# 206 N HIGHLAND Avenue, Winter Garden, FL 34787 > **TL;DR:** 3bd/3ba single family, $999,999 ($532/sqft), built 1925, 1,880 sqft. > Fireplace, A/C, 1-car garage. Est. $5,349/mo. Listed 35 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $999,999 | | Price/sqft | $532 | | Bedrooms | 3 | | Bathrooms | 2 full, 1 half | | Square Feet | 1,880 | | Year Built | 1925 | | Lot Size | 10,454 sqft (0.24 acres) | | Stories | 1 | | Garage | 1-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 35 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $5,057 | | Estimated Insurance | $292 | | **Total** | **$5,349** | ## Nearby Schools - **Elementary:** Dillard Street Elem - **Middle:** Lakeview Middle - **High:** West Orange High ## Key Amenities - Fireplace - A/C - 1-car garage ## Property Highlights - Built in 1925 - 0.24 acre lot - Fireplace ## Description ### Agent Description Welcome to a beautifully renovated Historic Craftsman in the highly desired Golf Cart District of Downtown Winter Garden! ??his charming Winter Garden historic home offers the character, craftsmanship, and timeless details of a classic home with the peace of mind of extensive modern updates. The roof was replaced in 2024, and the home features all-new electrical, plumbing, HVAC, and thoughtful renovations throughout while preserving the charm that makes historic homes so special. inside, you'll find a dedicated home office, inviting living spaces, and original character blended seamlessly with modern finishes and everyday functionality. Outside, two charming porches provide the perfect spots to enjoy your morning coffee, relax with friends, or take in the character of this established neighborhood. Location is everything, and this home puts you right in the heart of the Downtown Winter Garden lifestyle. Located within the highly sought-after Golf Cart District and in close proximity to Downtown Winter Garden, you can easily enjoy the weekly farmers market, seasonal festivals, local restaurants, boutique shops, entertainment, and community events. If you've been searching for a historic home in Winter Garden, a renovated Craftsman, a move-in-ready home with major systems already updated, a golf-cart-friendly property, or a home close to Downtown Winter Garden, this is a rare opportunity to enjoy historic charm without sacrificing modern comfort. ## Location - **Address:** 206 N HIGHLAND Avenue, Winter Garden, FL 34787 - **County:** Orange - **Neighborhood:** COOPER & SEWELL ADD - **Coordinates:** 28.567783, -81.589426 - **Google Maps:** https://www.google.com/maps?q=28.567783,-81.589426 ## Virtual Tour & Media - **Video Tour:** https://www.propertypanorama.com/instaview/stellar/O6444632 ## Listing Agent - **Name:** Erica Diaz - **Brokerage:** Homevest Realty - **Broker Phone:** (407) 897-5400 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/206-N-Highland-Ave_Winter-Garden_FL_34787_M62714-86787?f=listhub&s=MFRMLSFL&m=O6444632&c=propsimple) ## Photos ![206 N HIGHLAND Avenue - Photo 1](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f811999391r.jpg) ![206 N HIGHLAND Avenue - Photo 2](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f2622131500r.jpg) ![206 N HIGHLAND Avenue - Photo 3](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3041232589r.jpg) ![206 N HIGHLAND Avenue - Photo 4](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3603203263r.jpg) ![206 N HIGHLAND Avenue - Photo 5](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f1312314948r.jpg) ![206 N HIGHLAND Avenue - Photo 6](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3088369213r.jpg) ![206 N HIGHLAND Avenue - Photo 7](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3578491700r.jpg) ![206 N HIGHLAND Avenue - Photo 8](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3785351946r.jpg) ![206 N HIGHLAND Avenue - Photo 9](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3667538398r.jpg) ![206 N HIGHLAND Avenue - Photo 10](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f64831266r.jpg) ![206 N HIGHLAND Avenue - Photo 11](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f1608705521r.jpg) ![206 N HIGHLAND Avenue - Photo 12](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f2825959141r.jpg) ![206 N HIGHLAND Avenue - Photo 13](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3572984955r.jpg) ![206 N HIGHLAND Avenue - Photo 14](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f467198168r.jpg) ![206 N HIGHLAND Avenue - Photo 15](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f1908279811r.jpg) ![206 N HIGHLAND Avenue - Photo 16](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f107786565r.jpg) ![206 N HIGHLAND Avenue - Photo 17](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f1236584134r.jpg) ![206 N HIGHLAND Avenue - Photo 18](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f2619077701r.jpg) ![206 N HIGHLAND Avenue - Photo 19](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f2333531240r.jpg) ![206 N HIGHLAND Avenue - Photo 20](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f2979914437r.jpg) ![206 N HIGHLAND Avenue - Photo 21](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f4119837387r.jpg) ![206 N HIGHLAND Avenue - Photo 22](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3861385109r.jpg) ![206 N HIGHLAND Avenue - Photo 23](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3500825708r.jpg) ![206 N HIGHLAND Avenue - Photo 24](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f970835332r.jpg) ![206 N HIGHLAND Avenue - Photo 25](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3507576462r.jpg) ![206 N HIGHLAND Avenue - Photo 26](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f2219731756r.jpg) ![206 N HIGHLAND Avenue - Photo 27](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f257413844r.jpg) ![206 N HIGHLAND Avenue - Photo 28](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3064032030r.jpg) ![206 N HIGHLAND Avenue - Photo 29](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3685919756r.jpg) ![206 N HIGHLAND Avenue - Photo 30](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f1628794900r.jpg) ![206 N HIGHLAND Avenue - Photo 31](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3909964290r.jpg) ![206 N HIGHLAND Avenue - Photo 32](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f4241610599r.jpg) ![206 N HIGHLAND Avenue - Photo 33](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3588380407r.jpg) ![206 N HIGHLAND Avenue - Photo 34](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3784152008r.jpg) ![206 N HIGHLAND Avenue - Photo 35](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3553083004r.jpg) ![206 N HIGHLAND Avenue - Photo 36](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f520509346r.jpg) ![206 N HIGHLAND Avenue - Photo 37](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f1287754772r.jpg) ![206 N HIGHLAND Avenue - Photo 38](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f1833073638r.jpg) ![206 N HIGHLAND Avenue - Photo 39](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f313687431r.jpg) ![206 N HIGHLAND Avenue - Photo 40](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f3758352515r.jpg) ![206 N HIGHLAND Avenue - Photo 41](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f847019952r.jpg) ![206 N HIGHLAND Avenue - Photo 42](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f1027668298r.jpg) ![206 N HIGHLAND Avenue - Photo 43](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f270410282r.jpg) ![206 N HIGHLAND Avenue - Photo 44](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f1338622661r.jpg) ![206 N HIGHLAND Avenue - Photo 45](http://lh.rdcpix.com/2ff03b3408113f54ce705025c3ddf0ddl-f1968724683r.jpg) --- **MLS#:** O6444632 | **Updated:** 2026-11-01 **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://staging.propertysimple.ai/listing/206-n-highland-avenue-winter-garden-fl-34787-8bc25aa5ee7c41acb9aa57cf62bb4595) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/206-n-highland-avenue-winter-garden-fl-34787-8bc25aa5ee7c41acb9aa57cf62bb4595#listing", "url": "https://staging.propertysimple.ai/listing/206-n-highland-avenue-winter-garden-fl-34787-8bc25aa5ee7c41acb9aa57cf62bb4595", "name": "206 N HIGHLAND Avenue, Winter Garden, FL 34787", "description": "Welcome to a beautifully renovated Historic Craftsman in the highly desired Golf Cart District of Downtown Winter Garden! ??his charming Winter Garden historic home offers the character, craftsmanship, and timeless details of a classic home with the peace of mind of extensive modern updates. 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