Alexa Monasterio Flores
Keller Williams Advantage II
(786) 946-5222
68 Total Sales
3 in Winter Park
$410K - $779K Price Range
Beautifully renovated and thoughtfully designed, this exceptional residence is nestled in the heart of Winter Park’s sought-after Tree Streets neighborhood. Privately behind entry gates, the home welcomes you with a picturesque front courtyard highlighted by a tranquil water feature, setting the tone for the sophisticated living experience that awaits. Expansive walls of glass and disappearing sliders flood the interiors with natural light while creating a seamless connection between indoor and outdoor living spaces, all while maintaining a remarkable sense of privacy. Designed for both everyday living and effortless entertaining, the open-concept floor plan showcases a spectacular custom entertainment bar featuring a stunning stone countertop, handcrafted cabinetry, an ice maker, a wine tower and a beverage cooler. The great room, dining area and kitchen flow together in one expansive space, framed by pocketing glass doors on both sides that open completely to the front courtyard and the rear lanai, pool and backyard beyond. The chef’s kitchen is a true centerpiece, outfitted with an impressive suite of Wi-Fi-enabled Thermador appliances, including a six-burner gas range with a steam oven and warming drawer and an integrated refrigerator with freezer drawers and additional refrigerated storage drawers. Thoughtfully designed for both functionality and style, the kitchen also features an appliance garage, a dedicated coffee bar, custom cabinetry and a large pass-through window that pockets into the wall, providing convenient service access to the covered lanai. A fully equipped secondary kitchen and butler’s pantry offers abundant storage, a built-in oven, a microwave and an additional refrigerator, making entertaining on any scale effortless. Privately situated on the first floor, the luxurious primary suite serves as a peaceful retreat with direct access to the lanai and outdoor living areas. The spa-inspired primary bath features a sculptural stone soaking tub, an oversized shower with multiple rain shower heads and a secluded outdoor patio complete with an open-air shower. A beautifully customized walk-in closet completes the suite. Additional first-floor amenities include a dedicated office, an elegant powder bath, and a unique dog room. A versatile flex space currently utilized as a spa room with laundry offers endless possibilities as a fitness room, expansive mudroom, storage area or wellness retreat, with direct access to one of the garage bays. The second level features a spacious family room along with two generously sized bedroom suites, each offering walk-in closets and private ensuite baths. One of the home's most remarkable features is the expansive rooftop balcony, complete with a gas fireplace and panoramic views overlooking both the front courtyard and backyard. Whether hosting guests or enjoying a quiet evening sunset, this elevated outdoor living space provides an unforgettable setting. Situated on a sprawling half-acre lot, the property offers exceptional outdoor space with room for future expansion or simply enjoying the privacy and beauty of the backyard, pool and lanai. Ideally located just minutes from vibrant Park Avenue, residents enjoy convenient access to Winter Park’s renowned dining, shopping, parks and cultural amenities, while major roadways provide easy commutes to downtown Orlando, Orlando Executive Airport and Orlando International Airport.
Last Agent to Sell the Property
PREMIER SOTHEBY'S INTL. REALTY Brokerage Phone: 407-644-3295 License #525290 Listed on: 06/05/2026
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Alexa Monasterio Flores
Keller Williams Advantage II
(786) 946-5222
68 Total Sales
3 in Winter Park
$410K - $779K Price Range
Milton James
COLDWELL BANKER REALTY
(689) 204-2693
220 Total Sales
6 in Winter Park
$78K - $537K Price Range
Brian Carboy
WEICHERT REALTORS-HALLMARK PR
(863) 271-7279
26 Total Sales
1 in Winter Park
$300,000 Price
Yusuf Gencay
RE/MAX Town & Country Realty
(844) 969-3453
38 Total Sales
2 in Winter Park
$217K - $291K Price Range
Sue Smith
RE/MAX CENTRAL REALTY
(352) 888-5813
101 Total Sales
1 in Winter Park
$661,000 Price
Terrie White
GREENE REALTY OF FLORIDA LLC
(386) 414-7424
134 Total Sales
1 in Winter Park
$338,000 Price
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $2,371,600 | First American Title Insurance | |
| Warranty Deed | $1,650,000 | Central Florida Title Llc |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $1,896,800 | New Conventional | |
| Previous Owner | $417,000 | New Conventional | |
| Previous Owner | $550,000 | New Conventional | |
| Previous Owner | $250,000 | Credit Line Revolving | |
| Previous Owner | $200,000 | New Conventional |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 07/15/2026 07/15/26 | Sold | $2,875,000 | -7.1% | $650 / Sq Ft | |
| 06/11/2026 06/11/26 | Pending | -- | -- | -- | |
| 06/05/2026 06/05/26 | For Sale | $3,095,000 | +30.5% | $699 / Sq Ft | |
| 09/12/2024 09/12/24 | Sold | $2,371,600 | -8.8% | $536 / Sq Ft | View Prior Sale |
| 08/11/2024 08/11/24 | Pending | -- | -- | -- | |
| 07/12/2024 07/12/24 | For Sale | $2,600,000 | +57.6% | $588 / Sq Ft | |
| 06/27/2018 06/27/18 | Sold | $1,650,000 | -7.8% | $373 / Sq Ft | View Prior Sale |
| 05/03/2018 05/03/18 | Pending | -- | -- | -- | |
| 02/02/2018 02/02/18 | For Sale | $1,790,000 | -- | $405 / Sq Ft |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2026 | $32,133 | $2,045,810 | $520,000 | $1,525,810 |
| 2025 | $32,133 | $2,069,220 | $520,000 | $1,549,220 |
| 2024 | $23,339 | $1,972,320 | $520,000 | $1,452,320 |
| 2023 | $23,339 | $1,511,630 | $0 | $0 |
| 2022 | $22,065 | $1,467,602 | $0 | $0 |
| 2021 | $21,853 | $1,424,856 | $0 | $0 |
| 2020 | $21,034 | $1,405,183 | $500,000 | $905,183 |
| 2019 | $22,396 | $1,411,768 | $500,000 | $911,768 |
| 2018 | $17,848 | $1,116,971 | $0 | $0 |
| 2017 | $17,708 | $1,199,367 | $422,300 | $777,067 |
| 2016 | $17,354 | $1,163,271 | $410,000 | $753,271 |
| 2015 | $17,771 | $1,154,211 | $394,000 | $760,211 |
| 2014 | $17,926 | $1,055,603 | $300,000 | $755,603 |
Seller's Agent in 2026
Mick Night
PREMIER SOTHEBY'S INTL. REALTY
(407) 718-1527
284 Total Sales
D
Buyer's Agent in 2026
Drew Henner
PREMIER SOTHEBY'S INTL. REALTY
(407) 406-0662
86 Total Sales
Seller's Agent in 2024
Thomas Nickley
KELLER WILLIAMS REALTY AT THE PARKS
(407) 233-5920
877 Total Sales
Seller Co-Listing Agent in 2024
Jason Koster
KELLER WILLIAMS REALTY AT THE PARKS
(407) 480-9452
88 Total Sales
Buyer's Agent in 2024
Giovanni Fernandez
NATIONAL REAL ESTATE
(407) 203-6903
195 Total Sales
Seller's Agent in 2018
Lois Cox-Bonacci
FOLIO REALTY LLC
(407) 687-9075
32 Total Sales
Source: Stellar MLS
MLS Number: O6414263
APN: 32-2130-1708-05-080
Ask me questions while you tour the home.