5346 CYPRESS DRIVE, Winter Park, FL 32792
OFF MARKET

$385,000

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,670 sqft

5346 CYPRESS DRIVE, Winter Park, FL 32792

Goldenrod
Est. Refi. Payment $2,758/mo*
Refinance Your Home
Currently Off Market - Sold Oct 27, 2025 for $390,000

Home Value

Trulia Estimate
$385K
Since last month
Decreased$2K (-0.4%)
Since last year
Increased$26K (+7.1%)
Since last sale
Decreased$5K (-1.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +83% in the last 10 years
MonthEstimated value
2026
August 2026$385K
August 2026$385K
July 2026$387K
June 2026$383K
May 2026$385K
April 2026$386K
March 2026$389K
February 2026$388K
January 2026$389K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5330 TANGERINE AVENUE, Winter Park, FL
0.08
Single-Family Home
$354,900
05/15/26
3
2
1,642
5201 ARDMORE DRIVE, Winter Park, FL
0.18
Single-Family Home
$425,000
01/06/26
3
2
1,640
5357 ORANGE AVENUE, Winter Park, FL
0.14
Single-Family Home
$400,000
02/03/26
3
2
1,356
5236 TANGERINE AVENUE, Winter Park, FL
0.13
Single-Family Home
$350,000
04/06/26
3
2
1,404
7120 BROOKSIDE TRAIL, Winter Park, FL
0.09
Single-Family Home
$470,000
06/16/26
4
2
1,753
5338 TANGERINE AVENUE, Winter Park, FL
0.09
Single-Family Home
$425,000
01/08/26
4
2
2,195
5350 ORANGE AVENUE, Winter Park, FL
0.11
Single-Family Home
$453,040
07/25/26
4
2
1,863
5418 ARDMORE DRIVE, Winter Park, FL
0.24
Single-Family Home
$435,800
04/27/26
3
2
1,560
7213 SILVER PLACE, Winter Park, FL
0.20
Single-Family Home
$360,000
03/27/26
3
2
1,252

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5334 CYPRESS DRIVE, Winter Park, FL 32792
0.03
$412,600
4
2
1,734
Off Market
5339 CYPRESS DRIVE, Winter Park, FL 32792
0.04
$362,500
4
2
1,782
Off Market
5318 POINSETTA AVENUE, Winter Park, FL 32792
0.05
$410,200
3
2
1,467
Off Market
5331 OAK COURT, Winter Park, FL 32792
0.04
$460,000
3
2
1,263
For Sale
5324 POINSETTA AVENUE, Winter Park, FL 32792
0.05
$469,700
5
3
2,250
Off Market
5330 TANGERINE AVENUE, Winter Park, FL 32792
0.08
$354,900
3
2
1,642
Recently Sold
5231 ARDMORE DRIVE, Winter Park, FL 32792
0.12
$391,200
3
2
1,645
Off Market
5338 TANGERINE AVENUE, Winter Park, FL 32792
0.09
$425,000
4
2
2,195
Recently Sold
5236 TANGERINE AVENUE, Winter Park, FL 32792
0.13
$350,000
3
2
1,404
Recently Sold
7134 WRENWOOD WAY, Winter Park, FL 32792
0.14
$437,500
4
2
1,712
Recently Sold
7104 WRENWOOD WAY, Winter Park, FL 32792
0.15
$465,000
4
2
1,778
Recently Sold

Local Information

  • Map ViewExplore the area around 5346 CYPRESS DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1976
1,670 sqft
$231/sqft
2 Car Garage

About this House

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.
5346 CYPRESS DRIVE, Winter Park, FL 32792 is a 3 bedroom, 2 bathroom, 1,670 sqft single-family home in Goldenrod, built in 1976. It last sold for $390,000 on Oct 27, 2025 (5% below the $410,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $385,000, with a rent estimate of $2,950/month.
Last check for updates: about 5 hours ago
Listed by Kristy Kesterson, (407) 535-8789
KELLER WILLIAMS ADVANTAGE REALTY, (407) 977-7600
Bought with: Jennifer Rigsby, (407) 463-9709, WEMERT GROUP REALTY LLC, (407) 743-8356
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6333715
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 5346 CYPRESS DRIVE

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Primary Bedroom, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1670 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Water ConnectedAppliances: Dishwasher, Microwave, Range, RefrigeratorDishwasherLaundry: In GarageMicrowaveRefrigerator
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Living Room, Wood BurningHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window TreatmentsFlooring: Carpet, Ceramic Tile, Laminate
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Ceramic Tile, Laminate
View
No View

Exterior Features

Exterior Home Features
Roof: ShingleExterior: Lighting, Private Mailbox, Rain GuttersFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Frontage
Road Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 31

Property Information

Year Built
Year Built: 1976
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 3421305DG00002060

Price & Status

Price
List Price: $410,000
Status Change & Dates
Off Market Date: Sat Oct 04 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: WINTER PARKCommunity: WRENWOOD HEIGHTS UNIT 2
School Information
Elementary School: Eastbrook ElementaryJr High / Middle School: Tuskawilla MiddleHigh School: Lake Howell High

Building

Building Area
Building Area: 2274 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 9408 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6333715Showing Requirements: ShowingTimeUniversal Property Id: US-12117-N-342130500002060-R-N

Price and Tax history

DateEventPrice
Oct 27, 2025
Source: Stellar MLS #O6333715
Sold
$390,000
Oct 5, 2025
Source: Stellar MLS #O6333715
Pending
$410,000
Sep 22, 2025
Source: Stellar MLS #O6333715
PriceChange
$410,000
Price decreased by 2%
Sep 3, 2025
Source: Stellar MLS #O6333715
Listed For Sale
$419,900

Market trends in Winter Park

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$451K
$833MoM
Sale-to-List Price
98.0%
0.3%MoM
Price per sq ft
$287
$0MoM
Available listings
368
12MoM

Around this home

Neighborhood Overview

Goldenrod
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Goldenrod

At least 90 Trulia users voted on each feature.

  • 88 % Say car is needed

  • 86 % Say there are sidewalks

  • 85 % Say it's dog friendly

  • 81 % Say parking is easy

  • 71 % Say there's holiday spirit

  • 69 % Say yards are well-kept

  • 59 % Say people would walk alone at night

  • 58 % Say it's quiet

  • 55 % Say kids play outside

  • 53 % Say it's walkable to grocery stores

  • 53 % Say streets are well-lit

  • 52 % Say it's walkable to restaurants

  • 45 % Say neighbors are friendly

  • 33 % Say they plan to stay for at least 5 years

  • 31 % Say there's wildlife

  • 23 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
    0
    Flag
  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
    0
    Flag
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
    Flag
  • Lvia M.
    "The neighborhood is very nice, but you had to be careful, have to read the contract before you pay your deposit."
    14
    Flag
  • Michael F.
    "I’ve lived here for 4 years, almost. It’s a quiet neighborhood despite the annoying fireworks. But people are nice. "
    57
    Flag
  • Rosie A.
    "this area is conveniently close to major highways and toll roads. traffic on Aloma can be hectic but if you know not to be in certain areas during heavy traffic times, not bad at all! "
    2
    Flag
  • Emily D.
    "Rush hour is very real here, very congested roads since they are main commuter streets for Orlando. "
    2
    Flag
  • Samanthhh
    "Some people in the east brook neighborhood let their dogs run free in the front yard, and that’s not good for me and my dog, because my dog doesn’t react well to to that. 2/5 times this has happened to me, the owners did nothing to help break up the dog fight that was happening while I still had my dog on his leash. This one older Hispanic lady yelled at me because she claimed her dog had every right to run up to us because the sidewalk belonged to her. Even after I ended up in the street trying to drag my dog out of the fight. Unreal. "
    0
    Flag
  • Jasmine O.
    "People are helpful and friendly. Many elderly live here and so have seen the neighborhood change and have great stories to tell."
    1
    Flag
  • Grifcan
    "This is a great and inexpensive area located in the Winter Park zip code. I've lived in this area my whole life and have raised my son here. "
    0
    Flag
  • Maliagrille
    "I work in the theme park industry so mine isn’t really a fair estimate but traffic in the area is reasonable. There are two access points to toll roads and I4 is a straight shot down the main road. "
    0
    Flag
  • Alycia B.
    "Centrally located. The is a Walmart and Publix in any direction and the highways are close by so it’s easy to travel anywhere in Orlando. "
    1
    Flag
  • Alycia B.
    "Central to everything. Full sail brings a lot of students to the area and new developments keep popping up. Soon the luckys and wawa will be open!"
    0
    Flag
  • John l.
    "the way they live, the way they do. their behavior. the way they drive in the neighborhood. the way they looks and speaks with other people............. "
    0
    Flag
  • Kayleen o.
    "It will be nice to find a place we’re everything is closed. And it is also closed to my job and my kids babysitter. "
    2
    Flag
  • Slpottorf169
    "I feel safe and comfortable in this neighborhood. In neighboring blocks I do see school aged children, but not many in my immediate area. Close to recreation and shopping areas, but still has a small town feel. "
    1
    Flag
  • Paul M.
    "It is quiet,safe and most of all clean and friendly. The voting precinct is 1 mile or less away. With in 2 miles, Publix, Family Dollar Grocery and much much more! Several major up grades have been done in the past 5 years."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5346 CYPRESS DRIVE

  • What is 5346 CYPRESS DRIVE estimated to be worth?
    Trulia's estimated value for 5346 CYPRESS DRIVE in Winter Park, FL is $385,000.
  • What is the price history for 5346 CYPRESS DRIVE?
    5346 CYPRESS DRIVE in Winter Park, FL last sold for $390,000 in October 2025.
  • Is Winter Park a buyer's or seller's market?
    Winter Park is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Park?
    The median sale price in Winter Park is $451K. That is down $833 from the prior month.
  • Does 5346 CYPRESS DRIVE have air conditioning?
    Yes, 5346 CYPRESS DRIVE in Winter Park, FL has air conditioning.
  • Does 5346 CYPRESS DRIVE have laundry facilities?
    Yes, 5346 CYPRESS DRIVE in Winter Park, FL has laundry facilities.

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