302 Overlook Dr, Winter Haven, FL 33884
Property image
Property image
OFF MARKET

$560,000

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,735 sqft (on 0.45 acres)

302 Overlook Dr, Winter Haven, FL 33884

Cypress Gardens
Est. Refi. Payment $3,757/mo*
Refinance Your Home
Currently Off Market - Sold Apr 3, 2006 for $477,000

Home Value

Trulia Estimate
$560K
Since last month
Decreased$3K (-0.5%)
Since last year
Increased$2K (+0.3%)
Since last sale
Increased$81K (+16.9%)
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 +55% in the last 10 years
MonthEstimated value
2026
September 2026$558K
August 2026$561K
July 2026$557K
June 2026$562K
May 2026$568K
April 2026$567K
March 2026$565K
February 2026$558K
January 2026$559K
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
0.29
Single-Family Home
$663,000
09/23/25
4
3.5
3,203
0.14
Single-Family Home
$480,000
11/13/25
3
2
2,251
0.34
Single-Family Home
$478,000
06/09/26
4
2.5
2,571
0.21
Single-Family Home
$370,000
12/19/25
4
3
2,251
0.23
Single-Family Home
$385,000
01/26/26
4
3
2,503
0.31
Single-Family Home
$430,000
12/22/25
4
2.5
2,104
0.38
Single-Family Home
$495,000
11/05/25
4
2
2,467
0.30
Single-Family Home
$385,000
08/20/26
5
3
2,386
0.27
Single-Family Home
$392,000
04/20/26
3
2
2,378
0.54
Single-Family Home
$450,000
03/20/26
3
2
3,388

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
0.12
$430,000
3
2
2,251
For Sale
0.09
$462,700
5
3
2,416
Off Market
0.10
$471,400
4
3
2,509
Off Market
0.14
$481,600
3
2
2,251
Off Market
0.16
$533,000
5
3
3,306
Off Market
0.20
$377,000
3
2
2,054
Recently Sold
0.15
$335,600
4
2
1,865
Off Market
0.16
$320,800
4
2
1,850
Off Market
0.22
$399,999
3
2
2,167
For Sale
0.16
$367,600
5
3
2,416
Off Market
0.16
$392,200
3
2
1,726
Off Market
0.17
$326,200
4
2
1,850
Off Market

Local Information

  • Map ViewExplore the area around 302 Overlook Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1986
0.45 acre lot
3,735 sqft
$150/sqft
Garage

About this House

This secluded three story home on 1/2 acre is located on the shores of Lake Florence in the hub and excitement of the Cypress Gardens/Legoland business area. Owner will consider a lease purchase, short term lease or year's lease. Perfect home for active people as the skylights and windows make inside feel like outside all year long. This home should be move in ready by December 1st, 2020. This home can also be purchased. I am a real estate broker and the property is listed at $485,900.00.

Rent covers electric, trash, water, sewer, gas, pest control, lawn/lake landscape service, pets may be accepted on a case by case basis, all people residing in the home will sign the lease and have a background check if they are 18 years old or older. No subleases or additional tenants will be allowed without prior approval.
302 Overlook Dr, Winter Haven, FL 33884 is a 4 bedroom, 4 bathroom, 3,735 sqft single-family home in Cypress Gardens, built in 1986. It last sold for $477,000 on Apr 3, 2006. More recently, it was listed as a rental in October 2020 with an asking price of $3,200 per month. That rental listing was removed on January 8, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $560,000, with a rent estimate of $2,802/month.

Home Details for 302 Overlook Dr

Interior Features

Heating & Cooling
Heating: Forced Air, Electric, GasHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Interior Details
Types of Rooms: Walk In Closet
Appliances & Utilities
DryerWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: OtherFoundation Type: Retaining WallPatio
Parking & Garage
GarageParking Spaces: 3Parking: Garage Detached, Off Street

Property Information

Year Built
Year Built: 1986Year Updated: 1986
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.45 acres

Price and Tax history

DateEventPrice
May 11, 2021
Source: Stellar MLS #O5907606
ListingRemoved
Mar 19, 2021
Source: Stellar MLS #O5907606
Pending
$485,900
Jan 8, 2021
Source: N/A
ListingRemoved
Dec 7, 2020
Source: Stellar MLS #O5907606
Listed For Sale
$485,900
Nov 15, 2020
Source: N/A
PriceChange
$3,900
Price increased by 22%

Market trends in Winter Haven

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$258K
$2.5K
MoM
Sale-to-List Price
98.3%
0.1%
MoM
Price per sq ft
$160
$1
MoM
Available listings
771
7
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 isnโ€™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 otherโ€™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
    "Itโ€™s an older neighborhood and itโ€™s quiet. Itโ€™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 302 Overlook Dr

  • What is 302 Overlook Dr estimated to be worth?
    Trulia's estimated value for 302 Overlook Dr in Winter Haven, FL is $560,000.
  • What is the price history for 302 Overlook Dr?
    302 Overlook Dr in Winter Haven, FL last sold for $477,000 in April 2006.
  • 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 $258K. That is down $2.5K from the prior month.
  • Does 302 Overlook Dr have laundry facilities?
    Yes, 302 Overlook Dr in Winter Haven, FL has in-unit laundry.
  • How big is the lot at 302 Overlook Dr?
    The lot at 302 Overlook Dr in Winter Haven, FL is about 0.45 acres (19,649 sq ft).

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