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
$390,000
5346 CYPRESS DRIVE, WINTER PARK, FL 32792
3beds
1,670sqft
Single Family Residence
Built in 1976
9,408 Square Feet Lot
$386,600 Zestimate®
$234/sqft
$2,993 Estimated rent
Home value
$386,600
$352,000 - $425,000
$2,993/mo
Zestimate® history
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$2,613/mo
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List your homeWhat's special
Two separate living spacesClean original conditionPrivacy and entertainingDouble-pane windowsWood burning fireplaceFormal diningPlantation shutters
Zillow last checked:
Listing updated:
Listed 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
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 Square Feet
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 & HOA
Community
- Pet fee: $0 monthly
- Subdivision: WRENWOOD HEIGHTS UNIT 2
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $234/sqft
- Tax assessed value: $312,357
- Annual tax amount: $1,186
- Date on market: 9/3/2025
- Cumulative days on market: 31 days
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 10/27/2025 | Sold | $390,000-4.9%$234/sqft |
Source:  Stellar MLS #O6333715 Report a problem | ||
| 10/5/2025 | Pending sale | $410,000$246/sqft |
Source: Stellar MLS #O6333715 Report a problem | ||
| 9/22/2025 | Price change | $410,000-2.4%$246/sqft |
Source: Stellar MLS #O6333715 Report a problem | ||
| 9/3/2025 | Listed for sale | $419,900$251/sqft |
Source: Stellar MLS #O6333715 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $1,270 +49.1% | $131,633 +2.9% |
| 2024 | $851 +4.9% | $127,923 +3% |
| 2023 | $812 -2.5% | $124,197 +3% |
| 2022 | $832 -23.6% | $120,580 +3% |
| 2021 | $1,090 +1.6% | $117,068 +1.4% |
| 2020 | $1,073 +1.7% | $115,452 +2.3% |
| 2019 | $1,055 | $112,856 +1.9% |
| 2018 | $1,055 +2.3% | $110,752 +2.1% |
| 2017 | $1,032 +1.5% | $108,474 +1.4% |
| 2016 | $1,016 -1.4% | $106,987 +1.4% |
| 2015 | $1,031 | $105,504 +0.8% |
| 2014 | $1,031 +27.7% | $104,667 +1.5% |
| 2013 | $807 +11% | $103,120 +1.7% |
| 2012 | $727 +1.6% | $101,396 +1.9% |
| 2011 | $716 +0.8% | $99,512 +1.5% |
| 2010 | $710 -20.7% | $98,041 +2.7% |
| 2009 | $896 +35.4% | $95,463 +0.1% |
| 2008 | $662 -14.4% | $95,368 +3% |
| 2007 | $773 -16% | $92,590 +2.5% |
| 2006 | $920 +2.9% | $90,332 +3% |
| 2005 | $894 +1.3% | $87,701 +3% |
| 2004 | $883 -11.3% | $85,147 +1.9% |
| 2003 | $995 +1.8% | $83,559 +2.4% |
| 2002 | $978 +5.4% | $81,601 +4.6% |
| 2000 | $928 | $77,977 |
Find assessor info on the county website
Neighborhood: Goldenrod
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Nearby schools
GreatSchools rating
- 7/10Eastbrook Elementary SchoolGrades: PK-5Distance: 0.3 mi
- 8/10Tuskawilla Middle SchoolGrades: 6-8Distance: 2.1 mi
- 7/10Lake Howell High SchoolGrades: 9-12Distance: 1.9 mi
Schools provided by the listing agent
- Elementary: Eastbrook Elementary
- Middle: Tuskawilla Middle
- High: Lake Howell High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$386,600
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$386,600
- Florida
- Seminole County
- Winter Park
- 32792
- Goldenrod
- 5346 CYPRESS DRIVE
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