5339 CYPRESS DRIVE, Winter Park, FL 32792
OFF MARKET

$362,500

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 1,782 sqft

5339 CYPRESS DRIVE, Winter Park, FL 32792

Goldenrod
Est. Refi. Payment $2,645/mo*
Refinance Your Home
Currently Off Market - Sold Apr 2, 2025 for $372,000

Home Value

Trulia Estimate
$363K
Since last month
Increased$5K (+1.3%)
Since last year
Increased$1K (+0.4%)
Since last sale
Decreased$6K (-1.5%)
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 +77% in the last 10 years
MonthEstimated value
2026
September 2026$367K
August 2026$362K
July 2026$364K
June 2026$360K
May 2026$363K
April 2026$364K
March 2026$369K
February 2026$367K
January 2026$367K
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
5346 CYPRESS DRIVE, Winter Park, FL
0.04
Single-Family Home
$390,000
10/27/25
3
2
1,670
5350 ORANGE AVENUE, Winter Park, FL
0.09
Single-Family Home
$453,040
07/25/26
4
2
1,863
7120 BROOKSIDE TRAIL, Winter Park, FL
0.12
Single-Family Home
$470,000
06/16/26
4
2
1,753
5338 TANGERINE AVENUE, Winter Park, FL
0.12
Single-Family Home
$425,000
01/08/26
4
2
2,195
5330 TANGERINE AVENUE, Winter Park, FL
0.11
Single-Family Home
$354,900
05/15/26
3
2
1,642
7134 WRENWOOD WAY, Winter Park, FL
0.12
Single-Family Home
$437,500
07/07/26
4
2
1,712
7104 WRENWOOD WAY, Winter Park, FL
0.14
Single-Family Home
$465,000
11/25/25
4
2
1,778
5236 TANGERINE AVENUE, Winter Park, FL
0.14
Single-Family Home
$350,000
04/06/26
3
2
1,404
5201 ARDMORE DRIVE, Winter Park, FL
0.18
Single-Family Home
$425,000
01/06/26
3
2
1,640
3009 NICHOLSON DRIVE, Winter Park, FL
0.27
Single-Family Home
$445,000
07/30/26
4
2
1,645

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
5318 POINSETTA AVENUE, Winter Park, FL 32792
0.02
$411,300
3
2
1,467
Off Market
5324 POINSETTA AVENUE, Winter Park, FL 32792
0.03
$467,300
5
3
2,250
Off Market
5334 CYPRESS DRIVE, Winter Park, FL 32792
0.03
$412,600
4
2
1,734
Off Market
5346 CYPRESS DRIVE, Winter Park, FL 32792
0.04
$385,000
3
2
1,670
Off Market
5350 ORANGE AVENUE, Winter Park, FL 32792
0.09
$453,040
4
2
1,863
Recently Sold
5357 ORANGE AVENUE, Winter Park, FL 32792
0.12
$400,000
3
2
1,356
Recently Sold
7134 WRENWOOD WAY, Winter Park, FL 32792
0.12
$437,500
4
2
1,712
Recently Sold
5331 OAK COURT, Winter Park, FL 32792
0.08
$460,000
3
2
1,263
For Sale
5210 POINSETTA AVENUE, Winter Park, FL 32792
0.15
$402,500
3
2
1,476
Off Market
7120 BROOKSIDE TRAIL, Winter Park, FL 32792
0.12
$470,000
4
2
1,753
Recently Sold
5330 TANGERINE AVENUE, Winter Park, FL 32792
0.11
$354,900
3
2
1,642
Recently Sold

Local Information

  • Map ViewExplore the area around 5339 CYPRESS DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1975
1,782 sqft
$203/sqft
2 Car Garage

About this House

Great Opportunity in Prime Winter Park Location. Single-story, 4-bedroom, 2-bath home with a split floor plan, featuring separate living, dining, and family rooms. Original owner, with most features still in original condition—ideal for a renovation project. Loads of potential for investors or buyers looking to customize their dream home. Great location with easy access to top-rated Seminole County schools, shopping, dining, UCF, and major highways. Large yard offers ample space for outdoor activities or a future pool. Perfect for FHA 203k renovation mortgage
5339 CYPRESS DRIVE, Winter Park, FL 32792 is a 4 bedroom, 2 bathroom, 1,782 sqft single-family home in Goldenrod, built in 1975. It last sold for the $372,000 asking price on Apr 2, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $362,500, with a rent estimate of $2,886/month.
Last check for updates: about 3 hours ago
Listed by Fredric Crawford, (407) 619-6325
FUTURE HOME REALTY INC, (800) 921-1330
Bought with: Fredric Crawford, (407) 619-6325, FUTURE HOME REALTY INC, (800) 921-1330
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6284337
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 5339 CYPRESS DRIVE

Interior Features

Interior Details
Number of Rooms: 5Types of Rooms: Primary Bedroom, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1782 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Public, Sewer Connected, Water ConnectedAppliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Refrigerator, WasherDishwasherDisposalDryerLaundry: In GarageRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Skylight(s), Window TreatmentsFlooring: Carpet, Linoleum
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Linoleum
View
No View

Exterior Features

Exterior Home Features
Roof: ShingleExterior: Private Mailbox, SidewalkFoundation: 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: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 19

Property Information

Year Built
Year Built: 1975
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: BlockNot a New ConstructionNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Parcel Number: 3421305DG00001990

Price & Status

Price
List Price: $372,000
Status Change & Dates
Off Market Date: Mon Mar 17 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER PARKCommunity: WRENWOOD HEIGHTS UNIT 2

Building

Building Area
Building Area: 2509 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 8889 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6284337Showing Requirements: Appointment Only, ShowingTimeUniversal Property Id: US-12117-N-342130500001990-R-N

Price and Tax history

DateEventPrice
Apr 2, 2025
Source: Stellar MLS #O6284337
Sold
$372,000
Mar 17, 2025
Source: Stellar MLS #O6284337
Pending
$372,000
Feb 26, 2025
Source: Stellar MLS #O6284337
Listed For Sale
$372,000

Market trends in Winter Park

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$455K
$4.03KMoM
Sale-to-List Price
98.1%
0.1%MoM
Price per sq ft
$281
$6MoM
Available listings
382
13MoM

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 5339 CYPRESS DRIVE

  • What is 5339 CYPRESS DRIVE estimated to be worth?
    Trulia's estimated value for 5339 CYPRESS DRIVE in Winter Park, FL is $362,500.
  • What is the price history for 5339 CYPRESS DRIVE?
    5339 CYPRESS DRIVE in Winter Park, FL last sold for $372,000 in April 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 $455K. That is up $4.03K from the prior month.
  • Does 5339 CYPRESS DRIVE have air conditioning?
    Yes, 5339 CYPRESS DRIVE in Winter Park, FL has air conditioning.
  • Does 5339 CYPRESS DRIVE have laundry facilities?
    Yes, 5339 CYPRESS DRIVE in Winter Park, FL has in-unit laundry.

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