237 Oak Leaf Dr, Winona, MN 55987
OFF MARKET

$491,300

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,856 sqft (on 0.46 acres)

237 Oak Leaf Dr, Winona, MN 55987

Est. Refi. Payment $2,970/mo*
Refinance Your Home
Currently Off Market - Sold May 2, 2022 for $416,000

Home Value

Trulia Estimate
$491K
Since last month
Decreased$2K (-0.4%)
Since last year
Increased$13K (+2.8%)
Since last sale
Increased$75K (+18%)
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 +64% in the last 10 years
MonthEstimated value
2026
August 2026$491K
July 2026$493K
June 2026$492K
May 2026$487K
April 2026$486K
March 2026$481K
February 2026$473K
January 2026$469K
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
217 Oak Leaf Dr, Winona, MN
0.09
Single-Family Home
$460,000
07/17/26
4
3.5
2,026
65 Forest Oak Ct, Winona, MN
0.17
Single-Family Home
$495,000
08/29/25
4
3
3,094
78 Shady Oak Ct, Winona, MN
0.27
Single-Family Home
$765,000
06/22/26
5
3.5
5,882
56 Rivers Oak Ct, Winona, MN
0.44
Single-Family Home
$595,000
02/27/26
6
3.5
4,235
75 Debi Lei Dr, Winona, MN
0.65
Single-Family Home
$461,000
12/29/25
5
2.5
3,414
943 Birch Blvd, Winona, MN
0.50
Single-Family Home
$444,000
06/26/26
5
2
2,496
384 Valley Oaks Dr, Winona, MN
0.64
Single-Family Home
$461,000
03/02/26
4
3
3,234
1628 Valley View Dr, Winona, MN
0.86
Single-Family Home
$545,000
04/22/26
3
4
3,431
1614 Valley View Dr, Winona, MN
0.87
Single-Family Home
$400,000
07/07/26
4
2
2,900
63 Debi Lei Dr, Winona, MN
0.67
Single-Family Home
$390,000
09/10/25
3
2
2,018

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
245 Oak Leaf Dr, Winona, MN 55987
0.04
$463,900
5
3.5
4,015
Off Market
229 Oak Leaf Dr, Winona, MN 55987
0.04
$477,600
4
3.5
2,602
Off Market
239 Valley Oaks Dr, Winona, MN 55987
0.07
$410,100
4
2
2,464
Off Market
217 Oak Leaf Dr, Winona, MN 55987
0.09
$460,000
4
3.5
2,026
Recently Sold
218 Oak Leaf Dr, Winona, MN 55987
0.09
$438,200
4
3
2,960
Off Market
258 Oak Leaf Dr, Winona, MN 55987
0.10
$539,000
5
3.5
3,464
Off Market
255 Valley Oaks Dr, Winona, MN 55987
0.11
$426,800
4
3.5
2,793
Off Market
51 Oak Park Ct, Winona, MN 55987
0.14
$537,100
5
3
3,026
Off Market
57 Rivers Ln, Winona, MN 55987
0.14
$298,300
2
2
1,320
Off Market
61 Forest Oak Ct, Winona, MN 55987
0.17
$506,400
4
3.5
3,725
Off Market
65 Forest Oak Ct, Winona, MN 55987
0.17
$547,300
4
3
3,094
Off Market
69 Forest Oak Ct, Winona, MN 55987
0.17
$60,000
-
-
-
Recently Sold

Local Information

  • Map ViewExplore the area around 237 Oak Leaf Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1988
Lot Size
0.46 acres
Living Area
3,856 sqft
Price/Sqft
$127
Parking
Garage

About this House

This single-family home is located at 237 Oak Leaf Dr, Winona, MN. 237 Oak Leaf Dr is in Winona, MN and in ZIP code 55987. This property has 4 bedrooms, 4 bathrooms and approximately 3,856 sqft of floor space. This property has a lot size of 0.46 acres and was built in 1988.
237 Oak Leaf Dr, Winona, MN 55987 is a 4 bedroom, 4 bathroom, 3,856 sqft single-family home built in 1988. It last sold for $416,000 on May 2, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $491,300, with a rent estimate of $3,411/month.

Home Details for 237 Oak Leaf Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Interior Details
Number of Rooms: 9Types of Rooms: Dining Room, Family Room
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Stone, Vinyl, Brick, Cement Concrete
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.46 acres

Price and Tax history

DateEventPrice
May 2, 2022
Source: NorthstarMLS as distributed by MLS GRID #6166745
Sold
$416,000
Mar 22, 2022
Source: NorthstarMLS as distributed by MLS GRID #6166745
Pending
$390,000
Mar 21, 2022
Source: NorthstarMLS as distributed by MLS GRID #6166745
Listed For Sale
$390,000
Feb 25, 2019
Source: NorthstarMLS as distributed by MLS GRID #5032927
Sold
$285,000
Jan 16, 2019
Source: Agent Provided
Pending
$289,900

Market trends in Winona

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$249K
$3.95KMoM
Sale-to-List Price
101.8%
0.7%MoM
Price per sq ft
$126
$5MoM
Available listings
96
10MoM

Around this home

What Locals Say about Winona

At least 110 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 80 % Say parking is easy

  • 80 % Say car is needed

  • 76 % Say there are sidewalks

  • 75 % Say yards are well-kept

  • 72 % Say there's holiday spirit

  • 68 % Say kids play outside

  • 65 % Say people would walk alone at night

  • 61 % Say it's quiet

  • 57 % Say neighbors are friendly

  • 51 % Say there's wildlife

  • 50 % Say streets are well-lit

  • 43 % Say it's walkable to restaurants

  • 41 % Say it's walkable to grocery stores

  • 38 % Say they plan to stay for at least 5 years

  • 32 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Jzafft
    "We’ve lived in this neighborhood for almost 30 years. Everyone is friendly and lookout for each other. "
    0
    Flag
  • Joe Cooper
    "Never had to think about it. Just get in my car and go. 10 min later I am on the other side of town. That sun in my eyes is not fun."
    0
    Flag
  • Jo.kolter
    "You can get anywhere (by car) in 5 minutes, fifteen minutes if you happen to get stuck behind a train."
    1
    Flag
  • Alexandru S.
    "Short and effortless. Best I have ever had, and I have lived in three other states in the US. Drivers are especially courteous and careful."
    8
    Flag
  • Teyanna R.
    "Steamboat Days is always a great time during the summer! It’s great for being out your family and seeing familiar faces that you haven’t in awhile."
    0
    Flag
  • Piggylove36
    "The perfect mix of college kids, old people, and families. Good school system and lots to do! Great area overall"
    0
    Flag
  • Love L. F.
    "It’s a great area for kids but at the same time u have to watch for people on drugs in certain areas "
    0
    Flag
  • Star O.
    "Where I live is mostly college students and they are great for the most part. a little loud on weekends but love it "
    0
    Flag
  • Shawneepartain
    "it's a great area, centrally located in the perfect, quiet area. I might move but for a career change, not because I dont love the area."
    1
    Flag
  • Donmarniquewallace
    "I been in Winona for about four years now & there are jobs, great food, good people & opportunities in most ways you can think of to get your life on track. It’s a place to go to school, start a family, grow old, retire & even open a small business if possible. Winona also has a very small number of crimes, so little of violence & more then enough police to secure all of this wonderful town"
    0
    Flag
  • sammeg
    "This is a typical family neighborhood, rather than rental property. Because we are so close to the pool, it's a great area for families. We are a quiet and happy neighborhood."
    0
    Flag
  • W_triplett
    "Lovely views. Quiet area, with respectful neighbors and limited traffic. Must see the street to appreciate."
    0
    Flag
  • Lynn S.
    "This is one of the nicest neighborhoods in all of Winona. It's so peaceful because of the housing being tucked into the valley behind St. Mary's University. Lots of great theater and music close by. Plenty of wildlife. Park right across the house includes tennis court and beautiful playground area. Great family neighborhood. Good mixture of professionals."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 237 Oak Leaf Dr

  • What is 237 Oak Leaf Dr estimated to be worth?
    Trulia's estimated value for 237 Oak Leaf Dr in Winona, MN is $491,300.
  • What is the price history for 237 Oak Leaf Dr?
    237 Oak Leaf Dr in Winona, MN last sold for $416,000 in May 2022.
  • Is Winona a buyer's or seller's market?
    Winona is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winona?
    The median sale price in Winona is $249K. That is up $3.95K from the prior month.
  • Does 237 Oak Leaf Dr have air conditioning?
    Yes, 237 Oak Leaf Dr in Winona, MN has air conditioning.
  • How big is the lot at 237 Oak Leaf Dr?
    The lot at 237 Oak Leaf Dr in Winona, MN is about 0.46 acres (19,907 sq ft).

Explore by feature - Pet Friendly

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