2774 Rolling Pines Rd, Chipley, FL 32428
Property image
Property image
PENDING

$224,900

  • 2 Beds
  • 2 Baths
  • 1,176 sqft

2774 Rolling Pines Rd, Chipley, FL 32428

Est. Mortgage $1,557/mo*
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Home Highlights

Single-Family Home
Built in 2003
$191/sqft

Local Information

  • Map ViewExplore the area around 2774 Rolling Pines Rd.
  • Schools1 Preschool School4 Elementary Schools4 Middle Schools4 High Schools
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Several other shedsLarge outbuildingSplit bedroom plan
This 2 bedroom, 2bath 1 story home located on 1.9 acres with approximately 241' on Hwy 77 Is move in ready. Zoned single family but, seller says it can be split. Large outbuilding, several other sheds, brand new stainless electric stove & refrigerator. Split bedroom plan.
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Home Details for 2774 Rolling Pines Rd

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: Central AirHeating Fuel: Electric

Days on Market

Days on Market: 30 days on Trulia

Property Information

Year Built
Year Built: 2003
Property Type / Style
Property Type: Single Family Home

Building

Levels, Entrance, & Accessibility
Disabled Access

Price & Status

Price
Price Per Sqft: $191

Agent Information

Listing Agent
MLS/Source ID: 794560

Around this home

What Locals Say about Chipley

At least 24 Trulia users voted on each feature.

  • 92 % Say yards are well-kept

  • 88 % Say car is needed

  • 86 % Say parking is easy

  • 86 % Say there's holiday spirit

  • 83 % Say it's quiet

  • 64 % Say people would walk alone at night

  • 62 % Say it's dog friendly

  • 55 % Say kids play outside

  • 53 % Say there's wildlife

  • 51 % Say neighbors are friendly

  • 50 % Say there are sidewalks

  • 48 % Say they plan to stay for at least 5 years

  • 41 % Say it's walkable to grocery stores

  • 34 % Say streets are well-lit

  • 31 % Say it's walkable to restaurants

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Merissa Woods
    "I don’t have a neighborhood I live out in the woods, but Chipley itself is very good for dogs and walking dogs in the sidewalks and the capabilities of doing that. "
    1
    Flag
  • Mandi W.
    "golf course, ponds, lakes, dirt roads, Halloween tons of tricker treating. keep main grass area cut. looks very homie"
    0
    Flag
  • Carol
    "I have lived in this neighborhood for three years. Our neighbors seem to be very nice. There is government housing down the road and a lot of people walk up and down the sidewalks. All seem to be nice. "
    1
    Flag
  • Tonya G. H.
    "if you like a country feel but still belong to a community this is the place. Woods and ponds to explore but also have neighbors and community functions. "
    0
    Flag
  • Kayla H.
    "Home town feeling wether it is your home town or not. Your neighbor is my neighbor. If you ever need a helping hand just reach out they are everywhere here."
    0
    Flag
  • Dafuss39
    "I live at the end of the road on the lake with traffic no trick-or-treaters and no visitors very safe neighborhood"
    1
    Flag
  • Troyrackley
    "This area is a great place to walk your dog. Courteous neighbors, friendly passers-by, and a lovely area overall. I would highly recommend living here. "
    0
    Flag
  • Wanda S.
    "It's okay, it's a long way to town, but you get used to it. We have a general store, a volunteer fire department, a library, and a Baptist Mission. We are also surrounded by nearby churches in neighboring areas. We have a fresh spring lake nearby, great for camping and cookouts if you have an ATV. Dependable transportation is a MUST. Military Retirees especially welcome. I'm a vet, and would LOVE some friendly, Christ Loving Peers. Must Love Animals (4 legged types.) i'm at 537. Come on by."
    0
    Flag
  • Peaden
    "Great hunting, fishing, swimming, golfing. Very quiet area. Low crime. 35 miles to beaches. "
    0
    Flag

Market trends in Chipley

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
116
5MoM

Home Value

Trulia Estimate
$219K
Since last month
Decreased$5K (-2.2%)
Since last year
Increased$34K (+18.6%)
Since last sale
Decreased$4K (-1.6%)
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 +149% in the last 10 years
MonthEstimated value
2026
September 2026$218K
August 2026$223K
July 2026$201K
June 2026$206K
May 2026$205K
April 2026$199K
March 2026$194K
February 2026$186K
January 2026$182K
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
5095 Pine Ridge Dr, Chipley, FL
0.37
Single-Family Home
$255,000
07/29/26
1
1
1,140
5192 Pine Ridge Dr, Chipley, FL
0.45
Single-Family Home
$452,900
05/29/26
3
2
1,980
2789 Summer Dr, Chipley, FL
0.29
Single-Family Home
$700,000
05/15/26
3
2.5
2,324
5068 Airpark Blvd, Chipley, FL
0.83
Single-Family Home
$350,100
10/17/25
1
1
3,500
3068 Woodymarion Dr, Chipley, FL
1.43
Single-Family Home
$245,000
07/30/26
3
2
1,650
3068 Woodymarion Rd, Chipley, FL
1.43
Unknown
$245,000
07/30/26
-
-
5084 Spring Pond Rd, Chipley, FL
0.82
Single-Family Home
$750,000
10/17/25
4
3.5
3,048
4958 Lake Ridge Rd, Chipley, FL
1.98
Single-Family Home
$350,000
03/31/26
2
2
1,184
3097 Woodymarion Dr, Chipley, FL
1.54
Single-Family Home
$5,100
01/21/26
3
2
1,573

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
State Highway 77, Chipley, FL 32428
0.13
$300,000
-
-
-
Recently Sold
2759 Rolling Pines Rd, Chipley, FL 32428
0.11
$125,000
-
-
-
Recently Sold
2789 Summer Dr, Chipley, FL 32428
0.29
$700,000
3
2.5
2,324
Recently Sold
Pine Ridge Dr, Chipley, FL 32428
0.27
$63,900
-
-
-
For Sale
1 Pine Ridge Dr, Chipley, FL 32428
0.32
$90,000
-
-
-
For Sale
6355 Highway 77, Chipley, FL 32428
0.35
-
-
-
-
Off Market
2807 Summer Dr, Chipley, FL 32428
0.43
-
-
-
-
Off Market
5095 Pine Ridge Dr, Chipley, FL 32428
0.37
$255,000
1
1
1,140
Recently Sold
5203 Pine Ridge Dr, Chipley, FL 32428
0.38
-
-
-
-
Off Market
2850 Scenic Dr, Chipley, FL 32428
0.46
$252,700
3
2
1,422
Off Market
5080 Pine Ridge Dr, Chipley, FL 32428
0.41
$432,400
3
2.5
1,831
Off Market
5147 Pine Ridge Dr, Chipley, FL 32428
0.41
-
-
-
-
Off Market

Price and Tax history

DateEventPrice
Sep 25, 2026
Source: CPAR #794560
Sold
$222,000
Sep 4, 2026
Source: CPAR #794560
Pending
$224,900
Aug 25, 2026
Source: CPAR #794560
Listed For Sale
$224,900
Jul 26, 2001
Source: N/A
Sold
$30,500

LGBTQ Local Legal Protections

Trudy VanHorn, Beach Properties of Florida
Agent Phone: (850) 819-4335

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Frequently asked questions about 2774 Rolling Pines Rd

  • What is the estimated monthly payment for 2774 Rolling Pines Rd?
    Based on a $224,900 list price with 20% down at today's rates, the estimated monthly payment for 2774 Rolling Pines Rd in Chipley, FL is approximately $1,602 (about $1,253 principal & interest, $274 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Chipley?
    Residents describe Chipley, FL as well-kept, easy to park in, and quiet. Most residents say you need a car. See homes for sale in Chipley, FL.
  • What are the closest schools to 2774 Rolling Pines Rd?
    The closest schools to 2774 Rolling Pines Rd in Chipley, FL are Chipley High School (rated 4/10), Kate M. Smith Elementary School (rated 4/10), Roulhac Middle School (rated 7/10).
  • What is 2774 Rolling Pines Rd estimated to be worth?
    Trulia's estimated value for 2774 Rolling Pines Rd in Chipley, FL is $218,600.
  • Does 2774 Rolling Pines Rd have air conditioning?
    Yes, 2774 Rolling Pines Rd in Chipley, FL has air conditioning.
  • How big is the lot at 2774 Rolling Pines Rd?
    The lot at 2774 Rolling Pines Rd in Chipley, FL is about 1.9 acres.
2774 Rolling Pines Rd, Chipley, FL 32428 is a 2 bedroom, 2 bathroom, 1,176 sqft single-family home built in 2003. This property is currently available for sale and was listed by BHHS broker feed on Aug 26, 2026. The MLS # for this home is MLS# 794560.