# 101 LEE Street, Windermere, FL 34786 > **TL;DR:** 5bd/4ba single family, $1,395,000 ($333/sqft), built 1978, 4,186 sqft. > Pool, Fireplace, A/C. Est. $7,461/mo. Listed 22 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,395,000 | | Price/sqft | $333 | | Bedrooms | 5 | | Bathrooms | 4 full | | Square Feet | 4,186 | | Year Built | 1978 | | Lot Size | 18,295 sqft (0.42 acres) | | Stories | 3 | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 22 | ## Why This Home Stands Out - **Pool** - Patio ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $7,054 | | Estimated Insurance | $407 | | **Total** | **$7,461** | ## Nearby Schools - **Elementary:** Windermere Elem - **Middle:** Gotha Middle - **High:** Olympia High ## Key Amenities - Pool - Fireplace - A/C ## Property Highlights - Built in 1978 - 0.42 acre lot - 3 stories - Private pool - Fireplace ## Description ### Agent Description Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-rich home offers nearly 4,200 square feet of versatile living space just steps from Windermere's charming downtown. Situated on nearly half an acre, this five-bedroom, four-bath residence pairs distinctive architectural character with thoughtful updates, abundant natural light and exceptional flexibility. The main living level brings together the kitchen, dining area and expansive great room, where high ceilings and a striking gas fireplace create a warm and inviting gathering space. Four sets of beautiful, new sliding glass doors open to an expansive balcony overlooking the screened pool, extending the living and entertaining space outdoors. A private-entry in-law suite adds another compelling feature to this unique home, offering exceptional possibilities for multigenerational living, extended-stay guests or a private work-from-home space. This lower level includes two bedrooms, two full baths, spacious living area, and a wet bar with mini-refrigerator. The fifth bedroom, currently enjoyed as a home gym, is also perfect for an office, playroom or hobby room. Privately positioned on its own level, the generous primary suite provides a peaceful retreat with a spacious sitting area and private balcony. Recent, significant investments throughout the property include new windows and doors, three newer HVAC units, new roof September 2026, interior and exterior paint, updated astroturf in the side yard, as well as numerous other improvements, all while preserving the character and scale of this established Windermere home. The pool and patio, featuring a screen enclosure just added in 2020, and newer cabanas, perfect for entertaining, relaxing and enjoying Florida living year-round. The location offers a lifestyle all its own, with downtown Windermere's weekly farmers market, community events, parks and small-town charm just a short walk or golf cart ride away. Town of Windermere residents also enjoy private access to a boat ramp on the renowned Butler Chain of Lakes, as well as to the town tennis and pickleball courts! Zoned for top rated Windermere Elementary and Olympia High, and situated just minutes from the shopping and dining of The Grove at Isleworth and Restaurant Row, this distinctive home delivers a rare combination of space, flexibility, and character all in a desirable, downtown Windermere location. ## Location - **Address:** 101 LEE Street, Windermere, FL 34786 - **County:** Orange - **Neighborhood:** TOWN OF WINDERMERE - **Coordinates:** 28.494927, -81.528418 - **Google Maps:** https://www.google.com/maps?q=28.494927,-81.528418 ## Virtual Tour & Media - **Video Tour:** https://www.propertypanorama.com/instaview/stellar/O6437573 ## Listing Agent - **Name:** Julie Bettosini, PA - **Brokerage:** Stockworth Realty Group LLC - **Phone:** 3216899594 - **Broker Phone:** (407) 909-9000 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/101-Lee-St_Windermere_FL_34786_M53750-08041?f=listhub&s=MFRMLSFL&m=O6437573&c=propsimple) ## Photos ![101 LEE Street - Photo 1](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f368150889r.jpg) ![101 LEE Street - Photo 2](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2957869862r.jpg) ![101 LEE Street - Photo 3](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2303899372r.jpg) ![101 LEE Street - Photo 4](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f1476176432r.jpg) ![101 LEE Street - Photo 5](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f542922874r.jpg) ![101 LEE Street - Photo 6](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f1983353688r.jpg) ![101 LEE Street - Photo 7](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f42006407r.jpg) ![101 LEE Street - Photo 8](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f3158237061r.jpg) ![101 LEE Street - Photo 9](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f799394373r.jpg) ![101 LEE Street - Photo 10](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f233452538r.jpg) ![101 LEE Street - 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Photo 31](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2591108077r.jpg) ![101 LEE Street - Photo 32](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f3826410687r.jpg) ![101 LEE Street - Photo 33](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2232172658r.jpg) ![101 LEE Street - Photo 34](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f3039020077r.jpg) ![101 LEE Street - Photo 35](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f3142673589r.jpg) ![101 LEE Street - Photo 36](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f1614503742r.jpg) ![101 LEE Street - Photo 37](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f626633926r.jpg) ![101 LEE Street - Photo 38](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f850617897r.jpg) ![101 LEE Street - Photo 39](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f245973062r.jpg) ![101 LEE Street - Photo 40](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f396791633r.jpg) ![101 LEE Street - Photo 41](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f720520423r.jpg) ![101 LEE Street - Photo 42](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2242481225r.jpg) ![101 LEE Street - Photo 43](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f1056924479r.jpg) ![101 LEE Street - Photo 44](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f282457879r.jpg) ![101 LEE Street - Photo 45](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f221115760r.jpg) ![101 LEE Street - Photo 46](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f992244778r.jpg) ![101 LEE Street - Photo 47](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f1084539262r.jpg) ![101 LEE Street - Photo 48](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f1853598732r.jpg) ![101 LEE Street - Photo 49](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f4101138375r.jpg) ![101 LEE Street - Photo 50](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f1787714896r.jpg) ![101 LEE Street - Photo 51](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f103906840r.jpg) ![101 LEE Street - Photo 52](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2080103869r.jpg) ![101 LEE Street - Photo 53](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2835496317r.jpg) ![101 LEE Street - Photo 54](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2551418245r.jpg) ![101 LEE Street - Photo 55](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f394223569r.jpg) ![101 LEE Street - Photo 56](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f325733155r.jpg) ![101 LEE Street - Photo 57](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f616825482r.jpg) ![101 LEE Street - Photo 58](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2068449269r.jpg) ![101 LEE Street - Photo 59](http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f3654484215r.jpg) --- **MLS#:** O6437573 | **Updated:** 2026-09-16 **Source:** listhub *Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/101-lee-street-windermere-fl-34786-o6437573) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/101-lee-street-windermere-fl-34786-o6437573#listing", "url": "https://www.propertysimple.ai/listing/101-lee-street-windermere-fl-34786-o6437573", "name": "101 LEE Street, Windermere, FL 34786", "description": "Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-rich home offers nearly 4,200 square feet of versatile living space just steps from Windermere's charming downtown. Situated on nearly half an acre, this five-bedroom, four-bath residence pairs distinctive architectural character with thoughtful updates, abundant natural light and exceptional flexibility. The main living level brings together the kitchen, dining area and expansive great room, where high ceilings and a striking gas fireplace create a warm and inviting gathering space. Four sets of beautiful, new sliding glass doors open to an expansive balcony overlooking the screened pool, extending the living and entertaining space outdoors. A private-entry in-law suite adds another compelling feature to this unique home, offering exceptional possibilities for multigenerational living, extended-stay guests or a private work-from-home space. This lower level includes two bedrooms, two full baths, spacious living area, and a wet bar with mini-refrigerator. The fifth bedroom, currently enjoyed as a home gym, is also perfect for an office, playroom or hobby room. Privately positioned on its own level, the generous primary suite provides a peaceful retreat with a spacious sitting area and private balcony. Recent, significant investments throughout the property include new windows and doors, three newer HVAC units, new roof September 2026, interior and exterior paint, updated astroturf in the side yard, as well as numerous other improvements, all while preserving the character and scale of this established Windermere home. The pool and patio, featuring a screen enclosure just added in 2020, and newer cabanas, perfect for entertaining, relaxing and enjoying Florida living year-round. The location offers a lifestyle all its own, with downtown Windermere's weekly farmers market, community events, parks and small-town charm just a short walk or golf cart ride away. Town of Windermere residents also enjoy private access to a boat ramp on the renowned Butler Chain of Lakes, as well as to the town tennis and pickleball courts! Zoned for top rated Windermere Elementary and Olympia High, and situated just minutes from the shopping and dining of The Grove at Isleworth and Restaurant Row, this distinctive home delivers a rare combination of space, flexibility, and character all in a desirable, downtown Windermere location.", "image": [ "http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f368150889r.jpg", "http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2957869862r.jpg", "http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f2303899372r.jpg", "http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f1476176432r.jpg", "http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f542922874r.jpg", "http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f1983353688r.jpg", "http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f42006407r.jpg", "http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f3158237061r.jpg", "http://lh.rdcpix.com/e3ca362f78193a31202e6f4b838a2cc3l-f799394373r.jpg", 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