Refine Search
Map
Sort by
$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
$499,900
3 Beds ⋅ 2 Baths ⋅ 24199405 MLS
First Time Offered In 25 Years. This contemporary raised ranch, set on 2.36 secluded acres, is located in a quiet cul-de-sac neighborhood just minutes to town. The living room with hardwood floors features a cathedral ceiling with beams, a wood burning fireplace, floor to ceiling windows with double sliders to a deck with built in bench, perfect for morning coffee or evening enjoyment. The adjacent dining room also has sliders to a patio. The kitchen with breakfast bar is waiting for your personal touches. Down the hall you will find 2 spacious guest bedrooms with large closets that share a hall bath. The primary bedroom with walk-in closet has its own full bath. Downstairs is a large family room with a wood stove to keep things cozy and sliders to an additional patio. The laundry is also located on this level. Though located in a private wooded setting, this home is conveniently located to town, beaches, parks and all that Madison has to offer.

35 Aileen Dr, 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
$449,000
1 Beds ⋅ 2 Baths ⋅ 24198868 MLS ⋅ West Sussex Place BLDG.
End-unit townhouse condominium in Madison, Connecticut - open-concept living,attached garage, plus a finished lower level! Built in 2006 at West Sussex Place, this move-in ready home features hardwood floors, a kitchen with granite countertops and stainless steel appliances, and a light-filled living and dining area on the main level. Primary bedroom, Loft (or 2nd bed) and the full bath are on the upper level, with a half bath on the main floor. The finished lower level adds approximately 608 square feet of flexible space for a home office, media room, fitness area, or recreation room, along with laundry and storage. Outside, a covered front porch and private rear patio extend the living space on a level, lightly wooded lot. Natural gas hot air heat, central air conditioning, natural gas hot water, and underground utilities, with vinyl siding for low exterior maintenance. An attached one-car garage plus assigned driveway parking. West Sussex Place is a 25-unit community minutes from downtown Madison, Boston Post Road shops and restaurants, Madison Art Cinemas, Hammonasset Beach State Park, and the beaches of Long Island Sound, with quick I-95 access. Please note that I-95 traffic is audible outdoors. Living in Madison provides access to the Surf Club, beach front area with sporting events, stretch of sand and surf, along with seasonal restaurant. The Madison shoreline is beautiful, you truly need to live it!

5 W Sussex Pl Unit 5, 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.