Highland Rdg Ph 2
Homes for Sale in Winter Garden, FL
True comps, carrying-cost math, and listings before the portals.
Highland Rdg Ph 2 is a young, tightly built section of Winter Garden, with every home dated between 2022 and 2024 and a median year built of 2024. That narrow construction window means condition variance is low compared to older neighborhoods — the spread in price here is driven more by floor plan, lot, and finish level than by age or deferred maintenance.
The 176-day median days-on-market is the number that matters most right now. That is a long hold for a newer-construction community, and it tells you pricing has not been moving quickly at the $510,000 median. Sellers here need to price to the $244.96-per-square-foot level from the start rather than testing the top of the range, and buyers have room to negotiate on terms, timeline, or concessions rather than racing to compete.
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).
Highland Rdg Ph 2 is a compact, recently built pocket of Winter Garden — 183 homes, all constructed within a three-year span, with a median size just over 2,000 square feet. It reads as a newer-construction micro-market rather than an established, amenity-anchored community.
Who Highland Rdg Ph 2 is best for.
Best for
- Buyers targeting recently built construction (2022–2024) over older resale stock
- Buyers comfortable negotiating on price or terms in a market with longer days-on-market
- Buyers focused on Winter Garden location who do not require an amenity package as part of the purchase
Probably not for
- Buyers who need an active, amenity-rich HOA community as a primary decision factor
- Buyers expecting a fast-moving, multiple-offer resale environment
- Investors expecting an established rental or resale track record — the community is still early in its cycle
The Highland Rdg Ph 2 buying strategy.
If we were buying in Highland Rdg Ph 2 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 Rdg Ph 2.
New construction, slow clock
At a median $510,000 and $244.96 per square foot, Highland Rdg Ph 2 prices in line with what you'd expect from 2022–2024 construction in this part of Orange County. The median living area of 2,082 square feet suggests a mid-size single-family footprint — not the smallest new-build product on the market, but not oversized either.
The 25% homestead share is worth noting: it means a minority of the 183 homes currently carry a homestead exemption, which typically points to a meaningful share of non-primary-residence ownership — investment holds or second homes mixed in with owner-occupied properties. Combined with a median 176-day market time, this reads as a community still working through its early resale and rental cycle rather than one with an established, fast-turnover resale rhythm. No community amenities are currently identified from MLS listings, so buyers should verify what, if anything, is included through the HOA rather than assuming clubhouse or recreational infrastructure.
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.
Why work with Momentum here
A 176-day median days-on-market means pricing strategy and negotiation leverage matter more here than in a fast-moving resale market. We track what's actually closing versus sitting in Highland Rdg Ph 2 so sellers price to move and buyers know where there's real room to negotiate — on price, closing costs, or timeline — rather than guessing.
Highland Rdg Ph 2 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 Rdg Ph 2 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 Rdg Ph 2 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Rdg Ph 2, 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 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.
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Frequently Asked Questions
What is the median home price in Highland Rdg Ph 2?
How long do homes in Highland Rdg Ph 2 take to sell?
How many homes are in Highland Rdg Ph 2?
What share of Highland Rdg Ph 2 is owner-occupied?
When were the homes in Highland Rdg Ph 2 built?
Do cash buyers compete in Highland Rdg Ph 2?
Who is the best real estate agent for Highland Rdg Ph 2?
How do I find a top Winter Garden real estate agent who knows Highland Rdg Ph 2?
Can Momentum Realty connect me with an agent for Highland Rdg Ph 2?
Should you buy in Highland Rdg Ph 2?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 15, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (2 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-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.
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