Highland Rdg Ph 2
Homes for Sale in Winter Garden, FL

Community in Winter Garden · Orange County
183 homesBuilt 2022–2024Median sale $510K
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True comps, carrying-cost math, and listings before the portals.

Built fromLive Stellar MLS data2 years of closingsFL DOR public recordsUpdated twice daily
Live · Highland Rdg Ph 2 Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Price
$510K
Median sold · 12 mo
$245/sf
Sold $/sqft · 12 mo
peak $253 in 2024
88.7%
Sale vs ask
Orange median: 96.0%
Tempo
176days
Median DOM · closed
0 days at the 2024 low
3
Sold · last 12 mo
10-yr average: about 3 a year
Ownership and context
25%
Owner-occupied · Highland Rdg Ph 2
47 of 188 parcels homesteaded (FL DOR 2025)
75%
Non-owner-occupied · Highland Rdg Ph 2
incl. 25% trust or LLC-held · 100% out-of-state
0%
Cash buyers · Highland Rdg Ph 2
0 of 3 sales, 12 mo ending June 2026
183
Homes in the community
plus 5 vacant residential lots · 188 residential parcels (FL DOR 2025)
Track record · 2 years of records
Est. 2022
Community established
homes built 2022-2024, median 2024 (FL DOR 2025)
2
Failed listings · 2026
peaked at 3 in 2025
2,082sqft
Median sold home size
12-mo windows, closed sales
1.6%/yr
Turnover rate
about 3 of 183 homes trade a year

The 60-Second Overview

Highland Rdg Ph 2 market snapshot (as of July 15, 2026): the median sale price is about $510K ($245 per sq ft over the trailing 12 months of closed sales), and a median 176 days on market for closed sales.

Highland Rdg Ph 2 is a community of 183 homes in Winter Garden, Orange County, built between 2022 and 2024 (median 2024), with a median living area of about 2,082 square feet. 25% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

If we were buying in Highland Rdg Ph 2 today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 Rdg Ph 2.

A closer look at the Highland Rdg Ph 2 market

At a median of $245 per square foot, Highland Rdg Ph 2 prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.

The housing stock is 183 homes built between 2022 and 2024, and 25% 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 Rdg Ph 2. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

HOA, CDD & Fees

In short
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Highland Rdg Ph 2 sales matched to your home.

What is your Highland Rdg Ph 2 home worth?

Get a no-obligation home value based on real comparable sales in Highland Rdg Ph 2, 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 Rdg Ph 2 on the map →

Real comps, not an automated estimate.

Frequently Asked Questions

What is the median home price in Highland Rdg Ph 2?
The median sale price in Highland Rdg Ph 2 was $510K over the 12 months ending July 15, 2026 (3 closed sales, Stellar MLS).
How long do homes in Highland Rdg Ph 2 take to sell?
Homes that closed in the 12 months ending July 15, 2026 took a median 176 days on market (3 sales, Stellar MLS).
How many homes are in Highland Rdg Ph 2?
The Florida DOR 2025 assessment roll shows 183 homes plus 5 vacant residential lots in Highland Rdg Ph 2 (public records).
What share of Highland Rdg Ph 2 is owner-occupied?
25% of Highland Rdg Ph 2 parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Highland Rdg Ph 2 built?
Homes in Highland Rdg Ph 2 were built between 2022 and 2024, with a median year built of 2024 (FL DOR 2025 roll).
Do cash buyers compete in Highland Rdg Ph 2?
Cash buyers took 0% of Highland Rdg Ph 2 sales in the 12 months ending June 2026 (0 of 3 closings, Stellar MLS).
Who is the best real estate agent for Highland Rdg Ph 2?
The best agent for Highland Rdg Ph 2 is one who actively works Winter Garden and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Highland Rdg Ph 2.
How do I find a top Winter Garden real estate agent who knows Highland Rdg Ph 2?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Highland Rdg Ph 2 and the wider Winter Garden area.
Can Momentum Realty connect me with an agent for Highland Rdg Ph 2?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Highland Rdg Ph 2 purchase or sale - no call center and no pressure.

Data sources & freshness

Community market statsStellar MLS closed sales, 12-month windows ending July 15, 2026
Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (2 streets, ZIP 34787))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2024 (8 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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