Maitland Shores is a neighborhood in north Winter Park, in the 32789 zip code, built mostly in the 2000s. Homes are block and stucco. Most homes fall between about 2,000 and 5,200 square feet under air, the median lot is roughly a third of an acre, and a two car garage is standard.
Maitland Shores has an optional homeowners association rather than a mandatory one, so there is no deed restricted membership to inherit. Dues run about $75 annually for those who join. Confirm the position on a specific parcel before relying on it.
John Langdon Park sits inside the subdivision.
What the homes are
Built Mostly built in the 2000s, with homes from 1925 to 2025.
Construction Block and stucco. Shingle roofs are near universal.
Style Traditional, Mediterranean. Predominantly two story.
Size Most homes fall between about 2,000 and 5,200 square feet under air.
Bedrooms Four bedrooms is the most common plan, then five, then three.
Garage A two car garage is standard.
Lot The median lot is roughly a third of an acre.
HOA Optional rather than mandatory, so there is no deed restricted membership. Dues run about $75 annually for those who join. Confirm on a specific parcel before relying on it.
Where Maitland Shores is
Maitland Shores, centered at 28.622901, -81.341831. 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 Maitland Shores, 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
22 min
11.7
Walt Disney World
37 min
30.8
Orlando International Airport
32 min
24.8
Universal Orlando
29 min
18.9
Public schools nearby
Dommerich Elementary School 5 min, 1.4 mi
Lakemont Elementary School 7 min, 2.1 mi
English Estates Elementary School 8 min, 2.4 mi
Lake Sybelia Elementary School 8 min, 2.7 mi
Private schools nearby
Maitland Montessori School 4 min, 1.7 mi
Center Academy Maitland 5 min, 2.0 mi
Christian Education at Woodruff Academy 8 min, 2.2 mi
Parks and recreation
John Langdon Park 1 min, 0.1 mi
Howell Branch Preserve 4 min, 1.0 mi
John Hudson Park 3 min, 0.8 mi
Kings Row Park 2 min, 0.6 mi
Groceries and errands
DG Market 3 min, 1.2 mi
Publix Super Market at Maitland Place 4 min, 1.7 mi
Publix Super Market at Casselberry Commons 5 min, 1.6 mi
The Ancient Olive Gourmet of Winter Park 12 min, 2.8 mi
Nearest is not the same as zoned. The schools above are the closest ones to Maitland Shores 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 Maitland Shores actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 4 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 Maitland Shores
$1,834,500Median sale price
$472Median per square foot
112 daysMedian days to contract
4Homes sold in 12 months
Sale prices ran from $952,000 to $2,200,000, 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
3,000 sq ft and up
3
$2,024,000
$508
63 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 1 sales, closed at 97.1% of asking7 days
Reduced at least once 3 sales, closed at 94.2% of the reduced price160 days
Sellers who priced correctly and held their number went under contract in a median 7 days. Sellers who had to reduce took 160 days and still closed at 94.2% of their already reduced price, after a typical cut of $195,000. Opening high costs time and money, in that order.
Seller concessions
50%Of sales included a seller credit
$3,000Typical credit when there was one
2 of 4Sales 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 2 sales50%
Conventional 2 sales50%
Cash was 50% 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 Maitland Shores, 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 Maitland Shores 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.
