One or more photo(s) has been virtually staged. Multiple offers received - please submit HIGHEST & BEST by THURSDAY, JULY 17th at 5:00 PM. Welcome to the most gorgeous waterfront property in Winter Park for UNDER $500,000! This charming 4 bedroom, 3 bath home is situated on a third of an acre with a stunning pool and water features overlooking a serene water view. The backyard truly must be seen to be believed! Guests will be just as captivated by the interior of this home. Discover flexibility and comfort in this beautifully designed home featuring dual primary suites — one upstairs and one down — each with its own private ensuite bath. Whether you're accommodating multi-generational living, hosting guests, or simply seeking extra privacy, this layout offers the ultimate in versatility. Thoughtfully designed living spaces and stylish finishes continue in the living spaces as well. Wood floors flow throughout the downstairs. The great room is bright and sunny from four (4) oversized windows as well as French Doors leading to the covered patio. Cooking is a delight with a newer gas stove and a kitchen overlooking the dining and living room. Storage abounds thanks to an indoor laundry room, an oversized two-car garage, and ample closet space in each bedroom. Enjoy home efficiency thanks to HVAC updates in 2023 and a tankless water heater installed in 2024. Winter Park is celebrated for its renowned shopping, dining, parks, and schools - and you could be close to it all in this home! Zoned Winter Park High School and its sports facilities are minutes away. Come discover the Winter Park lifestyle you have dreamed of. It is now obtainable in this incredible estate!
Single-familyProperty Type
1959Year Built
0.32 acresLot Size
$325Est. Price/Sq.Ft.
2 car garageParking
Listed by D'Anne Mica• FANNIE HILLMAN & ASSOCIATES
ACTIVE WITH CONTRACT. BEAUTIFUL WINTER PARK HOME, TOTALLY RENOVATED. INGROUND POOL IN WINTER PARK. 'A' RATED SCHOOL DISTRICT. SELLER IS MOTIVATED.
Public Records
Oct 17, 2002
Sold
$129,900
$69/sq ft
Public Records
Jun 1, 1968
Sold
$18,000
$10/sq ft
Public Records
Jun 1, 1966
Sold
$15,500
$8/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$6,777 (+4.2%)
$135,000 + $259,205
$394,205
2024
$6,503 (+7.8%)
$135,000 + $259,205
$394,205
2023
$6,032 (+9.0%)
$135,000 + $248,202
$383,202
2022
$5,536 (+9.3%)
$135,000 + $210,953
$345,953
2021
$5,064 (+2.3%)
$135,000 + $210,953
$345,953
2020
$4,950 (−3.7%)
$125,000 + $177,948
$302,948
2019
$5,141 (+9.5%)
$125,000 + $181,577
$306,577
2018
$4,695 (+3.3%)
$125,000 + $181,577
$306,577
2017
$4,544 (−0.5%)
$110,000 + $149,266
$259,266
2016
$4,566 (+48.6%)
$110,000 + $149,266
$259,266
2015
$3,073 (−1.7%)
2014
$3,126 (+2.2%)
2013
$3,060 (−1.0%)
2012
$3,090
Tax history for 2739 Amsden Rd
Year
Property tax
Land + Additions
Assessment*
2025
$6,777 (+4.2%)
$135,000 + $259,205
$394,205
2024
$6,503 (+7.8%)
$135,000 + $259,205
$394,205
2023
$6,032 (+9.0%)
$135,000 + $248,202
$383,202
2022
$5,536 (+9.3%)
$135,000 + $210,953
$345,953
2021
$5,064 (+2.3%)
$135,000 + $210,953
$345,953
2020
$4,950 (−3.7%)
$125,000 + $177,948
$302,948
2019
$5,141 (+9.5%)
$125,000 + $181,577
$306,577
2018
$4,695 (+3.3%)
$125,000 + $181,577
$306,577
2017
$4,544 (−0.5%)
$110,000 + $149,266
$259,266
2016
$4,566 (+48.6%)
$110,000 + $149,266
$259,266
2015
$3,073 (−1.7%)
2014
$3,126 (+2.2%)
2013
$3,060 (−1.0%)
2012
$3,090
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Beds
4
Baths
3
Stories
2
Lot width
—
Lot depth
—
Lot size
0.32 Acres
Year renovated
1969
Sq. Ft.
1,877
Year built
1959
Style
Single Family Residential
County
Orange County
APN
302204941404080
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 17, 2026.
R-1A
Single-Family Dwelling Districts
The areas included within R-1-A single-family dwelling districts are intended to be single-family residential areas with large lots and low population densities. Certain structures and uses required to serve educational, religious, utilities and noncommercial recreational needs of such areas are permitted within the districts as special exceptions.
Permitted uses
Include but are not limited to:
Livestock production
Housing-Single unit
Fire house
Police station
Property details
Parking
Parking Information
Garage Spaces: 2
Has Attached Garage
Has Garage
Interior
Virtual Tour
Bedroom Information
# of Bedrooms: 4
Bathroom Information
# of Full Baths (Total): 3
Laundry Room Information
Laundry Features: Inside
Other Rooms Information
# of Rooms: 11
Heating & Cooling
Heating Information: Central
Cooling Information: Central Air
Interior Features
Interior Features: Ceiling Fans(s), High Ceilings, Open Floorplan, Stone Counters, Thermostat, Walk-in Closet(s)
Window Features: Skylight(s), Blinds
Appliances: Built-In Oven, Dryer, Gas Water Heater, Microwave, Range, Tankless Water Heater
Flooring: Carpet, Concrete, Tile
Exterior
Building Information
Construction Materials: Block
Roof: Shingle
Exterior Features
Patio And Porch Features: Front Porch, Patio
Exterior Features: French Doors, Lighting, Rain Gutters, Storage