Not every house needs to be brand new to be the right house. Sitting on a quiet cul-de-sac in Shadow Bay, this 4-bedroom, 3-bath pool home has more than 2,000 square feet, a layout with personality, and plenty of room for the next owner to make it their own. Vaulted ceilings, exposed wood beams and an open staircase give the main living spaces architectural character you simply don’t find in every home. The first floor includes the primary suite plus an additional bedroom and full bath, while two more bedrooms and a third bath are upstairs, creating a flexible layout for family, guests or a home office. Out back, a large screened-in pool and covered patio take center stage, with a fenced backyard and plenty of space to enjoy Florida living. The home also offers a two-car garage, new fencing installed in 2022 and a new roof installed in 2020, taking two meaningful exterior items off the future to-do list. And a refreshingly low HOA of only $305 per year. The location puts you close to the best of Kissimmee, with easy access to US-192, shopping, dining, schools and major roadways, plus Walt Disney World and Orlando’s attractions within easy reach. This isn't a cookie-cutter renovation where someone else chose every finish for you. It's a home with good bones, real square footage and plenty of potential for someone ready to bring their own vision to it. Update a little at a time or come in with a plan and make it entirely your own. Either way, the space, pool, layout and location give you a solid place to start.
Single-familyProperty Type
1984Year Built
10,542 sq ftLot Size
$173Price/Sq.Ft.
$25/moHOA Dues
2 car garageParking
Listed by Chad Vaughan• REAL BROKER, LLC
Contact: 855-450-0442
Bought with Cody Sullivan• KELLER WILLIAMS REALTY AT THE PARKS
Est. $2,685 per month, based on comparable rentals
Redfin agents who toured
Close to US-192
2 years ago• May not reflect the current state of the home
Damecia Ross
Redfin Associate agent
Sale and tax history for 2704 Winding Ridge Ave S
Sale History
Tax History
Date
Event
Price
Stellar MLS as Distributed by MLS Grid #O6447274
Oct 29, 2026
Sold
$350,000
$173/sq ft
Oct 21, 2026
Pending
—
Oct 5, 2026
Listed
$365,000
$181/sq ft
Stellar MLS as Distributed by MLS Grid #O6217494
Nov 14, 2024
Listing Removed
—
STELLARMLS #6192559
Apr 3, 2024
Rental Removed
$2,467
$1/sq ft
Apr 2, 2024
Listed for Rent
$2,467
$1/sq ft
Public Records
Mar 17, 2022
Sold
$381,000
$189/sq ft
Stellar MLS as Distributed by MLS Grid #S5061997
Mar 14, 2022
Sold
$361,000
$179/sq ft
Feb 1, 2022
Pending
—
Jan 28, 2022
Listed
$334,500
$166/sq ft
DON'T MISS OPPORTUNITY TO PREVIEW THIS 2 STORY HOME IN THE WELL MAINTAINED COMMUNITY OF SHADOW BAY. LOCATED ON QUIET CUL-DE-SAC. THIS 4 BEDROOM/3 BATH HOME HAS SPACIOUS LIVING ROOM AND DINING ROOM, KITCHEN WITH BREAKFAST AREA, MASTER BEDROOM AND BATH, ALONG WITH SECOND BEDROOM IS LOCATED ON FIRST FLOOR. .. SECOND FLOOR HAS TWO BEDROOMS AND BATH. 10X42 PORCH OVERLOOKS LARGE SCREENED POOL, AND PRIVATE BACK YARD WHICH IS FENCED. POOL AND DECK WERE RESURFACED IN 2021, ALONG WITH ROOF REPLACEMENT. HOME IS LOCATED CLOSE TO MAJOR ROADWAYS, SCHOOLS, AND SHOPPING AT THE LOOP. THE HOA TAKES EXTREMELY GOOD CARE OF THE COMMON AREAS IN THIS COMMUNITY. MULTIPLE OFFERS WILL BE SUBMITTED TO SELLERS TUESDAY MORNING FEB 1ST 2022.
Public Records
Dec 17, 1990
Sold
$124,000
$61/sq ft
Public Records
Nov 1, 1984
Sold
$85,800
$42/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$5,759 (+9.1%)
$85,000 + $230,800
$315,800
2024
$5,278 (+2.6%)
$85,000 + $230,800
$315,800
2023
$5,143 (+373.7%)
$75,000 + $228,800
$303,800
2022
$1,086 (+8.4%)
$50,000 + $243,300
$293,300
2021
$1,002 (+1.5%)
2020
$988 (+2.7%)
2019
$961 (+2.1%)
2018
$941 (+1.3%)
2017
$930 (+2.8%)
2016
$904 (−1.4%)
2015
$917 (+0.8%)
2014
$910 (+1.7%)
2013
$895 (−3.1%)
2012
$924
$14,900 + $69,300
$84,200
Public record
Public record
Zoning
Beds
4
Baths
3
Stories
2
Lot width
78 ft.
Lot depth
135 ft.
Lot size
10,542
Year renovated
1984
Sq. Ft.
2,021
Year built
1984
Style
Single Family Residential
County
Osceola County
APN
172529213600010620
Parking Spaces
2
Basement
No
Accessible
No
HOA Dues
$252 /month
Garage
Yes
Features
Pool
Last updated by owner on Apr 24, 2022.
RA-2
Single Family Residential District
The single family residential zoning districts are primarily intended to meet the single family housing needs of the community. All four districts may be used to implement the Single Family Low Density Residential SF-LDR future land use designation.
Lot Features: In County, Landscaped, Sidewalk, Paved
Lot Size Acres: 0.24
Road Surface Type: Asphalt
Road Responsibility: Public Maintained Road
Lot Size Square Meters: 979
Building Information
MFR_BuildingAreaTotalSrchSqM: 270.63
Financial
Tax Information
Tax Annual Amount: $5,759
Tax Year: 2025
Lease / Rent Details
Lease Restrictions YN: 0
Utilities
Utility Information
Water Source: Public
Sewer: Public Sewer
Utilities: BB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Water Connected
Location
Multi-Family Financial Information
Total Annual Fees: $305
Total Monthly Fees: $25.42
Multi-Unit Information
Unit Number YN: 0
Furnished: Unfurnished
HOA Information
Association Name: Shadow Bay Community Association/Ms. Le Nguyen
Has HOA
MFR_Association2YN: 0
Association Fee Requirement: Required
Association Approval Required Y/N: 0
Monthly HOA Amount: 25.42
Association Fee: $305
Association Fee Frequency: Annually
Association Fee Includes: Common Area Taxes
School Information
Elementary School: Kissimmee Elem
Middle Or Junior High School: Kissimmee Middle
High School: Osceola High School
Location Information
Directions: From US-192/W Vine St, head south on N Thacker Ave. Turn left into Shadow Bay, then turn left at the end of the street onto Winding Ridge Ave S. Follow Winding Ridge to the cul-de-sac. 2704 Winding Ridge Ave S will be on the left.
Community Information
Community Features: Deed Restrictions, Sidewalks, Street Lights
Pets Allowed: Yes
Public facts
Beds: 4
Baths: 3.0
Sq. Ft.: 2,021
Stories: 2.0
Parking Spaces: 2
Basement: No
Accessible: No
Lot Size: 10,542 square feet
Style: Single Family Residential
Year Built: 1984
Year Renovated: 1984
County: Osceola County
APN: 172529213600010620
HOA Dues: $252/month
Garage: Yes
Features: Pool
Home facts updated by owner on Apr 24, 2022
Other
Miscellaneous Information
Third Party YN: 1
Listing Information
Attribution Contact: 855-450-0442
Previous Status: Pending
Backups Requested YN: 0
Listing Date Information
Days to Contract: 13
Status Contractual Search Date: 2026-10-29
Listing Price Information
Calculated List Price By Calculated Sq Ft: 180.60
Green Information
Green Verification Count: 0
Direction Faces: North
Home Information
Living Area: 2021
Living Area Units: Square Feet
Living Area Source: Public Records
Living Area Meters: 187.76
Building Area Total: 2913
Building Area Units: Square Feet
Building Area Source: Public Records
Foundation Details: Slab
Levels: One
Security Features: Smoke Detector(s)
Around this home
Schools
Kissimmee Elementary School
Public PreK-5 • Assigned • 0.7mi
5/10
Kissimmee Middle School
Public 6-8 • Assigned • 0.5mi
4/10
Osceola High School
Public 9-12 • Assigned • 1.8mi
3/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
9/10 Heat Factor
7 days above 108° expected this year, 23 days in 30 years
9/10 Wind Factor
99% chance of strong winds in next 30 years
1/10 Air Factor
0 unhealthy days expected this year, 0 days in 30 years
Provided by First Street
Historical weather
Kissimmee, FL • 34741
Average low and high temperatures (°F)
69
49
75
54
80
60
83
65
89
72
91
74
92
76
90
76
88
74
83
69
78
60
74
56
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
95/ 100
Exceptional sunlight
Sunscore
This home receives average direct sun exposure in Kissimmee. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
10.8 hrs
8 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$359,000 – $434,000
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Based on information submitted to the MLS GRID as of Sat Oct 31 2026. 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.