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Cypress Landing Dr Phillips Real Estate

Welcome to the exceptional community of Cypress Landing featuring Dr. Phillips real estate. Located only ten miles from downtown Orlando, Cypress Landing has many shopping, dining, and daily necessities along Conroy Windermere Rd. Homes for sale in Dr. Phillips are valued for their central location, highly-rated schools, community resources, and enthusiastic residents. Universal Orlando is right in Dr. Phillips back yard. Highways I-4, 408, and the Floridas Turnpike are nearby with direct access to Walt Disney World, SeaWorld, and The Orlando International Airport. Orange County Schools in Dr. Phillips are highly rated, and Valencia College West Campus, offering both high school dual enrollment and continuing education, is also located nearby. 

Cypress Landing Homes for Sale

2 Properties Found. Page 1 of 1.
Photo of Listing #O6199498
MLS® # O6199498
4 Beds, 4 Baths, 3,258 Sf
Photo of Listing #O6187715
MLS® # O6187715
4 Beds, 4 Baths, 3,156 Sf

Cypress Landing is located just north of Conroy Windermere Road between Apopka Vineland Rd and Dr. Phillips Blvd. Most homes have four to five bedrooms with three to five bathrooms and attached garages. These executive-style homes have been meticulously maintained, modernized, and upgraded through the years. Standard features include gourmet kitchens with upgraded cabinetry, premium appliances, and walk-in pantries. Many homes are designed with a split floor plan where private owners' suites are tucked away from main living spaces and offer walk-in closets and a spa-style ensuite bath with dual vanities, walk-in showers, and spa tubs. Secondary bedrooms are spacious; some homes include a second primary bedroom with an ensuite. Central living spaces are light filled with vaulted ceilings and open plan designs. Outdoors pride of ownership is apparent. Homes boast lush mature landscaping, screened covered lanais, and even private backyard swimming pools. Community amenities include tennis courts, half-court basketball, and a playground. Families in Cypress Landing love having all three zoned schools within excellent proximity.

Dr. Phillips is home to the elegant dining of Restaurant Row and the excitement and entertainment of I drive and Universal. The Grove, only a short drive along Conroy Windermere Rd, has a Publix supermarket, a fitness club, and an array of shopping and dining. Shadow Bay Park offers a full-service tennis center, hiking trails, picnic facilities, and playgrounds. Bill Frederick Park includes a water play area, picnic facilities, canoe rentals, walking trails, and multiple playgrounds.
Cypress Landing is a highly desirable community in a sought-after location in the heart of Southwest Orlando. Take advantage of an opportunity to schedule a private viewing and see for yourself all that makes Cypress Landing special.

Cypress Landing Community Information

  • Location: Conroy Windermere Rd & Winding Lakes Cir
  • Number of Homesites: 225 Single-family homes
  • Year(s) Built: 1994 - 2001
  • HOA: Yes
  • Square Footage: 2,100 - 4,000+
  • Community Amenities: Tennis Courts, Sports Court, Playground

Orange County Public Schools

  • Windy Ridge: Grades Pre-K - 8th Distance: 1 mile
  • Chain of Lakes Middle School: Grades 6th - 8th Distance: 1 mile
  • Olympia High School: Grades 9th - 12th Distance: 1 mile

Dining and Shopping

  • The Fresh Market - Distance: .1 miles
  • The Grove with Publix, dining, retail, professional services and medical - Distance: 1 mile
  • Walmart Neighborhood Market - Distance: 1 mile
  • MetroWest Village with Publix and pet supermarket - Distance: 2.5 miles
  • Restaurant Row - Distance: 3.5 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 4.5 miles
  • Orlando International Premium Outlets - Distance: 4 miles
  • Downtown Orlando - Distance: 10 miles

Parks and Recreation

  • Shadow Bay Park - Distance: 1.5 miles
  • Bill Fredrick Park and Pool - Distance: 1.5 miles
  • Dr. Phillips YMCA Family Center - Distance: 2.5 miles
  • MetroWest Golf Club - Distance: 2.5 miles
  • Fun Spot - Distance: 4.5 miles
  • SeaWorld - Distance: 7.5 miles
  • Universal Orlando Resort - Distance: 4 miles
  • Walt Disney World Resort - Distance: 9.5 miles


  • Orlando Health - Dr. Phillips Hospital - Distance: 6 miles
  • Advent Health Winter Garden - Distance: 8.5 miles
  • CareSpot Urgent Care Orlando - MetroWest - Distance: 4 miles


  • Orlando International Airport - Distance: 19 miles

*Distances are approximately measured from the Cypress Landing community entrance.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on May 23rd, 2024 at 4:50pm EDT.