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.
Property Details
Price:
$365,000
MLS #:
O6447274
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
SHADOW BAY UNIT 2
Neighborhood:
34741kissimmeedowntowneast
Listed Date:
Oct 5, 2026
Finished Sq Ft:
2,021
Total Sq Ft:
2,913
Lot Size:
10,542 sqft / 0.24 acres (approx)
Year Built:
1984
See this Listing
Schools
Elementary School:
Kissimmee Elem
Middle School:
Kissimmee Middle
High School:
Osceola High School
Interior
Appliances
Dishwasher, Microwave, Range, Refrigerator
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Flooring
Tile
Heating
Central, Electric
Interior Features
High Ceilings, Primary Bedroom Main Floor, Thermostat
Laundry Features
Inside
Levels
One
Exterior
Attached Garage YN
1
Community Features
Deed Restrictions, Sidewalks
Construction Materials
Block
Covered Spaces
2
Direction Faces
North
Exterior Features
Private Yard, Sidewalk, Sliding Doors
Fencing
Fenced
Garage Spaces
2
Lot Features
In County, Landscaped, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener
Patio And Porch Features
Covered, Rear Porch
Roof
Shingle
Security Features
Smoke Detector(s)
Financial
HOA Fee
$305
HOA Fee Frequency
Annually
HOA Includes
Common Area Taxes
HOA Name
Shadow Bay Community Association/Ms. Le Nguyen
HOA Phone
407-847-9003
Tax Year
2025
Taxes
$5,759
Map
Community
- Address2704 WINDING RIDGE AVENUE S KISSIMMEE FL
- SubdivisionSHADOW BAY UNIT 2
- CityKISSIMMEE
- CountyOsceola
- Zip Code34741
Subdivisions in KISSIMMEE
- Association of Poinciana Villages
- BELLALAGO
- BELLAVIDA PH 01
- COMPASS BAY
- EAGLE LAKE PH 1
- EAST PALM RESORT CONDO
- MargaritaVille
- POINCIANA NBRHD 5 NORTH VILL 3
- POINCIANA SUBDIVISION NBRHD 5 NORTH VIL 3
- POINCIANA VLG 2 NBHD 1
- ROLLING OAKS PH 7
- Siesta Lago
- SONOMA RESORT AT TAPESTRY PH 1
- STOREY CREEK PH6
- STOREY LAKE TR K
- SUMMERVILLE RESORT
- VENTURA AT WINDSOR HILLS CONDO PH 1
Market Summary
Current real estate data for Single Family in KISSIMMEE as of Oct 19, 2026
2,257
Single Family Listed
166
Avg DOM
215
Avg $ / SqFt
$474,640
Avg List Price
Property Summary
- Located in the SHADOW BAY UNIT 2 subdivision, 2704 WINDING RIDGE AVENUE S KISSIMMEE FL is a Single Family for sale in KISSIMMEE, FL, 34741. It is listed for $365,000 and features 4 beds, 3 baths, and has approximately 2,021 square feet of living space, and was originally constructed in 1984. The current price per square foot is $181. The average price per square foot for Single Family listings in KISSIMMEE is $215. The average listing price for Single Family in KISSIMMEE is $474,640. To schedule a showing of MLS#o6447274 at 2704 WINDING RIDGE AVENUE S in KISSIMMEE, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of REAL BROKER, LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 2704 WINDING RIDGE AVENUE S
KISSIMMEE, FL
