1821 Pinetree Rd

Winter Park, FL 32789

$7,490,000
Price
5
Beds
5,006 Sq. Ft.
$1,496 / Sq. Ft.
5,006
Sq. Ft.
$1,496
per Sq. Ft.
Dining
Kitchen & Pantry entry
Half Bathromm

Description

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 neighbourhood. This spectacular, 5-bedroom, 6.5-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-the-art technology throughout, accented by...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 neighbourhood. This spectacular, 5-bedroom, 6.5-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-the-art technology throughout, accented by classic, elegant finishes such as custom Walnut floors, staircase, landing and interior doors, and porcelain tile work. 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, and 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
  1. Listed by Yuri Saenz • RDS Realty, LLC

Property Details for 1821 Pinetree Road

Subdivision
Sicilian Shores
Style
WF/Pool/No Ocean Access
Waterfront
Yes
Waterfront Description
Lake Front, Lake Access
View
Lake
Area
5940 Florida Other
Geographic Area
Other Geographic Area (Out Of Area Only)
Sq Ft Total
6312
LISTING UPDATED: 01/29/2026 01:02 PM

Property Details for 1821 Pinetree Road

StatusActive
MLS #A11930648
Days on Market9
Taxes$70,845 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family / Single
Year Built2018
Lot Size-
CountyOrange County

Location

Listing Courtesy of RDS Realty, LLC, Yuri Saenz
Add your commute

Building Information for 1821 Pinetree Road

Stories2Year Built2018Building Size-Lot Size-

Payment Calculator

$42,409 per month

30 year fixed, 6.15% Interest

Principal and Interest

$36,505

Property Taxes

$5,904

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 1821 Pinetree Road

Location Information
Location Information
  • Parcel Number Free Text: 3221308020121180
  • Parcel Number MLX: 1218
  • MLS Area: 5940 Florida Other
  • Municipal Code: 32
  • Township Range: 21
  • Section: 30
  • Subdivision Number: 8020
  • Subdivision Complex Bldg: Sicilian Shores
  • Zoning Information: WP-R-1AAA
General Information
Parking
  • Num Garage Spaces: 2
  • Parking Description: Driveway
General Information
  • Front Exposure: North West
  • Housing Older Persons Act: No HOPA
  • Lot Description: 1/2 To Less Than 3/4 Acre Lot
  • Waterfront Frontage: 180
  • Water Access: Private Dock
  • Pool: Yes
  • Pool Description: Below Ground Pool, Equipment Stays, Heated
  • Pool Dimensions: 20x30
  • Design: Detached
  • Design Description: Two Story
  • Construction: Concrete Block Construction
  • Construction Type: Concrete Block Construction
  • Roof Description: Metal Roof
  • Flooring: Tile Floors, Wood Floors
  • Floor Description: Tile Floors, Wood Floors
  • Virtual Tour: https://www.propertypanorama.com/instaview/mia/A11930648
Room Information
Room Information
  • Rooms Description: Den/Library/Office, Family Room, Great Room, Utility Room/Laundry
  • Bedroom Description: At Least 1 Bedroom Ground Level, Primary Bath Tub, Sitting Area - Primary Bedroom
Additional Property Information
Utilities
  • Heating Description: Central Heat, Electric Heat
  • Cooling Description: Ceiling Fans, Central Cooling, Electric Cooling
  • Water Description: Municipal Water
  • Sewer Description: Municipal Sewer
Additional Property Information
  • Guest Accommodations: No
  • Room Count: 0
  • Interior Features: First Floor Entry, Closet Cabinetry, Cooking Island, Other Interior Features, Split Bedroom, Vaulted Ceilings, Walk-In Closets
  • Equipment Appliances: Automatic Garage Door Opener, Circuit Breaker, Trash Compactor, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Natural Gas, Electric Range, Refrigerator, Washer
  • Exterior Features: Barbeque, Built-In Grill, Deck, Exterior Lighting, High Impact Doors, Open Porch, Outdoor Shower, Patio
  • Subdivision Information: No Subdiv/Park Info
Financial Information
Financial Information
  • Type of Association: None
  • Tax Year: 2025
  • Tax Information: Tax Reflects City & County Tax
  • Special Information: As Is, Completely Renovated, Flood Zone

Property History for 1821 Pinetree Road

DateEvent & SourcePriceAppreciation
Jan 27, 2026

Listed (Active)

MiamiRE #A11930648

—
Jan 12, 2026

Temporarily Off Market

MiamiRE #A11930648

$7,490,000—
Jan 12, 2026

Listed (Active)

MiamiRE #A11930648

$7,490,000—
Jan 12, 2026

Temporarily Off Market

MiamiRE #A11930648

—
Dec 16, 2025

Temporarily Off Market

MFRMLS #J996098

—
Dec 15, 2025

Listed (Active)

MiamiRE #A11930648

$7,490,000—
Feb 6, 2020

Sold (Public Record)

Public Record #663496976

$4,000,000—
Feb 6, 2020

Sold

MFRMLS #O5834105

$4,000,000—
Jan 5, 2020

Pending

MFRMLS #O5834105

—
Jan 2, 2020

Listed (Active)

MFRMLS #O5834105

$4,099,000—
Oct 31, 2019

Withdrawn

MFRMLS #O5772377

$4,499,000—
Mar 26, 2019

Listed (Active)

MFRMLS #O5772377

$4,950,000—
Mar 12, 2019

Sold

MFRMLS #O5724510

$20,000—
Aug 2, 2018

Listed (Active)

MFRMLS #O5724510

$5,250,000—
Mar 20, 2017

Sold

MFRMLS #O5457346

$1,925,000—
Feb 14, 2017

Pending

MFRMLS #O5457346

—
Aug 3, 2016

Listed (Active)

MFRMLS #O5457346

$2,500,000—
DateEvent & SourcePrice
01/27/2026

Listed (Active)

MiamiRE #A11930648

—
01/12/2026

Temporarily Off Market

MiamiRE #A11930648

$7,490,000
01/12/2026

Listed (Active)

MiamiRE #A11930648

$7,490,000
01/12/2026

Temporarily Off Market

MiamiRE #A11930648

—
12/16/2025

Temporarily Off Market

MFRMLS #J996098

—
12/15/2025

Listed (Active)

MiamiRE #A11930648

$7,490,000
02/06/2020

Sold (Public Record)

Public Record #663496976

$4,000,000
02/06/2020

Sold

MFRMLS #O5834105

$4,000,000
01/05/2020

Pending

MFRMLS #O5834105

—
01/02/2020

Listed (Active)

MFRMLS #O5834105

$4,099,000
10/31/2019

Withdrawn

MFRMLS #O5772377

$4,499,000
03/26/2019

Listed (Active)

MFRMLS #O5772377

$4,950,000
03/12/2019

Sold

MFRMLS #O5724510

$20,000
08/02/2018

Listed (Active)

MFRMLS #O5724510

$5,250,000
03/20/2017

Sold

MFRMLS #O5457346

$1,925,000
02/14/2017

Pending

MFRMLS #O5457346

—
08/03/2016

Listed (Active)

MFRMLS #O5457346

$2,500,000

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 December 15, 2025 by RDS Realty, LLC, it's currently listed at $7,490,000. It has been on the market for a total of 9 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 makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of RDS Realty, LLC, Yuri Saenz

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: 01/29/2026 01:02 PM