2385 Winesap Dr, Jackson, MO 63755
OFF MARKET

2385 Winesap Dr
Jackson, MO 63755

  • 2 Beds
  • 2 Baths
  • 2,678 sqft (on 0.27 acres)

$375,700

Trulia Estimate
as of May 29, 2026
Est. Refi. Payment $2,154/mo*
Refinance Your Home

$375,700

Trulia Estimate
as of May 29, 2026
Est. Refi. Payment $2,154/mo*
Refinance Your Home
2 Beds
2 Baths
2,678 sqft
(on 0.27 acres)

Local Information

Map showing home location
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Description

ATTENTION INVESTORS! Investment opportunity is knocking at your door. Located in Jackson, this brick and vinyl ranch style duplex has approximately 1250 square feet per unit. Each unit offers 2 bedrooms and 2 bathrooms. Also featuring a kitchen dining combination, including all kitchen appliances, wood laminate flooring in the living room, covered patio's, 2 car garages and all units are handicap accessible. This duplex is located just within walking distance to schools.Call Aaron today to schedule a personal tour.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 2385 Winesap Dr

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 10

Property Information

Year Built
Year Built: 2011
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Exterior Features

Exterior Home Features
Exterior: Other

Lot Information

Lot Area: 0.27 acres

Price History for 2385 Winesap Dr

DatePriceEventSource
05/28/2014--Sold
MARIS #76415
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Property Tax and Assessment

Year2024
Tax$2,373
Assessment$244,560
Home facts updated by county records

Comparable Sales for 2385 Winesap Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2418 Jonathan Dr, Jackson, MO
0.14
Single-Family Home
-
02/17/26
3
2
1,758
2445 York Dr, Jackson, MO
0.06
Single-Family Home
-
04/20/26
4
3
2,318
2519 Cortland Dr, Jackson, MO
0.26
Single-Family Home
-
08/26/25
3
2
2,844
2423 Oak St, Jackson, MO
0.17
Single-Family Home
-
03/31/26
3
3
3,160
420 Whetstone Way, Jackson, MO
0.26
Single-Family Home
-
07/31/25
3
2
1,788
453 Whetstone Way, Jackson, MO
0.23
Single-Family Home
-
09/05/25
4
3
3,160
781 N West Ln, Jackson, MO
0.37
Single-Family Home
-
04/30/26
3
2.5
2,084
757 N West Ln, Jackson, MO
0.35
Single-Family Home
-
10/09/25
3
3
1,922
420 Pioneer Orchard Rd, Jackson, MO
0.29
Single-Family Home
-
04/22/26
4
3
2,398
862 Aspen Dr, Jackson, MO
0.46
Single-Family Home
-
10/24/25
4
3
2,500

Nearby homes

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Assigned Schools

These are the assigned schools for 2385 Winesap Dr.
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 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 "
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  • 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 "
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  • 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. "
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  • 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
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  • 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. "
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  • 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."
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  • 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
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  • 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
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  • 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. "
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  • Dani M.
    "Great, safe family neighborhood. Jackson has wonderful schools and friendly people. Great town to raise a family in."
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    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."
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  • 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
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2385 Winesap Dr, Jackson, MO 63755 is a 2 bedroom, 2 bathroom, 2,678 sqft single-family home built in 2011. This property is not currently available for sale. 2385 Winesap Dr was last sold on May 28, 2014 for $229,000. The current Trulia Estimate for 2385 Winesap Dr is $375,700.