second owner with many updates and great features! The perfectly flat .39 acre lot features mature landscaping, privacy trees and the home has a brand new trex deck and sun

  Andrea Viscuso Compass Connecticut, LLC

  40 Green Acres Dr, Madison, CT 06443
• 

  Est $605,201 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,177 Sq Ft

  1659 Durham Rd, Madison, CT 06443

  1659 Durham Rd, Madison, CT 06443
• 

  

  /40

  $3,795,000

  • 4 Beds
  • 5 Baths
  • 4,505 Sq Ft

  98 Island Ave, Madison, CT 06443

  Welcome to 98 Island Avenue in Madison, a stunning coastal residence just a short walk to the beach and town. Custom built in 2016 w/extraordinary attention to detail, this home combines timeless elegance with modern convenience. Inside, you'll find soaring 9-foot ceilings, 8-foot doors, hurricane-rated Andersen windows, & polished nickel Baldwin hardware throughout. The chef's kitchen is a

  Susan Clifford Coldwell Banker Realty

  98 Island Ave, Madison, CT 06443
• 

  $850,000 Sold Oct 06, 2025

  • 3,464 Sq Ft
  • $245/SF
  • 65 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1973

  241 Hunters Trail, Madison, CT 06443

  Tucked away in one of Madison's most desirable subdivisions, this spacious 4-bedroom, 3.5-bath colonial offers the perfect blend of function, flow, and comfort-just minutes to downtown, beaches, the highway, and medical facilities. The heart of the home is the warm and inviting kitchen, complete with rich cherry cabinets, an oversized island, ample storage, and generous counter space-designed for

  Heidi DeRusso Coldwell Banker Realty

  241 Hunters Trail, Madison, CT 06443
• 

  Est $631,184 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,404 Sq Ft

  640 Summer Hill Rd, Madison, CT 06443

  640 Summer Hill Rd, Madison, CT 06443
• 

  

  /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
• 

  $2,600,000 Sold Oct 06, 2025

  • 3,397 Sq Ft
  • $765/SF
  • 81 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 1928

  25 Seaview Ave, Madison, CT 06443

  Unique, custom, architecturally designed home in the desirable Seaview Beach area. Situated on a high point of Seaview Ave on a corner lot, with deeded access rights to Long Island Sound. The sandy beach is accessed by a dedicated waterway with cabana. Perfect for a second or summer home, as well as a primary residence. This home was entirely rebuilt in 2010 and boasts numerous amenities &

  Alison Gould Gould Group LLC

  25 Seaview Ave, Madison, CT 06443
• 

  Est $597,757 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,052 Sq Ft

  69 Mendingwall Cir, Madison, CT 06443

  69 Mendingwall Cir, Madison, CT 06443

Showing Results 81 - 120, Page 3 of 18