The Highlands is a neighborhood in north Winter Springs, in the 32708 zip code, built mostly in the 1970s. Homes are stucco and block, predominantly single story. Most homes fall between about 900 and 1,900 square feet under air, and the median lot is about an eighth of an acre.
Homes here carry an HOA, billed annually, typically around $310. Confirm the figure on a specific parcel before relying on it.
What the homes are
Built Mostly built in the 1970s, with homes from 1972 to 2021.
Construction Stucco and block. Shingle roofs on 68% of homes.
Size Most homes fall between about 900 and 1,900 square feet under air.
Bedrooms Three bedrooms is the most common plan, then two.
Lot The median lot is about an eighth of an acre.
HOA Billed annually, typically around $310. Confirm on a specific parcel before relying on it.
Where The Highlands is
The Highlands, centered at 28.708834, -81.313176. 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 The Highlands, 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
29 min
16.0
Orlando International Airport
37 min
31.0
Winter Park
24 min
10.2
Heathrow and Lake Mary offices
25 min
9.2
Public schools nearby
Highlands Elementary School 4 min, 0.9 mi
Winter Springs Elementary School 4 min, 0.9 mi
Longwood Elementary School 6 min, 2.3 mi
Layer Elementary School 6 min, 1.9 mi
Private schools nearby
Tuanis Volleyball Academy 7 min, 1.8 mi
MAGAL Hebrew School 5 min, 1.5 mi
Reach Beyond Academy 5 min, 1.5 mi
Parks and recreation
Sunshine Park 4 min, 0.9 mi
Audubon Park 2 min, 0.5 mi
Wildwood Homes Dog Park 4 min, 1.2 mi
Soldiers Creek Park 7 min, 2.3 mi
Groceries and errands
Fancy Fruit & Produce, Grocery Store Longwood 6 min, 2.1 mi
Nearest is not the same as zoned. The schools above are the closest ones to The Highlands 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 Seminole County Public Schools before it matters to a decision.
Places and drive times from Google, checked 9 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.
This page tracks what homes in The Highlands actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 32 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 October 2026.
What homes sold for in The Highlands
$333,425Median sale price
$196Median per square foot
48 daysMedian days to contract
32Homes sold in 12 months
Sale prices ran from $121,250 to $553,700, 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
28
$303,000
$192
34 days
2,000 to 3,000 sq ft
4
$451,255
$215
107 days
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 15 sales, closed at 98.2% of asking18 days
Reduced at least once 17 sales, closed at 96.7% of the reduced price87 days
Sellers who priced correctly and held their number went under contract in a median 18 days. Sellers who had to reduce took 87 days and still closed at 96.7% of their already reduced price, after a typical cut of $25,000. Opening high costs time and money, in that order.
Seller concessions
62%Of sales included a seller credit
$6,500Typical credit when there was one
20 of 32Sales 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 19 sales58%
Cash 7 sales21%
FHA 5 sales15%
VA 2 sales6%
Cash was 21% 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 The Highlands, 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 The Highlands in Winter Springs, Seminole County, covering closed sales from 13 October 2025 through 8 October 2026, refreshed monthly and current as of October 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. One record was excluded as an off-market transfer rather than an open market sale. Data believed accurate but not guaranteed; listings and closings change daily.
