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$499,900

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,288 Sq. Ft.
  • 2 Car Garage
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First Time Offered In 25 Years. This contemporary raised ranch, set on 2.36 secluded acres, is located in a quiet cul-de-sac neighborhood just minutes to town. The living room with hardwood floors features a cathedral ceiling with beams, a wood burning fireplace, floor to ceiling windows with double sliders to a deck with built in bench, perfect for morning coffee or evening enjoyment. The adjacent dining room also has sliders to a patio. The kitchen with breakfast bar is waiting for your personal touches. Down the hall you will find 2 spacious guest bedrooms with large closets that share a hall bath. The primary bedroom with walk-in closet has its own full bath. Downstairs is a large family room with a wood stove to keep things cozy and sliders to an additional patio. The laundry is also located on this level. Though located in a private wooded setting, this home is conveniently located to town, beaches, parks and all that Madison has to offer.

Full Property Details for 35 Aileen Dr

General

  • Price: $499,900
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24199405
  • Updated: 9/21/2026
  • Added to Site: 48 day(s) ago

Interior

  • Number of Rooms: 6
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Full Bath, Stall Shower, Walk-In Closet, Hardwood Floor, Main
  • Bedroom 1: Bedroom - Hardwood Floor, Main
  • Bedroom 2: Bedroom - Hardwood Floor, Main

Other Rooms

  • Living Room: Living Room - 2 Story Window(s), Cathedral Ceiling, Balcony/Deck, Fireplace, Sliders, Hardwood Floor, Main
  • Family Room: Family Room - Book Shelves, Built-Ins, Wood Stove, Patio/Terrace, Sliders, Engineered Wood Floor, Lower
  • Dining Room: Dining Room - Patio/Terrace, Sliders, Hardwood Floor, Main

Exterior

  • Exterior Features: Deck, Patio
  • Color: Gray

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking: Under House Garage

Location

  • County: New Haven
  • Driving Directions: Route 79/Durham Rd to Chestnut Hill Rd. 1st left on Summer Hill Rd then immediate left on Aileen Dr. Shared driveway at end of Cul-de-sac. interior lot. House is at top of hill on the left.

School Information

  • Elementary School: Per Board of Ed
  • Middle School: Polson Middle School
  • Intermediate School: Per Board of Ed
  • High School: Daniel Hand

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Baseboard, Hot Water, Wood/Coal Stove, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Raised Ranch
  • Construction Status: No/Resale
  • Exterior Const.: Vertical Siding
  • Basement Desc.: Full, Partially Finished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 1,288
  • Above Ground: 1,288 Sq. Ft.
  • Year Built: 1978

Lot Features

  • Lot Size (Acres): 2.36
  • Zoning: RU-1
  • Lot Description: Interior Lot, Treed, Sloping Lot, On Cul-De-Sac

Financial Considerations

  • Assessment Amount: $286,700
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 1158988

Listed by William Raveis Real Estate, Leslie McLennan Richo

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Listing agent

— 35 Aileen Dr —

  • Leslie McLennan Richo

    William Raveis Real Estate

Agent Contact: (203) 710-2498 Office Contact: (203) 318-3570

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 35 Aileen Dr

School District:Madison School District
NameGradesDistance
Dr. Robert H. Brown Middle School
980 Durham Road, Madison, CT 06443
4-51.1 mi
Kathleen H. Ryerson Elementary School
982 Durham Road, Madison, CT 06443
K-31.2 mi
Walter C. Polson Upper Middle School
302 Green Hill Road, Madison, CT 06443
6-82.2 mi
Daniel Hand High School
286 Green Hill Road, Madison, CT 06443
9-122.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 35 Aileen Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/09/2026
Price Reduced
$499,900
-4.6%
MLS
8/24/2026
Listed
$524,000
132.89%
MLS
7/30/2001
Sold
$225,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 35 Aileen Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$6,431
2%
$286,700
—
2023
$6,307
9%
$286,700
48%
2023
$5,811
2%
$193,900
—
2022
$5,703
2%
$193,900
—
2021
$5,594
2%
$193,900
—
2020
$5,497
—
$193,900
—
2019
$5,497
—
$193,900
-1%
2018
$5,513
3%
$196,600
—
2017
$5,367
3%
$196,600
—
2016
$5,208
3%
$196,600
—
2015
$5,064
2%
$196,600
—
2014
$4,948
2%
$196,600
-17%
2010
$4,830
—
$236,900
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by William Raveis Real Estate, Leslie McLennan Richo

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35 Aileen Drive, Madison, CT 06443 (MLS# 24199405) is a Single Family property with 3 bedrooms and 2 full bathrooms. 35 Aileen Drive is currently listed for $499,900 and was received on August 24, 2026. Want to learn more about 35 Aileen Drive? Do you have questions about finding other Single Family real estate for sale in Madison? You can browse all Madison real estate or contact a Coldwell Banker agent to request more information.

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