$431,400
- 3 Beds
- 2 Baths
- 1,930 sqft (on 0.39 acres)
414 Smiley Ct, Winter Haven, FL 33884
Est. Refi. Payment $2,851/mo*
Refinance Your HomeCurrently Off Market - Sold Nov 22, 2021 for $392,500
Home Value
Trulia Estimate
$431KSince 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
| Month | Estimated 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
-- mins to
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
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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 |
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Exterior Home Features Roof: Shake ShingleDeckExterior: StuccoFoundation Type: Retaining WallPatioPorchSprinkler System |
Pool Pool |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
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Year Built Year Built: 1997Year Updated: 1997 |
Property Type / Style Property Type: Single Family HomeArchitecture: Other |
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Furnished |
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Units in Building: 1 |
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Lot Area: 0.39 acres |
Price and Tax history
| Date | Event | Price |
|---|---|---|
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 |
Apr 26, 2018 Source: N/A | Sold | $275,000 |
Mar 10, 2018 Source: Agent Provided | Listed For Sale | $275,000 |
Aug 24, 2006 Source: N/A | Sold | $305,000 |
Sep 1, 1999 Source: N/A | Sold | $164,000 |
Mar 24, 1997 Source: N/A | Sold | $25,000 |
Oct 8, 1996 Source: N/A | Sold | $20,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $3,877 | $346,004 |
Home facts updated by county records
Market trends in Winter Haven
Last updated July 2026
Avg. sale price
$260K
$3.28KMoM
Sale-to-List Price
98.4%
0.2%MoM
Price per sq ft
$161
$4MoM
Available listings
778
10MoM
Around this home
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.
LGBTQ Local Legal Protections
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.

