Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The

Christina Fata REAL BROKER, LLC

This is the kind of place you dream of, set on one of the most beautiful streets in Winter Park, Florida, the kind you can’t wait to come home to. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your door for morning runs, bike rides, and everything in between. This custom-built two-story residence offers 3,971 square

Melissa Johnson EXP REALTY LLC

One or more photo(s) has been virtually staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy

James Ferngren CREEGAN GROUP

Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths, an open floor plan, hardwood floors, and thoughtful updates throughout. Recent improvements include a new AC, new hot water heater, new driveway and walkway pavers, and refreshed front and backyard landscaping featuring a magnolia tree, camellias,

Kyle Grafton FANNIE HILLMAN & ASSOCIATES

A Rare Offering in Lake Eola Heights – Grand Historic Residence with Modern Renovations, Guest Suite & Private Pool SELLER IS OFFERING A $25,000 CREDIT TO THE BUYER AT CLOSING, WHICH MAY BE APPLIED TOWARD BUYER’S CLOSING COSTS, PREPAID EXPENSES, OR INTEREST RATE BUY-DOWN. SELLER FINANCING IS ALSO AVAILABLE, OFFERING ADDITIONAL FLEXIBILITY FOR QUALIFIED BUYERS. Nestled in the esteemed Lake Eola

Andre Foster EXP REALTY LLC

Offering WELL BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C,

Rene Droz, III CHARLES RUTENBERG REALTY ORLANDO

*** Parade of Homes Showcase This Weekend | Open House Saturday & Sunday 10 AM – 6 PM ***Casa Noir — Brand new construction custom home selected as a 2026 Parade of Homes showcase in Winter Park. 4 bedrooms. 4 full baths. Dedicated office. Loft. 2-car garage. Approximately 3,200 sq ft living space. Custom finishes done to perfection throughout. Inside, the foyer delivers on every promise made

Ahmad Hassan COMPASS FLORIDA LLC

Welcome to Unit 46 at Hidden Oaks, a townhome-style condo nestled in one of Winter Park's most convenient and well-established communities. Ideal for first-time buyers, down-sizers, or investors looking for location and lifestyle in one. The floor plan offers three bedrooms upstairs with two full bathrooms, plus a half bath on the main level — perfect for guests and everyday living. Two reserved

Safiya Bourne REALTY ONE GROUP EVOLVE

Welcome to this beautiful home nestled between Lake Davis and Lake Lancaster in the heart of Delaney Park! This fully renovated MID-CENTURY MODERN gem blends timeless style with modern updates. HARDWOOD FLOORS THROUGHOUT and a bright, open floor plan perfect for entertaining. The designer kitchen is a standout, showcasing wood cabinetry, QUARTZ COUNTERTOPS, stainless steel appliances, and the

Margo Rochelle WEICHERT REALTORS HALLMARK PROPERTIES

Pre-Construction. To be built. Builder is offering $8,000 toward buyer closing costs, with up to an additional $5,000 available when using the builder’s preferred lender. Pre-construction lock in pricing now. Welcome to Yucatan Gardens by CFB Homes, a modern new community in one of Orlando’s most convenient locations. This 3-bedroom plus office Coba model offers 2,216 sq ft of bright, open living

Patricia Sullivan OLDE TOWN BROKERS INC

**Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle, convenience, and

Courtney Dietch ALL REAL ESTATE & INVESTMENTS

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of refined Florida living — offering 6,396 square feet of meticulously crafted space, a private boathouse, resort-style grounds, and an address mere steps from the best of Park Avenue.From the

Kelly Price KELLY PRICE & COMPANY LLC

Pre-Construction. To be built. Spacious 5-Bedroom Pre-Construction Home in Azalea Park | Prime Location Near Downtown, Baldwin Park & Winter Park Welcome to your future home in the heart of Azalea Park—a vibrant neighborhood just 10 minutes from Downtown Orlando, Baldwin Park, and Winter Park. This brand-new 5-bedroom, 3-bath residence is designed with both comfort and style in mind, offering the

Patricia Sullivan OLDE TOWN BROKERS INC

One or more photo(s) has been virtually staged. Tucked away in a prime Orlando location, this fully renovated 3-bedroom, 2-bathroom pool home offers the perfect blend of style, space, and freedom—with NO HOA and sitting on nearly a quarter-acre fenced lot. Step inside and you’re welcomed by a bright, open living room that flows effortlessly into the heart of the home. The primary suite is a true

Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park, located in the highly sought-after Four Seasons community. This 2-bedroom, 1.5-bath unit offers 1,266 square feet of comfortable living space with a functional layout, abundant natural light, and thoughtful updates throughout. Step inside to find a spacious kitchen, renovated in 2016, featuring wood

Amy Turner KELLER WILLIAMS WINTER PARK

Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample

Karen Albright OPENDOOR BROKERAGE LLC

***MUST SEE WINTER PARK POOL HOME***Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block poolhome nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features anopen layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing kitchen

Joseph Cosgrove JAMIESON PROPERTIES, INC.

Presenting the Merida Elevation B model, a stunning 3-bedroom, 1 bonus/office, 2 bath home with an open floor plan perfect for both socializing and relaxing. The owner's suite, tucked away in the back corner for maximum privacy, features a luxurious walk-in closet. Concrete block construction, architectural shingle roofing, and a brick paver driveway leading to a spacious 2-car garage underscore

Patricia Sullivan OLDE TOWN BROKERS INC

In Orlando’s beloved Colonialtown area, this thoughtfully renovated bungalow delivers the kind of charm and character that’s becoming increasingly hard to find. From the patterned tile front porch and striking blue entry door to the warm original wood floors inside, every space feels inviting, collected, and effortlessly livable. Set on an oversized fenced homesite, 1012 N. Shine Avenue perfectly

Jill Healey KELLER WILLIAMS WINTER PARK