Are yards well-kept in Dillsboro, IN?

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

Would people walk alone at night in Dillsboro, IN?

As of early 2026, 100% of users say people would walk alone at night

Is Dillsboro, IN walkable to restaurants?

As of early 2026, 100% of users say it's walkable to restaurants

Does Dillsboro, IN show holiday spirit?

As of early 2026, 100% of users say there's holiday spirit

Is there wildlife in Dillsboro, IN?

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

Does Dillsboro, IN have sidewalks?

As of early 2026, 75% of users say there are sidewalks

Is parking easy in Dillsboro, IN?

As of early 2026, 75% of users say parking is easy

Is Dillsboro, IN walkable to grocery stores?

As of early 2026, 67% of users say it's walkable to grocery stores

Are there community events in Dillsboro, IN?

As of early 2026, 67% of users say there are community events

Do kids play outside in Dillsboro, IN?

As of early 2026, 67% of users say kids play outside

Is Dillsboro, IN quiet?

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

Is a car needed in Dillsboro, IN?

As of early 2026, 67% of users say car is needed

Is Dillsboro, IN dog-friendly?

As of early 2026, 50% of users say it's dog friendly

Do residents of Dillsboro, IN plan to stay at least 5 years?

As of early 2026, 50% of users say they plan to stay for at least 5 years

Are neighbors friendly in Dillsboro, IN?

As of early 2026, 40% of users say neighbors are friendly

What is 5539 Milton Bear Branch Rd estimated to be worth?

Trulia's estimated value for 5539 Milton Bear Branch Rd in Dillsboro, IN is $340,400 .

What is the price history for 5539 Milton Bear Branch Rd?

5539 Milton Bear Branch Rd in Dillsboro, IN last sold for $235,000 in June 2021.

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

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

What are the closest schools to 5539 Milton Bear Branch Rd?

The closest schools to 5539 Milton Bear Branch Rd in Dillsboro, IN are Ohio County Elementary-Middle School (Pre-K, rated 6/10), Ohio County Middle School (rated 8/10), Rising Sun High School (rated 5/10).

Does 5539 Milton Bear Branch Rd have air conditioning?

Yes, 5539 Milton Bear Branch Rd in Dillsboro, IN has air conditioning.

How big is the lot at 5539 Milton Bear Branch Rd?

The lot at 5539 Milton Bear Branch Rd in Dillsboro, IN is about 3.2 acres .

OFF MARKET

$340,400

Trulia Estimate

3 Beds
2 Baths
1,500 sqft (on 3.20 acres)

5539 Milton Bear Branch Rd, Dillsboro, IN 47018

Est. Refi. Payment $2,074/mo*

Refinance Your Home

Currently Off Market - Sold Jun 21, 2021 for $235,000

Home Value

Trulia Estimate

$340K

Since last month

$4K (-1.1%)

Since last year

$7K (+2.2%)

Since last sale

$106K (+45.1%)

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 +80% in the last 10 years

Month	Estimated value
2026
August 2026	$341K
August 2026	$340K
July 2026	$345K
June 2026	$347K
May 2026	$348K
April 2026	$344K
March 2026	$335K
February 2026	$332K
January 2026	$329K
2025
December 2025	$331K
November 2025	$335K
October 2025	$336K
September 2025	$331K
August 2025	$334K
July 2025	$333K
June 2025	$331K
May 2025	$333K
April 2025	$329K
March 2025	$333K
February 2025	$329K
January 2025	$325K
2024
December 2024	$323K
November 2024	$324K
October 2024	$322K
September 2024	$320K
August 2024	$320K
July 2024	$322K
June 2024	$322K
May 2024	$322K
April 2024	$321K
March 2024	$314K
February 2024	$309K
January 2024	$305K
2023
December 2023	$303K
November 2023	$303K
October 2023	$306K
September 2023	$306K
August 2023	$304K
July 2023	$306K
June 2023	$307K
May 2023	$304K
April 2023	$301K
March 2023	$296K
February 2023	$286K
January 2023	$283K
2022
December 2022	$283K
November 2022	$283K
October 2022	$286K
September 2022	$284K
August 2022	$282K
July 2022	$262K
June 2022	$261K
May 2022	$257K
April 2022	$255K
March 2022	$253K
February 2022	$252K
January 2022	$249K
2021
December 2021	$248K
November 2021	$242K
October 2021	$241K
September 2021	$241K
August 2021	$237K
July 2021	$236K
June 2021	$247K
May 2021	$215K
April 2021	$210K
March 2021	$209K
February 2021	$208K
January 2021	$205K
2020
December 2020	$204K
November 2020	$203K
October 2020	$199K
September 2020	$198K
August 2020	$198K
July 2020	$197K
June 2020	$196K
May 2020	$196K
April 2020	$195K
March 2020	$195K
February 2020	$194K
January 2020	$194K
2019
December 2019	$194K
November 2019	$192K
October 2019	$192K
September 2019	$191K
August 2019	$191K
July 2019	$190K
June 2019	$189K
May 2019	$189K
April 2019	$188K
March 2019	$186K
February 2019	$186K
January 2019	$185K
2018
December 2018	$184K
November 2018	$183K
October 2018	$182K
September 2018	$181K
August 2018	$180K
July 2018	$180K
June 2018	$179K
May 2018	$178K
April 2018	$207K
March 2018	$188K
February 2018	$185K
January 2018	$177K
2017
December 2017	$179K
November 2017	$177K
October 2017	$185K
September 2017	$188K
August 2017	$174K
July 2017	$184K
June 2017	$194K
May 2017	$190K
April 2017	$195K
March 2017	$186K
February 2017	$184K
January 2017	$174K
2016
December 2016	$201K
November 2016	$195K
October 2016	$183K
September 2016	$190K

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
Southfork Rd, Dillsboro, IN	1.24	Single-Family Home	$100,000	09/30/25	3	1	1,800
11870 W Laughery Creek Rd, Dillsboro, IN	1.90	Single-Family Home	$55,000	10/02/25	1	-	192
7095 State Route 62, Dillsboro, IN	3.78	Single-Family Home	$170,000	11/07/25	2	1	1,856
4852 Cass Union Rd, Rising Sun, IN	3.80	Single-Family Home	$190,000	11/17/25	2	1	876
15407 Aberdeen Rd, Bennington, IN	4.54	Single-Family Home	$315,000	05/15/26	3	2	1,320
9750 Front St, Dillsboro, IN	4.43	Single-Family Home	$175,100	06/15/26	3	1.5	1,426
13186 Sunset Dr, Dillsboro, IN	4.52	Single-Family Home	$215,000	07/16/26	4	2	924
14998 Works Rd, Bennington, IN	3.52	Single-Family Home	$850,000	06/03/26	4	4	5,872
8505 Martin Rd, Dillsboro, IN	3.28	Single-Family Home	$225,000	05/15/26		-	-

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
4444 Pate Rd, Dillsboro, IN 47018	2.05	$599,000	3	2	2,523	For Sale
5565 Milton Bear Branch Rd, Dillsboro, IN 47018	0.04	$370,200	4	3	2,576	Off Market
5510 Milton Bear Branch Rd, Dillsboro, IN 47018	0.04	$356,200	1	1	3,586	Off Market
13099 Southfork Rd, Dillsboro, IN 47018	1.60	$264,100	3	2	1,560	Off Market
12765 Laughery Creek Rd, Dillsboro, IN 47018	0.45	$249,500	3	1	1,227	Off Market
12707 Southfork Rd, Dillsboro, IN 47018	1.64	$517,900	2	2	1,290	Off Market
5505 Milton Bear Branch Rd, Dillsboro, IN 47018	0.05	$385,800	4	3	2,413	Off Market
5475 Milton Bear Branch Rd, Dillsboro, IN 47018	0.10	$248,400	4	3	1,512	Off Market
5425 Milton Bear Branch Rd, Dillsboro, IN 47018	0.18	$244,700	3	2	1,296	Off Market
4055 Pate Rd, Dillsboro, IN 47018	1.94	$219,800	3	1	1,440	Off Market
3745 Milton Bear Branch Rd, Dillsboro, IN 47018	2.04	$293,900	3	1	1,512	Off Market
13587 Iceberg Rd, Dillsboro, IN 47018	2.31	$64,100	Studio	1	672	Off Market

Local Information

Map ViewExplore the area around 5539 Milton Bear Branch Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 2005

3.2 acre lot

1,500 sqft

$227/sqft

Garage

About this House

Charming and relaxing country home on 3.2 acres. Lots of room to grow and play. Large country kitchen, remodeled Pottery Barn like baths. Open floor plan with kitchen opening to deck retreat and wonderful back yard. Gorgeous valley views with the full unfinished lower level with walkout just waiting for your touches.

5539 Milton Bear Branch Rd, Dillsboro, IN 47018 is a 3 bedroom, 2 bathroom, 1,500 sqft single-family home built in 2005. It last sold for $235,000 on Jun 21, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $340,400, with a rent estimate of $2,101/month.

Home Details for 5539 Milton Bear Branch Rd

Interior Features
Heating & Cooling Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility Stories: 1
Interior Details Number of Rooms: 5Types of Rooms: Family RoomCeiling Fan
Appliances & Utilities DishwasherMicrowaveRefrigerator

Exterior Features
Exterior Home Features Roof: AsphaltDeckPatio
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached

Property Information
Year Built Year Built: 2005
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 3.20 acres

Price and Tax history

Date	Event	Price
Jun 21, 2021 Source: N/A	Sold	$235,000
Jul 6, 2020 Source: Agent Provided	ListingRemoved	$195,000
May 14, 2020 Source: Agent Provided	Pending	$195,000
May 12, 2020 Source: Agent Provided	Listed For Sale	$195,000
May 7, 2018 Source: Cincy MLS #1570972	Sold	$177,000
Mar 13, 2018 Source: Agent Provided	Listed For Sale	$179,900
Dec 1, 2017 Source: Agent Provided	ListingRemoved	$169,900
Oct 23, 2017 Source: Agent Provided	PriceChange	$169,900 Price decreased by 6%
Sep 6, 2017 Source: Agent Provided	PriceChange	$179,900 Price increased by 6%
May 12, 2017 Source: N/A	Listed For Sale	$169,900

Year	Property tax	Tax assessment
2025	$1,931	$262,300

Additional Cost

Market trends in Dillsboro

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

Around this home

Ohio County Elementary-Middle School
PK-5
Public
409 Students
Rising Sun-Ohio County Com
6/10
GreatSchools Rating
Parent Rating Average
Our son is excelling at this school so far. He is in first grade. The teacher communicate well and are very caring. The current administrators go above and beyond.
Parent Review
4y ago
10 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 Dillsboro

At least 2 Trulia users voted on each feature.

100 % Say yards are well-kept
100 % Say people would walk alone at night
100 % Say it's walkable to restaurants
100 % Say there's holiday spirit
75 % Say there's wildlife
75 % Say there are sidewalks
75 % Say parking is easy
67 % Say it's walkable to grocery stores
67 % Say there are community events
67 % Say kids play outside
67 % Say it's quiet
67 % Say car is needed
50 % Say it's dog friendly
50 % Say they plan to stay for at least 5 years
40 % Say neighbors are friendly

Sourced by Trulia users. Learn more about our methodology.

amybentley2011
13y ago
"I own a property on lake dilldear drive and the conditions out here are terrible! the septic smell here is awful and thieves out here are terrible. the area is run down and getting worse. drugs in this area is whats causing the theft. i would NOT recommend it at all to anyone."
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Frequently asked questions about 5539 Milton Bear Branch Rd

What is 5539 Milton Bear Branch Rd estimated to be worth?
Trulia's estimated value for 5539 Milton Bear Branch Rd in Dillsboro, IN is $340,400.
What is the price history for 5539 Milton Bear Branch Rd?
5539 Milton Bear Branch Rd in Dillsboro, IN last sold for $235,000 in June 2021.
Is Dillsboro a buyer's or seller's market?
Dillsboro is currently a buyer's market, based on recent for-sale activity.
What are the closest schools to 5539 Milton Bear Branch Rd?
The closest schools to 5539 Milton Bear Branch Rd in Dillsboro, IN are Ohio County Elementary-Middle School (Pre-K, rated 6/10), Ohio County Middle School (rated 8/10), Rising Sun High School (rated 5/10).
Does 5539 Milton Bear Branch Rd have air conditioning?
Yes, 5539 Milton Bear Branch Rd in Dillsboro, IN has air conditioning.
How big is the lot at 5539 Milton Bear Branch Rd?
The lot at 5539 Milton Bear Branch Rd in Dillsboro, IN is about 3.2 acres.