Refine Search
Map
Sort by
$1,975,000
2 Baths ⋅ 24163885 MLS
15+ Acres of Potential Subdivision of 2-6 lots 9 minutes to Town. Extensive Surveys have been done, including wetlands mapping. Check with Steve for details. Included in price is a 4 bedroom 2 full bath Cape on 15+ acres with an extensive renovation including an updated kitchen attached to the cathedral ceiling family room addition featuring expansive views of 2 spring fed, stocked ponds, below the home. New Baths and windows throughout along refinished wide-board floors in the original structure. New paint and trim throughout along with a traditional family room with full fireplace in the walk-out basement with garage access. Residence is listed as MLS #24163897

441 Opening Hill Rd, Madison
$1,975,000
4 Beds ⋅ 2 Baths ⋅ 24163897 MLS
Updated 4 bedroom 2 Full bath Cape on 15+ Acres of rolling Meadows and woods bordering State Forest and over 800 feet of frontage on Opening Hill. Extensive updating includes new windows and doors, original wide-board refinishing in the original building. A new kitchen in the cathedral ceilinged family room addition with deck that commands beautiful views of two spring fed, stocked ponds below the home. Just updated with New Doors and Windows and 2 full baths. A traditional paneled downstairs family room with wood burning fireplace offers direct access to the basement and under house double length garage.

441 Opening Hill Rd, Madison
$1,250,000
3 Beds ⋅ 2 Baths ⋅ 24200298 MLS
PERFECT LOCATION AND MOVE IN READY. Discover the charm of this natural light filled renovated 3 bedroom / 2 full bath home, single-family dwelling. This home is perfect for those seeking comfort, space, and a welcoming atmosphere. The property boasts an inviting open concept layout on the 1st floor, with a dynamic Kitchen (vaulted ceilings!), loads of popular shiplap on the walls - ample room to make lasting memories! Situated on a lovely full fenced in lot, this home is 1/2 block from the East Wharf Beach but also provides easy walkability to downtown Madison. The backyard hosts a finished shed (storage? office?) and an outdoor patio for additional entertaining. This home provides a wonderful balance of indoor and outdoor living. Perfect condition!

99 E Wharf Rd, Madison
$880,000
2 Beds ⋅ 2 Baths ⋅ 24183654 MLS
Turn down a long, picturesque driveway to a stunning mid-century cape, unseen from the roadway. Note, the spectacular fieldstone chimney on the large addition of the gable-end plus the closed in screened porch to the west. Ahead you'll find a large, detached 2-car garage and off to the south a small barn with great potential for an equestrian opportunity. From the screened in porch, enter the house thru its French doors. The field stone fireplace is a match to the exterior chimney. The semi-circular staircase rises to an upstairs reading room with its own fireplace and just off the primary bedroom. Both the reading room and bedroom enjoy the added light of angle-mounted skylights. Walking to the south, you'll pass the upstairs full bath, a second staircase, another full bedroom, and a study at the end of the hall. Take the traditional staircase back to the first floor and step into the foyer by the front door. Turn either left into a large, fully-equipped eat-in kitchen or turn right into a magnificent full-width dining room with a large, central fireplace with multiple windows on 3 sides over-looking the estate's grounds. Walk outside the house and turn to the west to see the well-maintained rolling acres before you. This is a lovely, well cared for private home on a very beautiful 7+ acre lot.

2415 Durham Rd, Madison
$699,000
4 Beds ⋅ 2 Baths ⋅ 24198873 MLS
Welcome to 38 Church Lane, where exceptional custom renovations meet a captivating Madison setting. Perched high on a large corner lot surrounded by mature trees, this thoughtfully updated 4-bedroom, 2.5 bath home offers sophisticated finishes, a flexible floor plan ideal for multi-generational living and privacy just minutes from Madison's town center and shoreline. The stunning kitchen, custom-crafted by Gedney Kitchens, features bespoke cabinetry and premium finishes, while an oversized fireplace anchors the inviting living room. The finished lower level includes a comfortable den with Vermont Castings wood-burning stove, custom Gedney wet bar, light-filled bedroom/office, and spa-inspired renovated bath with dual-head shower, heated floors, and heated towel rack. Outside, a brand-new composite deck overlooks terraced grounds with mature trees, stonework, curved pathways, and inviting spaces to garden, gather, and explore. An existing front-yard pond scape offers intriguing possibilities for future re-imagining. Hardie board siding with AZEK trim provides a remarkably low-maintenance exterior, complemented by energy-efficient windows and central air. Minutes from Madison's shops, dining, and beautiful shoreline beaches, this one-of-a-kind property truly must be experienced in person.

38 Church Ln, Madison
$649,000
4 Beds ⋅ 2 Baths ⋅ 24191346 MLS
Charming Colonial in a central location just minutes from downtown, beautiful town beaches, schools, and with easy access to major highways. Brimming with character and timeless appeal, this home offers a wonderful layout for both everyday living and entertaining. The welcoming family room, featuring a gas fireplace and vaulted ceiling, serves as the heart of the home and flows seamlessly into the kitchen and sunroom. The charming kitchen offers a center island and opens to the dining area, allowing the cook to stay connected with family and guests. A spacious front-to-back living room provides an additional inviting space to relax or entertain. Upstairs, you'll find four bedrooms, including a comfortable primary bedroom, along with a full bath. The full unfinished basement offers laundry, abundant storage, and potential for future expansion. Filled with natural light, the sunroom is the perfect spot to enjoy your morning coffee or unwind while taking in views of the backyard. Step outside to a private deck with plenty of room for outdoor dining and gatherings. The generous backyard offers ample space for a game of catch, a playset, or simply enjoying the outdoors. Come home and enjoy everything Madison has to offer.

496 Green Hill Rd, Madison
$595,000
2 Beds ⋅ 2 Baths ⋅ 24160683 MLS ⋅ Windermere East BLDG.
Nestled in the highly sought-after Windermere East community, this rare free-standing condo offers the perfect blend of privacy, comfort, and coastal charm in beautiful Madison. Enjoy serene river views and a peaceful setting just moments from the shoreline. This well-maintained home features 2 bedrooms and 2 full baths, a spacious fireplaced living room, and a bright kitchen ideal for everyday living. The new HVAC system with gas heat and central air ensures year-round comfort and efficiency. A lovely 3-season sunroom that offers additional living space and opens to a private patio-perfect for relaxing, entertaining and enjoying the view of the river. Ideal for kayaking right from your backyard, with space to conveniently store your kayak onsite. A standout feature of this unit is the full basement-an uncommon find in the complex-offering abundant storage, a cedar closet, and partially finished space with endless possibilities. Ideally located within walking distance to Hammonasset Beach State Park and scenic walking trails, and just minutes to marina's and downtown Madison where you'll find fine dining, a charming movie theater, shops and the beloved RJ Julia Booksellers. Enjoy the best of shoreline living in one of Madison's most desirable communities-an ideal choice for those looking to downsize or create the perfect coastal escape.

10 Runnymede Ln Unit 10, Madison
$565,000
2 Beds ⋅ 2 Baths ⋅ 24178656 MLS ⋅ Kensington Acres South BLDG.
Experience true WIDE OPEN SPACES in highly sought-after Kensington Acres South! With condos, it is all about LOCATION. This desirable completely detached standalone Ranch is not attached along the corners like some other units. Flooded w/ bright natural light, the home boasts peaceful, expansive lawn views from your private enclosed Sun Room, a perfect spot for morning coffee. A flat, level & straight front walkway provides seamless access to your nearby detached garage and parking. Meticulously renovated throughout, this turnkey property is entirely move-in ready. An inviting living room features a cozy gas fireplace & matching pair of custom built-ins framing a classic bay window. The chef's kitchen is equipped with all-new appliances, an oversized stainless steel sink and an incredibly useful pantry cabinet. Both bathrooms are brand new, with the hallway bath providing dedicated space for a full size, side by side washer & dryer. Complete mechanicals peace of mind is yours w/ a brand new natural gas fired water heater, newer forced warm air furnace and central air conditioning. NO LAND LEASE! The Seller will pay off all remaining "rent" due! You are only mile from vibrant downtown Madison's fine restaurants, boutique shopping, library, post office and train station. Enjoy the best of shoreline living w/ access to Madison's 3 pristine town beaches, the state's longest stretch, 2 miles of sandy beach at Hammonasset State Park. Don't wait on this gem. Professional photos soon

29 Wilshire Road Unit 29, Madison
$564,900
2 Beds ⋅ 2 Baths ⋅ 24182034 MLS ⋅ Kensington Acres North BLDG.
Welcome home to 6 Essex Lane! Elegant and inviting, this meticulously maintained ranch style condo is set in a quiet corner of Kensington Acres North. With a beautiful back patio, you can relax in a peaceful oasis, surrounded by nature. Inside, the expansive living room flows into the dining room, all with lots of light. The gracious kitchen offers quality cabinetry and a granite countertop breakfast bar. From the dining room, head out through the sliders to the three season sunroom that radiates style and charm, you can use it for entertaining and everyday enjoyment. The two bedrooms are generously sized and the primary has an ensuite full bath. If you need storage space, there is an abundance in the attic, accessible via pull-down stairs. A convenient one car garage is just a short walk away. This is a fantastic location only a mile from downtown Madison with its shops, library, cafes, restaurants and train station. And it is an easy drive to the amazing local beaches and Hammonasset State Park. This is shoreline living at its best, come and check it out soon!

6 Essex Ln Unit 6, Madison
$500,000
2 Beds ⋅ 2 Baths ⋅ 24203562 MLS ⋅ Kensington Acres North BLDG.
Charming two-bedroom ranch in the desirable North Kensington community. Enjoy central air conditioning, gas heat, and a beautiful screened-in porch overlooking the pond-an inviting space to relax and unwind. The home features generously sized bedrooms and two full bathrooms, offering comfort and convenience for guests and everyday living. Cozy up by the gas fireplace, which is easy to turn on and off. A detached one-car garage provides additional storage and parking.

14 Hampshire Road Unit 14, Madison
$500,000
2 Beds ⋅ 2 Baths ⋅ 24200381 MLS ⋅ Windermere East BLDG.
Step out of the 3 season, enclosed porch to the private park-like grounds of this ranch-style condo in Windermere East. This home has been tenderly cared for and is ready to welcome its next owners to enjoy. The main living areas offer a nice open floor plan, combining the living and dining areas. Both bedrooms are large enough to accommodate a king-size bed or two twin beds. There are two full bathrooms with stall shower in guest bath and a full-size washer and dryer. The electrical/solar system in this unit results in unbelievably low utility bills. The desirable location is with in an approximate 5 to 6 minute drive to the center of town where one will find shopping, the library, restaurants, the seasonal Friday afternoon Farmer's Market on the Town Green as well as several cultural events, including concerts, fairs, and art exhibits. In addition to nearby Hammonasset State Park, this home is just minutes from Madison's three resident beaches. The local train station provides commuter service to New Haven where one can connect to a two-hour train ride to NYC.

22 Thelbridge St Unit 22, Madison
$499,900
3 Beds ⋅ 2 Baths ⋅ 24199405 MLS
First Time Offered In 25 Years. This contemporary raised ranch, set on 2.36 secluded acres, is located in a quiet cul-de-sac neighborhood just minutes to town. The living room with hardwood floors features a cathedral ceiling with beams, a wood burning fireplace, floor to ceiling windows with double sliders to a deck with built in bench, perfect for morning coffee or evening enjoyment. The adjacent dining room also has sliders to a patio. The kitchen with breakfast bar is waiting for your personal touches. Down the hall you will find 2 spacious guest bedrooms with large closets that share a hall bath. The primary bedroom with walk-in closet has its own full bath. Downstairs is a large family room with a wood stove to keep things cozy and sliders to an additional patio. The laundry is also located on this level. Though located in a private wooded setting, this home is conveniently located to town, beaches, parks and all that Madison has to offer.

35 Aileen Dr, Madison
$455,000
2 Beds ⋅ 2 Baths ⋅ 24164028 MLS ⋅ Kensington Acres South BLDG.
Privacy & convenience are both found within this updated detached stand-alone Ranch home in sought after Kensington Acres. Enjoy this 'tucked away' home yet a short walk to historic downtown Madison with its famed bookstore, shopping, restaurants & retail stores. This home has been beautifully maintained and shows pride of ownership throughout. Enjoy single floor living in your 2 bedroom, 2 bath home which features granite countertops in kitchen & baths, hardwood floors, light & bright open floor plan, natural gas fireplace and a year-round heated sunporch which is surrounded by nature and very well will be your most favorite room! Detached single car garage plus additional resident & guest parking. Newer Samsung gas stove & Bosch dishwasher. Updated HVAC - Trane AC unit manufactures date 1/2021 & Trane furnace date 4/2021.

6 Ladshaw Dr Unit 6, Madison
$450,000
2 Beds ⋅ 2 Baths ⋅ 24196129 MLS ⋅ West Sussex Place BLDG.
Welcome to effortless, low-maintenance living in this beautifully maintained 2-bedroom, 1.5-bath condominium, built in 2006. Offering 1,296 square feet of thoughtfully designed living space, plus approximately 608 square feet of finished lower-level space, this home provides exceptional flexibility for today's lifestyle. The bright, open floor plan features hardwood floors, a spacious kitchen with granite countertops and stainless steel appliances, and inviting living and dining areas filled with natural light. Enjoy your morning coffee on the welcoming front porch or relax on the private rear patio. Additional highlights include an attached one-car garage, natural gas heat, central air conditioning, and a versatile lower level ideal for a family room, home office, fitness area, or recreation space. Ideally located just minutes from downtown Madison, you'll enjoy easy access to charming shops, restaurants, beautiful beaches, the movie theater, and I-95. Combining comfort, convenience, and the best of shoreline living, this move-in-ready home is an exceptional opportunity. There street noise when you are outside the unit. Sellers have found suitable housing. Great rental unit for investors! Please schedule showings for after 12 noon. Thanks

12 W Sussex Pl Unit 12, Madison
$449,000
1 Beds ⋅ 2 Baths ⋅ 24198868 MLS ⋅ West Sussex Place BLDG.
End-unit townhouse condominium in Madison, Connecticut - open-concept living,attached garage, plus a finished lower level! Built in 2006 at West Sussex Place, this move-in ready home features hardwood floors, a kitchen with granite countertops and stainless steel appliances, and a light-filled living and dining area on the main level. Primary bedroom, Loft (or 2nd bed) and the full bath are on the upper level, with a half bath on the main floor. The finished lower level adds approximately 608 square feet of flexible space for a home office, media room, fitness area, or recreation room, along with laundry and storage. Outside, a covered front porch and private rear patio extend the living space on a level, lightly wooded lot. Natural gas hot air heat, central air conditioning, natural gas hot water, and underground utilities, with vinyl siding for low exterior maintenance. An attached one-car garage plus assigned driveway parking. West Sussex Place is a 25-unit community minutes from downtown Madison, Boston Post Road shops and restaurants, Madison Art Cinemas, Hammonasset Beach State Park, and the beaches of Long Island Sound, with quick I-95 access. Please note that I-95 traffic is audible outdoors. Living in Madison provides access to the Surf Club, beach front area with sporting events, stretch of sand and surf, along with seasonal restaurant. The Madison shoreline is beautiful, you truly need to live it!

5 W Sussex Pl Unit 5, Madison
$239,900
3 Beds ⋅ 2 Baths ⋅ GC539333 MLS
Discover the perfect blend of space, privacy, and opportunity with this expansive 5.02-acre property. Nestled in a peaceful setting, this versatile parcel offers endless potential, whether you're dreaming of a quiet country retreat, a mini homestead, or room to grow and explore. The property features a well-maintained 3-bedroom, 2-bath singlewide home that provides comfortable living with a functional layout. Inside, you’ll find a welcoming living area, a spacious kitchen with ample cabinetry, and a split-bedroom floor plan that offers added privacy. The primary suite includes a private bath, while the additional bedrooms are ideal for family, guests, or even a home office. Step outside and take in the true value of this property. Over 5 acres of open space ready for your vision. Bring your animals, start a garden, build a workshop, or simply enjoy the wide-open skies and serene surroundings. With plenty of room for outdoor recreation, storage, or future improvements, this property is a rare find for those seeking both space and flexibility. Conveniently located yet tucked away enough to enjoy peaceful country living, this property offers the best of both worlds. Don’t miss your chance to own a slice of land with unlimited possibilities—schedule your showing today!

11533 E Us 90, Madison
$235,000
3 Beds ⋅ 2 Baths ⋅ GC539752 MLS
This 2019 single wide mobile home sits on 10.34 fully fenced acres and gives you the space, privacy, and freedom that is hard to find. The land is split nicely with about half cleared and half wooded, offering a good mix of open ground and natural surroundings. The cleared portion is great for a homesite, animals, gardening, or even starting a small farm. The wooded area has a perimeter trail along with several trails running through it, making it easy to walk, ride, or just enjoy the outdoors. There is also plenty of wild game, giving you the option to hunt right on your own property. This property has a lot of potential and can be used in many different ways. It is a great option for someone looking to live a quieter lifestyle with room to spread out. You could bring horses, cows, goats, or chickens, or use the open land for planting and growing your own food. It would also work well as a weekend getaway or hunting spot, or even as an investment for the future. With the mix of cleared and wooded land, you have flexibility to use it how you want without starting from scratch. The entire 10.34 acres is fully fenced, which adds both convenience and peace of mind, especially for animals or keeping your property lines clearly defined. There is no HOA and no deed restrictions, so you are not limited in how you use the land. Whether you want to build more, park equipment, bring in additional homes, or simply enjoy it as it is, the choice is yours. Another big plus is that the property has fiber optic internet available, making it easy to work from home, stream, or stay connected while still enjoying country living. It is not always easy to find that combination of privacy and reliable internet. The location offers a good balance of quiet living with access to nearby towns and cities. It is just 26 minutes to Live Oak, 29 minutes to Mayo, 42 minutes to Lake City, 48 minutes to Valdosta, 1 hour and 10 minutes to Tallahassee, and 1 hour and 30 minutes to Gainesville. This makes it convenient for shopping, work, and travel while still coming home to your own private space. If you are looking for land with room to grow, no restrictions, and plenty of possibilities, this property is worth a look.

1147 Se Hammerly Street, Madison
$174,900
3 Beds ⋅ 2 Baths ⋅ R4911579 MLS
Three (3) Bedroom Two (2) Bath Singlewide Residence located on 6.8 Acres. 3+/- miles outside of town. Newer HVAC and Roof. Carport and Shed. Well and Septic Tank. Flood Zone X. Zoned Agricultural. No HOA. Billboard lease through 2027. Great visibility from Interstate 10. Permissible uses according to Madison County include Agricultural, Agricultural Commercial, Outdoor Recreational, or other allowed by Special Exception.

1142 Sw Jim Clark Road, Madison

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.