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Jay Holland
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$6,997,000

1821 Pinetree Road Winter Park, FL 32789 Residential - Single Family Active

  • 1821 Pinetree Road, Winter Park, FL 32789 Main Photo

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Description

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 caf?s 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.

Property Highlights

Property Type: Residential - Single Family
Cooling: Central Air, Zoned
Garage: 2 car attached
Heating: Central, Zoned
Lot Size: 0.56 Acres
Roof Type: Membrane, Metal
Stories: 2.0
Taxes: $71,518
Year Built: 2018

General Information

Bedrooms: 5
Bathrooms: 6 Full 1 Half
Sqft: 5,006
County: Orange
High School: Winter Park High
Subdivision: SICILIAN SHORES
Listed By:
Christopher Christensen ONE LUXURY INTERNATIONAL LLC 407-312-8003

Amenities

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
Balcony
Lighting
Outdoor Kitchen
Outdoor Shower

Room Information

Kitchen: 20x20
Dinette: 13x13
Living Room: 26x21
Office: 14x14
Primary Bedroom: 20x17
Bedroom 2: 13x15
Bedroom 3: 14x12
Bedroom 4: 18x14
Bedroom 5: 14x13
Loft: 16x15
Utility Room: 18x8
Dining Room: 18x16
Primary Bathroom: 22x10

Property Features

Appliances: Built-In Oven, Cooktop, Dishwasher, Gas Water Heater, Refrigerator, Tankless Water Heater, Water Purifier, Wine Refrigerator
Body of Water: LAKE MAITLAND
Community Features: Street Lights
Days on Site: 1
Directions: Via Tuscany to West on Via Lugano to Right on Pinetree. Home is on the Left.
Exterior: Stucco, Frame
Fireplace: Family Room, Gas
Fireplace Y/N: Yes
Flood Zone Code: AE
Flooring: Tile, Wood
Foundation: Slab
Frontage Lake: 169
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot Dimensions: 0.56
Other Equipment: Irrigation Equipment
Other Structures: Outdoor Kitchen
Ownership: Fee Simple
Parking: Circular Driveway
Parking Notes: Circular Driveway
Patio/Porch: Covered, Patio
Pool: Gunite, In Ground
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: 24 Hour Notice, Appointment Only, Call Listing Agent, Listing Agent Must Accompany
Spa: Above Ground
Special Sale Provisions: None
Special View Info: Water
Swimming Pool: Yes
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Underground Utilities
Water: Canal/Lake For Irrigation, Public
Water Access: Lake, Lake - Chain of Lakes
Water Access Y/N: Yes
Waterfront Features: Lake Front, Lake Privileges
Water View: Lake, Lake - Chain of Lakes
Zoning: R-1AAA
$6,997,000
5beds
6.5baths
5,006sqft
2cars
New to the Market Active
BEDS5 BATHS6 full 1 partial SQUARE FEET5,006 MLS#O6395725
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONSICILIAN SHORES

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1821 Pinetree Road, Winter Park, FL 32789.

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Estimated Payment

$ 31,600.33 per month $23,599.71 Principal & Interest $5,959.83 Property Tax $2,040.79 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 05/03/2026. The listing information on this page last changed on 05/03/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sun 05/03/2026 12:03:17 AM EST) or Stellar MLS (last updated Sat 05/02/2026 11:44:05 PM EST). Real estate listings held by brokerage firms other than Wagner Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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