105 PINE STREET, WINDERMERE, FL 34786 - Tampa Bay Luxury Real Estate & Waterfront Homes

$2,500,000

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… Read More 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! Read Less

Courtesy of ALIGN REAL ESTATE LLC 305-389-2922

Listing Snapshot

Days Online

Last Updated

May 9, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

5,696

Lot Size

0.57 Acres

Year Built

2015

MLS Number

O6405163

Additional Details

Property Access

Road Responsibility: Public Maintained Road, Road Surface: Dirt, Paved

Appliances & Equipment

Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Other equipment: Irrigation Equipment, Generator

Building

Built in 2015, Living area: 5696, Living area units: Square Feet, Building faces West, Levels: One, Construction Materials: Block, Concrete, Stucco

Community

Street Lights

Cooling

Central Air, Zoned

Exterior Features

Patio/Porch Features: Covered, Deck, Front Porch, Patio, Rear Porch, Screened, Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors

Fence

Fenced, Vinyl

Fireplaces

Family Room, Gas

Floors

Ceramic Tile, Luxury Vinyl, Tile, Wood

Foundation

Slab

Garage

3 spaces

Heating

Central, Electric, Zoned

Interior Features

Accessibility Features, Built-in Features, Ceiling Fans(s), Coffered Ceiling(s), Crown Molding, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, 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

Laundry

In Garage, Inside, Laundry Closet, Laundry Room

Lot

0.57 acres, Corner Lot, In County, Landscaped, Oversized Lot, Private, Mature Landscaping, Oak Trees, Trees/Landscaped

Parking

Boat, Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Oversized, RV Garage

Pool

Gunite, Heated, In Ground, Salt Water

Property

Completed, Other structures: Guest House, Outdoor Kitchen, Pool, Water

Roof

Shingle

Security Features

Security System Owned, Smoke Detector(s)

Sewer

Septic Tank

Taxes

Additional parcels description:, Parcel Number: 17-23-28-9337-05-000, Public Survey Range: 28, Public Survey Section: 17, Annual Amount: $16,804, Tax Block: 05/000, Tax Book Number: G/36, 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, Lot: 000, Year: 2025, Zoning: SFR

Utilities

Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Sprinkler Well, Water Connected, Water Source: Public, Well

Water Features

Water Body Name: BUTLER CHAIN OF LAKES

Windows

Aluminum Frames, Blinds, Double Pane Windows, Drapes, Rods, Shades, Shutters, Window Treatments

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