# 241 N DILLARD Street, Winter Garden, FL 34787 > **TL;DR:** 4bd/3ba single family, $1,499,999 ($428/sqft), built 1953, 3,507 sqft. > Fireplace, A/C. Est. $8,022/mo. Listed 373 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,499,999 | | Price/sqft | $428 | | Bedrooms | 4 | | Bathrooms | 3 full | | Square Feet | 3,507 | | Year Built | 1953 | | Lot Size | 27,878 sqft (0.64 acres) | | Stories | 1 | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 373 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $7,585 | | Estimated Insurance | $437 | | **Total** | **$8,022** | ## Nearby Schools - **Elementary:** Dillard Street Elem - **Middle:** Lakeview Middle - **High:** West Orange High ## Key Amenities - Fireplace - A/C ## Property Highlights - Built in 1953 - 0.64 acre lot - Fireplace ## Description ### Agent Description Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida's most coveted locations - the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you'll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you'll always be reminded that you're just moments away from all the charm, energy, and convenience of Downtown Winter Garden - one of the most desirable small-town destinations in Florida. The property's expansive outdoor footprint sets it apart - a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2-3 vehicles comfortably, with ample room for a boat, RV, or guest parking - a rare find in this highly sought-after downtown location. Whether you're arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida's most beloved communities. Opportunities like this simply don't come around twice. Come see for yourself why this remarkable downtown retreat isn't just a home - it's a legacy waiting to be continued. ## Location - **Address:** 241 N DILLARD Street, Winter Garden, FL 34787 - **County:** Orange - **Neighborhood:** J L DILLARD SUB 3 - **Coordinates:** 28.568996, -81.583285 - **Google Maps:** https://www.google.com/maps?q=28.568996,-81.583285 ## Virtual Tour & Media - **Video Tour:** https://www.zillow.com/view-imx/37f39412-fc82-4833-8cd6-c4ee120d5e6a?wl=true&setAttribution=mls&initialViewType=pano ## Listing Agent - **Name:** Erica Diaz - **Brokerage:** Homevest Realty - **Broker Phone:** (407) 897-5400 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/241-N-Dillard-St_Winter-Garden_FL_34787_M63633-10069?f=listhub&s=MFRMLSFL&m=O6353975&c=propsimple) ## Photos ![241 N DILLARD Street - Photo 1](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1849008910r.jpg) ![241 N DILLARD Street - Photo 2](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1072497848r.jpg) ![241 N DILLARD Street - Photo 3](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1392321368r.jpg) ![241 N DILLARD Street - Photo 4](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2653976755r.jpg) ![241 N DILLARD Street - Photo 5](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3923836594r.jpg) ![241 N DILLARD Street - Photo 6](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3762142308r.jpg) ![241 N DILLARD Street - Photo 7](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2709359300r.jpg) ![241 N DILLARD Street - Photo 8](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2383761655r.jpg) ![241 N DILLARD Street - Photo 9](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3397165200r.jpg) ![241 N DILLARD Street - Photo 10](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3859851836r.jpg) ![241 N DILLARD Street - Photo 11](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1592875514r.jpg) ![241 N DILLARD Street - Photo 12](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2005243685r.jpg) ![241 N DILLARD Street - Photo 13](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2112388107r.jpg) ![241 N DILLARD Street - Photo 14](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1297194110r.jpg) ![241 N DILLARD Street - Photo 15](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1434934093r.jpg) ![241 N DILLARD Street - Photo 16](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1283178919r.jpg) ![241 N DILLARD Street - Photo 17](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f291077838r.jpg) ![241 N DILLARD Street - Photo 18](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2133945735r.jpg) ![241 N DILLARD Street - Photo 19](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1431806356r.jpg) ![241 N DILLARD Street - Photo 20](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2978668425r.jpg) ![241 N DILLARD Street - Photo 21](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2883551110r.jpg) ![241 N DILLARD Street - Photo 22](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2912213998r.jpg) ![241 N DILLARD Street - Photo 23](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f823325043r.jpg) ![241 N DILLARD Street - Photo 24](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3708976903r.jpg) ![241 N DILLARD Street - Photo 25](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2710633259r.jpg) ![241 N DILLARD Street - Photo 26](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1779987471r.jpg) ![241 N DILLARD Street - Photo 27](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1934224801r.jpg) ![241 N DILLARD Street - Photo 28](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f2977088500r.jpg) ![241 N DILLARD Street - Photo 29](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3520815255r.jpg) ![241 N DILLARD Street - Photo 30](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f859951170r.jpg) ![241 N DILLARD Street - Photo 31](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1723627368r.jpg) ![241 N DILLARD Street - Photo 32](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f889595028r.jpg) ![241 N DILLARD Street - Photo 33](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1972903625r.jpg) ![241 N DILLARD Street - Photo 34](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1501536552r.jpg) ![241 N DILLARD Street - Photo 35](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3778601433r.jpg) ![241 N DILLARD Street - Photo 36](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3440584912r.jpg) ![241 N DILLARD Street - Photo 37](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3661624530r.jpg) ![241 N DILLARD Street - Photo 38](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1892291380r.jpg) ![241 N DILLARD Street - Photo 39](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f666000554r.jpg) ![241 N DILLARD Street - Photo 40](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f4075232531r.jpg) ![241 N DILLARD Street - Photo 41](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f117458522r.jpg) ![241 N DILLARD Street - Photo 42](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f882559500r.jpg) ![241 N DILLARD Street - Photo 43](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3922576849r.jpg) ![241 N DILLARD Street - Photo 44](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3756945296r.jpg) ![241 N DILLARD Street - Photo 45](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1048084244r.jpg) ![241 N DILLARD Street - Photo 46](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1203266995r.jpg) ![241 N DILLARD Street - Photo 47](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f3196651670r.jpg) ![241 N DILLARD Street - Photo 48](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1625809017r.jpg) ![241 N DILLARD Street - Photo 49](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f539238073r.jpg) ![241 N DILLARD Street - Photo 50](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f1360014066r.jpg) ![241 N DILLARD Street - Photo 51](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f605080729r.jpg) ![241 N DILLARD Street - Photo 52](http://lh.rdcpix.com/ff5a092b3a3e72e594f63d251fb7b552l-f341941304r.jpg) --- **MLS#:** O6353975 | **Updated:** 2026-10-27 **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/241-n-dillard-street-winter-garden-fl-34787-7692b96c2a184c2a8784a10f29d5c1e2) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/241-n-dillard-street-winter-garden-fl-34787-7692b96c2a184c2a8784a10f29d5c1e2#listing", "url": "https://staging.propertysimple.ai/listing/241-n-dillard-street-winter-garden-fl-34787-7692b96c2a184c2a8784a10f29d5c1e2", "name": "241 N DILLARD Street, Winter Garden, FL 34787", "description": "Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida's most coveted locations - the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you'll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you'll always be reminded that you're just moments away from all the charm, energy, and convenience of Downtown Winter Garden - one of the most desirable small-town destinations in Florida. The property's expansive outdoor footprint sets it apart - a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2-3 vehicles comfortably, with ample room for a boat, RV, or guest parking - a rare find in this highly sought-after downtown location. Whether you're arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida's most beloved communities. Opportunities like this simply don't come around twice. 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