Homes In Orlando For Sale Search
$1,800,000
5 Beds ⋅ 5 Baths ⋅ Osceola Shores Sec 02 SubDv. ⋅ 32789 Zip Code
Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers market and so much more. A beautiful contemporary style home with modern interior finishes. Featuring an open floor plan, 5 bedrooms, 4.5 baths, a loft/flex space, media room, 2 study areas, front porch, back patio, lanai and so much more. Corner lot and privacy. Engineered hard wood floors through out the house and tile in utility rooms. 2 laundry rooms for convenience, located on 1st and 2nd floor of the home. Private backyard setting, a very large pool, an outdoor entertainment area featuring a kitchen and a fireplace and a screened in lanai. Metal Roof with Solar panels. A gas stove with large island and lots of space for entertainment. This home has a lot to offer in the most desirable location. Schedule your showing today.

281 Brewer Avenue, Winter Park
$2,500,000
5 Beds ⋅ 6 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code
Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home residence offers an enviable blend of timeless architecture and modern refinement. The interior has been updated and maintained to the highest standards. The home’s open-concept floor plan is anchored by rich, newer solid wood flooring and elegant plantation shutters throughout. At the heart of the home, the chef’s kitchen is a culinary masterpiece featuring, pristine quartz countertops, high-end stainless steel Bosch appliances, natural gas range, double ovens, and a walk-in pantry. A sophisticated entertainer’s bar area off the kitchen is equipped with a 100+ bottle dual-zone wine cooler, beverage cooler, ice maker, and service sink. This area is open to the kitchen an living areas for easy entertaining or catering. The newly reimagined primary retreat is a spa-like sanctuary, showcasing white marble tile, a frameless glass shower with dual rainfall heads, a deep garden soaking tub, double vanity areas with new quartz counter tops, new mirrors and lighting and a bespoke walk-in closet. The primary walk in closet was just updated with a top of the line shelving and storage system for easy organization. The home's floor plan is thoughtfully designed for flexibility, featuring a second primary suite on the main level. Back upstairs, you will find three additional guest bedrooms and two additional full bathrooms, a versatile bonus/flex room over the garage and a private balcony offering serene lake views. The bonus room has endless possibilities and can be used as a recreation room, movie theatre, exercise room, play room, or in-law/nanny quarters as the second back staircase could be a private entry. Outdoor Oasis & Infrastructure Designed for seamless indoor-outdoor living, the rear grounds feature a covered lanai over looking the pool. The covered lanai offers a living and dining area, a newly built-in outdoor kitchen with a professional grill, and a paver-lined patio surrounding a sparkling pool and gas fire pit gazebo sitting area on the other side of pool area. Plenty of yard space to throw the football, practice soccer skills or throw the frisbee with fido!! Exceptional Features Include: Mechanical Integrity: Roof replaced in 2020; updated A/C systems (2016/2019); Rinnai tankless natural gas water heater, brand new primary bathroom, all bathrooms have been refreshed, recently updated kitchen, newer solid wood floors throughout. Storage & Utility: 3-car garage with extended bays for extra storage, oversized closets throughout, and two convenient staircases. Cozy Accents: 2 fireplaces with one being wood-burning and one gas. Three distinct breakfast/dining areas within the kitchen plus formal dining. This is more than a home; it is an invitation to the quintessential Winter Park lifestyle you have been dreaming of living!

450 Lakewood Drive, Winter Park
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Orange County › Winter Park › Osceola Shores

Osceola Shores, Winter Park

Osceola Shores is a neighborhood in Winter Park, in the 32789 zip code, built mostly in the 1950s. Homes are block and stucco. Most homes fall between about 2,200 and 5,300 square feet under air, the median lot is roughly half an acre, and a two car garage is standard.

Most of Osceola Shores carries no mandatory HOA.

The neighborhood was platted in four secs, which is why listings appear under Osceola Shores, Osceola Shores Sec 1, Sec 02 and Sec 03. They are one community and they trade as one market.

What the homes are

  • Built Mostly built in the 1950s, with homes from 1910 to 2022.
  • Construction Block and stucco. Shingle roofs are near universal.
  • Size Most homes fall between about 2,200 and 5,300 square feet under air.
  • Bedrooms Four bedrooms is the most common plan, then five, then three.
  • Garage A two car garage is standard.
  • Lot The median lot is roughly half an acre.
  • HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.

Where Osceola Shores is

Osceola Shores, centered at 28.600338, -81.340115. Drag to explore.
Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Osceola Shores, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving toTimeMiles
Downtown Orlando20 min7.0
Walt Disney World34 min27.0
Orlando International Airport33 min14.3
Universal Orlando27 min15.0

Public schools nearby

  • Lakemont Elementary School 5 min, 1.3 mi
  • Brookshire Elementary School 8 min, 2.1 mi
  • Winter Park High School 9 min, 2.6 mi
  • Winter Park High School, South Gate (Baldwin Park) 10 min, 3.2 mi

Private schools nearby

  • St. Margaret Mary Catholic School 5 min, 1.3 mi
  • Christian Education at Woodruff Academy 5 min, 1.3 mi

Parks and recreation

  • Dinky Dock Park 3 min, 0.7 mi
  • Charles H. Morse Park 5 min, 1.3 mi
  • Marvin Smiley Park 3 min, 0.9 mi
  • Downtown Winter Park 4 min, 1.1 mi

Groceries and errands

  • The Ancient Olive Gourmet of Winter Park 7 min, 1.3 mi
  • Greater Lifestyle Foods 4 min, 1.1 mi
  • Sprouts Farmers Market 4 min, 1.1 mi
  • Publix Super Market at Aloma Shopping Center 5 min, 1.3 mi

Nearest is not the same as zoned. The schools above are the closest ones to Osceola Shores by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Osceola Shores actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 1 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated September 2026.

Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.

What homes sold for in Osceola Shores

$1,400,000Median sale price
$388Median per square foot
106 daysMedian days to contract
1Homes sold in 12 months

Sale prices ran from $1,400,000 to $1,400,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

How buyers paid

Cash 1 sales100%

Cash was 100% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Osceola Shores, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Osceola Shores in Winter Park, Orange County, covering closed sales from 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. One record was excluded as an off-market transfer rather than an open market sale. Data believed accurate but not guaranteed; listings and closings change daily.