414 Smiley Ct, Winter Haven, FL 33884
Property image
Property image
OFF MARKET

$431,400

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,930 sqft (on 0.39 acres)

414 Smiley Ct, Winter Haven, FL 33884

Cypress Gardens
Est. Refi. Payment $2,851/mo*
Refinance Your Home
Currently Off Market - Sold Nov 22, 2021 for $392,500

Home Value

Trulia Estimate
$431K
Since last month
Increased$1K (+0.3%)
Since last year
Increased$9K (+2.2%)
Since last sale
Increased$39K (+10%)
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 +96% in the last 10 years
MonthEstimated value
2026
August 2026$432K
August 2026$432K
July 2026$431K
June 2026$432K
May 2026$436K
April 2026$431K
March 2026$429K
February 2026$428K
January 2026$427K
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
0.04
Single-Family Home
$406,000
03/13/26
3
2
2,054
0.24
Single-Family Home
$480,000
11/13/25
3
2
2,251
0.06
Single-Family Home
$495,000
11/05/25
4
2
2,467
0.09
Single-Family Home
$362,450
05/15/26
4
2
2,113
0.32
Single-Family Home
$381,000
08/03/26
4
2
1,893
0.39
Single-Family Home
$380,000
01/09/26
3
2
1,826
0.30
Single-Family Home
$377,000
11/26/25
3
2
2,054
0.36
Single-Family Home
$392,000
04/20/26
3
2
2,378
0.13
Single-Family Home
$280,000
07/06/26
4
2
2,336
0.32
Single-Family Home
$319,000
05/22/26
3
2
2,070

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
0.03
$300,000
4
2
2,207
For Sale
0.07
$398,600
4
2
2,101
Off Market
0.06
$450,500
4
2
2,398
Off Market
0.05
$366,000
4
2
2,012
Off Market
0.06
$494,200
4
2
2,467
Off Market
0.04
$406,000
3
2
2,054
Recently Sold
0.09
$362,450
4
2
2,113
Recently Sold
0.10
$500,000
4
3
2,972
Off Market
0.12
$425,000
4
2.5
2,308
For Sale
0.07
$380,800
3
2
1,788
Off Market
0.13
$280,000
4
2
2,336
Recently Sold
0.09
$383,600
3
2
2,249
Off Market

Local Information

  • Map ViewExplore the area around 414 Smiley Ct.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1997
0.39 acre lot
1,930 sqft
$224/sqft
Garage

About this House

CREAM OF THE CROP!!! This home has it all! It's beautiful, charming, cozy, elegant and it's perfect for entertaining. Owners have exquisite taste and it shows in their choice of upgrades such as the porcelain (wood like) tile floors throughout the living room, kitchen, dining & foyer area, berber carpert in bedrooms, kitchen has Corian counter tops, outdoor kitchen/wet bar features granite tile & travertine. Sport swimming pool set up for volley ball. Huge back yard with plenty of land for more outdoor activities. Outdoor refrigerator stays. 2 Car Garage has been divided in two sections with one of the sections used as a theatre room where owners come home to relax, but, can be easily converted back to ALL GARAGE at buyer's request. Owner will gladly convert back. This home has so many extras you REALLY MUST come and see for yourself; you WILL NOT be disappointed!!!
414 Smiley Ct, Winter Haven, FL 33884 is a 3 bedroom, 2 bathroom, 1,930 sqft single-family home in Cypress Gardens, built in 1997. It last sold for $392,500 on Nov 22, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $431,400, with a rent estimate of $2,488/month.

Home Details for 414 Smiley Ct

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, LaminateGated Entry
Interior Details
AtticTypes of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Laundry Room, Master Bath, OfficeWet BarCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: StuccoFoundation Type: Retaining WallPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1997Year Updated: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Rental Terms, Policies & Fees

Furnished

Community

Units in Building: 1

Lot Information

Lot Area: 0.39 acres

Price and Tax history

DateEventPrice
Nov 20, 2024
Source: Stellar MLS #K4901541
ListingRemoved
$375,000
Nov 20, 2023
Source: Stellar MLS #K4901541
ListingRemoved
Nov 22, 2021
Source: N/A
Sold
$392,500
Oct 21, 2021
Source: Stellar MLS #K4901541
Pending
$375,000
Oct 18, 2021
Source: Stellar MLS #K4901541
Listed For Sale
$375,000

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 414 Smiley Ct

  • What is 414 Smiley Ct estimated to be worth?
    Trulia's estimated value for 414 Smiley Ct in Winter Haven, FL is $431,400.
  • What is the price history for 414 Smiley Ct?
    414 Smiley Ct in Winter Haven, FL last sold for $392,500 in November 2021.
  • 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 414 Smiley Ct have air conditioning?
    Yes, 414 Smiley Ct in Winter Haven, FL has air conditioning.
  • Does 414 Smiley Ct have a pool?
    Yes, 414 Smiley Ct in Winter Haven, FL has a pool.

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