417 Flagler Rd, Winter Haven, FL 33884
Property image
Property image
OFF MARKET

417 Flagler Rd
Winter Haven, FL 33884

Cypress Gardens
  • 4 Beds
  • 2.5 Baths
  • 2,784 sqft (on 0.45 acres)

$429,100

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $2,830/mo*

$429,100

Trulia Estimate
as of Aug 3, 2026
Est. Refi. Payment $2,830/mo*
4 Beds
2.5 Baths
2,784 sqft
(on 0.45 acres)

Local Information

  • Map ViewExplore the area around 417 Flagler Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1979
Lot Size
0.45 acres
Living Area
2,784 sqft
Price/Sqft
$154
Parking
Garage

About this House

The property you are inquiring about is located in Winter Haven, FL in the Valencia Wood Hills area of Polk County. Now here is an amazing story of a home that has been labeled "The Go To" family home. The reason because its easy access, has all the warmth, has the big pool area-big bedrooms, and all the bedrooms are together for the growing family. To gathering areas, to "let's eat" areas, and a ton of cozy nights by the fire! Keep the tradition going in this NEW PRICE-NEW LOOK-NEW DEAL home! PM me for for details.
417 Flagler Rd, Winter Haven, FL 33884 is a 4 bedroom, 3 bathroom, 2,784 sqft single-family home in Cypress Gardens, built in 1979. It last sold for $251,000 on Mar 10, 2020. It is currently off market. The Trulia Estimate is $429,100, with a rent estimate of $3,239/month.

Home Details for 417 Flagler Rd

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile
Interior Details
Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: StuccoFoundation Type: Retaining Wall
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1979Year Updated: 1979
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.45 acres

Price History for 417 Flagler Rd

DatePriceEventSource
03/10/2020$251,000Sold
N/A
02/04/2020$250,000PendingAgent Provided
01/21/2020$250,000PriceChange
Agent Provided
10/26/2019$299,900Listed For SaleAgent Provided
03/28/2003$180,000Sold
N/A
10/20/2000$178,000Sold
N/A
06/06/1994$140,000Sold
N/A

Market trends in Winter Haven

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$257K
Sale-to-List Price
98.2%
Price per sq ft
$158
$2
MoM
Available listings
767
3
MoM
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Property Tax and Assessment

Year2025
Tax$2,756
Assessment$399,216
Home facts updated by county records

Comparable Sales for 417 Flagler Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.06
Single-Family Home
$380,000
01/02/26
3
2
1,933
0.15
Single-Family Home
$690,000
07/07/26
3
3
2,588
0.19
Single-Family Home
$506,500
02/09/26
4
3.5
3,104
0.35
Single-Family Home
$339,000
06/29/26
4
2
1,777
0.26
Single-Family Home
$506,000
06/22/26
4
3.5
2,340
0.32
Single-Family Home
$405,000
10/31/25
3
2
2,056
0.49
Single-Family Home
$356,500
03/10/26
4
3.5
2,939
0.31
Single-Family Home
$390,000
05/29/26
3
2
2,035
0.44
Single-Family Home
$600,000
02/18/26
4
3
3,159
0.52
Single-Family Home
$300,000
11/24/25
4
4
3,042

Nearby homes

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Assigned Schools

These are the assigned schools for 417 Flagler Rd.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Neighborhood stats provided by third party data sources.

What Locals Say about Cypress Gardens

At least 63 Trulia users voted on each feature.
  • 88 % Say it's dog friendly

  • 84 % Say parking is easy

  • 81 % Say car is needed

  • 76 % Say yards are well-kept

  • 76 % Say it's quiet

  • 75 % Say there's holiday spirit

  • 56 % Say people would walk alone at night

  • 50 % Say kids play outside

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

  • 45 % Say neighbors are friendly

  • 42 % Say streets are well-lit

  • 35 % Say there are sidewalks

  • 30 % Say it's walkable to grocery stores

  • 30 % Say there's wildlife

  • 26 % Say there are community events

  • 25 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • 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 "
  • 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."
  • 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"
  • 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."
  • 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."
  • Jessica S.
    "Very family friendly and a great place to raise kids. Neighbors have always been great and little to no criminal activity."
  • Trulia User
    "I lived here my entire life. Love this area and all amenities available. People are friendly and it still has a small town feel. "
  • Whmidas
    "Neighbors watch out for each other’s property when anyone is out of town. Good neighborhood watch with Ring."
  • Timothy H.
    "Good restaurants and bars always something to do like bowl or mall or enjoy the downtown lifestyle. Lake everywhere get on a boat and enjoy"
  • Tyler S.
    "Nothing special. It's quiet, and safe with the occasional police car for small disturbances. Generally nice neighbors, not a lot of families moving in and out every other day. "
  • Eichhorst1986
    "looks good great neighbors and closer to most ever sour toy need. w are closer to Legoland and tough can see fireworks at night."
  • Wilmatoes66
    "It’s an older neighborhood and it’s quiet. It’s centrally located near restaurants And shopping. We have a charming neighborhood "
  • nreina1
    "i live here nd it's a beautiful area, convenient to everything and everywhere."
  • eliska o.
    "this has got to be the best of both worlds! country lake setting only one block from everything - everthing. "
  • S
    "Beautiful, Serene, Private and alot of greenery. Close to everything but far enough away from nonsense.....Safe, NO crime and very desirable for the family or couple looking for a peace of mind. "

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 417 Flagler Rd

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Off Market Homes Near 417 Flagler Rd

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