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 5 Oldham Rd estimated to be worth?

Trulia's estimated value for 5 Oldham Rd in Winona, MS is $375,100 .

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 5 Oldham Rd?

The closest schools to 5 Oldham Rd 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 5 Oldham Rd?

The lot at 5 Oldham Rd in Winona, MS is about 30 acres .

OFF MARKET

$375,100

Trulia Estimate

4 Beds
3 Baths

5 Oldham Rd, Winona, MS 38967

Est. Refi. Payment $2,364/mo*

Refinance Your Home

Home Value

Trulia Estimate

$375K

Since last month

$27K (+7.9%)

Since last year

$49K (-11.4%)

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 +758% in the last 10 years

Month	Estimated value
2026
October 2026	$375K
September 2026	$348K
August 2026	$348K
July 2026	$309K
June 2026	$329K
May 2026	$378K
April 2026	$336K
March 2026	$316K
February 2026	$348K
January 2026	$364K
2025
December 2025	$357K
November 2025	$444K
October 2025	$378K
September 2025	$424K
August 2025	$387K
July 2025	$439K
June 2025	$353K
May 2025	$356K
April 2025	$410K
March 2025	$384K
February 2025	$339K
January 2025	$314K
2024
December 2024	$351K
November 2024	$393K
October 2024	$352K
September 2024	$338K
August 2024	$314K
July 2024	$293K
June 2024	$329K
May 2024	$291K
April 2024	$331K
March 2024	$313K
February 2024	$266K
January 2024	$266K
2023
December 2023	$273K
November 2023	$269K
October 2023	$305K
September 2023	$300K
August 2023	$341K
July 2023	$360K
June 2023	$260K
May 2023	$319K
April 2023	$309K
March 2023	$301K
February 2023	$292K
January 2023	$298K
2022
December 2022	$291K
November 2022	$289K
October 2022	$293K
September 2022	$290K
August 2022	$298K
July 2022	$306K
June 2022	$305K
May 2022	$304K
April 2022	$297K
March 2022	$288K
February 2022	$286K
January 2022	$267K
2021
December 2021	$291K
November 2021	$276K
October 2021	$275K
September 2021	$268K
August 2021	$261K
July 2021	$268K
June 2021	$268K
May 2021	$132K
April 2021	$132K
March 2021	$129K
February 2021	$131K
January 2021	$127K
2020
December 2020	$122K
2019
September 2019	$33K
August 2019	$34K
July 2019	$38K
June 2019	$37K
May 2019	$32K
April 2019	$32K
March 2019	$29K
February 2019	$35K
January 2019	$28K
2018
December 2018	$37K
November 2018	$37K
October 2018	$37K
September 2018	$37K
August 2018	$37K
July 2018	$37K
June 2018	$40K
May 2018	$39K
April 2018	$39K
March 2018	$36K
February 2018	$36K
January 2018	$36K
2017
December 2017	$38K
November 2017	$47K
October 2017	$57K
September 2017	$56K
August 2017	$56K
July 2017	$56K
June 2017	$56K
May 2017	$56K
April 2017	$54K
March 2017	$47K
February 2017	$55K
January 2017	$55K
2016
December 2016	$46K
November 2016	$55K
October 2016	$44K

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
414 Summit St, Winona, MS	3.80	Single-Family Home	-	11/06/25	5	3	3,870
805 Obryan Cir, Winona, MS	3.57	Single-Family Home	-	03/27/26	3	1	1,227
505 Whitehead Dr, Winona, MS	3.28	Single-Family Home	-	05/12/26	3	-	2,073
400 Oak Dr, Winona, MS	3.96	Single-Family Home	-	10/08/25	4	2	2,070
226 N Quitman St, Winona, MS	3.81	Single-Family Home	-	05/14/26	3	1	1,824
135 Fox Rd #A, Winona, MS	6.17	Single-Family Home	-	12/09/25	4	2	1,152
56 New Hope Road Ext, Winona, MS	6.20	Single-Family Home	-	10/24/25	3	1	1,349
1549 Highway 51, Winona, MS	6.44	Single-Family Home	-	12/26/25	3	2	1,833

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
746 Highway 407, Winona, MS 38967	0.33	$238,100	3	-	2,601	Off Market
659 Highway 407, Winona, MS 38967	0.36	$486,300	3	-	2,033	Off Market
789 Highway 407, Winona, MS 38967	0.37	-	2	-	1,333	Off Market
129 Oldham Rd, Winona, MS 38967	0.44	$432,300	Studio	-	1,216	Off Market
Oldham Rd, Winona, MS 38967	0.44	-	-	-	-	Off Market
821 Highway 407, Winona, MS 38967	0.45	-	3	-	1,063	Off Market
798 Highway 407, Winona, MS 38967	0.50	$259,900	3	-	2,041	Off Market
831 Highway 407, Winona, MS 38967	0.53	$106,400	3	-	1,146	Off Market
826 Highway 407, Winona, MS 38967	0.55	$95,800	2	-	957	Off Market
839 Highway 407, Winona, MS 38967	0.59	$123,700	3	-	1,673	Off Market
645 Highway 407, Winona, MS 38967	0.59	$190,900	3	-	1,684	Off Market
849 Highway 407, Winona, MS 38967	0.62	-	2	-	1,156	Off Market
860 Highway 407, Winona, MS 38967	0.66	$235,300	4	-	2,162	Off Market
881 Highway 407, Winona, MS 38967	0.66	-	3	-	1,597	Off Market
617 Highway 407, Winona, MS 38967	0.73	$226,800	3	-	2,434	Off Market
880 Highway 407, Winona, MS 38967	0.74	$359,000	3	-	2,988	Off Market
861 Highway 407, Winona, MS 38967	0.76	$184,000	3	2	2,184	Off Market
881 Highway 407, Winona, MS 38967	0.76	$183,400	3	-	2,043	Off Market
732 Scotland Rd, Winona, MS 38967	0.80	-	-	-	-	Off Market
760 Scotland Rd, Winona, MS 38967	0.81	$283,400	3	-	1,714	Off Market

Local Information

Map ViewExplore the area around 5 Oldham Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

30 acre lot

About this House

Extremely lavish, 4-5 bedroom, 3 full bath, western cedar sided home. Property offers 40x80 shop, 2+/- acre lake, 30 country acres, swimming pool, wood floors, huge deck and wrap-around porch. Conveniently located approximately 5 miles from I55. 10 acres, home and lake can be bought separate without shop for $279,900. Come see. Make offer!!!

5 Oldham Rd, Winona, MS 38967 is a 4 bedroom, 3 bathroom single-family home. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $375,100, with a rent estimate of $2,228/month.

Home Details for 5 Oldham Rd

Property Information
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 30.00 acres

Price and Tax history

Date	Event	Price
Feb 15, 2012 Source: Agent Provided	ListingRemoved	$369,900
Mar 20, 2009 Source: Agent Provided	Listed For Sale	$369,900

Additional Cost

Market trends in Winona

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

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

Frequently asked questions about 5 Oldham Rd

What is 5 Oldham Rd estimated to be worth?
Trulia's estimated value for 5 Oldham Rd in Winona, MS is $375,100.
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 5 Oldham Rd?
The closest schools to 5 Oldham Rd 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 5 Oldham Rd?
The lot at 5 Oldham Rd in Winona, MS is about 30 acres.

Apartments for Rent

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Off Market Homes Near 5 Oldham Rd

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SOLD
MAY 12, 2026
3 bd
2,073 sqft
505 Whitehead Dr,
Winona, MS 38967
OFF MARKET
Est. $253,700
5 bd
3 ba
3,870 sqft
414 Summit St,
Winona, MS 38967
Kyle Cravens, Cravens Properties, LLC, My State MLS
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Winona
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Homes for sale near 5 Oldham Rd

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1.4 ACRES
$374,900
3 bd
2.5 ba
2,304 sqft
711 Lynn Dr,
Winona, MS 38967
Heather Traub, Dave's Realty, My State MLS
0.38 ACRES
$340,000
3 bd
2 ba
2,100 sqft
11 Rolling Green Cir,
Winona, MS 38967
Powers Properties
0.47 ACRES
$374,500
4 bd
3 ba
3,445 sqft
412 Church St,
Winona, MS 38967
Kyle Cravens, Cravens Properties, LLC, My State MLS
NEW - 1 DAY AGO
0.39 ACRES
$121,000
3 bd
2 ba
1,756 sqft
501 Whitehead Dr,
Winona, MS 38967
TENHET REAL ESTATE
0.33 ACRES
$109,000
3 bd
1 ba
1,072 sqft
215 Pearl St,
Winona, MS 38967
Kyle Cravens, Cravens Properties, LLC, My State MLS
0.75 ACRES
$319,000
3 bd
3 ba
3,000 sqft
104 Church St,
Winona, MS 38967
Chris Reed, Coltmor Realty Co., My State MLS
0.52 ACRES
$275,000
3 bd
2 ba
2,600 sqft
106 Hampton St,
Winona, MS 38967
Kyle Cravens, Cravens Properties, LLC, My State MLS
0.33 ACRES
$225,000
3 bd
3.5 ba
2,400 sqft
206 Church St,
Winona, MS 38967
Kyle Cravens, Cravens Properties, LLC, My State MLS
3.41 ACRES
$305,000
3 bd
2 ba
2,388 sqft
13 Fisher Rd,
Winona, MS 38967
Frankie Thorpe, McCool Thorpe Real Estate, My State MLS
0.96 ACRES
$225,000
3 bd
2 ba
2,734 sqft
308 Jones St,
Winona, MS 38967
Kyle Cravens, Cravens Properties, LLC, My State MLS
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Winona
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