742 Leeward Ln, Oregon, WI 53575
Property image
Property image
OFF MARKET

$449,100

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 1,420 sqft

742 Leeward Ln, Oregon, WI 53575

Est. Refi. Payment $3,053/mo*
Refinance Your Home
Currently Off Market - Sold Jul 11, 2025 for $440,000

Home Value

Trulia Estimate
$449K
Since last month
Decreased$5K (-1%)
Since last year
Increased$7K (+1.7%)
Since last sale
Increased$8K (+1.9%)
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 +83% in the last 10 years
MonthEstimated value
2026
September 2026$448K
August 2026$453K
July 2026$453K
June 2026$453K
May 2026$455K
April 2026$456K
March 2026$456K
February 2026$451K
January 2026$447K
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
617 Windward Way, Oregon, WI
0.12
Single-Family Home
$401,000
08/28/26
3
2.5
1,447
1129 Lincoln Rd, Oregon, WI
0.03
Single-Family Home
$466,000
04/30/26
4
3
2,381
565 Oakwood Dr, Oregon, WI
0.30
Single-Family Home
$512,500
05/06/26
3
2
1,800
760 Scott St, Oregon, WI
0.35
Single-Family Home
$430,000
08/31/26
3
2.5
1,880
564 S Burr Oak Ave, Oregon, WI
0.23
Single-Family Home
$490,000
02/23/26
4
3
2,400
941 Foxfield Rd, Oregon, WI
0.47
Single-Family Home
$431,000
09/11/26
3
2.5
1,940
835 S Main St, Oregon, WI
0.38
Single-Family Home
$430,000
09/26/25
4
3
1,944
489 Cherry Wood Dr, Oregon, WI
0.45
Single-Family Home
$453,000
08/31/26
3
2.5
2,137
865 Miller Dr, Oregon, WI
0.40
Single-Family Home
$400,000
06/18/26
3
2
1,800
434 S Burr Oak Ave, Oregon, WI
0.37
Single-Family Home
$499,900
06/10/26
4
3
2,438

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
1129 Lincoln Rd, Oregon, WI 53575
0.03
$466,000
4
3
2,381
Recently Sold
753 Leeward Ln, Oregon, WI 53575
0.04
$499,100
4
3.5
2,348
Off Market
648-652 S Burr Oak Ave, Oregon, WI 53575
0.12
$578,800
6
4
3,040
Off Market
1144 S Perry Pkwy, Oregon, WI 53575
0.12
$430,700
4
3
1,743
Off Market
617 Windward Way, Oregon, WI 53575
0.12
$401,000
3
2.5
1,447
Recently Sold
1121-1123 Union Rd, Oregon, WI 53575
0.14
$525,000
6
3
2,808
Recently Sold
625 Stonebriar Ln, Oregon, WI 53575
0.16
$439,600
3
2.5
1,588
Off Market
624-628 S Burr Oak Ave, Oregon, WI 53575
0.16
$618,800
6
3
3,584
Off Market
1133-1135 Union Rd, Oregon, WI 53575
0.16
$585,700
6
4
3,400
Off Market
862 Leeward Ln, Oregon, WI 53575
0.18
-
3
2.5
2,784
Off Market
1137-1139 Union Rd, Oregon, WI 53575
0.17
$567,400
6
4
2,864
Off Market

Local Information

  • Map ViewExplore the area around 742 Leeward Ln.
  • Schools2 Preschool Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1998
1,420 sqft
$316/sqft
2 Car Garage

About this House

Curb appeal! Wonderfully maintained brick front two-story located across the street from park. Enjoy outdoor time on back deck & in spacious fenced backyard. No-fuss perennial landscaping gives you beautiful foliage throughout the summer. Comfortable main level living space flows nicely from kitchen to dining area to living room. Ample natural light and breakfast bar in kitchen with stainless appliances. Primary suite includes walk in closet. Basement ready for your personal touch, insulation, tuff-n-dry waterproofing, & framing already complete. Don't miss it!
742 Leeward Ln, Oregon, WI 53575 is a 3 bedroom, 3 bathroom, 1,420 sqft single-family home built in 1998. It last sold for $440,000 on Jul 11, 2025 (10% above the $399,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $449,100, with a rent estimate of $2,448/month.
Last check for updates: about 7 hours ago
Listed by Allie Nicholson
Compass Real Estate Wisconsin
Husky Homes Team
Compass Real Estate Wisconsin
Bought with: Tim Roehl, Coldwell Banker Real Estate Group
Source: SCWMLS, MLS#1999027

Home Details for 742 Leeward Ln

Active Status

MLS Status: Sold

Interior Features

Interior Details
Basement: FullNumber of Rooms: 5Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1420 Square Feet
Appliances & Utilities
Utilities: Cable AvailableAppliances: Water Softener IncludedLaundry: Lower Level
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Fireplace: GasHas a Fireplace
Levels, Entrance, & Accessibility
Stories: 2Levels: Two

Exterior Features

Exterior Home Features
Patio / Porch: DeckFencing: FencedFoundation: Poured concrete foundatn
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: 2 car,Attached,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1420 Square Feet

Property Information

Year Built
Year Built: 1998
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Brick, Stone, Vinyl Siding
Property Information
Not Included in Sale: Seller's personal property.Included in Sale: Refrigerator, Range/Oven, Dishwasher, Microwave, Disposal, Washer/Dryer, Window Coverings, Water SoftenerParcel Number: 050911463573

Price & Status

Price
List Price: $399,900
Status Change & Dates
Off Market Date: Thu May 29 2025

Location

Direction & Address
City: OregonCommunity: Windcrest
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: 1420 Square Feet

Lot Information

Lot Area: 9583.2 sqft

Offer

Listing Terms: Arms Length

Miscellaneous

BasementMls Number: 1999027Above Grade Unfinished Area: 1420

Price and Tax history

DateEventPrice
Jul 11, 2025
Source: N/A
Sold
$440,000
Jun 2, 2025
Source: WIREX MLS #1999027
Pending
$399,900
May 29, 2025
Source: WIREX MLS #1999027
Listed For Sale
$399,900
Sep 17, 2020
Source: N/A
Sold
$308,500
Jul 17, 2020
Source: Agent Provided
PriceChange
$309,900
Price decreased by 5%

Market trends in Oregon

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$535K
$4.17KMoM
Sale-to-List Price
—
Price per sq ft
$223
$18MoM
Available listings
43
8MoM

Around this home

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. "
    0
    Flag
  • 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 "
    0
    Flag
  • Lysagrant
    "15 minute drive from Madison. No public transportation. Easy access to rate 14. Not much traffic even at rush hour."
    0
    Flag
  • 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."
    0
    Flag
  • 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!"
    2
    Flag
  • Ken D.
    "Great schools, convenient to madison, stoughton and Fitchburg. Housing market is booming, low crime"
    0
    Flag
  • 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!"
    1
    Flag
  • miltydog
    "Wonderful schools and a strong sense of community"
    0
    Flag
  • Donna R. B.
    "Very private rural subdivision....may be a longer drive to madison but for the beautiful lot and privacy a huge bonus"
    0
    Flag
  • 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!"
    0
    Flag
  • 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."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 742 Leeward Ln

  • What is 742 Leeward Ln estimated to be worth?
    Trulia's estimated value for 742 Leeward Ln in Oregon, WI is $449,100.
  • What is the price history for 742 Leeward Ln?
    742 Leeward Ln in Oregon, WI last sold for $440,000 in July 2025.
  • Is Oregon a buyer's or seller's market?
    Oregon is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Oregon?
    The median sale price in Oregon is $535K. That is down $4.17K from the prior month.
  • Does 742 Leeward Ln have air conditioning?
    Yes, 742 Leeward Ln in Oregon, WI has air conditioning.
  • Does 742 Leeward Ln have laundry facilities?
    Yes, 742 Leeward Ln in Oregon, WI has laundry facilities.

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