35 Aileen Drive, Madison, CT 06443
Property image
Property image
FOR SALE
2.36 ACRES

$524,000

  • 3 Beds
  • 2 Baths
  • 1,288 sqft (on 2.36 acres)

35 Aileen Drive, Madison, CT 06443

Est. Mortgage $3,704/mo*
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We estimate this home will sell faster than 98% nearby.

Home Highlights

Property Type
Single-Family Home
Year Built
1978
Lot Size
2.36 acres
Price/Sqft
$407
Parking
2 Car Garage

Local Information

  • Map ViewExplore the area around 35 Aileen Drive.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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. The dishwasher does not work and will not be replaced. Owner is actively looking for suitable housing. Do not lock interior door to garage. Key is for front door dead bolt only. Storm door and center bedroom windows will be repaired/replaced before closing.
Last check for updates: about 12 hours ago
Listing courtesy of Leslie McLennan Richo, (203) 710-2498
William Raveis Real Estate, (203) 710-2498
Source: Smart MLS, MLS#24199405
Also Listed on Smart MLS.
We estimate this home will sell faster than 98% nearby.

Home Details for 35 Aileen Drive

Interior Features

Interior Details
Basement: Full,Partially FinishedNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1288 Square Feet
Appliances & Utilities
Appliances: Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Hot Water,Wood/Coal Stove,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, PatioFoundation: Concrete Perimeter, RaisedNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 1288 Square Feet

Days on Market

Days on Market: 9

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Vertical SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1158988

Price & Status

Price
List Price: $524,000Price Per Sqft: $407
Status Change & Dates
Possession Timing: Negotiable

Active Status

MLS Status: Active

Location

Direction & Address
City: Madison
School Information
Elementary School: Per Board of EdJr High / Middle School: Polson Middle School, Per Board of EdHigh School: Daniel Hand

Agent Information

Listing Agent
Listing ID: 24199405

Building

Building Area
Building Area: 1288 Square Feet

Community

Community Features: Playground, Public Rec Facilities, Shopping/Mall
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 2.36 Acres

Miscellaneous

BasementMls Number: 24199405Attic: Access Via HatchAttribution Contact: (203) 710-2498Above Grade Unfinished Area: 1288

Additional Information

PlaygroundPublic Rec FacilitiesShopping/Mall

Around this home

What Locals Say about Madison

At least 57 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 91 % Say parking is easy

  • 90 % Say yards are well-kept

  • 89 % Say it's dog friendly

  • 88 % Say there's wildlife

  • 85 % Say there's holiday spirit

  • 78 % Say people would walk alone at night

  • 74 % Say it's quiet

  • 66 % Say neighbors are friendly

  • 63 % Say they plan to stay for at least 5 years

  • 62 % Say kids play outside

  • 39 % Say there are community events

  • 31 % Say streets are well-lit

  • 29 % Say it's walkable to grocery stores

  • 26 % Say it's walkable to restaurants

  • 12 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Nancy Bussiere
    "My commute to work is under 15mins. I love the easy access to highways. There is public transportation available but I haven’t used it as of yet"
    0
    Flag
  • Ginavan1
    "Safe,beautiful and family oriented. Beach and hiking places nearby. Great schools and town and local sport leagues for the kids."
    0
    Flag
  • Ginavan1
    "Good schools . Neighbors are nice and welcoming. Good sense of community. Clean, safe and great outdoors."
    0
    Flag
  • Jv4450
    "I’m just trying my luck with this and it doesn’t look too great for the job and the way the company looks I just have no confidence "
    0
    Flag
  • Trulia User
    "I’ve lived here for 30 years. Home prices continue to go up with the NYC families inching this way causing taxes to get out of control. "
    1
    Flag
  • Diana
    "I see people walking dogs but there is no dog park like in neighboring towns. However, there are many walking trails that you can take your leashed dog to walk in."
    4
    Flag
  • Elizabeth L.
    "Great neighborhood. Great schools. Beautiful town. Great library. Great beaches. New England vibe. Shoreline East train takes you to new Haven with direct connection to NYC. "
    2
    Flag
  • Cassidy W.
    "Great place. Been here for 23 years, wouldn’t change a thing. Very small town. Not a lot of commercial business in Madison, close by in Guilford, very local business oriented. "
    1
    Flag
  • Diana
    "People seem friendly enough but aren’t nosy neighbors. I think it would be fairly easy for young families to socially connect."
    2
    Flag
  • Jcimino5
    "Nice community with good school system and organized sports teams. Nice beach and walking trails. Can get a bit crowded in the summer."
    2
    Flag
  • Mike H.
    "A wonderful seaside community. Colonial New England meets the beach. Great Resaurant’s and small businesses. "
    0
    Flag
  • Junedday1
    "I've lived in this neighborhood for 9 years and love it. Great neighbors, quite, well-maintained and very safe."
    3
    Flag
  • Bob B
    "Great community. Families partipate in local activities. Safe town. Beautiful town beach properties. Great local shopping and restaurants. School system is top notch and lots of state parks close by. It’s really a picture perfect town. Lived in Madison for 42 years "
    0
    Flag
  • Robuess
    "Its the best town in America hands down. We love the local restaurants and can ride our bikes to the beach. Friendly locals who will stop and ask if you need help. Very fortunate to have lived here for 40 years!!"
    0
    Flag
  • Joy J.
    "great area to live. Good neighbors, good food. beautiful backyards. Good for animals and nature.?I would definitely suggest living here"
    0
    Flag
  • Pamelajbrown1234
    "Almost everyone has a dog, we take them everywhere. There is a dog park in town. People walk their dogs all over town and down at Hammonasette State Park. Dogs mostly seem very well trained and socialized"
    7
    Flag
  • Nicole L.
    "There is a real sense of community and people actually care about each other here. Schools are excellent and our beaches make it feel like you're always on vacation. "
    0
    Flag
  • Mike H.
    "I’ve lived here since 1990 and love it! There’s everything here, from great dining and great bookstore, coffee shops and terrific local cinema!"
    0
    Flag
  • David F.
    "Great for young families!"
    0
    Flag
  • Robert S.
    "We have lived in Madison for 15 years. This is a great neighborhood with only 12 houses. It is quiet and private as well as being a friendly and considerate group of folks. Mix of retierees and families with close proximity to many local amenities."
    0
    Flag

Market trends in Madison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$710K
$53.67KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$334
$7MoM
Available listings
63
8MoM

Home Value

Trulia Estimate
$508K
Since last month
Increased$2K (+0.3%)
Since last year
Increased$14K (+2.9%)
Since last sale
Increased$283K (+126%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +85% in the last 10 years
MonthEstimated value
2026
September 2026$508K
August 2026$536K
July 2026$507K
June 2026$513K
May 2026$519K
April 2026$507K
March 2026$494K
February 2026$487K
January 2026$483K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
271 Chestnut Hill Road, Killingworth, CT
0.27
Single-Family Home
$620,000
05/29/26
4
2.5
2,590
714 Durham Road, Madison, CT
0.12
Single-Family Home
$725,000
10/29/25
3
3.5
3,933
677 Durham Road, Madison, CT
0.25
Single-Family Home
$730,000
12/23/25
3
2.5
2,112
40 Harkness Drive, Madison, CT
0.22
Single-Family Home
$735,000
07/02/26
4
2.5
2,657
21 Pierce Lane, Madison, CT
0.69
Single-Family Home
$539,000
08/07/26
3
1.5
1,666
33 Harkness Drive, Madison, CT
0.21
Single-Family Home
$770,000
02/18/26
4
2.5
2,797
602 Durham Road, Madison, CT
0.56
Single-Family Home
$745,000
07/30/26
3
2
2,248
89 Summer Hill Road, Madison, CT
0.36
Single-Family Home
$769,000
08/20/26
4
2.5
2,647
37 Pine Drive, Madison, CT
0.53
Single-Family Home
$730,000
12/01/25
4
2.5
2,390
23 Horsebarn Lane, Madison, CT
0.36
Single-Family Home
$855,000
02/02/26
4
3
3,972

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
19 Aileen Drive, Madison, CT 06443
0.09
$674,200
3
2.5
2,440
Off Market
22 Aileen Drive, Madison, CT 06443
0.10
$636,200
4
2.5
1,782
Off Market
728 Durham Road, Madison, CT 06443
0.07
$170,000
-
-
-
Recently Sold
714 Durham Road, Madison, CT 06443
0.12
$752,600
3
3.5
3,933
Off Market
33 Harkness Drive, Madison, CT 06443
0.21
$770,000
4
2.5
2,797
Recently Sold
40 Harkness Drive, Madison, CT 06443
0.22
$735,000
4
2.5
2,657
Recently Sold
688 Durham Road, Madison, CT 06443
0.19
$621,100
3
2
1,926
Off Market
271 Chestnut Hill Road, Killingworth, CT 06419
0.27
$620,000
4
2.5
2,590
Recently Sold
677 Durham Road, Madison, CT 06443
0.25
$730,000
3
2.5
2,112
Recently Sold
16 Harkness Drive, Madison, CT 06443
0.32
$572,900
3
2.5
1,596
Off Market
675 Durham Road, Madison, CT 06443
0.28
$1,386,600
4
3.5
3,435
Off Market

Price and Tax history

DateEventPrice
Aug 24, 2026
Source: Smart MLS #24199405
Listed For Sale
$524,000
Sep 11, 2022
Source: William Raveis Real Estate, Mortgage & Insurance
ListingRemoved
Sep 9, 2022
Source: Smart MLS #170521405
Listed For Sale
$350,000
Jul 30, 2001
Source: Smart MLS #M9063655
Sold
$225,000
Dec 12, 1997
Source: N/A
Sold
$172,000

LGBTQ Local Legal Protections

Leslie McLennan Richo, William Raveis Real Estate, (203) 710-2498
Agent Phone: (203) 710-2498
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.

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Frequently asked questions about 35 Aileen Drive

  • What is the estimated monthly payment for 35 Aileen Drive?
    Based on a $524,000 list price with 20% down at today's rates, the estimated monthly payment for 35 Aileen Drive in Madison, CT is approximately $3,780 (about $2,775 principal & interest, $930 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 35 Aileen Drive compare to homes in Madison?
    35 Aileen Drive in Madison, CT is listed at $524,000, about 26% below the $710K median sale price in Madison.
  • What do residents say about Madison?
    Residents describe Madison, CT as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See homes for sale in Madison, CT.
  • What are the closest schools to 35 Aileen Drive?
    The closest schools to 35 Aileen Drive in Madison, CT are Daniel Hand High School (rated 10/10), Dr. Robert H. Brown Middle School (Elementary, rated 9/10), Kathleen H. Ryerson Elementary School (rated 10/10).
  • Does 35 Aileen Drive have laundry facilities?
    Yes, 35 Aileen Drive in Madison, CT has in-unit laundry.
  • How big is the lot at 35 Aileen Drive?
    The lot at 35 Aileen Drive in Madison, CT is about 2.4 acres.
35 Aileen Drive, Madison, CT 06443 is a 3 bedroom, 2 bathroom, 1,288 sqft single-family home built in 1978. This property is currently available for sale and was listed by Smart MLS on Aug 24, 2026. The MLS # for this home is MLS# 24199405.