# 1060 GREGORY Drive, Maitland, FL 32751 > **TL;DR:** 3bd/2ba single family, $529,000 ($305/sqft), built 1962, 1,734 sqft. > Fireplace, A/C, 2-car garage. Est. $2,829/mo. Listed 5 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $529,000 | | Price/sqft | $305 | | Bedrooms | 3 | | Bathrooms | 2 full | | Square Feet | 1,734 | | Year Built | 1962 | | Lot Size | 12,197 sqft (0.28 acres) | | Stories | 1 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 5 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,675 | | Estimated Insurance | $154 | | **Total** | **$2,829** | ## Nearby Schools - **Elementary:** Lake Orienta Elementary - **Middle:** Milwee Middle - **High:** Lyman High ## Key Amenities - Fireplace - A/C - 2-car garage ## Property Highlights - Built in 1962 - 0.28 acre lot - Fireplace ## Description ### Agent Description Some homes have a character that simply cannot be recreated-and 1060 Gregory Drive is one of them. Built in 1962 and tucked beneath mature oaks draped in Spanish moss, this three-bedroom, two-bath Maitland home celebrates its original charm while offering the updates today's buyers appreciate. Warm hardwood floors flow through the home, while a dramatic brick feature wall separates the living and family rooms, with a fireplace facing each space. It is a memorable architectural detail that makes both rooms feel welcoming and distinct. The updated kitchen pairs shaker-style cabinetry with granite countertops and stainless steel appliances, while plantation shutters and ceiling fans add comfort and classic style throughout. The primary bedroom features dual closets. The guest bathroom also benefits from a new vanity. Step outside to an expansive backyard deck with plenty of room for dining, entertaining and lingering beneath the trees on beautiful Florida evenings. Major improvements include an ELECTRICAL UPDATE 2026, ALL NEW DUCTWORK 2026, HVAC and REROOF 2020, WATER HEATER 2022, a NEW FENCE installed in 2023 and REPIPED 2009. Set in an established Maitland neighborhood with quick access to Winter Park, Maitland and Interstate 4, this is a home with a story, a setting and a style all its own. Come experience the character, comfort and tree-lined charm that make 1060 Gregory Drive feel like home from the moment you arrive. ## Location - **Address:** 1060 GREGORY Drive, Maitland, FL 32751 - **County:** Seminole - **Neighborhood:** DRUID HILLS ESTATES 1ST ADD - **Coordinates:** 28.641618, -81.376898 - **Google Maps:** https://www.google.com/maps?q=28.641618,-81.376898 ## Virtual Tour & Media - **Video Tour:** https://www.zillow.com/view-imx/8c4c31f4-6969-4546-8aed-3c553a78740b?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard ## Listing Agent - **Name:** Jill Healey - **Brokerage:** Keller Williams Winter Park - **Phone:** 4077971420 - **Broker Phone:** (407) 545-6430 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/1060-Gregory-Dr_Maitland_FL_32751_M60620-90709?f=listhub&s=MFRMLSFL&m=O6445281&c=propsimple) ## Photos ![1060 GREGORY Drive - Photo 1](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f619925800r.jpg) ![1060 GREGORY Drive - Photo 2](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f2217444049r.jpg) ![1060 GREGORY Drive - Photo 3](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f3805171443r.jpg) ![1060 GREGORY Drive - Photo 4](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f2561832023r.jpg) ![1060 GREGORY Drive - Photo 5](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f2446590017r.jpg) ![1060 GREGORY Drive - Photo 6](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f1207645542r.jpg) ![1060 GREGORY Drive - Photo 7](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f258721953r.jpg) ![1060 GREGORY Drive - Photo 8](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f2938898750r.jpg) ![1060 GREGORY Drive - Photo 9](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f3645701064r.jpg) ![1060 GREGORY Drive - Photo 10](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f4049231671r.jpg) ![1060 GREGORY Drive - Photo 11](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f1853733881r.jpg) ![1060 GREGORY Drive - Photo 12](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f578253880r.jpg) ![1060 GREGORY Drive - Photo 13](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f3810242449r.jpg) ![1060 GREGORY Drive - Photo 14](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f1304213155r.jpg) ![1060 GREGORY Drive - Photo 15](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f2435439492r.jpg) ![1060 GREGORY Drive - Photo 16](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f1060116614r.jpg) ![1060 GREGORY Drive - Photo 17](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f1222182315r.jpg) ![1060 GREGORY Drive - Photo 18](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f947949894r.jpg) ![1060 GREGORY Drive - Photo 19](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f2427788946r.jpg) ![1060 GREGORY Drive - Photo 20](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f3928854891r.jpg) ![1060 GREGORY Drive - Photo 21](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f1098537720r.jpg) ![1060 GREGORY Drive - Photo 22](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f671010048r.jpg) ![1060 GREGORY Drive - Photo 23](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f2183597866r.jpg) ![1060 GREGORY Drive - Photo 24](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f837528891r.jpg) ![1060 GREGORY Drive - Photo 25](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f3010927937r.jpg) ![1060 GREGORY Drive - Photo 26](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f3754943648r.jpg) ![1060 GREGORY Drive - Photo 27](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f2318064441r.jpg) ![1060 GREGORY Drive - Photo 28](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f4112271601r.jpg) ![1060 GREGORY Drive - Photo 29](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f2254382558r.jpg) ![1060 GREGORY Drive - Photo 30](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f3024945383r.jpg) ![1060 GREGORY Drive - Photo 31](http://lh.rdcpix.com/73a5fc3e702b1102566b293c0b0518f2l-f3278419433r.jpg) --- **MLS#:** O6445281 | **Updated:** 2026-10-02 **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/1060-gregory-drive-maitland-fl-32751-o6445281) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/1060-gregory-drive-maitland-fl-32751-o6445281#listing", "url": "https://www.propertysimple.ai/listing/1060-gregory-drive-maitland-fl-32751-o6445281", "name": "1060 GREGORY Drive, Maitland, FL 32751", "description": "Some homes have a character that simply cannot be recreated-and 1060 Gregory Drive is one of them. Built in 1962 and tucked beneath mature oaks draped in Spanish moss, this three-bedroom, two-bath Maitland home celebrates its original charm while offering the updates today's buyers appreciate. Warm hardwood floors flow through the home, while a dramatic brick feature wall separates the living and family rooms, with a fireplace facing each space. It is a memorable architectural detail that makes both rooms feel welcoming and distinct. The updated kitchen pairs shaker-style cabinetry with granite countertops and stainless steel appliances, while plantation shutters and ceiling fans add comfort and classic style throughout. The primary bedroom features dual closets. The guest bathroom also benefits from a new vanity. Step outside to an expansive backyard deck with plenty of room for dining, entertaining and lingering beneath the trees on beautiful Florida evenings. Major improvements include an ELECTRICAL UPDATE 2026, ALL NEW DUCTWORK 2026, HVAC and REROOF 2020, WATER HEATER 2022, a NEW FENCE installed in 2023 and REPIPED 2009. Set in an established Maitland neighborhood with quick access to Winter Park, Maitland and Interstate 4, this is a home with a story, a setting and a style all its own. 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