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$6,997,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 6 Full Baths
  • 1 Partial Bath
  • 5,006 Sq. Ft.
  • Updated 4 days ago
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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.

Full Property Details for 1821 Pinetree Rd

General

  • Price: $6,997,000
  • Taxes: $71,518 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6395725
  • Updated: 5/1/2026
  • Added to Site: 4 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 13
  • Interior Features: Built-in Features, High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Walk-In Closet(s), Wet Bar
  • Fireplace: Yes
  • Fireplace(s): Family Room, Gas
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Gas Water Heater, Refrigerator, Tankless Water Heater, Water Purifier, Wine Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Porcelain Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 6
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground
  • Spa: Yes
  • Spa Description: Above Ground

Exterior

  • Exterior Features: Balcony, Irrigation System, Lighting, Outdoor Kitchen, Outdoor Shower
  • Deck/Patio: Covered, Patio
  • Porch/Patio/Deck: Covered, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Circular Driveway

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: SICILIAN SHORES
  • Driving Directions: Via Tuscany to West on Via Lugano to Right on Pinetree. Home is on the Left.
  • Direction Faces: North

School Information

  • Elementary School: Dommerich Elem
  • Middle School: Maitland Middle
  • High School: Winter Park High

Community

  • Community Name: 32789 - Winter Park

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Central, Zoned

Utilities

  • Sewer: Public Sewer
  • Water District: LAKE MAITLAND
  • Water: Canal/Lake For Irrigation, Public
  • Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Street Lights, Underground Utilities

Structural Information

  • Exterior Const.: Stucco, Wood Frame
  • Roof: Membrane, Metal
  • Stories/Levels: Two
  • Square Feet: 5,006
  • Sq. Ft. Source: Public Records
  • Year Built: 2018

Additional Structures

  • Other Structures: Outdoor Kitchen

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.56
  • Lot Size (Sq. Ft.): 24,507
  • Lot Size: 24507
  • Street/Road Desc.: Asphalt

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake, Lake - Chain of Lakes
  • Water Front Name: LAKE MAITLAND
  • Water Front Desc.: Lake Front, Lake - Chain of Lakes

Financial Considerations

  • Tax Amount: $71,518
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: SICILIAN SHORES O/34 LOTS 18 & 19 BLK L
  • Flood Zone Info: AE
  • APN: 322130802012180
  • Property ID: 322130802012180
  • Block/Lot/Section: L

Listed by One Luxury International Llc

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Listing agents

— 1821 Pinetree Rd —

  • One Luxury International Llc

  • One Luxury International Llc

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 1821 Pinetree Rd

School District:Orange County School District
NameGradesDistance
Dommerich Elementary School
601 North Thistle Lane, Maitland, FL 32751
K-51.1 mi
Maitland Middle School
701 North Thistle Lane, Maitland, FL 32751
6-81.2 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-122.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1821 Pinetree Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/01/2026
Listed
$6,997,000
74.92%
MLS
2/06/2020
Sold
$4,000,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1821 Pinetree Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$71,518
—
$4,573,200
-1%
2025
$71,518
3%
$4,611,860
3%
2024
$69,696
5%
$4,490,140
4%
2023
$66,594
19%
$4,305,769
21%
2021
$55,973
-8%
$3,548,874
-10%
2022
$60,612
8%
$3,944,505
36%
2021
$55,973
22%
$2,893,471
1%
2019
$45,977
56%
$2,857,057
60%
2018
$29,490
120%
$1,781,105
112%
2017
$13,421
2%
$838,579
2%
2016
$13,152
-2%
$821,331
1%
2015
$13,468
-1%
$815,622
1%
2014
$13,585
2%
$809,149
2%
2013
$13,305
—
$797,191
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by One Luxury International Llc

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1821 Pinetree Road, Winter Park, FL 32789 (MLS# O6395725) is a Single Family property with 5 bedrooms, 6 full bathrooms and 1 partial bathroom. 1821 Pinetree Road is currently listed for $6,997,000 and was received on May 01, 2026. Want to learn more about 1821 Pinetree Road? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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