OFF MARKET

Off market oct 2023 for $825K

$918,915

•

—

sq ft

27258 Gilmore Ridge Dr, Winona, MN 55987

About this home

Welcome to this incredible 28.5 acre Winona Equestrian property that offers a lifestyle every Rider dreams of having! The charming 4 bedroom 2 bath home combines the timeless appeal of a classic farmhouse with modern additions, making it a perfect blend of history and comfort. Elegantly designed with a style that remains true to its country setting, the farmhouse itself boasts a warm and inviting atmosphere. The property comes fully horse-ready with a 7-stall barn and a second stable with 2-stalls. For the equestrian enthusiast, the 160 x 72 foot Brickl Brothers built Indoor Riding Arena is a dream come true, providing year around riding and training opportunities. There are a variety of grassy paddocks, pastures and fields to turn your horses out or to ride in as well. Whether you’re looking for a peaceful retreat to enjoy quality time with your horses or you want to pursue your equestrian dreams and organize events or offer boarding and training services, this property offers it all!

Single-familyProperty Type

1908Year Built

28.5 acresLot Size

Listed by Wendy Killen • Keller Williams Premier Realty

Redfin checked: 3 minutes ago

•Source:NORTHSTARMLS as Distributed by MLS Grid #6388418

Redfin Estimate

$918,915

$94K since sold in October 2023$10K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 147% higher than the average sale price ($372K) of 6 comparable homes.

SOLD AUG 20, 2026
$415,000
A
3 beds3 baths— sq ft
1613 Gilmore Valley Rd, Winona, MN 55987
SOLD JUL 10, 2026
$460,000
B
4 beds2 baths— sq ft
398 Pleasant Hill Dr, Winona, MN 55987
SOLD SEP 11, 2026
$330,000
C
3 beds2 baths— sq ft
1580 Gilmore Valley Rd, Winona, MN 55987
SOLD JUN 30, 2026
$370,000
D
3 beds2 baths— sq ft
389 Knopp Valley Dr, Winona, MN 55987
SOLD SEP 11, 2026
$395,000
E
4 beds3 baths— sq ft
1260 Wincrest Dr, Winona, MN 55987
SOLD AUG 3, 2026
$262,000
F
4 beds2 baths— sq ft
1775 Gilmore Ave, Winona, MN 55987

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Earn from this home

Rent

$3,226/mo

Redfin rental estimate

List your home for rent

Market trends in 55987, MN

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

99.9%

1.0% MoM

Median sale price

$280K

$11K MoM

Avg. days on market

19d

4 days MoM

Recently sold homes

116

8 MoM

New listings for sale

$425,000
10 beds2 baths4,072 sq ft
323 W Broadway St, Winona, MN 55987
$155,000
2 beds1 bath850 sq ft
269 Carimona St, Winona, MN 55987
VIDEO TOUR
$614,900
2 beds2 baths1,728 sq ft
424 Valley Oaks Dr, Winona, MN 55987
FOR SALE BY OWNER
$329,000
4 beds3 baths1,248 sq ft
531 Glenview Dr, Winona, MN 55987
COMING SOON
$219,900
3 beds2 baths1,316 sq ft
650 W 5th St, Winona, MN 55987
$199,900
3 beds3 baths1,400 sq ft
557 W Sanborn St, Winona, MN 55987
SHORT SALE
$144,900
3 beds2 baths2,173 sq ft
613 E 2nd St, Winona, MN 55987
$235,000
2 beds2 baths1,248 sq ft
807 W Mark St, Winona, MN 55987
COMING SOON
$299,000
3 beds2 baths2,426 sq ft
1553 Gilmore Valley Rd, Winona, MN 55987
OPEN TODAY, 3:30PM TO 6PM
$199,900
2 beds1 bath939 sq ft
1414F Mcnally Dr, Winona, MN 55987
See all

Provided by Redfin

Sale history for 27258 Gilmore Ridge Dr

Date

Event

Price

NORTHSTARMLS as Distributed by MLS Grid #6388418

Oct 12, 2023

Pending

—

Oct 11, 2023

Sold

$825,000

Jul 20, 2023

Contingent

—

Jun 26, 2023

Listed

$895,000

Jun 16, 2023

Coming Soon

$895,000

NORTHSTARMLS as Distributed by MLS Grid #5118660

Dec 11, 2018

Listing Removed

—

Aug 20, 2012

Sold

$381,000

Jun 6, 2012

Listed

$373,000

+25

NORTHSTARMLS as Distributed by MLS Grid #SEMN4038129

Jun 6, 2012

Listed

$373,000

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Tax history for 27258 Gilmore Ridge Dr

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

28.5 Acres

Year renovated

1985

Sq. Ft.

2,819

Year built

1908

Style

Single Family Residential

County

Winona County

APN

160001200

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 27, 2026.

Property details

Parking

Parking Information
Parking Features: Gravel
Carport Spaces: 0

Interior

Bedroom Information
# of Bedrooms: 4

Bathroom Information
# of Full Baths (Total): 1
# of Three Quarter Baths (Total): 1
Description: Main Floor 3/4 Bath,Upper Level Full Bath

Room 1 Information
Room Type: Kitchen
Room Dimensions: 27x11
Room Level: Main

Room 2 Information
Room Type: Informal Dining Room
Room Dimensions: 14x7.5
Room Level: Main

Room 3 Information
Room Type: Dining Room
Room Dimensions: 18x14.6
Room Level: Main

Room 4 Information
Room Type: Living Room
Room Dimensions: 19x14.6
Room Level: Main

Room 5 Information
Room Type: Bathroom
Room Dimensions: 16.2x6
Room Level: Main

Room 6 Information
Room Type: Mud Room
Room Dimensions: 14x8
Room Level: Main

Room 7 Information
Room Type: Bedroom 1
Room Dimensions: 14x12
Room Level: Upper

Room 8 Information
Room Type: Bedroom 2
Room Dimensions: 12.5x12.5
Room Level: Upper

Room 9 Information
Room Type: Bedroom 3
Room Dimensions: 18x12
Room Level: Upper

Room 10 Information
Room Type: Bedroom 4
Room Dimensions: 14x9
Room Level: Upper

Room 11 Information
Room Type: Bathroom
Room Dimensions: 9x9
Room Level: Upper

Basement Information
Has Basement
Basement Features: Full, Stone/Rock, Unfinished

Dining Room Information
Dining Room Features: Breakfast Bar,Breakfast Area,Separate/Formal Dining Room

Other Rooms Information
4 BR on One Level,Main Floor Laundry

Heating & Cooling
Heating Information: Forced Air
Cooling Information: Central Air

Interior Features
Room Type: Kitchen, Informal Dining Room, Dining Room, Living Room, Bathroom, Mud Room, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4
Appliances: Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Refrigerator, Wall Oven, Washer, Water Softener Owned

Exterior

Building Information
Construction Materials: Wood Siding
Foundation Area: 1,322
Roof: Age 8 Years or Less, Metal

Exterior Features
Patio Porch Type: Patio
Fencing: Full, Other, Partial, Wood

Pool Information
Pool Features: None

Farm Information
Farm Type: Horse

Property Information
Above Ground Total Sq. Ft.: 2,941
Below Ground Total Sq. Ft.: 1,322
FractionalOwnershipYN: No
Property Type: Residential
Property Sub Type: Single Family Residence
Property Sub Type Description: Acreage
Other Structures: Barn(s), Chicken Coop/Barn, Granary, Indoor Arena, Other, Pole Building, Stable(s)
Above Grade Finished Area: 2,941
Amenities: Ceiling Fan(s),Hardwood Floors,Kitchen Window,Natural Woodwork,Patio,Panoramic View,Washer/Dryer Hookup

Land Information
Soil Type: Clay

Lot Information
Lot Features: Suitable for Horses
Lot Size Area: 28.5
Lot Size Units: Acres
Lot Size Dimensions: Irregular
Road Frontage Type: Township, Unpaved Streets

Financial

Tax Information
Tax Annual Amount: $2,278
Tax Year: 2023
Tax With Assessments: $2,278

Lease / Rent Details
RentalLicense Y/N: No

Financial Information
Conventional

Utilities

Utility Information
Water Source: Private, Well
Electric: 200+ Amp Service
Sewer: Private Sewer
Fuel: Propane

Location

School Information
High School District: Winona Area Public Schools
School District Number: 861
School District Phone: 507-494-0861

Location Information
Directions: Highway 43 to Gilmore Valley Road. 3.1 miles on Gilmore Valley Road to Gilmore Ridge Drive. Right on Gilmore Ridge Drive. In .8 miles home will be on the right side of the road.
Map Coordinate: 999-A1
Topography: Gently Rolling

Public facts

Beds: 4
Baths: 2.0
Sq. Ft.: 2,819
Stories: 2.0
Lot Size: 28.5 acres
Style: Single Family Residential
Year Built: 1908
Year Renovated: 1985
County: Winona County
APN: 160001200

Home facts updated by county records on Aug 27, 2026

Other

Home Information
Living Area: 2941
Main Level Finished Area: 1619.0000
Building Area Total: 4263
Age Of Property: 117
Levels: Two

Around this home

Schools

Jefferson Elementary School

Public K-4 • Assigned • 5.0mi

4/10

Winona Middle School

Public 5-8 • Assigned • 6.4mi

3/10

Winona Senior High School

Public 9-12 • Assigned • 4.9mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

1/10 Heat Factor

7 days above 99° expected this year, 14 days in 30 years

2/10 Wind Factor

Minor risk of severe winds over next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Winona, MN • 55987

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.7 hours in June and 3.7 hours in December, which is comparable to the U.S. average for solar exposure.

9.7 hrs

3.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$873,000 – $1.06M

Sell confidently with a local market expert in Winona. 3 minutes to get started.

Nearby similar homes

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New listings for sale in 55987

$425,000

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Convenient location • Washer and dryer • Income potential

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Three-season porch • Replacement windows • Manageable yard

VIDEO TOUR

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Zero-entry access • Four-season sunroom • Covered front porch

FOR SALE BY OWNER

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Oversized patio door • Natural light • Finished basement

COMING SOON

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Fenced backyard • Oversized deck • 2 story garage

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3 beds3 baths1,400 sq ft

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SHORT SALE

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3 beds2 baths2,173 sq ft

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7,000 sq ft lot • 2 garage spots • Built 1880

$235,000

2 beds2 baths1,248 sq ft

807 W Mark St, Winona, MN 55987

Bonus rooms • Detached garage • 5,662 sq ft lot

COMING SOON

$299,000

3 beds2 baths2,426 sq ft

1553 Gilmore Valley Rd, Winona, MN 55987

Fully enclosed patio • Window-lined patio • 2.18 acre lot

Home values near 27258 Gilmore Ridge Dr

Data from public records.

Address	Redfin Estimate
26275 Gilmore Ridge Drive, Winona, MN 4 Beds \| 3 Baths \| - Sq. Ft.	$412,562
27316 Gilmore Ridge Drive, Winona, MN 3 Beds \| 2 Baths \| 1404 Sq. Ft.	$292,215

Address	Redfin Estimate
27157 Gilmore Ridge Drive, Winona, MN 4 Beds \| 1 Baths \| - Sq. Ft.	$389,503
27693 Gilmore Ridge Drive, Winona, MN 2 Beds \| 2 Baths \| 2032 Sq. Ft.	$374,417

Address	Redfin Estimate
27720 Gilmore Ridge Drive, Winona, MN 4 Beds \| 2 Baths \| 1666 Sq. Ft.	$428,135
25984 Gilmore Ridge Drive, Winona, MN 3 Beds \| 2 Baths \| 1592 Sq. Ft.	$361,259

Property information provided by NORTHSTARMLS as Distributed by MLS Grid when last listed in 2023. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 55987, MN

Sale history for 27258 Gilmore Ridge Dr

Tax history for 27258 Gilmore Ridge Dr

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 55987

Home values near 27258 Gilmore Ridge Dr

More real estate resources