Is parking easy in Ackerman, MS?

As of early 2026, 100% of users say parking is easy

Do kids play outside in Ackerman, MS?

As of early 2026, 100% of users say kids play outside

Are yards well-kept in Ackerman, MS?

As of early 2026, 100% of users say yards are well-kept

Would people walk alone at night in Ackerman, MS?

As of early 2026, 86% of users say people would walk alone at night

Is Ackerman, MS quiet?

As of early 2026, 80% of users say it's quiet

Does Ackerman, MS show holiday spirit?

As of early 2026, 75% of users say there's holiday spirit

Is Ackerman, MS walkable to restaurants?

As of early 2026, 75% of users say it's walkable to restaurants

Are the streets well-lit in Ackerman, MS?

As of early 2026, 71% of users say streets are well-lit

Are neighbors friendly in Ackerman, MS?

As of early 2026, 62% of users say neighbors are friendly

Is Ackerman, MS dog-friendly?

As of early 2026, 60% of users say it's dog friendly

Is a car needed in Ackerman, MS?

As of early 2026, 50% of users say car is needed

Do residents of Ackerman, 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 there wildlife in Ackerman, MS?

As of early 2026, 40% of users say there's wildlife

Is Ackerman, MS walkable to grocery stores?

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

Does Ackerman, MS have sidewalks?

As of early 2026, 29% of users say there are sidewalks

What is 299 Chester St estimated to be worth?

Trulia's estimated value for 299 Chester St in Ackerman, MS is $271,000 .

What is the price history for 299 Chester St?

299 Chester St in Ackerman, MS last sold in May 2015.

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

Ackerman is currently a buyer's market, based on recent for-sale activity.

What are the closest schools to 299 Chester St?

The closest schools to 299 Chester St in Ackerman, MS are Ackerman Elementary School (Pre-K, rated 10/10), Ackerman High School (Middle, rated 5/10).

Does 299 Chester St have laundry facilities?

Yes, 299 Chester St in Ackerman, MS has laundry facilities.

How big is the lot at 299 Chester St?

The lot at 299 Chester St in Ackerman, MS is about 2.1 acres .

OFF MARKET

$271,000

Trulia Estimate

3 Beds
3 Baths
2,418 sqft (on 2.10 acres)

299 Chester St, Ackerman, MS 39735

Refinance Your Home

Home Value

Trulia Estimate

$271K

Since last month

$800 (+0.3%)

Since last year

$5K (+2%)

Since last sale

$97K (+55.3%)

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 +49% in the last 10 years

Month	Estimated value
2026
August 2026	$272K
August 2026	$271K
July 2026	$271K
June 2026	$271K
May 2026	$266K
April 2026	$258K
March 2026	$253K
February 2026	$243K
January 2026	$245K
2025
December 2025	$258K
November 2025	$263K
October 2025	$266K
September 2025	$261K
August 2025	$266K
July 2025	$274K
June 2025	$271K
May 2025	$274K
April 2025	$272K
March 2025	$264K
February 2025	$274K
January 2025	$275K
2024
December 2024	$276K
November 2024	$278K
October 2024	$265K
September 2024	$260K
August 2024	$254K
July 2024	$252K
June 2024	$252K
May 2024	$254K
April 2024	$256K
March 2024	$252K
February 2024	$249K
January 2024	$246K
2023
December 2023	$252K
November 2023	$243K
October 2023	$249K
September 2023	$246K
August 2023	$253K
July 2023	$252K
June 2023	$259K
May 2023	$247K
April 2023	$243K
March 2023	$240K
February 2023	$227K
January 2023	$223K
2022
December 2022	$225K
November 2022	$229K
October 2022	$231K
September 2022	$231K
August 2022	$229K
July 2022	$229K
June 2022	$229K
May 2022	$225K
April 2022	$227K
March 2022	$227K
February 2022	$222K
January 2022	$220K
2021
December 2021	$219K
November 2021	$215K
October 2021	$214K
September 2021	$210K
August 2021	$209K
July 2021	$208K
June 2021	$178K
May 2021	$141K
April 2021	$136K
March 2021	$140K
February 2021	$137K
January 2021	$122K
2020
December 2020	$120K
November 2020	$119K
October 2020	$120K
September 2020	$110K
August 2020	$125K
July 2020	$125K
June 2020	$126K
May 2020	$129K
April 2020	$136K
March 2020	$155K
February 2020	$175K
January 2020	$174K
2019
December 2019	$168K
November 2019	$165K
October 2019	$166K
September 2019	$174K
August 2019	$168K
July 2019	$170K
June 2019	$155K
May 2019	$174K
April 2019	$175K
March 2019	$180K
February 2019	$169K
January 2019	$161K
2018
December 2018	$154K
November 2018	$149K
October 2018	$162K
September 2018	$167K
August 2018	$162K
July 2018	$161K
June 2018	$172K
May 2018	$182K
April 2018	$190K
March 2018	$190K
February 2018	$189K
January 2018	$188K
2017
December 2017	$188K
November 2017	$187K
October 2017	$187K
September 2017	$186K
August 2017	$186K
July 2017	$186K
June 2017	$185K
May 2017	$185K
April 2017	$185K
March 2017	$184K
February 2017	$184K
January 2017	$184K
2016
December 2016	$183K
November 2016	$183K
October 2016	$182K

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
16 Busby St, Ackerman, MS	0.99	Single-Family Home	-	09/03/25	3	-	1,656

Home facts updated by county records

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
46-100 W Center St, Ackerman, MS 39735	0.24	$875,000	Studio	-	1,000	For Sale
State Highway 12, Ackerman, MS 39735	0.36	$649,799	-	-	-	For Sale
168 Gaston St, Ackerman, MS 39735	0.39	$235,000	3	2	1,584	For Sale
156 E Church St, Ackerman, MS 39735	0.45	$170,000	3	2	1,900	For Sale
261 Sides Ave, Ackerman, MS 39735	0.85	$25,000	-	-	-	For Sale
546 Sides Ave, Ackerman, MS 39735	1.02	$185,000	3	2	1,261	For Sale
7844 State Highway 12, Ackerman, MS 39735	1.04	-	-	-	-	Off Market
7840 State Highway 12, Ackerman, MS 39735	1.07	$585,000	4	3.5	3,793	For Sale

Local Information

Map ViewExplore the area around 299 Chester St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1880

Lot Size

2.1 acres

Living Area

2,418 sqft

Price/Sqft

$112

About this House

An Historic staple in Ackerman, rich in character and charm. This home is gorgeous! From the moment you step into the grand foyer, you will feel at home. Beautifully renovated while maintaining its historic integrity. On top of being a southern charmer, this home is energy efficient. From the high ceilings, to the hardwood floors, you must see this home to appreciate the detail. Incredible gourmet kitchen, office, sunroom, 3 bedrooms, and 2.5 baths. There is a large area upstairs which is floored however currently unfinished and not included with square footage. All situated on 2 acres!

299 Chester St, Ackerman, MS 39735 is a 3 bedroom, 3 bathroom, 2,418 sqft single-family home built in 1880. It last sold for $175,000 on May 8, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $271,000, with a rent estimate of $1,603/month.

Home Details for 299 Chester St

Interior Features
Levels, Entrance, & Accessibility Stories: 2Floors: Hardwood
Interior Details Number of Rooms: 6Types of Rooms: Walk In Closet, Breakfast Nook, Family Room, Laundry Room, Office, Workshop, Sun Room
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: MetalExterior: WoodFoundation Type: Piers
Parking & Garage Parking Space: 1Parking: Carport

Property Information
Year Built Year Built: 1880
Property Type / Style Property Type: Single Family HomeArchitecture: Queen Anne / Victorian

Lot Information
Lot Area: 2.10 acres

Price and Tax history

Date	Event	Price
May 8, 2015 Source: N/A	Sold	--
Dec 6, 2014 Source: Agent Provided	ListingRemoved	$199,900
Aug 10, 2014 Source: Agent Provided	PriceChange	$199,900 Price decreased by 16%
Jun 6, 2014 Source: Agent Provided	Listed For Sale	$239,000

Year	Property tax	Tax assessment
2025	$1,543	$137,245

Additional Cost

Market trends in Ackerman

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

Around this home

Ackerman Elementary School
PK-6
Public
462 Students
Choctaw Co School Dist
10/10
GreatSchools Rating
Parent Rating Average
AES is a wonderful school for any Elemenary school student. We are now on our 4th child that is attending/has attended AES and we Love it. Hometown feel, teachers that truly care and still have strong Christian values. Would recommend to anyone.
Parent Review
8y ago
6 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 Ackerman

At least 3 Trulia users voted on each feature.

100 % Say parking is easy
100 % Say kids play outside
100 % Say yards are well-kept
86 % Say people would walk alone at night
80 % Say it's quiet
75 % Say there's holiday spirit
75 % Say it's walkable to restaurants
71 % Say streets are well-lit
62 % Say neighbors are friendly
60 % Say it's dog friendly
50 % Say car is needed
50 % Say they plan to stay for at least 5 years
40 % Say there's wildlife
33 % Say it's walkable to grocery stores
29 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Frequently asked questions about 299 Chester St

What is 299 Chester St estimated to be worth?
Trulia's estimated value for 299 Chester St in Ackerman, MS is $271,000.
What is the price history for 299 Chester St?
299 Chester St in Ackerman, MS last sold in May 2015.
Is Ackerman a buyer's or seller's market?
Ackerman is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 299 Chester St?
The closest schools to 299 Chester St in Ackerman, MS are Ackerman Elementary School (Pre-K, rated 10/10), Ackerman High School (Middle, rated 5/10).
Does 299 Chester St have laundry facilities?
Yes, 299 Chester St in Ackerman, MS has laundry facilities.
How big is the lot at 299 Chester St?
The lot at 299 Chester St in Ackerman, MS is about 2.1 acres.