# 919 Winding Oak Trail, Lexington, KY 40511 > **TL;DR:** 5bd/4ba single family, $380,000 ($115/sqft), built 2005, 3,300 sqft. > Fireplace, A/C, 2-car garage. Est. $2,152/mo. Listed 15 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $380,000 | | Price/sqft | $115 | | Bedrooms | 5 | | Bathrooms | 3 full, 1 half | | Square Feet | 3,300 | | Year Built | 2005 | | Lot Size | 5,140 sqft (0.12 acres) | | Stories | 2 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 15 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $1,921 | | Estimated Insurance | $111 | | HOA | $120 | | **Total** | **$2,152** | ## Nearby Schools - **Elementary:** Sandersville - **Middle:** Leestown - **High:** Bryan Station ## Key Amenities - Fireplace - A/C - 2-car garage ## Property Highlights - Built in 2005 - 0.12 acre lot - 2 stories - Fireplace ## Description ### Agent Description Approximately 3,300 square feet of finished living space, 5 bedrooms, 3.5 baths, a finished walk-out basement, and a 2-car garage, this home provides plenty of room. Open Floor plan with lots of natural Light. The open kitchen offers room for a table or island, Lots of cabinets and a pantry. There is also a formal dining room and a bonus room on the main level. Upstairs, you'll find three generously sized bedrooms, including a huge primary suite with a private bath, garden tub, and large walk-in closet. The additional bedrooms also offer excellent space and storage. The finished walk-out basement features a full bathroom, kitchenette, and spacious family room-an ideal setup for guests, extended family, a mother-in-law suite, or a private recreation area. $120 Year HOA is mandatory but pool membership is optional. The HVAC upstairs is not working. We have an $8400 quote to replace it with a Trane unit. This cost may be added to the offer price. Sold As-Is. Inspections are welcome. ## Location - **Address:** 919 Winding Oak Trail, Lexington, KY 40511 - **County:** Fayette - **Neighborhood:** Masterson Station - **Coordinates:** 38.109437, -84.53951 - **Google Maps:** https://www.google.com/maps?q=38.109437,-84.53951 ## Listing Agent - **Name:** Roger Browning - **Brokerage:** Four Seasons Realty - **Broker Phone:** (859) 396-7295 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/919-Winding-Oak-Trl_Lexington_KY_40511_M38587-62712?f=listhub&s=LBARKY&m=26028934&c=propsimple) ## Photos ![919 Winding Oak Trail - Photo 1](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f609097846r.jpg) ![919 Winding Oak Trail - Photo 2](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2325111229r.jpg) ![919 Winding Oak Trail - Photo 3](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1613908202r.jpg) ![919 Winding Oak Trail - Photo 4](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f614484397r.jpg) ![919 Winding Oak Trail - Photo 5](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3575482004r.jpg) ![919 Winding Oak Trail - Photo 6](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2813951736r.jpg) ![919 Winding Oak Trail - Photo 7](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f50112760r.jpg) ![919 Winding Oak Trail - Photo 8](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3066257465r.jpg) ![919 Winding Oak Trail - Photo 9](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f507356860r.jpg) ![919 Winding Oak Trail - Photo 10](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f278064835r.jpg) ![919 Winding Oak Trail - Photo 11](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3012591364r.jpg) ![919 Winding Oak Trail - Photo 12](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3523012455r.jpg) ![919 Winding Oak Trail - Photo 13](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3743152972r.jpg) ![919 Winding Oak Trail - Photo 14](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3521516378r.jpg) ![919 Winding Oak Trail - Photo 15](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f998907151r.jpg) ![919 Winding Oak Trail - Photo 16](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1626865742r.jpg) ![919 Winding Oak Trail - Photo 17](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1734850178r.jpg) ![919 Winding Oak Trail - Photo 18](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2325980757r.jpg) ![919 Winding Oak Trail - Photo 19](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3866051706r.jpg) ![919 Winding Oak Trail - Photo 20](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f4017821008r.jpg) ![919 Winding Oak Trail - Photo 21](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2138110820r.jpg) ![919 Winding Oak Trail - Photo 22](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1713263524r.jpg) ![919 Winding Oak Trail - Photo 23](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2382216515r.jpg) ![919 Winding Oak Trail - Photo 24](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f4171074065r.jpg) ![919 Winding Oak Trail - Photo 25](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f375006594r.jpg) ![919 Winding Oak Trail - Photo 26](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f445233666r.jpg) ![919 Winding Oak Trail - Photo 27](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1550326474r.jpg) ![919 Winding Oak Trail - Photo 28](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2937636651r.jpg) ![919 Winding Oak Trail - Photo 29](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2376089167r.jpg) ![919 Winding Oak Trail - Photo 30](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3272002097r.jpg) ![919 Winding Oak Trail - Photo 31](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2702025715r.jpg) ![919 Winding Oak Trail - Photo 32](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2077610247r.jpg) ![919 Winding Oak Trail - Photo 33](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1933434754r.jpg) ![919 Winding Oak Trail - Photo 34](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3448185748r.jpg) ![919 Winding Oak Trail - Photo 35](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1861496669r.jpg) ![919 Winding Oak Trail - Photo 36](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3262200686r.jpg) ![919 Winding Oak Trail - Photo 37](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3876574059r.jpg) ![919 Winding Oak Trail - Photo 38](http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3869634018r.jpg) --- **MLS#:** 26028934 | **Updated:** 2026-10-20 **Source:** listhub *Copyright © 2026 ImagineMLS. 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://staging.propertysimple.ai/listing/919-winding-oak-trail-lexington-ky-40511-b172e7b785c34cb3b169b9fb873c7098) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/919-winding-oak-trail-lexington-ky-40511-b172e7b785c34cb3b169b9fb873c7098#listing", "url": "https://staging.propertysimple.ai/listing/919-winding-oak-trail-lexington-ky-40511-b172e7b785c34cb3b169b9fb873c7098", "name": "919 Winding Oak Trail, Lexington, KY 40511", "description": "Approximately 3,300 square feet of finished living space, 5 bedrooms, 3.5 baths, a finished walk-out basement, and a 2-car garage, this home provides plenty of room. Open Floor plan with lots of natural Light. The open kitchen offers room for a table or island, Lots of cabinets and a pantry. There is also a formal dining room and a bonus room on the main level. Upstairs, you'll find three generously sized bedrooms, including a huge primary suite with a private bath, garden tub, and large walk-in closet. The additional bedrooms also offer excellent space and storage. The finished walk-out basement features a full bathroom, kitchenette, and spacious family room-an ideal setup for guests, extended family, a mother-in-law suite, or a private recreation area. $120 Year HOA is mandatory but pool membership is optional. The HVAC upstairs is not working. We have an $8400 quote to replace it with a Trane unit. This cost may be added to the offer price. Sold As-Is. Inspections are welcome.", "image": [ "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f609097846r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2325111229r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1613908202r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f614484397r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3575482004r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2813951736r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f50112760r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3066257465r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f507356860r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f278064835r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3012591364r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3523012455r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3743152972r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3521516378r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f998907151r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1626865742r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1734850178r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2325980757r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3866051706r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f4017821008r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2138110820r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1713263524r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2382216515r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f4171074065r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f375006594r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f445233666r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1550326474r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2937636651r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2376089167r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3272002097r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2702025715r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2077610247r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1933434754r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3448185748r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1861496669r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3262200686r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3876574059r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3869634018r.jpg" ], "primaryImageOfPage": { "@type": "ImageObject", "url": "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f609097846r.jpg", "caption": "919 Winding Oak Trail - Lexington, KY" }, "datePosted": "2026-10-19", "dateModified": "2026-10-20T02:47:48.428Z", "mainEntity": { "@type": "Accommodation", "@id": "https://staging.propertysimple.ai/listing/919-winding-oak-trail-lexington-ky-40511-b172e7b785c34cb3b169b9fb873c7098#property", "name": "919 Winding Oak Trail, Lexington, KY 40511", "address": { "@type": "PostalAddress", "streetAddress": "919 Winding Oak Trail", "addressLocality": "Lexington", "addressRegion": "KY", "postalCode": "40511", "addressCountry": "US" }, "geo": { "@type": "GeoCoordinates", "latitude": 38.109437, "longitude": -84.53951 }, "image": [ "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f609097846r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2325111229r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1613908202r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f614484397r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3575482004r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2813951736r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f50112760r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3066257465r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f507356860r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f278064835r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3012591364r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3523012455r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3743152972r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3521516378r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f998907151r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1626865742r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1734850178r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2325980757r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3866051706r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f4017821008r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2138110820r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1713263524r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2382216515r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f4171074065r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f375006594r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f445233666r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1550326474r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2937636651r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2376089167r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3272002097r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2702025715r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f2077610247r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1933434754r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3448185748r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f1861496669r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3262200686r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3876574059r.jpg", "http://lh.rdcpix.com/2c372c39a7a41d072fcff2f7c9e877b6l-f3869634018r.jpg" ], "identifier": { "@type": "PropertyValue", "propertyID": "MLS", "value": "26028934" }, "accommodationCategory": "Single Family Residence", "numberOfBedrooms": 5, "numberOfBathroomsTotal": 4, "numberOfFullBathrooms": 3, "numberOfPartialBathrooms": 1, "floorSize": { "@type": "QuantitativeValue", "value": 3300, "unitCode": "FTK", "unitText": "square feet" }, "yearBuilt": 2005, "amenityFeature": [ { "@type": "LocationFeatureSpecification", "name": "Heating", "value": "Heat Pump (Heating)" }, { "@type": "LocationFeatureSpecification", "name": "Cooling", "value": "Electric, Heat Pump" }, { "@type": "LocationFeatureSpecification", "name": "Appliances", "value": "Dishwasher, Microwave, Refrigerator, Range, Dishwasher, Microwave, Refrigerator, Range" }, { "@type": "LocationFeatureSpecification", "name": "Flooring", "value": "Tile, Vinyl, Laminate" }, { "@type": "LocationFeatureSpecification", "name": "Construction Materials", "value": "Brick Veneer, Vinyl Siding" }, { "@type": "LocationFeatureSpecification", "name": "Parking Features", "value": "Driveway, Garage - Attached" }, { "@type": "LocationFeatureSpecification", "name": "Fireplace", "value": true }, { "@type": "LocationFeatureSpecification", "name": "Air Conditioning", "value": true } ], "additionalProperty": [ { "@type": "PropertyValue", "name": "Lot Size", "value": "0.12 acres" }, { "@type": "PropertyValue", "name": "Stories", "value": 2 }, { "@type": "PropertyValue", "name": "Garage Spaces", "value": 2 }, { "@type": "PropertyValue", "name": "Property Subtype", "value": "Single Family Residence" } ] }, "offers": { "@type": "Offer", "@id": "https://staging.propertysimple.ai/listing/919-winding-oak-trail-lexington-ky-40511-b172e7b785c34cb3b169b9fb873c7098#offer", "url": "https://staging.propertysimple.ai/listing/919-winding-oak-trail-lexington-ky-40511-b172e7b785c34cb3b169b9fb873c7098", "price": 380000, "priceCurrency": "USD", "businessFunction": "http://purl.org/goodrelations/v1#Sell", "availability": "https://schema.org/InStock", "seller": { "@id": "https://staging.propertysimple.ai/listing/919-winding-oak-trail-lexington-ky-40511-b172e7b785c34cb3b169b9fb873c7098#agent" } }, "provider": { "@type": "Person", "@id": "https://staging.propertysimple.ai/listing/919-winding-oak-trail-lexington-ky-40511-b172e7b785c34cb3b169b9fb873c7098#agent", "name": "Roger Browning", "worksFor": { "@type": "Organization", "@id": "https://staging.propertysimple.ai/listing/919-winding-oak-trail-lexington-ky-40511-b172e7b785c34cb3b169b9fb873c7098#brokerage", "name": "Four Seasons Realty", "telephone": "(859) 396-7295", "logo": { "@type": "ImageObject", "url": "http://lh.rdcpix.com/14e65dd1c65c11e4b1f8765de3424f4ck-c3083276869r.png" } } } } ```