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River Road, Madison
$2,500,000
24158112 MLS
THE RAREST OF OPPORTUNITIES! Over 5.5 stunning sun-drenched acres held by the same family for centuries. This level pastoral setting offers a "once-in-a-lifetime" canvas for a premier custom estate (got horses?) or an unique boutique development. With over 1,300 feet of road frontage & no wetlands, the land is prime for a subdivision of 5 one-acre+ lots. Under the town's Open Space Conservation District Regs, there is potential for 6 lots. An additional 2.4 abutting acres is now for sale too further expanding the possibilities. See MLS#21462686. Another plus, both natural gas & city water are available in the road. The parcel is mostly framed by classic stonewalls, offers salt meadow & Hammonasset River views directly across the street, & is notably not in a high-risk flood zone. And talk about LOCATION, LOCATION, LOCATION! Perfectly situated less than 0.5 miles from Hammonasset Beach State Park with its 2 miles of continuous sandy beach & the Meig's Point Nature Center AND the trailhead of the multiuse Shoreline Greenway AND Madison's Salt Meadow Park w/ new dog park, athletic fields & kayak/canoe launch AND finally the Rettich Preserve, 11 acres with walking trails along the river, ALL less than 0.5 miles! Downtown Madison's fine dining, shops & train station for easy commuting to New Haven, New York & Boston is just 2 miles away. Whether building a private family compound or high-end residential enclave, this is a legacy property without equal on the Connecticut shoreline.

River Road, Madison

146 Chittenden Field Ln, Madison
$1,825,000
3 Beds ⋅ 2 Baths ⋅ 24121062 MLS
Just Steps from the Sand - Your Coastal Retreat Awaits! Wake up in your 3-bedroom beach house to the sound of waves rolling onto your private beach. Bright, open living spaces bring the ocean right inside, while each room offers serene, million-dollar views and the soothing rhythm of the sea. This is more than home - it's your slice of paradise. Enjoy panoramic ocean views from every room, walls of glass, and a wrap-around deck. Professionally decorated throughout with an option to buy all furnishings. This charming beach house has been beautifully updated and is move-in ready. The kitchen shines with brand-new cabinets, sleek countertops, modern appliances, and stylish light fixtures that create a luxurious ambiance. With its thoughtful updates and coastal location, this home perfectly blends modern comfort with seaside charm. With its prime location, the home has proven itself to be an excellent income-generating property.

146 Chittenden Field Ln, Madison

85 Fawn Brook Cir, Madison
$1,030,000
4 Beds ⋅ 3 Baths ⋅ 24151588 MLS
A Shoreline Masterpiece: Custom Cape Cod Living on 1.10 Private Acres Welcome to 85 Fawn Brook Circle, an immaculate Cape Cod retreat nestled at the end of a quiet, picturesque cul-de-sac. This 4-bedroom, with a first floor primary suite; 2.5-bathroom home has been thoughtfully reimagined with a level of detail rarely seen. Rich hardwood floors flow through every room, complemented by crisp custom moldings and elegant built-in bookcases that frame the living room with timeless charm. At the heart of the home lies a gourmet kitchen, designed for both the serious chef and the frequent host. Featuring a professional-grade gas range, an expansive eat-at island, and an abundance of custom storage, it's a space where culinary dreams meet daily convenience. A finished lower level with a recreation/gym. The exterior is equally impressive, is a large Pergola just off the kitchen set on pavers for relaxation and enjoying the outdoors Set on 1.10 lush acres, the property features a standout additional detached three-car garage barn. With an upper level, this versatile space is the ultimate solution for a quiet home office, a professional workshop, or a creative studio. Just minutes from Madison's iconic beaches and vibrant downtown, this home offers the peace of the woods with the soul of the shoreline.

85 Fawn Brook Cir, Madison

104 Scotland Rd, Madison
$850,000
5 Beds ⋅ 2 Baths ⋅ 24161452 MLS
Set on what is arguably the most beautiful lot in downtown Madison. This enchanting 5-bedroom farmhouse perfectly blends timeless charm with modern convenience. The nearly one-acre, meticulously manicured property makes a lasting impression. Complete with majestic stone walls & a stunning brick patio. Inside, the home welcomes you with a thoughtfully designed mudroom, creating a private and practical entry point. The oversized family room is filled with natural light and anchored by a cozy wood stove, offering a warm and inviting atmosphere. The fully remodeled eat-in kitchen is truly the heart of the home, featuring abundant storage & spacious dining room, & a seamless flow into a versatile living room that can also serve as a formal dining space. A bright first-floor office with a skylight provides flexibility and can easily function as a guest bedroom, conveniently located near a full bath. Upstairs, you'll find five charming bedrooms with built-ins, generous closet space, and a beautifully updated full bathroom. The primary bedroom stands out with its high ceilings & airy feel, while the entire second floor is bathed in sunlight. Additional highlights include newer gas heating, central air, city water, a two-car garage and an updated roof. All of this and is just a short walk to downtown Madison's shops, beach, restaurants, train station, and movie theater. This is a rare opportunity to own a truly special home in an unbeatable location.

104 Scotland Rd, Madison

129 Acorn Rd, Madison
$725,000
4 Beds ⋅ 3 Baths ⋅ 24111617 MLS
A stone's throw away from the heart of Madison Village, perfectly positioned at 1.4 miles from the bustling center, with beaches, recreational fields, and the renowned Bookstore. Shopping, dining, and are all conveniently close, making this an ideal location for those seeking both tranquility and community amenities. Occupying a generous .74-acre level lot, the low-maintenance garden and an inviting deck. Inside, the home's open floor plan establishes a harmonious connection between living spaces. The versatile living room, anchored by a cozy fireplace,Eat in Kitchen offers flexible floor plan .Two rooms serve as a family room or dining room, depending on your lifestyle needs. Adjacent to the kitchen, a sun-drenched room provides additional adaptability, whether you require a casual sitting area or a formal dining space. The remodeled Eat in kitchen features modern finishes, leathered granite counters, stainless appliances that cater to both function and style. The adjoining dining area is warm and inviting, perfect for hosting meals and social gatherings. Upstairs, four bedrooms boast hardwood floors with generous room sizes. The lower level of the home reveals a finished space, perfect for a home media room, gym, or office. Flexible as additional living areas for leisure and productivity. This property is a true gem, offering a blend of lifestyle and convenience all within the charming context of Madison's coastal community.

129 Acorn Rd, Madison

221 Duck Hole Rd, Madison
$600,000
3 Beds ⋅ 3 Baths ⋅ 24181933 MLS
**PLEASE SUBMIT ANY OFFERS BY 12PM TUESDAY 6/16** Nestled in a serene woodland setting, this charming raised ranch offers the perfect blend of classic shoreline character and modern upgrades throughout over 2,000 square feet of finished living space. The home immediately impresses with its warm cedar shingle exterior and brick facade, gorgeously framing a home that is as sturdy as it is stylish. Inside, the heart of the home is a spectacular, sun-drenched kitchen featuring dramatic vaulted wood-plank ceilings, premium granite countertops, and a custom stone backsplash-a true chef's delight. The main level is anchored by a spacious primary bedroom featuring a private en-suite bath and custom closets designed for effortless organization. Enjoy ultimate, permanent privacy as this property directly borders 4.28 acres of protected Madison Land Conservation Trust open space. Meticulously maintained and updated for modern comfort, recent improvements include a 2021 propane conversion for heating and cooling, recent AC condenser and water heater replacements (2024), and enhanced attic insulation (2023). Ideally located just minutes from Madison's pristine beaches, town center, and commuting routes, this home is a move-in-ready gem.

221 Duck Hole Rd, Madison

7 Madrina Ln, Madison
$500,000
3 Beds ⋅ 1 Baths ⋅ 24126980 MLS
Location, Location, Location!! Introducing a charming and well-maintained raised ranch home, nestled in the heart of shoreline Madison. Here at 7 Madrina Lane, step into an inviting living room with fireplace, and newer kitchen equipped with stainless steel appliances. Boasting 3 bedrooms, and pristine hardwood flooring - this delightful residence offers a cozy, spacious environment for everyday living. The rear covered deck offers a serene space to unwind, while nearby Main Street and amenities add to the allure of this home. Take a short walk to Pent Road Beach and explore the scenic Greenway Trail, leading to the iconic Hammonasset Beach State Park. Just minutes from I-95, this location offers the best of shoreline living - enjoy easy access to beautiful beaches, top-rated dining, including the famous Lenny & Joe's Fish Tale, and all that downtown Madison has to offer. Discover the charm of Main Street with local favorites like RJ Julia Booksellers, Cafe Allegre, and Madison Cinemas.

7 Madrina Ln, Madison

3 Sandgate Cir Unit 3, Madison
$475,000
2 Beds ⋅ 3 Baths ⋅ 24139904 MLS ⋅ Windermere East BLDG.
Welcome to this 1,853 sq. ft. townhouse in desirable Windermere. A five-minute drive will take you to the center of town, where one will find a variety of specialty stores, as well as the famous local bookstore, where a leisurely lunch can be enjoyed in its cafe. The Library, several restaurants, a cinema, where classic films are shown, are also popular attractions. During the warmer months, it is fun to stop by the Friday afternoon Farmers' Market to pick up fresh vegetables, flowers, fish and more. The Surf Club, as well as Madison's two additional beaches, are also just minutes from the home. Features of this home include a kitchen/dining area that is open to the cozy family room with its gas fireplace, providing heat and ambiance on cooler evenings. The large combination living room and dining room offers plenty of space for entertaining and family gatherings and he three-season sunroom is a perfect spot to relax with a good book and the private patio offers a pleasant place on which to enjoy your favorite drink and a summer meal. The attached garage, with an entrance to the family room, makes carrying groceries inside very convenient, especially during inclement weather. Two extra large bedrooms and two full baths, as well as the laundry area, are on the upper level. An extra room on this level works perfectly as a guest room, office or studio. List price takes into consideration that some updating may be desired to reflex one's own taste.

3 Sandgate Cir Unit 3, Madison

12 W Sussex Pl Unit 12, Madison
$425,000
2 Beds ⋅ 2 Baths ⋅ 24196129 MLS ⋅ West Sussex Place BLDG.
Welcome to effortless, low-maintenance living in this beautifully maintained 2-bedroom, 1.5-bath condominium, built in 2006. Offering 1,296 square feet of thoughtfully designed living space, plus approximately 608 square feet of finished lower-level space, this home provides exceptional flexibility for today's lifestyle. The bright, open floor plan features hardwood floors, a spacious kitchen with granite countertops and stainless steel appliances, and inviting living and dining areas filled with natural light. Enjoy your morning coffee on the welcoming front porch or relax on the private rear patio. Additional highlights include an attached one-car garage, natural gas heat, central air conditioning, and a versatile lower level ideal for a family room, home office, fitness area, or recreation space. Ideally located just minutes from downtown Madison, you'll enjoy easy access to charming shops, restaurants, beautiful beaches, the movie theater, and I-95. Combining comfort, convenience, and the best of shoreline living, this move-in-ready home is an exceptional opportunity. There street noise when you are outside the unit. Sellers have found suitable housing. Great rental unit for investors! Please schedule showings for after 12 noon. Thanks

12 W Sussex Pl Unit 12, Madison

168 Boston Post Rd Unit 1 & 2, Madison
$278,500
2 Baths ⋅ 24054796 MLS
Welcome to a fantastic opportunity on Boston Post Rd in beautiful Madison, CT! This versatile commercial condo spans 1,775 square feet and offers the flexibility to be split into two separate units, making it perfect for a variety of uses, whether you're looking to establish a retail space or a professional office. With plenty of parking available, your clients and customers will appreciate the convenience. The property features natural gas heating and central air conditioning, ensuring a comfortable environment year-round. Additionally, if you're not ready to purchase, the units are also available for lease, providing you with options to suit your business needs. Don't miss out on this prime location to grow your business in a vibrant community!

168 Boston Post Rd Unit 1 & 2, Madison

49 Cottage Road Unit 3, Madison
$165,000
1 Beds ⋅ 1 Baths ⋅ 24190693 MLS ⋅ Boston Post Road (875) BLDG.
Ever wanted your own perfect summer beach getaway?! This countrycute singlefamily cottage in Madison's Seabreeze Community gives you exactly what you've been dreaming of - a charming, lowkey retreat just minutes from the beach and all the fun of the shoreline. With its cozy, relaxed feel, simple, easyliving layout, and a lovely private patio for morning coffee or evening drinks, it's an ideal spot for weekend escapes, summer stays, or for anyone wanting to downshift into beachtown life. You'll love being close to sand, surf, local restaurants, and Madison's vibrant downtown, with the convenience of lowmaintenance living in a classic cottage setting. If you've been looking for a sweet, affordable shoreline hideaway with timeless cottage charm, this is the one to come see.

49 Cottage Road Unit 3, Madison

7 3rd St Unit 7, Madison
$164,900
1 Beds ⋅ 1 Baths ⋅ 24165867 MLS
New septic TBD B 4 close.tucked away like a hidden jewel at the shoreline, this storybook beach cottage captures the charm of coastal living.Approached by a classic brick landing, this cottage welcomes you with beachy curb appeal and a sense of relaxed living. Bathed in natural light and thoughtfully updated, this delightful retreat offers a warm and inviting interior designed for effortless living. Every detail reflects comfort and charm, creating the perfect escape for weekend getaways,or entire summer living. This cottage is located in a vintage beach community nestled on leased land ( each cottage is set on a small plot)located in the picturesque coastal town of Madison Ct. This unique village is situated on 6 acres adjacent to the sandy stretch of Long Island Sounds Hammonassett State Park, Salt Meadow Park (includes dog park) & the Greenway trail. Upon entering you'll find a modern open floor plan with vaulted ceilings. The exterior delights with a huge private deck for entertaining or a peaceful place to dream while reading a favorite book.Cottage offers a huge shed in addition to a private gravel driveway.Since the Land is leased a mortgage is not an option financing must be cash.No motorcycles, trailers , renting or Air bnb. Subject to rules and regulations of land owner. Must be approved by landowner through application.Land lease, taxes, and garbage removal approximately $6600 a year As a resident you have access to Madison Town Beaches for a modest yearly charge

7 3rd St Unit 7, Madison

73 South St, Madison
$135,000
1 Beds ⋅ 1 Baths ⋅ 24133620 MLS
Madison-beach property! Dreaming of sunny beach days and enjoying all the shoreline lifestyle offers? Then this one is for you! Fully turnkey renovated seasonal cottage directly bordering Hammonasset Beach State Park. Enjoy the park's two miles of sandy beaches, secluded coves, picnic areas, wildlife sanctuary and 936 acres of protected waterfront lands all easily accessible from your quaint cottage via a direct walking and biking path. Outbuilding for for all your tools and beach toys! Close to shopping, dining, and shore amenities. Cottage comes fully furnished and ready to enjoy. Minutes to Madison train station or take your uber and enjoy the weekend away from busy city life. Visit the wine shops, bistros and shops that this beautiful New England Seaside town has to offer. Walking distance to restaurants. Peaceful vacation from April 1st to October 31st! Access to Madison Surf Club and East and West Wharf Beaches as an added perk as a Madison resident (yearly cost). Purchase needs to be all cash or personal loan/home equity loan as cottage on leased land does not qualify for conventional financing.

73 South St, Madison

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