3550 Windham Dr, Holiday, FL 34691
Property image
Property image
OFF MARKET

$195,400

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,008 sqft

3550 Windham Dr, Holiday, FL 34691

Est. Refi. Payment $1,349/mo*
Refinance Your Home
Currently Off Market - Sold May 12, 2014 for $60,000

Home Value

Trulia Estimate
$195K
Since last month
Increased$1K (+0.5%)
Since last year
Decreased$4K (-2.1%)
Since last sale
Increased$135K (+225.7%)
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 +181% in the last 10 years
MonthEstimated value
2026
August 2026$195K
July 2026$194K
June 2026$199K
May 2026$200K
April 2026$200K
March 2026$198K
February 2026$195K
January 2026$199K
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
3521 Kimberly Oaks Dr, Holiday, FL
0.10
Single-Family Home
$144,200
08/05/26
2
2
988
3529 WINDHAM DRIVE, Holiday, FL
0.05
Single-Family Home
$185,000
10/03/25
2
1.5
848
3640 CHESWICK DRIVE, Holiday, FL
0.10
Single-Family Home
$200,000
09/24/25
2
2
1,024
3552 WESTCHESTER DRIVE, Holiday, FL
0.09
Single-Family Home
$175,000
02/26/26
2
1.5
848
4017 MOOG ROAD, Holiday, FL
0.14
Single-Family Home
$178,000
10/01/25
2
2
1,052
3706 CHESWICK DRIVE, Holiday, FL
0.13
Single-Family Home
$198,000
06/24/26
2
1.5
1,036
3909 SAIL DRIVE, New Port Richey, FL
0.26
Single-Family Home
$120,000
06/04/26
2
1.5
1,068
4116 OAKFIELD AVENUE, Holiday, FL
0.21
Single-Family Home
$110,000
02/12/26
3
3
1,484
3528 SHERYL HILL DRIVE, Holiday, FL
0.14
Single-Family Home
$222,000
11/14/25
2
2
1,068
3700 Kimberly Oaks Dr, Holiday, FL
0.18
Single-Family Home
$269,000
12/31/25
2
2
1,021

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
3546 CHESWICK DRIVE, Holiday, FL 34691
0.05
$241,600
2
2
1,042
Off Market
3529 WINDHAM DRIVE, Holiday, FL 34691
0.05
$180,400
2
1.5
848
Off Market
3530 WINDHAM DRIVE, Holiday, FL 34691
0.04
$284,900
3
2
1,189
Recently Sold
3539 BRADFORD DRIVE, Holiday, FL 34691
0.02
$202,100
2
1.5
988
Off Market
3622 CHESWICK DRIVE, Holiday, FL 34691
0.06
$217,200
3
2
1,232
Off Market
3553 BRADFORD DRIVE, Holiday, FL 34691
0.02
$214,900
2
2
1,042
Off Market
3625 WINDHAM DRIVE, Holiday, FL 34691
0.06
$225,000
3
1
1,200
Recently Sold
3623 CHESWICK DRIVE, Holiday, FL 34691
0.08
$210,200
2
2
956
Off Market
3535 CHESWICK DRIVE, Holiday, FL 34691
0.08
$214,500
3
2
1,036
Off Market
3522 WINDHAM DRIVE, Holiday, FL 34691
0.05
$225,200
4
1
1,118
Off Market
3524 CHESWICK DRIVE, Holiday, FL 34691
0.07
$235,000
3
2
1,258
Recently Sold
3552 WESTCHESTER DRIVE, Holiday, FL 34691
0.09
$175,000
2
1.5
848
Recently Sold

Local Information

  • Map ViewExplore the area around 3550 Windham Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1967
Living Area
1,008 sqft
Price/Sqft
$194
Parking
Garage

About this House

This single-family home is located at 3550 Windham Dr, Holiday, FL. 3550 Windham Dr is in Holiday, FL and in ZIP code 34691. This property has 2 bedrooms, 2 bathrooms and approximately 1,008 sqft of floor space. This property has a lot size of 5227 sqft and was built in 1967.
3550 Windham Dr, Holiday, FL 34691 is a 2 bedroom, 2 bathroom, 1,008 sqft single-family home built in 1967. It last sold for $60,000 on May 12, 2014. More recently, it was listed as a rental in April 2011 with an asking price of $675 per month. That rental listing was removed on June 17, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $195,400, with a rent estimate of $1,427/month.

Home Details for 3550 Windham Dr

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Appliances & Utilities
Refrigerator
Interior Details
Ceiling Fan

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: OtherPatioPorch
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1967Year Updated: 1967
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 5227 sqft

Price and Tax history

DateEventPrice
May 12, 2014
Source: N/A
Sold
$60,000
Feb 23, 2014
Source: Agent Provided
PriceChange
$59,900
Price decreased by 8%
Feb 11, 2014
Source: Agent Provided
PriceChange
$64,900
Price decreased by 3%
Jan 25, 2014
Source: Agent Provided
PriceChange
$66,990
Price decreased by 2%
Jan 15, 2014
Source: Agent Provided
PriceChange
$68,400
Price decreased by 2%

Market trends in Holiday

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$221K
$6.67KMoM
Sale-to-List Price
98.6%
Price per sq ft
$181
$6MoM
Available listings
313
17MoM

Around this home

What Locals Say about Holiday

At least 308 Trulia users voted on each feature.

  • 87 % Say car is needed

  • 85 % Say yards are well-kept

  • 82 % Say parking is easy

  • 82 % Say it's dog friendly

  • 72 % Say there's holiday spirit

  • 68 % Say there are sidewalks

  • 62 % Say kids play outside

  • 55 % Say it's quiet

  • 51 % Say neighbors are friendly

  • 45 % Say it's walkable to grocery stores

  • 42 % Say streets are well-lit

  • 42 % Say people would walk alone at night

  • 40 % Say they plan to stay for at least 5 years

  • 37 % Say there's wildlife

  • 30 % Say it's walkable to restaurants

  • 15 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Leano.loveslucy88
    "The Santa parade downtown NPR and the small community vibe is always a pleasant touch to the area, I plan on buying soon"
    0
    Flag
  • Heather Cook
    "Gas stations conveniently located. Stores are close by. That’s the only good thing really. Its really close to 19 so there’s a lot "
    1
    Flag
  • Taylor
    "Alligators can be found near almost any water source. This includes retention ponds. The school around here are also very poor, not good funding. Tons of homeless in the area, I would not trust them around my children."
    0
    Flag
  • Robbie Watson
    "The dog owners on my street walk their dogs at all hours, always pick up after their dogs and are all friendly"
    0
    Flag
  • Matthew_hartman
    "Multiple routes in and out of my neighborhood. Many easy ways to bypass busy roads except along the Anclote river"
    0
    Flag
  • Tanash Arthur
    "Criminals live around here, there are helicopters every here and there, we are surrounded by crack heads. At night it is very dangerous to be alone, always buy a camera for your home 😁"
    5
    Flag
  • Vivianwhitlow
    "Other dog owners are friendly. We love to chat with other dog owners. It helps us to be closer with our names."
    0
    Flag
  • Allan0151
    "Dogs are all well behaved. Lots of them being walked all the time. Just watch out for the gator that lives in the huge pond"
    0
    Flag
  • Trulia User
    "kid friendly area....lots of kids here from 4 years to 14 years ... very safe area....neighbors are nice... bus stop very accessible "
    1
    Flag
  • Trulia User
    "I'm live in a house temporarily till I find a permanent housing so it feels like home every one is friendly you don't hear dogs barking it is very quiet "
    0
    Flag
  • Trulia User
    "👍 mostly nice neighbors and neighborhood.too much fast traffic..not safe for little children to play out front."
    0
    Flag
  • Trulia User
    "Sidewalks are in most places throughout the neighborhood. Cars go too fast on the main thoroughfare. "
    0
    Flag
  • Trulia User
    "No public transportation for a mile. Most people would need to walk to the main thoroughfare (us 19). Uber or Lyft is the best option but most people do own a car."
    0
    Flag
  • PINEDAMAURO
    "Good Community, near of US 19 an SR54, whit restaurant, shop grocery’s near too. New main water aqueduct an light in the street. "
    1
    Flag
  • PINEDAMAURO
    "Greater sense of security, the street lights were changed, more neighbors with security cameras in their homes "
    6
    Flag
  • Victoria V.
    "My commute is pretty fare using my vehicle. I don’t know about public transportation. I use us 19 for going everywhere I need. "
    5
    Flag
  • Trulia User
    "they can walk their dog and the neighborhood is very pet friendly. people are very friendly as well.hope to talk to you soon"
    0
    Flag
  • Monica E.
    "Dog owners will like for cars to slow down the street while walking there dogs what dogs owner don’t like is that ppl need to puck there dog poop "
    3
    Flag
  • Brainsandbeauty
    "dog friendly but lots of barking in. the yards at all hours some people leave their dogs out for hours"
    1
    Flag
  • Michelle W.
    "It’s quiet and everyone minds their own business. I feel safe in this neighborhood. The only people to come on our street live here. "
    0
    Flag
  • Monica E.
    "It’s a very quiet area. Not too many kids. And. Residents are very nice. And a lot of shopping area "
    0
    Flag
  • Laura S.
    "I’m actually retired so don’t know bout the commute, but public transportation is very close walking distance "
    1
    Flag
  • Carolyn M. R.
    "Most people keep pets on leashes and abide by leash laws. People only pick up dog waste about 50 % of the time. Many stray and feral cats in this area."
    1
    Flag
  • Lala
    "I don’t commute, I work from home. I believe traffic is typical for rush hour time frames - never stopped completely."
    1
    Flag
  • Blah B.
    "I've lived in my neighborhood for working on two years. I have done nothing but deal with code enforcement and a couple nasty neighbors. it's not worth the hassle to have a nice house where have the house of your dreams because everyone around you will ruin it for you. I'm selling because of this. "
    16
    Flag
  • Carolyn M. R.
    "Schools are Title I. Couple of publuc parks and trails. A decent rec center nearby. No community pool."
    0
    Flag
  • Claudia W.
    "I’ve lived here for a year. I had great neighbors. Super friendly always there to help you if you need something. Lots of great kids in the neighborhood. Very friendly always talkative. This is a great family neighborhood. "
    7
    Flag
  • Brian C.
    "cant really recall any at all. new port richey has events that are family oriented so we go there sometimes"
    2
    Flag
  • Jane D.
    "There are dinners, dances, pool tournaments, shuffle board tournaments, exercise in Clubhouse and in pool. To mention anything more would take up the whole space. Nice community for year round living and a few days or months."
    2
    Flag
  • Glenn R.
    "close to all shopping and restaurants. close to bost ramps and fishing piers. beautiful sunsets over gulf of Mexico "
    1
    Flag
  • Haydee Irizarry
    "I've lived here for over 9 years. People are friendly and look out for each other. And it's improving the neighborhood is picking up."
    2
    Flag
  • Blueyes121081
    "Lots of young and middle school age children. Great community and easy access to grocery and other shopping. "
    0
    Flag
  • Carolslaven
    "Live in an over 55 community. Activities and good location . Maybe not the best pretty area but I like it. "
    0
    Flag
  • Flowerlady111
    "Well kept Tahitian gardens condos, family area.dollar store Aldi publix cvs Walgreens banks within 2 blocks. Beautiful pool.active community. Happy here for 13 years."
    1
    Flag
  • CJ
    "Quiet friendly neighbors and very little traffic. lived here 20 years and never had any issues with crime or neighbors. a great pllace to live."
    2
    Flag
  • OJ
    "This community helps the less fortunate. A lot of programs to volunteer and help in this community. Community is also growing rapidly. "
    0
    Flag
  • Johniesee
    "The young kids trick or treat in my subdivision. Most people decorate for the winter holidays. There are community yard sales twice a year. We have a community pool and a park like setting around the community lake. "
    2
    Flag
  • Destiny R.
    "A lot of kids in the Darlington rd area and a nice park nearby too. Some folks on dirt bikes drive through but it's otherwise quiet."
    1
    Flag
  • Mazarineskies
    "“keep what’s yours, lock your doors” signs on the main road. people lingering in the street at late hours into early morning. creepers lurking into car windows. "
    0
    Flag
  • Pamela
    "Don’t usually attend events there are not many events in the neighborhood very quiet place to live nice neighborhood "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 3550 Windham Dr

  • What is 3550 Windham Dr estimated to be worth?
    Trulia's estimated value for 3550 Windham Dr in Holiday, FL is $195,400.
  • What is the price history for 3550 Windham Dr?
    3550 Windham Dr in Holiday, FL last sold for $60,000 in May 2014.
  • Is Holiday a buyer's or seller's market?
    Holiday is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Holiday?
    The median sale price in Holiday is $221K. That is down $6.67K from the prior month.
  • Does 3550 Windham Dr have air conditioning?
    Yes, 3550 Windham Dr in Holiday, FL has air conditioning.
  • How big is the lot at 3550 Windham Dr?
    The lot at 3550 Windham Dr in Holiday, FL is about 0.12 acres (5,227 sq ft).

Explore by feature - Pet Friendly

94 pet-friendly rentals in Holiday, FL

Explore by feature - Garage

75 rentals with a garage in Holiday, FL

Explore by feature - Air Conditioning

128 rentals with air conditioning in Holiday, FL

Explore by feature - Pool

38 rentals with a pool in Holiday, FL

Explore by feature - Washer/dryer

97 rentals with a washer/dryer in Holiday, FL

Explore by feature - Outdoor Space

39 rentals with an outdoor space in Holiday, FL

Apartments for Rent

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Off Market Homes Near 3550 Windham Dr

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