⚠️ This listing is no longer active (Active Under Contract). Information reflects last known listing data.
$495,000

14126 WINTERSET DR, Orlando, FL 32832

Active Under Contract
3
Beds
2
Baths
1,960
Sq Ft
$252
Per Sq Ft
1985
Built
2
Days Listed
5
Garage
0.33
Acres

About This Property

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.

Facts & Features

Interior
Bedrooms3
Full Bathrooms2
Half Bathrooms0
Interior Sq Ft1,960
Total Structure Area3,220 sqft
FireplaceYes
FlooringCeramic Tile, Wood
HeatingCentral, Electric
CoolingCentral Air
AppliancesDishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Water
LaundryInside, Laundry Room
Interior FeaturesCeiling Fans(s), Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Livin
Window FeaturesBlinds, Double Pane Windows, Insulated Windows, Rods, Window
Property
Construction
Utilities
Community & HOA
Financial & Listing Details

Schools

School assignments and grades are informational — verify boundaries with the school district before purchasing.

Price History

Jul 9, 2026 Listed $495,000

Listed by CHARLES RUTENBERG REALTY ORLANDO · MLS# O6423922

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Listing information © 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved. Data deemed reliable but not guaranteed. Last updated: 2026-07-13.
IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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Mike Valdes
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