This modern Tuscan Parade of Homes winner was custom-built with fabulous design and versatility. With Spanish Mediterranean influence, the home creates spaces that are excellent for indoor/outdoor entertaining and casual resort-style living, as well as a sleek courtyard design for the ultimate in entertaining and privacy. A solid oversized Mahogany pre-entry door leads to an outdoor private oasis complete with pool and alfresco dining prior to approaching the main residence entry foyer. Retractable screens create a seamless indoor-outdoor living. Other features include two amazing chef's kitchens (both a primary and entertaining/catering kitchen) with natural gas commercial appliances including a grill, steam oven, three convection ovens and a Wolf pizza oven surrounded by custom cabinetry and a barrel brick ceiling. The downstairs master retreat has a sitting area, two-sided fireplace and access to outdoor lanai through motorized sliding doors, as well as a master bath with dual water closets, steam shower, and massage room with adjoining cedar-lined dry sauna. Downstairs also includes another bedroom suite, spacious open gathering room, multiple dining areas, private theater, dual office and separate guest casita, which allows for truly a one-level living experience. The second floor enjoys two more bedroom suites, a workout area and flex living space. Other features include Crestron home automation system, thermal pane windows, refrigerated wine room, 15 security cameras and five-car capacity garages.
Single-familyProperty Type
2008Year Built
0.46 acresLot Size
$609Est. Price/Sq.Ft.
5 car garageParking
Listed by Mick Night• PREMIER SOTHEBY'S INTL. REALTY
Bought with Shelley Heistand• COLDWELL BANKER REALTY
This rustic modern Parade of Homes winner was custom built with extreme care and thought for the most discerning buyer. No detail has been overlooked, creating spaces that are excellent for both entertaining and living. Mahogany entry door leads to an outdoor lanai complete with pool, dining, and lounge. Retractable screens that can create indoor/outdoor space with a push of a button. Amazing chef’s kitchen with natural gas burners, a steam oven, three convection and a Wolf pizza oven surrounded by custom cabinetry and a barrel tiled ceiling. A separate entertaining grill area overlooking family room. Motorized sliding glass doors completely retract to blend interior and exterior. Luxurious downstairs master retreat with large sitting room, two-sided fireplace and access to lanai through motorized sliding doors. Master bath with his and her water closets, steam shower, massage room with adjoining cedar lined dry sauna. Downstairs office, attached and detached guest room, allows for one floor living. Second floor has two bedrooms, workout area, and flex living space with private balcony. Whole home automation system, theater room, foam insulation, double pane Hurd windows, refrigerated wine room, fifteen security cameras, Crestron audio system, Auto lighting system, and five car capacity garages. Located close to Downtown Winter Park, with quick access to Baldwin, Audubon, and Downtown Orlando makes this a prime location. Property is leased until 5/31/2018.
Stellar MLS as Distributed by MLS Grid #O5420823
Aug 24, 2016
Listing Removed
—
Public Records
May 25, 2006
Sold
$760,000
$120/sq ft
Stellar MLS as Distributed by MLS Grid #O4561690
Mar 7, 2005
Listing Removed
—
Public Records
Nov 17, 2000
Sold
$511,000
$81/sq ft
Public Records
Aug 2, 1999
Sold
$382,500
$60/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$41,183 (+7.0%)
$630,000 + $2,146,230
$2,776,230
2024
$38,473 (+7.1%)
$630,000 + $2,146,230
$2,776,230
2023
$35,919 (+22.7%)
$630,000 + $2,047,076
$2,677,076
2022
$29,268
$630,000 + $1,264,224
$1,894,224
2021
$29,242 (+1.9%)
$630,000 + $1,264,224
$1,894,224
2020
$28,699 (−6.3%)
$630,000 + $1,224,061
$1,854,061
2019
$30,613 (+1.0%)
$507,000 + $1,369,287
$1,876,287
2018
$30,303 (+0.5%)
$507,000 + $1,369,287
$1,876,287
2017
$30,154 (+2.0%)
$507,000 + $1,289,749
$1,796,749
2016
$29,554 (−1.2%)
$507,000 + $1,289,749
$1,796,749
2015
$29,903 (+8.5%)
2014
$27,571 (+2.6%)
2013
$26,875 (+2.5%)
2012
$26,227
Tax history for 1600 Highland Rd
Year
Property tax
Land + Additions
Assessment*
2025
$41,183 (+7.0%)
$630,000 + $2,146,230
$2,776,230
2024
$38,473 (+7.1%)
$630,000 + $2,146,230
$2,776,230
2023
$35,919 (+22.7%)
$630,000 + $2,047,076
$2,677,076
2022
$29,268
$630,000 + $1,264,224
$1,894,224
2021
$29,242 (+1.9%)
$630,000 + $1,264,224
$1,894,224
2020
$28,699 (−6.3%)
$630,000 + $1,224,061
$1,854,061
2019
$30,613 (+1.0%)
$507,000 + $1,369,287
$1,876,287
2018
$30,303 (+0.5%)
$507,000 + $1,369,287
$1,876,287
2017
$30,154 (+2.0%)
$507,000 + $1,289,749
$1,796,749
2016
$29,554 (−1.2%)
$507,000 + $1,289,749
$1,796,749
2015
$29,903 (+8.5%)
2014
$27,571 (+2.6%)
2013
$26,875 (+2.5%)
2012
$26,227
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Permits
Beds
5
Baths
6
Stories
2
Lot width
—
Lot depth
—
Lot size
0.46 Acres
Year renovated
2008
Sq. Ft.
6,345
Year built
2008
Style
Single Family Residential
County
Orange County
APN
302207890815100
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
R-1AA
\N
Residential District
These districts are established within the city to provide areas for single-family dwellings and necessary accessory buildings. The regulations enumerated for this district are designed to encourage and promote the construction of and the continued use of the land for single-family dwellings, to promote and encourage a suitable environment for family life, to prohibit uses of the land which would substantially interfere with development or continuation of single-family dwellings in the districts, and to prevent use of the land for purposes which would overburden the public facilities. Permitted as conditional uses within these districts will be certain structures and uses required to serve the residents such as public schools, churches and noncommercial recreational uses. Areas zoned for R-1AA districts shall be those existing low-density residential areas plus certain undeveloped areas which should develop in a similar manner according to the comprehensive plan.
Permitted uses
Include but are not limited to:
Housing-Single unit
Nov 24, 2025 • Final
Tree removal
Issue an after-the-fact permit for the replanting of approved shade trees.
Grading
Oct 31, 2025 • Final
Residential fence/wall
Remove a section of metal fence and replace it with a concrete masonry unit block wall.
Demolition
Grading
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Property details
Parking
Parking Information
Garage Dimensions: 24x24
Parking Features: Circular Driveway, Garage Door Opener, Garage Faces Rear, Garage Faces Side
Heating Information: Central, Electric, Heat Recovery Unit, Zoned
Cooling Information: Central Air, Zoned
Interior Features
Interior Features: Built-in Features, Cathedral Ceiling(s), Ceiling Fans(s), Central Vaccum, Eat-in Kitchen, Elevator, High Ceilings, Master Bedroom Main Floor, Open Floorplan, Solid Wood Cabinets, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Walk-in Closet(s)
Window Features: Blinds, ENERGY STAR Qualified Windows, Thermal Windows
Appliances: Bar Fridge, Convection Oven, Dishwasher, Freezer, Gas Water Heater, Indoor Grill, Kitchen Reverse Osmosis System, Refrigerator, Solar Hot Water, Tankless Water Heater, Wine Refrigerator