Madison Real Estate

Welcome to Madison, Connecticut – a picturesque coastal town that perfectly balances small-town charm with modern conveniences. Nestled along the shores of Long Island Sound in New Haven County, Madison is renowned for its stunning beaches, vibrant community, and rich historical heritage.

One of the town's most alluring features is its scenic waterfront, where residents and visitors alike can enjoy leisurely strolls along the sandy shores or partake in various water activities. The historic downtown area boasts a delightful mix of boutique shops, artisanal eateries, and cozy cafes, making it an ideal spot for a weekend outing or a casual afternoon stroll.

Madison is also home to some of Connecticut's top-rated schools, making it a prime location for families seeking quality education in a nurturing environment. The town's commitment to preserving its natural beauty is evident in its numerous parks and recreational areas, including the picturesque Hammonasset Beach State Park, which offers expansive beaches, hiking trails, and picnic spots.

Culturally rich, Madison hosts a variety of community events throughout the year, from farmers' markets to art shows, fostering a strong sense of belonging among its residents. With its friendly neighborhoods, excellent amenities, and easy access to nearby cities like New Haven and Hartford, Madison truly embodies the best of Connecticut living.

Whether you’re looking to buy your first home, invest in a vacation property, or simply explore the area, Madison invites you to discover its unique blend of coastal charm and vibrant community spirit. Come experience all that this enchanting town has to offer!

Newest Listings in Madison

$1,750,000

4 Beds ⋅ 5 Baths ⋅ 24191892 MLS

Build your custom dream home in South Madison! Welcome to this incredible opportunity in a prime location! Set on a level, treed, 2.32-acre lot on the hidden, more secluded end of Mungertown Road, offering PRIVACY and GREAT CONVENIENCE. Just THREE MILES to town and beaches, ONE MILE to Hand and Polson schools, and .25 MILES to the state-of-the-art Neck River Elementary, opened in 2025. Enjoy quick access to I-95 and the train. Work with an ELITE CONNECTICUT BUILDER with 35-PLUS YEARS EXPERIENCE to customize one of his flexible floor plans or BRING YOUR OWN! This property offers tremendous potential and versatility. Optional high-end features can be tailored to the buyer's taste, such as hardwood floors, crown molding, coffered or tray ceilings, and raised paneling. Personalize your home with your choice of cabinets, countertops, lighting, and tile fixtures, all built for LOW MAINTENANCE with multiple heating options available. Conveniently located near local shopping, dining, parks, and major commuter routes. A rare opportunity in an ideal Madison location-contact us today to start planning your dream build!

262 Mungertown Rd, Madison

$875,000

4 Beds ⋅ 3 Baths ⋅ 24194353 MLS

Incredible opportunity to own this classic four-bedroom Colonial in the highly sought-after Knob Hill neighborhood. Nestled on a lovely, quiet street just minutes from town and the beaches, this home is beautifully set back from the road, offering both privacy and curb appeal. The kitchen with vaulted ceilings opens to the family room and a stunning screened porch, creating the perfect flow for everyday living and entertaining. A full bath next to the office/guest room on the main level adds convenience and flexibility. Upstairs, you'll find four generously sized bedrooms, including a primary suite with its own private bath. The vaulted screened porch is a true highlight - an ideal place to relax and enjoy the peaceful surroundings. Step outside to a brick patio overlooking the private backyard, perfect for outdoor gatherings or quiet evenings. The finished lower level provides additional living space for recreation, a playroom, home gym, or office, along with a second fireplace and ample storage. Additional features include a brand new roof, recently painted exterior, city water, central air conditioning, potting shed, and a two-car garage. Knob hill is a one of a kind neighborhood, holiday get togethers, 4th of July bike parade and safe walking and biking. Located just north of the Boston Post Rd.

25 Knob Hill Rd, Madison

$2,190,000

5 Beds ⋅ 3 Baths ⋅ 24191331 MLS

COME EXPERIENCE THIS ONE-OF-A-KIND, FULLY RENOVATED MADISON HOME ON A RARE DOUBLE LOT WITH PRIVATE BEACH RIGHTS! Just 300 feet from the sandy shoreline, this exceptional home has been completely reimagined from a traditional raised ranch into a stunning elevated ranch with a bright, open-concept floor plan designed for modern living and effortless entertaining. Every detail has been thoughtfully curated to blend contemporary elegance with coastal charm. The main level features a spectacular chef's kitchen anchored by a nearly 10-foot white quartz island, premium appliances, and exceptional finishes. Two driveways provide ample parking, while two sets of washers and dryers offer added convenience. Multiple living spaces are bathed in natural light, including a breathtaking sunroom with brand-new oversized Marvin picture windows framing serene views toward Long Island Sound. A spacious hallway leads to a beautifully renovated full bath, a conveniently located laundry area, and the luxurious primary suite. Originally two bedrooms, this private retreat now offers a remarkable 9' x 12' walk-in closet and a spa-inspired ensuite featuring a double vanity, dual rain showers, and built-in shower benches. The finished lower level includes three generously sized bedrooms, a beautifully renovated full bath with a double vanity, a second brand-new washer and dryer, and an expansive family room, providing flexible space for guests, recreation, or relaxing after a day at the beach!

15 Highland Ter, 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

$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, 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

$699,900

4 Beds ⋅ 2 Baths ⋅ 24192861 MLS

**7/26/26 Open House Cancelled** Updated, 4-bedroom, 2-bathroom New England gem boasting 2,348 square feet of thoughtfully designed living space. Pride of ownership shines through with improvements already completed for you, including a new roof (2026), freshly painted exterior (2026), a replaced septic system (2021), and a new well (2020). Interior features include a gorgeous remodeled kitchen with quartzite counters and stainless steel appliances that flows into a family room featuring dramatic cathedral ceilings and easy access to the rear yard entertaining space. The exterior is a true staycation paradise. The level backyard hosts a pristine in-ground pool paired with a dedicated pool shed equipped with electricity-ideal for pool storage. Peace of mind thanks to an upgraded 200-amp electrical service complete with a generator transfer switch. Perfectly situated just north of Route 1, this home offers the ultimate shoreline lifestyle. Enjoy being just a 5-minute drive to Madison's quintessential town center and a quick 8-minute drive to the beach. Move right in and start enjoying summer by the pool!

170 Mungertown Rd, Madison

$550,000

3 Beds ⋅ 2 Baths ⋅ 24192835 MLS

A rare investment opportunity with unmatched storage and garage space! Tucked away on a private 2-acre lot just minutes from I-95 and everything Madison has to offer, this unique property combines immediate rental income with an incredible opportunity for the next owner. The 3-bedroom home is currently tenant-occupied, generating $2,500 per month in rental income, while the expansive detached garage remains available for the owner's exclusive use. The home offers a functional layout with three bedrooms and a full basement, providing both comfort and future potential. The true highlight, however, is the exceptional 1,800+ square-foot garage featuring soaring ceilings, 12-foot door openings, and enough room to accommodate up to 10 vehicles. Whether you're a car collector, RV owner, contractor, hobbyist, or entrepreneur looking for the ultimate workshop or storage space, this impressive garage is a rare find. Offering privacy, convenience, income potential, and an unmatched garage setup, this is a one-of-a-kind property.

141 Duck Hole Rd, 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

$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

$400,000

1 Beds ⋅ 2 Baths ⋅ 24190995 MLS ⋅ Esterly Farms BLDG.

Welcome to 3 Esterly Farms Rd. Best value in Madison! Tucked away in the sought-after Esterly Farms community, this 1,372-s.f. townhouse offers a seamless blend of comfort & shoreline charm. The thoughtfully designed layout is anchored by stunning Brazilian cherry wood floors that flow throughout the main level, adding a rich, polished warmth to the home. The inviting living area features a classic wood-burning fireplace, perfect for cozy evenings. The upper level is dedicated to a spacious primary suite, providing a private retreat complemented by a primary bathroom as well as an office space. Large windows invite natural light to pour across the living spaces, while the convenience of NATURAL GAS, PUBLIC WATER, and central air ensures year-round comfort. The unit offers a partially finished basement as well as a walkup attic. Living at Esterly Farms means embracing a lifestyle where exterior maintenance is handled for you, leaving more time to enjoy everything Madison has to offer. Located just 1.7 miles from the vibrant Madison Town Green, you are perfectly positioned to enjoy seasonal farmers market & the beloved summer outdoor concert series. Whether you're exploring the boutiques & cafes of the historic downtown area or spending a day at the Madison Surf Club, this location puts the best of the Connecticut coast right at your doorstep. This is a rare opportunity to enjoy a refined, low-maintenance home in one of the region's most desirable communities.

3 Esterly Farms Road Unit 3, Madison

$579,000

2 Beds ⋅ 3 Baths ⋅ 24190216 MLS ⋅ Legend Hill BLDG.

Welcome to 250 Legend Hill Road, a beautifully maintained townhouse condominium in Madison's sought-after Legend Hill community with a tennis/pickleball courts, a Gunite pool, and a clubhouse housed in the original cobblestone mansion. This particular home is positioned to capture both morning and afternoon light, and distant views of Long Island Sound. Inside, the first floor features a gracious entry foyer, a formal dining room, spacious living room with a fireplace, 4 season sun room that connects the Living Room and the bright eat-in kitchen. With nice pantry space and a Powder Room off the hall, plus access to the garage, the first floor is spacious and light filled. The primary suite has three closets and a full bathroom with shower with glass doors. A second bedroom offers its own en-suite bath and a generous closet.

250 Legend Hill Rd Unit 250, Madison

$595,000

1 Beds ⋅ 2 Baths ⋅ 24190672 MLS ⋅ Centre Village Of Madison BLDG.

Welcome to 9 Centre Village Drive, a beautifully renovated condominium offering the perfect blend of style, comfort, and convenience in one of Madison's most desirable locations. Originally built in 1985 and extensively updated in 2018, this move-in ready home features an open, light-filled floor plan designed for today's lifestyle. The spacious kitchen is the heart of the home, showcasing quartz countertops, marble tile backsplash, stainless appliances, and abundant cabinetry. There is a welcoming living room with a gas fireplace and striking Palladian window that fills the space with natural light. A versatile first-floor room offers possibilities as a home office, den, or potential second bedroom. Completing the main level is a beautifully renovated full bathroom featuring a tiled walk-in shower. Upstairs, you'll find a sunny loft which is ideal for a home office, reading nook, or creative space along with a generously sized primary bedroom offering excellent closet space, a renovated full bathroom with a tiled shower, and the convenience of a dedicated laundry room. Additional highlights include a one-car attached garage, plus the peace of mind that comes with a roof and skylights replaced within the last 7 years. Ideally situated just a short stroll from Madison's picturesque Town Green, downtown shops and restaurants, and beaches, this this exceptional home offers the very best of shoreline living. Agent owner related.

9 Centre Village Dr Unit 9, Madison

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