Highland Ridge
Homes for Sale in Winter Garden, FL
All 720 homes for sale in WINTER GARDEN, FL · median $575,000 · 509 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Highland Rdg Ph 2 in Winter Garden, FL has 4 homes for sale and 2 pending, asking from $499,000 to $550,000 (median $522,995). Over the 12 months ending 2026-08-23, 4 recorded sales closed at a median of $497,500, $254 per square foot, a median 157 days on market, sellers accepting 90% of original asking. Homes listed or recently sold were built 2023 - 2024; 10 of 10 report an HOA (median $106/mo); none of the 10 geocoded homes sit in a FEMA special flood hazard zone (median elevation 116 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,300 ($7,620 with the full homestead exemption).
Homes For Sale Right Now in Highland Ridge
Live MLS inventory for Highland Ridge. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 13 daysTop listing
Active · 34 days
Active · 82 days
Active · 129 days
Pending · 107 days
Pending · 132 daysActive and pending Highland Ridge listings as of 2026-09-14, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2024 through 2026. Tap any home to ask about it.
Highland Ridge right now
🟢 Buyer-leaning market. 18.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of August 23, 2026. Confidence: Medium (6 active and pending listings, 4 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 15, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Highland Ridge market snapshot (as of August 23, 2026): the median sale price is about $498K ($254 per sq ft over the trailing 12 months of closed sales), a median 157 days on market for closed sales, and 18.0 months of supply, a buyer-leaning market.
In ZIP 34787 (WINTER GARDEN), 2,162 homes closed in the last 12 months at a median of $595K ($251/sq ft), down 0.6% year over year, with a median 36 days on market. Right now 357 active and 169 pending listings put supply at about 3.8 months - a balanced market. See the live ZIP 34787 housing market and the Orange County market.
Flood zones in HIGHLAND Ridge: of 10 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Winter Garden.
Highland Ridge is a community of 235 homes in Winter Garden, Orange County, built between 2022 and 2024 (median 2024), with a median living area of about 2,082 square feet. 24% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Highland Ridge. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Highland Ridge
Highland RidgePhotos from Stellar MLS listings in Highland Ridge; content deemed reliable but not guaranteed.
Housing distress & ownership in HIGHLAND RDG PH 2, WINTER GARDEN
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Highland Ridge on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Highland Ridge
- Playground · reported on 5 of 6 listings
- Pool · reported on 5 of 6 listings
- Park · reported on 4 of 6 listings
- Community Mailbox · reported on 4 of 6 listings
- Deed Restrictions · reported on 2 of 6 listings
- Laundry · reported on 1 of 6 listings
- Association Recreation - Owned · reported on 1 of 6 listings
- Security · reported on 1 of 6 listings
- Basketball Court · reported on 1 of 6 listings
- Clubhouse · reported on 1 of 6 listings
- Racquetball · reported on 1 of 6 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Water Spring Elementary · Elementary
- Water Spring Middle · Middle
- Horizon High School · High
Zoned schools reflect the assignments reported on recent Highland Ridge listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Highland Ridge address.
Shop the zone: Homes zoned for Horizon High School
The Highland Ridge buying strategy.
If we were buying in Highland Ridge today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Highland Ridge.
A closer look at the Highland Ridge market
At a median of $254 per square foot, Highland Ridge prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 18.0 months of supply, a buyer-leaning market. Homes that do trade take a median 157 days on market, useful leverage on any listing that has lingered.
The housing stock is 235 homes built between 2022 and 2024, and 24% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Highland Ridge. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Highland Ridge buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (1.8). Basis: Liquidity & Demand 18.0 months of supply; Owner Commitment 24% owner-occupied; Pricing Power 89.7% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $108/month (about $1,296/yr) · median of 24 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $108 per month ($1,296 a year) - the median AssociationFee across 24 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Highland Ridge buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Highland Ridge sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Ridge, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Highland Ridge home worth?
Get a no-obligation home value based on real comparable sales in Highland Ridge, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Winter Garden →
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
HIGHLAND RDG Market Scorecard
HIGHLAND RDG is currently a strong buyer's market. About 12.0 months of supply, a median asking price of $524,450, and homes go under contract in about 60 days.
Typical home value in the 34787 ZIP is $574,696, right around the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Frequently Asked Questions
What is the median home price in Highland Ridge?
How long do homes in Highland Ridge take to sell?
Is Highland Ridge a buyer's or seller's market right now?
How many homes are in Highland Ridge?
What share of Highland Ridge is owner-occupied?
When were the homes in Highland Ridge built?
Who is the best real estate agent for Highland Ridge?
How do I find a top Winter Garden real estate agent who knows Highland Ridge?
Can Momentum Realty connect me with an agent for Highland Ridge?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 23, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (3 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-18 |
| Historical depth | Closed-sale records back to 2024 (9 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how HIGHLAND RDG PH 2 fits the bigger picture — live prices, inventory, and Momentum Scores:
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