HIGHLAND RIDGE
Homes for Sale in WINTER GARDEN, FL
True comps, carrying-cost math, and listings before the portals.
Highland Ridge Winter Garden is a small deed-restricted community in Hudson with only nine homes total, so this is not a market that behaves like a large subdivision. With three active listings and 3.3 months of supply, conditions read as balanced, but the sample size is thin enough that a single listing coming on or off the market can shift the picture quickly.
There were no recorded closings in the current window, which means there is no fresh sales data to anchor pricing expectations. Anyone evaluating this community right now should treat active listings as the primary signal and lean on comparable data from nearby communities rather than assuming a stable trend line here.
HIGHLAND RIDGE right now
🟡 Balanced market. 3.6 months of supply and 0% of the inventory already under contract put buyers and sellers on roughly even footing.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 2, 2026. Confidence: Medium (3 active and pending listings, 9 closed sales in 12 months).
🟡 Off the recent peak. The trailing-12-month median ($485K) is down 6.9% from the prior 12 months ($521K).Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Medium (9 and 41 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 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 2, 2026): the median sale price is about $485K ($257 per sq ft over the trailing 12 months of closed sales), a median 138 days on market for closed sales, and 3.6 months of supply, a balanced market. The trailing-12-month median is down 7% from the prior 12 months, computed from record-level Stellar MLS closed sales (9 closings in the current window).
HIGHLAND RIDGE is a community of 79 homes in WINTER GARDEN, Orange County, built between 2022 and 2023 (median 2023), with a median living area of about 1,996 square feet. 23% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Highland Ridge Winter Garden is a compact, amenity-equipped deed-restricted community in Hudson, Pasco County, where inventory is limited enough that each listing represents a meaningful share of the total homes.
The setting & the homes.
Aerial and on-site photos of HIGHLAND RIDGE. Swipe to explore the community.
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HIGHLAND RIDGEWho HIGHLAND RIDGE is best for.
Best for
- Buyers who want deed-restricted amenities like a pool and fitness center without a large-scale community
- Buyers comfortable moving forward with limited historical sales data to reference
- Investors evaluating a low-homestead-share community for rental or resale strategy
Probably not for
- Buyers who want a wide selection of active listings to compare before deciding
- Buyers who need recent closed-sale data to validate an offer price
- Buyers seeking a larger community with more consistent turnover
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($485K) IS the median in the snapshot above, and the move from 2025 ($521K) IS the -6.9% one-year change.
Windows contain 4 to 88 sales each (9 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2023 through 2026. Deemed reliable but not guaranteed.
HIGHLAND RIDGE Market Scorecard
HIGHLAND RIDGE is currently a strong seller's market. About 1.8 months of supply, a median asking price of $573,950, and homes go under contract in about 58 days.
Go deeper: county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in HIGHLAND RIDGE, 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 August 2026 through August 2026. Deemed reliable but not guaranteed.
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 · 116 daysTop listing
Active · 1 days
Active · 81 daysActive and pending HIGHLAND RIDGE listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2023 through 2026. Tap any home to ask about it.
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
- Pool · reported on 10 of 12 listings
- Playground · reported on 9 of 12 listings
- Park · reported on 8 of 12 listings
- Recreation Facilities · reported on 7 of 12 listings
- Association Recreation - Owned · reported on 7 of 12 listings
- Deed Restrictions · reported on 3 of 12 listings
- Clubhouse · reported on 1 of 12 listings
- Fitness Center · reported on 1 of 12 listings
- Security Lights · reported on 1 of 12 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.
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.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
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 Small Footprint, Amenity-Heavy
At nine homes total, Highland Ridge Winter Garden is defined more by its amenity package than by transaction volume. The community carries a pool, playground, park, clubhouse, fitness center, and owned recreation facilities, all under deed restrictions with security lighting noted across listings. That combination signals a maintained, structured setting, though buyers should confirm current access and any associated fees directly with the HOA since MLS-reported amenities can lag on-the-ground reality.
The homestead share sits at zero percent, meaning none of the homes here currently carry a homestead exemption. That points to a community where ownership skews toward non-primary-residence use, which is worth factoring into how you think about resale timing, rental potential, or long-term holding strategy if you are buying here.
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 4 factors (4.2). Basis: Recent Direction -6.9% year-over-year; Liquidity & Demand 3.6 months of supply; Owner Commitment 23% owner-occupied; Pricing Power 91.0% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a community this small, with only three active listings and no recent closings to reference, pricing a home correctly takes more than pulling a standard comp report. We track the handful of transactions that do happen here alongside comparable Hudson communities so you are not guessing based on a stale or incomplete data set.
HIGHLAND RIDGE in 15 seconds.
HOA, CDD & Fees
- Mandatory HOA. Confirm current dues
- Any club/amenity membership is billed separately
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 homes for sale in HIGHLAND RIDGE on the map →
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?
Do cash buyers compete in HIGHLAND RIDGE?
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?
Should you buy in HIGHLAND RIDGE?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near HIGHLAND RIDGE with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2023 (142 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 your area comps.
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