1821 Pinetree Road, WINTER PARK, FL

$6,997,000

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5

Beds

7

Baths

5,006

Square feet

0.56

Acres

About 1821 Pinetree Road

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.

Features of 1821 Pinetree Road

MLS® # O6395725
Price $6,997,000
Sold Price $7,164,000
Bedrooms 5
Bathrooms 7.00
Full Baths 6
Half Baths 1
Square Footage 5,006
Acres 0.56
Year Built 2018
Type Residential
Sub-Type Single Family Residence
Status Sold
Taxes $71,518
Sold Date 2026-05-15

Community Information

Address 1821 Pinetree Road
Area Winter Park
Subdivision SICILIAN SHORES
City WINTER PARK
County Orange
State FL
Zip Code 32789-1514

Amenities

Parking Circular Driveway
# of Garages 2
View Water
Is Waterfront Yes
Waterfront Lake Front, Lake - Chain of Lakes
Has Pool Yes

Interior

Interior Features Built-in Features, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Walk-In Closet(s), Wet Bar
Main Bedroom Downstairs Yes
Appliances Built-In Oven, Cooktop, Dishwasher, Gas Water Heater, Refrigerator, Tankless Water Heater, Water Purifier, Wine Refrigerator
Heating Central, Zoned
Cooling Central Air, Zoned
Fireplace Yes
Fireplaces Family Room, Gas
# of Stories 2

Exterior

Exterior Features Balcony, Irrigation System, Lighting, Outdoor Kitchen, Outdoor Shower
Roof Membrane, Metal
Foundation Slab

School Information

Elementary Dommerich Elem
Middle Maitland Middle
High Winter Park High

Other Information

Date Listed May 1st, 2026
Days on Market 151
Zoning R-1AAA
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeONE LUXURY INTERNATIONAL LLC

Listing Map

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