Impeccably cared for and ready for its next chapter, this Winter Park home blends timeless charm with essential modern updates. The property features a premium paver driveway, double-pane windows, offering both curb appeal and efficiency. Inside, the home has been kept in clean original condition, reflecting years of consistent maintenance and pride of ownership. Major systems have been thoughtfully updated, including a new electrical panel (2024), roof (2018), PEX piping, a water heater (2018), and an AC system (2017). The before mentioned double-pane windows are thoughtfully dressed with plantation shutters for added comfort and privacy throughout. There are two separate living spaces as well as a formal dining, in addition to a wood burning fireplace that centers the kitchen and informal eating and living areas, all dressed with crown molding. Outside, a new vinyl fence enhances the backyard, creating the perfect space for privacy and entertaining. With important improvements already addressed, this property provides a solid foundation for future personalization while remaining comfortable and fully livable as is. A wonderful opportunity to own a well-maintained home in a desirable Seminole County Winter Park location.
Sold for $390,000 on 10/27/25
Zestimate®
$390,000
5346 Cypress Dr, Winter Park, FL 32792
3beds
1,670sqft
Single Family Residence
Built in 1976
9,408 Square Feet Lot
$390,000 Zestimate®
$234/sqft
$2,251 Estimated rent
Owner options
What's special
Zillow last checked: 8 hours ago
Listing updated: October 27, 2025 at 01:34pm
Listing Provided by:
Kristy Kesterson 407-535-8789,
KELLER WILLIAMS ADVANTAGE REALTY 407-977-7600
Bought with:
Jennifer Rigsby, 3296067
WEMERT GROUP REALTY LLC
Source: Stellar MLS,MLS#: O6333715
Originating MLS: Orlando Regional

Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Dishwasher, Microwave, Range, Refrigerator
- Laundry: In Garage
Features
- Ceiling Fan(s), Crown Molding, Primary Bedroom Main Floor, Thermostat
- Flooring: Carpet, Ceramic Tile, Laminate
- Windows: Window Treatments
- Has fireplace: Yes
- Fireplace features: Living Room, Wood Burning
Interior area
- Total structure area: 2,274
- Total interior livable area: 1,670 sqft
Property
Parking
- Total spaces: 2
- Parking features: Garage - Attached
- Attached garage spaces: 2
Features
- Levels: One
- Stories: 1
- Exterior features: Lighting, Private Mailbox, Rain Gutters
Lot
- Size: 9,408 sqft
Details
- Parcel number: 3421305DG00002060
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1976
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Water Connected
Community & neighborhood
Location
- Region: Winter Park
- Subdivision: WRENWOOD HEIGHTS UNIT 2
HOA & financial
HOA
- Has HOA: No
Other fees
- Pet fee: $0 monthly
Other financial information
- Total actual rent: 0
Other
Other facts
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Road surface type: Paved
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Estimated market value
$390,000