2727 Rolling Pines Rd
Chipley, FL 32428
4 Beds
3 Baths
2,528 sqft (on 5.60 acres)
4 Beds
3 Baths
2,528 sqft
(on 5.60 acres)
Local Information
- Map ViewExplore the area around 2727 Rolling Pines Rd.
- Schools1 Preschool School4 Elementary Schools4 Middle Schools4 High Schools
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
2006
Lot Size
5.6 acres
Living Area
2,528 sqft
Price/Sqft
$175
Parking
Garage
About this House
Beautiful Home overlooking Pine Lake... sitting on over 5 acres. Brick Rancher 4 bedroom 3bath plus office. as you enter the foyer office to left, opens to great room dining room and kitchen. Oversized master bedroom with 2 walk in closets. Master bath has separate shower and soaking tub. Additional 2 bedroom with Jack and Jill bath. 4th bedroom is conveniently located across from hall bath. Crown Molding, chair rail and lots of windows and French door to let in natural light and view of the Lake. Concrete drive with oversized parking pad. A Must See!!!
2727 Rolling Pines Rd, Chipley, FL 32428 is a 4 bedroom, 3 bathroom, 2,528 sqft single-family home built in 2006. It last sold for $249,900 on Dec 6, 2018. It is currently off market. The Trulia Estimate is $441,700, with a rent estimate of $2,650/month.
Home Details for 2727 Rolling Pines Rd
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Heating & Cooling Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 1Floors: Tile |
Interior Details Types of Rooms: Dining Room |
Appliances & Utilities DishwasherMicrowaveRefrigerator |
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Exterior Home Features Roof: OtherExterior: BrickPatioPorch |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
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Year Built Year Built: 2006Year Updated: 2006 |
Property Type / Style Property Type: Single Family HomeArchitecture: Other |
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Units in Building: 1 |
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Lot Area: 5.60 acres |
Price History for 2727 Rolling Pines Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 12/06/2018 | $249,900 | Sold | CPAR #677129 |
| 10/09/2018 | $249,900 | Listed For Sale | Agent Provided |
| 02/08/2015 | $290,000 | ListingRemoved | Agent Provided |
| 01/18/2015 | $290,000 | Listed For Sale | Agent Provided |
| 10/12/2012 | $175,000 | ListingRemoved | Agent Provided |
| 10/03/2012 | $175,000 | PriceChange | Agent Provided |
| 08/22/2012 | $239,000 | Listed For Sale | Agent Provided |
| 04/01/2012 | $245,000 | ListingRemoved | Agent Provided |
| 03/25/2012 | $245,000 | PriceChange | Agent Provided |
| 01/22/2012 | $249,000 | PriceChange | Agent Provided |
| 10/13/2011 | $259,900 | Listed For Sale | Agent Provided |
| 05/24/2010 | $225,000 | Sold | N/A |
| 04/09/2009 | $329,900 | ListingRemoved | Agent Provided |
| 03/17/2009 | $329,900 | Listed For Sale | Agent Provided |
Market trends in Chipley
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
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Available listings
110
14MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $2,534 |
| Assessment | $383,568 |
Home facts updated by county records
Comparable Sales for 2727 Rolling Pines Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.19 | Single-Family Home | $452,900 | 05/29/26 | 3 | 2 | 1,980 | |
0.54 | Single-Family Home | $434,000 | 09/17/25 | 3 | 2.5 | 1,831 | |
0.49 | Single-Family Home | $700,000 | 05/15/26 | 3 | 2.5 | 2,324 | |
1.10 | Single-Family Home | $750,000 | 10/17/25 | 4 | 3.5 | 3,048 | |
1.07 | Single-Family Home | $350,100 | 10/17/25 | 1 | 1 | 3,500 | |
1.69 | Single-Family Home | $350,000 | 03/31/26 | 2 | 2 | 1,184 | |
2.37 | Single-Family Home | $475,000 | 06/16/26 | 3 | 3 | 3,169 | |
1.84 | Single-Family Home | $5,100 | 01/21/26 | 3 | 2 | 1,496 | |
2.37 | Single-Family Home | $475,000 | 06/16/26 | 2 | 2 | 2,600 | |
2.08 | Single-Family Home | $351,000 | 09/26/25 | 3 | 3 | 1,572 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
FOR SALE7.32 ACRES
SOLDMAY 29, 2026
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SOLDFEB 23, 2026
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FOR SALE1.87 ACRES
SOLDMAY 15, 2026
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Assigned Schools
These are the assigned schools for 2727 Rolling Pines Rd.
- Chipley High School
- 9-12
- Public
- 534 Students
4/10GreatSchools RatingParent Rating AverageAvoid all Washington County schools. They can't get ride of all the bullies in schoolParent Review8mo ago - Kate M. Smith Elementary School
- K-5
- Public
- 874 Students
4/10GreatSchools RatingParent Rating AverageBus system is extremely unsafe, they don't care about bullying, favoritism is huge here, terrible lack of communication with parents, and teachers are always on their phones.We just took our child out recently.Parent Review8mo ago - Vernon High School
- 9-12
- Public
- 295 Students
3/10GreatSchools RatingParent Rating AverageNo new age schools' here in Washington CountyParent Review8mo ago - Roulhac Middle School
- 6-8
- Public
- 386 Students
7/10GreatSchools RatingParent Rating AverageI feel that this school has a great plan for our students acedemic future. The staff has shown great concern for our kids.Parent Review15y ago - Vernon Elementary School
- PK-5
- Public
- 623 Students
4/10GreatSchools RatingParent Rating AverageDisrespectfulWill not listen to you with your concerns and take them seriously. Don't move your children here not what it seems to be. Very judgemental woman here that wants to talk drama not school or their job. Public schools are supposed to be a safe haven. Not safe here.Other Review4mo ago - Vernon Middle School
- 6-8
- Public
- 267 Students
5/10GreatSchools RatingParent Rating AverageVernon Middle School is a great school but there's always room for improvement!!! I like the fact that it's an family oriented school and for the most part everyone gets a alone, and if not the problem or issue is always handled in a professional manner. As far as improvements the academics area needs some help, but we have good teachers that care about our students and they will help anyway they can.Parent Review12y ago - Washington Virtual Instruction Program
- K-12
- Public
NAGreatSchools RatingParent Rating Average
No reviews available for this school. - Washington Virtual Franchise
- K-12
- Public
- 12 Students
NAGreatSchools RatingParent Rating AverageNo reviews available for this school. 
Check out schools near 2727 Rolling Pines Rd.
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.
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Apartments for Rent
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Homes for sale near 2727 Rolling Pines Rd
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AUCTION6.3 ACRES
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NEW4.52 ACRES
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Off Market Homes Near 2727 Rolling Pines Rd
SOLDJUL 20, 2026
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SOLDJUN 30, 2026
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SOLDJUN 9, 2026- SOLDMAY 29, 2026
SOLDAPR 30, 2026- SOLDAPR 27, 2026
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