101 Winding Road

Madison, CT
$ 379,900 Beds 4 Baths 2 Sq 1,848
Monthly Estimate* How much can I afford?

This updated home located on a quiet cul-de-sac is in mint condition! Its natural setting is highlighted with a rock garden with colorful perennials and trees surrounding the backdrop (with seasonal migrating birds and nesting owls). The landscaping and aesthetics combine for an inviting curb appeal. Inside you’ll notice refinished hardwood flooring, crown molding, and a large bay window that brings in natural light to the open space. Sliders, in the dining room and kitchen, lead to a spacious and private deck. The kitchen has cherry flooring, newer stainless-steel appliances, all granite countertops, hardwood cabinetry, built-in desk and bookshelf, plus a built-in table/island for dining. The master bedroom has direct access to the remodeled full bath with a jetted tub. Other bedrooms have custom built-ins, bookshelves, desks & a window seat. The lower level also has hardwood floors, a 2nd bath, utility room, storage closets, a family room with a fireplace with wood stove insert, custom mantle, bookshelves, and a slider to a patio and tranquil backyard. A 4th bedroom is perfect for a home office or in-law space. Energy efficiency has been improved with new insulation in most walls, attic, reduced air infiltration, insulated garage with new doors, and insulated windows and sliders. A whole house fan & attic vent fan keeps the home comfortable in summer and utility bills low year-round. It also has central air. Newer roof, driveway, water system & fresh paint. See it soon!


  • Price
  • $ 379,900
  • Lot Size
  • 1.46 Acres
  • Bedrooms
  • 4
  • Sqr Footage
  • 1,848
  • Full Bathrooms
  • 2
  • Year Built
  • 1971
  • Half Bathrooms
  • 0
  • City, Zip
  • Madison
  • Taxes
  • 5693
  • County
  • Style
  • Raised Ranch
  • Area
  • MLS#
  • 170329106
  • Zip
  • 06443
Listing Provided by: Berkshire Hathaway NE Prop.



Elementary School Per Board of Ed
Energy Features Extra Insulation, Programmable Thermostat, Thermopane Windows
Handicap Features Bath Grab Bars, Multiple Entries/Exits
High School Daniel Hand
Intermediate School Per Board of Ed
Middle School/High School Brown
Nearby Amenities Basketball Court, Golf Course, Health Club, Park, Private School(s), Shopping/Mall, Stables/Riding, Tennis Courts
Neighborhood N/A
New Construction Type No/Resale
Property Type Single Family For Sale
Status Show
Style Raised Ranch
Tax Year July 2020-June 2021
Year Built 1971
Year Built Source Public Records
Zoning RU-1

Interior Features

Appliances Included Electric Cooktop, Oven/Range, Microwave, Range Hood, Dishwasher, Washer, Electric Dryer
Attic Description Pull-Down Stairs, Access Via Hatch
Basement Description Partial With Walk-Out, Partially Finished, Heated, Garage Access, Liveable Space
Beds Total 4
Cooling System Attic Fan, Central Air, Whole House Fan
Fireplaces Total 1
Fuel Tank Location Above Ground
Full Baths 2
Heat Fuel Type Oil
Heat Type Baseboard, Hot Water, Wood/Coal Stove
Hot Water Description Domestic, Oil
Interior Features Auto Garage Door Opener, Cable - Available, Cable - Pre-wired
Laundry Room lower level
Laundry Room Info Lower Level
Room Count 8
Rooms Additional Foyer
Sq Ft Est Heated Above Grade 1288
Sq Ft Est Heated Below Grade 560
Sq Ft Total 1848
Total Baths 2.00
Total Rooms 8

Exterior Features

Acres 1.4600
Driveway Type Private, Paved, Asphalt
Exterior Features Deck, Garden Area, Gutters, Lighting, Patio, Shed, Stone Wall, Underground Utilities
Foundation Concrete
Garage Parking Info Under House Garage, Paved
Garages Number 2
Lot Description On Cul-De-Sac, Lightly Wooded
Roof Information Asphalt Shingle
Sewage System Septic
Siding Cedar, Wood
Water Source Private Well
Waterfront Description Not Applicable


  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Master On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator


Per Month

Based on the average sale price from the Wolcott, CT office

  • Monthly Principal & interest $1,939
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 4.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.


Elementary School Per Board of Ed Elementary School
Middle School Brown Middle School
High School Daniel Hand High School

Price History

8/24/2020 Listed $390,000
9/23/2020 3% - $379,900

Property vs Zip Code Average in 06443

AVG $500K
AVG $8,342
AVG 20
Year Built
AVG 1957


101 Winding Road Madison, CT is a Single Family Home for sale at $379900 with 1848 sqft and a lot size of 1.46 Acres Acre(s). 101 Winding Road Madison has 4 bedrooms, 2 baths and was built in 1971. The property's zip code is 06443 which is in Madison, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 4.38% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.