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

408 Smiley Ct
Winter Haven, FL 33884

Cypress Gardens
  • 5 Beds
  • 2 Baths
  • 2,695 sqft (on 0.29 acres)

$463,800

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $2,971/mo*

$463,800

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $2,971/mo*
5 Beds
2 Baths
2,695 sqft
(on 0.29 acres)

Local Information

  • Map ViewExplore the area around 408 Smiley Ct.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Short Sale..Spacious pool home located in Lake Mariam Hills. Split floor plan offers; 5 bedrooms and 2 bathrooms plus formal dining room, bonus room, family room and utility room. Features vaulted ceilings with fireplace. Hardwood flooring with ceramic tile and carpet in bedrooms. Kitchen has breakfast bar and closet pantry. Luxury master suite. Screen enclosed solar heated pool. Attached 3 car garage. Situated in a great SE Winter Haven community.
408 Smiley Ct, Winter Haven, FL 33884 is a 5 bedroom, 2 bathroom, 2,695 sqft single-family home in Cypress Gardens, built in 1996. It last sold for $225,000 on Aug 3, 2016. It is currently off market. The Trulia Estimate is $463,800, with a rent estimate of $2,918/month.

Home Highlights

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

Home Details for 408 Smiley Ct

Interior Features

Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Hardwood
Interior Details
Types of Rooms: Walk In Closet, Dining RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Stucco, BrickFoundation Type: Retaining WallGardenPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Carport, Garage Attached

Property Information

Year Built
Year Built: 1996Year Updated: 1996
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Price History for 408 Smiley Ct

DatePriceEventSource
08/03/2016$225,000Sold
Stellar MLS #P4709658
05/18/2016$225,000PendingAgent Provided
03/25/2016$225,000Listed For SaleAgent Provided
04/19/2013$226,000Sold
Stellar MLS #P4622908
02/06/2013$224,900PriceChange
Agent Provided
01/30/2013$244,900PriceChange
Agent Provided
10/27/2012$249,000Listed For SaleAgent Provided
08/29/2012$299,950ListingRemovedN/A
06/09/2012$299,950Listed For SaleN/A
04/05/2012$279,000ListingRemovedAgent Provided
03/23/2011$279,000PriceChange
Agent Provided
06/12/2010$299,000PriceChange
Agent Provided
02/27/2010$329,000Listed For SaleAgent Provided
03/16/2004$235,000Sold
N/A
03/02/2000$186,000Sold
N/A
12/18/1998$184,500Sold
N/A
03/25/1996$164,000Sold
N/A
07/20/1995$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$3,176
Assessment$386,051
Home facts updated by county records

Comparable Sales for 408 Smiley Ct

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.02
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
0.14
Single-Family Home
$425,000
07/28/25
4
2
2,087
0.22
Single-Family Home
$270,000
07/30/25
3
2
1,628
0.09
Single-Family Home
$406,000
03/13/26
3
2
2,054
0.30
Single-Family Home
$377,000
11/26/25
3
2
2,054
0.36
Single-Family Home
$280,000
05/04/26
4
3
1,900
0.35
Single-Family Home
$295,000
11/07/25
3
2
1,747
0.40
Single-Family Home
$326,000
10/21/25
3
2
1,858
0.40
Single-Family Home
$330,000
08/27/25
3
2
1,901

Nearby homes

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Assigned Schools

These are the assigned schools for 408 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. "

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 408 Smiley Ct

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Off Market Homes Near 408 Smiley Ct

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