Homes with Pools for Sale in Madison, CT

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ABOUT THIS HOME
Home with a Pool for sale in Madison, CT:
A rare opportunity at one of Madison's most storied shoreline addresses. Set back from the water on a lush, professionally landscaped acre, this sophisticated four-level residence offers resort-like living with deeded private beach rights directly across the street, a distinctive touch on the Connecticut shoreline. Nearly 6,000 square feet of impeccably designed living space unfolds across six bedrooms, five full baths, and two half baths. French doors invite the summer air into an oversized eat-in kitchen, expansive family room, home office, and formal living and dining rooms, all conceived by a celebrated design eye. A show-stopping third-floor retreat with two bedrooms, a hangout area, a

$4,499,000

6 beds6.5 baths5,817 sq ft

14 Middle Beach Rd W, Madison, CT 06443

Bonus room • Detached garage • 0.92 acre lot

ABOUT THIS HOME
Home with a Pool for sale in Madison, CT:
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

$574,000

2 beds2.5 baths1,976 sq ft

250 Legend Hill Rd #250, Madison, CT 06443

Formal dining room • Entry foyer • Living room

ABOUT THIS HOME
Home with a Pool for sale in Madison, CT:
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 replaced were central-air, furnace and all new stainless steel appliances. This unit is over 1800 square feet, not inclusive of the finished sunroom off of kitchen and the 2 finished rooms in the walk out basement. There is plenty of storage in the attached 2 car garage, with another unfinish

$635,000

2 beds2.5 baths2,604 sq ft

81 Legend Hill Rd #81, Madison, CT 06443

New flooring • New carpets • $885 HOA

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Madison, CT:
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 lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equ

$3,495,000

5 beds5 baths5,657 sq ft

45 Island Ave, Madison, CT 06443

1.57 acre lot • 3 garage spots • Pool

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ABOUT THIS HOME
Home with a Pool for sale in Madison, CT:
Nestled on 4.5 private acres, this spacious 2,208-square-foot home offers the perfect blend of comfort, recreation, and country living. Featuring 3 bedrooms and 1 1/2 baths, the home provides a functional layout with generous living spaces designed for both everyday living and entertaining. Step outside to your own backyard retreat, complete with a beautiful in-ground pool surrounded by peaceful natural surroundings. The expansive property offers plenty of room for outdoor activities, gardening, or simply enjoying the privacy and tranquility of the setting. Conveniently located while still offering a secluded feel, this property presents a rare opportunity to enjoy space, privacy, and lifes

$550,000

3 beds2 baths2,208 sq ft

820 Killingworth Rd, Higganum, CT 06441

Private acres • In-ground pool • Secluded feel

ABOUT THIS HOME
Home with a Pool for sale in Madison, CT:
Opportunity knocks with this aggressively priced shoreline gem located at 25 Riverside, Unit E8 in Clinton! Situated just steps from the water and the famous Lobster Landing, this location is an absolute dream-within easy walking distance to Cedar Island Marina, the Clinton town boat launch, and 3 lovely restaurants. Ready for you to make it your own with your final touches, the owner's decision to leave the kitchen and bathroom unfinished is intentional-to give the new owner the chance to update these spaces to their exact preference and taste. The interior already features great updates to build upon, including classic hardwood floors across the main living area, brand-new carpet in the b

$289,900

2 beds1.5 baths1,008 sq ft

25 Riverside Dr Unit E8, Clinton, CT 06413

In-ground pool • Private back deck • Custom tile shower

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Madison, CT:
A rare opportunity to own in Harborwalk, a desirable shoreline community in Clinton's Riverside neighborhood, just steps from Clinton Harbor and close to marinas, beaches, waterfront dining, and downtown Clinton. An ideal choice for boating enthusiasts, year-round living, or those seeking an easy to maintain Connecticut shoreline retreat. This well maintained 2-bedroom, 1.5-bath townhouse-style condo offers thoughtfully updated living space. Renovated approximately four years ago, it features a stunning custom kitchen by The Kitchen Company, two beautifully updated bathrooms, heated tile floors and a fireplace. Additional upgrades include spray foam insulation between the units for enhanced

$398,000

2 beds1.5 baths1,008 sq ft

25 Riverside Dr Unit A13, Clinton, CT 06413

Custom kitchen • Tennis court • Open green space

ABOUT THIS HOME
Home with a Pool for sale in Madison, CT:
Welcome to 48 Jefferson Circle! Your new home awaits! Nothing to do but move in and enjoy! Beautiful hardwood floors abound. Gorgeous dining room addition with vaulted ceilings full of amazing sunshine, looking over your personal oasis. Although summer is almost over just look at that amazing, refreshing pool and cabana. Imagine the fun gatherings! Downstairs you will find the perfect set up for in-laws, out-laws, extended family or just a great place for multigenerational living. Come make this one your own! (New septic Tank and Distribution box August 2026)

$535,000

4 beds2.5 baths1,220 sq ft

48 Jefferson Cir, Clinton, CT 06413

Dining room addition • Refreshing pool • Cabana

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Madison, CT:
Welcome to 212 Mulberry Point Road, a distinctive contemporary coastal retreat in a cul-de-sac neighborhood offering rare acreage in one of Guilford's most coveted shoreline areas. Beautifully landscaped, with an emphasis on privacy, the property is designed for exceptional indoor-outdoor living, with a large in-ground pool, separate all season hot tub, expansive decking, and an outdoor fireplace under a gazebo. The property is ideal for entertaining, dining, and relaxing. Inside, a sophisticated yet comfortable layout has unique architectural character throughout. The spacious primary suite features its own private loft, creating the perfect setting for a home office, reading nook, or sitt

$1,200,000

3 beds3.5 baths3,645 sq ft

212 Mulberry Point Rd, Guilford, CT 06437

Outdoor fireplace • All season hot tub • Rare acreage

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Madison, CT:
WELCOME to 21 CLARKSON LANE. Set at the end of a coveted cul-de-sac and surrounded by approximately five acres of extraordinary privacy, 21 Clarkson Lane is a rare Connecticut estate offering an exceptional combination of refined living, resort-style amenities, and remarkable future possibilities. The property encompasses two separate building lots, including an approximately 1.9-acre approved buildable lot that is already established and does not require subdivision. Whether envisioned for a future residence, guest house, equestrian use, tennis court, additional acreage, or simply treasured open space, this offering provides a level of flexibility seldom found in the marketplace. A CONNECT

$2,250,000

5 beds5 baths4,190 sq ft

21 Clarkson Ln, Killingworth, CT 06419

Stone walls • Pastoral views • Mature landscaping

Property at 76-R Ivy Way, Durham, CT 06422, 4 beds, 2.5 baths

$699,000

4 beds2.5 baths2,430 sq ft

76-R Ivy Way, Durham, CT 06422

Property at 86 Laurel Ridge Trl, Killingworth, CT 06419, 4 beds, 2.5 baths

$915,000

4 beds2.5 baths2,942 sq ft

86 Laurel Ridge Trl, Killingworth, CT 06419

Property at 3 Medley Ln, Clinton, CT 06413, 4 beds, 2.5 baths

$629,000

4 beds2.5 baths2,151 sq ft

3 Medley Ln, Clinton, CT 06413

Property at 149 Liberty St, Clinton, CT 06413, 3 beds, 2 baths

$479,900

3 beds2 baths1,520 sq ft

149 Liberty St, Clinton, CT 06413

Property at 70 Stepstone Hill Rd, Guilford, CT 06437, 4 beds, 2.5 baths

$719,900

4 beds2.5 baths2,793 sq ft

70 Stepstone Hill Rd, Guilford, CT 06437

Property at 25 Whitewood Rd, Killingworth, CT 06419, 2 beds, 1 bath

$115,900

2 beds1 bath672 sq ft

25 Whitewood Rd, Killingworth, CT 06419

Property at 11 Autumn Ln, Clinton, CT 06413, 3 beds, 2 baths

$639,000

3 beds2 baths2,508 sq ft

11 Autumn Ln, Clinton, CT 06413

Property at 76 Sachem Head Rd, Guilford, CT 06437, 4 beds, 4.5 baths

$2,650,000

4 beds4.5 baths5,620 sq ft

76 Sachem Head Rd, Guilford, CT 06437

Property at 18 Birch Mill Rd, Killingworth, CT 06419, 4 beds, 2.5 baths

$2,195,000

4 beds2.5 baths3,700 sq ft

18 Birch Mill Rd, Killingworth, CT 06419

Property at 23 Welsch Farms Rd, Killingworth, CT 06419, 5 beds, 4 baths

$1,459,000

5 beds4 baths3,978 sq ft

23 Welsch Farms Rd, Killingworth, CT 06419

Property at 379 Whitfield St Unit AS2136, Guilford, CT 06437

$25,500

— beds— baths612 sq ft

379 Whitfield St Unit AS2136, Guilford, CT 06437

Property at 180 Green Hill Rd, Killingworth, CT 06419, 4 beds, 4 baths

$1,299,900

4 beds4 baths4,154 sq ft

180 Green Hill Rd, Killingworth, CT 06419

Property at 379 Whitfield St Unit BN1034, Guilford, CT 06437

$23,500

— beds— baths680 sq ft

379 Whitfield St Unit BN1034, Guilford, CT 06437

Property at 66 High St #38, Guilford, CT 06437, 3 beds, 3 baths

$2,995,000

3 beds3 baths2,983 sq ft

66 High St #38, Guilford, CT 06437

Homes with Pools for Sale in Madison

There are currently 4 homes with pools for sale in Madison at a median listing price of $799K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Madison stay on the market for 49 days and receive 9 offers. This map is refreshed with the newest listings in Madison every 15 minutes.

In the past month, 28 homes have been sold in Madison. In addition to houses in Madison, there were also 20 condos, 0 townhouses, and 1 multi-family unit for sale in Madison last month. Find your dream home in Madison using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Madison are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Madison. If you're looking to sell your home in the Madison area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Madison with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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