Madison Real Estate

Welcome to Madison, Connecticut – a picturesque coastal town that beautifully balances small-town charm with modern conveniences. Nestled in New Haven County along the stunning shoreline of Long Island Sound, Madison is known for its vibrant community, scenic landscapes, and rich history. With its tree-lined streets, historic homes, and welcoming atmosphere, it’s no wonder that Madison has become a sought-after destination for families, retirees, and anyone looking to embrace a quality lifestyle.

Madison boasts a thriving downtown area filled with delightful shops, cozy cafés, and award-winning restaurants that cater to every palate. Whether you’re savoring fresh seafood at a waterfront eatery or exploring boutique stores, the local charm is palpable. The town also hosts a variety of events and festivals throughout the year, fostering a strong sense of community and making it easy to meet neighbors and make new friends.

For outdoor enthusiasts, Madison offers an abundance of recreational opportunities. From the pristine beaches along the coastline to the scenic trails of Hammonasset Beach State Park, there’s no shortage of places to enjoy nature. The town’s commitment to preserving its natural beauty is evident in its parks and conservation areas, providing residents with a serene escape just moments from home.

Education is a top priority in Madison, with highly-rated public schools and a commitment to fostering academic excellence. The town’s rich history, coupled with its vibrant arts scene, further enhances the quality of life for its residents.

In Madison, you’ll find not just a place to live, but a community to thrive in. Discover your dream home in this charming coastal haven today!

Newest Listings in Madison

$1,200,000

4 Beds ⋅ 4 Baths ⋅ 24205471 MLS

Step into nearly three centuries of Connecticut history, beautifully reimagined for modern living. Privately set on 1.5 beautifully established acres, this exceptional circa-1752 former Helen Foster Snow homestead is a rare convergence of architectural authenticity, exceptional craftsmanship, modern comfort, and effortless shoreline living. Just minutes from Hammonasset Beach State Park (~5 miles) and The Surf Club (~4 miles), the property offers an extraordinary sense of privacy and tranquility while remaining close to the beauty and amenities of the Connecticut shoreline. Once home to renowned journalist, author, and humanitarian Helen Foster Snow, the residence possesses a sense of history that cannot be recreated. Wide-plank floors, hand-hewn beams, period details, and beautifully proportioned, light-filled rooms preserve the soul of the original home, while extensive improvements have made the property exceptionally comfortable for contemporary living. What makes this estate particularly remarkable is the depth and continuity of its stewardship. The current owner-the craftsman behind East Guilford Construction, a respected local builder known for historic restoration and traditional post-and-beam construction-undertook improvements with the same level of care one would expect when restoring a property intended to remain in the family for generations.

148 Mungertown Rd, Madison

$489,000

2 Beds ⋅ 3 Baths ⋅ 24203806 MLS ⋅ Esterly Farms BLDG.

Welcome to 23 Esterly Farms, an exceptional end-unit townhouse offering the perfect blend of style, comfort, and turnkey convenience in one of Madison's most sought-after condominium communities. This meticulously maintained 2-bedroom, 2.5-bath home has been thoughtfully updated throughout, allowing you to move right in and enjoy worry-free living. The sun-filled interior showcases fresh paint, all-new Harvey replacement windows, updated lighting, new window treatments, and a beautifully remodeled primary bath. The refreshed kitchen features brand-new stainless steel appliances, while the inviting living area is highlighted by a fireplace with elegant new glass doors. Additional upgrades include a new washer and dryer, delivering everyday convenience and modern functionality. Significant mechanical improvements provide added peace of mind, including a new furnace, central air condenser, and hot water heater. Nearly every major system has been updated, making this home truly move-in ready.

23 Esterly Farms Rd Unit 23, 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

$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

$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

$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

$3,200,000

5 Beds ⋅ 4 Baths ⋅ 24203132 MLS

Experience coastal Madison living with beach rights in this to be built 5-bedroom, 3.5-bathroom home featuring 4,937 square feet of high-end craftsmanship. Designed with an airy, open layout, the main level boasts 9'+ ceilings, Red Oak hardwood floors, and a chef's kitchen equipped with white Shaker cabinetry, quartz countertops, a butler's pantry, and premium Sub-Zero, Wolf, and Bosch appliances. Modern efficiency meets high design with 4-zone HVAC and tankless hot water. Upstairs, unwind in luxurious porcelain-tiled baths complete with Kohler fixtures, custom glass-door showers, and a soaking tub. Outside, enjoy a large main deck, covered front entry, landscaped grounds, and a spacious 3-car garage all just minutes from the shoreline, local schools, and downtown Madison.

22 Stone Rd, Madison

$735,000

4 Beds ⋅ 3 Baths ⋅ 24201961 MLS

DESIRABLE 4 BEDROOM NORTH MADISON HOME. Nestled on 2.62 peaceful, tree-lined acres in desirable North Madison, this classic yellow Colonial combines timeless New England charm with spacious, modern comfort. Offering 2,600+ square feet of beautifully appointed living space, the four-bedroom, 2.5 bath home is anchored by rich hardwood floors throughout the home. The front Living Room is spacious, the Family Room has a warm, inviting wood burning fireplace that serves as the heart of the main floor. The light-filled layout includes a finished basement that provides versatile extra rooms for a home gym, media area, or private office, while central air conditioning ensures year-round comfort throughout. An attached two-car garage adds everyday convenience to this tranquil retreat. Outside, the property opens up to an impressive bluestone patio designed for seamless outdoor entertaining, or simply taking in the scenic, natural views of your vast private grounds. The setting balances serene seclusion with easy accessibility, placing you just minutes from local hiking trails, North Madison amenities, close to Durham, with the vibrant shops and beaches of downtown Madison, 15 minutes away. Perfect for both relaxing everyday life and hosting family and friends, this classic residence captures the very best of shoreline Connecticut living.

450 County Rd, 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

$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

$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

$350,000

4 Beds ⋅ 3 Baths ⋅ 24201020 MLS

Super opportunity to buy a home in Madison at a reasonable price! Needs work but well worth the effort. Owner suspects mold may be present in the basement but has received quotes for remediation and contents have been removed. The attached release and indemnification form must be signed prior to access being granted. This is a very rare and special property just waiting for you to make your own! New pictures are being taken, the one in this listing is old. Sale may be subject to probate approval

22 Pine Ridge Dr, Madison

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