229 Oak Leaf Dr, Winona, MN 55987
OFF MARKET

$477,600

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 2,602 sqft (on 0.45 acres)

229 Oak Leaf Dr, Winona, MN 55987

Est. Refi. Payment $2,917/mo*
Refinance Your Home
Currently Off Market - Sold Oct 3, 2023 for $430,000

Home Value

Trulia Estimate
$478K
Since last month
Decreased$4K (-0.8%)
Since last year
Increased$14K (+2.9%)
Since last sale
Increased$48K (+11.1%)
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 +72% in the last 10 years
MonthEstimated value
2026
August 2026$478K
August 2026$478K
July 2026$482K
June 2026$480K
May 2026$477K
April 2026$475K
March 2026$471K
February 2026$463K
January 2026$457K
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
0.05
Single-Family Home
$460,000
07/17/26
4
3.5
2,026
943 Birch Blvd, Winona, MN
0.47
Single-Family Home
$444,000
06/26/26
5
2
2,496
75 Debi Lei Dr, Winona, MN
0.63
Single-Family Home
$461,000
12/29/25
5
2.5
3,414
78 Shady Oak Ct, Winona, MN
0.31
Single-Family Home
$765,000
06/22/26
5
3.5
5,882
384 Valley Oaks Dr, Winona, MN
0.67
Single-Family Home
$461,000
03/02/26
4
3
3,234
56 Rivers Oak Ct, Winona, MN
0.48
Single-Family Home
$595,000
02/27/26
6
3.5
4,235
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
0.65
Single-Family Home
$390,000
09/10/25
3
2
2,018
1628 Valley View Dr, Winona, MN
0.85
Single-Family Home
$545,000
04/22/26
3
4
3,431
182 Tree Tops Ln, Winona, MN
0.68
Single-Family Home
$385,000
12/01/25
3
2.5
2,528

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
225 Oak Leaf Dr, Winona, MN 55987
0.02
$479,000
4
3.5
3,000
For Sale
217 Oak Leaf Dr, Winona, MN 55987
0.05
$460,000
4
3.5
2,026
Recently Sold
218 Oak Leaf Dr, Winona, MN 55987
0.06
$436,500
4
3
2,960
Off Market
245 Oak Leaf Dr, Winona, MN 55987
0.08
$464,100
5
3.5
4,015
Off Market
239 Valley Oaks Dr, Winona, MN 55987
0.09
$410,100
4
2
2,464
Off Market
57 Rivers Ln, Winona, MN 55987
0.12
$298,300
2
2
1,320
Off Market
22224 E Burns Valley Rd, Winona, MN 55987
0.20
$470,500
4
3.5
2,984
Off Market
97 Rivers Ln, Winona, MN 55987
0.16
$320,000
3
2
2,400
Recently Sold
73 Rivers Ln, Winona, MN 55987
0.15
$275,000
2
2
1,760
Recently Sold
258 Oak Leaf Dr, Winona, MN 55987
0.14
$537,100
5
3.5
3,464
Off Market
255 Valley Oaks Dr, Winona, MN 55987
0.14
$424,600
4
3.5
2,793
Off Market

Local Information

  • Map ViewExplore the area around 229 Oak Leaf Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1987
0.45 acre lot
2,602 sqft
$184/sqft
3 Car Garage

About this House

Welcome Home! Located in popular Valley Oaks, this beautiful and special home offers a timeless and graceful design. This 4 bedroom home is warm, inviting and very spacious - offering perfect areas for family and activities, entertaining friends or to utilize as a private retreat. The outdoor space is exceptional - trek decks, garden areas, a perfect area for a fire pit and so much more. This stunning home is a must see!
229 Oak Leaf Dr, Winona, MN 55987 is a 4 bedroom, 4 bathroom, 2,602 sqft single-family home built in 1987. It last sold for the $429,000 asking price on Oct 3, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $477,600, with a rent estimate of $2,724/month.
Last check for updates: about 18 hours ago
Listed by Wendy Killen, (507) 458-8194
Keller Williams Premier Realty
Bought with: Jill Schmidt, (507) 458-7595, Edina Realty, Inc.
Source: NorthstarMLS as distributed by MLS GRID, MLS#6425421

Home Details for 229 Oak Leaf Dr

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Concrete,UnfinishedNumber of Rooms: 2Types of Rooms: Bathroom, Dining Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 1Number of Bathrooms (three quarters): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2602 Square FeetFoundation Area: 1600
Appliances & Utilities
Appliances: Cooktop, Dishwasher, Disposal, Dryer, Refrigerator, WasherDishwasherDisposalDryerLaundry: Laundry Room,Main Level,Sink,Washer HookupRefrigeratorWasher
Heating & Cooling
Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
No Fireplace
Gas & Electric
Electric: 200+ Amp Service, Power Company: Xcel EnergyGas: Natural Gas
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: None
View
No View

Exterior Features

Exterior Home Features
Roof: Age 8 Years Or Less AsphaltPatio / Porch: Composite Decking, PorchFencing: NoneNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Attached,Concrete,Floor Drain,Garage Door Opener,Insulated Garage
Pool
Pool: None
Frontage
Road Frontage: No Outlet/Dead End, TownshipRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: City Sewer/Connected
Surface & Elevation
Topography: Gently Rolling, Sloped, Wooded
Finished Area
Finished Area (above surface): 2602 Square Feet

Days on Market

Cumulative Days on Market: 3

Property Information

Year Built
Year Built: 1987
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: FrameNot a New ConstructionNot Attached PropertyNo Additional Parcels
Property Information
Parcel Number: 325220460

Price & Status

Price
List Price: $429,000
Status Change & Dates
Off Market Date: Tue Aug 29 2023

Location

Direction & Address
City: WinonaCommunity: Valley Oaks 1st
School Information
High School District: Winona Area Public Schools

Building

Building Area
Building Area: 2602 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.45 acres

Offer

Contingencies: None

Miscellaneous

BasementMls Number: 6425421Above Grade Unfinished Area: 2602

Price and Tax history

DateEventPrice
Oct 3, 2023
Source: NorthstarMLS as distributed by MLS GRID #6425421
Sold
$430,000
Aug 29, 2023
Source: NorthstarMLS as distributed by MLS GRID #6425421
Pending
$429,000

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

Based on information submitted to the MLS GRID as of 2026-09-07 16:53:00 PDT. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information
By searching NorthstarMLS listings you agree to the NorthstarMLS End User License Agreement

Frequently asked questions about 229 Oak Leaf Dr

  • What is 229 Oak Leaf Dr estimated to be worth?
    Trulia's estimated value for 229 Oak Leaf Dr in Winona, MN is $477,600.
  • What is the price history for 229 Oak Leaf Dr?
    229 Oak Leaf Dr in Winona, MN last sold for $430,000 in October 2023.
  • 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 229 Oak Leaf Dr have air conditioning?
    Yes, 229 Oak Leaf Dr in Winona, MN has air conditioning.
  • Does 229 Oak Leaf Dr have laundry facilities?
    Yes, 229 Oak Leaf Dr in Winona, MN has in-unit laundry.

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