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$2,335,000
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Property Description
Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of Lakes. Set on an oversized, over half-acre corner lot in downtown Windermere, this custom home offers a rare blend of privacy, flexibility, and walkability to local dining, coffee shops, boutiques, and the weekly farmers market. Built in 2015 and thoughtfully expanded, this 5,696 square foot home features five bedrooms and five and a half bathrooms, including a fully separate casita ideal for in-law living, guests, or private quarters. From the moment you arrive, fresh landscaping and an exposed brick front porch create a warm and inviting entrance. Inside, the open living space is both spacious and comfortable, with high ceilings, wood beams, crown molding, and a gas fireplace, complemented by shiplap and exposed brick accents. The kitchen opens seamlessly to the main living area and overlooks the backyard, featuring a large Cambria quartz island, Kohler farm sink, walk-in pantry, Bosch double ovens, Viking gas cooktop, custom hood, LG refrigerator, soft-close cabinetry, under-cabinet lighting, and a dedicated coffee bar. The primary suite offers peaceful backyard views, two custom walk-in closets, and a well-appointed bath with dual vanities, a makeup station, a garden tub, and a large walk-in shower with floor-to-ceiling tile and dual showerheads. Additional bedrooms are thoughtfully placed, including one with an ensuite bath. A versatile flex room with a coffered ceiling, storage, and its own laundry setup connects to a private office with built-ins and a walk-in closet. A secondary primary suite provides a comfortable space for extended family or guests. In total, the home offers three separate laundry areas for added convenience. Outdoor living is designed for true Florida living. Two sets of sliding glass doors, including one from the flex room, open to a covered lanai with wood plank ceiling and fans, along with a fully equipped summer kitchen featuring an Artisan natural gas grill, vent hood, sink, and icemaker. The space extends to an expansive paver patio surrounding a heated saltwater pool and spa with water features, all overlooking a large fenced backyard. The casita, completed in 2023 and offering over 1,200 square feet, lives like a private residence with its own entrance and Spanish Mediterranean character, including wood beams, hardwood flooring, and a Kiva-style fireplace. It features a full living room, a kitchen with GE Café appliances and a quartz island, and a spacious bedroom suite with a custom walk-in closet and a beautifully finished bath. A screened lanai and separate fenced yard provide added privacy. A three-car garage with high ceilings includes an oversized RV-height door, 50-amp plug, and space for additional storage or lifts, along with a third laundry area. Additional features include dual AC systems, tankless water heaters, and a Generac generator. Residents of Windermere enjoy private access to the Butler Chain of Lakes, parks, tennis courts, and a boat ramp, all golf cart accessible. Golf cart friendly with tree-lined streets and a true small-town feel. No HOA and conveniently located near top-rated schools, major roadways, and world-class dining and entertainment. This is a truly unique Windermere home designed for modern multigenerational living. Schedule your private showing today!
Full Property Details
Full Property Details for 105 Pine St
General
- Sold For: $2,335,000
- Taxes: $16,804 (2025)
- Status: Closed
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6405163
- Added to Site: 46 day(s) ago
Rental Information
- Min. Lease: 7 Months
Interior
- Number of Rooms: 13
- Interior Features: Accessibility Features, Built-in Features, Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
- Fireplace: Yes
- Fireplace(s): Family Room, Gas, Other Room
- Appliances: Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer
- Furnishings: Unfurnished
- Flooring: Ceramic Tile, Luxury Vinyl, Tile, Hardwood
Rooms
Bathrooms
- Total Bathrooms: 6
- Full Bathrooms: 5
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: In Garage, Inside, Laundry Closet, Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, Heated, In Ground, Salt Water
- Spa: Yes
- Spa Description: Heated, In Ground
- Security/Safety: Security System Owned, Smoke Detector(s)
Exterior
- Exterior Features: Irrigation System, Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors
- Deck/Patio: Covered, Deck, Front Porch, Patio, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Deck, Front Porch, Patio, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 3
- Covered Spaces: 3
- Parking Features: Boat, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Oversized, RV Garage
Location
- Area: 34786 - Windermere
- County: Orange
- Development Name: 34786 - Windermere
- Subdivision: WINDERMERE
- Driving Directions: Main Street to West on W. 2nd Ave - to North on Pine St. Corner of Pine and W. 1st Ave.
- Direction Faces: West
School Information
- Elementary School: Windermere Elem
- Middle School: Gotha Middle
- High School: Olympia High
Community
- Community Name: 34786 - Windermere
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Central, Electric, Zoned
Utilities
- Sewer: Septic Tank
- Water District: BUTLER CHAIN OF LAKES
- Water: Public, Well
- Utility Description: Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Sprinkler Well, Street Lights, Water Connected
Structural Information
- Architectural Info: Custom, Florida, Other, Mediterranean, Traditional
- Architectural Style: Custom, Florida, Other, Mediterranean, Traditional
- Builder: Robert Heinz/Heinz Group
- Exterior Const.: Block, Concrete, Stucco
- Roof: Shingle
- Windows: Aluminum Frames, Blinds, Double Pane Windows, Drapes, Rods, Shades, Shutters, Window Treatments
- Stories/Levels: One
- Square Feet: 5,696
- Sq. Ft. Source: Builder
- Living Area: 5,696 Sq. Ft.
- Year Built: 2015
Additional Structures
- Other Structures: Guest House, Outdoor Kitchen
Lot Features
- Property View: Pool, Water
- Lot Size (Acres): 0.57
- Lot Size (Sq. Ft.): 24,719
- Lot Size: 24719
- Frontage: Private Road
- Street/Road Desc.: Dirt, Other, Paved
- Fencing (Description): Fenced, Other, Vinyl
Water Features
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Lake - Chain of Lakes
- Water Extras: Yes
- Water Front Name: BUTLER CHAIN OF LAKES
Financial Considerations
- Tax Amount: $16,804
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: PLAT OF WINDERMERE G/36 BLK E BEG NE COR OF BLK E RUN S 17 D EG E 105 FT TH S73W 236 FT TH N17W 85 FT TO A POC CONCAVE SE LY HAVING A RAD 20 FT DELTA 90 CHORD BEARING N28E ARC LENGTH
- Flood Zone Info: x
- APN: 172328933705000
- Property ID: 172328933705000
- Block/Lot/Section: 05/000
Listed by Align Real Estate Llc
Sold by The Real Estate Collection Llc
Get Pre-Approved Today
Schools
Schools serving 105 Pine St
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Windermere Elementary School 11125 Park Avenue, Windermere, FL 34786 | K-5 | 0.6 mi |
Gotha Middle School 9155 Gotha Road, Windermere, FL 34786 | 6-8 | 2.5 mi |
Olympia High School 4301 South Apopka Vineland Road, Orlando, FL 32835 | 9-12 | 2.1 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 105 Pine St
Date
Details
Price
Change
Source
6/10/2026
Sold
$2,335,000
-6.6%
MLS
5/07/2026
Listed
$2,500,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
105 Pine Street, Windermere, FL 34786 (MLS# O6405163) is a Single Family property that was sold at $2,335,000 on June 10, 2026. Want to learn more about 105 Pine Street? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

