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

404 Flagler Rd
Winter Haven, FL 33884

Cypress Gardens
  • 3 Beds
  • 4 Baths
  • 2,400 sqft (on 0.34 acres)

$382,100

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $2,493/mo*
Refinance Your Home

$382,100

Trulia Estimate
as of Aug 19, 2026
Est. Refi. Payment $2,493/mo*
Refinance Your Home
3 Beds
4 Baths
2,400 sqft
(on 0.34 acres)

Home Value

Trulia Estimate
$382K
Since last month
Increased$3K (+0.8%)
Since last year
Increased$31K (+8.9%)
Since last sale
Increased$225K (+142.2%)
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 +106% in the last 10 years
MonthEstimated value
2026
August 2026$383K
July 2026$380K
June 2026$377K
May 2026$378K
April 2026$373K
March 2026$370K
February 2026$366K
January 2026$367K
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
114 Lake Otis Rd, Winter Haven, FL
0.13
Single-Family Home
$506,500
02/09/26
4
3.5
3,104
20 BREVARD DRIVE SE, Winter Haven, FL
0.19
Single-Family Home
$506,000
06/22/26
4
3.5
2,340
240 NASSAU ROAD, Winter Haven, FL
0.19
Single-Family Home
$390,000
05/29/26
3
2
2,035
425 FLAGLER ROAD, Winter Haven, FL
0.20
Single-Family Home
$380,000
01/02/26
3
2
1,933
128 LAKE RING DRIVE, Winter Haven, FL
0.18
Single-Family Home
$405,000
10/31/25
3
2
2,056
243 Lake Link Rd SE, Winter Haven, FL
0.29
Single-Family Home
$690,000
07/07/26
3
3
2,588
237 MANATEE ROAD, Winter Haven, FL
0.28
Single-Family Home
$500,000
08/25/25
5
4
2,880
419 PINELLAS ROAD, Winter Haven, FL
0.38
Single-Family Home
$395,000
08/14/26
4
2.5
2,248
1138 INTERLOCHEN BOULEVARD, Winter Haven, FL
0.40
Single-Family Home
$356,500
03/10/26
4
3.5
2,939
210 NASSAU ROAD, Winter Haven, FL
0.29
Single-Family Home
$475,000
04/28/26
3
2
1,987

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
92 LAKE OTIS ROAD, Winter Haven, FL 33884
0.03
$376,700
3
3
2,522
Off Market
112 LAKE OTIS ROAD, Winter Haven, FL 33884
0.11
$419,900
4
3
2,988
Off Market
247 LAKE RING DRIVE, Winter Haven, FL 33884
0.14
$491,300
4
3.5
2,834
Off Market
242 LAKE RING DRIVE, Winter Haven, FL 33884
0.11
$369,400
3
2
1,728
Off Market
236 HERNANDO ROAD, Winter Haven, FL 33884
0.10
$390,500
4
3
2,197
Off Market
116 LAKE RING DRIVE, Winter Haven, FL 33884
0.15
$434,700
3
2.5
3,454
Off Market
415 FLAGLER ROAD, Winter Haven, FL 33884
0.12
$360,700
3
2
1,893
Off Market
136 LAKE MARIAM ROAD SE, Winter Haven, FL 33884
0.14
$385,000
4
3
2,356
For Sale
20 BREVARD DRIVE SE, Winter Haven, FL 33884
0.19
$506,000
4
3.5
2,340
Recently Sold
240 NASSAU ROAD, Winter Haven, FL 33884
0.19
$390,000
3
2
2,035
Recently Sold
128 LAKE RING DRIVE, Winter Haven, FL 33884
0.18
$405,000
3
2
2,056
Recently Sold
130 PARK LANE, Winter Haven, FL 33884
0.19
$441,100
5
3.5
3,230
Off Market

Local Information

  • Map ViewExplore the area around 404 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
1978
Lot Size
0.34 acres
Living Area
2,400 sqft
Price/Sqft
$159
Parking
Garage

About this House

This single-family home is located at 404 Flagler Rd, Winter Haven, FL. 404 Flagler Rd is in the Cypress Gardens neighborhood in Winter Haven, FL and in ZIP code 33884. This property has 3 bedrooms, 4 bathrooms and approximately 2,400 sqft of floor space. This property has a lot size of 0.34 acres and was built in 1978.
404 Flagler Rd, Winter Haven, FL 33884 is a 3 bedroom, 4 bathroom, 2,400 sqft single-family home in Cypress Gardens, built in 1978. It last sold for $158,000 on Jan 24, 2014. It is currently off market. The Trulia Estimate is $382,100, with a rent estimate of $2,580/month.

Home Details for 404 Flagler Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Carpet, Linoleum Vinyl
Interior Details
Additional StorageStorage
Heating & Cooling
Air ConditioningCooling System: Central
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: StuccoFoundation Type: Retaining WallPatioPorch
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1978Year Updated: 1978
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price and Tax history

DateEventPrice
Jan 24, 2014
Source: Stellar MLS #P4625465
Sold
$158,000
Dec 5, 2013
Source: Agent Provided
PriceChange
$168,500
Price decreased by 4%
Oct 22, 2013
Source: Agent Provided
PriceChange
$174,900
Price increased by 3%
May 10, 2013
Source: Agent Provided
Listed For Sale
$169,900

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

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

Frequently asked questions about 404 Flagler Rd

  • What is 404 Flagler Rd estimated to be worth?
    Trulia's estimated value for 404 Flagler Rd in Winter Haven, FL is $382,100.
  • What is the price history for 404 Flagler Rd?
    404 Flagler Rd in Winter Haven, FL last sold for $158,000 in January 2014.
  • 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.
  • Does 404 Flagler Rd have air conditioning?
    Yes, 404 Flagler Rd in Winter Haven, FL has air conditioning.
  • How big is the lot at 404 Flagler Rd?
    The lot at 404 Flagler Rd in Winter Haven, FL is about 0.34 acres (14,810 sq ft).

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