# 5138 FAIRWAY OAKS DR, Windermere, FL 34786 > **TL;DR:** 4bd/5ba single family, $4,999,500 ($1155/sqft), built 1994, 4,330 sqft. > Pool, Spa, Fireplace, View. Est. $26,738/mo. Listed 160 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $4,999,500 | | Price/sqft | $1155 | | Bedrooms | 4 | | Bathrooms | 5 full | | Square Feet | 4,330 | | Year Built | 1994 | | Lot Size | 21,780 sqft (0.50 acres) | | Stories | 1 | | Garage | 3-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 160 | ## Why This Home Stands Out - **Pool** - Porch - **Views** - Water, Golf Course, Lake - **Large Garage** - 3-car garage ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $25,280 | | Estimated Insurance | $1,458 | | **Total** | **$26,738** | ## Nearby Schools - **Elementary:** Windermere Elem - **Middle:** Chain of Lakes Middle - **High:** Olympia High ## Key Amenities - Pool - Spa - Fireplace - View - A/C - 3-car garage ## Property Highlights - Built in 1994 - 0.50 acre lot - Private pool - Fireplace ## Description ### Agent Description Set along Isleworth's signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club-recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances-including a striking black range with matching hood, refrigerator, and microwave-all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida's premier shopping, dining, and entertainment destinations. ## Location - **Address:** 5138 FAIRWAY OAKS DR, Windermere, FL 34786 - **County:** Orange - **Neighborhood:** ISLEWORTH - **Coordinates:** 28.484272, -81.530447 - **Google Maps:** https://www.google.com/maps?q=28.484272,-81.530447 ## Virtual Tour & Media - **Video Tour:** https://player.vimeo.com/video/1183953909?h=f00523e43b&badge=0&autopause=0&player_id=0&app_id=58479 ## Listing Agent - **Name:** Monica Lochmandy - **Brokerage:** Isleworth Realty, LLC - **Phone:** 4072306888 - **Broker Phone:** (407) 876-0111 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/5138-Fairway-Oaks-Dr_Windermere_FL_34786_M62650-56440?f=listhub&s=MFRMLSFL&m=O6401757&c=propsimple) ## Photos ![5138 FAIRWAY OAKS DR - Photo 1](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1408522150r.jpg) ![5138 FAIRWAY OAKS DR - Photo 2](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1482647388r.jpg) ![5138 FAIRWAY OAKS DR - Photo 3](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f3441251094r.jpg) ![5138 FAIRWAY OAKS DR - Photo 4](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1976400017r.jpg) ![5138 FAIRWAY OAKS DR - Photo 5](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f264624561r.jpg) ![5138 FAIRWAY OAKS DR - Photo 6](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2061490609r.jpg) ![5138 FAIRWAY OAKS DR - Photo 7](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1365731695r.jpg) ![5138 FAIRWAY OAKS DR - Photo 8](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f4013053112r.jpg) ![5138 FAIRWAY OAKS DR - Photo 9](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1532197488r.jpg) ![5138 FAIRWAY OAKS DR - Photo 10](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1763568400r.jpg) ![5138 FAIRWAY OAKS DR - Photo 11](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f627906789r.jpg) ![5138 FAIRWAY OAKS DR - Photo 12](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2941922754r.jpg) ![5138 FAIRWAY OAKS DR - Photo 13](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f361812348r.jpg) ![5138 FAIRWAY OAKS DR - Photo 14](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f391881906r.jpg) ![5138 FAIRWAY OAKS DR - Photo 15](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f3103671045r.jpg) ![5138 FAIRWAY OAKS DR - Photo 16](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2960103422r.jpg) ![5138 FAIRWAY OAKS DR - Photo 17](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f3494078044r.jpg) ![5138 FAIRWAY OAKS DR - Photo 18](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f4118538782r.jpg) ![5138 FAIRWAY OAKS DR - Photo 19](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2681428021r.jpg) ![5138 FAIRWAY OAKS DR - Photo 20](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2308658634r.jpg) ![5138 FAIRWAY OAKS DR - Photo 21](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f4032110005r.jpg) ![5138 FAIRWAY OAKS DR - Photo 22](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f3349792725r.jpg) ![5138 FAIRWAY OAKS DR - Photo 23](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f497318880r.jpg) ![5138 FAIRWAY OAKS DR - Photo 24](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f263923769r.jpg) ![5138 FAIRWAY OAKS DR - Photo 25](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1841888695r.jpg) ![5138 FAIRWAY OAKS DR - Photo 26](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1432287120r.jpg) ![5138 FAIRWAY OAKS DR - Photo 27](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1358428636r.jpg) ![5138 FAIRWAY OAKS DR - Photo 28](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2577826437r.jpg) ![5138 FAIRWAY OAKS DR - Photo 29](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2452317955r.jpg) ![5138 FAIRWAY OAKS DR - Photo 30](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f337200907r.jpg) ![5138 FAIRWAY OAKS DR - Photo 31](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f4063565237r.jpg) ![5138 FAIRWAY OAKS DR - Photo 32](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f3586075112r.jpg) ![5138 FAIRWAY OAKS DR - Photo 33](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f3789870258r.jpg) ![5138 FAIRWAY OAKS DR - Photo 34](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f3159887026r.jpg) ![5138 FAIRWAY OAKS DR - Photo 35](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f94914910r.jpg) ![5138 FAIRWAY OAKS DR - Photo 36](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f971527809r.jpg) ![5138 FAIRWAY OAKS DR - Photo 37](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2575297340r.jpg) ![5138 FAIRWAY OAKS DR - Photo 38](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f867963754r.jpg) ![5138 FAIRWAY OAKS DR - Photo 39](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2697376683r.jpg) ![5138 FAIRWAY OAKS DR - Photo 40](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2617504498r.jpg) ![5138 FAIRWAY OAKS DR - Photo 41](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1704099r.jpg) ![5138 FAIRWAY OAKS DR - Photo 42](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f4179923188r.jpg) ![5138 FAIRWAY OAKS DR - Photo 43](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2580647682r.jpg) ![5138 FAIRWAY OAKS DR - Photo 44](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f220568852r.jpg) ![5138 FAIRWAY OAKS DR - Photo 45](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f726059808r.jpg) ![5138 FAIRWAY OAKS DR - Photo 46](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2598082006r.jpg) ![5138 FAIRWAY OAKS DR - Photo 47](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f639548983r.jpg) ![5138 FAIRWAY OAKS DR - Photo 48](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f2601861483r.jpg) ![5138 FAIRWAY OAKS DR - Photo 49](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f3475032541r.jpg) ![5138 FAIRWAY OAKS DR - Photo 50](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f3968685086r.jpg) ![5138 FAIRWAY OAKS DR - Photo 51](http://lh.rdcpix.com/c51aac4af510a2671d67397e414058f5l-f1510079400r.jpg) --- **MLS#:** O6401757 | **Updated:** 2026-09-29 **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/5138-fairway-oaks-dr-windermere-fl-34786-o6401757) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/5138-fairway-oaks-dr-windermere-fl-34786-o6401757#listing", "url": "https://www.propertysimple.ai/listing/5138-fairway-oaks-dr-windermere-fl-34786-o6401757", "name": "5138 FAIRWAY OAKS DR, Windermere, FL 34786", "description": "Set along Isleworth's signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club-recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances-including a striking black range with matching hood, refrigerator, and microwave-all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. 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