Highland Ridge is a 2020s neighborhood in south Winter Garden, in the 34787 zip code. Homes are block and stucco. Most homes fall between about 1,800 and 2,100 square feet under air, the median lot is about 0.10 acres, and a two car garage is standard.
Homes here carry an HOA, billed monthly, typically around $100. Confirm the figure on a specific parcel before relying on it.
Target Grocery sits inside the subdivision.
What the homes are
Built Essentially all built in the 2020s.
Construction Block and stucco. Shingle roofs are near universal.
Style Bungalow. Predominantly two story.
Size Most homes fall between about 1,800 and 2,100 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 about 0.10 acres.
HOA Billed monthly, typically around $100. Confirm on a specific parcel before relying on it.
Where Highland Ridge is
Highland Ridge, centered at 28.365018, -81.617276. 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 Highland Ridge, 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
35 min
28.8
Walt Disney World
13 min
6.5
Orlando International Airport
38 min
25.6
Universal Orlando
34 min
18.3
Public schools nearby
Water Spring Elementary School 13 min, 5.7 mi
Parks and recreation
Winding Bay Preserve 10 min, 4.6 mi
Groceries and errands
Target Grocery 6 min, 1.4 mi
Publix Super Market at Orange Lake Town Center 11 min, 4.0 mi
Nearest is not the same as zoned. The schools above are the closest ones to Highland Ridge 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 Highland Ridge actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 10 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.
What homes sold for in Highland Ridge
$478,766Median sale price
$258Median per square foot
138 daysMedian days to contract
10Homes sold in 12 months
Sale prices ran from $424,000 to $574,000, 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
6
$471,650
$264
124 days
2,000 to 3,000 sq ft
4
$496,116
$240
147 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 96.2% of asking83 days
Reduced at least once 9 sales, closed at 98.1% of the reduced price138 days
Sellers who priced correctly and held their number went under contract in a median 83 days. Sellers who had to reduce took 138 days and still closed at 98.1% of their already reduced price, after a typical cut of $46,000. Opening high costs time and money, in that order.
Seller concessions
70%Of sales included a seller credit
$5,000Typical credit when there was one
7 of 10Sales 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 8 sales80%
FHA 1 sales10%
Cash 1 sales10%
Cash was 10% 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 Highland Ridge, 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 Highland Ridge in Winter Garden, 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.
