Madison Real Estate

Luxury Homes for Sale in Madison, CT

Welcome to your dedicated resource for luxury homes for sale in Madison, CT. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Madison, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the luxury properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Luxury Homes for Sale in Madison, CT

$3,495,000
5 Beds ⋅ 6 Baths ⋅ 24166497 MLS
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 equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see.

45 Island Ave, Madison
$2,650,000
4 Beds ⋅ 5 Baths ⋅ 24159028 MLS
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 home is thoughtfully designed for both elegant living and everyday comfort, featuring expansive, light-filled spaces and exquisite millwork throughout. The custom chef's kitchen is a true centerpiece, appointed with premium appliances, striking imported granite countertops, and impeccable detailing. A grand entryway welcomes you with a sweeping staircase and a beautifully crafted coffered ceiling, setting the tone for the quality and sophistication found in every room. Layout designed for first floor primary suite. This is a home for those who appreciate enduring design, superior construction, and a setting that feels worlds away-yet remains close to everything Madison has to offer.

24 Indigo Trl, Madison
$2,500,000
C7516446 MLS
A rare opportunity to own three income-producing properties in the charming heart of Madison, Florida — a peaceful, historic town known for its southern hospitality and small-town growth. This portfolio includes 649 W Base St, 643 W Base St, and 912 SW Pinckney St, offering a total of three individual properties, each with its own character and potential. All units are conveniently located within minutes of downtown Madison, schools, shops, and dining — yet set on spacious lots that offer privacy, mature landscaping, and room to expand. Together, the properties total over an acre of land, providing investors or multi-family owners the ideal blend of comfort and long-term appreciation. Each unit features independent entrances, separate utilities, and functional layouts, giving you the freedom to rent for maximum cash flow, transform them into a charming short-term rental portfolio or Build a new Construction. Whether you’re a first-time investor, Builder, experienced landlord, or visionary seeking passive income in a quiet North Florida community, this trio offers an exceptional cap rate opportunity in a market with steady rental demand and limited multi-unit inventory. Nestled near major routes like Base Street (US-90) and just a short drive from I-10, these properties combine convenience, flexibility, and growth potential. With their solid structures, walkable location, and multiple income streams, this is the kind of deal that rarely comes around in Madison County- Three Properties, One opportunity, Endless potential.

649 W Base Street, Madison
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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.