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

$479,900

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 2,801 sqft (on 0.34 acres)

416 Flagler Rd, Winter Haven, FL 33884

Cypress Gardens
Est. Refi. Payment $3,153/mo*
Refinance Your Home
Currently Off Market - Sold Sep 29, 2018 for $267,500

Home Value

Trulia Estimate
$480K
Since last month
Increased$7K (+1.5%)
Since last year
Increased$24K (+5.3%)
Since last sale
Increased$212K (+79.3%)
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 +84% in the last 10 years
MonthEstimated value
2026
August 2026$480K
August 2026$480K
July 2026$473K
June 2026$473K
May 2026$471K
April 2026$465K
March 2026$468K
February 2026$458K
January 2026$457K
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
0.10
Single-Family Home
$506,500
02/09/26
4
3.5
3,104
0.17
Single-Family Home
$506,000
06/22/26
4
3.5
2,340
0.39
Single-Family Home
$356,500
03/10/26
4
3.5
2,939
0.56
Single-Family Home
$300,000
11/24/25
4
4
3,042
0.15
Single-Family Home
$380,000
01/02/26
3
2
1,933
0.29
Single-Family Home
$615,550
04/02/26
5
3.5
3,503
0.22
Single-Family Home
$390,000
05/29/26
3
2
2,035
0.22
Single-Family Home
$690,000
07/07/26
3
3
2,588
0.45
Single-Family Home
$395,000
08/14/26
4
2.5
2,248
0.54
Single-Family Home
$390,000
03/26/26
4
5
2,368

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
0.06
$385,000
4
3
2,356
For Sale
0.09
$428,200
4
3
2,988
Off Market
0.08
$367,100
3
2
1,893
Off Market
0.12
$457,500
5
3.5
3,230
Off Market
0.10
$376,500
3
3
2,522
Off Market
0.11
$388,200
4
2.5
2,946
Off Market
0.14
$388,600
3
2
1,893
Off Market
0.13
$409,900
4
3
2,580
Off Market
0.16
$529,800
4
4
3,557
Off Market
0.17
$325,000
5
3
2,579
For Sale
0.17
$506,000
4
3.5
2,340
Recently Sold
0.15
$380,000
3
2
1,933
Recently Sold

Local Information

  • Map ViewExplore the area around 416 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
2,801 sqft
Price/Sqft
$171
Parking
Garage

About this House

Located in the lovely established community of Valencia Wood Hills this large updated Pool home boasts 4 bedrooms and 4 full bathrooms with an office/bonus room. Featuring a modernized kitchen with granite counters, wood cabinetry, stainless steel appliances, and an eat-in bar area. The split floorplan gives the Primary Master Bedroom ample privacy and buyers are sure to appreciate the renovated master bathroom featuring travertine floors, walk-in shower, double vanity and gorgeous clawfoot soaking tub with adjoining walk-in closet with custom built-ins. Offering 2 living and dining areas, a wood burning fireplace, a dedicated office space, indoor laundry and an optional 2nd Master Bedroom this home provides ample space for entertaining and the option of having separate areas for adults, children and teens, guests, parents, or in-laws. This lovely home is built surrounding the beautiful outdoor space meant to invite you outside to the 15 x 30 solar heated swimming pool with pass through kitchen bar, television, pool bath, and adjacent fire pit. Outdoors no one will feel cramped on this .34acre lot with fully fenced backyard outfitted for cookouts, sunbathing, swimming, and evening fires. Call to schedule your appointment today!
416 Flagler Rd, Winter Haven, FL 33884 is a 4 bedroom, 4 bathroom, 2,801 sqft single-family home in Cypress Gardens, built in 1978. It last sold for $267,500 on Sep 29, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $479,900, with a rent estimate of $2,993/month.

Home Details for 416 Flagler Rd

Exterior Features

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

Property Information

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

Interior Features

Appliances & Utilities
DishwasherDisposalDryerMicrowave
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Laminate

Community

Units in Building: 1

Lot Information

Lot Area: 0.34 acres

Price and Tax history

DateEventPrice
Sep 29, 2018
Source: N/A
Sold
$267,500
Sep 3, 2018
Source: Agent Provided
Pending
$279,000
Aug 20, 2018
Source: Agent Provided
Listed For Sale
$279,000
Dec 28, 2011
Source: N/A
Sold
$160,000
Oct 11, 2011
Source: Agent Provided
PriceChange
$179,900
Price decreased by 10%

Market trends in Winter Haven

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$260K
$3.28K
MoM
Sale-to-List Price
98.4%
0.2%
MoM
Price per sq ft
$161
$4
MoM
Available listings
778
10
MoM

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

Frequently asked questions about 416 Flagler Rd

  • What is 416 Flagler Rd estimated to be worth?
    Trulia's estimated value for 416 Flagler Rd in Winter Haven, FL is $479,900.
  • What is the price history for 416 Flagler Rd?
    416 Flagler Rd in Winter Haven, FL last sold for $267,500 in September 2018.
  • 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 416 Flagler Rd have a pool?
    Yes, 416 Flagler Rd in Winter Haven, FL has a pool.
  • How big is the lot at 416 Flagler Rd?
    The lot at 416 Flagler Rd in Winter Haven, FL is about 0.34 acres (14,810 sq ft).

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