Highland Woods
Homes for Sale in Dunedin, FL
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-12, 4 recorded sales closed at a median of $854,500, $251 per square foot, a median 11 days on market, sellers accepting 97% of original asking (+0% versus the prior year). Homes listed or recently sold were built 2002 - 2003; 5 of 5 report an HOA (median $99/mo); none of the 5 geocoded homes sit in a FEMA special flood hazard zone (median elevation 62 ft). At the median price and Pinellas County's FY2025-26 rate of 19.39 mills, annual property tax runs about $16,570 ($15,750 with the full homestead exemption).
Highland Woods right now
🟡 Still climbing. The trailing-12-month median ($854K) is up 0.3% from the prior 12 months ($852K). With about 3 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 Stellar MLS closed sales, 12-month windows ending September 12. Confidence: Low (4 and 8 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 14, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside Highland Woods right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Highland Woods market snapshot (as of September 12, 2026): the median sale price is about $854K ($251 per sq ft over the trailing 12 months of closed sales), and a median 12 days on market for closed sales. The trailing-12-month median is up 0% from the prior 12 months, computed from record-level Stellar MLS closed sales (4 closings in the current window).
In ZIP 34698 (DUNEDIN), 692 homes closed in the last 12 months at a median of $380K ($292/sq ft), up 1.4% year over year, with a median 56 days on market. Right now 123 active and 32 pending listings put supply at about 5.7 months - a buyer's market. See the live ZIP 34698 housing market and the Pinellas County market.
Stellar MLS sales records identify 129 homes in Highland Woods that have changed hands since 2004, built between 2001 and 2007 (median 2003), with a median living area of about 3,379 sq ft and a typical 4-bedroom, 3.5-bath layout; 99% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
The setting & the homes.
Aerial and on-site photos of Highland Woods. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Highland Woods
Highland Woods
Highland Woods
Highland Woods
Highland WoodsPhotos from Stellar MLS listings in Highland Woods; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($854K) IS the median in the snapshot above, and the move from 2025 ($852K) IS the +0.3% one-year change.
Windows contain 0 to 9 sales each (4 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 2006 through 2026. Deemed reliable but not guaranteed.
Highland Woods Market Scorecard
Highland Woods is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 34698 ZIP is $415,777, about 23.9% above 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.
Housing distress & ownership in Highland Woods Dunedin, DUNEDIN
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 Woods 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 Woods
- Deed Restrictions · reported on 3 of 3 listings
- Gated Community - No Guard · reported on 3 of 3 listings
- Irrigation-Reclaimed Water · reported on 3 of 3 listings
- Gated · reported on 2 of 3 listings
- Fence Restrictions · reported on 1 of 3 listings
- No Truck/RV/Motorcycle Parking · reported on 1 of 3 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
- Pinellas County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Garrison-Jones Elementary (verify by address)FLDOE grade A · Public
- Dunedin Highland Middle (verify by address)FLDOE grade A · Public
- Dunedin High (verify by address)FLDOE grade A · Public
Grades are official Florida Department of Education school grades for 2025-26. Assignments are reported as of the 2025-26 year and can change; always confirm with Pinellas County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Highland Woods address.
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 $251 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 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.
HOA, CDD & Fees
- HOA dues reported around $99/month (about $1,188/yr) · median of 10 MLS listings, most billed twice a year
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $99 per month ($1,188 a year) - the median AssociationFee across 10 MLS records, normalised to a monthly figure; most are billed twice a year. 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 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 Dunedin →
Frequently Asked Questions
What is the median home price in Highland Woods?
How long do homes in Highland Woods take to sell?
What schools serve Highland Woods?
Who is the best real estate agent for Highland Woods?
How do I find a top Dunedin real estate agent who knows Highland Woods?
Can Momentum Realty connect me with an agent for Highland Woods?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 13, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Schools | 2025-26 district assignments + FLDOE school grades; verify with the district |
| Historical depth | Closed-sale records back to 2006 (51 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 Woods fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Highland Woods with Momentum Realty’s local guides.