415 Smiley Ct, Winter Haven, FL 33884
OFF MARKET

415 Smiley Ct
Winter Haven, FL 33884

Cypress Gardens
  • 3 Beds
  • 2 Baths
  • 2,420 sqft (on 0.32 acres)

$421,200

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $2,710/mo*

$421,200

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $2,710/mo*
3 Beds
2 Baths
2,420 sqft
(on 0.32 acres)

Local Information

  • Map ViewExplore the area around 415 Smiley Ct.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 415 Smiley Ct, Winter Haven, FL. 415 Smiley Ct is in the Cypress Gardens neighborhood in Winter Haven, FL and in ZIP code 33884. This property has 3 bedrooms, 2 bathrooms and approximately 2,420 sqft of floor space. This property has a lot size of 0.32 acres and was built in 1995.
415 Smiley Ct, Winter Haven, FL 33884 is a 3 bedroom, 2 bathroom, 2,420 sqft single-family home in Cypress Gardens, built in 1995. It last sold for $275,000 on Apr 7, 2025. More recently, it was listed as a rental in October 2025 with an asking price of $2,800 per month. That rental listing was removed on November 26, 2025. It is currently off market. The Trulia Estimate is $421,200, with a rent estimate of $2,624/month.

Home Highlights

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

Home Details for 415 Smiley Ct

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet

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: 1995Year Updated: 1995
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.32 acres

Price History for 415 Smiley Ct

DatePriceEventSource
11/26/2025$2,750ListingRemovedStellar MLS #S5132827
11/01/2025$2,750PriceChange
Stellar MLS #S5132827
11/01/2025$430,000PriceChange
Stellar MLS #S5128812
10/18/2025$2,800Listed For RentStellar MLS #S5132827
10/18/2025$434,000PriceChange
Stellar MLS #S5128812
10/17/2025$442,000PendingToActiveStellar MLS #S5128812
10/04/2025$442,000PendingStellar MLS #S5128812
09/23/2025$2,750ListingRemovedStellar MLS #S5132827
09/19/2025$442,000PriceChange
Stellar MLS #S5128812
09/03/2025$429,000PriceChange
Stellar MLS #S5128812
09/03/2025$2,750PriceChange
Stellar MLS #S5132827
08/25/2025$2,950Listed For RentStellar MLS #S5132827
08/18/2025$2,950ListingRemovedStellar MLS #S5132827
08/15/2025$2,950Listed For RentStellar MLS #S5132827
08/15/2025$434,000PriceChange
Stellar MLS #S5128812
08/13/2025$438,000PriceChange
Stellar MLS #S5128812
07/14/2025$440,000PriceChange
Stellar MLS #S5128812
06/27/2025$450,000PriceChange
Stellar MLS #S5128812
06/13/2025$454,000Listed For SaleStellar MLS #S5128812
04/07/2025$275,000Sold
N/A
03/23/2010$215,000Sold
N/A
03/22/1995$22,500Sold
N/A

Market trends in Winter Haven

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$256K
$2.83K
MoM
Sale-to-List Price
98.1%
0.4%
MoM
Price per sq ft
$159
$1
MoM
Available listings
767
7
MoM
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Property Tax and Assessment

Year2025
Tax$2,666
Assessment$382,122
Home facts updated by county records

Comparable Sales for 415 Smiley Ct

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.02
Single-Family Home
$406,000
03/13/26
3
2
2,054
0.09
Single-Family Home
$495,000
11/05/25
4
2
2,467
0.14
Single-Family Home
$362,450
05/15/26
4
2
2,113
0.38
Single-Family Home
$392,000
04/20/26
3
2
2,378
0.19
Single-Family Home
$425,000
07/28/25
4
2
2,087
0.29
Single-Family Home
$270,000
07/30/25
3
2
1,628
0.27
Single-Family Home
$480,000
11/13/25
3
2
2,251
0.34
Single-Family Home
$377,000
11/26/25
3
2
2,054
0.42
Single-Family Home
$295,000
11/07/25
3
2
1,747
0.45
Single-Family Home
$326,000
10/21/25
3
2
1,858

Nearby homes

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Assigned Schools

These are the assigned schools for 415 Smiley Ct.
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. "

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Homes for sale near 415 Smiley Ct

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Off Market Homes Near 415 Smiley Ct

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