Madison, CT Homes for Sale with Garage

Coming Soon! Goes Live 7-27-26. Professional Photos coming. Tucked away in the sought-after Esterly Farms community, this 1,372-square-foot townhouse offers a seamless blend of comfort & shoreline charm. The thoughtfully designed layout is anchored by stunning Brazilian cherry wood floors that flow throughout the main level, adding a rich, polished warmth to the home. The inviting living area

Lisa Rollins Team Compass Connecticut, LLC

Built by a highly regarded shoreline builder known for uncompromising attention to detail, this residence is designed for buyers who appreciate elevated finishes, enduring quality, and effortless livability. The home features an open floor plan with white oak hardwood floors, 9-foot ceilings, custom millwork, and oversized Pella windows throughout. A stunning bluestone entry leads to an elegant

Steve Wollman Wollman Realty

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

Laura Cariati William Raveis Real Estate

Less than one mile from downtown Madison, this new construction home offers refined living with white oak floors, custom millwork, coffered ceilings, and abundant natural light throughout. The main level features 9-foot ceilings, a dramatic floor-to-ceiling gas stone fireplace with built-ins, a chef's kitchen with Sub-Zero and Wolf appliances, double ovens, pot filler, wet bar with wine chiller,

Steve Wollman Wollman Realty

Step into a story nearly three centuries in the making. Tucked away on a total of 3 enchanting acres along Connecticut's picturesque shoreline, this extraordinary circa-1752 former Helen Foster Snow homestead is a place where history whispers through every room and timeless beauty meets modern living. Once home to the renowned journalist, author, and humanitarian, the property carries a

Allison Ciarcia William Raveis Real Estate

Built in 2001, this expansive Custom Cape with its charming front covered porch offers a one-of-a-kind setting in North Madison, ideally located at the end of a cul-de-sac on 2.64 acres and surrounded by open space. The square footage is deceptive with 3536 sf (this DOES NOT include the 3-season room +452 sf) plus the huge basement offering another 1880 sf. Designed with intention and exceptional

Claudia O'Connell William Raveis Real Estate

Set on 5.65 secluded acres in the heart of Madison, this exceptional English Georgian custom home offers a rare blend of timeless architecture, refined craftsmanship, and natural beauty. Surrounded by mature woodlands, the property is a private retreat, complete with a gently winding stream and the preserved stone remnants of a historic mill-an evocative nod to the land's rich past. Inside, the

Mark McElrath William Pitt Sotheby's Int'l

A rare investment opportunity with unmatched storage and garage space! Tucked away on a private 2-acre lot just minutes from I-95 and everything Madison has to offer, this unique property combines immediate rental income with an incredible opportunity for the next owner. The 3-bedroom home is currently tenant-occupied, generating $2,500 per month in rental income, while the expansive detached

Meig Walz Newcomb Coldwell Banker Realty

This exceptional ranch-style home is set on a beautifully landscaped lot just minutes from Madison's charming town center and sandy beaches. A semi-circular driveway, classic brick and clapboard exterior, stone walls, and mature plantings create a stunning first impression.Step into the sun-filled two-story foyer and discover elegant finishes throughout, including hardwood floors, crown molding,

Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

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

Greg robbins Houlihan Lawrence WD

Stunning waterfront home with water views on both sides, offering a rare coastal setting in an upscale neighborhood surrounded by multimillion-dollar properties. Enjoy breathtaking views from the rear of the home and expansive backyard, along with shared waterfront access across the street where a kayak or small boat may be launched at high tide. Designed with flexibility in mind, this home

Heather Smith Our Home Realty Advisors

Rare coastal compound opportunity in Madison's highly desirable Seaview Beach area. Situated on approximately one-half acre just moments from the shoreline, this unique property features a main residence and a newer detached accessory dwelling unit, offering flexibility rarely found in one of Connecticut's premier shoreline communities. The main home is clean, functional, and ready for a new

Karina Ukhnitska Real Broker CT, LLC

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

Lisa Edgerton William Raveis Real Estate

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

Kelly Whiteman William Raveis Real Estate

Privately positioned on nearly two acres in one of Madison's most desirable areas, this expansive Colonial offers a rare combination of privacy, scale, and convenience. Surrounded by natural beauty, the property feels secluded while remaining just minutes from the shoreline and Madison's charming town center, known for its dining, boutique shops, and coastal New England character. A true

Adriana Radu Coldwell Banker Realty

Welcome to easy, low-maintenance living in this beautifully maintained 2-bedroom 1.5 bath condo built in 2006. Offering 1,296 square feet of comfortable living space, plus approximately 608 additional finished square feet in the lower level (cement floor), this home provides plenty of room to relax, entertain, or work from home. The open floor plan features hardwood floors, a spacious kitchen

Kimberly Stasiak Century 21 AllPoints Realty

Updated 4 bedroom 2 Full bath Cape on 15+ Acres of rolling Meadows and woods bordering State Forest and over 800 feet of frontage on Opening Hill. Extensive updating includes new windows and doors, original wide-board refinishing in the original building. A new kitchen in the cathedral ceilinged family room addition with deck that commands beautiful views of two spring fed, stocked ponds below

Steve Adkins Berkshire Hathaway NE Prop.

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 with bright natural light, the home boasts peaceful, expansive lawn views from your private enclosed Sun Room, the perfect spot for morning coffee. A flat, level &

Todd Gould William Pitt Sotheby's Int'l

Set gracefully on a beautifully landscaped property framed by classic New England stone walls, this timeless Colonial has been thoughtfully refreshed and offers the perfect balance of warmth, charm, and modern comfort. A welcoming covered front porch opens an inviting interior with a classic, smart floor plan. At the heart of the home is the Kitchen featuring honed granite, GE Monogram stainless

Phoebe Schreiner William Pitt Sotheby's Int'l

Completely rebuilt and expanded in 2026, this custom coastal home with deeded beach rights is located in Madison's charming Seafields Association. Thoughtfully designed with designer details throughout, the home provides elevated shoreline living with glimpses of Long Island Sound, state-of-the-art appliances, high-end finishes, a bright, open layout, mudroom, butler's pantry with laundry, and a

Steven Koleno Beycome of Connecticut

Nicely updated 1476 sf condo with family room, plus 3 season sunporch and full basement. Largest style at Windermere. Living room and dining room are open and have nice hardwood floors. The home has all new windows! Newer kitchen with maple cabinetry. Cozy family room with fireplace opens to a 3 season porch. Off the sunporch is a private patio. There are 2 good sized bedrooms and 2 lovely newer

Judy Libby Berkshire Hathaway NE Prop.

Rare opportunity to own a Nantucket-style coastal retreat on coveted Middle Beach Road in Madison. Just moments from East Wharf Beach and downtown, this distinctive property offers timeless shoreline charm, a huge porch, breathtaking tidal marsh views, and glimpses of Long Island Sound from the second floor. Filled with character and reminiscent of a 1920s seaside cottage, the sun-filled main

Sheila Tinn-Murphy Berkshire Hathaway NE Prop.

Private.Pastoral.Purposeful. Available for the first time in decades. This rare 4-acre compound offers a Farmhouse style home, a guest house, 3-car garage with additional storage, and attached in-home gym, office equipped with bathroom, and artist's studio. This legacy property delivers both on location and acreage offering a one-of-a-kind sequestered compound that simply cannot be replicated.

Heather Clinton Berkshire Hathaway NE Prop.

Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight

Meig Walz Newcomb Coldwell Banker Realty

Set on a beautiful, private 1.25-acre lot in one of Madison's sought-after neighborhoods, this spacious, well maintained Colonial offers exceptional flexibility and comfort with nine rooms plus an additional sunroom. The kitchen is updated with granite countertops and newer appliances. Bathrooms have all been updated with tile and granite. The floors are hardwood throughout the home. Thoughtfully

Susan Wagner Berkshire Hathaway NE Prop.

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

Carol Mancini William Pitt Sotheby's Int'l

Situated on over an acre of manicured grounds, this custom-built Colonial blends traditional charm and modern convenience. An inviting front porch welcomes you into a thoughtfully designed floor plan. The main floor flows effortlessly from each room to the next. The eat-in kitchen features stainless steel appliances and sliders to a rear deck. A see-through wood-burning fireplace creates a focal

Kayla Chasse Compass Connecticut, LLC

Beautifully updated Cape Cod, ideally situated on two private acres near the Killingworth/Madison town line, offering the perfect blend of classic charm and modern updates. Recent improvements include vinyl siding, replacement windows and slider, a renovated kitchen, updated bathrooms, refinished hardwood floors, and a newly installed well neutralizing system. Recently painted throughout, the

Linda Toscano Coldwell Banker Realty