Paul Giles
COMPASS FLORIDA LLC
(321) 415-5436
92 Total Sales
5 in Winter Park
$225K - $825K Price Range
Estimated Value: $3,674,000 - $4,566,000
Welcome to an exquisite 3-bedroom, 5.5-bath plus office pool home in the heart of Winter Park. Set back 150 feet from the picturesque brick street, this stunning residence offers unparalleled privacy and elegance, exuding sophistication from the moment you arrive. Stately double-front doors open into a grand foyer with direct views of the beautiful pool and meticulously landscaped backyard. Step inside to discover a magnificent custom concrete and iron staircase that sets the tone for the remarkable craftsmanship throughout the home. The spacious open kitchen overlooks the family room and breakfast area, providing seamless access to the covered lanai. Outfitted with sleek European custom cabinetry by NEFF, double islands, two dishwashers, and top-of-the-line Wolf/Subzero/Miele appliances, the kitchen is a chef’s dream with ample storage for all your needs. The inviting family room features a stunning gas fireplace, coffered ceilings, and a large custom bar complete with a wine refrigerator. Designed for grand entertaining, the home offers large-scale rooms with soaring ceilings that create an open and airy ambiance. The formal living and dining areas are enhanced by large picture windows that bathe the rooms in natural light, offering picturesque views of the sprawling grounds. The outdoor living space is nothing short of extraordinary, featuring a cozy outdoor living room with a gorgeous gas fireplace, a dining area, and a built-in grill. Motorized screens open to reveal the pool and manicured backyard, creating an idyllic setting for relaxation and entertainment. The primary suite on the first floor is a sanctuary of luxury, offering two separate baths, each with its walk-in closet and access to the pool area. An elegant office or optional fourth bedroom and a secondary bedroom with an en-suite bath are also on the first floor. Upstairs, you'll find a secondary primary suite with a spacious en-suite bath, featuring dual vanities, a luxurious spa-like soaking tub, and a glass-enclosed shower. For added convenience, there’s an upstairs wet bar perfect for refreshments, alongside ample cabinetry providing extra storage and space for hanging clothes. Additional features include a full-house generator, well irrigation system, a five-zone A/C system for optimal climate control, and a three-car attached garage with a brick paver-gated driveway leading to a motor court, ensuring ample parking and privacy. This truly unique property has been done and maintained to the highest standards, offering an unparalleled lifestyle. Situated in a top-notch location, just a short distance from vibrant shopping and restaurants on Park Avenue and the iconic Winter Park Golf Course, this home is a rare opportunity to experience the epitome of luxury living in Winter Park.
Last Agent to Sell the Property
PREMIER SOTHEBY'S INTL. REALTY Brokerage Phone: 407-644-3295 License #525290 Listed on: 08/28/2024
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Paul Giles
COMPASS FLORIDA LLC
(321) 415-5436
92 Total Sales
5 in Winter Park
$225K - $825K Price Range
Freddie Crespo
INVESTORS REAL ESTATE LLC
(321) 926-9610
79 Total Sales
3 in Winter Park
$244K - $435K Price Range
Bethanne Baer
BEAR TEAM REAL ESTATE
(689) 209-1739
214 Total Sales
1 in Winter Park
$375,000 Price
Ariel Vargas
EXP REALTY LLC
(321) 320-9671
484 Total Sales
4 in Winter Park
$155K - $730K Price Range
John Gomez
EXP REALTY LLC
(321) 989-6839
66 Total Sales
1 in Winter Park
$425,000 Price
Corey Lott
NEXTHOME LOTT PREMIER REALTY
(689) 219-5542
76 Total Sales
1 in Winter Park
$410,000 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 | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $3,625,000 | None Listed On Document | ||
| Dupee Paul | $2,900,000 | None Listed On Document | |
| Holler Juliette A | $2,200,000 | Attorney | |
| Brooks Murray J | $100 | -- |
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 | Borrower | Loan Amount |
|---|---|---|---|
| Previous Owner | $656,250 | ||
| Previous Owner | Dupee Paul R | $1,500,000 | |
| Previous Owner | Builder John Lindsay | $1,000,000 |
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 |
|---|---|---|---|---|---|
| 02/07/2025 02/07/25 | Sold | $3,625,000 | -8.2% | $783 / Sq Ft | |
| 01/18/2025 01/18/25 | Pending | -- | -- | -- | |
| 11/09/2024 11/09/24 | For Sale | $3,950,000 | +9.0% | $854 / Sq Ft | |
| 10/28/2024 10/28/24 | Off Market | $3,625,000 | -- | -- | |
| 10/03/2024 10/03/24 | Price Changed | $3,950,000 | -4.8% | $854 / Sq Ft | |
| 08/28/2024 08/28/24 | For Sale | $4,150,000 | +43.1% | $897 / Sq Ft | |
| 09/29/2021 09/29/21 | Sold | $2,900,000 | 0.0% | $627 / Sq Ft | View Prior Sale |
| 08/16/2021 08/16/21 | Pending | -- | -- | -- | |
| 08/13/2021 08/13/21 | For Sale | $2,900,000 | +31.8% | $627 / Sq Ft | |
| 05/26/2015 05/26/15 | Off Market | $2,200,000 | -- | -- | |
| 10/02/2012 10/02/12 | Sold | $2,200,000 | -- | $475 / Sq Ft | View Prior Sale |
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 | $43,771 | $3,749,880 | $858,000 | $2,891,880 |
| 2025 | $43,771 | $3,797,270 | $858,000 | $2,939,270 |
| 2024 | $41,080 | $2,825,026 | ||
| 2023 | $41,080 | $2,662,858 | $0 | $0 |
| 2022 | $39,335 | $2,585,299 | $780,000 | $1,805,299 |
| 2021 | $28,850 | $1,868,501 | $0 | $0 |
| 2020 | $27,772 | $1,842,703 | $0 | $0 |
| 2019 | $28,751 | $1,801,274 | $0 | $0 |
| 2018 | $28,622 | $1,767,688 | $0 | $0 |
| 2017 | $28,404 | $1,838,576 | $780,000 | $1,058,576 |
| 2016 | $27,840 | $1,808,211 | $780,000 | $1,028,211 |
| 2015 | $28,509 | $1,797,919 | $761,000 | $1,036,919 |
| 2014 | $28,759 | $1,684,410 | $500,000 | $1,184,410 |
Seller's Agent in 2025
Mick Night
PREMIER SOTHEBY'S INTL. REALTY
(407) 718-1527
280 Total Sales
Buyer's Agent in 2025
Rhonda Chesmore
KELLY PRICE & COMPANY LLC
(407) 468-6500
45 Total Sales
Seller's Agent in 2021
Vonda Fields
CHARLES RUTENBERG REALTY ORLANDO
(321) 438-6906
112 Total Sales
Seller's Agent in 2012
Nancy Bagby
FANNIE HILLMAN & ASSOCIATES
(407) 644-1234
85 Total Sales
Buyer's Agent in 2012
Pamela Stewart
PALMANO GROUP RE BROKERAGE LLC
(407) 923-2999
10 Total Sales
Source: Stellar MLS
MLS Number: O6236795
APN: 05-2230-9398-00-092
Ask me questions while you tour the home.