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$599,900
24168048 MLS
Fully approved and ready to go, this exceptional commercial lot is situated in the heart of vibrant downtown Madison. Boasting approvals for a 5,000 square foot building the property includes a brand-new septic system, 13 designated parking spaces with additional parking options, and unbeatable proximity to restaurants, shopping, the train station, and I-95. Imagine welcoming clients or customers just a short stroll from Madison's beautiful beaches in this high-visibility location. Whether you're looking to create a professional office, boutique retail space, or explore endless other possibilities, this is a rare chance to establish your business in one of the shoreline's most desirable communities. The potential here is truly unlimited!

885 Boston Post Rd, 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
$579,900
3 Beds ⋅ 1 Baths ⋅ 24203485 MLS
Escape to the Connecticut shoreline with this beautifully styled Cape, ideally situated in desirable Madison. Offering 3 bedrooms and 1 full bath, this charming home features inviting indoor and outdoor living spaces designed for comfortable everyday living and relaxed coastal living. Set on a private, lightly wooded corner lot, the property offers a peaceful sense of privacy while remaining close to everything Madison has to offer. Recent improvements include new cedar siding, windows throughout with custom window treatments, propane fireplace installation, and professional interior painting, all completed in 2025. The roof and septic system were both replaced in 2022. Just a 5-minute drive to vibrant downtown Madison, enjoy easy access to charming boutiques, restaurants, and cafes, as well as Hammonasset Beach State Park, with miles of sandy shoreline and scenic coastal walks. Convenient access to I-95 puts downtown New Haven approximately 25 minutes away. Turnkey and thoughtfully updated, this inviting Cape offers the perfect blend of classic New England charm, modern improvements, and an exceptional shoreline location. A wonderful opportunity to enjoy the best of Madison living in a peaceful coastal setting.

6 Bower Rd, Madison
$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
$559,000
3 Beds ⋅ 3 Baths ⋅ 24198297 MLS
Nicely maintained 3-bedroom, 3-full-bath home nestled in a quaint cul-de-sac setting. The home is in very good condition and offers comfortable living space both inside and out. The spacious kitchen features granite countertops, plenty of cabinet space, and a center island-perfect for everyday living and entertaining. Primary Bedroom has its own private full bath. Living Room-Dining combination offers a slider to a deck overlooking the peaceful backyard and small pond, creating a relaxing setting to enjoy the outdoors. Lower level offers a large family room with a walk-out to a patio, providing additional living and entertaining space. With its peaceful setting, versatile living spaces, and inviting outdoor areas, this home is ready to welcome its next owners.

25 Samantha Ln, Madison
$550,000
24170118 MLS
Overview Turnkey opportunity to acquire a well-established restaurant business in the desirable shoreline town of Madison, Connecticut. The James Madison House Restaurant benefits from strong local recognition, consistent year-round traffic, and proximity to the town center and coastal attractions. This is an ideal opportunity for an owner-operator or experienced restaurateur to step into an existing operation with immediate income potential and upside. Key Highlights Established restaurant with loyal customer base Prime shoreline location in high-income demographic Turnkey operation with existing kitchen and infrastructure Consistent year-round business with seasonal upside Located within an active commercial setting Opportunity to rebrand or enhance concept Facility Fully built-out restaurant space Equipped commercial kitchen Dining area with established layout Lease in place Growth & Expansion Opportunities Extend operating hours / add service days Introduce new menu concepts or bar program Increase marketing and digital presence Expand catering / private events

508 Old Toll Rd, Madison
$500,000
3 Beds ⋅ 3 Baths ⋅ 24204341 MLS
A Fantastic Opportunity in an Adorable Neighborhood Welcome to a home that offers incredible potential, a great location, and peace of mind with many of the major systems already updated. While this property needs work and updating, the big-ticket items have been taken care of, making this an exciting opportunity for someone looking to build equity and create a home that truly reflects their style. Recent improvements include a 2024 roof, 2024 central air conditioning, 2024 furnace, 2025 oil tank, 2025 garage doors, a 2023 hot water heater, and a brand-new septic system installed in 2026. With so many important mechanical and structural components recently addressed, you can focus your energy on transforming the interior and making the home your own. Nestled in an adorable, established neighborhood surrounded by homes that are significantly more expensive, this property presents a rare opportunity . Whether you're looking for a renovation project or an investment opportunity, the possibilities are here. Bring your vision, your ideas, and your contractor - this one is ready for its next chapter! A few offers have been submitted, please submit highest and best by Friday at 5pm

18 Saint Francis Woods Rd, Madison
$500,000
2 Beds ⋅ 2 Baths ⋅ 24203562 MLS ⋅ Kensington Acres North BLDG.
Charming two-bedroom ranch in the desirable North Kensington community. Enjoy central air conditioning, gas heat, and a beautiful screened-in porch overlooking the pond-an inviting space to relax and unwind. The home features generously sized bedrooms and two full bathrooms, offering comfort and convenience for guests and everyday living. Cozy up by the gas fireplace, which is easy to turn on and off. A detached one-car garage provides additional storage and parking.

14 Hampshire Road Unit 14, 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

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