1821 Pinetree Rd

Winter Park, FL 32789

$6,997,000
Price
5
Beds
5,006 Sq. Ft.
$1,398 / Sq. Ft.
5,006
Sq. Ft.
$1,398
per Sq. Ft.
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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...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.
  1. Listed by Christopher Christensen • Brokerage DRE #1073853 • ONE LUXURY INTERNATIONAL LLC
    P: (407)-312-8003 C: (407)-312-8003 chris@oneluxuryint.com
  2. Listed by Jane Peterson • Brokerage DRE #1073853 • ONE LUXURY INTERNATIONAL LLC
    P: (952)-220-0799 C: (952)-220-0799 jane@oneluxuryint.com

Property Details for 1821 Pinetree Road

Subdivision Name
SICILIAN SHORES
Township
21
Garage Spaces
2
View
Water
Waterfront
Yes
Water View
Lake, Lake - Chain of Lakes
Furnished
Unfurnished
LISTING UPDATED: 05/02/2026 02:12 PM

Property Details for 1821 Pinetree Road

StatusActive
MLS #O6395725
Days on Market5
Taxes$71,518 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2018
Lot Size0.56 AC / 24,507 SF
CountyOrange County
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Location

Listing Courtesy of ONE LUXURY INTERNATIONAL LLC, Christopher Christensen; ONE LUXURY INTERNATIONAL LLC, Jane Peterson
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Building Information for 1821 Pinetree Road

Stories2Year Built2018Building Size-Lot Size0.56 AC / 24,507 SF

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$41,193 per month

30 year fixed, 6.46% Interest

Principal and Interest

$35,234

Property Taxes

$5,960

HOA Dues

$0

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Property Information for 1821 Pinetree Road

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 5918.0
  • Building Area Units: Square Feet
  • Direction Faces: North
  • Directions: Via Tuscany to West on Via Lugano to Right on Pinetree. Home is on the Left.
  • Elementary School: Dommerich Elem
  • Middle Or Junior School: Maitland Middle
  • High School: Winter Park High
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 1821
  • Street Name: PINETREE
  • Street Suffix: ROAD
  • State: FL
  • City: WINTER PARK
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Circular Driveway
Taxes and HOA Information
  • Association: No
  • CDD: No
  • Tax Block: L
  • Tax Book Number: O-34
  • Tax Legal Description: SICILIAN SHORES O/34 LOTS 18 & 19 BLK L
  • Tax Lot: 18
  • Tax Year: 2025
Virtual Tour
Property
Lot Information
  • Additional Parcels: No
  • Parcel Number: 322130802012180
  • Total Acreage: 1/2 to less than 1
  • Water Access: Lake, Lake - Chain of Lakes
  • Water Access: Yes
  • Water Body Name: LAKE MAITLAND
  • Water Extras: No
  • Zoning: R-1AAA
  • Living Area: 5006
Property and Assessments
  • Year Built Numeric: 2018
  • Flood Zone Code: AE
  • Flood Zone Date: 09-25-2009
  • Flood Zone Panel: 12095C0255F
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 30
  • Public Survey Section: 32
  • Dock YN: Yes
  • Dock Description: Dock - Open
  • Dock Dimensions: 0
Utilities
  • Sewer: Public Sewer
  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Street Lights, Underground Utilities
  • Water Source: Canal/Lake For Irrigation, Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Stucco, Wood Frame
  • Exterior Features: Balcony, Irrigation System, Lighting, Outdoor Kitchen, Outdoor Shower
  • Foundation Details: Slab
  • Levels: Two
  • Other Structures: Outdoor Kitchen
  • Patio And Porch Features: Covered, Patio
  • Pool Features: Gunite, In Ground
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Membrane, Metal
  • Spa Features: Above Ground
  • Spa: Yes
  • Waterfront Features: Lake Front, Lake - Chain of Lakes
  • Waterfront Feet Total: 338
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 5
  • Bathrooms Full: 6
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Gas Water Heater, Refrigerator, Tankless Water Heater, Water Purifier, Wine Refrigerator
  • Cooling: Central Air, Zoned
  • Fireplace Features: Family Room, Gas
  • Fireplace: Yes
  • Flooring: Porcelain Tile, Hardwood
  • Heating: Central, Zoned
  • 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
  • Laundry Features: Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 13.0
  • Water View: Yes
  • Bathrooms Half: 1

Property History for 1821 Pinetree Road

DateEvent & SourcePriceAppreciation
May 1, 2026

Listed (Active)

MFRMLS #O6395725

$6,997,000—
Feb 17, 2026

Withdrawn

MiamiRE #A11930648

—
Jan 31, 2026

Price Change

MiamiRE #A11930648

$7,300,000—
DateEvent & SourcePrice
05/01/2026

Listed (Active)

MFRMLS #O6395725

$6,997,000
02/17/2026

Withdrawn

MiamiRE #A11930648

—
01/31/2026

Price Change

MiamiRE #A11930648

$7,300,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1821 Pinetree Road

Taxable ValueLand$2,000,000Additions$2,611,860Total$4,611,860
Tax Record2024$69,696 ($5,808 / month)
Home Facts
Beds5Total Finished SqFt4,968 SqFtAbove Grade Finished SqFt4,968 SqFtStories2Lot Size24,507 SqFtStyleSingle Family ResidenceYear Built2018ZoningR-1AAACountyORANGEAPN32-21-30-8020-12-180Fireplace TypeHas Fireplace

Schools near 1821 Pinetree Road

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Dommerich Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Maitland Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Dommerich Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Maitland Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1821 Pinetree Road, Winter Park, FL 32789

1821 Pinetree Road is a single family home for sale in Winter Park, FL 32789. This property was listed for sale on May 1, 2026 by ONE LUXURY INTERNATIONAL LLC, it's currently listed at $6,997,000. It has been on the market for a total of 5 days and was last sold on February 6, 2020. This listing's school district is Orange County Public Schools. Nearby schools include Dommerich Elementary School, Cornerstone Academy Charter and Maitland Middle School. 1821 Pinetree Road is a 5-bed, 7-bath, 5,006 sqft single family home built in 2018.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of ONE LUXURY INTERNATIONAL LLC, Christopher Christensen; ONE LUXURY INTERNATIONAL LLC, Jane Peterson

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 05/02/2026 02:12 PM