Winter Park Pines is a 1960s neighborhood in east Winter Park, in the 32792 zip code. Homes are block and stucco, predominantly single story. Most homes fall between about 1,500 and 2,300 square feet under air, the median lot is roughly a fifth of an acre, and a two car garage is standard.
Winter Park Pines has an optional homeowners association rather than a mandatory one, so there is no deed restricted membership to inherit. Dues run about $50 annually for those who join. Confirm the position on a specific parcel before relying on it.
What the homes are
Built Mostly built in the 1960s, with homes from 1962 to 2023.
Construction Block and stucco. Shingle roofs are near universal.
Style Ranch, Traditional. Predominantly single story.
Size Most homes fall between about 1,500 and 2,300 square feet under air.
Bedrooms Four bedrooms is the most common plan, then three.
Garage A two car garage is standard.
Lot The median lot is roughly a fifth of an acre.
HOA Optional rather than mandatory, so there is no deed restricted membership. Dues run about $50 annually for those who join. Confirm on a specific parcel before relying on it.
Where Winter Park Pines is
Winter Park Pines, centered at 28.58982, -81.313156. 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 Winter Park Pines, 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
17 min
8.3
Walt Disney World
34 min
28.2
Orlando International Airport
26 min
11.5
Universal Orlando
26 min
16.2
Public schools nearby
Brookshire Elementary School 3 min, 0.7 mi
Aloma Elementary 3 min, 0.9 mi
Winter Park High School 4 min, 1.2 mi
Winter Park High School, South Gate (Baldwin Park) 6 min, 2.3 mi
Nearest is not the same as zoned. The schools above are the closest ones to Winter Park Pines 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 Winter Park Pines actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 39 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 November 2026.
What homes sold for in Winter Park Pines
$545,000Median sale price
$316Median per square foot
17 daysMedian days to contract
39Homes sold in 12 months
Sale prices ran from $330,000 to $794,000, 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
31
$525,000
$310
18 days
2,000 to 3,000 sq ft
8
$742,500
$320
5 days
A price per foot taken from the whole neighborhood should never be applied straight to one house.
What a pool is worth here
Homes with a private pool sold at a median $307 per square foot against $316 without one, so pool homes sold for $9 less per square foot. That comes from 12 sales with a pool and 27 without.
Homes priced right sold far faster
Median days to go under contract. Shorter is better.
Never reduced 26 sales, closed at 100% of asking5 days
Reduced at least once 13 sales, closed at 96.8% of the reduced price63 days
Sellers who priced correctly and held their number went under contract in a median 5 days. Sellers who had to reduce took 63 days and still closed at 96.8% of their already reduced price, after a typical cut of $21,000. Opening high costs time and money, in that order.
Seller concessions
21%Of sales included a seller credit
$5,000Typical credit when there was one
8 of 39Sales 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
Cash 18 sales46%
Conventional 16 sales41%
VA 4 sales10%
FHA 1 sale3%
Cash was 46% 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.
Renovation activity
Homes bought and then resold after renovation, over the last thirty months.
10Homes bought and resold renovated
$211,500Typical gap between the two prices
5 monthsTypical time held
$360Median resale per square foot
39 daysMedian days to resell
That gap is not profit. It is the difference between two sale prices and it does not subtract the cost of the work, the months of carrying cost, or the cost of selling. Treat it as the size of the opportunity these buyers saw, not the money they made.
For an owner the useful read is simpler. Buyers here paid a clear premium for finished condition, and that premium is large enough that professional buyers compete for the dated inventory. If your home needs work you have a real audience either way, and the choice is whether you capture that premium or sell it to someone who will.
Questions about a specific home in Winter Park Pines, 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 Winter Park Pines in Winter Park, Orange County, covering closed sales from 8 November 2025 through 3 November 2026, refreshed monthly and current as of November 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.
