Is parking easy in Jackson, KY?

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

Is a car needed in Jackson, KY?

As of early 2026, 83% of users say car is needed

Do residents of Jackson, KY plan to stay at least 5 years?

As of early 2026, 83% of users say they plan to stay for at least 5 years

Is Jackson, KY quiet?

As of early 2026, 83% of users say it's quiet

Are yards well-kept in Jackson, KY?

As of early 2026, 80% of users say yards are well-kept

Do kids play outside in Jackson, KY?

As of early 2026, 75% of users say kids play outside

Would people walk alone at night in Jackson, KY?

As of early 2026, 75% of users say people would walk alone at night

Does Jackson, KY show holiday spirit?

As of early 2026, 71% of users say there's holiday spirit

Are neighbors friendly in Jackson, KY?

As of early 2026, 69% of users say neighbors are friendly

Is Jackson, KY dog-friendly?

As of early 2026, 67% of users say it's dog friendly

Is there wildlife in Jackson, KY?

As of early 2026, 67% of users say there's wildlife

Is Jackson, KY walkable to grocery stores?

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

Are the streets well-lit in Jackson, KY?

As of early 2026, 20% of users say streets are well-lit

Is Jackson, KY walkable to restaurants?

As of early 2026, 14% of users say it's walkable to restaurants

OFF MARKET

27 Chestnut Dr
Jackson, KY 41339

Studio
298 sqft (on 0.75 acres)

$253,400

Trulia Estimate

as of Jul 29, 2026

Est. Refi. Payment $1,557/mo*

Refinance Your Home

$253,400

Trulia Estimate

as of Jul 29, 2026

Est. Refi. Payment $1,557/mo*

Refinance Your Home

Studio

298 sqft

(on 0.75 acres)

Local Information

Map ViewExplore the area around 27 Chestnut Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

2001

Lot Size

0.75 acres

Living Area

298 sqft

Price/Sqft

$850

About this House

This single-family home is located at 27 Chestnut Dr, Jackson, KY. 27 Chestnut Dr is in Jackson, KY and in ZIP code 41339. This property has approximately 298 sqft of floor space. This property has a lot size of 0.75 acres and was built in 2001.

27 Chestnut Dr, Jackson, KY 41339 is a studio, 298 sqft single-family home built in 2001. It last sold for $198,000 on Jun 24, 2022. It is currently off market. The Trulia Estimate is $253,400, with a rent estimate of $986/month.

Home Details for 27 Chestnut Dr

Interior Features
Levels, Entrance, & Accessibility Stories: 2

Property Information
Year Built Year Built: 2001
Property Type / Style Property Type: Single Family Home

Exterior Features
Exterior Home Features Exterior: OtherFoundation Type: Concrete Block

Lot Information
Lot Area: 0.75 acres

Price History for 27 Chestnut Dr

Date	Price	Event	Source
06/24/2022	$198,000	Sold	N/A
Recording Date 06/24/2022 Contract Date 10/21/2021 County Transfer Tax N/A Total Transfer Tax $198
10/21/2021	$198,000	Sold	Imagine MLS #20103200
Recording Date 10/21/2021 County Transfer Tax N/A Total Transfer Tax N/A
07/25/2021	$215,000	Pending	Imagine MLS #20103200

02/25/2021	$215,000	Listed For Sale	Imagine MLS #20103200

04/09/2014	$230,000	Sold	N/A
Recording Date 04/09/2014 Contract Date 04/04/2014 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Jackson

Last updated June 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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Property Tax and Assessment

Year	2024
Tax	$2,843
Assessment	$198,000

Home facts updated by county records

Comparable Sales for 27 Chestnut Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
131 Summer Ridge Dr, Jackson, KY	1.09	Single-Family Home	$255,000	01/12/26		-	1,800
93 Collier Ave, Jackson, KY	2.10	Single-Family Home	$240,000	11/24/25	3	2.5	2,754
966 Highland Ave, Jackson, KY	2.28	Single-Family Home	$210,000	07/15/26	4	3.5	3,400
2514 Smith Ln, Jackson, KY	1.94	Single-Family Home	$120,000	03/10/26	2	1	1,000
226 Sycamore St, Jackson, KY	1.86	Single-Family Home	$25,000	05/11/26	4	1	2,198
112 River St, Jackson, KY	1.81	Single-Family Home	$60,000	02/10/26	3	1	1,260
76 State Dr, Jackson, KY	2.34	Single-Family Home	$250,000	07/31/25	3	2	3,576
2101 Town Hill Rd, Jackson, KY	1.98	Single-Family Home	$108,800	05/15/26	4	1	3,000
1513 Hargis Ln, Jackson, KY	1.92	Single-Family Home	$21,000	06/16/26	3	1	3,396
834 Miller Branch Barwick Rd, Jackson, KY	2.28	Single-Family Home	$5,000	12/19/25		-	980

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $345,400
4 bd
3 ba
3,796 sqft
293 Oakwood Dr,
Jackson, KY 41339
Keller Williams Legacy Group, Imagine MLS
OFF MARKET
Est. $199,300
4 bd
2 ba
2,000 sqft
105 Privett Ln,
Jackson, KY 41339
Trifecta Real Estate Experts, Imagine MLS
OFF MARKET
Est. $101,700
3 bd
1 ba
1,280 sqft
389 Beattyville Rd,
Jackson, KY 41339
Stamper Real Estate Group, Imagine MLS

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Additional Cost

Assigned Schools

These are the assigned schools for 27 Chestnut 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 3 Trulia users voted on each feature.

100 % Say parking is easy
83 % Say car is needed
83 % Say they plan to stay for at least 5 years
83 % Say it's quiet
80 % Say yards are well-kept
75 % Say kids play outside
75 % Say people would walk alone at night
71 % Say there's holiday spirit
69 % Say neighbors are friendly
67 % Say it's dog friendly
67 % Say there's wildlife
33 % Say it's walkable to grocery stores
20 % Say streets are well-lit
14 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

Apartments for Rent

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Contact for price
1-2 bd
1-2 ba
125 Kings Ridge Rd #f320a52c6,
Jackson, KY 41339
See more homes for rent in
Jackson
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Homes for sale near 27 Chestnut Dr

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FOR SALE BY OWNER
1.68 ACRES
$439,000
4 bd
2.5 ba
3,050 sqft
382 Kings Ridge Rd,
Jackson, KY 41339
NEW - 1 DAY AGO
FOR SALE BY OWNER
1 ACRE
$50,000
2 bd
1 ba
2,500 sqft
169 Roark Ridge Rd,
Jackson, KY 41339
FOR SALE BY OWNER
0.34 ACRES
$289,000
3 bd
2 ba
1,798 sqft
431 Snowden Branch Rd,
Altro, KY 41339
0.25 ACRES
$49,500
2 bd
1 ba
1,000 sqft
3654 Kentucky Ave #541,
Jackson, KY 41339
Trifecta Real Estate Experts, Imagine MLS
2.28 ACRES
$275,000
3 bd
2 ba
1,980 sqft
5487 W State Highway 30,
Jackson, KY 41339
CENTURY 21 Advantage Realty, Imagine MLS
42.03 ACRES
$395,900
3 bd
1 ba
2,300 sqft
1267 Lower Taulbee Fork Rd,
Vancleve, KY 41385
RO&CO Real Estate, Imagine MLS
See more homes for sale in
Jackson
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Off Market Homes Near 27 Chestnut Dr

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SOLD
JUL 15, 2026
$210,000
4 bd
3.5 ba
3,400 sqft
966 Highland Ave,
Jackson, KY 41339
Trifecta Real Estate Experts, Imagine MLS
SOLD
JUN 29, 2026
$240,000
3 bd
1 ba
1,329 sqft
2030 Quicksand Rd,
Jackson, KY 41339
SOLD
JAN 12, 2026
$255,000
1,800 sqft
131 Summer Ridge Dr,
Jackson, KY 41339
SOLD
JAN 5, 2026
$137,000
2,496 sqft
11 John St,
Jackson, KY 41339
SOLD
DEC 11, 2025
$130,000
3 bd
1 ba
816 sqft
57 Turner Dr,
Jackson, KY 41339
SOLD
DEC 11, 2025
$175,000
4 bd
2 ba
2,072 sqft
47 Williams Trailer Court Rd,
Jackson, KY 41339
SOLD
DEC 11, 2025
$137,000
2 bd
2,968 sqft
91 John St,
Jackson, KY 41339
SOLD
NOV 24, 2025
$240,000
3 bd
2.5 ba
2,754 sqft
93 Collier Ave,
Jackson, KY 41339
Trifecta Real Estate Experts, Imagine MLS
SOLD
OCT 31, 2025
$215,600
963 Highland Ave,
Altro, KY 41339
Trifecta Real Estate Experts, Imagine MLS
OFF MARKET
Est. $257,700
3 bd
2 ba
3,576 sqft
76 State Dr,
Jackson, KY 41339
See more homes for sale in
Jackson
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27 Chestnut Dr
Jackson, KY 41339

$253,400

$253,400