105 PINE STREET, WINDERMERE, FL 34786

$2,495,000 Was $2,750,000

Beds: 5

Baths: 5 Full / 1 Half

Sq. Ft.: 5,696 Sq. Ft.

Year Built: 2015

Lot Size: 0.57 Acres

Garage: 3

Pool: Yes

DOM: 47

Property Overview

Status: Closed

Property Type: Residential

MLS #: 7b9627d9963405afed44955a9389ac55

Subdivision: WINDERMERE

County: Orange

HOA Fee: N/A

Year Built: 2015

Construction: Block, Concrete, Stucco

Foundation: Slab

Roof: Shingle

Cooling: Central Air, Zoned

Heating: Central, Electric, Heat Pump, Zoned

Sewer: Septic Tank

Water Source: Public, Well

Zoning: SFR

Tax Amount: $12,928.84 (2024)

Date Sold: Apr 25, 2025

Sold Price: $2,285,000

Listed On: Feb 8, 2025

Description

One or more photo(s) has been virtually staged. On a serene over half acre lot in the heart of historic downtown Windermere this fabulous one-of-a kind multi-generational home is a short distance from the charming boutiques, eateries, coffee shops, local wine shop, brewery, the weekly farmers market, food trucks and Windermere Library. The main home was meticulously expanded and redesigned in 2023. The casita was built new in 2024. The fabulous ADA-accessible casita with its own private entrance is 1,246 square feet, ideal for hosting friends, family or aging parents. This casita boasts a generously sized great room with plastered Kiva fireplace and built-in bookcases, large kitchen with plastered hood vent, custom tile, porcelain concrete countertops, honed marble island top, coffee station, Café Matte white/brushed bronze refrigerator, 30-inch double oven with six-burner gas cooktop, soft close custom cabinets and drawers, 39-inch iron door, custom stonework walls and floating shelves. The spacious bedroom has a walk-in custom closet & en-suite bath with dual vanities, marble countertops and edgeless walk-in shower. Additional amenities include yellow pine wood ceiling beams, hickory wood flooring, 11½-inch baseboards, solid knotty alder wood doors, custom reclaimed pine closet barn door, and 10-12-foot vaulted ceilings. The main home features four spacious bedrooms, 4.5 baths, a large laundry room, theater-game room and office with 4,450 square feet. The spacious great room has a cozy fireplace, decorative wood beam ceiling and opens to the gourmet kitchen. This kitchen is a chef’s dream featuring stainless steel appliances including Bosch double ovens, Viking gas cooktop, walk-in pantry, Cambria countertops, farmhouse sink, custom cabinetry and oversized island with breakfast bar. The spacious owner’s suite with pool views has two walk-in custom closets and spa-like bath with a freestanding solid stone soaking tub, separate oversized walk-in shower and dual solid stone sinks designed with luxury and relaxation in mind. The large theater-game room has sliding glass doors leading to the covered lanai and private fenced yard. You will enjoy entertaining outside with your sparkling, heated saltwater pool with spa and summer kitchen. A large three-car RV garage joins the casita to the main home. This garage with soaring ceiling has room for two car lifts and RV parking with a 50-amp plug, epoxy flooring and storage racks. This home was thoughtfully designed with optimal storage and custom finishes. Amenities and renovations include new roof, exterior paint, gutters, LVP flooring, custom built-in closets, aluminum fenced yard, pool-spa, two Generac generators, security cameras, termite bond, three tankless water heaters, irrigation well, 10-12-foot ceilings throughout and custom closets in all rooms to keep you organized. Residents of the Town of Windermere enjoy exclusive access to the town’s private boat ramp, giving access to the Butler Chain of Lakes as well as the town’s private pickleball/tennis courts. Golf carts are welcome in this charming town. No HOA restrictions. Location is a short commute to top-rated schools, major highways, upscale shopping, Orlando’s renowned attractions and world-class golf courses.

Exterior Features

Irrigation System, Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors

Directions

Main Street to West on W. 2nd Ave - to North on Pine St. Corner of Pine and W. 1st Ave.

School Information

Elementary: Windermere Elem

Middle: Gotha Middle

High: Olympia High

Location

Get Directions View on Google Maps

Mortgage Estimator

*Estimate includes Principal & Interest (P&I) only. It does not include taxes, insurance, HOA fees, or PMI. Rates and payments may vary. Consult a lender for accurate figures.

Listing Information

Provided Courtesy of:

PREMIER SOTHEBY'S INTL. REALTY

Listing Agent: Shelley Heistand

Information is deemed reliable but not guaranteed. Information provided is 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.

Data last updated: March 1, 2026, 5:51 pm UTC

MLS Source: Stellar MLS Copyright © 2026

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