Orlando Waterford - Jon Swanson
1/46
Listing Courtesy Of: PREMIER SOTHEBY'S INTL. REALTY, 407-644-3295, Shelley Heistand
Local Realty Services Provided By: Keller Williams Classic Realty
Overview
What It'll Cost
Neighborhood
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$2,495,000
105 PINE STREET, WINDERMERE, FL 34786
5 Beds
6 Baths
5,696 sq ft
.57 ac
$2,495,000

105 PINE STREET, WINDERMERE, FL 34786

Estimation provided by Keller Williams Realty Inc.
5 Beds
6 Baths
5,696 sq ft
.57 ac
Active
For Sale
Virtual Tour

Property 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

Property Details

Compare This Home
Overview
Property Type
Single Family Residence
Property Size
5,696 sq ft
Year Built
2015
Days on Site
48 Days
HVAC
Central Air, Electric, Zoned, Central, Heat Pump
Parking
3 Parking Spaces
Keller Williams Advantage II Realty
Orlando Waterford
SL3271073

Activity History

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Purchase Price: $2,495,000
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Price & Tax History

Date
Event
Price
03/07/2025
Price Decrease
$2,495,000
(-9.27%)
02/13/2025
Listed
$2,750,000
(+746.15%)
06/25/2014
Sold
$325,000
(-35%)
10/15/2013
Sold
$500,000
Year
Property Tax
Assessed Value
Assessed Value is a combination of the land and additions.
2023
$12,063
(-20.79%)
$732,272
No Breakdown Available
2021
$15,229
(+34.65%)
$690,237
No Breakdown Available
2018
$11,310
(+3.46%)
$665,403
No Breakdown Available
2017
$10,932
(+0.12%)
$652,996
Land 265,000 + Additions 387,996
2016
$10,919
$642,636
Land 265,000 + Additions 377,636
The Property History data displayed is obtained from public records and/or MLS feeds from the local jurisdiction in which the applicable property is located. As kw.com cannot guarantee that all public records and MLS data is accurate and error-free, it is important that you contact your agent directly in order to obtain the most up-to-date information available.

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Transit & Commute

Estimated commute times from Downtown Windermere
Car-Dependent Walkable Very Walkable
Keller Williams Advantage II Realty
Orlando Waterford
SL3271073

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