419 Flagler Rd, Winter Haven, FL 33884
OFF MARKET

419 Flagler Rd
Winter Haven, FL 33884

Cypress Gardens
  • 4 Beds
  • 3 Baths
  • 3,399 sqft (on 0.42 acres)

$614,300

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $3,992/mo*
Refinance Your Home

$614,300

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $3,992/mo*
Refinance Your Home
4 Beds
3 Baths
3,399 sqft
(on 0.42 acres)

Home Value

Trulia Estimate
$614K
Since last month
Increased$11K (+1.8%)
Since last year
Increased$42K (+7.3%)
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 +93% in the last 10 years
MonthEstimated value
2026
August 2026$613K
July 2026$611K
June 2026$602K
May 2026$594K
April 2026$592K
March 2026$585K
February 2026$575K
January 2026$579K
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
243 Lake Link Rd SE, Winter Haven, FL
0.13
Single-Family Home
$690,000
07/07/26
3
3
2,588
114 Lake Otis Rd, Winter Haven, FL
0.21
Single-Family Home
$506,500
02/09/26
4
3.5
3,104
425 FLAGLER ROAD, Winter Haven, FL
0.04
Single-Family Home
$380,000
01/02/26
3
2
1,933
304 LOCHEN CIRCLE SE, Winter Haven, FL
0.45
Single-Family Home
$600,000
02/18/26
4
3
3,159
20 BREVARD DRIVE SE, Winter Haven, FL
0.28
Single-Family Home
$506,000
06/22/26
4
3.5
2,340
316 LOCHEN CIR SE, Winter Haven, FL
0.39
Single-Family Home
$615,550
04/02/26
5
3.5
3,503
5 PEACHTREE LANE SE, Winter Haven, FL
0.43
Single-Family Home
$455,000
03/10/26
3
2.5
3,232
6 PEACHTREE LANE, Winter Haven, FL
0.42
Single-Family Home
$486,000
02/17/26
4
3
2,488
1138 INTERLOCHEN BOULEVARD, Winter Haven, FL
0.50
Single-Family Home
$356,500
03/10/26
4
3.5
2,939
237 MANATEE ROAD, Winter Haven, FL
0.39
Single-Family Home
$500,000
08/25/25
5
4
2,880

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
425 FLAGLER ROAD, Winter Haven, FL 33884
0.04
$380,000
3
2
1,933
Recently Sold
415 FLAGLER ROAD, Winter Haven, FL 33884
0.04
$360,700
3
2
1,893
Off Market
152 LAKE MARIAM ROAD SE, Winter Haven, FL 33884
0.07
$411,500
4
3
2,580
Off Market
136 LAKE MARIAM ROAD SE, Winter Haven, FL 33884
0.09
$385,000
4
3
2,356
For Sale
145 LAKE MARIAM ROAD, Winter Haven, FL 33884
0.10
$381,400
4
2.5
2,946
Off Market
252 LAKE LINK ROAD, Winter Haven, FL 33884
0.15
$429,600
4
3
2,206
Off Market
251 LAKE LINK ROAD, Winter Haven, FL 33884
0.16
$575,300
3
2
2,107
Off Market
260 LAKE LINK ROAD, Winter Haven, FL 33884
0.19
$453,200
4
3
2,822
Off Market
184 LAKE OTIS ROAD, Winter Haven, FL 33884
0.15
$450,000
4
3.5
2,921
For Sale
201 LAKE OTIS ROAD, Winter Haven, FL 33884
0.19
$386,600
3
2
1,893
Off Market
92 LAKE OTIS ROAD, Winter Haven, FL 33884
0.18
$376,700
3
3
2,522
Off Market
267 LAKE LINK ROAD, Winter Haven, FL 33884
0.24
$763,600
4
3
3,399
Off Market

Local Information

  • Map ViewExplore the area around 419 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
1993
Lot Size
0.42 acres
Living Area
3,399 sqft
Price/Sqft
$181
Parking
Garage

About this House

This single-family home is located at 419 Flagler Rd, Winter Haven, FL. 419 Flagler Rd is in the Cypress Gardens neighborhood in Winter Haven, FL and in ZIP code 33884. This property has 4 bedrooms, 3 bathrooms and approximately 3,399 sqft of floor space. This property has a lot size of 0.42 acres and was built in 1993.
419 Flagler Rd, Winter Haven, FL 33884 is a 4 bedroom, 3 bathroom, 3,399 sqft single-family home in Cypress Gardens, built in 1993. It is currently off market. The Trulia Estimate is $614,300, with a rent estimate of $3,487/month.

Home Details for 419 Flagler Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1993Year Updated: 1993
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.42 acres

Price and Tax history

YearProperty taxTax assessment
2025
$3,172
$584,006
Home facts updated by county records

Market trends in Winter Haven

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$260K
$3.28KMoM
Sale-to-List Price
98.4%
0.2%MoM
Price per sq ft
$161
$4MoM
Available listings
778
10MoM
Skip to last item
  • Results are loading
Skip to first item

Around this home

Neighborhood Overview

Cypress Gardens
See Local Highlights
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 "
    1
    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
  • 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
  • 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
  • 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
  • Jessica S.
    "Very family friendly and a great place to raise kids. Neighbors have always been great and little to no criminal activity."
    1
    Flag
  • 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. "
    2
    Flag
  • Whmidas
    "Neighbors watch out for each other’s property when anyone is out of town. Good neighborhood watch with Ring."
    1
    Flag
  • 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"
    0
    Flag
  • 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. "
    0
    Flag
  • 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."
    2
    Flag
  • Wilmatoes66
    "It’s an older neighborhood and it’s quiet. It’s centrally located near restaurants And shopping. We have a charming neighborhood "
    1
    Flag
  • nreina1
    "i live here nd it's a beautiful area, convenient to everything and everywhere."
    0
    Flag
  • eliska o.
    "this has got to be the best of both worlds! country lake setting only one block from everything - everthing. "
    0
    Flag
  • 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. "
    2
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

243 pet-friendly rentals in Winter Haven, FL

Explore by feature - Garage

179 rentals with a garage in Winter Haven, FL

Explore by feature - Air Conditioning

284 rentals with air conditioning in Winter Haven, FL

Explore by feature - Pool

158 rentals with a pool in Winter Haven, FL

Explore by feature - Washer/dryer

242 rentals with a washer/dryer in Winter Haven, FL

Explore by feature - Outdoor Space

66 rentals with an outdoor space in Winter Haven, FL

Homes for sale near 419 Flagler Rd

Skip to last item
Skip to first item

Off Market Homes Near 419 Flagler Rd

Skip to last item
Skip to first item

Frequently asked questions about 419 Flagler Rd

  • What is 419 Flagler Rd estimated to be worth?
    Trulia's estimated value for 419 Flagler Rd in Winter Haven, FL is $614,300.
  • 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 $260K. That is up $3.28K from the prior month.
  • What do residents say about the Cypress Gardens neighborhood?
    Residents describe the Cypress Gardens neighborhood in Winter Haven, FL as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Cypress Gardens, Winter Haven.
  • Does 419 Flagler Rd have a pool?
    Yes, 419 Flagler Rd in Winter Haven, FL has a pool.
  • How big is the lot at 419 Flagler Rd?
    The lot at 419 Flagler Rd in Winter Haven, FL is about 0.43 acres (18,513 sq ft).