Winter Dr, Winter Haven, FL 33884
OFF MARKET

Winter Dr
Winter Haven, FL 33884

Cypress Gardens

    $256,500

    Trulia Estimate
    as of Aug 20, 2026
    Est. Refi. Payment $1,713/mo*
    Refinance Your Home

    $256,500

    Trulia Estimate
    as of Aug 20, 2026
    Est. Refi. Payment $1,713/mo*
    Refinance Your Home

    Home Value

    Trulia Estimate
    $257K
    Since last month
    Increased$2K (+0.7%)
    Since last year
    Decreased$9K (-3.4%)
    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 decreased by -17% in the last 10 years
    MonthEstimated value
    2026
    August 2026$257K
    July 2026$255K
    June 2026$261K
    May 2026$259K
    April 2026$259K
    March 2026$261K
    February 2026$257K
    January 2026$263K
    2025
    2024
    2023
    2022

    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
    110 Broward Dr, Winter Haven, FL
    0.07
    Single-Family Home
    $265,000
    06/15/26
    3
    2
    1,579
    101 Broward Dr, Winter Haven, FL
    0.11
    Single-Family Home
    $227,000
    05/04/26
    4
    2
    1,400
    110 DUVAL ROAD, Winter Haven, FL
    0.14
    Single-Family Home
    $268,000
    01/30/26
    2
    2
    1,512
    220 Escambia Dr SE, Winter Haven, FL
    0.14
    Single-Family Home
    $330,000
    08/27/25
    3
    2
    1,901
    220 ESCAMBIA DRIVE, Winter Haven, FL
    0.14
    Single-Family Home
    $330,000
    08/22/25
    3
    2
    1,701
    222 OKALOOSA DRIVE, Winter Haven, FL
    0.15
    Single-Family Home
    $270,000
    10/08/25
    2
    2.5
    1,835
    107 ALACHUA DRIVE, Winter Haven, FL
    0.15
    Single-Family Home
    $290,000
    12/10/25
    3
    2
    1,580
    237 OKALOOSA DRIVE, Winter Haven, FL
    0.17
    Single-Family Home
    $300,000
    06/18/26
    3
    2.5
    1,573
    237 Okaloosa Dr S, Winter Haven, FL
    0.17
    Single-Family Home
    $300,000
    06/22/26
    3
    2
    1,573
    81 DUVAL ROAD, Winter Haven, FL
    0.18
    Single-Family Home
    $381,000
    08/03/26
    4
    2
    1,893

    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
    149 OKALOOSA DRIVE, Winter Haven, FL 33884
    0.04
    $383,600
    4
    3
    2,581
    Off Market
    142 DRIVE, Winter Haven, FL 33884
    0.00
    $261,700
    3
    2
    1,639
    Off Market
    132 ALACHUA DRIVE, Winter Haven, FL 33884
    0.07
    $310,000
    3
    2
    2,466
    For Sale
    129 ALACHUA DRIVE, Winter Haven, FL 33884
    0.11
    $292,700
    5
    2
    1,750
    Off Market
    620 LAKE ELIZABETH DRIVE, Winter Haven, FL 33884
    0.14
    $266,000
    3
    2
    1,524
    Off Market
    348 Suwannee Rd, Winter Haven, FL 33884
    0.09
    $290,000
    3
    2
    1,778
    Off Market
    600 LAKE ELIZABETH DRIVE, Winter Haven, FL 33884
    0.15
    $222,900
    3
    2
    1,008
    Off Market
    105 SUWANNEE ROAD, Winter Haven, FL 33884
    0.15
    $317,800
    3
    2
    1,944
    Off Market
    107 ALACHUA DRIVE, Winter Haven, FL 33884
    0.15
    $290,000
    3
    2
    1,580
    Recently Sold
    110 DUVAL ROAD, Winter Haven, FL 33884
    0.14
    $268,000
    2
    2
    1,512
    Recently Sold
    106 DUVAL ROAD, Winter Haven, FL 33884
    0.14
    $278,100
    3
    2
    1,362
    Off Market
    229 ESCAMBIA DRIVE, Winter Haven, FL 33884
    0.13
    $416,800
    4
    2
    2,401
    Off Market

    Local Information

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

    About this House

    Winter Dr is in the Cypress Gardens neighborhood in Winter Haven, FL and in ZIP code 33884.
    Winter Dr, Winter Haven, FL 33884 is a unknown in Cypress Gardens. It is currently off market. The Trulia Estimate is $256,500, with a rent estimate of $1,920/month.

    Home Details for Winter Dr

    Property Information

    Property Type / Style
    Property Type: Unknown

    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

    Around this home

    Neighborhood Overview

    Cypress Gardens
    See Local Highlights
    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 "
      1
      Flag
    • 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."
      0
      Flag
    • 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"
      0
      Flag
    • 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."
      0
      Flag
    • 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."
      0
      Flag
    • Jessica S.
      "Very family friendly and a great place to raise kids. Neighbors have always been great and little to no criminal activity."
      1
      Flag
    • 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. "
      2
      Flag
    • Whmidas
      "Neighbors watch out for each other’s property when anyone is out of town. Good neighborhood watch with Ring."
      1
      Flag
    • 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"
      0
      Flag
    • 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. "
      0
      Flag
    • 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."
      2
      Flag
    • Wilmatoes66
      "It’s an older neighborhood and it’s quiet. It’s centrally located near restaurants And shopping. We have a charming neighborhood "
      1
      Flag
    • nreina1
      "i live here nd it's a beautiful area, convenient to everything and everywhere."
      0
      Flag
    • eliska o.
      "this has got to be the best of both worlds! country lake setting only one block from everything - everthing. "
      0
      Flag
    • 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. "
      2
      Flag

    LGBTQ Local Legal Protections

    Frequently asked questions about Winter Dr

    • What is Winter Dr estimated to be worth?
      Trulia's estimated value for Winter Dr in Winter Haven, FL is $256,500.
    • 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.
    • What do residents say about the Cypress Gardens neighborhood?
      Residents describe the Cypress Gardens neighborhood in Winter Haven, FL as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Cypress Gardens, Winter Haven.

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