1069 Winged Foot Dr, Oregon, WI 53575
OFF MARKET

1069 Winged Foot Dr
Oregon, WI 53575

  • 5 Beds
  • 4 Baths
  • 5,331 sqft (on 0.52 acres)

$1,156,500

Trulia Estimate
as of Jun 19, 2026
Est. Refi. Payment $7,312/mo*

$1,156,500

Trulia Estimate
as of Jun 19, 2026
Est. Refi. Payment $7,312/mo*
5 Beds
4 Baths
5,331 sqft
(on 0.52 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Situated amidst emerald greens of Legend at Bergamont, luxury home combines sophistication + comfort. Greeted by expansive windows framing panoramic views of 10th + 18th fairways. Hardwood floors thru ML offering dramatic great room w/vaulted ceiling + fireplace, chef's kitchen w/center island, pro appliances + eat-in breakfast bar. DR features custom cabinets + wine fridge. Escape to primary ensuite w/private balcony, fireplace + spa bath. Office, 2 addtl beds, 1.5 baths, & mudroom w/laundry complete 1st floor. LL boasts XL rec room w/wet bar, exercise room, wine & theater room, 2 beds + 1.5 baths. Outdoor living at its finest w/stunning golf views from 3 season porch w/wood burning fireplace, expansive deck + LL walkout patio w/ firepit. Steps to clubhouse, golf, tennis & pool & dining.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from July 11, 2024

Home Highlights

Parking
3 Car Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
13 days ago

Home Details for 1069 Winged Foot Dr

Interior Features

Interior Details
Basement: 8'+ Ceiling,Finished,Full,Full Size Windows/Exposed,Sump Pump,Walk-Out AccessNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Dining Room, Kitchen, Living RoomWet Bar
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 2Number of Bathrooms (main level): 3
Dimensions and Layout
Living Area: 5331 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Washer, Dryer, Water Softener IncludedDryerLaundry: Main LevelWasher
Heating & Cooling
Heating: Forced Air,Radiant FloorHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Fireplace: 3+ fireplaces, Gas, Wood BurningHas a Fireplace
Levels, Entrance, & Accessibility
Stories: 1Levels: One
Security
Security: Security System

Exterior Features

Exterior Home Features
Patio / Porch: Deck, PatioExterior: Sprinkler system, Electronic pet containmnt
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Additional Parking,Attached,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2806 Square Feet

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Stone, Stucco
Property Information
Not Included in Sale: seller's personal belongingsIncluded in Sale: range/oven, refrigerator, dishwasher, disposal, some window coverings, washer/dryer, sauna, treadmill, elliptical, TV+speakers in workout rm, weight machine, horse riding simulator, pool table/equipment, dartboard, LL bar stools, entire move room, grill -con't in b2b remarksParcel Number: 050910446711

Price & Status

Price
List Price: $1,100,000
Status Change & Dates
Off Market Date: Sat Apr 27 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: OregonCommunity: Bergamont
School Information
Elementary School: Call School DistrictElementary School District: OregonJr High / Middle School: OregonJr High / Middle School District: OregonHigh School: OregonHigh School District: Oregon

Building

Building Area
Building Area: 5331 Square Feet

Lot Information

Lot Area: 0.52 acres

Listing Info

Special Conditions: Restrictions/Covenants

Offer

Listing Terms: Arms Length

Miscellaneous

BasementMls Number: 1975000Above Grade Unfinished Area: 2806
Last check for updates: about 2 hours ago
Listed by Chas Martin
Sprinkman Real Estate
Bought with: Paul Haviland, Stark Company, REALTORS
Source: SCWMLS, MLS#1975000

Price History for 1069 Winged Foot Dr

DatePriceEventSource
07/15/2024$1,065,000Sold
N/A
05/01/2024$1,100,000ContingentWIREX MLS #1975000
04/27/2024$1,100,000Listed For SaleWIREX MLS #1975000
10/15/2013$691,800Sold
N/A
08/20/2013$699,999PriceChange
Agent Provided
05/01/2013$739,000PriceChange
Agent Provided
03/07/2013$749,000Listed For SaleAgent Provided
02/02/2013$799,000ListingRemovedAgent Provided
09/05/2012$799,000Listed For SaleAgent Provided

Market trends in Oregon

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
63
6
MoM
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Property Tax and Assessment

Year2024
Tax$15,998
Assessment$1,019,400
Home facts updated by county records

Homeowner tools

Estimated monthly rent$5,109/mo

Homes for rent near 1069 Winged Foot Dr

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Comparable Sales for 1069 Winged Foot Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.16
Single-Family Home
$1,200,000
11/17/25
5
4.5
5,729
0.33
Single-Family Home
$1,000,000
09/02/25
5
3.5
4,975
0.30
Single-Family Home
$1,019,900
11/05/25
5
3.5
4,154
0.39
Single-Family Home
$1,110,000
08/05/25
5
3.5
4,608
0.33
Single-Family Home
$1,275,000
05/29/26
4
4
4,087
0.28
Single-Family Home
$1,346,300
08/04/25
6
5.5
9,220
0.50
Single-Family Home
$1,174,000
05/18/26
4
4
4,891
0.33
Single-Family Home
$876,100
07/31/25
5
3.5
3,800
0.63
Single-Family Home
$1,225,000
08/15/25
5
4.5
4,881
0.67
Single-Family Home
$920,000
01/28/26
5
3.5
4,211

Nearby homes

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Assigned Schools

These are the assigned schools for 1069 Winged Foot Dr.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Oregon

At least 64 Trulia users voted on each feature.
  • 94 % Say parking is easy

  • 94 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say kids play outside

  • 86 % Say people would walk alone at night

  • 85 % Say yards are well-kept

  • 84 % Say car is needed

  • 80 % Say streets are well-lit

  • 80 % Say there's holiday spirit

  • 77 % Say it's quiet

  • 68 % Say it's walkable to restaurants

  • 68 % Say they plan to stay for at least 5 years

  • 68 % Say neighbors are friendly

  • 58 % Say there's wildlife

  • 48 % Say it's walkable to grocery stores

  • 43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Tanya Hoppe
    "Friendly and family orientated little Town with great school district. Our neighbors are great and watch out for each other. "
  • Khockett58
    "Village Oregon Great place to live. Great schools & sport Great food places to eat. Doctor clinics Gad stations Banks. Small town but close to drive in to Madison or Stoughton And other cities "
  • Lysagrant
    "15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
  • Tjrbackstroker
    "A quick drive up to Madison. The area is very drivable with not too much traffic. It is very easy to get on the highway."
  • Kelly J. P.
    "Love it here! Best move to call this home for our family to grow. Super nice community. We love our neighbors and enjoy to small town feel that Oregon has to offer & also super close to Madison for fun nights out!"
  • Ken D.
    "Great schools, convenient to madison, stoughton and Fitchburg. Housing market is booming, low crime"
  • Rachel
    "To always keep an eye on your kids no matter how safe a neighborhood is deemed to be. Oregon is a great place to live!"
  • miltydog
    "Wonderful schools and a strong sense of community"
  • Donna R. B.
    "Very private rural subdivision....may be a longer drive to madison but for the beautiful lot and privacy a huge bonus"
  • Stevie K.
    "If you like your privacy, multi level living, looking out the back you feel as if you are in the woods! Lots of updates and well cared for. Great neighbors, I used to be one but moved out West, so I have personally been inside and it's great! It is located on a private circle with little traffic! It's definitely a must see!"
  • Stefan
    "This area of Oregon is excellent. The schools are the best. The neighborhoods around Lincoln Road, County A and Hillcrest are nice, but, drivers have no regard for safety at all. Stay off these roads if you bike or run. Farm families are very nice, too. You will love bringing up children in this area. Oregon is the best community in the Madison area for kids and your families to live."

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Off Market Homes Near 1069 Winged Foot Dr

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1069 Winged Foot Dr, Oregon, WI 53575 is a 5 bedroom, 4 bathroom, 5,331 sqft single-family home built in 2005. This property is not currently available for sale. 1069 Winged Foot Dr was last sold on Jul 15, 2024 for $1,065,000 (3% lower than the asking price of $1,100,000). The current Trulia Estimate for 1069 Winged Foot Dr is $1,156,500.