Do kids play outside in Winona, MS?

As of early 2026, 88% of users say kids play outside

Are yards well-kept in Winona, MS?

As of early 2026, 87% of users say yards are well-kept

Does Winona, MS show holiday spirit?

As of early 2026, 86% of users say there's holiday spirit

Is parking easy in Winona, MS?

As of early 2026, 85% of users say parking is easy

Is a car needed in Winona, MS?

As of early 2026, 83% of users say car is needed

Is Winona, MS dog-friendly?

As of early 2026, 75% of users say it's dog friendly

Are neighbors friendly in Winona, MS?

As of early 2026, 70% of users say neighbors are friendly

As of early 2026, 56% of users say it's quiet

Do residents of Winona, MS plan to stay at least 5 years?

As of early 2026, 50% of users say they plan to stay for at least 5 years

Is Winona, MS walkable to restaurants?

As of early 2026, 50% of users say it's walkable to restaurants

Does Winona, MS have sidewalks?

As of early 2026, 45% of users say there are sidewalks

Would people walk alone at night in Winona, MS?

As of early 2026, 44% of users say people would walk alone at night

Is there wildlife in Winona, MS?

As of early 2026, 38% of users say there's wildlife

Are there community events in Winona, MS?

As of early 2026, 35% of users say there are community events

Is Winona, MS walkable to grocery stores?

As of early 2026, 33% of users say it's walkable to grocery stores

Are the streets well-lit in Winona, MS?

As of early 2026, 20% of users say streets are well-lit

What is 99 Herring Loop estimated to be worth?

Trulia's estimated value for 99 Herring Loop in Winona, MS is $146,200 .

Is Winona a buyer's or seller's market?

Winona is currently a balanced market, based on recent for-sale activity.

What do residents say about Winona?

Residents describe Winona, MS as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Winona, MS .

What are the closest schools to 99 Herring Loop?

The closest schools to 99 Herring Loop in Winona, MS are Winona Elementary School (Pre-K, rated 5/10), Winona Secondary School (Middle/High, rated 4/10).

How big is the lot at 99 Herring Loop?

The lot at 99 Herring Loop in Winona, MS is about 13 acres .

Does 99 Herring Loop have a garage?

Yes, 99 Herring Loop in Winona, MS has a garage.

OFF MARKET

99 Herring Loop
Winona, MS 38967

3 Beds
2,134 sqft (on 13 acres)

$146,200

Trulia Estimate

as of Aug 14, 2026

$146,200

Trulia Estimate

as of Aug 14, 2026

3 Beds

2,134 sqft

(on 13 acres)

Home Value

Trulia Estimate

$146K

Since last month

$10K (+7.1%)

Since last year

$21K (+16.8%)

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 +297% in the last 10 years

Month	Estimated value
2026
August 2026	$149K
July 2026	$144K
June 2026	$139K
May 2026	$145K
April 2026	$184K
March 2026	$140K
February 2026	$136K
January 2026	$138K
2025
December 2025	$147K
November 2025	$146K
October 2025	$139K
September 2025	$128K
August 2025	$128K
April 2025	$182K
February 2025	$121K
January 2025	$178K
2022
August 2022	$140K
July 2022	$144K
May 2022	$150K
April 2022	$141K
March 2022	$128K
2019
September 2019	$42K
August 2019	$41K
July 2019	$38K
June 2019	$36K
May 2019	$28K
April 2019	$28K
March 2019	$28K
February 2019	$28K
January 2019	$28K
2018
December 2018	$27K
November 2018	$27K
October 2018	$27K
September 2018	$27K
August 2018	$27K
July 2018	$27K
June 2018	$27K
May 2018	$27K
April 2018	$27K
March 2018	$27K
February 2018	$26K
January 2018	$26K
2017
December 2017	$27K
November 2017	$29K
October 2017	$39K
September 2017	$39K
August 2017	$38K
July 2017	$38K
June 2017	$38K
May 2017	$38K
April 2017	$38K
March 2017	$38K
February 2017	$38K
January 2017	$38K
2016
December 2016	$38K
November 2016	$38K
October 2016	$38K
September 2016	$38K
August 2016	$38K

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
609 N Rutherford Dr, Kilmichael, MS	4.59	Single-Family Home	-	12/22/25	3	2	2,295
2864 Highway 407, Kilmichael, MS	5.71	Single-Family Home	-	04/02/26	3	1	2,444
505 Whitehead Dr, Winona, MS	6.93	Single-Family Home	-	05/12/26	3	-	2,073
115 Hampton St, Winona, MS	7.04	Single-Family Home	-	09/18/25	4	2	2,497
226 N Quitman St, Winona, MS	7.35	Single-Family Home	-	05/14/26	3	1	1,824
400 Oak Dr, Winona, MS	7.56	Single-Family Home	-	10/08/25	4	2	2,070
414 Summit St, Winona, MS	7.45	Single-Family Home	-	11/06/25	5	3	3,870
422 Speedway Ave, Winona, MS	7.73	Single-Family Home	-	10/02/25	3	2	1,596
805 Montgomery St, Winona, MS	7.93	Single-Family Home	-	09/10/25	3	2	1,561

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
172 Scotland Rd, Winona, MS 38967	4.02	$227,400	Studio	-	2,432	Off Market

Local Information

Map ViewExplore the area around 99 Herring Loop.

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1903

Lot Size

13 acres

Living Area

2,134 sqft

Price/Sqft

$69

Parking

Garage

About this House

This single-family home is located at 99 Herring Loop, Winona, MS. 99 Herring Loop is in Winona, MS and in ZIP code 38967. This property has 3 bedrooms and approximately 2,134 sqft of floor space. This property has a lot size of 13.00 acres and was built in 1903.

99 Herring Loop, Winona, MS 38967 is a 3 bedroom, 2,134 sqft single-family home built in 1903. It is currently off market. The Trulia Estimate is $146,200, with a rent estimate of $1,274/month.

Home Details for 99 Herring Loop

Interior Features
Interior Details BasementIn-law unitNumber of Rooms: 5
Levels, Entrance, & Accessibility Floors: Other, Hardwood

Exterior Features
Exterior Home Features Roof: Shake ShingleExterior: WoodFoundation Type: PiersPatio
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1903
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 13.00 acres

Price and Tax history

Year	Property tax	Tax assessment
2025	$1,121	$58,988

Home facts updated by county records

Market trends in Winona

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

3MoM

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Additional Cost

Around this home

Winona Elementary School
PK-6
Public
567 Students
Winona-Montgomery Consolidated
5/10
GreatSchools Rating
Parent Rating Average
This is the best school within 200 mile radius. I live the system and the teachers, they are willing to go beyond their duties to help and teach every child individually. They are great and I would recomend it to anyone.
Parent Review
14y ago
2 Reviews

View nearby schools on GreatSchools

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 Winona

At least 7 Trulia users voted on each feature.

88 % Say kids play outside
87 % Say yards are well-kept
86 % Say there's holiday spirit
85 % Say parking is easy
83 % Say car is needed
75 % Say it's dog friendly
70 % Say neighbors are friendly
56 % Say it's quiet
50 % Say they plan to stay for at least 5 years
50 % Say it's walkable to restaurants
45 % Say there are sidewalks
44 % Say people would walk alone at night
38 % Say there's wildlife
35 % Say there are community events
33 % Say it's walkable to grocery stores
20 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 99 Herring Loop

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16.8 ACRES
$604,900
4 bd
3 ba
3,571 sqft
1529 Lower Milligan Springs Rd,
Kilmichael, MS 39747
Southern Homes Real Estate
0.48 ACRES
$122,000
3 bd
2 ba
1,634 sqft
508 Ridge Rd,
Kilmichael, MS 39747
Coltmor Realty Co.
NEW - 2 DAYS AGO
FOR SALE BY OWNER
1 ACRE
$400,000
3 bd
2.5 ba
3,000 sqft
711 Lynn Dr,
Winona, MS 38967
1.25 ACRES
$127,000
2 bd
2 ba
903 Pine Dr,
Kilmichael, MS 39747
Cravens Properties, LLC
1.5 ACRES
$228,000
3 bd
2.5 ba
2,097 sqft
59 Redell Dr,
Winona, MS 38967
Cravens Properties, LLC
405.1 ACRES
$1,053,260
3 bd
2 ba
1,100 sqft
Symour Rd,
Kilmichael, MS 39747
0.3 ACRES
$119,000
3 bd
2 ba
1,315 sqft
302 Braswell Dr,
Winona, MS 38967
Cravens Properties, LLC
AUCTION
0.38 ACRES
Price Unknown
4 bd
2 ba
1,980 sqft
501 Whitehead Dr,
Winona, MS 38967
0.52 ACRES
$275,000
3 bd
2 ba
2,600 sqft
106 Hampton St,
Winona, MS 38967
Cravens Properties, LLC
0.33 ACRES
$225,000
3 bd
3.5 ba
2,400 sqft
206 Church St,
Winona, MS 38967
Cravens Properties, LLC
See more homes for sale in
Winona
Take a look

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Off Market Homes Near 99 Herring Loop

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Frequently asked questions about 99 Herring Loop

What is 99 Herring Loop estimated to be worth?
Trulia's estimated value for 99 Herring Loop in Winona, MS is $146,200.
Is Winona a buyer's or seller's market?
Winona is currently a balanced market, based on recent for-sale activity.
What do residents say about Winona?
Residents describe Winona, MS as well-kept, easy to park in, and dog-friendly. Most residents say you need a car. See recently sold homes in Winona, MS.
What are the closest schools to 99 Herring Loop?
The closest schools to 99 Herring Loop in Winona, MS are Winona Elementary School (Pre-K, rated 5/10), Winona Secondary School (Middle/High, rated 4/10).
How big is the lot at 99 Herring Loop?
The lot at 99 Herring Loop in Winona, MS is about 13 acres.
Does 99 Herring Loop have a garage?
Yes, 99 Herring Loop in Winona, MS has a garage.

99 Herring Loop
Winona, MS 38967

$146,200

$146,200