Penn Key Club
Homes for Sale in Upper Matecumbe Key Islamorada, FL
All 25 homes for sale in Upper Matecumbe Key Islamorada, FL · median $1,550,000 · 25 homes for sale in 33036 · Monroe County homes for sale
True comps, carrying-cost math, and listings before the portals.
Nearby homes for sale
No active listings inside PENN KEY CLUB 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.
| Location | Upper Matecumbe Key Islamorada, Monroe County, FL · ZIP 33036 |
|---|---|
| Homes in the community | 32 (FL DOR 2025 assessment roll) |
| Years built | 1952–2016 (median 1959.0) |
| Typical living area | 2,208 sq ft (median) |
| Owner-occupied (homestead) share | 34% |
Data as of September 20, 2026. Listing data provided by Florida Keys MLS, Inc. Information is deemed reliable but is not guaranteed by the MLS to be accurate; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “PENN KEY CLUB key facts,” movewithmomentum.com/neighborhoods/penn-key-club, data as of September 20, 2026.
The market around Penn Key Club
Penn Key Club is too small for its own price trend, so here is the market around it.
In ZIP 33036, 104 homes are on the market and 17% are under contract — a slower corner of Upper Matecumbe Key Islamorada.
Across Monroe County, 1,268 homes are active and 244 pending (16% under contract).
ZIP and county figures describe the wider market, not Penn Key Club specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in PENN KEY CLUB, Upper Matecumbe Key Islamorada
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. Listing data provided by Florida Keys MLS, Inc. Information is deemed reliable but is not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
The Penn Key Club buying strategy.
If we were buying in Penn Key Club 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 Penn Key Club.
A closer look at the Penn Key Club market
The housing stock is 32 homes built between 1952 and 2016, and 34% 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 Penn Key Club. The deal is won or lost on condition, the comps, and the renovation math.
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 Penn Key Club 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 Penn Key Club sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Penn Key Club, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Penn Key Club home worth?
Get a no-obligation home value based on real comparable sales in Penn Key Club, 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 Upper Matecumbe Key Islamorada →
Frequently Asked Questions
How many homes are in Penn Key Club?
What share of Penn Key Club is owner-occupied?
When were the homes in Penn Key Club built?
Who is the best real estate agent for Penn Key Club?
How do I find a top Upper Matecumbe Key Islamorada real estate agent who knows Penn Key Club?
Can Momentum Realty connect me with an agent for Penn Key Club?
Where is Penn Key Club, and what county is it in?
Data sources & freshness
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 33036)) |
| Under-contract shares | Florida Keys MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2008 (20 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 Keys 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 Keys MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how PENN KEY CLUB fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Penn Key Club with Momentum Realty’s local guides.