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 $354,700 .

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

Winona is currently a buyer's 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

5 Oldham Rd
Winona, MS 38967

4 Beds
3 Baths

$354,700

Trulia Estimate

as of Aug 11, 2026

Est. Refi. Payment $2,089/mo*

Refinance Your Home

$354,700

Trulia Estimate

as of Aug 11, 2026

Est. Refi. Payment $2,089/mo*

Refinance Your Home

4 Beds

3 Baths

(on 30 acres)

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

Property Type

Single-Family Home

Lot Size

30 acres

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. It is currently off market. The Trulia Estimate is $354,700, with a rent estimate of $2,184/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 History for 5 Oldham Rd

Date	Price	Event	Source
02/15/2012	$369,900	ListingRemoved	Agent Provided

03/20/2009	$369,900	Listed For Sale	Agent Provided

Market trends in Winona

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

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Comparable Sales for 5 Oldham Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
115 Hampton St, Winona, MS	3.50	Single-Family Home	-	09/18/25	4	2	2,497
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
422 Speedway Ave, Winona, MS	4.18	Single-Family Home	-	10/02/25	3	2	1,596
805 Montgomery St, Winona, MS	4.42	Single-Family Home	-	09/10/25	3	2	1,561
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

Nearby homes

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Additional Cost

Assigned Schools

These are the assigned schools for 5 Oldham Rd.

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 5 Oldham Rd

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NEW - 32 MIN AGO
FOR SALE BY OWNER
1 ACRE
$400,000
3 bd
2.5 ba
3,000 sqft
711 Lynn Dr,
Winona, MS 38967
1.5 ACRES
$228,000
3 bd
2.5 ba
2,097 sqft
59 Redell Dr,
Winona, MS 38967
Cravens Properties, LLC
0.38 ACRES
$340,000
3 bd
2 ba
2,100 sqft
11 Rolling Green Cir,
Winona, MS 38967
Powers Properties
AUCTION
0.38 ACRES
Price Unknown
4 bd
2 ba
1,980 sqft
501 Whitehead Dr,
Winona, MS 38967
0.3 ACRES
$119,000
3 bd
2 ba
1,315 sqft
302 Braswell Dr,
Winona, MS 38967
Cravens Properties, LLC
0.75 ACRES
$319,000
3 bd
3 ba
3,000 sqft
104 Church St,
Winona, MS 38967
Coltmor Realty Co.
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
NEW - 21 HRS AGO
3.41 ACRES
$305,000
3 bd
2 ba
2,388 sqft
13 Fisher Rd,
Winona, MS 38967
McCool Thorpe Real Estate
0.96 ACRES
$225,000
3 bd
2 ba
2,734 sqft
308 Jones 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 5 Oldham Rd

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SOLD
MAY 12, 2026
3 bd
2,073 sqft
505 Whitehead Dr,
Winona, MS 38967
SOLD
NOV 6, 2025
5 bd
3 ba
3,870 sqft
414 Summit St,
Winona, MS 38967
Cravens Properties, LLC
See more homes for sale in
Winona
Take a look

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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 $354,700.
Is Winona a buyer's or seller's market?
Winona is currently a buyer's 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.

5 Oldham Rd
Winona, MS 38967

$354,700

$354,700