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$5,000,000
3 Beds 3 Baths 24192754 MLS
Some properties are defined by the house that sits on them. Others are defined by the land itself...by history, landscape and a sense of beauty that simply cannot be created. This is such a place. Owned and farmed by the same family for 200 years, this remarkable 16 Acre piece sitting on the Hammonassett River is the last piece of the original farm to be sold. With over 1500 ft. bordering the river, the property unfolds across open hay fields, tidal marshes and expansive river views. The landscape changes with the seasons and the light, grasses moving with the wind and water reflecting the ever changing sky...a landscape that is both bucolic and breathtaking. This is an exceptional setting for a distinctive country residence, a private retreat or a place to enjoy a quieter chapter of life. An existing, well appointed, three bedroom ranch home sits on the property and enjoys the same remarkable views. Comfortable as it stands, the home could ultimately serve as a guest house, artist's studio or private office. The property offers the potential for more than one lot, but with generations of family ownership, the sellers have hopes to see the land remain intact, so no soil testing has been undertaken for subdivision. A survey is available and buyers considering additional development should conduct their own due diligence. After two centuries in the same family, this is a rare opportunity to become the next steward of an extraordinary Connecticut landscape.

118 River Rd, Madison

$1,378,800
3 Beds 3 Baths 24185353 MLS
Originally built in 1825, this residence has been thoughtfully updated to preserve its historic essence while incorporating modern conveniences. Nestled on a generous 4.38-acre lot, this extraordinary home boasts 3 spacious bedrooms and 2.5 beautifully appointed bathrooms within its expansive 3,500 square feet of living space. As you step inside, you'll be captivated by the elegant oak hardwood floors that flow throughout. The state-of-the-art kitchen is a chef's dream, showcasing exquisite Calacatta Gold marble countertops and top-of-the-line stainless steel appliances, making it perfect for both casual meals and entertaining guests. Step outside, and you'll find your own oasis featuring an inviting in-ground gunite pool, complete with a pool house, ideal for relaxation and summer gatherings. The vast property offers ample possibilities for subdivision or the construction of an additional home, providing the perfect opportunity for creating a cherished family compound. Additionally, this unique property includes a carriage house with a 3-bay garage with a guest suite above, complete with 2 bedrooms and a full bath, ideal for visitors or as a private office. With its unique character and spacious layout, this home promises to be a tranquil retreat, making it a must-see for those seeking privacy and luxury in an idyllic setting. Don't miss the chance to make this exceptional property your own!

1308 Durham Rd, Madison

$1,299,000
3 Beds 3 Baths 24181259 MLS
Rare coastal compound opportunity in Madison's highly desirable Seaview Beach area. Situated on approximately one-half acre just moments from the shoreline, this unique property features a main residence and a newer detached accessory dwelling unit, offering flexibility rarely found in one of Connecticut's premier shoreline communities. The main home is clean, functional, and ready for a new owner's vision, while the newer detached dwelling provides additional living space ideal for guests, multigenerational living, rental income, a private home office, or extended family. Separate utilities further enhance the property's versatility. Located within Madison's top-rated school district and surrounded by higher-end homes, this property offers a unique combination of location, flexibility, and long-term potential. Enjoy convenient access to beaches, downtown Madison, restaurants, shopping, marinas, parks, and commuter routes. Whether you're seeking a private coastal retreat, family compound, investment opportunity, or future expansion potential, opportunities like this are increasingly rare. Seller financing available for qualified buyers. Buyer to perform all due diligence regarding future use, expansion, and development opportunities.

32 Liberty St, 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

$925,000
3 Beds 4 Baths 24193091 MLS
Give away the leaf blower and the yard tools (or sell, whichever you prefer) and get ready to enjoy life on a peaceful cul-de-sac in Madison's highly desirable Strathmore Farms community with natural gas and city water, 3 Longview Terrace is an exceptional stand-alone condominium home that captures the essence of luxurious coastal living. Recent updates to this home include the furnace and roof, both new in 2025. This thoughtful 3-bedroom Colonial seamlessly blends elegance and comfort, offering a flowing first-floor layout that includes a formal dining room, a living room, an eat-in kitchen that opens to a family room with a fireplace as a focal point, and rounded out with a dedicated home office/flex space. The beautiful eat-in kitchen is the heart of the home with sliding doors that open to a large deck overlooking the meadow. Beyond the elegant interior, this property is a dream for nature enthusiasts, offering access to the community gazebo as well as kayaking, paddle boarding, and birdwatching. Enjoy the marsh-view setting, the quick two-mile drive to the stunning shoreline of Hammonasset Beach State Park, and convenience to Madison village. This home combines the space and privacy of a detached home with a premier, carefree lifestyle.

3 Longview Ter Unit 3, Madison

$925,000
3 Beds 4 Baths 24192261 MLS Strathmore Farms BLDG.
Set on a peaceful cul-de-sac in Madison's highly desirable Strathmore Farms community, 3 Longview Terrace is an exceptional stand-alone condominium home that captures the essence of luxurious coastal living. This thoughtful 3-bedroom Colonial seamlessly blends elegance and comfort, offering a flowing first-floor layout that includes a formal dining room, a living room, an eat-in kitchen that opens to a family room with a fireplace as a focal point, and rounded out with a dedicated home office/flex space. The beautiful eat-in kitchen is the heart of the home with sliding doors that open to a large deck overlooking the meadow. Beyond the elegant interior, this property is a dream for nature enthusiasts, offering access to the community gazebo as well as kayaking, paddle boarding, and birdwatching. Enjoy the marsh-view setting, the quick two-mile drive to the stunning shoreline of Hammonasset Beach State Park, and convenience to Madison village. This home combines the space and privacy of a detached home with a premier, carefree lifestyle.

3 Longview Ter Unit 3, Madison

$755,000
3 Beds 3 Baths 24194435 MLS
Move right into this meticulously maintained home, proudly offered for sale for the very first time by its original owners. This distinctive contemporary 3-bedroom home welcomes you with an inviting natural setting surrounded by mature trees, charming stone walls, and striking rock outcroppings. Inside, abundant natural light fills the thoughtfully designed living spaces, including a formal living room, dining room, and a cozy family room with a gas fireplace. The sunroom is a true highlight, featuring cathedral ceilings, skylights, and walls of windows that bring the beauty of the outdoors inside, creating a peaceful retreat to enjoy throughout the seasons. The fully applianced eat-in kitchen offers a breakfast bar, tile flooring, and a comfortable dining area ideal for morning coffee, casual meals, and entertaining. Upstairs, the spacious front-to-back primary suite serves as a private retreat with its own full bath, a walk-in closet, and a second lighted closet. Two generously sized bedrooms offer excellent closet space, with one featuring a private balcony. Additional features include central air and whole house generator. Set on a peaceful cul-de-sac, the home is just a short stroll to downtown shops, restaurants, coffee shops, beaches, and the country club. Perfectly positioned along the Connecticut shoreline, it also offers convenient rail access to both Boston and New York City, making it an exceptional year-round residence or weekend getaway.

44 Sterling Park, Madison

$700,000
3 Beds 3 Baths 24172475 MLS
BEACH HOME! BEACH RIGHTS! NEEDS WORK! It is not everyday that an opportunity to own a double lot in such a shoreline area. This charming English Cottage-style Cape, situated on a generous footprint for the area, is ready for it's next chapter-whether that involves a thoughtful renovation or the construction of a brand-new coastal home perhaps. Residents enjoy deeded rights to a private association sandy beach located just at the end of the street! The main residence of which there are no photos for obvious reasons once you see it (NEEDS WORK) currently features three bedrooms and 1.5 baths but adding to the property's versatility is a delightful in good condition accessory apartment, which offers a full kitchen, full bath, a private bedroom and a cozy living area anchored by a stone fireplace and two separate exterior entrances. This setup is ideal for multi-generational living, a great guest suite or potential rental income. Maybe live in this while redoing the other portion. The property is a double lot that accommodates four dedicated parking spaces - a true luxury for beachside living. Best of all, the property is located where no flood insurance is required, offering peace of mind alongside the salt air. Whether you choose to polish this unique gem or start fresh with a custom build, this is the perfect canvas for your seaside lifestyle.

67 Blakeman Rd, Madison

$579,900
3 Beds 1 Baths 24203485 MLS
Escape to the Connecticut shoreline with this beautifully styled Cape, ideally situated in desirable Madison. Offering 3 bedrooms and 1 full bath, this charming home features inviting indoor and outdoor living spaces designed for comfortable everyday living and relaxed coastal living. Set on a private, lightly wooded corner lot, the property offers a peaceful sense of privacy while remaining close to everything Madison has to offer. Recent improvements include new cedar siding, windows throughout with custom window treatments, propane fireplace installation, and professional interior painting, all completed in 2025. The roof and septic system were both replaced in 2022. Just a 5-minute drive to vibrant downtown Madison, enjoy easy access to charming boutiques, restaurants, and cafes, as well as Hammonasset Beach State Park, with miles of sandy shoreline and scenic coastal walks. Convenient access to I-95 puts downtown New Haven approximately 25 minutes away. Turnkey and thoughtfully updated, this inviting Cape offers the perfect blend of classic New England charm, modern improvements, and an exceptional shoreline location. A wonderful opportunity to enjoy the best of Madison living in a peaceful coastal setting.

6 Bower Rd, Madison

$559,000
3 Beds 3 Baths 24198297 MLS
Nicely maintained 3-bedroom, 3-full-bath home nestled in a quaint cul-de-sac setting. The home is in very good condition and offers comfortable living space both inside and out. The spacious kitchen features granite countertops, plenty of cabinet space, and a center island-perfect for everyday living and entertaining. Primary Bedroom has its own private full bath. Living Room-Dining combination offers a slider to a deck overlooking the peaceful backyard and small pond, creating a relaxing setting to enjoy the outdoors. Lower level offers a large family room with a walk-out to a patio, providing additional living and entertaining space. With its peaceful setting, versatile living spaces, and inviting outdoor areas, this home is ready to welcome its next owners.

25 Samantha Ln, Madison

$500,000
3 Beds 3 Baths 24204341 MLS
A Fantastic Opportunity in an Adorable Neighborhood Welcome to a home that offers incredible potential, a great location, and peace of mind with many of the major systems already updated. While this property needs work and updating, the big-ticket items have been taken care of, making this an exciting opportunity for someone looking to build equity and create a home that truly reflects their style. Recent improvements include a 2024 roof, 2024 central air conditioning, 2024 furnace, 2025 oil tank, 2025 garage doors, a 2023 hot water heater, and a brand-new septic system installed in 2026. With so many important mechanical and structural components recently addressed, you can focus your energy on transforming the interior and making the home your own. Nestled in an adorable, established neighborhood surrounded by homes that are significantly more expensive, this property presents a rare opportunity . Whether you're looking for a renovation project or an investment opportunity, the possibilities are here. Bring your vision, your ideas, and your contractor - this one is ready for its next chapter! A few offers have been submitted, please submit highest and best by Friday at 5pm

18 Saint Francis Woods Rd, 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

$365,000
3 Beds 4 Baths A4703557 MLS
Diamond in the Rough! Incredible home situated on a secluded 1.65-acre property surrounded by expansive views of nature, peace, and quiet. If you're looking for privacy, space, and an opportunity to create something special, this property has tremendous potential. The home offers generous living space with a flexible floor plan, hardwood flooring, a wood-burning fireplace, and plenty of natural light. Outside, the property truly stands apart with mature surroundings, an in-ground pool, and plenty of room to enjoy the peaceful setting. The property needs some work and is being offered As-Is, providing a great opportunity for a buyer to add their own personal touches and make it their own. Enjoy country-style privacy while still being within convenient reach of Madison and area amenities. Bring your vision—this is a property with space, privacy, and possibilities that are hard to find.

423 Sw Alderene Park Way, 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

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