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Looking for lakefront homes on Lake Osceola? Find lake front real estate for sale here. Located in Orange County, Florida. Discover the best lake front listings - properties, land, and acreage to build your dream lake house, cottage or cabin on. Search for an agent who specializes in lake property to help you buy or sell a home.

Lakehouse.com has 9 lake properties for sale on Lake Osceola, as well as lakefront homes, lots, land and acreage in Winter Park. Median home price: $1,784,000, lot price: $4,500,000. 

503 N INTERLACHEN AVENUE

Acres: 0.480

JUST LISTED - RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,999,000!!! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos...

1560 WOODLAND AVENUE

5 5.0   Sf: 3851   Yr: 1990  Acres: 0.270

Welcome to a one-of-a-kind opportunity inside the Winter Park city limits, where timeless character, meaningful updates, and an exceptional lifestyle and location come together in a perfect blend!...

340 ALBERTA DRIVE

4 4.0   Sf: 3226   Yr: 2000  Acres: 0.300

Welcome to 340 Alberta Drive, a beautifully maintained 4-bedroom, 4-bath residence with a new roof installed in 2020. Situated on a spacious .30-acre lot in the heart of Winter Park, this home...

1399 ALOMA AVENUE

3 2.0   Sf: 1804   Yr: 1948  Acres: 0.190

***Price Adjustment *** Motivated Seller! Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on a private lot in the heart of Winter...

311 E MORSE BOULEVARD 7-5

1 1.0   Sf: 482   Yr: 1960  Acres: 2.770

Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown...

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311 E MORSE BOULEVARD 6-3

1 1.0   Sf: 570   Yr: 1960 

Discover your new downtown Winter Park ground-floor pied-a-terre. Two blocks from Park Avenue, the 1960s mid-century modern Whispering Waters Condominiums are a Winter Park landmark. Your remodeled...

473 FLETCHER PLACE

5 6.0   Sf: 4296   Yr: 2017  Acres: 0.310

Welcome to the best of Winter Park living, where luxury meets lifestyle and every day feels like a getaway. This stunning custom home, built by Lundev, sits on a quiet, tree-lined street just a mile...

446 ALBERTA DRIVE

4 3.0   Sf: 3263   Yr: 1968  Acres: 0.350

Under contract-accepting backup offers. Charming Opportunity in Prime Winter Park - 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only...

311 E MORSE BOULEVARD 7-2

1 1.0   Sf: 900   Yr: 1960  Acres: 2.770

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy sunrise views over Lake Osceola from this Whispering Waters jewel box, now offered at an improved price...

Showing 10 lake properties within 20 miles:

13809 Larkton Lane

5 4.0   Sf: 3231   Yr: 2024  Acres: 0.140

Welcome to luxury living in the heart of Lake Nona's most coveted gated community which includes the Eagle Creek Golf Club. This beautiful home has plenty of room to live and entertain. The chef's...

10915 Ledgement Lane

4 4.0   Sf: 2818   Yr: 2003  Acres: 0.320

Luxury Living Awaits at Glenmuir! Welcome home to 10915 Ledgement Lane, an absolutely stunning retreat nestled in the back of the highly sought-after, gated community of Glenmuir in beautiful...

Not on the List

251 W Ventris Avenue W

2 2.0   Sf: 3474   Yr: 1901  Acres: 0.350

Over a century of charm in this extraordinary Victorian home, originally built in 1901, updated with Hardi-plank concrete siding. The great room & end suite expansion was completed in 2000. Sit on...

13559 Falcon Pointe Drive

4 3.0   Sf: 2223   Yr: 1991  Acres: 0.240

One-story pool home with serene pond views in the heart of Hunters Creek. This spacious 4-bedroom, 2.5-bath home features a large floor plan ideal for everyday living or entertaining. Perfect as a...

2516 Grassy Point Drive unit: 208

1 1.0   Sf: 701   Yr: 1994  Acres: 0.010

Updated 1 bed, 1 bath condo in Lake Mary. Luxury plank vinyl flooring throughout with 5 1/4* baseboards. Upgraded AC (2021) with Wi-Fi thermostat. Newer water heater and a brand-new garbage disposal...

5758 HAMLIN GROVES TRAIL

0 0.0   Sf: 61844   Yr: 2023  Acres: 9.160

Rare Triple-Net Investment Opportunity: Flagship Leisure Anchor in America's 2nd Best-Selling Community - Hamlin/Horizon West. Own a premier 61,844-square-foot Class A commercial asset situated in...

HAMLIN SOUTHWEST

11900 LAKE BUTLER BOULEVARD

7 9.0   Sf: 10649   Yr: 2014  Acres: 3.750

Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere's largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700...

METCALF PARK REP

8822 WINTER GARDEN VINELAND ROAD

3 3.0   Sf: 2496   Yr: 1979  Acres: 4.660

Privately positioned on Lake Mabel, this rare lakefront offering includes two contiguous parcels sold together, totaling approx. 9.47+- acres, with direct lake frontage and estate-level privacy in a...

ROYAL RANCH ESTATES

8834 WINTER GARDEN VINELAND ROAD

Acres: 4.810

Privately positioned on Lake Mabel, this rare lakefront offering includes two contiguous parcels sold together, totaling approx. 9.47+- acres, with direct lake frontage and estate-level privacy in a...

ROYAL RANCH ESTATES

5525 ISLEWORTH COUNTRY CLUB DR

5 6.0   Sf: 9511   Yr: 1999  Acres: 1.020

One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club...

ISLEWORTH