Refine Search
Sort by
150 Race Hill Rd, Madison
$799,999
4 Beds ⋅ 3 Baths ⋅ 24208079 MLS
A rare and remarkably charming Antique in one of Madison's most picturesque settings. Set on 7+ acres along quiet Race Hill Rd, this beautifully preserved circa-1764 Cape blends centuries of character with thoughtful updates and the ease of modern living. Originally restored to the studs in 1996, the 2,091 sq.ft. main house retains an extraordinary amount of its original character, including chestnut flooring, period hardware, exposed beams and other details that give the home a wonderful sense of history. The floor plan is warm and inviting. The dining area opens to a family room with rustic beams, one of the original fireplaces and windows overlooking the private grounds. The family room, which could also work as a 1st floor bedroom, is highlighted by a 2nd original fireplace, built-ins and a full bath. The formal living room is distinguished with a 3rd fireplace, loads of windows and original cabinetry. A charming kitchen with cathedral ceilings and exposed beams, and a terrific sun room with a stone floor and private entrance complete the main living spaces. Upstairs you'll find three bedrooms and a full bath. And then there is the guest cottage! A beautifully renovated, year-round 701 sq.ft. legal one-bedroom cottage, that is an exceptional addition to the property-ideal for guests, extended family, a private office or rental use. Thoughtfully refinished and entirely independent, the cottage adds a level of flexibility rarely found.

150 Race Hill Rd, Madison

42 Concord Dr, Madison
$799,900
4 Beds ⋅ 3 Baths ⋅ 24206829 MLS
Perched on a scenic knoll in a highly desirable neighborhood, this classic colonial exudes curb appeal. A newly laid, meandering brick walkway leads to two inviting front entrances. Inside, the welcoming foyer opens to a sun-drenched living room that flows seamlessly into a beautifully renovated kitchen. A chef's dream, the kitchen boasts crisp white cabinetry, a contrasting grey-washed center island with waterfall "Carrara-style" quartz countertops, and a spacious dining area perfect for hosting large gatherings. French doors open to a serene four-season porch and a sizable deck, making indoor-outdoor entertaining effortless. The main level also features a generous family room with a cozy gas fireplace. With its own private entrance, this versatile space is ideal for an in-law suite, au-pair quarters, or a quiet home office. Upstairs, the primary suite is a true sanctuary, complete with a walk-in closet and a tastefully renovated, spa-like bath featuring heated floors. Three additional spacious bedrooms, all customized with California Closets, share a second beautifully updated full bath. Freshly painted throughout, the home also features a finished lower level with brand-new composite flooring and a highly functional mudroom just off the garage. This is a lovely home in a sought after private neighborhood and the community of Heatherwood is special within itself- come and experience all that it has to offer.

42 Concord Dr, Madison

7 Highland Ter, Madison
$799,000
3 Beds ⋅ 1 Baths ⋅ 24213904 MLS
This "Diamond in the Rough" is ready for its next owners to create lasting memories. Located just a short walk to a private association beach in one of Madison's most desirable shoreline neighborhoods, this home offers an incredible opportunity to make it shine. While it does need TLC, the investment is well worth it , as proven by the beautifully-transformed nearby homes. Bungalow in style, the home has the original beadboard wainscoting on the walls and ceilings, reminiscent of the 1920's, and consists 5 rooms including 3 bedrooms and a LR/DR combination with a wood stove that is currently in the LR fireplace. One might imagine that the enclosed front porch had been used as a sleeping porch during the summer months. There is central air conditioning and a whole-house generator plus a 2-car detached garage. Enjoy all Madison has to offer, which includes excellent restaurants, a private award-winning bookstore and cafe in the center of town, a wonderful library and several delightful shops in which to indulge one's self. The Green in the center of town hosts many cultural events, including the popular July 4th concert featuring a symphony orchestra's performance of well-known patriotic music.

7 Highland Ter, Madison

3 Little Hollow Rd, Madison
$795,000
4 Beds ⋅ 3 Baths ⋅ 24205125 MLS
Welcome home to this classic four-bedroom Colonial offering timeless charm, modern updates, and an ideal layout for everyday living, complete with gorgeous wide plank flooring throughout. Freshly updated, the home features stylish new light fixtures and major mechanical upgrades, including a new roof (2022) and a new Carrier HVAC system for the second floor (2026). At the heart of the main level is an eat-in kitchen with cabinets painted in 2022, a new dishwasher (2024), and a spacious dining area set in front of a cozy fireplace. Sunlight pours into the breathtaking family room featuring soaring vaulted ceilings and a warm gas fireplace. Glass French doors open from the welcoming foyer into the living room, which boasts its own fireplace and connects seamlessly to the formal dining room. A dedicated mudroom off the kitchen includes a new washer and dryer (2024), alongside a convenient first-floor half bath. Upstairs, the primary suite serves as a peaceful retreat with vaulted ceilings, an expansive walk-in closet, and a private full bath. Three additional generous bedrooms share a renovated full bath with double sinks. Step outside to an impressive deck overlooking a lush yard-perfect for outdoor dining, playing, or relaxing. Ideally located just minutes from top-rated schools, vibrant town amenities, and picturesque local beaches, this move-in-ready property offers the ultimate combination of space, style, and peace of mind.

3 Little Hollow Rd, Madison

2125 Durham Rd, Madison
$749,900
4 Beds ⋅ 4 Baths ⋅ 24195345 MLS
Tucked away on a sweet cul-de-sac at the end of a private road, well off of Route 79, this spacious 4-bedroom Colonial welcomes you with a wonderful sense of privacy and tranquility. Enjoy plenty of room to gather, relax, and make yourself at home, including a full finished walk out basement with endless possibilities. This low maintenance home features a new roof, hardwood floors throughout, a new kitchen island & new granite countertops. The inviting first floor features a bright family room with a wood burning fireplace and French doors to a freshly painted deck. There are only a few steps to the 2-car attached garage. It also features a comfortable living room and dining room. The second floor has 4 large bedrooms with newly installed hardwood floors. The primary bedroom with vaulted ceilings and skylight has an en-suite bathroom with soaking tub & walk in shower. There is a walk-up attic off of the second bedroom, currently being used as an office. Laundry is on the second floor opposite the family bathroom. Two more large bedrooms complete the second floor. The walk-out basement is partially finished with a game room, office area, bedroom and full bathroom. Ideally located near hiking & biking trails for the nature enthusiast. Enjoy all that the charming town of Madison has to offer; award winning high school, 3 beautiful town beaches, plus Hammonasset State Park, shops, restaurants, state of the art library plus a wonderful community.

2125 Durham Rd, Madison

58-A Kelsey Pl, Madison
$725,000
24211007 MLS
Build your dream home here, only steps away from your private neighborhood beach on Long Island Sound, in Madison's Neck Road community. Conveniently located near shopping in Madison or Guilford, highways, and public transportation, this special parcel is close to everything. Here's a rare opportunity to build on a level 80' x 150' (12,000 sq. ft.) lot that is CONFORMING in its R-5 Zone, allowing one to build up to 3,400 s. ft. of living area, on up to 1840 sq. ft. of coverage. Yard requirements result in a 43' x 113' setback-compliant area on which to place your design. (See sections 4.5 through 4.9 of Madison Zoning Regulations) This now-conforming lot was created by merging two previously non-conforming lots; 58A, which was a "double lot", and 58B, effectively creating a conforming triple lot (relative to the original 1950's subdivision). This level lot is outside of the Special Flood Hazard Areas, and so should not require flood insurance or other special FEMA restrictions. Ownership requires membership in the neighborhood association (KPBA), including all the homes on Kelsey Place and Blakeman Road, which maintains the roads, etc. ($232.08 association tax for 2026, based on assessment) And, purchase will convey membership in a smaller association of 17 homes (KPRA) that together own 82.5 feet of beach on Long Island Sound. ($425 dues for 2026)

58-A Kelsey Pl, 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.

How much is your home worth?

Get instant property value now!