Winter Park Neighborhood Guide
See Homes for Sale in some of Winter Park Better Neighborhoods Winter Park Neighborhoods- Winter Park Subdivisions- Winter Park Real Estate
Windsong, Bear Gully Pointe, Maitland Shores, Lake Knowles Terrace, Dommerich, Via area of Old Winter Park, Orwin Manor (Westminster) Located just northeast of downtown Orlando, Winter Park, with a population of about 25,000 is home to some of the area's finest homes. Founded as a resort destination by wealthy New England industrialists before the turn of the 20th century, it is recognized as the first centrally planned community in Florida. Its main street, Park Avenue, includes not only public civic buildings and fabulous shopping at specialty shops and boutiques, but also the numerous art and antique galleries, museums, a park and a train station. The city is home to Rollins College (ranked as one of "America's Best Colleges" by U.S. News and World Report), Full Sail University and the Charles Hosmer Morse Museum of American Art, which houses the largest collection of Tiffany glass. Winter Park enjoys more parks pace per capita than any other city in Florida.
 Winter Park Homes for Sale - Winter Park Luxury Homes - Winter Park Waterfront
Windsong
Located a short distance from downtown Winter Park. Access to Windsong from the north side is from Park Ave., east on Aloma Ave., south on Phelps. Access from the Southside is from Glenridge north into Preserve Point Drive. A premium community of approximately 360 homes developed in the heart of Winter Park around Lake Mizell, Lake Berry and Lake Virginia. There are five subdivisions in Windsong; Elizabeth’s Walk, Lakeside, Northshore, Preserve Point and Lookout Landing. Very convenient to Winter Park and downtown Orlando. Residents enjoy two community pools, numerous lakefront parks and playgrounds, boat dock and lake access. Tip: Great Winter Park schools. Nicely wooded rolling terrain on Winter Park chain of lakes. Highly sought after neighborhood with homes ranging in size from 3,000 square feet to estate homes of over 10,000 square feet. Stunning homes by some of the area’s best custom builders on beautifully landscaped lots with some over one acre. Some lots are still available. Prices range from $550,000 to over $7,000,000
Year homes built: 2001 - present
Approximate Association Dues: $2,500/yr
Bear Gully Pointe Located east of Winter Park in Seminole County. East of SR436 on Aloma Ave. just past Howell Branch Rd, left on Bear Gully Pointe Rd. Gated 66 home community with large lots in serene natural setting. Located convenient to major traffic arteries, Winter Park and the 417 Greeneway. Residents enjoy neighborhood park, playground and tennis courts with optional access to spring fed Bear Gully Lake. Tip: Excellent schools. Highly sought after established neighborhood. Attractive custom homes nicely landscaped adjacent to conservation area with old Florida woodlands feel. Prices range from $550,000 to over $1,000,000
Year homes built: 1991 – 1997 Approximate Association Dues: $1,500/yr
Maitland Shores Located on the northeast shore of Lake Maitland. From 17-92 east on Horatio Ave., left on Venetian Way. 150 home subdivision developed mostly in the 1950’s. Convenient to Winter Park, Maitland and major traffic arteries. Residents enjoy boat ramp and access to Lake Maitland. Tip: Great schools. Attractive older homes in established section of Winter Park. Most homes have been updated and are beautifully maintained. Because of its prime location, there have been some tear downs and large custom homes built in the area since 2000. Highly sought after section of Winter Park. Prices range from $600,000 to over $3,500,000
Year homes built: 1949 – 1959, some 2000 - present Approximate Association Dues: $70/yr (optional) Lake Knowles Terrace Located in the Northeast section of Winter Park between Lake Howell Rd and Temple Dr. north of Palmer. From Aloma Ave. north on Lakemont, left on Palmer and right on Temple Dr. An eclectic subdivision of about 450 homes that began development in the 1950’s and has continued to evolve up to the present. Located within a few minutes of Park Ave. and convenient to major traffic arteries and shopping. Residents enjoy Lake Knowles, a community park, tennis courts and the nearby Winter Park YMCA. Tip: Great schools that are close by. A nice mixture of well maintained older homes, newer homes and a variety of styles defines this sought after neighborhood. Great for families who want to be in Winter Park. Prices range from $250,000 to over $2,000,000
Year homes built: 1950 – present Approximate Association Dues: None
Dommerich Located north of Horatio/Howell Branch Rd, between Lake Minnehaha and Lake Howell Rd. From 17-92 east on Horatio left on Arapaho Trail. From Lake Howell Rd turn west on Tuscarora Trail. Established neighborhood of about 1,500 homes on large nicely wooded lots with tree lined streets. Subdivisions include Dommerich Estates, Dommerich Hills and Dommerich Woods. Very convenient to Winter Park, Maitland, 17-92 and SR436. Residents enjoy deeded access to Chain of Lakes, optional community dock, park, playground, and racquetball and tennis courts. Tip: Great schools. Middle and elementary schools are within walking distance. Highly desirable neighborhood especially for young families. Most homes were built in the 60’s and have been well maintained and many have been updated. Great location, Winter Park Schools and attractive affordable homes. The names of the streets are an added bonus. Prices range from $250,000 to $550,000 (a few up to $900,000)
Year homes built: 1957 – 1971 Approximate Association Dues: $75/yr optional
Via area of Old Winter Park Located between the eastern shore of Lake Maitland and Temple Dr. south of Howell Branch Rd... The Via area includes the subdivisions of Tuscany Oaks, Tuscany Terrace, Sicilian Shores and Lugano Terrace. A much sought after premium section of Winter Park. Convenient to Park Ave., Winter Park Racquet Club and excellent Winter Park schools. Optional deeded access and boat ramp to the Chain of Lakes. Tip: Large wooded lots with majestic oaks and beautiful homes. Attractive older homes in established section of Winter Park have been updated and are beautifully maintained. Because of its prime location, there have been some tear downs and large custom homes built in the area since 2000. Highly sought after section of Winter Park. Prices range from $450,000 – most are from $1,000,000 - $3,500,000
Year homes built: 1930 – present Approximate Association Dues: $75/yr optional Orwin Manor (Westminster) Located between Clay Ave and Orange Ave just north of their intersection near Florida Hospital. A charming nicely wooded neighborhood with tree lined streets and approximately 435 homes. Developed just after WWII these delightful bungalows have been thoroughly updated and beautifully maintained. Convenient to Winter Park, College Park, Orlando and I-4. Tip: Good schools. Safe, friendly neighborhood and fabulous location. Most are less than 2,000 square feet but they are stylish little homes that are highly sought after. Prices range from $200,000 to $400,000
Year homes built: 1945 – 1957 Approximate Association Dues: None Subdivisions of Winter Park Florida Annebury, Bear Gully Pointe, Bear Gully. Autumn Glen, Azalea Lane, Boiley Greem, Brookshire Heights, Eastbrook, Forrest Hills, Four Seasons, Hidden Oaks, Kings Cove, Lake Knowles Terrace, Lakemont Heights, The Langford, Lost Creek- Olympia Heights Annex, Orwin Manor, Quail Hollow, Sandlewood Creek, Selwyn Heights, Sylvan Heights, Sylvan Lake Shores, The Regent at Winter Park, Vistas At Lake Howell, Windsong, Elizabeth's Walk, Winter Park Estates, Winter Park Pines, Winter Woods, Woodcrest, Chateaux du Lac, College Quarter, Hannibal Square, Northwood Circle, Park Grove, The Plymouth, Sevilla, Waterbridge. Windsong, Bear Gully Pointe, Maitland Shores, Lake Knowles Terrace, Dommerich, Via area of Old Winter Park, Orwin Manor (Westminster)
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