416 Flagler Rd, Winter Haven, FL 33884
OFF MARKET

416 Flagler Rd
Winter Haven, FL 33884

Cypress Gardens
  • 4 Beds
  • 4 Baths
  • 2,801 sqft (on 0.34 acres)

$470,600

Trulia Estimate
as of Jun 6, 2026
Est. Refi. Payment $3,007/mo*

$470,600

Trulia Estimate
as of Jun 6, 2026
Est. Refi. Payment $3,007/mo*
4 Beds
4 Baths
2,801 sqft
(on 0.34 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

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 History for 416 Flagler Rd

DatePriceEventSource
09/29/2018$267,500Sold
N/A
09/03/2018$279,000PendingAgent Provided
08/20/2018$279,000Listed For SaleAgent Provided
12/28/2011$160,000Sold
N/A
10/11/2011$179,900PriceChange
Agent Provided
09/09/2011$199,900PriceChange
Agent Provided
08/11/2011$0Listed For SaleAgent Provided
11/23/2010$196,700Sold
N/A
07/31/2002$182,500Sold
N/A

Market trends in Winter Haven

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$253K
$1.63K
MoM
Sale-to-List Price
97.7%
0.7%
MoM
Price per sq ft
$160
$3
MoM
Available listings
771
17
MoM
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Property Tax and Assessment

Year2024
Tax$2,772
Assessment$387,625
Home facts updated by county records

Comparable Sales for 416 Flagler Rd

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
0.28
Single-Family Home
$500,000
08/25/25
5
4
2,880
0.39
Single-Family Home
$356,500
03/10/26
4
3.5
2,939
0.08
Single-Family Home
$370,000
07/08/25
3
2
1,893
0.15
Single-Family Home
$245,000
07/21/25
3
2
1,900
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
0.29
Single-Family Home
$449,900
06/24/25
4
2.5
2,226

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Assigned Schools

These are the assigned schools for 416 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 62 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

  • 27 % Say there are community events

  • 26 % 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 416 Flagler Rd

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Off Market Homes Near 416 Flagler Rd

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Homes for rent near 416 Flagler Rd

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416 Flagler Rd, Winter Haven, FL 33884 is a 4 bedroom, 4 bathroom, 2,801 sqft single-family home built in 1978. 416 Flagler Rd is located in Cypress Gardens, Winter Haven. This property is not currently available for sale. 416 Flagler Rd was last sold on Sep 29, 2018 for $267,500. The current Trulia Estimate for 416 Flagler Rd is $470,600.