The Cloisters, one of Winter Park's established and sought-after communities features an ornate architectural design complemented by lush landscaping and an inviting entryway. This fourth-floor two-bedroom, one-bathroom condominium offers approximately 901 square feet with a spacious and modern living experience.

Have you been looking for a home that you can update and make it your own? This home is the perfect opportunity to live in the coveted neighborhood of WINTER PARK PINES. This four bedroom, two bath POOL home is a well-built traditional home waiting for its next owner. The ROOF was replaced in 2024 and the remaining home is waiting for your personal touch.

Step into refined lakeside living at the exclusive Lake Killarney Townhomes, where contemporary elegance meets everyday convenience.

Don’t miss this rare chance to live on the picturesque brick streets of Olde Winter Park—just minutes from Park Avenue’s premier shopping and dining.This beautifully updated 5-bedroom, 3-bath home features a spacious downstairs primary suite with stunning hardwood floors and soaring vaulted ceilings. A flexible main-level office or guest room adds versatility to the layout.

This custom 2014 built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all that Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases 4 bedrooms, 3.

Great location of this 1950's ranch home in need of love. The home sits on a nice sized corner lot in the Winter Park schools district. The vaulted ceilings with a almost floor to ceiling windows makes the home feel nice and open with tons of natural light. This charming home has 3 bedrooms, 2 bathrooms, laundry room and open floor plan living spaces.

This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Aloma Trails near downtown Winter Park and local shops, restaurants, and schools. Features include an open floor plan with tile flooring throughout the downstairs main living area. The upgraded kitchen features 42" cabinets, granite counter tops, stainless steel appliances, tiled back splash, an island, and walk-in pantry.

Move-in ready and beautifully updated, this two-story condo in the desirable Colonies Community offers 2 bedrooms and 2.5 bathrooms, with each bedroom featuring its own private en-suite bath. All bedrooms are located upstairs. While a convenient half bath is located on the first floor. The home features fresh interior paint, new flooring in many rooms, and numerous upgrades throughout.

A unique opportunity to own this Winter Park luxury corner condo unit in the gated Park West community. Resting on the corner of New York Avenue & Carolina, with direct 2nd floor balcony views of Central Park and Park Avenue and walking proximity to the quintessential Winter Park experience.

Welcome to your dream home in the heart of Winter Parks sought after Hyde Park community. Situated at the end of a quiet cul de sac, this charming home offers 4 Bedrooms, 2.5 Baths with 1906 sf of comfort and character.. Step inside to find some fresh interior paint, vaulted ceilings, and a cozy, brick-accented fireplace that creates a warm and inviting atmosphere.

This rental is AVAILABLE for move in May 18th 2025! Welcome to Winter Park. This single family home features 2 bedrooms 1 bathroom with a 1 car detached garage. Enjoy the spacious backyard. Pet Friendly! Lawn care is included in the rent, tenant is responsible for other for other utilities. First month + 1 month security deposit required upon move in.

This charming 4 bedroom home is available now! With lots of open space, a cozy fireplace, and a walk-in closet in the primary bedroom, you will have plenty of room for the whole family. Conveniently located next to I-4, Winter Park, College Park, and just a stone's throw from downtown Orlando.