Back 1821 Pinetree Rd
Off Market

1821 Pinetree Rd

Winter Park FL 32789

5
7
2
5918 sq. ft.
24507 sq. ft.
Single-Family
Last sold for $7,164,000
Christopher ChristensenChristopher Christensen, last sold this property on 15 May 2026 after 13 days on market.

Overview

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

5 bedrooms
7 bathrooms
2 carspaces
2 garage spaces
5918 sq. ft. floor area
24507 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Winter Park over the last 12 months, the estimated median property value of 1821 Pinetree Rd is $2.17m.

Median value
$2.17m
Estimated value range
$640k - $7.16m
Median days on market
70
Estimated value trend
-18%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Winter Park. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 1821 Pinetree Rd

2026
Sold
$7,164,000
15 May 2026 by Christopher Christensen, of ONE LUXURY INTERNATIONAL LLC
2020
Sold
Undisclosed
06 Feb 2020 by James Mitchell, PA, of KELLER WILLIAMS WINTER PARK
2020
Sold
$4,000,000
06 Feb 2020 by Maria Van Warner, of FANNIE HILLMAN & ASSOCIATES

Happy sellers in Winter Park

80%
80% of sellers in Winter Park reported that their sale price either exceeded or met their price expectations.

Winter Park stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 7 reviews in Winter Park over the last 12 months.

Local market activity for 5 bedroom single-family properties in Winter Park

In the last 12 months, 60 five-bedroom single-family properties similar to 1821 Pinetree Rd, have been sold.

This represents a 9% decrease in five-bedroom single-family properties sales when compared to the previous 12 months.

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