Madison Homes under $750,000

Madison Homes under $750,000

Welcome to Madison, Connecticut – a picturesque coastal town that perfectly blends small-town charm with modern conveniences. Nestled along the scenic shores of Long Island Sound in New Haven County, Madison is renowned for its stunning beaches, vibrant downtown, and rich historical heritage. With a population of just over 18,000 residents, this community offers a warm and welcoming atmosphere, making it an ideal place to call home.

Madison boasts a variety of recreational opportunities, from exploring the beautiful Hammonasset Beach State Park to enjoying the quaint shops and delightful eateries in the town center. Nature enthusiasts will appreciate the numerous parks and trails that dot the area, offering a perfect backdrop for outdoor activities year-round.

For those seeking a new home in Madison, you'll be pleased to know that there are fantastic options available under $750,000. Whether you’re looking for a charming colonial, a cozy cottage, or a modern townhouse, the real estate market here offers a diverse selection that caters to various tastes and lifestyles. Many homes feature spacious layouts, updated amenities, and beautifully landscaped yards, all within close proximity to local schools and the stunning shoreline.

Living in Madison means embracing a community that values education, arts, and family-friendly events, all while enjoying the serene beauty of Connecticut’s coastline. With its exceptional quality of life and a variety of affordable housing options, Madison is not just a place to live – it’s a place to thrive. Discover your dream home in this enchanting town today!

Newest Madison Homes under $750,000

67 Nortontown Rd, Madison
$695,000
4 Beds ⋅ 2 Baths ⋅ 24215254 MLS
Take a 3D Tour OR Enjoy a Video Walkthrough 24/7! Move right into this charming 4 BR, 2 Bath Madison farmhouse offering 1,956 SF of living space on a nearly 1-acre, level lot backing to protected land trust open space! Built in 1940 with a spacious 1980 addition, this home combines classic character with thoughtful updates, including the convenience of a first-floor primary BR. Three additional BRs upstairs provide flexibility for guests, hobbies or work-from-home needs. Beautiful hardwood floors, a welcoming Living Room with stone fireplace & sunny bay window, a bright, spacious Kitchen with breakfast bar, formal Dining Room, home Office & an expansive Rec Room with direct access to the rear deck provide plenty of room to spread out. The major improvements are already complete: NEW roof (2024), furnace & central A/C (2023), water heater (2022), septic tank (2011), replacement windows (2008) & upgraded 200-amp electrical service. Low-maintenance aluminum siding adds to the appeal. Relax on the inviting 3-season enclosed front porch with windows or entertain on the expansive rear deck overlooking the level backyard & protected land trust open space. A detached 2-car garage offers convenient loft storage. Enjoy quick access to I-95, Madison's charming village center, shoreline & Hammonasset Beach State Park. At $695,000, this move-in-ready home offers space, flexibility & significant recent improvements. Schedule your private showing today!

67 Nortontown Rd, Madison
41 Bradley Corners Rd, Madison
$569,900
4 Beds ⋅ 3 Baths ⋅ 24211348 MLS
Beautifully updated and wonderfully maintained, this exceptional 4-bedroom Colonial offers a great & comfortable lifestyle in a highly desirable Madison location. From the moment you enter, you'll appreciate the natural light, handsome hardwood floors, and thoughtful improvements throughout. At the heart of the home is a gorgeous, sun-filled kitchen featuring a big bay window, center island, granite countertops, gas range, stainless appliances, and pantry. Just beyond the kitchen, the inviting family room makes a wonderful gathering space with its soaring cathedral ceiling, wood stove, and glass French doors opening to a fabulous multi-level deck. The spacious living room is filled with natural light, while the dining room is perfectly suited for entertaining. Upstairs, the private primary suite features a remodeled full bath, accompanied by three additional bedrooms and a second beautifully updated full bath. The extensive list of improvements includes replacement windows, brand-new roof, new oil tank, new well pump and water softener, and a whole-house generator.Outside, the attractive, easy-care yard provides plenty of room to relax and entertain, while the two-car garage and central air adds everyday convenience. A wonderful opportunity to enjoy the best of Madison living in a home where style, comfort, and quality updates come together beautifully. OFFERS HAVE BEEN RECEIVED. HIGHEST & BEST WITH NO ESCALATIONS TO BE IN BY 10AM MONDAY OCTOBER 19th

41 Bradley Corners Rd, Madison
16 Tamarac Dr, Madison
$599,000
3 Beds ⋅ 2 Baths ⋅ 24214239 MLS
Welcome to this beautifully maintained home on a cul-de-sac street. Low traffic, great for play. When entering this inviting home, the foyer greets you with the natural light of the main living room's oversized windows creating a bright ambience that flows seamlessly into the eat-in kitchen and dining area. The updated kitchen features newer stainless steel appliances (2024), while beautiful hardwood floors add warmth and character throughout the main level. Just a few steps up, you'll find three generously sized bedrooms,including a spacious primary bedroom, all featuring beautiful hardwood floors that continue into the hallway. Entire interior painted, along with new interior doors (2024). The versatile lower level offers additional living space, complete with a cozy raised hearth fireplace w/newer wood-burning/pellet stove (2023), newly renovated full bathroom and laundry area(2020). Whether you envision a comfortable family room, home office,or creative retreat,this space offers endless possibilities. Step outside onto the expansive deck overlooking a lush,lovingly landscaped property and spacious, level yard.This private outdoor oasis is perfect for summer entertaining,relaxing evenings, or simply enjoying the peaceful surroundings. Complete with a two-car garage and ideally situated just minutes from schools (Neck River, Polson,Hand) the shoreline, shopping, restaurants, and interstates, this home offers the perfect combination of style, functionality, and convenience.

16 Tamarac Dr, Madison
14 Bower Rd, Madison
$599,900
4 Beds ⋅ 2 Baths ⋅ 24212728 MLS
Nestled on a picturesque stretch of Madison's desirable shoreline community, this exceptional property offers the perfect blend of New England charm, privacy, and convenience. Set on a beautifully maintained lot, 14 Bower Road provides an inviting setting for year-round living or a relaxing coastal retreat. Thoughtfully designed living spaces are filled with natural light, creating a warm and welcoming atmosphere throughout. The home features spacious gathering areas, a well-appointed kitchen, comfortable bedrooms, and seamless indoor-outdoor living ideal for entertaining family and friends. Outdoor spaces offer room to relax, garden, or simply enjoy the tranquility of the surrounding landscape. Ideally located just minutes from Madison's vibrant town center, beaches, boutiques, restaurants, and commuter routes, this property combines a peaceful residential setting with easy access to everything the Connecticut shoreline has to offer. A two-car attached garage and full walk-out basement provide excellent storage, workshop space, or future finishing potential. The private backyard offers plenty of room for entertaining.

14 Bower Rd, Madison
270 Scotland Rd, Madison
$469,000
3 Beds ⋅ 2 Baths ⋅ 24210705 MLS
Tucked away on a private setting high above Scotland Road, 270 Scotland Road offers the perfect combination of privacy, space, and natural beauty. Set on approximately 2 acres of lightly wooded land, this 3-bedroom, 1.5-bath raised ranch enjoys elevated surroundings with seasonal views toward the Hammonasset River. The main level features a comfortable, flowing layout with hardwood floors throughout the spacious living room, complete with a fireplace that creates a warm and inviting focal point. The updated kitchen offers stainless steel appliances, tiled flooring, and a generous dining area with plenty of space for everyday living and entertaining. Three bedrooms and a full and half bath are conveniently located on the main level. Downstairs, you'll find additional finished living space with a beautiful brick fireplace, offering flexibility for a family room, home office, recreation area, or guest space. Set back in a private, lightly wooded setting, this home offers the opportunity to enjoy the peace and privacy of acreage while remaining conveniently located in Madison. With its elevated setting, river views, spacious lot, and flexible living space, 270 Scotland Road is a property worth seeing in person.

270 Scotland Rd, Madison
273 Horse Pond Rd, Madison
$600,000
5 Beds ⋅ 2 Baths ⋅ 24210111 MLS
**Offered for the first time in over 54 years, this oversized ranch provides exceptional space, flexibility, and charm. Originally built in 1972 by a longtime Madison resident for his two daughters, this 2,240squarefoot home has been thoughtfully designed to accommodate a variety of living arrangements. Located in Madison's desirable southern section on a generous 1.33acre lot, the property offers convenient access to the downtown village, sandy town beaches, Hammonasset State Park's walking trails, and Madison's Town Campus. It's a rare opportunity to enjoy privacy while remaining close to everything Madison has to offer. This unique residence was constructed as a true duplex ranch, featuring two full kitchens, two living rooms, and two full baths-all connected and all on one level. A welcoming front foyer provides two separate entrances, complemented by two additional rear entrances. With three bedrooms on one side and two bedrooms on the other, the layout is ideal for an inlaw suite, multigenerational living, or simply enjoying the benefit of five total bedrooms and abundant square footage. Craftsmanship from a bygone era is evident throughout, with many rooms showcasing the original parquet hardwood floors. Both kitchens open directly to the expansive and private rear yard, offering wonderful outdoor enjoyment and potential for future expansion if desired. Don't miss this rare chance to own two homes in one-a truly special offering in Madison.

273 Horse Pond Rd, Madison
371 Race Hill Rd, Madison
$375,000
3 Beds ⋅ 2 Baths ⋅ 24209422 MLS
Welcome to 371 Race Hill Road, a 3-bedroom, 2-bath home offering 1,236 square feet of comfortable living on a private 1.12-acre lot in desirable Madison. The well-laid-out floor plan makes everyday living easy, while the generous yard gives you room to garden, play, and entertain. Recent updates include a new electric water heater (2025), and the home is heated by an oil-fired furnace with a 330-gallon tank. Conveniently located near Madison's shoreline, town center, shopping, and dining, with easy access to I-95. Furnishings are available for purchase, offering the incoming buyer a turnkey option.

371 Race Hill Rd, Madison
343 Horse Pond Rd, Madison
$675,000
3 Beds ⋅ 3 Baths ⋅ 24207706 MLS
This sun-drenched and beautifully updated Cape offers a rare blend of charm, versatility, and an exceptional shoreline location. With two distinct living spaces, the property presents an outstanding opportunity for multigenerational living or a compelling investment property. The main residence features a stylishly renovated kitchen opening to a spacious dining area, two bedrooms-including an impressively spacious primary bedroom-two full baths, and a fabulous rear deck perfect for outdoor dining and entertaining. The attached in-law suite offers privacy and independence with its own updated kitchenette, full bath, washer and dryer, and beautiful open loft-style bedroom-ideal for extended family, guests, a private home office, or potential rental income. Outside, enjoy a large detached garage, hot tub, and storage shed. Located across from Cole's Farm, with a fishing pond just a short walk away and Hammonasset Beach State Park within an easy bike ride. Convenient to scenic trails, downtown, shopping, and dining, this unique property offers extraordinary flexibility and coastal living at its best!

343 Horse Pond Rd, Madison
39 Mill Rd, Madison
$625,000
5 Beds ⋅ 2 Baths ⋅ 24206863 MLS
The Perfect Location on picturesque 3/4 of an Acre. Walk to Hammonasset State Park and enjoy the Trails and 2-Miles of Pristine Sandy Beach ~ This Antique Saltbox boasts a total of 2,262 square feet of heated living space. Windows have been upgraded with Pella Double Pane Insulated Windows throughout. Included in the floor plan is a legal 1-Bedroom Apartment on the first floor. You'll need to Roll up your sleeves and do some work, but the results should pay dividends.

39 Mill Rd, Madison
1 Hampshire Rd Unit 1, Madison
$695,000
2 Beds ⋅ 2 Baths ⋅ 24205396 MLS ⋅ Kensington Acres North BLDG.
Downsize Without Giving Up the Space You Need! Looking to downsize but still need generous storage, a workshop, and dedicated space to work from home? The largest condo in desirable Kensington Acres North offers an exceptional combination of comfort, flexibility, and space. This stand-alone unit features a spacious primary suite plus a guest bedroom. The open living and dining areas flow seamlessly to a screened porch, perfect for relaxing or entertaining while looking into your private, spacious backyard. The kitchen features bar seating with new counter tops by Gedney. Beautiful,new laminate floors run throughout the home. For those working from home or pursuing creative projects, the property offers a truly unique advantage: walk through the main house to an office and studio with a large seating area, half bath, and separate entrance-ideal for a home office. Storage and workshop space are equally impressive. A walk-up attic provides abundant storage, while the nearly 1900-square-foot basement offers tremendous potential and could be easily finished to create the workshop, recreation space, or additional living area you've been looking for. And the location is hard to beat. Hummer Pond is on the property plus enjoy easy access to Hammonasset State Park, East Wharf Beach, and downtown Madison, all just a short walk away. Downsize your home, not your lifestyle. Come see all this exceptional condo has to offer.

1 Hampshire Rd Unit 1, Madison
23 Esterly Farms Rd Unit 23, 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
38 Church Ln, Madison
$699,000
4 Beds ⋅ 2 Baths ⋅ 24198873 MLS
Welcome to 38 Church Lane, where exceptional custom renovations meet a captivating Madison setting. Perched high on a large corner lot surrounded by mature trees, this thoughtfully updated 4-bedroom, 2.5 bath home offers sophisticated finishes, a flexible floor plan ideal for multi-generational living and privacy just minutes from Madison's town center and shoreline. The stunning kitchen, custom-crafted by Gedney Kitchens, features bespoke cabinetry and premium finishes, while an oversized fireplace anchors the inviting living room. The finished lower level includes a comfortable den with Vermont Castings wood-burning stove, custom Gedney wet bar, light-filled bedroom/office, and spa-inspired renovated bath with dual-head shower, heated floors, and heated towel rack. Outside, a brand-new composite deck overlooks terraced grounds with mature trees, stonework, curved pathways, and inviting spaces to garden, gather, and explore. An existing front-yard pond scape offers intriguing possibilities for future re-imagining. Hardie board siding with AZEK trim provides a remarkably low-maintenance exterior, complemented by energy-efficient windows and central air. Minutes from Madison's shops, dining, and beautiful shoreline beaches, this one-of-a-kind property truly must be experienced in person.

38 Church Ln, Madison
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