550 Bennett Dr, Chipley, FL 32428
Property image
Property image
PENDING

$159,900

  • 3 Beds
  • 2 Baths
  • 1,431 sqft

550 Bennett Dr, Chipley, FL 32428

Est. Mortgage $1,097/mo*
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Home Highlights

Single-Family Home
Built in 1993
$112/sqft

Local Information

  • Map ViewExplore the area around 550 Bennett Dr.
  • Schools1 Preschool School4 Elementary Schools4 Middle Schools4 High Schools
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:New roofQuartz countertopsOversized laundry roomUpdated kitchenNew stainless steel appliancesWhite shaker cabinets
Recently renovated, this 3-bedroom, 2-bath home at 550 Bennett Drive in Chipley features luxury vinyl plank flooring throughout and an open-concept living area. The updated kitchen offers white shaker cabinets, quartz countertops, and new stainless steel appliances. An oversized laundry room provides plenty of space for additional storage or a freezer. The primary bedroom includes a private bathroom with a shower, while the second bathroom is conveniently located off the hallway. A new roof and new water heater add to the home's recent improvements.
Last check for updates: about 8 hours ago
Listing courtesy of Cindy R Birge, (850) 258-9442
Elite Realty
Originating MLS: Central Panhandle Association of REALTORS
Source: CPAR, MLS#796661

Home Details for 550 Bennett Dr

Interior Features

Interior Details
Number of Rooms: 6Types of Rooms: Bedroom, Master Bathroom, Kitchen, Living Room, Utility Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Appliances & Utilities
Utilities: Electricity AvailableAppliances: Electric Oven, Electric Water Heater
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Plank, Vinyl
Levels, Entrance, & Accessibility
Stories: 1Floors: Plank, Vinyl

Exterior Features

Exterior Home Features
Roof: MetalFoundation: Slab
Parking & Garage
No GarageNo Attached Garage
Frontage
Road Frontage: City StreetResponsible for Road Maintenance: Public Maintained RoadNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 12Days on Market: 20

Property Information

Year Built
Year Built: 1993
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: BrickNot a New Construction
Property Information
Parcel Number: 000000000026990001

Price & Status

Price
List Price: $159,900Price Per Sqft: $112
Status Change & Dates
Off Market Date: Wed Oct 28 2026

Active Status

MLS Status: Pending

Location

Direction & Address
City: ChipleyCommunity: [No Recorded Subdiv]

Agent Information

Listing Agent
Listing ID: 796661

Building

Building Area
Building Area: 1431 Square Feet

Community

Community Features: Short Term Rental Allowed

HOA

Association for this Listing: Central Panhandle Association of REALTORSNo HOA

Lot Information

Lot Area: 8712 sqft

Listing Info

Special Conditions: Listed As-Is

Rental Terms, Policies & Fees

Are Units Furnished: None

Miscellaneous

Mls Number: 796661Living Area Range Units: Square FeetAbove Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Units: Square FeetUniversal Property Id: US-12133-N-000000000026990001-R-N

Additional Information

Short Term Rental Allowed

Price and Tax history

DateEventPrice
Oct 29, 2026
Source: CPAR #796661
Pending
$159,900
Oct 16, 2026
Source: CPAR #796661
Listed For Sale
$159,900
Feb 26, 2026
Source: N/A
Sold
$60,000
Apr 18, 2022
Source: CPAR #723861
Sold
$85,640
Dec 10, 2012
Source: N/A
Sold
$17,300

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. "
  • Mandi W.
    "golf course, ponds, lakes, dirt roads, Halloween tons of tricker treating. keep main grass area cut. looks very homie"
  • 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. "
  • 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. "
  • 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."
  • Dafuss39
    "I live at the end of the road on the lake with traffic no trick-or-treaters and no visitors very safe neighborhood"
  • 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. "
  • 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."
  • Peaden
    "Great hunting, fishing, swimming, golfing. Very quiet area. Low crime. 35 miles to beaches. "

Market trends in Chipley

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
104
12
MoM
Sourced by Trulia Market Trends

Home Value

Trulia Estimate
$152K
Since last month
Increased$49K (+47.2%)
Since last year
Increased$14K (+10.4%)
Since last sale
Increased$92K (+153.7%)
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 +70% in the last 10 years
MonthEstimated value
2026
November 2026$152K
October 2026$152K
September 2026$103K
August 2026$95K
July 2026$93K
June 2026$95K
May 2026$94K
April 2026$91K
March 2026$135K
February 2026$129K
January 2026$130K
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
0.14
Single-Family Home
$60,000
08/07/26
3
1
1,064
0.51
Single-Family Home
$80,000
01/28/26
3
2
1,080
0.41
Single-Family Home
$164,900
11/25/25
3
2
1,245
0.20
Single-Family Home
$194,500
08/11/26
2
2
1,338
0.65
Single-Family Home
$106,000
10/16/26
3
2
1,823
0.35
Single-Family Home
$160,000
02/13/26
3
1
1,343
0.81
Single-Family Home
$65,000
01/07/26
3
2
1,878
0.61
Single-Family Home
$205,000
04/09/26
3
2
1,724

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
0.01
-
-
-
1,871
Off Market
0.02
$164,800
2
1
1,368
Off Market
0.05
$121,100
3
3
1,584
Off Market
0.06
$267,100
2
1.5
2,388
Off Market
0.06
-
-
-
-
Off Market
0.07
$273,100
Studio
2
2,196
Off Market
0.07
-
-
-
-
Off Market
0.07
-
-
-
-
Off Market
0.07
-
-
-
-
Off Market
0.07
-
-
-
-
Off Market
0.07
-
-
-
-
Off Market
0.07
-
-
-
-
Off Market
0.10
$148,200
Studio
1
1,412
Off Market
0.10
$188,700
3
2
1,557
Off Market
0.11
$201,700
Studio
2
1,628
Off Market
0.13
$142,000
Studio
2
1,134
Off Market
0.13
-
-
-
-
Off Market
0.13
$108,000
Studio
2
1,134
Off Market
0.14
$150,800
Studio
2
1,008
Off Market
0.14
$60,000
3
1
1,064
Recently Sold

LGBTQ Local Legal Protections

Cindy R Birge, Elite Realty
Agent Phone: (850) 258-9442
IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.

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Frequently asked questions about 550 Bennett Dr

  • What is the estimated monthly payment for 550 Bennett Dr?
    Based on a $159,900 list price with 20% down at today's rates, the estimated monthly payment for 550 Bennett Dr in Chipley, FL is approximately $1,131 (about $861 principal & interest, $195 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 550 Bennett Dr?
    The closest schools to 550 Bennett Dr in Chipley, FL are Chipley High School (rated 3/10), Kate M. Smith Elementary School (rated 3/10), Roulhac Middle School (rated 7/10).
  • What is 550 Bennett Dr estimated to be worth?
    Trulia's estimated value for 550 Bennett Dr in Chipley, FL is $152,100.
  • Does 550 Bennett Dr have air conditioning?
    Yes, 550 Bennett Dr in Chipley, FL has air conditioning.
  • How big is the lot at 550 Bennett Dr?
    The lot at 550 Bennett Dr in Chipley, FL is about 0.20 acres (8,712 sq ft).
550 Bennett Dr, Chipley, FL 32428 is a 3 bedroom, 2 bathroom, 1,431 sqft single-family home built in 1993. This property is currently available for sale and was listed by CPAR on Oct 16, 2026. The MLS # for this home is MLS# 796661.