5392 CHANDLER DRIVE, Winter Haven, FL 33884
SOLD
APR 24, 2026

$349,500

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 3,034 sqft

5392 CHANDLER DRIVE, Winter Haven, FL 33884

Est. Refi. Payment $2,373/mo*
Refinance Your Home
Currently Off Market - Sold Apr 24, 2026 for $349,000 (0% below list price)

Home Value

Trulia Estimate
$350K
Since last month
Increased$1K (+0.4%)
Since last year
Decreased$40K (-10.3%)
Since last sale
Increased$1K (+0.4%)
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 decreased by -17% in the last 10 years
MonthEstimated value
2026
September 2026$350K
August 2026$349K
July 2026$347K
June 2026$346K
May 2026$347K
April 2026$349K
March 2026$342K
February 2026$341K
January 2026$341K
2025

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
341 STERLING DRIVE, Winter Haven, FL
0.52
Single-Family Home
$380,000
04/16/26
4
3
2,008
4504 RIVIERA DRIVE, Winter Haven, FL
0.30
Single-Family Home
$437,000
05/08/26
3
2.5
2,614
5 TWILIGHT LANE, Winter Haven, FL
0.21
Single-Family Home
$265,000
04/09/26
3
2
1,454
4034 DORAL, Winter Haven, FL
0.58
Single-Family Home
$375,000
03/26/26
4
3
2,674
7182 SUMMIT DRIVE, Winter Haven, FL
0.56
Single-Family Home
$348,000
03/31/26
4
2
1,888
4401 MAHOGANY RUN, Winter Haven, FL
0.34
Single-Family Home
$292,500
05/05/26
3
2.5
1,975
5750 HARBOR ISLE BOULEVARD, Winter Haven, FL
0.23
Single-Family Home
$272,000
03/30/26
3
2
1,238

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
5560 BESS LANE, Winter Haven, FL 33884
0.08
$302,800
4
2.5
2,242
Off Market
5445 CHANDLER DRIVE, Winter Haven, FL 33880
0.08
$290,000
4
3
3,010
For Sale
5320 MICHAEL DRIVE, Winter Haven, FL 33884
0.12
$315,700
3
2.5
2,242
Off Market
4205 SPY GLASS CT, Winter Haven, FL 33884
0.17
$521,100
4
2.5
2,262
Off Market
5808 DRIFTWOOD DRIVE, Winter Haven, FL 33884
0.17
$379,600
4
2
2,046
Off Market
4927 WILLOWBROOK CIRCLE, Winter Haven, FL 33884
0.21
$460,200
3
2
1,900
Off Market
5880 DRIFTWOOD DRIVE, Winter Haven, FL 33884
0.20
$265,500
3
2
1,582
Off Market
5730 HARBOR ISLE BOULEVARD, Winter Haven, FL 33884
0.20
$279,000
3
2
1,742
Off Market
7 LAMPLIGHT LANE, Winter Haven, FL 33884
0.20
$175,300
2
1
952
Off Market
5 TWILIGHT LANE, Winter Haven, FL 33884
0.21
$265,000
3
2
1,454
Recently Sold
7 TWILIGHT LANE, Winter Haven, FL 33884
0.22
$205,000
2
2
938
Recently Sold

Local Information

  • Map ViewExplore the area around 5392 CHANDLER DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2006
3,034 sqft
$115/sqft
2 Car Garage
HOA $42/mo

About this House

PEACEFUL WATERFRONT Living! Many Beautiful Features & Oversized Living Areas Great for Entertaining! 3.2 Miles to Legoland! Formal Living & Dining Rooms, Family Room, and BONUS Room Upstairs (great for crafts, reading, or toys). Primary Suite offers sitting area & plenty of closet space. So much Extra Space that you could have a roommate helping pay the mortgage. Beautiful Kitchen Featuring Extra Space with Cooking Island & LARGE WALK-IN PANTRY! Eat-in Space OVERLOOKING THE WATER! Enjoy Living in the Waterski Capital of the World Featuring the Chain of Lakes! All sizes are approximate. You will love this home!!
5392 CHANDLER DRIVE, Winter Haven, FL 33884 is a 4 bedroom, 3 bathroom, 3,034 sqft single-family home built in 2006. It last sold for the $349,900 asking price on Apr 24, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $349,500, with a rent estimate of $2,319/month.
Last check for updates: about 5 hours ago
Listed by Jenni Thompson, (863) 899-5255
KELLER WILLIAMS REALTY SMART, (863) 577-1234
Bought with: Eric Atkins, (813) 710-0311, LPT REALTY, LLC, (877) 366-2213
Originating MLS: Lakeland
Source: Stellar MLS, MLS#L4955399
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 5392 CHANDLER DRIVE

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Primary Bedroom, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 3034 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Electricity AvailableAppliances: Dishwasher, Electric Water Heater, Microwave, Range, RefrigeratorDishwasherLaundry: InsideMicrowaveRefrigerator
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Door: Sliding DoorsFlooring: Carpet, Porcelain Tile, Vinyl
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Carpet, Porcelain Tile, Vinyl
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Front PorchFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garage Dimensions: 19x22No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Frontage
Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 211

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Block, Stucco, Wood FrameNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 262901663574000150

Price & Status

Price
List Price: $349,900Price Per Sqft: $115/sqft
Status Change & Dates
Off Market Date: Mon Mar 23 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER HAVENCommunity: BENTLEY PLACE

Building

Building Area
Building Area: 3562 Square Feet

Community

Not Senior Community

HOA

HOA Name: Garrison Property ServicesHOA Phone: 863-353-2558Association for this Listing: LakelandHas an HOAHOA Fee: $42/Monthly

Lot Information

Lot Area: 7070 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: L4955399Water View: WaterShowing Requirements: Appointment Only, ShowingTimeUniversal Property Id: US-12105-N-262901663574000150-R-N

Price and Tax history

DateEventPrice
Apr 24, 2026
Source: Stellar MLS #L4955399
Sold
$349,000
Mar 24, 2026
Source: Stellar MLS #L4955399
Pending
$349,900
Nov 25, 2025
Source: Stellar MLS #L4955399
PriceChange
$349,900
Price decreased by 13%
Sep 9, 2025
Source: Stellar MLS #L4955399
PriceChange
$399,900
Price decreased by 6%
Aug 25, 2025
Source: Stellar MLS #L4955399
Listed For Sale
$424,900

Market trends in Winter Haven

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$258K
$2.5KMoM
Sale-to-List Price
98.3%
0.1%MoM
Price per sq ft
$160
$1MoM
Available listings
771
7MoM

Around this home

What Locals Say about Winter Haven

At least 800 Trulia users voted on each feature.

  • 83 % Say car is needed

  • 80 % Say parking is easy

  • 78 % Say yards are well-kept

  • 76 % Say it's dog friendly

  • 68 % Say there's holiday spirit

  • 64 % Say it's quiet

  • 61 % Say kids play outside

  • 49 % Say people would walk alone at night

  • 48 % Say there are sidewalks

  • 47 % Say they plan to stay for at least 5 years

  • 46 % Say streets are well-lit

  • 44 % Say neighbors are friendly

  • 43 % Say it's walkable to grocery stores

  • 32 % Say there's wildlife

  • 30 % Say it's walkable to restaurants

  • 24 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Cathyharris1222
    "Safe area for children and families "
    0
    Flag
  • Cocobrownie3
    "Freindly neighbors, Holloween is wonderful here, everyone loves to BBQ , and Santa Clause comes on Chismas Eve. Wonderful place to live. However, to schools are not so good. "
    0
    Flag
  • William David Evans
    "We have our personal cars have used uber a few times but not really necessary for us because we live close to most of the stores and restaurants "
    1
    Flag
  • Morgan Ivey-trask
    "Everyone is friendly and so nice. I like it here but I will be moving out soon to live in North Carolina to get my kids back and live a new life "
    2
    Flag
  • Madeline R
    "Its neighborly and quiet while still being close to the theme parks and airport. Ive lived here for 5 years and it was the best decision we made."
    0
    Flag
  • Miguel Catalano
    "Quiet neighborhood, everything you need is close by and affordable, and places of worship for everyone. Light traffic all the time and great restaurants all over town with views of the lake. Serenity is everywhere in Winter Haven."
    0
    Flag
  • Z64p52x99r
    "I don’t go to the community events in the area I solely go to work and home I enjoy this peace in the neighborhood "
    0
    Flag
  • John Van Volkenburgh
    "Quick. No issues as long as you don’t work in Orlando or Tampa. Rural and central to the state. Small town. I’m "
    0
    Flag
  • Jenna Strickler
    "Food giveaways, law enforcement always circling/passing by Security feels safe Not the best neighborhood overall, but I have not had an issue since living here. "
    0
    Flag
  • Emily Torres
    "I’ve lived close to this area for 3 years now and worked there for a year and a half. Very nice area !"
    1
    Flag
  • Anonymous
    "You can walk your dogs with no problems. Many houses are fenced. Dogs will bark but not bite. Dogs ca"
    0
    Flag
  • Bianca Nieves
    "A lot of cats on the NE side of winter haven other than that winter haven lots of parks for children good schools "
    4
    Flag
  • Nicole Horton
    "I don’t feel safe for my 13 year old son to walk to the middle school by himself. I drive him and pick him up every day."
    0
    Flag
  • Chris M
    "There is a farmers market every weekend. A lot of community activities every weekend. Christmas parade happened a few weekends ago. "
    1
    Flag
  • Yoflyboys
    "NW Winter Haven has turned into a dump site. Homeless has taken over bus stop. Inman park and the surrounding areas."
    4
    Flag
  • Oo7legend
    "Great for families to live in and feel part of a community. Needs more retailers, restaurants and higher rated schools."
    30
    Flag
  • April_stylist
    "Quiet hard working families, no issues with traffic or safety we love this area. Very friendly folks"
    5
    Flag
  • Angmartinez05
    "Not much to do in terms of attractions but safe everywhere. 45 min from either Orlando or Tampa. Friendly people "
    0
    Flag
  • Katia S.
    "I live there for 3 years ,it’s quiet,I don’t have any complaint against it.I recommend it for a start,no to stay for a long time .I live close to the park.i like it and I feel safe."
    1
    Flag
  • Atrollergirl
    "My commute is nice. I live 1 mile from Wahneta and I'm located near Bartow, Eagle Lake, Winter Haven."
    0
    Flag
  • Carly.m.williams
    "The area is a family friendly area. High traffic area also. Schools and shopping nearby. Legoland brings in a lot of traffic also"
    0
    Flag
  • Nakeem G.
    "My neighborhood in walking distance to a college, police station, farmers market, hair store, hospital/clinics and parks"
    11
    Flag
  • Joan
    "I live in this great neighborhood with great neighbors who get along. Quiet neighborhood. It feels safe."
    0
    Flag
  • Angela S.
    "Very busy front Street with big trucks daily passing by. Car speed a lot on the main road thru the area. "
    0
    Flag
  • Carly.m.williams
    "The area is very family friendly in my opinion. Never had any issues with neighbors. Quite a few stray cats but no issues."
    0
    Flag
  • Nancy F.
    "I see people walking there dogs daily. we have a dog park in the community very nice area they are allowed off the leash in the fenced in area, they can run and play freely, very friendly area for them all maintained spayed often to keep fleas away.. pet friendly area. "
    1
    Flag
  • Jennycomp
    "There are no sidewalks or places to walk your dogs. They are forced to use people’s yards and they get upset."
    0
    Flag
  • Gina K.
    "Halloween is great here!!! Trick or treating is like a giant party and there’s so much fun going on. "
    0
    Flag
  • Shelley P.
    "the downtown markets on 2and saturday, the water show @ lake howard things that go on at the church's and community centers n parks. I love Winter Haven I can go on and on just being able to walk lake"
    22
    Flag
  • Martha K.
    "My neighborhood is nice and quiet and their isn’t any crimes they maintain over here but sometimes the neighbors can be loud."
    0
    Flag
  • Shelley P.
    "traffic can be a little heavy on the main roads n have a tendency to speed thru the side streets. But overall the traffic is decent."
    5
    Flag
  • John D. B.
    "very quiet,peaceful...laid back family oriented neighborhoods... older community.... spirit lake road can get busy with traffic noice.... best to live away from spirit lake road.."
    0
    Flag
  • Basapooh81
    "Winter Haven holds a lot of community events. They have something going on mostly every weekend in downtown winter Haven. Winter Haven has Legoland park and water park also. "
    10
    Flag
  • Cdixon496
    "Dog owners would like the fact that there is plenty of open fields and place for the dogs to run around."
    0
    Flag
  • Victoria W.
    "Some people don’t pick up after their dogs and some dog parks aren’t well kept. You can walk your dog easily with a lot of sidewalks and areas to walk to"
    14
    Flag
  • Mp19601
    "I just work around the area and every time i talk to sombody there nice and no complane for nothing...maybe i move in this area one fay"
    0
    Flag
  • Solomon G. .
    "Yes it’s nice area to be in no issues what so ever I like it very much . Can’t say anything bad nor good "
    1
    Flag
  • Norma.G
    "Well the associated need to be more strict,and severe with the Owners each property, how they park at the street, not at the grass, do not allow any car on the side of street,they should park at there own driveway ,and the driving at the neighbors area should be limited speed,driving to fast can cause hitting someone."
    0
    Flag
  • DR
    "Work is minutes away. Hardly ever go anywhere but Orlando as I don’t feel theres anything to do around here."
    0
    Flag
  • Ctjohns34
    "Neighbors complain about walking dogs, dogs only recently became allowed in this community and some neighbors resist change "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5392 CHANDLER DRIVE

  • What is 5392 CHANDLER DRIVE estimated to be worth?
    Trulia's estimated value for 5392 CHANDLER DRIVE in Winter Haven, FL is $349,500.
  • What is the price history for 5392 CHANDLER DRIVE?
    5392 CHANDLER DRIVE in Winter Haven, FL last sold for $349,000 in April 2026.
  • Is Winter Haven a buyer's or seller's market?
    Winter Haven is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Haven?
    The median sale price in Winter Haven is $258K. That is down $2.5K from the prior month.
  • Does 5392 CHANDLER DRIVE have air conditioning?
    Yes, 5392 CHANDLER DRIVE in Winter Haven, FL has air conditioning.
  • Does 5392 CHANDLER DRIVE have laundry facilities?
    Yes, 5392 CHANDLER DRIVE in Winter Haven, FL has laundry facilities.

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