305 Pilot Pl, Winter Haven, FL 33881
Property image
Property image
OFF MARKET

$235,600

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 1,839 sqft

305 Pilot Pl, Winter Haven, FL 33881

Est. Refi. Payment $1,598/mo*
Refinance Your Home
Currently Off Market - Sold Jan 7, 2020 for $145,000

Home Value

Trulia Estimate
$236K
Since last month
Increased$3K (+1.1%)
Since last year
Decreased$12K (-4.7%)
Since last sale
Increased$91K (+62.7%)
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 +58% in the last 10 years
MonthEstimated value
2026
August 2026$236K
August 2026$236K
July 2026$233K
June 2026$237K
May 2026$238K
April 2026$236K
March 2026$238K
February 2026$234K
January 2026$234K
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
70 Aviation Dr, Winter Haven, FL
0.05
Single-Family Home
$110,000
03/20/26
2
2
1,252
208 CALEB WAY, Winter Haven, FL
0.07
Single-Family Home
$263,000
06/03/26
3
2
1,725
122 JACE WAY, Winter Haven, FL
0.14
Single-Family Home
$245,000
08/07/26
3
2
1,405
15 Aviation Dr, Winter Haven, FL
0.08
Single-Family Home
$325,000
03/04/26
3
3
1,846
352 ALEXZANDER WAY, Winter Haven, FL
0.22
Single-Family Home
$269,900
07/17/26
4
2
1,867
2022 Marilyn Ave, Winter Haven, FL
0.19
Single-Family Home
$235,000
02/20/26
3
2
1,680
2013 MARILYN AVENUE, Winter Haven, FL
0.22
Single-Family Home
$315,000
04/21/26
3
2.5
1,942
2018 MARILYN AVENUE, Winter Haven, FL
0.19
Single-Family Home
$299,900
08/25/26
3
2
1,651
2018 NW Marilyn Ave, Winter Haven, FL
0.19
Single-Family Home
$299,900
08/26/26
3
2
1,651
2023 LEISURE DRIVE, Winter Haven, FL
0.24
Single-Family Home
$260,000
12/23/25
3
2
1,410

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
20 PILOT PLACE, Winter Haven, FL 33881
0.04
$298,900
3
2
1,654
Off Market
208 CALEB WAY, Winter Haven, FL 33881
0.07
$263,000
3
2
1,725
Recently Sold
10 PILOT PLACE, Winter Haven, FL 33881
0.07
$360,000
3
3.5
2,798
Recently Sold
101 AVIATION DRIVE, Winter Haven, FL 33881
0.03
$187,100
2
2
1,457
Off Market
208 AVIATION DRIVE, Winter Haven, FL 33881
0.04
$224,000
2
2
1,406
Off Market
122 JACE WAY, Winter Haven, FL 33881
0.14
$245,000
3
2
1,405
Recently Sold
2760 IDYLRIDGE WAY, Winter Haven, FL 33881
0.11
$236,500
3
2
1,540
Off Market
321 ALEXZANDER WAY, Winter Haven, FL 33881
0.14
$345,000
5
3
2,696
For Sale
2750 IDYLRIDGE WAY, Winter Haven, FL 33881
0.12
$222,200
3
1
1,008
Off Market
2048 LEISURE DRIVE, Winter Haven, FL 33881
0.18
$245,400
3
2
1,416
Off Market
2018 MARILYN AVENUE, Winter Haven, FL 33881
0.19
$299,900
3
2
1,651
Recently Sold
344 ALEXZANDER WAY, Winter Haven, FL 33881
0.20
$385,000
5
3
2,696
For Sale

Local Information

  • Map ViewExplore the area around 305 Pilot Pl.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1994
1,839 sqft
$128/sqft
Garage

About this House

REDUCED $10,000!!! FLY-IN COMMUNITY DIRECTLY ADJACENT TO WINTER HAVEN AIRPORT. Perfect spot for flying enthusiast with city-owned hangers available for rent. Subdivision has a community pool for the private use of homeowner's and their quests. Home is "move-in ready" and has many upgrades and updates completed by current owner. Features include: open Great Room plan; downstairs half-bath powder room; 15x10 screened lanai overlooking shady backyard; tile roof; 4 y.o. a/c unit; newer stainless kitchen appliances; Corian counter tops & sink in kitchen; natural gas range; tankless HWH; central vacuum system; dresser-style vanities in both full baths and over-sized single garage with extended area for storage & work bench. Home is an attached townhouse-style single family home (not a condo) so owner is responsible for their own exterior maintenance and yard care. HOA fee includes common area & pool maintenance, private streets care & irrigation. Even if you're not a pilot you'll enjoy this quiet, friendly community that's close to shopping, entertainment, several golf courses, medical centers and just minutes from I-4 for quick access to Tampa, Orlando and the attractions. Don't delay, you need to look at this value-packed home today!
305 Pilot Pl, Winter Haven, FL 33881 is a 3 bedroom, 3 bathroom, 1,839 sqft single-family home built in 1994. It last sold for $145,000 on Jan 7, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $235,600, with a rent estimate of $1,963/month.

Home Details for 305 Pilot Pl

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Types of Rooms: Walk In Closet, Dining RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: Stone, Stucco, WoodFoundation Type: Retaining WallPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Carport, Garage Attached

Property Information

Year Built
Year Built: 1994Year Updated: 1994
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 3236 sqft

Price and Tax history

DateEventPrice
Jan 7, 2020
Source: N/A
Sold
$145,000
Apr 10, 2016
Source: Agent Provided
ListingRemoved
$155,000
Nov 20, 2015
Source: Agent Provided
Listed For Sale
$155,000
Nov 2, 2015
Source: N/A
Sold
$140,000
Oct 10, 2015
Source: Agent Provided
Listed For Sale
$165,000

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

What Locals Say about Winter Haven

At least 800 Trulia users voted on each feature.

  • 83 % Say car is needed

  • 80 % Say parking is easy

  • 78 % Say yards are well-kept

  • 76 % Say it's dog friendly

  • 68 % Say there's holiday spirit

  • 64 % Say it's quiet

  • 61 % Say kids play outside

  • 49 % Say people would walk alone at night

  • 48 % Say there are sidewalks

  • 47 % Say they plan to stay for at least 5 years

  • 46 % Say streets are well-lit

  • 44 % Say neighbors are friendly

  • 43 % Say it's walkable to grocery stores

  • 32 % Say there's wildlife

  • 30 % Say it's walkable to restaurants

  • 24 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Cathyharris1222
    "Safe area for children and families "
    0
    Flag
  • Cocobrownie3
    "Freindly neighbors, Holloween is wonderful here, everyone loves to BBQ , and Santa Clause comes on Chismas Eve. Wonderful place to live. However, to schools are not so good. "
    0
    Flag
  • 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
  • Morgan Ivey-trask
    "Everyone is friendly and so nice. I like it here but I will be moving out soon to live in North Carolina to get my kids back and live a new life "
    2
    Flag
  • Madeline R
    "Its neighborly and quiet while still being close to the theme parks and airport. Ive lived here for 5 years and it was the best decision we made."
    0
    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
  • Z64p52x99r
    "I don’t go to the community events in the area I solely go to work and home I enjoy this peace in the neighborhood "
    0
    Flag
  • John Van Volkenburgh
    "Quick. No issues as long as you don’t work in Orlando or Tampa. Rural and central to the state. Small town. I’m "
    0
    Flag
  • Jenna Strickler
    "Food giveaways, law enforcement always circling/passing by Security feels safe Not the best neighborhood overall, but I have not had an issue since living here. "
    0
    Flag
  • Emily Torres
    "I’ve lived close to this area for 3 years now and worked there for a year and a half. Very nice area !"
    1
    Flag
  • Anonymous
    "You can walk your dogs with no problems. Many houses are fenced. Dogs will bark but not bite. Dogs ca"
    0
    Flag
  • Bianca Nieves
    "A lot of cats on the NE side of winter haven other than that winter haven lots of parks for children good schools "
    4
    Flag
  • Nicole Horton
    "I don’t feel safe for my 13 year old son to walk to the middle school by himself. I drive him and pick him up every day."
    0
    Flag
  • Chris M
    "There is a farmers market every weekend. A lot of community activities every weekend. Christmas parade happened a few weekends ago. "
    1
    Flag
  • Yoflyboys
    "NW Winter Haven has turned into a dump site. Homeless has taken over bus stop. Inman park and the surrounding areas."
    4
    Flag
  • Oo7legend
    "Great for families to live in and feel part of a community. Needs more retailers, restaurants and higher rated schools."
    30
    Flag
  • April_stylist
    "Quiet hard working families, no issues with traffic or safety we love this area. Very friendly folks"
    5
    Flag
  • Angmartinez05
    "Not much to do in terms of attractions but safe everywhere. 45 min from either Orlando or Tampa. Friendly people "
    0
    Flag
  • Katia S.
    "I live there for 3 years ,it’s quiet,I don’t have any complaint against it.I recommend it for a start,no to stay for a long time .I live close to the park.i like it and I feel safe."
    1
    Flag
  • Atrollergirl
    "My commute is nice. I live 1 mile from Wahneta and I'm located near Bartow, Eagle Lake, 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
  • Nakeem G.
    "My neighborhood in walking distance to a college, police station, farmers market, hair store, hospital/clinics and parks"
    11
    Flag
  • Joan
    "I live in this great neighborhood with great neighbors who get along. Quiet neighborhood. It feels safe."
    0
    Flag
  • Angela S.
    "Very busy front Street with big trucks daily passing by. Car speed a lot on the main road thru the area. "
    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
  • Nancy F.
    "I see people walking there dogs daily. we have a dog park in the community very nice area they are allowed off the leash in the fenced in area, they can run and play freely, very friendly area for them all maintained spayed often to keep fleas away.. pet friendly area. "
    1
    Flag
  • Jennycomp
    "There are no sidewalks or places to walk your dogs. They are forced to use people’s yards and they get upset."
    0
    Flag
  • Gina K.
    "Halloween is great here!!! Trick or treating is like a giant party and there’s so much fun going on. "
    0
    Flag
  • Shelley P.
    "the downtown markets on 2and saturday, the water show @ lake howard things that go on at the church's and community centers n parks. I love Winter Haven I can go on and on just being able to walk lake"
    22
    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
  • Shelley P.
    "traffic can be a little heavy on the main roads n have a tendency to speed thru the side streets. But overall the traffic is decent."
    5
    Flag
  • John D. B.
    "very quiet,peaceful...laid back family oriented neighborhoods... older community.... spirit lake road can get busy with traffic noice.... best to live away from spirit lake road.."
    0
    Flag
  • Basapooh81
    "Winter Haven holds a lot of community events. They have something going on mostly every weekend in downtown winter Haven. Winter Haven has Legoland park and water park also. "
    10
    Flag
  • Cdixon496
    "Dog owners would like the fact that there is plenty of open fields and place for the dogs to run around."
    0
    Flag
  • Victoria W.
    "Some people don’t pick up after their dogs and some dog parks aren’t well kept. You can walk your dog easily with a lot of sidewalks and areas to walk to"
    14
    Flag
  • Mp19601
    "I just work around the area and every time i talk to sombody there nice and no complane for nothing...maybe i move in this area one fay"
    0
    Flag
  • Solomon G. .
    "Yes it’s nice area to be in no issues what so ever I like it very much . Can’t say anything bad nor good "
    1
    Flag
  • Norma.G
    "Well the associated need to be more strict,and severe with the Owners each property, how they park at the street, not at the grass, do not allow any car on the side of street,they should park at there own driveway ,and the driving at the neighbors area should be limited speed,driving to fast can cause hitting someone."
    0
    Flag
  • DR
    "Work is minutes away. Hardly ever go anywhere but Orlando as I don’t feel theres anything to do around here."
    0
    Flag
  • Ctjohns34
    "Neighbors complain about walking dogs, dogs only recently became allowed in this community and some neighbors resist change "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 305 Pilot Pl

  • What is 305 Pilot Pl estimated to be worth?
    Trulia's estimated value for 305 Pilot Pl in Winter Haven, FL is $235,600.
  • What is the price history for 305 Pilot Pl?
    305 Pilot Pl in Winter Haven, FL last sold for $145,000 in January 2020.
  • 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 305 Pilot Pl have air conditioning?
    Yes, 305 Pilot Pl in Winter Haven, FL has air conditioning.
  • Does 305 Pilot Pl have a pool?
    Yes, 305 Pilot Pl in Winter Haven, FL has a pool.

Explore by feature - Pet Friendly

268 pet-friendly rentals in Winter Haven, FL

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Explore by feature - Pool

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Explore by feature - Outdoor Space

78 rentals with an outdoor space in Winter Haven, FL

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Off Market Homes Near 305 Pilot Pl

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