2497 Winesap Dr, Jackson, MO 63755
OFF MARKET

$384,600

Trulia Estimate
  • Studio
  • 4 Baths
  • 2,400 sqft (on 2.44 acres)

2497 Winesap Dr, Jackson, MO 63755

Est. Refi. Payment $2,266/mo*
Refinance Your Home

Home Value

Trulia Estimate
$385K
Since last month
Decreased$1K (-0.3%)
Since last year
Decreased$7K (-1.8%)
Since last sale
Increased$139K (+56.6%)
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 +81% in the last 10 years
MonthEstimated value
2026
August 2026$384K
August 2026$382K
July 2026$385K
June 2026$394K
May 2026$391K
April 2026$394K
March 2026$392K
February 2026$383K
January 2026$370K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
2497/2499 Winesap Dr, Jackson, MO
0.01
Multi-Family Home
-
09/15/25
2
2
2,568
846 & 848 Aaron Dr, Jackson, MO
0.52
Multi-Family Home
-
06/26/26
4
4
3,220
616 Greensferry Rd, Jackson, MO
2.04
Multi-Family Home
-
12/23/25
4
3
2,613
429/431 Deerwood Dr W, Jackson, MO
2.22
Multi-Family Home
-
06/26/26
4
4
2,928
387/389 Deerwood Dr W, Jackson, MO
2.22
Multi-Family Home
-
06/26/26
5
5
2,884
386 W Deerwood Dr #386 & 388, Jackson, MO
2.26
Multi-Family Home
-
10/31/25
6
6
5,580
914 Old Cape Rd, Jackson, MO
2.24
Multi-Family Home
-
11/26/25
-
13,856
121-123 Autumn Leaf Dr, Cape Girardeau, MO
5.12
Multi-Family Home
-
09/10/25
8
6
5,326
157 Highland Hills Dr, Jackson, MO
6.35
Multi-Family Home
-
10/28/25
10
6
4,608
176 Highland Hills Dr, Jackson, MO
6.38
Multi-Family Home
-
11/10/25
10
6
4,608

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
2499 Winesap Dr, Jackson, MO 63755
0.01
-
-
-
-
Off Market
2497/2499 Winesap Dr, Jackson, MO 63755
0.01
$413,400
2
2
2,568
Off Market
2445 York Dr, Jackson, MO 63755
0.05
-
4
3
2,318
Recently Sold
256 Pioneer Orchard Rd, Jackson, MO 63755
0.07
$394,800
3
3
2,951
Off Market
2444 York Dr, Jackson, MO 63755
0.08
$336,800
4
3
2,314
Off Market
2313 Winesap Dr, Jackson, MO 63755
0.12
$369,900
4
4
2,566
Off Market
Address Not Disclosed, Jackson, MO 63755
0.14
$58,400
-
-
-
Off Market
2504 Jonathan Dr, Jackson, MO 63755
0.14
$353,700
3
3
2,500
Off Market
2418 Jonathan Dr, Jackson, MO 63755
0.14
-
3
2
1,758
Recently Sold
2248 York Dr, Jackson, MO 63755
0.15
$314,800
3
2
1,575
Off Market
2344 Jonathan Dr, Jackson, MO 63755
0.16
$269,600
3
2
1,479
Off Market
2423 Oak St, Jackson, MO 63755
0.16
-
3
3
3,160
Recently Sold

Local Information

  • Map ViewExplore the area around 2497 Winesap Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Multi-Family
Built in 2014
2.44 acre lot
2,400 sqft
$160/sqft
Garage

About this House

Attention Investors - Brick Faced, Vinyl Sided, Duplex on Slab with Separate Meters completed late 2014, located on Corner Lot in Pioneer Orchard Second Subdivision. Each Side is 2BR, 2BA, 2-Car Garage, Total Electric, ML Laundry, Open Concept, Kitchen with Stainless Steel Appliances, Back Patio. Orchard Elementary, Jackson R2. Each Tenants pay their own utilities. 2497 will be vacant until 4/18 then available for rent. Lot Size 106x186.
2497 Winesap Dr, Jackson, MO 63755 is a studio, 4 bathroom, 2,400 sqft multi-family built in 2014. It last sold for $245,000 on Apr 22, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $384,600, with a rent estimate of $1,489/month.

Home Details for 2497 Winesap Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Number of Rooms: 10Ceiling Fan

Property Information

Year Built
Year Built: 2014
Property Type / Style
Property Type: Multi FamilyArchitecture: duplex single

Exterior Features

Exterior Home Features
Exterior: StoneFoundation Type: SlabPatio
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 2

Lot Information

Lot Area: 2.44 acres

Price and Tax history

DateEventPrice
Apr 22, 2016
Source: MARIS #84213
Sold
--

Market trends in Jackson

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$273K
$5.5KMoM
Sale-to-List Price
100.0%
0.4%MoM
Price per sq ft
$147
$2MoM
Available listings
103
12MoM

Around this home

What Locals Say about Jackson

At least 105 Trulia users voted on each feature.

  • 94 % Say parking is easy

  • 91 % Say car is needed

  • 86 % Say it's dog friendly

  • 85 % Say yards are well-kept

  • 82 % Say kids play outside

  • 79 % Say there's holiday spirit

  • 76 % Say people would walk alone at night

  • 65 % Say it's quiet

  • 60 % Say neighbors are friendly

  • 57 % Say streets are well-lit

  • 49 % Say they plan to stay for at least 5 years

  • 47 % Say there are sidewalks

  • 46 % Say there's wildlife

  • 23 % Say it's walkable to grocery stores

  • 23 % Say there are community events

  • 20 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Nurselady8
    "Not bad I actually live in Columbia now and always felt safe when I lived in Jackson would never live in Cape at least it wouldn’t be my first Choice. Love Jackson. Beautiful parks close to shopping without actually having to go into Cape very far. Lives in Jackson for 10 years then moved to Columbia "
    0
    Flag
  • DGossett
    "The district hosts many events throughout the year including concerts, farmers markets, homecomers, and Oktoberfest to name a few."
    1
    Flag
  • Kaitlyn S.
    "Good school district, good parks, clean and friendly people. A nice small town with everything in a relatively close location. "
    1
    Flag
  • Drake G. .
    "There are community events that help the more less fortunate in our town along with events where everyone used to get together and read/trade books, set up rides for the town and concession stands, and get together to just celebrate each other as a whole"
    0
    Flag
  • Brian H.
    "Plenty of grass for dogs to play in, but sometimes dogs can be easily distracted by neighbors or other animals "
    0
    Flag
  • Edasher06
    "Yearly neighborhood garage sale in April, lot of dog walking. Very quiet. Most kids are older, high school to college, but there are a handful of younger as well. very close to elementary school without traffic. when the wind is right you can hear them on the playground. "
    0
    Flag
  • Drake G. .
    "A big get together in the middle of town where kids get to read/exchange books and have a speaker read to them"
    0
    Flag
  • David G.
    "Annwood Estates is a wonderful place to live, neighbors are all great people. We have lived in Jackson for 6 years and would highly recommend this town for a family moving. "
    0
    Flag
  • Drake G. .
    "They would like the fenced in backyards and along with the low traffic and quite area. I think that they would also enjoy the acceptance of others."
    0
    Flag
  • Drake G
    "The schools are decent but I wouldn’t recommend enrolling your child there. Most teachers and counselors aren’t reliable "
    1
    Flag
  • Krysten E.
    "have lived here my whole life. It is a very nice to raise a family. The schools here are great! nice community "
    0
    Flag
  • Ted J.
    "I work from home, so not much of a commute. I do have an office in Cape Girardeau which takes me 23 minutes to get too. Ain’t nobody got time for that!"
    0
    Flag
  • Tbruend
    "I see plenty of people out walking their dogs around the neighborhood and the parks. You're welcome to join the walk too "
    0
    Flag
  • Shawn C.
    "its great for commute to anywhere from here. Interstate is close and you are right in between Memphis and St Louis. it is also near the port authority of Southeast Missouri. "
    0
    Flag
  • Bethcreasy369
    "we dont do anything for any holiday. neighbors dont talk. I dont even know my neighbors name. no one talks to each other unless they already know each other. "
    0
    Flag
  • Beargibson3100
    "nothing beats the parade of entitled parents who won't let their kids ride the bus. traffic is horrendous between 7:30 and 8 am. also people like to race up and down this street. i won't let my 5 year old play outside because of the traffic. "
    0
    Flag
  • Dani M.
    "Great, safe family neighborhood. Jackson has wonderful schools and friendly people. Great town to raise a family in."
    0
    Flag
  • Nancy L.
    "My neighborhood just started a website, I haven't been on just yet but I will soon. They have allot of things for children to do, but it doesn't have anything for singles, or for adults over 55 without children."
    0
    Flag
  • Jake S. K.
    "Lived in Jackson for years, very homey. Everything you need is here, but just a short drive to Cape. Small town outside of the busy “city”. Good schools. The movie type of neighborhoods for the most part."
    0
    Flag
  • Julie S.
    "Busy neighborhood seems to be right on top of each other cars fly up and down the street even though I love for my kid to play outside I do not always feel very safe I do love being able to see the deer in the back yard but It’s very difficult to get to the interstate"
    2
    Flag
  • Angela W.
    "I've lived in this neighborhood for two years. The neighbors are friendly, there are a lot of events, and it is just a few minutes out from any store or restaurant you need or want."
    0
    Flag
  • Kelly A. N.
    "Jackson is the most beautiful city in Missouri. I love the people and the beautiful homes. the schools are hands down the best in the area. "
    1
    Flag
  • Rebeka K. M.
    "I've lived in my neighborhood for 4 months. I like this neighborhood because it is peaceful. the neighbors are kind and respectful. I know that my kids are safe to play outside in this neighborhood."
    1
    Flag
  • Ktabvintage
    "It's very difficult to get in and out of traffic without taking an alternate route during school let out. There are no sidewalks in the subdivision. Somewhat concerned about the Karst with many of the homes having foundation issues."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 2497 Winesap Dr

  • What is 2497 Winesap Dr estimated to be worth?
    Trulia's estimated value for 2497 Winesap Dr in Jackson, MO is $384,600.
  • What is the price history for 2497 Winesap Dr?
    2497 Winesap Dr in Jackson, MO last sold in April 2016.
  • Is Jackson a buyer's or seller's market?
    Jackson is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Jackson?
    The median sale price in Jackson is $273K. That is up $5.5K from the prior month.
  • Does 2497 Winesap Dr have air conditioning?
    Yes, 2497 Winesap Dr in Jackson, MO has air conditioning.

Explore by feature - Pet Friendly

25 pet-friendly rentals in Jackson, MO

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Off Market Homes Near 2497 Winesap Dr

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