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28 North St, 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

41 Bradley Corners Rd, 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

16 Tamarac Dr, 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

14 Bower Rd, Madison
$599,900
4 Beds ⋅ 2 Baths ⋅ 24212728 MLS
Nestled on a picturesque stretch of Madison's desirable shoreline community, this exceptional property offers the perfect blend of New England charm, privacy, and convenience. Set on a beautifully maintained lot, 14 Bower Road provides an inviting setting for year-round living or a relaxing coastal retreat. Thoughtfully designed living spaces are filled with natural light, creating a warm and welcoming atmosphere throughout. The home features spacious gathering areas, a well-appointed kitchen, comfortable bedrooms, and seamless indoor-outdoor living ideal for entertaining family and friends. Outdoor spaces offer room to relax, garden, or simply enjoy the tranquility of the surrounding landscape. Ideally located just minutes from Madison's vibrant town center, beaches, boutiques, restaurants, and commuter routes, this property combines a peaceful residential setting with easy access to everything the Connecticut shoreline has to offer. A two-car attached garage and full walk-out basement provide excellent storage, workshop space, or future finishing potential. The private backyard offers plenty of room for entertaining.

14 Bower Rd, Madison

270 Scotland Rd, Madison
$449,000
3 Beds ⋅ 2 Baths ⋅ 24210705 MLS
Tucked away on a private setting high above Scotland Road, 270 Scotland Road offers the perfect combination of privacy, space, and natural beauty. Set on approximately 2 acres of lightly wooded land, this 3-bedroom, 1.5-bath raised ranch enjoys elevated surroundings with seasonal views toward the Hammonasset River. The main level features a comfortable, flowing layout with hardwood floors throughout the spacious living room, complete with a fireplace that creates a warm and inviting focal point. The updated kitchen offers stainless steel appliances, tiled flooring, and a generous dining area with plenty of space for everyday living and entertaining. Three bedrooms and a full and half bath are conveniently located on the main level. Downstairs, you'll find additional finished living space with a beautiful brick fireplace, offering flexibility for a family room, home office, recreation area, or guest space. Set back in a private, lightly wooded setting, this home offers the opportunity to enjoy the peace and privacy of acreage while remaining conveniently located in Madison. With its elevated setting, river views, spacious lot, and flexible living space, 270 Scotland Road is a property worth seeing in person.

270 Scotland Rd, Madison

273 Horse Pond Rd, Madison
$600,000
5 Beds ⋅ 2 Baths ⋅ 24210111 MLS
**Offered for the first time in over 54 years, this oversized ranch provides exceptional space, flexibility, and charm. Originally built in 1972 by a longtime Madison resident for his two daughters, this 2,240squarefoot home has been thoughtfully designed to accommodate a variety of living arrangements. Located in Madison's desirable southern section on a generous 1.33acre lot, the property offers convenient access to the downtown village, sandy town beaches, Hammonasset State Park's walking trails, and Madison's Town Campus. It's a rare opportunity to enjoy privacy while remaining close to everything Madison has to offer. This unique residence was constructed as a true duplex ranch, featuring two full kitchens, two living rooms, and two full baths-all connected and all on one level. A welcoming front foyer provides two separate entrances, complemented by two additional rear entrances. With three bedrooms on one side and two bedrooms on the other, the layout is ideal for an inlaw suite, multigenerational living, or simply enjoying the benefit of five total bedrooms and abundant square footage. Craftsmanship from a bygone era is evident throughout, with many rooms showcasing the original parquet hardwood floors. Both kitchens open directly to the expansive and private rear yard, offering wonderful outdoor enjoyment and potential for future expansion if desired. Don't miss this rare chance to own two homes in one-a truly special offering in Madison.

273 Horse Pond Rd, Madison

23 Esterly Farms Rd Unit 23, 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

6 Bower Rd, Madison
$559,900
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

35 Aileen Dr, 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

40 East St, Madison
$210,000
1 Beds ⋅ 1 Baths ⋅ 24197701 MLS
Enjoy the best the shoreline has to offer in this charming seasonal summer cottage. Bring your swimsuits, sunscreen, and a book... and move right into this furnished, turnkey summer house. One of the largest cottages, this home has central air, 2-3 parking spaces, and a lovely lot. Sun-filled, airy, and spacious, with a large kitchen and dining room, a generous living room, and 2 additional rooms. Listed as a 1-bedroom, but could easily be used as 2 bedrooms, or 1 bedroom and a flex room. The half bath even has an all-in-one washer/dryer unit. You'll love the outdoor shower, fresh air, under the stars, no sand in the house. Outside is a large storage shed and a screened gazebo, perfect for al fresco dining! Finish out the summer enjoying sunsets and relaxation. A quick bike ride to Hammonasset Beach State Park, restaurants, downtown Madison, the movie theater and shops.

40 East St, Madison

25 Samantha Ln, Madison
$529,000
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

32 North St, Madison
$139,900
2 Beds ⋅ 1 Baths ⋅ 24170543 MLS
New roof, new windows, new deck! 32 North Street is ready for you and calling you home! Set on one of the largest lots in Dud's Village, this lovely cottage is the idyllic seasonal abode. Equipped with 2 bedrooms, 1 full bath, and an outdoor shower, you will surely enjoy your summers along the Madison shoreline here. The recently refreshed kitchen and fresh coat of paint throughout will undoubtedly delight. And let's not forget the new floors in the kitchen and living room. The enclosed front porch is simply charming offering additional living space and featuring daybeds for cool summer sleepovers. Outside is an entertainer's paradise - a desirable corner lot with the oversized deck and enough yard space to host all your family and friends. Just a short distance to Salt Meadow Park, Hammonasset Beach State Park and downtown Madison, you'll always have something to do! And with summer right around the corner, you'll want to move quickly! Schedule your tour today and fully embrace coastal living at its finest! The village is seasonal - April 1st through October 31st. Land is leased by cottage owners, and the land lease is currently $5,400 per year. New windows and deck to be completed as soon as possible.

32 North St, Madison

16 North St, Madison
$125,000
1 Beds ⋅ 1 Baths ⋅ 24160104 MLS
Escape to the Connecticut shoreline with this beautifully maintained seasonal cottage in Dud's Village in Madison-the perfect summer retreat just minutes from the beach. Located less than one mile from Hammonasset Beach State Park, Connecticut's largest shoreline park, this charming getaway offers effortless access to two miles of sandy beaches, scenic walking and biking trails, and endless summer activities. Residents of Dud's Village also enjoy a private path that leads directly to the beach, making spontaneous sunset walks and beach days part of everyday life. This fully furnished, move-in-ready cottage has been thoughtfully maintained and cared for, allowing you to start enjoying the season immediately. The cozy interior includes one bedroom with built-in storage, a nicely stocked kitchen, a sleeper sofa for additional guests, a remodeled bathroom with a fresh modern feel, and the added convenience of an in-unit washer and dryer. Step outside to your spacious wrap-around deck, designed for relaxed coastal living and easy entertaining. The outdoor space comes complete with a grill, tabletop firepit, and patio seating, creating the perfect setting for summer evenings, morning coffee, or gathering with friends after a day at the beach.

16 North St, Madison

10 Runnymede Ln Unit 10, 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

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