415 FLAGLER ROAD, Winter Haven, FL 33884
OFF MARKET

415 FLAGLER ROAD
Winter Haven, FL 33884

Cypress Gardens
  • 3 Beds
  • 2 Baths
  • 1,893 sqft (on 0.33 acres)

$362,700

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $2,380/mo*
Refinance Your Home

$362,700

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $2,380/mo*
Refinance Your Home
3 Beds
2 Baths
1,893 sqft
(on 0.33 acres)

Home Value

Trulia Estimate
$363K
Since last month
Increased$2K (+0.7%)
Since last year
Decreased$5K (-1.4%)
Since last sale
Decreased$7K (-2%)
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 +152% in the last 10 years
MonthEstimated value
2026
August 2026$363K
July 2026$360K
June 2026$356K
May 2026$354K
April 2026$362K
March 2026$358K
February 2026$360K
January 2026$359K
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
425 FLAGLER ROAD, Winter Haven, FL
0.08
Single-Family Home
$380,000
01/02/26
3
2
1,933
240 NASSAU ROAD, Winter Haven, FL
0.29
Single-Family Home
$390,000
05/29/26
3
2
2,035
128 LAKE RING DRIVE, Winter Haven, FL
0.30
Single-Family Home
$405,000
10/31/25
3
2
2,056
22 LAKE LINK DRIVE SE, Winter Haven, FL
0.37
Single-Family Home
$339,000
06/29/26
4
2
1,777
73 LAKE LINK CIRCLE SE, Winter Haven, FL
0.52
Single-Family Home
$358,000
11/17/25
3
2
1,964
210 NASSAU ROAD, Winter Haven, FL
0.39
Single-Family Home
$475,000
04/28/26
3
2
1,987
204 S LAKE MARIAM DRIVE, Winter Haven, FL
0.50
Single-Family Home
$380,000
01/09/26
3
2
1,826
58 LAKE LINK CIRCLE SE, Winter Haven, FL
0.53
Single-Family Home
$399,000
06/29/26
3
2
2,000

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
136 LAKE MARIAM ROAD SE, Winter Haven, FL 33884
0.07
$385,000
4
3
2,356
For Sale
425 FLAGLER ROAD, Winter Haven, FL 33884
0.08
$380,000
3
2
1,933
Recently Sold
152 LAKE MARIAM ROAD SE, Winter Haven, FL 33884
0.09
$411,500
4
3
2,580
Off Market
145 LAKE MARIAM ROAD, Winter Haven, FL 33884
0.10
$383,800
4
2.5
2,946
Off Market
92 LAKE OTIS ROAD, Winter Haven, FL 33884
0.15
$376,700
3
3
2,522
Off Market
112 LAKE OTIS ROAD, Winter Haven, FL 33884
0.16
$421,400
4
3
2,988
Off Market
201 LAKE OTIS ROAD, Winter Haven, FL 33884
0.17
$388,700
3
2
1,893
Off Market
130 PARK LANE, Winter Haven, FL 33884
0.18
$471,600
5
3.5
3,230
Off Market
252 LAKE LINK ROAD, Winter Haven, FL 33884
0.18
$429,600
4
3
2,206
Off Market
236 HERNANDO ROAD, Winter Haven, FL 33884
0.21
$393,300
4
3
2,197
Off Market
251 LAKE LINK ROAD, Winter Haven, FL 33884
0.20
$575,300
3
2
2,107
Off Market

Local Information

  • Map ViewExplore the area around 415 FLAGLER ROAD.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1977
Lot Size
0.33 acres
Living Area
1,893 sqft
Price/Sqft
$192
Parking
2 Car Garage
HOA
$18/Monthly

About this House

NEW ROOF BEFORE CLOSING!! Charming 3-Bed, 2-Bath Pool Home in Peaceful Family-Friendly Neighborhood Welcome to your dream home! This beautifully maintained 1,893 sqft 3-bedroom, 2-bathroom pool home is nestled in a serene and private neighborhood, great for executives and seeking tranquility and comfort. Key Features: • Spacious Living: Enjoy an open floor plan that seamlessly connects the living, dining, and kitchen areas, creating an inviting space wonderful for entertaining and family gatherings. • Modern Kitchen: The heart of the home boasts a beautifully remodeled kitchen, featuring an extra-large island and stunning level 5 granite countertops. Wonderful for culinary enthusiasts and those who love to host. • Screened-In Pool: Relax and unwind in the comfort of your own screened-in pool area, for enjoying the Florida weather without the hassle of bugs. The spacious deck provides plenty of room for outdoor dining and lounging. • Comfort & Convenience: Benefit from a brand-new AC unit, ensuring year-round comfort. The 2-car garage provides ample space for vehicles and storage. • Generous Bedrooms: Three well-appointed bedrooms provide comfortable living spaces, with the master suite has a private retreat. Don’t miss this incredible opportunity to own a piece of paradise. Schedule your private showing today and experience the charm and comfort of this exceptional home!
415 FLAGLER ROAD, Winter Haven, FL 33884 is a 3 bedroom, 2 bathroom, 1,893 sqft single-family home in Cypress Gardens, built in 1977. It last sold for $370,000 on Jul 8, 2025 (3% below the $379,900 asking price). It is currently off market. The Trulia Estimate is $362,700, with a rent estimate of $2,341/month.
Last check for updates: about 4 hours ago
Listed by Steven Koleno, (804) 656-5007
BEYCOME OF FLORIDA LLC, (804) 656-5007
Bought with: Neville Clarke, (754) 244-2170, IMPACT REALTY TAMPA BAY, (813) 321-1200
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6288796
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 415 FLAGLER ROAD

Interior Features

Interior Details
Number of Rooms: 6Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1893 Square Feet
Appliances & Utilities
Utilities: Cable Available, Underground UtilitiesAppliances: Cooktop, Dishwasher, Dryer, Microwave, Range, Range Hood, Refrigerator, WasherDishwasherDryerLaundry: In Garage,InsideMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Door: Outdoor Shower, Sliding DoorsFlooring: Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Tile
View
No ViewView: Lake

Exterior Features

Exterior Home Features
Roof: ShingleExterior: Irrigation System, Outdoor Shower, Private MailboxFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Pool
Pool: Screen EnclosurePool
Frontage
Road Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 239

Property Information

Year Built
Year Built: 1977
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: BlockNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 262827000000042760

Price & Status

Price
List Price: $379,900
Status Change & Dates
Off Market Date: Mon May 05 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: WINTER HAVENCommunity: VALENCIA WOOD HILLS

Building

Building Area
Building Area: 2498 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: NoneHOA Name: Marie GainerHOA Phone: 863-271-0756Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $18/Monthly

Lot Information

Lot Area: 0.33 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Assumable, Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6288796Water ViewWater View: LakeShowing Considerations: See RemarksShowing Requirements: Call Owner, See RemarksUniversal Property Id: US-12105-N-262827000000042760-R-N

Price and Tax history

DateEventPrice
Jul 8, 2025
Source: Stellar MLS #O6288796
Sold
$370,000
May 5, 2025
Source: Stellar MLS #O6288796
Pending
$379,900
Mar 11, 2025
Source: Stellar MLS #O6288796
Listed For Sale
$379,900
Feb 28, 2025
Source: Stellar MLS #A4621547
ListingRemoved
$384,900
Jan 3, 2025
Source: Stellar MLS #A4621547
PriceChange
$384,900
Price decreased by 1%

Market trends in Winter Haven

Last updated July 2026
Buyer'sMarketSeller'sMarket
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

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 415 FLAGLER ROAD

  • What is 415 FLAGLER ROAD estimated to be worth?
    Trulia's estimated value for 415 FLAGLER ROAD in Winter Haven, FL is $362,700.
  • What is the price history for 415 FLAGLER ROAD?
    415 FLAGLER ROAD in Winter Haven, FL last sold for $370,000 in July 2025.
  • 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 415 FLAGLER ROAD have air conditioning?
    Yes, 415 FLAGLER ROAD in Winter Haven, FL has air conditioning.
  • Does 415 FLAGLER ROAD have a pool?
    Yes, 415 FLAGLER ROAD in Winter Haven, FL has a pool.

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