Under contract-accepting backup offers. 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.
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.
Property Details
Price:
$495,000
MLS #:
O6423922
Status:
Active Under Contract
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
ISLE OF PINES FIFTH ADD
Neighborhood:
32832orlandomossparklakemaryjane
Listed Date:
Jul 9, 2026
Finished Sq Ft:
1,960
Total Sq Ft:
3,220
Lot Size:
14,499 sqft / 0.33 acres (approx)
Year Built:
1985
See this Listing
Schools
Elementary School:
Moss Park Elementary
Middle School:
Innovation Middle School
High School:
Innovation High
Interior
Appliances
Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Water Filtration System
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Ceramic Tile, Hardwood
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, 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
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Association Amenities
Optional Additional Fees, Park, Playground, Recreation Facilities, Trail(s)
Community Features
Community Boat Ramp, Dock, Fishing, Lake, Private Boat Ramp, Water Access, Waterfront, Park, Playground
Construction Materials
Log
Covered Spaces
5
Direction Faces
North
Exterior Features
Dog Run, Other, Rain Gutters, Sliding Doors, Storage
Garage Spaces
5
Open Parking YN
1
Other Structures
Storage, Workshop
Parking Features
Boat, Driveway, Garage Door Opener, RV Parking, Split Garage
Roof
Shingle
Waterfront Features
Lake, Waterfront
Window Features
Blinds, Double Pane Windows, Insulated Windows, Rods, Window Treatments
Financial
Tax Year
2025
Taxes
$4,413
Map
Community
- Address14126 WINTERSET DRIVE ORLANDO FL
- SubdivisionISLE OF PINES FIFTH ADD
- CityORLANDO
- CountyOrange
- Zip Code32832
Market Summary
Current real estate data for Single Family in ORLANDO as of Jul 23, 2026
3,102
Single Family Listed
100
Avg DOM
287
Avg $ / SqFt
$678,605
Avg List Price
Property Summary
- Located in the ISLE OF PINES FIFTH ADD subdivision, 14126 WINTERSET DRIVE ORLANDO FL is a Single Family for sale in ORLANDO, FL, 32832. It is listed for $495,000 and features 3 beds, 2 baths, and has approximately 1,960 square feet of living space, and was originally constructed in 1985. The current price per square foot is $253. The average price per square foot for Single Family listings in ORLANDO is $287. The average listing price for Single Family in ORLANDO is $678,605. To schedule a showing of MLS#o6423922 at 14126 WINTERSET DRIVE in ORLANDO, FL, contact your agent at 407-583-9870.
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Courtesy of CHARLES RUTENBERG REALTY ORLANDO. 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 include the name of the listing broker. Neither the listing company nor 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. 14126 WINTERSET DRIVE
ORLANDO, FL