$559,000

1208 Winding Cypress Ct Kissimmee, FL 34746

$6,638
Closing credit¹
5 beds
3 full, 2 partial
2,572 sqft
0.2 acres
$217 / sqft
House

Property details

About 1208 Winding Cypress Ct

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.

Highlights

Home typeSingle Family Residence
HeatingCentral, Heat Pump
StatusActive
CoolingCentral Air
Size2,572 sqft
Lot size0.16 Acres
Year built2003
MLS #O6259413
Attached garage2 spaces
ViewWater
Private poolYes

Virtual tour

Summary

  • MLS Number: O6259413
  • MLS Name: MFRMLS
  • Office Name: KELLER WILLIAMS ADVANTAGE 2 REALTY
  • Office Phone: (407) 393-5901
  • Listing Agent: Maria Cuffaro

IDX Listings courtesy of Stellar MLS as distributed by MLS GRID.

All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS.

IDX Copyright 2025 My Florida Regional Multiple Listing Service DBA Stellar MLS. The real estate listing data marked with this icon comes from the IDX program of the Stellar MLS system. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided exclusively for consumers’ personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Properties displayed may be listed or sold by various participants in the MLS.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 4/3/2025, 11:49:50 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

Get an agent. Get a mortgage. Save big.¹

view of front of home with a front yard and a garage

$559,000

1208 Winding Cypress Ct

$6,638

closing credit¹

Sell your home with Rocket and save even more!

Seller rebate

0.5% sale price²

Price information

Property sales

DateEventPrice
Sep 20, 2022
Home Sold
$525,000
Sep 01, 2020
Home Sold
$289,000
Jun 06, 2013
Home Sold
$285,000
Mar 31, 2003
Home Sold
$274,900

Tax history

YearAssessmentProperty Tax
2023$422,100$7,400
2022$265,843$3,926
2021$258,100$3,926
2020$240,000$3,885
2019$233,100$4,144
2018$223,600$4,013
2017$212,300$4,013

History based on county public records data.

Nearby schools

4

Sunrise Elementary School

Public District PK-5

1.8 mi

1925 Ham Brown Rd

3

Pleasant Hill Elementary School

Public District PK-5

2.0 mi

1801 Jack Calhoun Dr

2

United Cerebral Palsy Osceola Charter School

Public Charter PK-5

2.8 mi

1820 Armstrong Blvd

School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.

All data from GreatSchools

Neighborhood

The neighbors living near this home have an average income of $49,898. Typical income of Kissimmee, FL residents is between $35k-100k annually. Residents typically live in married, with kids family. Most residents in this area have post secondary degree education.

How much money do the neighbors make?

31%
<35k
55%
35k-100k
10%
100k-200k
4%
200k+

What level of education do the neighbors have?

High School Diploma
Post Secondary Degree
Masters Degree

What types of families live nearby?

27%
Single, No Kids
14%
Single, with Kids
26%
Married, No Kids
33%
Married, with Kids

Are the neighbors home owners or renters?

Home Owners
Renters

How old are people in this area?

15%
<11 yrs old
10%
12-17 yrs old
25%
18-34 yrs old
42%
35-64 yrs old
8%
65+ yrs old

What do the neighbors do for fun?

  • Pro WrestlingPro Wrestling
  • MotocrossMotocross
  • College FootballCollege Football

Where do the neighbors shop?

  • Family DollarFamily Dollar
  • GameStopGameStop
  • Express/Express For MenExpress/Express For Men

Where do the neighbors go to eat?

  • Dominos PizzaDominos Pizza
  • SonicSonic
  • Cracker BarrelCracker Barrel

What do the neighbors drive?

  • FordFord
  • JeepJeep
  • KiaKia

What do the neighbors listen to?

  • New CountryNew Country
  • CountryCountry
  • Classic CountryClassic Country
All data provided by Home Junction and Claritas

Similar homes for sale

Frequently asked questions

About 1208 Winding Cypress Ct

This home is located at 1208 Winding Cypress Ct in Kissimmee, FL and zip code 34746 in the Cumbrian Lakes neighborhood. This 2,572 square foot home, which was built in 2003, sits on a 0.16 acre lot. Features: 5 bedrooms, 5 bathrooms. It has been listed on Rocket Homes since December 3, 2024 and is currently priced at $559,000.

In March 2025, from all listings sold in Kissimmee, FL there were more than 41 sold above asking price, over 279 sold below and more than 121 were sold right at the asked price. The number of listings in Kissimmee, FL increased by 8.2% between February and March 2025. The median list price of listings available in March 2025 was $364,982, while the average time on the real estate market was 80 days.

From Rocket Homes Real Estate and based on county public records data.

More resources