1663 Windsor Oak Ct, Kissimmee, FL 34744
OFF MARKET

1663 Windsor Oak Ct
Kissimmee, FL 34744

  • 3 Beds
  • 3 Baths
  • 1,406 sqft

$236,500

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $1,565/mo*
Refinance Your Home

$236,500

Trulia Estimate
as of Aug 9, 2026
Est. Refi. Payment $1,565/mo*
Refinance Your Home
3 Beds
3 Baths
1,406 sqft

Local Information

  • Map ViewExplore the area around 1663 Windsor Oak Ct.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Townhouse
Year Built
2000
Living Area
1,406 sqft
Price/Sqft
$168

About this House

This townhouse is located at 1663 Windsor Oak Ct, Kissimmee, FL. 1663 Windsor Oak Ct is in Kissimmee, FL and in ZIP code 34744. This property has 3 bedrooms, 3 bathrooms and approximately 1,406 sqft of floor space. This property has a lot size of 1306 sqft and was built in 2000.
1663 Windsor Oak Ct, Kissimmee, FL 34744 is a 3 bedroom, 3 bathroom, 1,406 sqft townhouse built in 2000. It last sold for $96,000 on Jul 20, 2015. It is currently off market. The Trulia Estimate is $236,500, with a rent estimate of $1,989/month.

Home Details for 1663 Windsor Oak Ct

Interior Features

Heating & Cooling
Heating: Other, ElectricAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet
Interior Details
Number of Rooms: 4
Appliances & Utilities
DryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: OtherFoundation Type: FootingPatioPorch

Property Information

Year Built
Year Built: 2000Year Updated: 2000
Property Type / Style
Property Type: TownhouseArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 1306 sqft

Price History for 1663 Windsor Oak Ct

DatePriceEventSource
07/20/2015$96,000Sold
N/A
02/22/2015$102,000ListingRemovedAgent Provided
12/06/2014$102,000Listed For SaleAgent Provided
02/10/2011$51,000Sold
N/A
12/04/2010$59,900PriceChange
Agent Provided
12/03/2010$0Listed For SaleAgent Provided
10/11/2010$0ListingRemovedAgent Provided
09/26/2010$59,900PriceChange
Agent Provided
09/24/2010$0Listed For SaleAgent Provided
05/08/2007$182,000Sold
N/A
03/10/2004$102,000Sold
N/A
04/26/2000$93,900Sold
N/A

Market trends in Kissimmee

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$376K
Sale-to-List Price
97.5%
0.2%MoM
Price per sq ft
$205
$1MoM
Available listings
3078
68MoM
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Property Tax and Assessment

Year2025
Tax$3,003
Assessment$198,300
Home facts updated by county records

Comparable Sales for 1663 Windsor Oak Ct

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1642 WINDSOR OAK COURT, Kissimmee, FL
0.02
Townhouse
$265,000
10/06/25
3
3
1,406
1651 WINDSOR OAK COURT, Kissimmee, FL
0.03
Townhouse
$264,000
08/14/25
3
2
1,240
1621 EMILY COURT, Kissimmee, FL
0.07
Townhouse
$250,500
12/29/25
3
2
1,263
1611 MOHEGAN BOULEVARD, Kissimmee, FL
0.39
Townhouse
$369,900
12/15/25
3
2.5
2,016
2051 CYPRESS BAY BOULEVARD, Kissimmee, FL
1.12
Townhouse
$265,000
12/18/25
3
2.5
1,382
2026 CYPRESS BAY BOULEVARD, Kissimmee, FL
1.13
Townhouse
$280,000
07/28/26
3
2.5
1,382
2116 JEREMIAH WAY, Kissimmee, FL
1.23
Townhouse
$270,000
07/28/26
3
2.5
1,382
2087 Cypress Bay Blvd, Kissimmee, FL
1.08
Townhouse
$310,000
04/13/26
3
3
1,807
1670 HOUSTON STREET, Kissimmee, FL
1.37
Townhouse
$359,900
10/23/25
3
2.5
1,452
1680 HOUSTON STREET, Kissimmee, FL
1.37
Townhouse
$359,900
10/23/25
3
2.5
1,452

Nearby homes

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Assigned Schools

These are the assigned schools for 1663 Windsor Oak Ct.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Kissimmee

At least 2333 Trulia users voted on each feature.

  • 79 % Say it's dog friendly

  • 76 % Say car is needed

  • 75 % Say there are sidewalks

  • 73 % Say parking is easy

  • 70 % Say there's holiday spirit

  • 69 % Say yards are well-kept

  • 66 % Say it's quiet

  • 61 % Say kids play outside

  • 60 % Say streets are well-lit

  • 56 % Say people would walk alone at night

  • 53 % Say they plan to stay for at least 5 years

  • 49 % Say it's walkable to grocery stores

  • 46 % Say there's wildlife

  • 43 % Say it's walkable to restaurants

  • 40 % Say neighbors are friendly

  • 30 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • James King
    "A lot of walking paths"
    0
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  • Trulia User
    "I live in this neighborhood for 22 years and love it. I love that there are many store conveniently located to the home."
    0
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  • Trulia User
    "Good place to live very quiet,clean and safe enough to live "
    0
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  • Taryn Hall
    "There are a lot of vacation homes here and people speed thru the neighborhood and park along the main entrance street, crowding up the busiest road space near the park "
    0
    Flag
  • Deyline Jusino
    "Great city to live in. Places are close, no need to travel far. I recommend Kissimmee to everyone. Great schools. "
    0
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  • Nelines Montero
    "In an overall sense, it’s a safe neighborhood. Good for every type of family: single parent, two-parents, and even same sex parents. "
    0
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  • Trulia User
    "Lived here 18 years. Seen the community grow. The neighborhood has evolved into somewhat quiet since a lot of the kids have grown up. Nice calm peaceful "
    0
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  • Trulia User
    "Good schools in the area. Family friendly neighborhoods with lots of parks and walking trails for families with and without pets. "
    0
    Flag
  • Laura Annunziata
    "It’s Celebration we have many events for locals and visitors, tree lighting , parades , music festivals etc "
    0
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  • Terry Vivar
    "My community has great access to good schools. Everything is conveniently located near by like grocery stores and shopping centers. The people in the neighborhood are very polite and welcoming. "
    0
    Flag
  • Yesica Mejias
    "I work 10 minutes away. In the morning with traffic it takes me 14 minutes. I have everything close by. Shopping mall’s are just 3 minutes away and some walking distance."
    0
    Flag
  • Sara Colon
    "They have a golf cart and they have fun celebrating Christmas parade, 4th of July and too many events! This Community is for Senior"
    0
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  • Rachelbaby78
    "Safe enough. Never really had any problems in this area. School bus rides are too long as k-8 is districted to a school that is 40 minutes away. At least the high school is closer. "
    1
    Flag
  • Rachelbaby78
    "Schools are zoned oddly here. We are 15 minutes from the first elementary and middle school we were zoned to but then got rezoned for a k-8 school 40 minutes away. The bus rides are ridiculously long… "
    0
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  • Trulia User
    "Lived here for 16 years. Been very pleasant and quiet neighborhood. Neighbors are friendly but not nosy. "
    0
    Flag
  • Brittany Shay
    "It’s extremely quiet for how close we are to 192. Everyone is very nice and maintain their homes pretty well."
    0
    Flag
  • Katthehuman08
    "Great community that comes together, believes in respecting thy neighbors, working together so that many achieve successness"
    0
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  • Leslie Hasenkampf
    "We enjoy our neighborhood because it has a community feel, is friendly, and very conveniently located. "
    0
    Flag
  • Ydvargas
    "The problem in the neighborhood is about dog owner, they didn’t pick it up the pupu is around in everywhere"
    0
    Flag
  • Sarah Burgos
    "It’s a great location for commuters- closely accesible to the hwy, 192, and many businesses locally. Only 30 min to Disney and Universal, and only 1 hr to the ocean or Florida springs and vast nature. "
    0
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  • CORTESJOSH
    "Close to turnpike, 192, narcossee are all minutes away. Close to MCO airport, about 15 mins away from I4"
    0
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  • Kelly Zimmerman
    "The traffic is outrageous. It took us 20+ mins to go a few miles. Completely takes away from what should feel like a nice area. "
    0
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  • Paola Castellano
    "Love Kissimmee I have been leaving for 8 years the only thing the owner forget to pick up the caca from de dog"
    0
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  • Leslie Hasenkampf
    "We are generally happy with our neighborhood. However, we are planning to move within the next year because another area better fits our needs. There is absolutely nothing wrong with our current home."
    0
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  • Stephanie Jones
    "Keep a close eye on everything kids pets and personal items, some seems friendly others don’t so just be aware of surroundings "
    0
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  • 9ytjsjgz45
    "Nice place and quiet for living . I have everythibg close to my house like supermarket , Pharmacy, places to est and take a walk "
    0
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  • Leslie Hasenkampf
    "This is a pet friendly area. There are people out with their pets throughout the day. Pet owners seem to love and care for their pets. Each neighborhood has a nice dog park which allows people and pets to meet. "
    0
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  • Mg.machado2212
    "I like my neighborhood. It’s so quiet and peaceful. The people are so friendly and welcoming. I want move but near to this place."
    0
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  • Sarah B
    "If it’s local, commuting is a breeze. If you have to get on the hwy or drive up/down Narcoose during rush hour, it is a parking lot. Also tolls here add up and they are really expensive. "
    0
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  • 29tnhsh9bh
    "Not a lot of poop bag posts to pick up your dogs fecal matter so they can put more of them around the area for dog owners "
    0
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  • Robin Moore
    "It’s Quiet Here and Relaxing zi find that there are ample places to visit and also shop I’m here just recently retired and searching for a home here next to my Family I feel safe here"
    0
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  • Cynthia Maslar
    "They would like the lake front park where they can take there dogs and walk them there’s a bunch of space and grass area "
    0
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  • cristel lozada
    "Is good to begin with or arrive from another city but may be move to a less tourist area . Its high ways are busy most of the time . Tráfic"
    0
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  • Mennat_allah
    "98% of the people take care of their homes and they maintain it well … North Point gated community and people are friendly "
    0
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  • Carlos Santiago
    "Clean, quiet and close to a lot good stuff for visiting for the weekend with the family and friends "
    0
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  • Mimi soliman
    "Very friendly neighbors easy to live here kind of hard to access considering all school traffic feels very safe here "
    0
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  • Kissimmee resident
    "Nothing happens here, other than people breaking into your car or hearing about a shooting that just happened. "
    29
    Flag
  • Jt6zfqy7vv
    "In the two years that I have lived here, I have not seen any special events happening. If there are events, there should be more advertising of them. "
    6
    Flag
  • Leslie Hasenkampf
    "Dog owners would like that most of the neighborhoods have dog parks, and there are plenty of sidewalks for walking. The downside is there are many careless drivers and it can be noisy."
    0
    Flag
  • Leslie Hasenkampf
    "We have food trucks a few times a month and meet and greets from time to time. 😊 The neighborhood is also very welcoming to newcomers. Everyone feels at home. "
    0
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Homes for sale near 1663 Windsor Oak Ct

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Off Market Homes Near 1663 Windsor Oak Ct

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Frequently asked questions about 1663 Windsor Oak Ct

  • What is 1663 Windsor Oak Ct estimated to be worth?
    Trulia's estimated value for 1663 Windsor Oak Ct in Kissimmee, FL is $236,500.
  • What is the price history for 1663 Windsor Oak Ct?
    1663 Windsor Oak Ct in Kissimmee, FL last sold for $96,000 in July 2015.
  • Is Kissimmee a buyer's or seller's market?
    Kissimmee is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Kissimmee?
    The median sale price in Kissimmee is $376K. That is roughly unchanged from the prior month.
  • Does 1663 Windsor Oak Ct have air conditioning?
    Yes, 1663 Windsor Oak Ct in Kissimmee, FL has air conditioning.
  • Does 1663 Windsor Oak Ct have laundry facilities?
    Yes, 1663 Windsor Oak Ct in Kissimmee, FL has in-unit laundry.