1208 Winding Cypress Court
Kissimmee, FL 34746
- 5 beds
- 5 baths
- 2,572 sqft
- 7,144 sqft lot
- $217 per sqft
- 2003 build
- – on site
This fully upgraded 5-bedroom, 3-bathroom home in a gated resort community presents a highly profitable investment opportunity, generating $4,250 monthly in rental income. Previously a successful Airbnb, the property was always professionally cleaned and is now ready for continued rental. Inside, the home boasts a modern, open-concept layout, ideal for both relaxation and entertainment. The spacious living and dining areas flow seamlessly into a well-equipped kitchen with contemporary appliances, granite countertops, and a breakfast bar. The adjacent family room offers a cozy retreat, perfect for unwinding after a busy day. The master suite features a large walk-in closet and a luxurious en-suite bathroom with dual vanities, a soaking tub, and a separate shower. The remaining four bedrooms are generously sized and offers versatile living space for family, guests, or home offices. 3 full bathrooms and 2 half-baths are conveniently located throughout the home. Step outside to the private, screened-in saltwater pool area, requiring minimal maintenance for hassle-free enjoyment. The pool deck offers ample space for lounging, dining, or hosting gatherings, with peaceful water views that enhance the relaxing atmosphere. The property also includes a Tesla charger, adding modern convenience for electric vehicle owners. Security is enhanced with a state-of-the-art CCTV system, providing comprehensive coverage throughout the exterior of the property and the main living room. Located in a desirable gated community, this home offers easy access to major attractions, the best schools in te area, shopping, dining, and highways, making it an ideal choice for investors seeking a high-return rental property in a prime location.
Last checked:
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Last updated Mar 20, 2025
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MLS# O6259413 —
The Building
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Year Built:2003
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New Construction:false
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Architectural Style:Contemporary
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Construction Materials:Block
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Levels:Two
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Stories Total:2
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Roof:Shingle
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Foundation Details:Slab
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Building Area Total:3210
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Building Area Units:Square Feet
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Building Area Source:Public Records
Interior
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Interior Features:Ceiling Fan(s)
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Flooring:Carpet
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Fireplace:false
Room Dimensions
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Living Area:2572
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Living Area Units:Square Feet
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Living Area Source:Public Records
Location
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Directions:Continue on FL-408 W. Take I-4 Express and I-4 W to FL-535 S. Take exit 68 from I-4 W, Merge onto FL-408 W, keep left to stay on FL-408 W, Use the right 2 lanes to take exit 10A for I-4 E toward I-4 W/Tampa/Daytona Beach, Use any lane to take the Tampa W ramp, Merge onto I-4 W, Keep left at the fork to continue on I-4 Express, keep left to stay on I-4 Express, Merge onto I-4 W, Use the 2nd from the right lane to take exit 68 toward Kissimmee, Follow FL-535 S and N Poinciana Blvd to Winding Cypress Ct in Kissimmee, Use any lane to turn slightly left onto FL-535 S, turn right onto N Poinciana Blvd, Turn left onto Cumbrian Lakes Dr, Turn left onto Winding Cypress Ct.
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Latitude:28.273118
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Longitude:-81.465261
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Coordinates:-81.465261, 28.273118
The Property
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Parcel Number:362528127300011090
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Property Type:Residential
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Property Subtype:Single Family Residence
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Lot Features:Cul-De-Sac
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Lot Size Acres:0.16
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Lot Size Area:7144
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Lot Size SqFt:7144
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Lot Size Units:Square Feet
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Total Acres:0 to less than 1/4
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Zoning:KMPU
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Direction Faces:Southeast
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View:Water
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View:true
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Exterior Features:Rain Gutters
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Water Source:Public
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Road Surface Type:Paved
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Road Frontage Type:Street Paved
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Flood Zone Code:x
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Additional Parcels:false
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Homestead:false
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Lease Restrictions:false
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Land Lease:false
Listing Agent
- Contact info:
- Agent phone:
- (626) 638-5027
- Office phone:
- (407) 393-5901
Taxes
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Tax Year:2023
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Tax Lot:109
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Tax Block:1
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Tax Legal Description:CUMBRIAN LAKES RESORT PHASE 2 PB 13 PG 79-100 LOT 109
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Tax Book Number:13-79
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Tax Annual Amount:7400.05
Beds
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Bedrooms Total:5
Baths
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Total Baths:4
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Total Baths:5
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Full Baths:3
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Half Baths:2
The Listing
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Virtual Tour URL Unbranded:https://www.propertypanorama.com/instaview/stellar/O6259413
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Special Listing Conditions:None
Heating & Cooling
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Heating:Central
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Heating:true
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Cooling:Central Air
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Cooling:true
Utilities
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Utilities:BB/HS Internet Available
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Sewer:Public Sewer
Appliances
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Appliances:Dishwasher
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Laundry Features:Electric Dryer Hookup
Schools
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High School:Poinciana High School
The Community
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Subdivision Name:CUMBRIAN LAKES RESORT PH 2
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Senior Community:false
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Waterview:Pond
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Waterview:true
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Water Access:false
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Waterfront:false
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Pool Private:true
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Pool Features:Chlorine Free
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Pets Allowed:Yes
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Association:true
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Association Fee:175
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Association Fee Frequency:Monthly
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Association Fee Requirement:Required
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Monthly HOA Amount:175
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Ownership:Fee Simple
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Association Approval Required:false
Parking
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Garage:true
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Attached Garage:true
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Garage Spaces:2
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Carport:false
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Covered Spaces:2
Monthly cost estimate

Asking price
$559,000
Expense | Monthly cost |
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Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$2,993
|
Taxes | $616 |
Insurance | $153 |
HOA fees | $175 |
Utilities | $198 See report |
Total | $4,135/mo.* |
*This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Transit Score®
Provided by WalkScore® Inc.
Transit Score measures a location's access to public transit. It is based on nearby transit routes frequency, type of route (bus, rail, etc.), and distance to the nearest stop on the route. Transit Scores range from 0 (Minimal Transit) to 100 (Rider’s Paradise).
Soundscore™
Provided by HowLoud
Soundscore is an overall score that accounts for traffic, airport activity, and local sources. A Soundscore rating is a number between 50 (very loud) and 100 (very quiet).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
Date | Event | Source | Price | % Change |
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2/10/25
Feb 10, 2025
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Price Changed | STELLAR_MLS | $559,000 | -3.6% |
12/3/24
Dec 3, 2024
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Listed / Active | STELLAR_MLS | $580,000 | 103.5% (9.0% / YR) |
8/29/17
Aug 29, 2017
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Sold | STELLAR_MLS |