Refine Search
Map
Sort by
$693,000
3 Beds ⋅ 3 Baths ⋅ 24093316 MLS
Please have all offers in by Tuesday at noon. Tucked away at the end of a peaceful cul-de-sac in Madison, this impeccably maintained three-bedroom home offers both comfort and charm in equal measure. Set on a generous, beautifully landscaped lot, the property boasts a spacious yard perfect for outdoor living, gardening, or simply relaxing in your own private oasis. Step inside to discover a home that reflects thoughtful care and quality throughout. The inviting floor plan features multiple built-ins, ideal for both storage and display, as well as a sun-drenched screened-in porch-perfect for enjoying your morning coffee or evening breeze, mosquito-free. The expansive primary suite is a true retreat, complete with a full en-suite bathroom and a walk-in closet. Whether you're looking for peace and privacy or room to entertain, this home offers it all in a highly desirable Madison neighborhood. Don't miss your chance to own this move-in-ready gem with timeless appeal and exceptional upkeep.

68 White Cedar Dr, Madison
$692,500
4 Beds ⋅ 4 Baths ⋅ 24033735 MLS
Stunning Colonial home tucked away on a beautiful private lot in sought-after North Madison Brians Knoll subdivision. This is a well cared for property with many updates. Open floor plan with a gorgeous granite stainless kitchen, family room with cathedral ceilings + fireplace, formal living room, dining room, finished lower level walkout basement (ADDITIONAL 1138 SQ. FT) providing natural lighting, the lower level has many uses and features a private full bathroom, office, mud room, and additional room... perfect for a your home office, in-law suite, nanny's quarters, hobbyist, and/or home gym. Upstairs, you will find four large bedrooms, pretty bathrooms, generous closets, and huge walk up attic for storage. Nature lovers will delight in this private natural setting that is nicely landscaped showcasing the dramatic multi level expansive backyard deck. Great area to walk or hiking the trails of Rockland Preserve. Drive to downtown and stroll the charming New England village shops, dining, and town green. Spend the day at the beach... Hammonasset & Chatfield Hollow state parks or the town Surf Club. Situated between NYC and Boston. Don't miss your chance. Expect multiple offers.

67 Devonshire Ln, Madison
$690,000
4 Beds ⋅ 4 Baths ⋅ 24106075 MLS
Welcome to this spacious and versatile Colonial home located less than 2 miles from charming downtown Madison, CT. With 4-5 bedrooms, 3.1 baths, and three fireplaces, this home offers the perfect blend of classic elegance and modern functionality. The large living room with fireplace is ideal for gatherings, while the inviting family room features built-in cabinetry, bookshelves, a cozy fireplace, and a slider that opens to an expansive deck-perfect for entertaining or relaxing in nature. A third fireplace adds warmth to the finished walkout lower level. Sunlight fills the home through energy-efficient thermopane windows, enhancing the beauty of the hardwood floors found throughout. The renovated kitchen is a chef's delight with rich wood cabinetry, granite countertops with ogee edges, a stylish tile backsplash, and a spacious pantry with pull-out drawers. Enjoy meals in the sunny eat-in area with a bay window that overlooks the backyard's natural beauty. Upstairs, you'll find four generously sized bedrooms, including a primary suite with tiled shower and glass door. A pull-down attic offers extra storage. The finished lower level includes a full bath and flexible living space with its own entry-ideal for in-laws, an au-pair, home business, or guest suite. There's a 5th bedroom/office and even a hook up for a wet bar. Central Air and Generator hook up are additional great features! The Madison shoreline has access to sandy beaches, shops, restaurants and the good life!

41 Sportsman Hill Rd, Madison
$690,000
4 Beds ⋅ 2 Baths ⋅ 170591915 MLS
Location, location, location! Nestled within the picturesque beach community of Madison, this charming cape-style home offers both tranquility and convenience. The house was literally taken down to the studs and completely renovated and updated in 2013 but keeping all its original charm and character. With its open floor plan, four bedrooms and two full baths, large backyard and deck, it provides ample space for for entertaining family and friends. Situated at the end of a private lane, the residence provides a sense of seclusion, allowing for peaceful enjoyment of its surroundings. Its location, equidistant between the bustling cities of Boston and NYC, offers the best of both worlds - a serene coastal retreat that's also well-connected to urban pursuits. Whether you are relaxing on the beach that is just a short walk away or strolling or biking to the village shops and restaurants, browsing the Farmers Market or attending a concert on the Town Green, this home is the perfect blend of coastal living and NYC and Boston metropolitan accessibility, with ample and reliable train service and airports in convenient proximity. Please refer to upcoming Open Houses...

18 Pepperidge Ln, Madison
$690,000
4 Beds ⋅ 3 Baths ⋅ 24127039 MLS
This is the Madison home you have been waiting for!! Tucked away on 1.88 acres of level land in one of the area's most beautiful neighborhoods, this 4-bedroom colonial offers the perfect blend of privacy & convenience. Inside, natural light floods the home through skylights and oversized windows. The dramatic two-story entry opens to a bright living room with soaring ceilings, creating an immediate sense of space and comfort. The living room flows seamlessly into a generous dining room, ideal for gatherings. Just off the dining room is a versatile sunroom that can be used as a playroom or home office. The updated kitchen is the heart of the home, offering granite counters, plenty of cabinetry, newer appliances, and both a breakfast bar and casual dining area. The adjoining family room features a wonderful fireplace and sliders to a spacious deck that overlooks an amazing fully fenced in yard with a spacious shed. Upstairs, four well-sized bedrooms include a primary suite with a spa-like bath, phenomenal closet space, and a separate dressing room with laundry. The fully finished lower level adds 800+ sq ft of flexible space that even includes a wet bar. With a new water heater, water filtration system (that goes into a private drywell!) this home is move-in ready. Central air as well. This incredible neighborhood offers access to the Madison trail system. A rare opportunity in an exceptional location-don't miss it.

42 Buck Hill Rd, Madison
$685,000
5 Beds ⋅ 3 Baths ⋅ 24175082 MLS
Beautifully maintained and ideally located, this 2200 sq.ft raised ranch features modern updates and a flexible, spacious floor plan throughout. On the main level, the open-concept living area flows seamlessly into the dining room, characterized by abundant natural light and gleaming hardwood floors. The updated kitchen is equipped with stainless steel appliances, Corian countertops, and a center island. From the dining room, sliders lead to a new AZEK deck, providing an ideal space for outdoor entertaining. The hall bath has been beautifully remodeled with new tile flooring and custom tile surround. This floor includes four bright bedrooms with ample closet space, including a primary suite with a full ensuite bath with stall shower. The lower level offers a generous family room with fireplace and sliders opening to a new custom patio, along with a third full bath and a fifth bedroom, currently utilized as a home gym. A walk-out to the two-car garage completes the space. The home boasts extensive recent upgrades, including a new roof (2020), new siding and plywood (2021), a new well pump and tank (2021), an upgraded 200-amp electrical panel (2021), a new driveway (2023), and new walkways and patio (2024). With a new dryer and refrigerator installed in 2026, this home is entirely move-in ready. Experience the best of Madison, from the Surf Club and town beaches to Hammonasset State Park, local shopping, and the top-ranked school system. This is an opportunity not to be missed

10 Scenic Rd, Madison
$680,000
4 Beds ⋅ 3 Baths ⋅ 24010139 MLS
There is so much to admire when considering this immaculate 4-bedroom, 2.1-bath Colonial, beginning with its ideal location. Situated on nearly 2 wooded acres, the home has plenty of privacy, yet it's minutes from downtown Madison, shopping, movie theater, beaches and schools. The house itself has many distinct qualities, including hardwood flooring and crown molding throughout. The main floor flows from the living room into the dining room, featuring a unique tray ceiling and recessed lighting. The adjacent kitchen has been updated with granite countertops, stainless-steel appliances, two pantries, center island/breakfast bar and eat-in area. This leads to the sunny family room, with a raised-hearth gas fireplace, customized mantel and sliders that open onto a wood deck and stone patio overlooking the professionally landscaped backyard and surrounding woods. This level also has a half bath and access to the two-car garage. Upstairs, the lovely primary bedroom has a vaulted ceiling and skylight, double closets and private full bath. The other three bedrooms - one with access to the walk-up attic - share a full bath with a tub and shower. The lower level has flexible space with a rec room (ideal for a home gym), home office, workshop/art studio, laundry room and utility room. Other amenities include natural gas, central AC, a whole-house generator, newer roof and driveway.

40 Overbrook Rd, Madison
$680,000
5 Beds ⋅ 4 Baths ⋅ 170617206 MLS
Welcome to this exquisite fully remodeled Colonial nestled on a generous .92-acre lot in the town of Madison. Located just 15 minutes away from Hammonasset Beach & easy access to New Haven, Old Lyme, Hartford, Casinos & Misquamicut Beach all within less then 1 hour away. The main house welcomes you with an inviting front porch that brings you into the semi-open concept layout w/ gleaming hardwood flooring that runs throughout. The main level provides 2 wood-burning fireplaces & recessed lighting. Eat-in kitchen boasts quartz countertops, stainless steel appliances, ample cabinetry space & large center island with breakfast bar. including a primary bedroom featuring a walk-in closet & on-suite full bath. The detached cottage is a true gem. W/ 1 bedroom, 1 bath, a laundry room, kitchen & a combination living room/dining room the cottage provides a perfect private in-law apartment. Sharing the well & electric service, including a hard-wired generator w/ the main house, the detached cottage also features a separate septic system. Whether you are captivated by the thoughtfully designed main house or enticed by the possibilities offered by the detached cottage, this property promises a lifestyle of comfort & convenience. Embrace the tranquility of Madison while enjoying easy access to beaches, vibrant cities & entertainment destinations.

579 Opening Hill Rd, Madison
$680,000
4 Beds ⋅ 3 Baths ⋅ 24008436 MLS
Situated minutes from the picturesque shoreline village of Madison, this custom-built Cape has been meticulously maintained by only 2 owners over 25 years. Positioned at the highest point on 2 acres, it exudes charm and comfort. An inviting front porch welcomes you and upon entering you're greeted by the warmth of cherry hardwood floors. The open-concept main level encompasses a spacious family room and well-appointed kitchen equipped with stainless steel appliances, granite countertops, and ample storage. Adjoining the kitchen is a light-filled breakfast nook for daily meals, a formal dining room awaits larger gatherings and holiday feasts. The family room, with a wood-burning fireplace, is a retreat for relaxation and a roomy carpeted living room features sliders to a deck. Rounding out the main floor are an office, powder room and laundry area. French doors add privacy to several rooms. On the 2nd floor are all 4 bedrooms: a primary suite with 2 walk-in closets and a newly remodeled ensuite bath, 3 additional family/guest rooms and a recently updated hall bath. Step outside and the patio and deck are ideal for entertaining guests in the secluded and expansive backyard with ample room for outdoor activities. A hot tub beckons throughout the year. Located only 10 minutes from the town center, beaches, highways and commuter rail, this home provides the perfect balance of accessibility and tranquility. New York City and Boston are just 2 to 2.5 hours away by train and car.

68 Old Toll Rd, Madison
$680,000
4 Beds ⋅ 3 Baths ⋅ 24089708 MLS
This spacious Cape-style home with a modern twist offers over 3,000 sq ft of thoughtfully designed living space-plus an additional 300 sq ft finished rec room in the basement. The heart of the home is the expansive kitchen, featuring granite countertops, a center island with a built-in microwave drawer, and premium stainless steel appliances including a Wolf 6-burner dual fuel range, Viking double-door refrigerator, and Bosch dishwasher. The tiled mudroom and second staircase leading to a versatile bonus room (perfect home office, playroom, or home gym!) add function and flexibility. A standout feature is the well-designed in-law suite, added in 2004, offering endless possibilities-use it as a private guest space, home office, au pair suite, or even a luxurious first-floor primary. The suite has its own exterior entrance as well as access through the main family room. Natural light fills this open-concept home, enhanced by vaulted ceilings, skylights, and two fireplaces-one propane and one wood-burning-for year-round comfort. Upstairs, you'll find three bedrooms, including the primary suite and an updated full bath. Don't miss this exceptional property that blends classic charm with contemporary features, all just minutes from town, top-rated schools, beautiful beaches, and convenient commuting options.

76 Horse Pond Rd, Madison
$679,000
5 Beds ⋅ 4 Baths ⋅ 170579845 MLS
Be part of Madison's history in this renovated 1747 colonial home built by Captain Frederick Lee, father of the United States Coast Guard. This center chimney colonial home enjoys the many upgrades of the 21st century while still retaining the charm of the period. You will enjoy 5 fireplaces, one with a bee hive oven allowing for open hearth cooking, Guests can gather in the Armory with a large fireplace and wide plank flooring which was used during the war of 1812. The armory leads to a large three season porch that allows you to enjoy the beautiful grounds. This home also enjoys an addition that would be perfect as a in-law area, office space or studio. It has its own private entrance. The 3,318 square feet will allow you to customize the twelve rooms to your needs and/or your dreams. The home enjoys energy efficient natural gas heat, city water, a renovated kitchen keeping the charm of the period in place, a new roof and replacement or repair of exterior trim(2023), and repair of the central chimney (2023), The location will allow you to enjoy Madison's fine beaches, Madison CC, The village Green , plus train service to New York and Boston along with easy access to I-95 or L-91. Live in the Captain Frederick Lee home and be a part of history.

273 Boston Post Rd, Madison
$675,000
4 Beds ⋅ 2 Baths ⋅ 24182189 MLS
Welcome to 94 Warpas Road, a carefully maintained Cape-style home on a picturesque 1-acre lot in one of Madison's most desirable locations. This 4-bedroom home blends classic New England charm with modern updates. Situated directly across from protected land trust property with hiking trails, you'll enjoy peaceful views and the assurance that no homes will ever be built across the street. The flexible floor plan features a sought-after first-floor primary bedroom, while the second floor offers an additional primary suite option with a spacious walk-in closet. The partially finished lower level includes a custom-built bar and dedicated exercise room (not pictured). Step outside to your private backyard retreat, complete with pristine landscaping, a screened-in porch, expansive deck, and swimming pool. Whether hosting summer gatherings or enjoying a quiet morning coffee, the outdoor space feels like a private resort. Major updates include: A new roof, solar panels, and most windows (2020); LeafFilter gutter protection (2022); new water pump (2023); new deck (2024); new oil tank (2025); and new electrical panel, generator connection switch, and upstairs AC split units (2026). First-floor central air was installed in 2017. These substantial upgrades offer buyers the rare opportunity to move into a home where many major systems have already been addressed. Conveniently located just minutes from Madison's beaches, downtown shops, restaurants, and schools.

94 Warpas Rd, Madison
$675,000
2 Beds ⋅ 2 Baths ⋅ 24135115 MLS ⋅ Windermere West BLDG.
Large ranch unit with views of the Hammonassett River from several rooms and the brick-walled patio. Full basement, partially finished with huge amount of storage. Open floor plan living room and dining area, leading to the family room with gas fireplace & built-ins. Family room has sliders to 3 season porch with supplemental electric heat, which leads to a lovely brick walled patio overlooking the Hammonassett River. Neat and clean unit! Association fee is $615/month, Land Lease is $125/month, and there is a one-time buy-in fee of 1/2% of purchase price due at closing. Inside pictures avail Nov 1

28 Aylesbury Cir Unit 28, Madison
$675,000
3 Beds ⋅ 2 Baths ⋅ 170596480 MLS
This Charming 1860 Antique home is the ideal country setting with all the conveniences of today. Just a short walk to Madison’s stunning coastline, beaches, the Greenway Trail and just a 2-minute drive to the historic town center. The main house with lovely living space has maintained many of the original details to this historic home. The second floor hosts the primary bedroom and a full bath. The 3rd floor has 2 additional bedrooms. A one-of-a-kind detached 2 car garage with studio space above and beautiful windows could potentially be converted to a carriage house accessory apartment, art studio or private workspace. The property has gorgeous stone outcroppings and seasonal views of Long Island sound. Natural gas, city water, Central Air and no flood insurance required. A charmer for sure with so much to offer.

107 Signal Hill Rd, Madison
$674,900
3 Beds ⋅ 2 Baths ⋅ 24024760 MLS
Location! Location! Location! This adorable Cape has been beautifully renovated and is ready just for you! Part of the Lee Manor Beach Association, with Beach Rights, enjoy spending quiet "toes in the sand" time at this private beach just down the street! Go for a swim, or relax under your beach umbrella with a good book for summer reading. Upon entering the home, you will be graced with charm and natural light. The first floor boasts an open concept with living room (wood burning fireplace)/dining room open to a brand new kitchen with NEW stainless appliances, and soapstone counters, coffee bar area, as well as a french door out to the pleasant fenced-in flat yard. Low maintenance white cedar pines line the back fence for natural privacy. There is also a first floor office/guest room with a murphy bed. Perfect for those casual weekend guests. Also on the first floor is a laundry/mud room and a French door out to a small rear deck overlooking the backyard. Adjacent to the laundry/mud room is a brand new full bath with subway tiled tub/shower combo and HEATED floors! First floor has luxury vinyl and the second floor bedrooms are freshly carpeted. The second floor consists of two bedrooms with custom built ins and tall vaulted ceilings as well as a NEW half bathroom and walk-in linen closet. Just in time for summer fun! Note: Also listed as a Rental. See MLS#24025550 & #24025551.

26 Taylor Ave, Madison
$670,000
4 Beds ⋅ 3 Baths ⋅ 24058077 MLS
OFFERS RECEIVED. PLS SUBMIT HIGHEST AND BEST BY 5:00PM MONDAY, 11/11. THX YOU! Nestled on a peaceful cul-de-sac off of Opening Hill Rd. called Forest Edge, this lovely 4-bedroom colonial offers the perfect blend of style and functionality. The spacious kitchen features beautiful granite countertops, stainless steel appliances, and an inviting center island, making it ideal for both cooking and entertaining. The adjacent family room is a warm and inviting space with a vaulted ceiling and a stunning floor-to-ceiling stone fireplace as its focal point. Just off the family room, a bright sunroom provides a serene spot to relax or enjoy your morning coffee. Upstairs, you'll find four generously sized bedrooms, including the primary suite with a private bath for added comfort and convenience. This is a walk-up attic which is great for storage or future expansion potential. Hardwood floors run throughout the main level, enhancing the home's timeless appeal. The private, level yard features a charming patio, perfect for outdoor dining or unwinding in the peaceful surroundings. Additional features include a 2-car garage and all-new roof and windows, offering peace of mind and modern efficiency. Conveniently located near top-rated schools, Madison Village, and the area's stunning beaches, this home is truly the complete package.

218 Opening Hill Aka Forest Edge Rd, Madison
$670,000
4 Beds ⋅ 3 Baths ⋅ 24092652 MLS
Elegant Colonial on Pristine Corner Lot. Nestled on a generous 1.34-acre corner lot in the charming town of Madison, CT, this exquisite 4-bedroom, 2.5-bath colonial home offers a harmonious blend of comfort and outdoor space. The property's curb appeal is immediately apparent with a stone wall & garden area (backyard) and newer walkway to the front door. As you step inside, the entire interior welcomes you with a fresh coat of paint & newer moldings. The addition of hardwood floors in the Family Room and upstairs hallway enhances the home's warmth and continuity. The heart of the home, the Family Room, with a gas fireplace and slider access to the backyard, is a cozy retreat with ample space for relaxation and family gatherings. The kitchen overlooks the new backyard patio, perfect for outdoor entertainment amidst the backdrop of your garden oasis. In the Primary Suite, you'll find a fully renovated bath. The additional 3 other bedrooms provide comfortable accommodations for family and guests, sharing a hallway full bath. Noteworthy features: dual-zone central A/C system, UV water filter and a new tank, new fridge and dishwasher. This home is a true gem, offering a blend of traditional charm with a central location in the Town.

5 Dover Ln, Madison
$667,000
2 Beds ⋅ 3 Baths ⋅ 24055377 MLS ⋅ East River Farms BLDG.
Step into luxury and elegance in this exquisite townhouse located in East River Farms in Madison. Completed in 2017, this newer construction boasts 9-foot ceilings and gleaming hardwood floors throughout, creating an airy and sophisticated ambiance. Custom upgrades, such as sleek black metal railings on the stairwell, add a touch of modern artistry. With a bedroom suite including a full bath on the first floor, the home was thoughtfully designed for true one-level living. The main level bath is a sanctuary of relaxation featuring a soaker tub, a walk-in shower, and radiant floor heating for added comfort. On the upper level you'll find a second primary suite with a full bath, along with a versatile room perfect for a den, office, or guest room. The heart of the home is the kitchen with granite countertops and stainless-steel appliances, seamlessly flowing into the open concept living and dining areas. Step outside to your private patio, enclosed on three sides with fencing and shrubbery creating a serene courtyard feel ideal for relaxation and entertaining. With city water, natural gas, and a whole house generator, this home combines luxury with practicality, offering a lifestyle of ease and sophistication. Madison is the quintessential coastal town known for its picturesque beaches including Hammonasset Beach State Park, a vibrant downtown featuring iconic shops and restaurants, concerts and farmers' markets on the town green, natural beauty, and lively spirit. This is home!

67 Boston Post Rd Unit 7, Madison
$665,100
4 Beds ⋅ 3 Baths ⋅ 24035869 MLS
Move right into this stunning, updated turn-key property that offers both privacy and convenience along the Connecticut shoreline. With 4 BR and 2.5 bathrooms, this home is close to downtown shopping, restaurants, schools & beaches. It sits nicely on just under an acre with mature flowering plantings and a fantastic fenced garden with raised beds. Welcome! Just through the foyer, the formal living room, currently used as a dining room is gracious and sunfilled. The modern kitchen, which overlooks the nicely landscaped yard, features Carrera marble counters, a large breakfast bar, and newer stainless appliances including a Viking range. Just off the kitchen is the living room, with woodburning fireplace and sliders onto the deck, perfect for easy entertaining! Wander back through the kitchen past the breakfast bar and into the den/dining area, an open and comfortable floorplan. Up the stairs, you'll find a roomy primary suite with hardwood floors and lovely custom board and batten feature wall. This spacious suite has a spa-like ensuite and a walk-in closet. Three additional bedrooms on this level each have hardwood floors and large closets. The lower level offers a large room, perfect for a home office, exercise room, or a media oasis. The laundry and mechanicals are on this level as well. The park-like grounds are perfect for entertaining.

158 Scotland Rd, Madison
$665,000
3 Beds ⋅ 2 Baths ⋅ 24130448 MLS
Enjoy endless beach days from this charming 3-bedroom, 2-bathroom Cape retreat. Entertaining is easy with the open floor plan design, large patio, and generous yard space ideal for outdoor gatherings. The primary bedroom is conveniently set on the main floor, and 2 additional bedrooms and one full bath are upstairs. Perfectly suited for one-level living, seasonal getaways, or a permanent shoreline residence! Association Beach is at the end of the street.

18 Kelsey Pl, Madison
$664,600
4 Beds ⋅ 2 Baths ⋅ 24127710 MLS
This storybook Cape is a hidden treasure, offering 2,000 sq. ft. of character-filled living space plus a heated 975 sq. ft. studio-ideal for work, art, or guests. At its heart lies a true culinary centerpiece: an epicurean's dream kitchen with a 6-burner range, custom finishes, and timeless details that anchor the open floor plan. The main level continues with a welcoming living room and cozy stone fireplace, a private office, first-floor bedroom, full bath, and an oversized mudroom. Upstairs, three additional bedrooms and another full bath provide comfort and flexibility for family or guests. The Studio barn adds to its appeal, with two finished stories offering endless opportunities-from expanded living space to a potential in-law suite. Blending timeless character with modern updates and versatile spaces, this property is more than a home-it's a unique treasure in today's market.

735 Opening Hill Rd, Madison
$662,500
3 Beds ⋅ 3 Baths ⋅ 24000367 MLS
Nestled amidst the tranquil embrace of natural splendor, this exquisite Madison home epitomizes serenity on its expansive 1.35-acre lot. This meticulously maintained center hall colonial spans 2,420 sq.ft. of living space. At the heart of the home lies a chef's kitchen w/a central island boasting a SS Viking gas cooktop & hood, as well as a dishwasher, double wall oven, & SS fridge. Beyond the FR is a cozy gas fireplace, framed by double glass doors leading to the outdoor deck, while a sprawling bay window invites picturesque views of the natural landscape. Entertain in the spacious DR or enjoy the quiet comforts of the formal LR. Completing the main level is a convenient half bath & foyer. 2nd level offers primary BR w/an ensuite bath & generous walk-in closet. 2 add. spacious BRs, office, hallway full bath, & 2nd-level laundry. LL presents 1,187 sq.ft. of unfinished potential w/a walk-out door. Walk up attic, offering an add. 1,187 sq.ft of unfinished space. Other features include, central AC & pushed heat for the main 2 levels & the LL, oversized attached 2-car garage, new GAF Golden Pledge Warranted Roof w/new seamless gutters, freshly painted interior & outdoor shed. Embrace a lifestyle of leisure & exploration, w/nearby attractions including the Rockland Preserve, offering biking & hiking trails, Lake Quonnipaug, & Hammonasset Beach. Settle into the embrace of nature's beauty & make this magnificent home in the charming town of Madison, CT, your cherished haven.

98 Dorset Ln, Madison
$660,000
4 Beds ⋅ 2 Baths ⋅ 24168790 MLS
Light, bright, and full of potential, this appealing home is ideally located close to everything Madison has to offer. Set on a level corner lot, the property offers flexibility, visibility, and multiple possibilities for outdoor living or future enhancements. Just 1-2 miles to everything important that Madison has to offer like East Wharf Beach, I95, the Shoreline Greenway Trail, Hammonasset State Park, Surf Club, Madison Country Club, Arts Cinema, downtown Madison, the train station, and a wide array of restaurants and shops. Recent improvements include a new roof, a new bay window in the living room, new carpeting in the lower level, and newer mechanicals, providing peace of mind for the next owner. Inside, a spacious and airy all season sunroom off the kitchen and dining area adds wonderful additional living space filled with natural light. The lower level features an in-law apartment with potential for a fifth bedroom, ideal for multigenerational living, guests, or added flexibility. Laundry hookups are available on both floors. This is an excellent opportunity purchase in a highly desirable location.

6 Yankee Peddler Path, Madison
$660,000
3 Beds ⋅ 3 Baths ⋅ 24163798 MLS
This charming, meticulously maintained 3-bedroom, 2.5-bath home offers exceptional quality and pride of ownership throughout. Features include central air and a walk-out basement that backs up to beautiful open space, providing both privacy and scenic views. While some finishes reflect a classic style, the home is in outstanding condition-spotlessly clean and truly move-in ready. Beneath the wall-to-wall carpeting lies pristine, never-used hardwood flooring, offering additional potential for customization. Highest and Best Friday April 10th at 9am

370 Opening Hill Rd, Madison
$660,000
4 Beds ⋅ 2 Baths ⋅ 24160434 MLS
Highest & Best due for April 1st - 12:00 Noon Discover the perfect blend of warmth, character, and lifestyle in this inviting four-bedroom Cape, ideally situated on a quiet street just minutes from Madison's Town Center and pristine beaches. The sun-drenched living room features an oversized front window and cozy wood-burning fireplace. Flow seamlessly into the dining room, sized beautifully for gatherings of any size. The updated kitchen boasts granite countertops, tumbled marble backsplash, and a functional center island, all open to the dining area. Step into the bright sunroom-your new favorite retreat-overlooking the deck, pool, and lush backyard. The convenient first-floor primary bedroom and full bath complete the main level, offering single-floor living potential. Upstairs, three additional bedrooms with gleaming hardwood floors and generous closets share a full bathroom. The finished lower level recreation room expands your living space, while the large utility area offers workshop, gym, or storage possibilities. The private, expansive rear yard features an in-ground pool, garden beds, and plenty of open space. The detached two-car garage provides ample parking and storage. Owned solar panels keep utility costs remarkably low-averaging under $20/month in summer. Minutes to beaches, town center, and I-95. This Cape offers comfort, character, and convenience in one of Madison's most desirable settings.

19 Green Acres Dr, Madison
$660,000
2 Beds ⋅ 2 Baths ⋅ 170606517 MLS ⋅ Deer Creek BLDG.
This stunning Madison home is a harmonious blend of Southern charm and elegance. Located in a 13 home private and extremely desirable association of free standing single family homes. As you step through the grand front door, you are greeted by soaring, vaulted ceilings adorned with skylights, creating a sense of openness and light reminiscent of Hilton Head or Charleston architecture. The open-concept kitchen, featuring custom mahogany cabinets, seamlessly flows into the living room with fireplace, connected by elegant French doors that lead to a dramatic glassed sunroom bathed in natural light. The formal dining room features a tall palladium window. The primary bedroom suite has a huge walk-in closet and bathroom. Additional living space is provided downstairs in the finished basement which is perfect for an additional family room, exercise room or home office. If that were not enough space there is a bonus room above the garage! The terrace allows you to take in the private rolling backyard featuring exquisite landscaping, gardens and a koi pond with waterfall. This beautiful home offers both spaciousness and grace, perfect for those seeking a touch of Southern-inspired living in New England.

14 Deer Creek Dr Unit 14, Madison
$660,000
2 Beds ⋅ 2 Baths ⋅ 24060850 MLS ⋅ Windermere West BLDG.
Don't miss this extraordinary opportunity to own a pristine stand-alone ranch unit in the highly sought-after Windermere community. This exceptional home boasts the best location in the complex, featuring panoramic views of the tidal Hammonasset River & its surrounding salt meadows from every room. This spacious residence has undergone beautiful renovations, showcasing an open floor plan. The living room, complete with a cozy gas fireplace, flows into the renovated kitchen, which features quartz countertops, a tile backsplash, stainless steel appliances, a center island, & a generously sized dining area. Heated sunroom with expansive walls of glass that provide views of the landscape and abundant wildlife. This charming space leads out to a spacious stone patio. Both bathrooms have been updated, featuring heated floors, with the main bath equipped with a washer and dryer. The primary bedroom has sliding doors that lead to a private patio area, offering serene views through both the window & the sliding door, along with an en-suite bathroom. The unit also includes a generously sized guest bedroom and custom flooring throughout. A newer hydro air heating system ensures comfort year-round. Just a short walk from the HOA kayak racks, this unit provides direct access to the river. The complex's address on Salt Meadow Park offers easy access to the beautiful trails of Hammonasset State Park. This unit represents a unique opportunity for years of enjoyment in a picturesque setting!

19 Canborne Way Unit 19, Madison
$660,000
2 Beds ⋅ 2 Baths ⋅ 24067591 MLS
Beautiful detached end unit ranch in Windermere West now available! One of the few condos with a full basement and extra room set up as an office with built ins. Seller put in new golden teak flooring and remodeled both bathrooms. Just a few minutes to Hammonasset State Park, Madison Village with restaurants, shops, library, world renowned RJ Julia Book Store and town beaches. One car garage is steps away

11 Downing Way Unit 11, Madison
$660,000
2 Beds ⋅ 3 Baths ⋅ 170626887 MLS ⋅ Legend Hill BLDG.
Introducing this 2-bedroom, 2.5-bathroom listing with over 2400 square feet of luxurious living space. Enjoy the breathtaking panoramic views of Long Island Sound from the comfort of your new home. This meticulously maintained property features a range of upgrades, including elegant wood flooring throughout, renovated bathrooms, a cozy gas fireplace in the living room, and a modernized kitchen adorned with granite countertops and stainless steel appliances. Indulge in the versatility of the winterized screen porch with new windows, seamlessly transformed into either a charming dining room or a cozy den. Guests are treated to a private haven in the finished basement, perfect for overnight stays. The property also offers access to amenities such as a meticulously restored mansion serving as a clubhouse, tennis and pickleball courts, and a large swimming pool. Enjoy the convenience of a two-car garage, complemented by a recently repaved driveway. Discover more about the intriguing history of Legend Hill by following the provided link.

263 Legend Hill Rd Unit 263, Madison
$660,000
2 Beds ⋅ 3 Baths ⋅ 170593748 MLS ⋅ Kensington Acres North BLDG.
WANTED: A DISCERNING BUYER WHO WILL APPRECIATE OVER $350,000 + IN UPGRADES made to this Exceptional, Light-filled End Unit Townhouse. The entire interior has been remodeled giving a whole new meaning to open concept. The blend of style and functionality lends itself to the tranquil vibe. All the luxury amenities create a unique value not found in any other unit. The primary bathroom is like no other ~~on demand steam, 12 showerheads, adjustable mood lighting and music, Robern Uplift adjustable vanity cabinet including recessed lighting and defogger. Savor the best of both indoor and outdoor living minutes to beaches, restaurants, world famous RJ Julia Bookstore, library, train and commuter routes. Just turn the key...

9 Strathmore Ln Unit 9, Madison

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.