Dubsdread Heights is a neighborhood in west Winter Park, in the 32789 zip code, built mostly in the 1950s. Homes are block and stucco, predominantly single story. Most homes fall between about 1,000 and 3,100 square feet under air, and the median lot is roughly a fifth of an acre.
Most of Dubsdread Heights carries no mandatory HOA.
What the homes are
Built Mostly built in the 1950s, with homes from 1925 to 2020.
Construction Block and stucco. Shingle roofs are near universal.
Style Bungalow, Ranch, Mediterranean. Predominantly single story.
Size Most homes fall between about 1,000 and 3,100 square feet under air.
Bedrooms Three bedrooms is the most common plan, then two, then four.
Lot The median lot is roughly a fifth of an acre.
HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.
Where Dubsdread Heights is
Dubsdread Heights, centered at 28.59075, -81.383854. Drag to explore.Street level, inside the neighborhood. Drag to look around.
Drive times below are measured on the road network from the center of Dubsdread Heights, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.
Driving to
Time
Miles
Downtown Orlando
11 min
4.3
Walt Disney World
26 min
24.3
Orlando International Airport
27 min
25.7
Universal Orlando
18 min
12.3
Public schools nearby
Killarney Elementary School 3 min, 0.7 mi
Park Maitland School of Winter Park 2 min, 0.8 mi
Edgewater High School 5 min, 1.8 mi
Hospital Homebound School 5 min, 1.9 mi
Private schools nearby
Bishop Moore Catholic High School 6 min, 1.9 mi
St. Charles Borromeo Catholic School 5 min, 1.6 mi
Revelation Christian Academy Orlando, Inc. 3 min, 0.9 mi
Florida Children's Academy 3 min, 0.9 mi
Parks and recreation
Mathews Park 4 min, 1.3 mi
Orwin Manor Park 4 min, 1.5 mi
Princeton Park 6 min, 2.0 mi
Interlaken Park 8 min, 3.2 mi
Groceries and errands
Publix Super Market at Hollieanna Shopping Center 4 min, 1.2 mi
Wild Fork Meat & Seafood Market, Winter Park 5 min, 1.5 mi
Nearest is not the same as zoned. The schools above are the closest ones to Dubsdread Heights by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.
Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in Dubsdread Heights actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 7 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated September 2026.
Read this one loosely. Fewer than eight homes closed here in the last year, so every median on this page rests on a small sample and can swing on a single sale.
What homes sold for in Dubsdread Heights
$397,240Median sale price
$283Median per square foot
23 daysMedian days to contract
7Homes sold in 12 months
Sale prices ran from $310,000 to $735,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.
By size
Home size
Sales
Median price
Median $/sq ft
Median days
Under 2,000 sq ft
4
$357,052
$325
22 days
Larger homes usually show a lower price per square foot. That is normal and it is why a price per foot taken from the whole neighborhood should never be applied straight to one house.
Homes priced right sold far faster
Median days to go under contract. Shorter is better.
Never reduced 3 sales, closed at 96.1% of asking18 days
Reduced at least once 4 sales, closed at 99.3% of the reduced price46 days
Sellers who priced correctly and held their number went under contract in a median 18 days. Sellers who had to reduce took 46 days and still closed at 99.3% of their already reduced price, after a typical cut of $18,000. Opening high costs time and money, in that order.
Seller concessions
43%Of sales included a seller credit
$16,760Typical credit when there was one
3 of 7Sales carrying a credit
A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.
How buyers paid
Conventional 4 sales57%
FHA 1 sales14%
VA 1 sales14%
Cash 1 sales14%
Cash was 14% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.
Questions about a specific home in Dubsdread Heights, or want to know what yours would sell for? Call or text Brenden Rendo at 407-616-9019 or send a message.
About this data. Source is the Stellar MLS feed for Dubsdread Heights in Winter Park, Orange County, covering closed sales from 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.
