4433 Chesterville Rd, Tupelo, MS 38801
Property image
Property image
OFF MARKET

4433 Chesterville Rd
Tupelo, MS 38801

  • 4 Beds
  • 2.5 Baths
  • 2,674 sqft (on 1.40 acres)

$290,900

Trulia Estimate
as of Jul 6, 2026

$290,900

Trulia Estimate
as of Jul 6, 2026
4 Beds
2.5 Baths
2,674 sqft
(on 1.40 acres)

Local Information

  • Map ViewExplore the area around 4433 Chesterville Rd.
  • Schools3 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Renovated 4 bedroom 2 1/2 bath home in very desirable area of west Tupelo. Lots of large rooms in this home. Master bedroom has a separate sitting area or office space and a large walk-in closet. This home also has a separate garage/shop to the rear for storage or hobbies.
4433 Chesterville Rd, Tupelo, MS 38801 is a 4 bedroom, 3 bathroom, 2,674 sqft single-family home built in 1972. It is currently off market. The Trulia Estimate is $290,900, with a rent estimate of $2,056/month.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 4433 Chesterville Rd

Interior Features

Heating & Cooling
Heating: Other, OtherAir ConditioningCooling System: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: Wood, BrickFoundation Type: Slab
Parking & Garage
GarageParking: Carport, Garage Attached

Property Information

Year Built
Year Built: 1972
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 1.40 acres

Price History for 4433 Chesterville Rd

DatePriceEventSource
01/14/2021$209,000ListingRemovedNMMLS #20-2537
12/17/2020$209,000PriceChange
Agent Provided
10/27/2020$219,900PriceChange
Agent Provided
09/17/2020$229,000Listed For SaleAgent Provided
08/29/2018$174,900ListingRemovedAgent Provided
05/29/2018$174,900PriceChange
Agent Provided
05/08/2018$179,900Listed For SaleAgent Provided
11/27/2012$169,000ListingRemovedAgent Provided
01/04/2012$185,000Listed For SaleN/A

Market trends in Tupelo

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
191
15MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax$2,958
Assessment$145,050
Home facts updated by county records

Comparable Sales for 4433 Chesterville Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
342 Valley Vista Dr, Tupelo, MS
0.35
Single-Family Home
-
07/25/25
3
1
2,171
119 Prairie Cv, Tupelo, MS
1.73
Single-Family Home
-
03/27/26
3
2
2,100
194 River Run, Tupelo, MS
1.56
Unknown
$368,700
02/20/26
-
-
157 River Run Dr, Tupelo, MS
1.51
Single-Family Home
-
08/20/25
5
3
2,321
810 Holly Hill Dr, Tupelo, MS
1.27
Single-Family Home
-
05/01/26
3
2
1,514
4168 Lincoln Cir, Tupelo, MS
0.67
Single-Family Home
-
04/15/26
2
1,080
5119 Lackey Ln, Tupelo, MS
1.66
Single-Family Home
-
07/18/25
4
3
3,254
5989 Autumn Ave, Tupelo, MS
1.97
Unknown
$375,000
01/20/26
-
-
508 Maury Cir, Tupelo, MS
1.78
Single-Family Home
-
09/09/25
4
2
2,600
102 Brisage Ln, Tupelo, MS
2.14
Single-Family Home
-
12/18/25
3
2.5
1,800

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 4433 Chesterville 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 Tupelo

At least 224 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 84 % Say parking is easy

  • 82 % Say yards are well-kept

  • 78 % Say there's holiday spirit

  • 73 % Say kids play outside

  • 68 % Say it's dog friendly

  • 63 % Say it's quiet

  • 51 % Say people would walk alone at night

  • 50 % Say neighbors are friendly

  • 50 % Say they plan to stay for at least 5 years

  • 44 % Say streets are well-lit

  • 40 % Say there's wildlife

  • 28 % Say there are sidewalks

  • 27 % Say there are community events

  • 26 % Say it's walkable to restaurants

  • 26 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Sarah Jones
    "Everyone has a dog. Walking dogs all the time. Park in the neighborhood. Perfect place to walk a dog. Sidewalks everywhere."
    0
    Flag
  • Sarah Jones
    "It’s historic, everyone knows each other, great park, great elementary school, good combination of first time homebuyers, family homes and retirees; good mixture of different size homes. While a historic neighborhood most homes have been updated. Lots of churches in the neighborhood with two good neighborhood restaurants."
    0
    Flag
  • Bridgit Stone
    "Joyner is a wonderful area to own a home and have children. Schools are great and the neighborhood is safe. "
    0
    Flag
  • Sarah Jones
    "Short, by personally owned vehicle, little traffic, no construction, no toll roads, no interstate or highway "
    0
    Flag
  • Khiry Karriem
    "I have a pretty decent commute. Public transportation would be a great benefit to have ensuring I always have a means to work. "
    0
    Flag
  • James Brooks
    "I have lived in the neighborhood for three years now. Very quiet and very nice and well kept neighborhood "
    0
    Flag
  • James Brooks
    "Pool , tennis courts, pickle ball courts, and clubhouse We have quarterly HOA meetings and other parties throughout the year"
    0
    Flag
  • Shelly C.
    "Commuting being a local is pretty smooth. Lunch time at crosstown/downtown and out by the mall is congested often. The 2 main issues are 1) the crosstown train stopping and blocking all routes North, South, East, and West. 2) the scheduling of road construction is absolutely annoying."
    5
    Flag
  • Brandyhgn
    "I have lived here for 24 years, some neighbors are great and some not so much but I’m pretty sure that can be said about any neighborhood. The one thing I do not like is at most houses here in our neighborhood is you have to share a driveway so a lot of people park in the street. "
    34
    Flag
  • Monica K.
    "There are many great outdoor activities for kids and adults in the area and some great schools in the area also! "
    3
    Flag
  • Brandyhgn
    "They have good medical facilities also. I have been very happy with the school systems thus far. Ok shopping, not much culturally"
    5
    Flag
  • Iravagerocks
    "my neighborhood is close to work and it's really easy to get to the highway and stuff like that like yeah you know????????? I like tupelo pretty good because it's pretty nice unless there's a bunch of shots fired and stuff."
    4
    Flag
  • Jmattlav
    "traffic is pretty quick. McCullough is never backed up. the school lines are getting m really mmmmm?ji) "
    0
    Flag
  • Kelleacreely
    "Wonderful place to live!! Lots of activities for kids. We have a nice mall and lots of restaurants. Plus Elvis Presley was born here. "
    0
    Flag
  • Dmarie P.
    "Very short commute to work. Location is close to everything. Less than 10 minutes from everywhere in Tupelo "
    4
    Flag
  • Necole Q.
    "We have family movie nights in the summer, family camp outs, & most recently a city wide New Year’s party."
    6
    Flag
  • Hester
    "Each community is alike a family and most are acquainted with each other enough to be alert of strangers around any home or child in their area . Everyone feels a sense of friendship and responsibility to watch out for one another and to protect all children without any form of prejudice entering their hearts or minds."
    0
    Flag
  • Brandyhgn
    "I live in the Joyner neighborhood. The houses are all cottage style. They have little parades for 4th of July and a neighborhood wide carport sale. For the most part everyone is nice and friendly"
    8
    Flag
  • Brandyhgn
    "There is a good public school system with every most every sport and is public school is not for you then there is a wonderful private school."
    1
    Flag
  • Brianna M.
    "I drive my own personal vehicle. I have never used public transportation. Our local public transportation isn’t easily accessible."
    0
    Flag
  • Brownyonna21
    "The Fair the new restaurant how downtown looks real nice the different vibes the people the Elvis Presley home and music "
    2
    Flag
  • Alvisclay6
    "They would love to walk their dog because it is a friendly neighborhood!!! The neighborhood is wonderful to interact with people!!"
    1
    Flag
  • Becky W.
    "the neighbors watch out for your kids also so your children are safer. It's close to grocery stores,downtown,mall and the hospital."
    0
    Flag
  • Vpotts
    "There are great restaurants, live music and a coffeehouse within walking distance. Close to everything including the airport, and grocery stores, shopping etc. Lots of people walking dogs in the neighborhood! "
    1
    Flag
  • Elijah L.
    "Tupelo have good schools, my kids have improved academic and there getting better nothing like we're I used to live California. I feel my kids are safe and in a good southern environment. We have many attractions for kids and parent."
    0
    Flag
  • Mssgmarion
    "Nice neighborhood people here are really nice. It’s nice and clean. Love it here. Safe for your children "
    2
    Flag
  • Lakin D.
    "There are a lot of dogs here and I lot of lovely people. People walk there dogs all through the day, but there is not a lot of bathing. "
    0
    Flag
  • Mssgmarion
    "The people are friendly. It’s a nice quiet neighborhood. Yards are clean and well kept. I love it because you hv a park with playground and soccer football field and a basketball court. "
    2
    Flag
  • Lora4mask
    "This neighborhood is close to everything but I also have deer- Owls -rabbits and other animals around my house. "
    0
    Flag
  • Alvisclay6
    "The people are actually nice and will watch your house and make sure kids are secure when you are work "
    0
    Flag
  • Suchandra R.
    "Neighborhood is mostly full of families, and it is very quiet. It’s kind of far from the grocery stores and the mall, but it’s not terrible. There’s a Dollar General and Shell’s station around the corner if you need something stat."
    0
    Flag
  • Cvcsmith426
    "I’ve lived here 4 years. Safe, quiet, friendly. Close to town, but country feel. "
    0
    Flag
  • Kate R.
    "I grew up here. Houses have character. I enjoy the people. Has a park. Near a school. Walking distant from bar."
    2
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

24 pet-friendly rentals in Tupelo, MS

Explore by feature - Garage

9 rentals with a garage in Tupelo, MS

Explore by feature - Air Conditioning

28 rentals with air conditioning in Tupelo, MS

Explore by feature - Pool

6 rentals with a pool in Tupelo, MS

Explore by feature - Washer/dryer

22 rentals with a washer/dryer in Tupelo, MS

Explore by feature - Outdoor Space

8 rentals with an outdoor space in Tupelo, MS

Homes for sale near 4433 Chesterville Rd

Skip to last item
Skip to first item

Off Market Homes Near 4433 Chesterville Rd

Skip to last item
Skip to first item