Highland Woods
Homes for Sale in Bonita Springs, FL
True comps, carrying-cost math, and listings before the portals.
Photo via Florida Gulf Coast MLS
Over the 12 months ending 2026-07-29, 4 recorded sales closed at a median of $820,000, $387 per square foot, a median 34 days on market, sellers accepting 92% of original asking (-20% versus the prior year). At the median price and Lee County's FY2025-26 rate of 15.97 mills, annual property tax runs about $13,100 ($12,430 with the full homestead exemption).
Highland Woods right now
🔴 Off the recent peak. The trailing-12-month median ($820K) is down 19.6% from the prior 12 months ($1.02M). With about 4 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Florida Gulf Coast MLS closed sales, 12-month windows ending July 29. Confidence: Low (4 and 4 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated July 29, 2026 · Live data: Florida Gulf Coast MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Highland Woods market snapshot (as of July 29, 2026): the median sale price is about $820K ($387 per sq ft over the trailing 12 months of closed sales), and a median 34 days on market for closed sales. The trailing-12-month median is down 20% from the prior 12 months, computed from record-level Florida Gulf Coast MLS closed sales (4 closings in the current window).
Highland Woods is a community of 499 homes in Bonita Springs, Lee County, built between 1996 and 2001 (median 1998.0), with a median living area of about 1,556 square feet. 42% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending July 29 of each year, from record-level Florida Gulf Coast MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($820K) IS the median in the snapshot above, and the move from 2025 ($1.02M) IS the -19.6% one-year change.
Windows contain 1 to 9 sales each (4 in the current window); every figure carries its sample size, and thin markets swing on single closings. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
Highland Woods Market Scorecard
Highland Woods is currently a thin data market. Limited supply, a median asking price of $1,099,000.
Typical home value in the 34135 ZIP is $458,395, about 6.0% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · 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.
Homes For Sale Right Now in Highland Woods
Live MLS inventory for Highland Woods. 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 and pending Highland Woods listings as of 2026-09-11, priced high to low. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. Tap any home to ask about it.
The Highland Woods buying strategy.
If we were buying in Highland Woods 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 Woods.
A closer look at the Highland Woods market
At a median of $387 per square foot, Highland Woods 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 trailing-12-month median down 20% year over year. Homes that do trade take a median 34 days on market, useful leverage on any listing that has lingered.
The housing stock is 499 homes built between 1996 and 2001, and 42% 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 Woods. 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 Woods 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 (3.3). Basis: Recent Direction -19.6% year-over-year; Owner Commitment 42% owner-occupied; Pricing Power 91.7% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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 Woods 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 Woods sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Highland Woods, 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 Woods home worth?
Get a no-obligation home value based on real comparable sales in Highland Woods, 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 Bonita Springs →
Frequently Asked Questions
What is the median home price in Highland Woods?
How long do homes in Highland Woods take to sell?
How many homes are in Highland Woods?
What share of Highland Woods is owner-occupied?
When were the homes in Highland Woods built?
Do cash buyers compete in Highland Woods?
Who is the best real estate agent for Highland Woods?
How do I find a top Bonita Springs real estate agent who knows Highland Woods?
Can Momentum Realty connect me with an agent for Highland Woods?
Nearby Communities
Explore more neighborhoods near Highland Woods with Momentum Realty’s local guides.
Data sources & freshness
| Community market stats | Florida Gulf Coast MLS closed sales, 12-month windows ending July 29, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 34135)) |
| Under-contract shares | Florida Gulf Coast MLS records, as of 2026-07-18 |
| Historical depth | Closed-sale records back to 2014 (50 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 Florida Gulf Coast 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 Florida Gulf Coast 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 Woods fits the bigger picture — live prices, inventory, and Momentum Scores: