Back 699 Osceola Ave
Active

699 Osceola Ave

Winter Park FL 32789

5
4
2
5062 sq. ft.
33479 sq. ft.
Single-Family
Currently for sale - view listing

Overview

Pristine custom Mediterranean Lakefront estate, with 5 bedrooms, 3.5 bathrooms, sandy beach (one of a kind) and 127? on lake Osceola. Enjoy captivating views of lake Osceola, part of winter park chain of lakes. Professionally updated to today?s standards and modern technologies with the authentic character maintained to keep the original charm and elegance. Enter the home into a large foyer and the authentic quality of the construction is evident. The downstairs family room has spectacular cypress beams, built-ins carved out of the plaster walls, an original tiled fireplace and stunning dark hardwood floors. Also, downstairs you will find the Classically Chic Chef's Kitchen, large island, granite countertops, modern technology appliances and custom cabinetry. Kitchen is open to the family room with brand new Nana wall doors and picturesque view of the swimming pool and lake Osceola. The beautiful master retreat downstairs has walk in dressing suite for the owner?s wardrobe and a sitting space with a calm ambiance. Upstairs houses four spacious bedrooms with beautiful views of the lake. Outdoor space includes a covered lanai that has been professionally updated by well-known Phil Kean design group, surrounded by lush landscaping, a century old oak tree overlooking the sandy beach and the swimming pool is a perfect setting for entertaining family and friends. A recently renovated boat dock with power boat lift and storage closet. Enjoy the easy stroll to Park Avenue, Rollins College, and downtown winter park. Many recent upgrades ($260,000) in 2020. If you enjoy comfort, luxury and beauty call to schedule your private showing.

Features

5 bedrooms
4 bathrooms
2 carspaces
5062 sq. ft. floor area
33479 sq. ft. lot size
Single-Family

Property history for 699 Osceola Ave

2019
Sold
$2,250,000
09 Jul 2019 by Sheryl Kashuk, of FANNIE HILLMAN & ASSOCIATES
2006
Sold
$2,100,000
30 May 2006 by Kelly Price, of KELLY PRICE & COMPANY LLC

Happy sellers in Winter Park

83%
83% 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, 56 five-bedroom single-family properties similar to 699 Osceola Ave, have been sold.

This represents a 15% increase in five-bedroom single-family properties sales when compared to the previous 12 months.

© 2026 RateMyAgent