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$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
$665,000
2 Beds ⋅ 3 Baths ⋅ 24186310 MLS ⋅ Legend Hill BLDG.
Rarely available, this unit is the largest size Townhouse ("Model D") at Legend Hill. It benefits from a quiet location in the complex away from the main road. This unit has been well maintained with excellent natural light and updated neutral decor. Since purchasing, these owners have installed all new flooring throughout first level, in addition to new carpets on second level. Also recently replaced were central-air, furnace and all new stainless steel appliances. This unit is over 1800 square feet, not inclusive of the finished sunroom off of kitchen and the 2 finished rooms in the walk out basement. There is plenty of storage in the attached 2 car garage, with another unfinished storage area in basement. The kitchen has been updated with granite counters and refaced maple cabinets. The first floor powder room has been remodeled with marble flooring. In addition the upstairs master bath has been completely remodeled from top to bottom. The sunken living room with vaulted ceiling and fireplace is a wonderful room to curl up with a book or gather with friends and family. Legend Hill has an idyllic, peaceful setting on over 80 acres with the best condo amenities in this market area that include pool, tennis courts and historic cobblestone clubhouse with beautiful vistas. The clubhouse with the sunny patio overlooking the pool is a favorite place to gather on Friday evening. Schedule your showing now. This one won't last long.

81 Legend Hill Rd Unit 81, Madison
$1,100,000
3 Beds ⋅ 4 Baths ⋅ 24190527 MLS
This exceptional ranch-style home is set on a beautifully landscaped lot just minutes from Madison's charming town center and sandy beaches. A semi-circular driveway, classic brick and clapboard exterior, stone walls, and mature plantings create a stunning first impression.Step into the sun-filled two-story foyer and discover elegant finishes throughout, including hardwood floors, crown molding, tray ceilings, custom millwork, wainscoting, and built-in cabinetry. The inviting Great Room is anchored by a propane fireplace with an inset heater, while the chef's kitchen features off-white cabinetry, soapstone countertops, a Viking 6-burner propane cooktop, Thermador refrigerator, Bosch dishwasher, wine cooler, undermount microwave drawer, plus a pantry. The heated sunporch with two new skylights opens to an expansive Trex deck with awning and fenced backyard-perfect for relaxing. The spacious primary suite offers walk-in closets, a spa-inspired bath with travertine counters, tiled shower, private deck access, and a convenient stackable washer and dryer in an adjacent closet. Two additional bedrooms, a private office (or potential fourth bedroom), a second laundry room, and a finished lower level (983 sq ft) with custom built-in cabinetry and bookshelves provide extra living space. A walk-up floored attic with a cedar closet offers added storage. 3 zone hydro-air heating and cooling, a whole-house generator, irrigation system, solar panels, a 3 car garage with epoxy floor too!

72 Strawberry Hill Rd, Madison
$569,000
2 Beds ⋅ 2 Baths ⋅ 24190408 MLS ⋅ Kensington Acres North BLDG.
Beautifully maintained 2-bedroom condominium in desirable Kensington North, just minutes from Madison's charming town center and beautiful beaches. The bright, inviting kitchen opens to the living and dining areas, where a gas fireplace creates a warm and welcoming atmosphere. A delightful sunroom overlooks the private patio and beautifully landscaped garden, offering a peaceful retreat for relaxing or entertaining. The home features two spacious bedrooms, two updated baths, and the ease of one-floor living. A detached one-car garage is conveniently located just steps away.

40 Hampshire Road Unit 40, Madison
$519,000
3 Beds ⋅ 3 Baths ⋅ 24188102 MLS
Move right into this beautifully maintained 3-4 bedroom, 2.5-bath Raised Ranch in a desirable South Madison neighborhood, perfectly situated between Madison and Guilford. This inviting home features gleaming hardwood floors, an updated kitchen with new cabinetry, a cozy gas fireplace, a spacious primary suite, and a sun-filled four-season room overlooking the private backyard. The finished walkout lower level adds exceptional living space with a family room, wood-burning fireplace, additional bedroom, half bath, and endless possibilities for a home office, gym, or recreation room. Enjoy a level, private yard just minutes from charming town centers, beautiful beaches, and everything the Connecticut shoreline has to offer.

101 Sandelwood Dr, Madison
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 24190199 MLS
Step into a story nearly three centuries in the making. Tucked away on a total of 3 enchanting acres along Connecticut's picturesque shoreline, this extraordinary circa-1752 former Helen Foster Snow homestead is a place where history whispers through every room and timeless beauty meets modern living. Ideally located just minutes from the area's scenic shoreline destinations, including Hammonasset Beach State Park (~5 miles) and the Surf Club Beach (~4 miles), this exceptional property offers the rare combination of historic charm, privacy, and coastal living. Once home to the renowned journalist, author, and humanitarian, the property carries a remarkable legacy while inviting its next steward to become part of its continuing story. Thoughtfully updated while preserving its remarkable character, the four-bedroom, four-bath residence is filled with warmth, craftsmanship, and the kind of charm that simply cannot be recreated. Wide-plank floors, hand-hewn beams, period details, and sun-filled spaces speak to generations of care, while thoughtful modern updates offer the comfort and convenience of today's lifestyle.

148 Mungertown Rd, Madison
$537,000
3 Beds ⋅ 2 Baths ⋅ 24189398 MLS
This home is located in the desirable shoreline town of Madison! Nestled on a peaceful 1.12-acre lot, this charming 3-bedroom, 1.5-bath ranch offers the perfect blend of privacy, comfort, and opportunity. Step inside to find a functional, light-filled layout designed for easy one-level living. The spacious living area flows into the kitchen and dining space, creating an inviting atmosphere for everyday living and entertaining. The generous yard provides endless possibilities for gardening, outdoor gatherings, or simply enjoying the tranquil surroundings. Conveniently located just minutes from Madison's beautiful beaches, vibrant downtown, shopping, restaurants, parks, and major commuter routes, this home offers the best of country living with easy access to town amenities. Whether you're a first-time homebuyer, looking to downsize, or searching for an investment opportunity, this property is ready for your personal touch. Don't miss your chance to own a home in one of Connecticut's most sought-after shoreline communities!

371 Race Hill Rd, Madison
$925,000
4 Beds ⋅ 4 Baths ⋅ 24188945 MLS
Situated on over an acre of manicured grounds, this custom-built Colonial blends traditional charm and modern convenience. An inviting front porch welcomes you into a thoughtfully designed floor plan. The main floor flows effortlessly from each room to the next. The eat-in kitchen features stainless steel appliances and sliders to a rear deck. A see-through wood-burning fireplace creates a focal point between the kitchen and formal dining room, while the living room offers a propane fireplace. A full bath and main floor laundry add everyday convenience. The upper level features a primary suite with a walk-in closet - finished with a full bathroom including a jetted tub, a shower and toilet room. An additional generously sized bedroom includes a walk-in closet with access to a full bathroom. Completing the upper level are two more bedrooms, providing plenty of space. The lower level expands the living space with over 1,000 square feet of finished recreation area and bathroom, with walk-out access and stairs leading directly to the three-car garage. Above the garage, a lofted area ensures ample storage. With a newer roof, fresh carpeting, and a newly resurfaced rear deck overlooking the beautiful yard, this maintained home is move-in ready.

706 Green Hill Rd, Madison
$1,200,000
5 Beds ⋅ 6 Baths ⋅ 24187090 MLS
Private.Pastoral.Purposeful. Available for the first time in decades. This rare 4-acre compound offers a Farmhouse style home, a guest house, 3-car garage with additional storage, and attached in-home gym, office equipped with bathroom, and artist's studio. This legacy property delivers both on location and acreage offering a one-of-a-kind sequestered compound that simply cannot be replicated. Level agricultural acreage stretches across the property, bordered by old farm stonewalls. Outstanding potential-whether your vision is a hobby or gentleman's farm, livestock, or equipment storage. Ideal for multi-generational living for those seeking shared but private living. Investors seeking income producing property, entrepreneurial minded, and creatives looking for a home office, in-home gym with full bath, and studio space. The property has two separate septic systems and utilities offering true independence. Farmhouse style home is enchanting with 3-bedrooms. Dual staircases with private access to the primary ensuite bedroom complete with sliding glass doors opening to a private balcony overlooking the serene pastoral landscape. Wide floorboards throughout the main and upper floors. Two enclosed front porches, open covered back patio, solarium, provide additional spaces for hobbies and respite.

1209 Durham Rd, Madison
$564,900
2 Beds ⋅ 2 Baths ⋅ 24182034 MLS ⋅ Kensington Acres North BLDG.
Welcome home to 6 Essex Lane! Elegant and inviting, this meticulously maintained ranch style condo is set in a quiet corner of Kensington Acres North. With a beautiful back patio, you can relax in a peaceful oasis, surrounded by nature. Inside, the expansive living room flows into the dining room, all with lots of light. The gracious kitchen offers quality cabinetry and a granite countertop breakfast bar. From the dining room, head out through the sliders to the three season sunroom that radiates style and charm, you can use it for entertaining and everyday enjoyment. The two bedrooms are generously sized and the primary has an ensuite full bath. If you need storage space, there is an abundance in the attic, accessible via pull-down stairs. A convenient one car garage is just a short walk away. This is a fantastic location only a mile from downtown Madison with its shops, library, cafes, restaurants and train station. And it is an easy drive to the amazing local beaches and Hammonasset State Park. This is shoreline living at its best, come and check it out soon!

6 Essex Ln Unit 6, Madison
$1,378,800
3 Beds ⋅ 3 Baths ⋅ 24185353 MLS
Originally built in 1825, this residence has been thoughtfully updated to preserve its historic essence while incorporating modern conveniences. Nestled on a generous 4.38-acre lot, this extraordinary home boasts 3 spacious bedrooms and 2.5 beautifully appointed bathrooms within its expansive 3,500 square feet of living space. As you step inside, you'll be captivated by the elegant oak hardwood floors that flow throughout. The state-of-the-art kitchen is a chef's dream, showcasing exquisite Calacatta Gold marble countertops and top-of-the-line stainless steel appliances, making it perfect for both casual meals and entertaining guests. Step outside, and you'll find your own oasis featuring an inviting in-ground gunite pool, complete with a pool house, ideal for relaxation and summer gatherings. The vast property offers ample possibilities for subdivision or the construction of an additional home, providing the perfect opportunity for creating a cherished family compound. Additionally, this unique property includes a carriage house with a 3-bay garage with a guest suite above, complete with 2 bedrooms and a full bath, ideal for visitors or as a private office. With its unique character and spacious layout, this home promises to be a tranquil retreat, making it a must-see for those seeking privacy and luxury in an idyllic setting. Don't miss the chance to make this exceptional property your own!

1308 Durham Rd, Madison
$739,000
3 Beds ⋅ 2 Baths ⋅ 24181268 MLS
Picture-perfect English Cape built in 1935, brimming with timeless charm and classic architectural details. A welcoming center-hall foyer features graceful archways leading to the formal living room, where custom built-ins frame the fireplace, and the elegant dining room with its original corner cabinet. It offers a sun-filled kitchen and a family room that opens to a rear deck overlooking a beautiful acre of private grounds. A full bath completes the first floor. Upstairs, three bedrooms are served by a centrally located hall bath featuring a classic tub that reflects the home's period character, with excellent potential for future expansion. The property also includes a detached two-car garage with a heated 350-square-foot studio/office-perfect for working from home, creative pursuits, a fitness space, or a private retreat. Set on a truly special property just 1.5 miles from downtown Madison and its beaches, this exceptional home offers the perfect blend of historic charm, privacy, and convenience.

20 Forest Hills Dr, Madison
$1,299,000
3 Beds ⋅ 3 Baths ⋅ 24181259 MLS
Rare coastal compound opportunity in Madison's highly desirable Seaview Beach area. Situated on approximately one-half acre just moments from the shoreline, this unique property features a main residence and a newer detached accessory dwelling unit, offering flexibility rarely found in one of Connecticut's premier shoreline communities. The main home is clean, functional, and ready for a new owner's vision, while the newer detached dwelling provides additional living space ideal for guests, multigenerational living, rental income, a private home office, or extended family. Separate utilities further enhance the property's versatility. Located within Madison's top-rated school district and surrounded by higher-end homes, this property offers a unique combination of location, flexibility, and long-term potential. Enjoy convenient access to beaches, downtown Madison, restaurants, shopping, marinas, parks, and commuter routes. Whether you're seeking a private coastal retreat, family compound, investment opportunity, or future expansion potential, opportunities like this are increasingly rare. Seller financing available for qualified buyers. Buyer to perform all due diligence regarding future use, expansion, and development opportunities.

32 Liberty St, Madison
$769,000
4 Beds ⋅ 3 Baths ⋅ 24184408 MLS
Set on a beautiful, private 1.25-acre lot in one of Madison's sought-after neighborhoods, this spacious, well maintained Colonial offers exceptional flexibility and comfort with nine rooms plus an additional sunroom. The kitchen is updated with granite countertops and newer appliances. Bathrooms have all been updated with tile and granite. The floors are hardwood throughout the home. Thoughtfully designed for both everyday living and entertaining, the home features generous living spaces, 2 fireplaces and a propane stove, abundant natural light, and a large Great room ideal for a playroom, home office, media room, or guest retreat. Enjoy the peace of mind provided by a whole-house generator, ensuring year-round convenience and security. The picturesque property offers a tranquil setting while remaining just minutes from Madison's town center, walking trails, beaches, schools, shopping, and commuter routes. A wonderful opportunity to make this well-maintained home your own in a premier shoreline community.

89 Summer Hill Rd, Madison
$1,985,000
5 Beds ⋅ 3 Baths ⋅ 24156993 MLS
Welcome to the highly desirable East Wharf area, where this Shingle-Style residence is surrounded by high-value properties. Sited on a generous 3/4-acre lot with a private rear yard and patio, this home offers 2,920 square feet of flexible living space. Step onto the welcoming front porch and into a home designed for comfortable, multi-generational living. The main level is home to a spacious and luxurious primary suite, a rare and highly sought-after feature. The property boasts 5 bedrooms and 3 full baths, providing ample space for family and guests. Adding to the appeal is a versatile studio office space attached to the separate 2-car garage, ideal for a private home business, art studio, or dedicated exercise area. Location is paramount: enjoy nearby beloved East Wharf Beach and the charm of this popular New England shoreline town, placing all of Madison's amenities right at your fingertips. Madison, CT is a shoreline community halfway between NYC and Boston featuring close proximity to rail connections and I-95 .

52 E Wharf Rd, Madison
$850,000
2 Beds ⋅ 1 Baths ⋅ 24183478 MLS
Coastal Paradise in the Heart of Madison! Welcome to one of Madison's most desirable shoreline beach communities, where coastal charm, breathtaking views, and endless outdoor recreation come together to create the perfect seaside retreat. This delightful cottage offers spectacular views of Fence Creek Salt Marsh and a glimpse of Long Island Sound. Kayak or paddleboard from the beach one block away (or directly from the back yard at high tide), enjoy morning walks along the ocean, stroll into town for coffee, and embrace the relaxed Connecticut shoreline lifestyle. Inside, this charming home features 2 bedrooms, 1 bath, and 3 additional rooms that capture the beauty of the surrounding landscape. Large windows invite natural light and showcase the stunning marsh vistas. The deck is ideal for entertaining or simply unwinding while taking in the abundant bird life. After a day at the beach, rinse off in the outdoor shower. Central air conditioning and heat offer three-season living, with the potential for winterization. Its location, just 3/4 of a mile from Madison's vibrant downtown, provides easy access to charming shops (including a renowned bookstore), restaurants, movie theater and library. Ideally situated between New York City and Boston, and approximately one hour from Rhode Island, rarely does an opportunity arise to own a waterfront-adjacent cottage in such a coveted Madison location. Come experience the beauty, tranquility, and timeless appeal of Shoreline Living.

17 Linden Ln, Madison
$570,000
2 Beds ⋅ 2 Baths ⋅ 24183205 MLS ⋅ Windermere West BLDG.
Nicely updated 1476 sf condo with family room, plus 3 season sunporch and full basement. Largest style at Windermere. Living room and dining room are open and have nice hardwood floors. The home has all new windows! Newer kitchen with maple cabinetry. Cozy family room with fireplace opens to a 3 season porch. Off the sunporch is a private patio. There are 2 good sized bedrooms and 2 lovely newer baths. There is a newer furnace, attic and a detached garage. Windermere is a beautifully landscaped complex that is truly park like. Wonderful to take walks and say hello to your neighbors or use the neighborhood kayak launch for a minimal fee. Just 5 minutes to downtown Madison with shopping, restaurants, and sandy beaches.

28 Downing Way Unit 28, Madison
$1,300,000
5 Beds ⋅ 4 Baths ⋅ 24183446 MLS
Welcome to this fabulous one-owner custom home in sought-after Neck River Farms. A gracious, spacious foyer warmly welcomes you inside, setting the tone for the beautifully maintained interior filled with abundant natural light. A dedicated home office with elegant French doors offers the perfect space for working remotely or quiet study. The inviting living room is ideal for entertaining, featuring oversized windows, soaring ceilings, and detailed crown molding. The heart of the home is the well-appointed kitchen, complete with a large center island, generous pantry storage, and granite countertops. It flows seamlessly into the cozy family room, where a wood-burning fireplace creates a perfect gathering space. Upstairs, you'll find 4 bedrooms plus a versatile guest suite above the garage, complete with a full bath and private back staircase-ideal for extended stays or multigenerational living. The primary bedroom is spacious with a luxurious bath and walk-in closet. The finished basement provides additional flexible space for a playroom, fitness area, or media room. Situated at the end of a cul-de-sac, this home offers privacy on 4.12 acres of beautifully landscaped grounds. The level backyard features a lovely stone patio and plenty of room for a pool. Additional highlights include a newer asphalt shingle roof. A rare opportunity to own a spacious and thoughtfully designed home in a desirable location!

77 Silo Hill, Madison
$605,000
2 Beds ⋅ 3 Baths ⋅ 24178470 MLS ⋅ Windermere East BLDG.
One person's loss is another one's gain! You have a second chance to make this this lovely property yours. It is more than a home --it's a lifestyle. Tucked into one of Madison's most sought-after communities at Windermere East, you'll feel at home the moment you enter the front door. The bright, open floor plan provides casual, coastline living at its best. The remodeled kitchen with granite counters, island and stainless appliances opens to the combination dining area and living room with its cozy gas fireplace. The primary bedroom has an ensuite bathroom, and you also have a second bedroom and full bath on the main level. The lower level provides additional living space for office, exercise or relaxation plus an area for a guest bedroom with a 3rd full bath and is heated by electric baseboard. For three seasons of the year, you'll love sitting out on the enclosed porch; or in the summer, you can dine al fresco on the charming private patio with its ivy-draped arbor. Madison residents enjoy access to town beaches including Hammonasset Beach State Park. The historic town center is a great place to stroll and stop in at a bookstore or outdoor cafe and watch the world go by. This property is ideal for anyone looking to enjoy a more relaxed lifestyle.

5 Thelbridge St Unit 5, Madison

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