Refine Search
Sort by
$880,000
2 Beds 2 Baths 24183654 MLS
Turn down a long, picturesque driveway to a stunning mid-century cape, unseen from the roadway. Note, the spectacular fieldstone chimney on the large addition of the gable-end plus the closed in screened porch to the west. Ahead you'll find a large, detached 2-car garage and off to the south a small barn with great potential for an equestrian opportunity. From the screened in porch, enter the house thru its French doors. The field stone fireplace is a match to the exterior chimney. The semi-circular staircase rises to an upstairs reading room with its own fireplace and just off the primary bedroom. Both the reading room and bedroom enjoy the added light of angle-mounted skylights. Walking to the south, you'll pass the upstairs full bath, a second staircase, another full bedroom, and a study at the end of the hall. Take the traditional staircase back to the first floor and step into the foyer by the front door. Turn either left into a large, fully-equipped eat-in kitchen or turn right into a magnificent full-width dining room with a large, central fireplace with multiple windows on 3 sides over-looking the estate's grounds. Walk outside the house and turn to the west to see the well-maintained rolling acres before you. This is a lovely, well cared for private home on a very beautiful 7+ acre lot.

2415 Durham Rd, Madison

$635,000
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

$595,000
2 Beds 2 Baths 24160683 MLS Windermere East BLDG.
Nestled in the highly sought-after Windermere East community, this rare free-standing condo offers the perfect blend of privacy, comfort, and coastal charm in beautiful Madison. Enjoy serene river views and a peaceful setting just moments from the shoreline. This well-maintained home features 2 bedrooms and 2 full baths, a spacious fireplaced living room, and a bright kitchen ideal for everyday living. The new HVAC system with gas heat and central air ensures year-round comfort and efficiency. A lovely 3-season sunroom that offers additional living space and opens to a private patio-perfect for relaxing, entertaining and enjoying the view of the river. Ideal for kayaking right from your backyard, with space to conveniently store your kayak onsite. A standout feature of this unit is the full basement-an uncommon find in the complex-offering abundant storage, a cedar closet, and partially finished space with endless possibilities. Ideally located within walking distance to Hammonasset Beach State Park and scenic walking trails, and just minutes to marina's and downtown Madison where you'll find fine dining, a charming movie theater, shops and the beloved RJ Julia Booksellers. Enjoy the best of shoreline living in one of Madison's most desirable communities-an ideal choice for those looking to downsize or create the perfect coastal escape.

10 Runnymede Ln Unit 10, Madison

$574,000
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

$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

$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

$500,000
2 Beds 2 Baths 24200381 MLS Windermere East BLDG.
Step out of the 3 season, enclosed porch to the private park-like grounds of this ranch-style condo in Windermere East. This home has been tenderly cared for and is ready to welcome its next owners to enjoy. The main living areas offer a nice open floor plan, combining the living and dining areas. Both bedrooms are large enough to accommodate a king-size bed or two twin beds. There are two full bathrooms with stall shower in guest bath and a full-size washer and dryer. The electrical/solar system in this unit results in unbelievably low utility bills. The desirable location is with in an approximate 5 to 6 minute drive to the center of town where one will find shopping, the library, restaurants, the seasonal Friday afternoon Farmer's Market on the Town Green as well as several cultural events, including concerts, fairs, and art exhibits. In addition to nearby Hammonasset State Park, this home is just minutes from Madison's three resident beaches. The local train station provides commuter service to New Haven where one can connect to a two-hour train ride to NYC.

22 Thelbridge St Unit 22, Madison

$489,000
2 Beds 3 Baths 24203806 MLS Esterly Farms BLDG.
Welcome to 23 Esterly Farms, an exceptional end-unit townhouse offering the perfect blend of style, comfort, and turnkey convenience in one of Madison's most sought-after condominium communities. This meticulously maintained 2-bedroom, 2.5-bath home has been thoughtfully updated throughout, allowing you to move right in and enjoy worry-free living. The sun-filled interior showcases fresh paint, all-new Harvey replacement windows, updated lighting, new window treatments, and a beautifully remodeled primary bath. The refreshed kitchen features brand-new stainless steel appliances, while the inviting living area is highlighted by a fireplace with elegant new glass doors. Additional upgrades include a new washer and dryer, delivering everyday convenience and modern functionality. Significant mechanical improvements provide added peace of mind, including a new furnace, central air condenser, and hot water heater. Nearly every major system has been updated, making this home truly move-in ready.

23 Esterly Farms Rd Unit 23, Madison

$455,000
2 Beds 2 Baths 24164028 MLS Kensington Acres South BLDG.
Privacy & convenience are both found within this updated detached stand-alone Ranch home in sought after Kensington Acres. Enjoy this 'tucked away' home yet a short walk to historic downtown Madison with its famed bookstore, shopping, restaurants & retail stores. This home has been beautifully maintained and shows pride of ownership throughout. Enjoy single floor living in your 2 bedroom, 2 bath home which features granite countertops in kitchen & baths, hardwood floors, light & bright open floor plan, natural gas fireplace and a year-round heated sunporch which is surrounded by nature and very well will be your most favorite room! Detached single car garage plus additional resident & guest parking. Newer Samsung gas stove & Bosch dishwasher. Updated HVAC - Trane AC unit manufactures date 1/2021 & Trane furnace date 4/2021.

6 Ladshaw Dr Unit 6, Madison

$450,000
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

$349,900
2 Beds 1 Baths 24197097 MLS
Nestled in picturesque Madison, Connecticut, this cottage is your private sanctuary, tucked away from the city's hustle and bustle. Enjoy serene surroundings, lush trees, and the beauty of nature. Blissful Outdoor Living: Step outside to savor the fresh country air in your spacious yard. Perfect for gardening, outdoor dining, or lounging in the sun. The loft is a versatile space - use it as a bedroom, home office, art studio, or peaceful reading nook. This cottage offers comfortable living without unnecessary fuss. This home has its own drilled well and septic system, which was installed in 2008, the heating system is nearly new as well. Madison combines countryside tranquility with seaside charm, including several public beaches and a private beach club. A short drive from New York City, it's an ideal escape for city dwellers. Explore local boutiques, dine at exquisite restaurants, or unwind by strolling along the picturesque coastline. Don't miss this opportunity to make this sweet cottage your own country escape, whether for weekends or permanent residence. Embrace the charm, privacy, and simplicity of country living while staying close to New York City. Schedule a viewing today and experience the magic of this Madison cottage. Your country escape awaits - seize the moment and start living the life you've dreamed of!

66 Wildcat Rd, Madison

$335,000
2 Beds 1 Baths 24195214 MLS
Highly sought after and rarely available-until now! 89-2 Cottage Road is the seasonal Madison cottage you'll want to run toward. Proudly part of the historic Little Colony community settled by veterans just after World War II, this lovely abode offers two bedrooms and a thoughtfully renovated full bath. The heart of the home is a generous, open-concept living space featuring a beautifully updated kitchen with granite countertops and a center island with a waterfall edge. Outfitted with newer appliances, new flooring throughout, and professional landscaping outside, each upgrade was carefully chosen to cultivate a beautiful yet serene space-easy to maintain, even easier to enjoy! Plus, the fully screened-in porch means there is plenty of space for gathering family and friends at the shoreline. Unlike many original cottages in the area, 89-2 was constructed with the integrity of a small home, featuring a full basement and crawl space for storage, insulation, and an oil heating system. Its larger size allows for conveniences uncommon in seasonal living, including a dishwasher and an in-home washer and dryer. Located within a short distance to Hammonasset, Madison town beaches, and town center, this is more than just a home-it is a gateway to a vibrant shoreline lifestyle. Seize this rare opportunity to own a piece of Madison history in a highly sought after community and come see for yourself why 89-2 Cottage Road is the ideal haven for making lifelong summer memories

89-2 Cottage Rd, Madison

$149,900
2 Beds 1 Baths 24170543 MLS
With a new roof in process, 32 North Street is calling you home! Set on one of the largest lots in Dud's Village, this lovely cottage is the idyllic seasonal abode. Equipped with 2 bedrooms, 1 full bath, and an outdoor shower, you will surely enjoy your summers along the Madison shoreline here. The recently refreshed kitchen and fresh coat of paint throughout will undoubtedly delight. And let's not forget the new floors in the kitchen and living room. The enclosed front porch is simply charming offering additional living space and featuring daybeds for cool summer sleepovers. Outside is an entertainer's paradise - a desirable corner lot with the oversized deck and enough yard space to host all your family and friends. Just a short distance to Salt Meadow Park, Hammonasset Beach State Park and downtown Madison, you'll always have something to do! And with summer right around the corner, you'll want to move quickly! Schedule your tour today and fully embrace coastal living at its finest! The village is seasonal - April 1st through October 31st. Land is leased by cottage owners, and the land lease is currently $5,400 per year. New roof to be completed as quickly as possible.

32 North St, Madison

$142,900
2 Beds 1 Baths 24168727 MLS
Nestled in the heart of picturesque Madison, this charming 2-bedroom, 1-bathroom seasonal cottage offers a serene sanctuary for enjoying summers along the shoreline. With a cozy living space, this quaint abode is perfectly designed for those seeking a peaceful beachside getaway. As you step inside, you're greeted by a warm and inviting atmosphere that captures the essence of coastal living. The open-plan living area maximizes the cottage's compact footprint, providing a comfortable space for relaxation and intimate gatherings. The kitchen is well-equipped for preparing light bites and beach picnics, while the two snug bedrooms offer a restful night's sleep after a day of fun in the sun. The loft space above the bedrooms awaits your imagination and offers an abundance of possibilities - pre-wired and ready to be finished to your heart's content! The cottage's prime location means you're just a short walk from the expansive sandy shores of Hammonasset Beach State Park. Madison's vibrant community is also at your doorstep, with its quaint downtown area, boutique shops, excellent restaurants, and attractions like the Madison Art Cinema and the historic E.C. Scranton Library. Whether you're looking for outdoor adventure or small-town charm, this cottage is the perfect seasonal home. Embrace the simplicity of cottage living and the beauty of coastal Connecticut with this delightful property, where endless summer memories await. Land lease - currently $5,400 per year.

92 Fourth Ave, 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.