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Property Description
Rare opportunity to own an authentic log home in the heart of Isle of Pines! Combining timeless rustic charm with thoughtful modern updates, this beautifully maintained 3-bedroom, 2-bath retreat offers the perfect blend of rustic character and modern updates. This one-of-a-kind home feels like a peaceful country retreat while remaining just a short drive from Lake Nona, SR 417, shopping, dining, and Orlando International Airport. Step inside to find an updated kitchen with a large island that's perfect for gathering with family and friends, new appliances (2024), beautifully updated bathrooms, and wood and tile flooring throughout. Cozy up beside the wood-burning fireplace on cooler evenings or enjoy the abundance of natural light streaming through all-new windows. Major improvements include a roof (2024) and A/C (2023) H2O system (2023), Water Heater (2025). Outside, the lifestyle continues with a screened-in pool, a spacious front porch that's perfect for morning coffee while watching the local wildlife, including baby deer that visit often!, and a fully fenced side yard just off the kitchen that's ideal for dogs or little ones to play safely. Need room for your hobbies, toys, or future plans? In addition to the detached two-car garage, you'll find a second detached building currently housing three vehicles, it's ready to become a workshop, studio, home gym, additional storage, or potentially an accessory dwelling unit. This home is served by well and septic, offering lower monthly utility costs, and residents have the option to join the voluntary Isle of Pines Property Owners Association. For a small annual fee you can enjoy access to Lake Mary Jane with a private boat ramp and dock, community events, playground, trails, and more. If you've been dreaming of a home with character, privacy, room to spread out, and a little piece of Old Florida charm, this is one you won't want to miss.
Full Property Details
Full Property Details for 14126 Winterset Dr
General
- Price: $495,000
- Taxes: $4,413 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6423922
- Updated: 7/10/2026
- Added to Site: 5 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 7
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
- Fireplace: Yes
- Fireplace(s): Living Room, Masonry, Wood Burning
- Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Water Filtration System
- Furnishings: Negotiable
- Flooring: Ceramic Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Optional Additional Fees, Park, Playground, Recreation Facilities, Trail(s)
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, Heated, In Ground, Screen Enclosure
Exterior
- Exterior Features: Dog Run, Other, Rain Gutters, Sliding Doors, Storage
Parking
- Garage: Yes
- Garage Spaces: 5
- Covered Spaces: 5
- Parking Features: Boat, Driveway, Garage Door Opener, RV Parking, Split Garage
Location
- Area: 32832 - Orlando/Moss Park/Lake Mary Jane
- County: Orange
- Development Name: 32832 - Orlando/Moss Park/Lake Mary Jane
- Subdivision: ISLE OF PINES FIFTH ADD
- Driving Directions: From SR 417, take Exit 22 for Narcoossee Road and head south. Turn left onto Moss Park Road, then left onto Lake Mary Jane Road. Continue to Winterset Drive and turn right. The home will be on your left.
- Direction Faces: North
School Information
- Elementary School: Moss Park Elementary
- Middle School: Innovation Middle School
- High School: Innovation High
Community
- Community Name: 32832 - Orlando/Moss Park/Lake Mary Jane
- Community Features: Community Boat Ramp, Dock, Fishing, Lake, Private Boat Ramp, Water Access, Waterfront, Park, Playground
- Optional Amenities: Optional Additional Fees, Park, Playground, Recreation Facilities, Trail(s)
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Septic Tank
- Water District: LAKE MARY JANE
- Water: Well
- Utility Description: Cable TV Available, Electricity Connected, Private
Structural Information
- Exterior Const.: Log
- Roof: Shingle
- Windows: Blinds, Double Pane Windows, Insulated Windows, Rods, Window Treatments
- Stories/Levels: One
- Square Feet: 1,960
- Sq. Ft. Source: Public Records
- Year Built: 1985
Additional Structures
- Other Structures: Storage, Workshop
Lot Features
- Lot Size (Acres): 0.33
- Lot Size (Sq. Ft.): 14,499
- Lot Size: 14499
- Frontage: Street Paved
- Street/Road Desc.: Paved, Asphalt, Gravel
Water Features
- Water Access: Yes
- Water Access Desc: Beach, Lake
- Water Extras: Yes
- Water Front Name: LAKE MARY JANE
- Water Front Desc.: Lake, Waterfront
Financial Considerations
- Assoc Fee Desc.: None
- Tax Amount: $4,413.24
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: ISLE OF PINES FIFTH ADDITION V/5 LOT 309
- Flood Zone Info: X
- APN: 252431388203090
- Property ID: 252431388203090
- Block/Lot/Section: 3
Listed by Charles Rutenberg Realty Orlando
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Schools
Schools serving 14126 Winterset Dr
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Moss Park Elementary School 9301 North Shore Golf Club Boulevard, Orlando, FL 32832 | K-5 | 4 mi |
Innovation Middle 13950 Storey Park Boulevard, Orlando, FL 32832 | 6-8 | 4.5 mi |
Lake Nona High School 12500 Narcoossee Road, Orlando, FL 32832 | 9-12 | 4.4 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 14126 Winterset Dr
Date
Details
Price
Change
Source
7/09/2026
Listed
$495,000
45.59%
MLS
12/30/2020
Sold
$340,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 14126 Winterset Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,413
5%
$302,089
6%
2024
$4,190
7%
$285,857
3%
2023
$3,902
-20%
$277,531
-4%
2021
$4,849
27%
$290,132
8%
2022
$3,826
-21%
$269,448
45%
2021
$4,849
90%
$185,925
2%
2019
$2,548
1%
$181,745
2%
2018
$2,524
2%
$178,356
2%
2017
$2,481
1%
$174,688
2%
2016
$2,454
-2%
$171,095
1%
2015
$2,495
-2%
$169,906
1%
2014
$2,547
2%
$168,558
1%
2013
$2,490
—
$166,067
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 14126 Winterset Dr
14126 Winterset Drive, Orlando, FL 32832 (MLS# O6423922) is a Single Family property with 3 bedrooms and 2 full bathrooms. 14126 Winterset Drive is currently listed for $495,000 and was received on July 09, 2026. Want to learn more about 14126 Winterset Drive? Do you have questions about finding other Single Family real estate for sale in Orlando? You can browse all Orlando real estate or contact a Coldwell Banker agent to request more information.

