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5334 Cypress Dr, Winter Park, FL 32792

PENDING $415,000
Charming single-story home featuring a well-manicured lawn and lush green landscaping at 5334 Cypress Dr, Winter Park, FL 32792

  • Bedrooms

    4

  • Baths

    2

  • Sq. Feet

    1734

  • Year Built

    1976

  • Days On Market

    16

  • $/SqFt

    $239

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37 Photos

  • Charming single-story home featuring a well-manicured lawn and lush green landscaping at 5334 Cypress Dr, Winter Park, FL 32792
  • Single-story home with lush green lawn and mature trees, offering shade and curb appeal at 5334 Cypress Dr, Winter Park, FL 32792
  • Home exterior with spacious driveway and green garage door, showcasing a well-maintained property at 5334 Cypress Dr, Winter Park, FL 32792
  • Inviting front entrance featuring a charming green double door with glass panels and a sidelight window at 5334 Cypress Dr, Winter Park, FL 32792
  • Spacious living room featuring beautiful laminate floors and neutral walls at 5334 Cypress Dr, Winter Park, FL 32792
  • Bright and airy living room with laminate flooring and a large window providing ample natural light at 5334 Cypress Dr, Winter Park, FL 32792
  • Open-concept living area featuring laminate floors and seamless transition to kitchen and dining spaces at 5334 Cypress Dr, Winter Park, FL 32792
  • Living space showcasing laminate flooring and a large window with an exterior view and neutral paint at 5334 Cypress Dr, Winter Park, FL 32792
  • Light-filled living space with laminate floors, large window, and a view of the exterior, offering ample natural light at 5334 Cypress Dr, Winter Park, FL 32792
  • Functional kitchen with an island, oak cabinets, and white appliances, perfect for meal preparation at 5334 Cypress Dr, Winter Park, FL 32792
  • Traditional kitchen features wooden cabinets, an island, modern appliances, and neutral countertops at 5334 Cypress Dr, Winter Park, FL 32792
  • Bright kitchen features wood cabinets, white appliances, and neutral countertops, with natural light at 5334 Cypress Dr, Winter Park, FL 32792
  • Kitchen with an island and wood cabinets, featuring granite countertops and a tile floor at 5334 Cypress Dr, Winter Park, FL 32792
  • View of kitchen island with cabinets and granite countertops and a tiled floor at 5334 Cypress Dr, Winter Park, FL 32792
  • Spacious living room with hardwood floors, ceiling fan, and multiple doorways at 5334 Cypress Dr, Winter Park, FL 32792
  • Open-concept living room and kitchen area with sliding glass doors to a patio at 5334 Cypress Dr, Winter Park, FL 32792
  • Hardwood floors in the living room with a view of the kitchen and enclosed patio at 5334 Cypress Dr, Winter Park, FL 32792
  • Open-concept living area featuring hardwood floors, a ceiling fan, and sliding glass doors to patio at 5334 Cypress Dr, Winter Park, FL 32792
  • Bright sunroom with large sliding doors, a ceiling fan, and backyard views at 5334 Cypress Dr, Winter Park, FL 32792
  • Bedroom with hardwood floors, a ceiling fan, sliding glass doors and a closet at 5334 Cypress Dr, Winter Park, FL 32792
  • Bright bedroom featuring hardwood floors, a ceiling fan, and a window with light-filtering curtains at 5334 Cypress Dr, Winter Park, FL 32792
More Photos \/
  • Spacious bedroom with hardwood floors, double closets, and an adjacent sink and vanity area at 5334 Cypress Dr, Winter Park, FL 32792
  • Bathroom featuring a vanity, sink, and ample cabinet space, with a view into the adjacent toilet and shower room at 5334 Cypress Dr, Winter Park, FL 32792
  • Cozy bathroom with toilet, shower, towel rack, and small window, designed for functionality and privacy at 5334 Cypress Dr, Winter Park, FL 32792
  • A partial view from the shower looking into the bedroom, featuring a vanity and hardwood floors at 5334 Cypress Dr, Winter Park, FL 32792
  • Bright bedroom with neutral walls, hardwood floors, and a window overlooking the backyard at 5334 Cypress Dr, Winter Park, FL 32792
  • Clean bathroom with white vanity, toilet, and tub/shower combination, offering a functional and tidy space at 5334 Cypress Dr, Winter Park, FL 32792
  • Minimalist bedroom with hardwood floors, ceiling fan, and a window view, creating a blank canvas for personalization at 5334 Cypress Dr, Winter Park, FL 32792
  • Bright bedroom with hardwood floors and a view of the outdoors, creating a serene and inviting space at 5334 Cypress Dr, Winter Park, FL 32792
  • Enclosed patio area perfect for outdoor entertaining, featuring screened windows and access to the backyard at 5334 Cypress Dr, Winter Park, FL 32792
  • Bright and spacious patio with white walls, sliding glass doors, and stylish lighting at 5334 Cypress Dr, Winter Park, FL 32792
  • Green backyard featuring a covered patio, white vinyl fence, and well-manicured lawn at 5334 Cypress Dr, Winter Park, FL 32792
  • Expansive backyard with lush green grass, a white vinyl fence, and a covered patio at 5334 Cypress Dr, Winter Park, FL 32792
  • Well-maintained backyard with green grass, white fencing, and a cozy screened-in patio at 5334 Cypress Dr, Winter Park, FL 32792
  • Home's exterior features a green lawn, white siding, and a screened-in patio with string lights at 5334 Cypress Dr, Winter Park, FL 32792
  • Spacious backyard showcasing green grass, mature trees, and a screened-in patio at 5334 Cypress Dr, Winter Park, FL 32792
  • Backyard with lush green grass, mature trees, vinyl fencing and covered patio at 5334 Cypress Dr, Winter Park, FL 32792
Less Photos /\

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Home Description

Meticulously maintained 4-bedroom, 2-bath concrete block home in desirable Winter Park, lovingly cared for by the same owners for 37 years. Upgrades include a remodeled kitchen, updated master and guest baths, double-pane windows, and re-piping (2014). HVAC and electrical panels replaced in 2016. Roof, screen porch, and patio updated in 2022. Enjoy the beautifully landscaped backyard with St. Augustine grass, white vinyl fencing, and a spacious screened porch. Side-entry garage offers ample space for RV or boat parking. Don’t miss this opportunity—schedule your private tour today!

  • Elementary School: Eastbrook Elementary
  • Middle School: Tuskawilla Middle
  • High School: Lake Howell High
  • Private Pool: False
  • Water Feet: 0
  • Interior Features: Ceiling Fans(s),Split Bedroom
  • Appliances: Dishwasher,Dryer,Microwave,Range,Refrigerator,Washer
  • Floor Covering: Ceramic Tile,Laminate,Vinyl
  • Kitchen Features: Granite Counters
  • Exterior Features: Sidewalk
  • Exterior Contruction: Block
  • Foundation: Slab
  • Front Exposure: East
  • Roof: Shingle
  • Building Sqft: 2321

Approximate Room Sizes / Descriptions

Family Room13x17First
Living Room15x13FirstLaminate
Balcony/Porch/Lanai11x18FirstConcrete
Balcony/Porch/Lanai9x18FirstConcrete
Kitchen10x12FirstVinyl
Den9x12FirstLaminate
Primary Bedroom13x14FirstLaminate
Bedroom 210x11FirstLaminate
Bedroom 311x12FirstLaminate
Bedroom 412x13FirstLaminate
  • Attached Garage: True
  • Garage: True
  • Garage Spaces: 2
  • Carport: False
  • Carport Spaces: 0
  • Air Conditioning: Attic Fan,Central Air
  • Heating: Central
  • Utilities: BB/HS Internet Available,Cable Connected
  • Lot Sqft: 10659.00
  • Lot Dim: 95x112
  • Lot Acres: 0.2400
  • Total Acre: 0 to less than 1/4
  • Lot Num: 208
  • Senior Community: False
  • Style: Single Family Residence
  • Building Num Floors: 1
  • : 407-622-2122

Neighborhood

The average asking price of a 4 bedroom Winter Park home in this zip code is $664,803 (60.2% more than this home).

This home is priced at $239/sqft, which is 22.4% less than similar homes in the 32792 zip code.

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Financial

  • Approx Payment:$2,019*
  • Taxes:$1,567

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at (407) 718-3706 and speak with one of our real estate consultants.

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Listing Courtesy of CHARLES RUTENBERG REALTY ORLANDO.

5334 Cypress Dr, Winter Park FL is a single family home of 1734 sqft and is currently priced at $415,000 . This single family home has 4 bedrooms. A comparable home for sale at 3901 Woodglade Cv in Winter Park is listed at $544,000. In addition to single family homes, EasyStreet also makes it easy to find Homes, Condos, New Homes and Foreclosures in Winter Park, FL. Woodcrest, Eastgate and Bear Gully Forest are nearby neighborhoods. MLS O6318457 has been posted on this site since 6/14/2025 (today).

2025 6/30/2025.

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