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

$665,000

3 Beds ⋅ 3 Baths ⋅ 24216910 MLS

Escape the everyday and step into your own private sanctuary at 3 Poole Road, a charming 3-bedroom, 2.5-bathroom Log Cabin offering 2,237 square feet of light-filled, thoughtfully designed living space on nearly seven acres of serene, wooded grounds in Madison. Built in 2005, this comfortable Cape Cod style home features an intuitive, flexible floor plan with seamless flow between the main gathering areas and the expansive outside space. The upper level has two spacious bedrooms and extra living space overlooking the property's incredible setting, offering rare acreage, complete privacy, and endless possibilities for outdoor recreation, gardening, or potential expansion.

3 Poole Rd, Madison

$549,900

4 Beds ⋅ 2 Baths ⋅ 24216244 MLS

Experience the best of coastal living in this distinctive property, featuring a beautifully renovated main residence, an income-producing in-law residence, and generous grounds in one of Connecticut's most desirable shoreline communities. Set toward the rear of the .76-acre parcel, comfortably removed from Boston Post Road, the main home enjoys an attractive setting surrounded by lush greenery and magnificent mature trees. The expansive grounds provide a beautiful backdrop for outdoor entertaining, gardening, or simply relaxing in the natural surroundings. Extensively renovated throughout, the main residence combines contemporary style with everyday comfort and convenience. Enjoy a beautifully updated kitchen and bath, attractive new flooring, modern lighting, replacement windows, a new roof, and an updated heating system. These substantial improvements offer the immediate enjoyment of a move-in-ready home without the disruption and expense of a major renovation. A bright breezeway connects the home to its attached one-car garage, providing convenient, sheltered access, while the full basement offers valuable storage and utility space. A separate in-law residence toward the front of the parcel is currently leased for $1,700 per month. This rental income provides a meaningful financial advantage, helping offset ownership expenses while adding versatility and value.

252 Boston Post Rd, Madison

$699,900

4 Beds ⋅ 3 Baths ⋅ 24216661 MLS

Nestled on a beautifully elevated homesite, this classic Colonial offers the perfect blend of privacy, comfort, and New England charm. Set in a desirable neighborhood just minutes from charming Madison Village, the Town Green, shops, restaurants, and the stunning Connecticut shoreline, this home offers the perfect blend of location and lifestyle. This spacious 4-bedroom home features a welcoming living room with a fireplace, a formal dining room, an eat-in kitchen, and a generous family room with a second fireplace. A wonderful, sun porch overlooks the peaceful backyard, creating the perfect space to relax or entertain. Upstairs, you'll find four spacious bedrooms, including the primary suite with a private bath and walk-in closets. The finished lower level provides additional flexible living space for a recreation room, home office or gym. Additional highlights include a 2-car garage, newer roof, siding and windows, plus the convenience and peace of mind of natural gas and a whole-house generator. New septic tank installed to the current septic system. Neck River School district

7 Milestone Ln, Madison

$545,000

2 Beds ⋅ 2 Baths ⋅ 24216462 MLS ⋅ Windermere East BLDG.

Don't miss this opportunity to own a beautifully updated Ranch in the desirable Windermere community! Nestled in a peaceful cul-de-sac setting, this home is the larger of the two ranch-style models and offers comfortable, versatile living with the added bonus of a family room featuring a new gas fireplace. Enjoy new luxury vinyl flooring thru the main living area and stylish new carpeting in the bedrooms. The updated kitchen features new appliances, including a gas stove with hood, refrigerator and dishwasher, along with quartz countertops, freshly painted cabinets with new hardware and a butcher-block island. The bathrooms have also been tastefully refreshed with new vanities, and new lighting above the sinks. The primary bathroom features a new bathtub, while the guest bath offers new shower doors and a new stackable washer and dryer. Besides the gas fireplace in the family room, a ceiling fan with light has been added, creating a comfortable space to relax or entertain. Year-round comfort is enhanced by a new Mitsubishi Electric heat pump and air-conditioning system. Additional improvements include an Anderson screen door. Step outside to enjoy the 12'x12' enclosed porch, a patio, garden area, and a park-like backyard. The adjacent garage adds everyday convenience. Exterior maintenance is provided. Just minutes from Madison's beautiful shoreline and charming downtown village!

3 Currycross Rd Unit 3, Madison

$599,000

2 Beds ⋅ 3 Baths ⋅ 24215402 MLS

Timeless New England charm meets contemporary style in this beautifully remodeled Cape, where classic character and thoughtful modern updates come together effortlessly. The inviting interior features an open-concept kitchen and dining area designed for both everyday living and effortless entertaining. Just off the kitchen, a lovely deck extends the living space outdoors, creating the perfect setting for al fresco dining, relaxed afternoons, and gathering with family and friends. The spacious living room, centered around a wood-burning fireplace, offers warmth and timeless appeal. Two generously sized bedrooms, beautifully updated bathrooms, and California Closets provide comfort and refined functionality. The completely reimagined basement offers exceptional versatility, with flexible bonus spaces ideal for a home office, guest retreat, gym, playroom, or additional living area. A garage adds convenience and valuable storage. Ideally situated near town, local shops, beautiful beaches, and a brand-new elementary school, this home offers the best of coastal New England living, blending enduring charm, modern comfort, and a location that makes everyday life feel just a little more special.

182 Green Hill Rd, Madison

$395,000

3 Beds ⋅ 2 Baths ⋅ 24215669 MLS

A terrific home at a remarkable price for Madison! This solid, well-maintained property offers incredible potential for buyers looking to make a home their own. Lovingly cared for more than 60 years by the original owner, this home is now ready for its next chapter. While cosmetic updates would enhance the interior, it offers the opportunity to move right in and make renovations over time, at your own pace. Notable improvements include low-maintenance vinyl siding, a new well pump, a new garage door, a whole-house generator, and a roof just over 10 years old. The property also boasts a large, private lot with attractive landscaping, providing a peaceful setting to enjoy the outdoors. The best part of this home is the four season bonus room addition featuring vaulted ceiling and flooded with natural light. It provides the perfect space to entertain company. With its solid construction, history of care, and opportunity for personalization, this property offers exceptional value. Bring your vision and make this well-loved home your own! The home is an estate sale and is being sold as-is. Offers must include as-is rider. **HIGHEST/BEST DUE BY 6 PM- 10/26. **

466 County Rd, Madison

$265,000

1 Beds ⋅ 1 Baths ⋅ 24215713 MLS

Dream of sunny beach days and enjoying all that the shoreline lifestyle offers? Then this one is for you ! Fully turn-key, this seasonal cottage is directly bordering Hammonasset Beach State Park, only a short walk away. This cottage has enough room to sleep eight or more people comfortably in a cozy environment. Enjoy the park's two miles of sandy beaches, secluded coves, picnic areas and wildlife sanctuary with 936 acres of protected waterfront lands all easily accessible from your quaint cottage via a direct walking path and a bike path. Large shed for hosting parties and extra storage along with new firepit for those beautiful summer nights! Enjoy your morning coffee with the large fenced in wrap around deck and after those sandy beach days you can rinse off in the solar outdoor shower with privacy screen. This purchase MUST be all cash or personal/home equity loan and is seasonal April 1st-October 31st. Cottage is on leased land and does not qualify for conventional financing. New deck, new floors, new shed, new bathroom, newly painted and fully furnished! This property also comes with two electric scooters to get you to the beach even faster! This cottage is the perfect summer oasis and amazing alternative to RV living. Do not miss this opportunity to make this your next home!

28 North St, Madison

$695,000

4 Beds ⋅ 2 Baths ⋅ 24215254 MLS

Take a 3D Tour OR Enjoy a Video Walkthrough 24/7! Move right into this charming 4 BR, 2 Bath Madison farmhouse offering 1,956 SF of living space on a nearly 1-acre, level lot backing to protected land trust open space! Built in 1940 with a spacious 1980 addition, this home combines classic character with thoughtful updates, including the convenience of a first-floor primary BR. Three additional BRs upstairs provide flexibility for guests, hobbies or work-from-home needs. Beautiful hardwood floors, a welcoming Living Room with stone fireplace & sunny bay window, a bright, spacious Kitchen with breakfast bar, formal Dining Room, home Office & an expansive Rec Room with direct access to the rear deck provide plenty of room to spread out. The major improvements are already complete: NEW roof (2024), furnace & central A/C (2023), water heater (2022), septic tank (2011), replacement windows (2008) & upgraded 200-amp electrical service. Low-maintenance aluminum siding adds to the appeal. Relax on the inviting 3-season enclosed front porch with windows or entertain on the expansive rear deck overlooking the level backyard & protected land trust open space. A detached 2-car garage offers convenient loft storage. Enjoy quick access to I-95, Madison's charming village center, shoreline & Hammonasset Beach State Park. At $695,000, this move-in-ready home offers space, flexibility & significant recent improvements. Schedule your private showing today!

67 Nortontown Rd, Madison

$250,000

24215018 MLS

Imagine building a home that reflects your vision in one of Connecticut's most desirable shoreline communities! This fully approved residential building lot at 54 Railroad Avenue is walking distance from downtown and offers an exciting opportunity to create your own special place in Madison, known for its timeless New England charm, beautiful beaches and welcoming village atmosphere. Enjoy nearby Hammonasset Beach State Park, charming downtown shops and restaurants, and convenient access to surrounding shoreline communities. A wonderful opportunity to put down roots and embrace the appeal of coastal Connecticut living.

54 Railroad Ave, Madison

$569,900

4 Beds ⋅ 3 Baths ⋅ 24211348 MLS

Beautifully updated and wonderfully maintained, this exceptional 4-bedroom Colonial offers a great & comfortable lifestyle in a highly desirable Madison location. From the moment you enter, you'll appreciate the natural light, handsome hardwood floors, and thoughtful improvements throughout. At the heart of the home is a gorgeous, sun-filled kitchen featuring a big bay window, center island, granite countertops, gas range, stainless appliances, and pantry. Just beyond the kitchen, the inviting family room makes a wonderful gathering space with its soaring cathedral ceiling, wood stove, and glass French doors opening to a fabulous multi-level deck. The spacious living room is filled with natural light, while the dining room is perfectly suited for entertaining. Upstairs, the private primary suite features a remodeled full bath, accompanied by three additional bedrooms and a second beautifully updated full bath. The extensive list of improvements includes replacement windows, brand-new roof, new oil tank, new well pump and water softener, and a whole-house generator.Outside, the attractive, easy-care yard provides plenty of room to relax and entertain, while the two-car garage and central air adds everyday convenience. A wonderful opportunity to enjoy the best of Madison living in a home where style, comfort, and quality updates come together beautifully. OFFERS HAVE BEEN RECEIVED. HIGHEST & BEST WITH NO ESCALATIONS TO BE IN BY 10AM MONDAY OCTOBER 19th

41 Bradley Corners Rd, Madison

$850,000

7 Beds ⋅ 4 Baths ⋅ 24214953 MLS

Welcome to 69 Bradley Corners Road, a truly unique property nestled on over 6 acres in beautiful Madison! Offering an incredible combination of privacy, space, and resort-style amenities, this home is anything but ordinary. Enjoy your own private retreat complete with a picturesque pond, tennis court, and in-ground pool, perfect for entertaining or simply enjoying everything this property has to offer. Inside, you'll find a stunning primary suite and a spacious layout featuring a full in-law apartment for guests or multigenerational living. Looking for even more space? The lower level offers additional potential to expand your living area and make it your own. With over 6 acres to enjoy, endless possibilities, and amenities rarely found together in one property, this is truly a one-of-a-kind opportunity. Properties like this don't come along often. Don't miss your chance to see everything this incredible Madison home has to offer!

69 Bradley Corners Rd, Madison

$599,000

3 Beds ⋅ 2 Baths ⋅ 24214239 MLS

Welcome to this beautifully maintained home on a cul-de-sac street. Low traffic, great for play. When entering this inviting home, the foyer greets you with the natural light of the main living room's oversized windows creating a bright ambience that flows seamlessly into the eat-in kitchen and dining area. The updated kitchen features newer stainless steel appliances (2024), while beautiful hardwood floors add warmth and character throughout the main level. Just a few steps up, you'll find three generously sized bedrooms,including a spacious primary bedroom, all featuring beautiful hardwood floors that continue into the hallway. Entire interior painted, along with new interior doors (2024). The versatile lower level offers additional living space, complete with a cozy raised hearth fireplace w/newer wood-burning/pellet stove (2023), newly renovated full bathroom and laundry area(2020). Whether you envision a comfortable family room, home office,or creative retreat,this space offers endless possibilities. Step outside onto the expansive deck overlooking a lush,lovingly landscaped property and spacious, level yard.This private outdoor oasis is perfect for summer entertaining,relaxing evenings, or simply enjoying the peaceful surroundings. Complete with a two-car garage and ideally situated just minutes from schools (Neck River, Polson,Hand) the shoreline, shopping, restaurants, and interstates, this home offers the perfect combination of style, functionality, and convenience.

16 Tamarac Dr, Madison

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Madison Real Estate

Newest Listings in Madison

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