Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Save search
Luxury Homes in Madison, CT
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Save search
17 listings
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
3 bedsNew constructionWith a pool

Luxury Homes in Madison, CT

Luxury Homes in Madison, CT

Hide Map
17 Listings
Map

Luxury Homes in Madison, CT

17 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas
  1. 22 Stone Road — photoNew34Active

    $3,200,000

    5 bd · 4 ba · 4,937 sqft

    22 Stone Road, Madison, CT

    Rob McConville · RE/MAX Heritage

  2. listing photo25Active

    $5,000,000

    3 bd · 3 ba · 3,109 sqft

    Address withheld · Madison, CT

    Judy Dannemann · William Raveis Real Estate

  3. 17 Barberry Lane — photo38Active

    $3,000,000

    4 bd · 6 ba · 4,833 sqft

    17 Barberry Lane, Madison, CT

    Todd Gould · William Pitt Sotheby's Int'l

  4. 262 Mungertown Road — photo23Active

    $1,750,000

    4 bd · 4 ba · 2,913 sqft

    262 Mungertown Road, Madison, CT

    Lisa Rollins · Compass Connecticut, LLC

  5. 15 Highland Terrace — photo39Active

    $2,190,000

    5 bd · 3 ba · 3,172 sqft

    15 Highland Terrace, Madison, CT

    John Cronin · Century 21 AllPoints Realty

  6. 148 Mungertown Road — photo40Active

    $1,200,000

    4 bd · 4 ba · 2,338 sqft

    148 Mungertown Road, Madison, CT

    Allison Ciarcia · William Raveis Real Estate

  7. 1209 Durham Road — photo40Active

    $1,200,000

    5 bd · 6 ba · 3,832 sqft

    1209 Durham Road, Madison, CT

    Heather Clinton · Berkshire Hathaway NE Prop.

  8. 1308 Durham Road — photo40Active

    $1,378,800

    3 bd · 3 ba · 2,767 sqft

    1308 Durham Road, Madison, CT

    Nick Prevost · William Raveis Real Estate

  9. 32 Liberty Street — photo30Active

    $1,299,000

    3 bd · 3 ba · 1,188 sqft

    32 Liberty Street, Madison, CT

    Karina Ukhnitska · Real Broker CT, LLC

  10. 77 Silo Hill — photo40Active

    $1,300,000

    5 bd · 4 ba · 4,783 sqft

    77 Silo Hill, Madison, CT

    Cathy Lynch · Coldwell Banker Realty

  11. 26 Bassett Lane — photoPrice Reduced40Active

    $1,950,000

    3 bd · 4 ba · 2,160 sqft

    26 Bassett Lane, Madison, CT

    Steven Koleno · Beycome of Connecticut

  12. 30 Meeting House Lane — photo38Active

    $1,695,000

    5 bd · 4 ba · 3,912 sqft

    30 Meeting House Lane, Madison, CT

    Cathy Lynch · Coldwell Banker Realty

  13. 45 Island Avenue — photoPrice Reduced38Active

    $3,495,000

    5 bd · 6 ba · 5,657 sqft

    45 Island Avenue, Madison, CT

    Meig Walz · Coldwell Banker Realty

  14. 441 Opening Hill Road — photo33Active

    $1,975,000

    4 bd · 2 ba · 3,882 sqft

    441 Opening Hill Road, Madison, CT

    Steve Adkins · Berkshire Hathaway NE Prop.

  15. 81 Strawberry Hill Road — photoPrice Reduced36Active

    $1,975,000

    4 bd · 4 ba · 2,850 sqft

    81 Strawberry Hill Road, Madison, CT

    Cathy Lynch · Coldwell Banker Realty

  16. 23 Sheep Pasture Road — photoPrice Reduced38Active

    $2,295,000

    4 bd · 6 ba · 4,700 sqft

    23 Sheep Pasture Road, Madison, CT

    Jillian Wollman · Wollman Realty

  17. 92 Scotland Avenue — photoPrice Reduced37Active

    $2,290,000

    5 bd · 5 ba · 4,143 sqft

    92 Scotland Avenue, Madison, CT

    Jillian Wollman · Wollman Realty

Explore Madison homes

By price

  • Under $300K
  • Under $500K
  • Under $700K
  • Luxury

By bedrooms

  • 2 beds
  • 3 beds
  • 4 beds
  • 5 beds

By type

  • Single family
  • Townhomes
  • Condos
  • Manufactured homes
  • Multi-family homes
  • Co-ops

By feature

Realty.com

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

Equal Housing OpportunityEqual Housing Lender

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

© 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

Listing data & MLS disclosures

SmartMLS
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.
    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #REB.0790925

    Call Thomas