Set on over half an acre along the shores of Lake Maitland in the heart of the coveted Vias, this exceptional residence by Modish Homes is both a former 2018 Parade of Homes winner and a standout example of Winter Park luxury living. From the moment you enter, a dramatic two-story foyer sets the tone, drawing your eye through to the main living space where a statement wood-burning fireplace anchors the room and expansive glass frames breathtaking views of the water beyond. Every space has been thoughtfully designed to maximize both scale and sightlines, creating an effortless connection between indoors and the natural beauty outside. The home features touches of Walnut floors, detailing and doors, bringing warmth throughout. At the center of the home, the chef’s kitchen is both refined and functional, featuring custom cabinetry, a full suite of Dacor appliances, and an oversized walk-in pantry. A striking wet bar with a glass wine wall adds a layer of sophistication, ideal for entertaining. The dining room is equally impressive, offering panoramic lake views and seamless access to the outdoor living areas. The main-level primary suite is a true private retreat, highlighted by chevron-pattern tile flooring and a spa-inspired bath complete with dual vanities, designer lighting, a freestanding soaking tub, and an expansive walk-in shower. The main level also includes two additional guest suites and a glass-enclosed office, offering both comfort and flexibility. Upstairs, two more bedrooms are complemented by a spacious loft and a large balcony that captures sweeping views of the lake. Designed to rival a private resort, the outdoor living experience is nothing short of exceptional. A fully equipped summer kitchen, resort-style pool and spa, two outdoor showers, and expansive green space create a setting that is both functional and visually stunning. A private viewing dock overlooks the water or reconfigure it to a boat dock, allowing you to fully embrace life on the lake while enjoying views of the iconic Isle of Sicily. Beyond the property, the lifestyle is equally compelling. Additional features include a full Control4 home automation system, sauna, and an expansive double-entry driveway providing ample parking. Located just minutes from the boutiques, dining, and cafés of Park Avenue, and within close proximity to Kraft Azalea Garden and the Winter Park Racquet Ball Club, this home offers the perfect balance of privacy and convenience. This is truly a one-of-a-kind opportunity to own a true showpiece on the Winter Park Chain of Lakes.
Single-familyProperty Type
2018Year Built
0.56 acresLot Size
$1,431Price/Sq.Ft.
2 car garageParking
Listed by Christopher Christensen• ONE LUXURY INTERNATIONAL LLC
Listed by Jane Peterson• ONE LUXURY INTERNATIONAL LLC
Est. $5,503 per month, based on comparable rentals
Sale and tax history for 1821 Pinetree Rd
Sale History
Tax History
Date
Event
Price
Stellar MLS as Distributed by MLS Grid #O6395725
May 15, 2026
Sold
$7,164,000
$1,431/sq ft
May 6, 2026
Pending
—
May 1, 2026
Listed
$6,997,000
$1,398/sq ft
MARMLS #A11930648
Feb 17, 2026
Listing Removed
—
Jan 31, 2026
Price Changed
$7,300,000
$1,458/sq ft
Jan 27, 2026
Relisted
—
Jan 12, 2026
Relisted
—
Dec 15, 2025
Listed
$7,490,000
$1,496/sq ft
Stellar MLS as Distributed by MLS Grid #O5834105
Feb 6, 2020
Sold
$4,000,000
$799/sq ft
Jan 5, 2020
Pending
—
Jan 2, 2020
Price Changed
$4,195,000
$838/sq ft
Jan 2, 2020
Listed
$4,099,000
$819/sq ft
2018 Parade of Homes Custom Home Winner. Enjoy the best of what luxurious lakefront living has to offer in this Stylish, Modern, Smart new home in Winter Park's exclusive Via's neighborhood. This spectacular, 5-bedroom, 6.3-bath, multi-level masterpiece combines innovative contemporary design with brilliant architectural artistry, blending the latest in modern living with superior craftsmanship. Tucked away on Lake Maitland adjacent to the Isle of Sicily, this exquisite home features state-of-art technology throughout, accented by classic, elegant finishes such as custom Walnut floors, staircase, landing and interior doors, and porcelain tilework. Designed for lakefront living and entertaining inside and out, a large designer chefs kitchen includes custom cabinetry, dual dishwashers, double ovens, warming drawers, a large walk in pantry and wet bar with wine cooler. Step outside to enjoy gorgeous views of the largest lake in Winter Park's chain, and outdoor lanai including a sparkling pool, an outdoor kitchen, a gas fire pit and outdoor shower. The first floor includes a large master suite, 2 additional bedrooms, a formal dining room. glass-enclosed office, and gas fireplace. The second floor includes a den and two bedrooms with full baths. This modern Smart Home is iPad & Touch Panel integrated, including surround audio, lighting control, video doorbell with off-site answering, garage door control, voice control, retractable phantom lanai and patio screens, and interior/exterior Wi-Fi access points.
Stellar MLS as Distributed by MLS Grid #O5772377
Jun 26, 2019
Listing Removed
—
Apr 26, 2019
Price Changed
*
Mar 26, 2019
Listed
*
Stellar MLS as Distributed by MLS Grid #O5724510
Mar 12, 2019
Listing Removed
—
Mar 12, 2019
Sold
$20,000
$4/sq ft
Nov 2, 2018
Price Changed
$4,995,000
$998/sq ft
Aug 30, 2018
Price Changed
$4,999,000
$999/sq ft
Aug 2, 2018
Listed
$5,250,000
$1,049/sq ft
Stellar MLS as Distributed by MLS Grid #O5457346
Mar 20, 2017
Sold
$1,925,000
$385/sq ft
Feb 14, 2017
Pending
—
Feb 11, 2017
Relisted
—
Feb 2, 2017
Pending
—
Jan 26, 2017
Price Changed
$2,195,000
$438/sq ft
Jan 26, 2017
Relisted
—
Jan 1, 2017
Pending
—
Oct 21, 2016
Price Changed
$2,395,000
$478/sq ft
Aug 5, 2016
Listed
$2,500,000
$499/sq ft
Public Records
Jun 1, 1974
Sold
$200,000
$40/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$71,518 (+2.6%)
$2,000,000 + $2,611,860
$4,611,860
2024
$69,696 (+4.7%)
$2,000,000 + $2,611,860
$4,611,860
2023
$66,594 (+9.9%)
$2,000,000 + $2,490,140
$4,490,140
2022
$60,612 (+8.3%)
$2,000,000 + $1,944,505
$3,944,505
2021
$55,973 (+27.3%)
$2,000,000 + $1,944,505
$3,944,505
2020
$43,954 (−4.4%)
$2,000,000 + $1,548,874
$3,548,874
2019
$45,977 (+55.9%)
2018
$29,490 (+119.7%)
2017
$13,421 (+2.0%)
2016
$13,152 (−2.3%)
2015
$13,467 (−0.9%)
2014
$13,584 (+2.1%)
2013
$13,305 (+1.0%)
2012
$13,174
Public record
Public record
Zoning
Permits
Beds
5
Baths
7
Stories
2
Lot width
—
Lot depth
—
Lot size
0.56 Acres
Year renovated
2018
Sq. Ft.
4,968
Year built
2018
Style
Single Family Residential
County
Orange County
APN
302132802012180
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
R-1AAA
\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. For lakefront properties, the regulations enumerated in this section are designed to encourage and promote the construction of residential uses in a manner which minimizes the impacts on the lakes, which are among the city's greatest assets; thus, diminishing their water quality and aesthetic appeal. 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-1AAA 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
May 26, 2021 • Final
Residential gas
Gas
Pool and hot tub
Mar 12, 2021 • Final
Residential swimming pool/spa
Pool and hot tub
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
Parking Features: Circular Driveway
Garage Spaces: 2
Has Attached Garage
Has Garage
Interior
Virtual Tour
Bedroom Information
# of Bedrooms: 5
Bathroom Information
# of Full Baths (Total): 6
# of Half Baths (Total): 1
Laundry Room Information
Laundry Features: Laundry Room
Other Rooms Information
# of Rooms: 13
Fireplace Information
Has Fireplace
Fireplace Features: Family Room, Gas
Heating & Cooling
Heating Information: Central, Zoned
Cooling Information: Central Air, Zoned
Interior Features
Interior Features: Built-in Features, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Solid Wood Cabinets, Split Bedroom, Stone Counters, Walk-in Closet(s), Wet Bar
Appliances: Built-In Oven, Cooktop, Dishwasher, Gas Water Heater, Refrigerator, Tankless Water Heater, Water Purifier, Wine Refrigerator