Aerial view of Stirrup Key Woods

Stirrup Key Woods
Homes for Sale in Marathon, FL

All 178 homes for sale in Marathon, FL · median $1,225,000 · 183 homes for sale in 33050 · Monroe County homes for sale

Community in Marathon · Monroe County · ZIP 33050
51 homesBuilt 1978–2024
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True comps, carrying-cost math, and listings before the portals.

Built fromLive Florida Keys MLS data15 years of closingsFL DOR public recordsUpdated twice daily

Nearby homes for sale

No active listings inside STIRRUP KEY 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.

103 Stirrup Key Woods Road
$565K · 0.0 mi away
3 bd · 2 ba
103 Stirrup Key Woods Road
Listed by Coldwell Banker Schmitt Real Estate Co.
111 Stirrup Key Woods Road #2B2
$340K · 0.0 mi away
2 bd · 1.5 ba
111 Stirrup Key Woods Road #2B2
Listed by Berkshire Hathaway HomeServices Keys Real Estate
205 Stirrup Key Boulevard
$2.25M · 0.2 mi away
4 bd · 3 ba
205 Stirrup Key Boulevard
Listed by Coldwell Banker Schmitt Islamorada
217 Bruce Court
$2.95M · 0.3 mi away
3 bd · 2 ba
217 Bruce Court
Listed by Harrell Real Estate
108 Sunset Drive
$4.50M · 0.3 mi away
3 bd · 4 ba
108 Sunset Drive
Listed by Coldwell Banker Schmitt Real Estate Co
10833 2nd Avenue Gulf Avenue
$979K · 0.3 mi away
5 bd · 3 ba
10833 2nd Avenue Gulf Avenue
Listed by Coldwell Banker Schmitt Islamorada

Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.

STIRRUP KEY WOODS key facts
LocationMarathon, Monroe County, FL · ZIP 33050
Homes in the community51 (FL DOR 2025 assessment roll)
Years built1978–2024 (median 1986)
Typical living area2,462 sq ft (median)
Owner-occupied (homestead) share55%

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, “STIRRUP KEY WOODS key facts,” movewithmomentum.com/neighborhoods/stirrup-key-woods, data as of September 20, 2026.

Live · Stirrup Key Woods Housing Pulse Florida Keys MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 10,000+ customers served · Top 1% in Florida (RealTrends)
Tempo
1
Sold · last 12 mo
10-yr average: about 1 a year
Ownership and context
55%
Owner-occupied · Stirrup Key Woods
30 of 55 parcels homesteaded (FL DOR 2025)
46%
Non-owner-occupied · Stirrup Key Woods
incl. 22% trust or LLC-held · 20% out-of-state
51
Homes in the community
plus 4 vacant residential lots · 55 residential parcels (FL DOR 2025)
Track record · 15 years of records
Est. 1978
Community established
homes built 1978-2024, median 1986 (FL DOR 2025)
2.0%/yr
Turnover rate
about 1 of 51 homes trade a year

The market around Stirrup Key Woods

Stirrup Key Woods is too small for its own price trend, so here is the market around it.

In ZIP 33050, 266 homes are on the market and 14% are under contract — a slower corner of Marathon.

Across Monroe County, 1,268 homes are active and 244 pending (16% under contract).

ZIP and county figures describe the wider market, not Stirrup Key Woods specifically. Momentum Research analysis of MLS records.

Housing distress & ownership in STIRRUP KEY WOODS, Marathon

Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.

Active inventory in distress
0.0%
0 of 8 listings
Distress share trend — 0.0% now (2026-09-14 → 2026-09-19)

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.

If we were buying in Stirrup Key Woods 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 Stirrup Key Woods.

A closer look at the Stirrup Key Woods market

The housing stock is 51 homes built between 1978 and 2024, and 55% 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 Stirrup Key Woods. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

HOA, CDD & Fees

A note on who we are: Momentum Realty is a real estate brokerage. We are not the Stirrup Key Woods homeowners association, its management company or its developer, and we cannot help with dues, gate access, violations, amenity bookings or association documents. To reach the association, check your closing package, the recorded declaration at the county clerk, or search the association’s name at sunbiz.org for its registered agent. Call or message us to buy or sell a home in Stirrup Key Woods.
In short
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Stirrup Key Woods sales matched to your home.

What is your Stirrup Key Woods home worth?

Get a no-obligation home value based on real comparable sales in Stirrup Key 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.

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Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Stirrup Key Woods?
The Florida DOR 2025 assessment roll shows 51 homes plus 4 vacant residential lots in Stirrup Key Woods (public records).
What share of Stirrup Key Woods is owner-occupied?
55% of Stirrup Key Woods parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Stirrup Key Woods built?
Homes in Stirrup Key Woods were built between 1978 and 2024, with a median year built of 1986 (FL DOR 2025 roll).
Who is the best real estate agent for Stirrup Key Woods?
The best agent for Stirrup Key Woods is one who actively works Marathon 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 Stirrup Key Woods.
How do I find a top Marathon real estate agent who knows Stirrup Key Woods?
Share a few details in the form on this page. Momentum Realty has 320+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Stirrup Key Woods and the wider Marathon area.
Can Momentum Realty connect me with an agent for Stirrup Key Woods?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Stirrup Key Woods purchase or sale - no call center and no pressure.
Where is Stirrup Key Woods, and what county is it in?
Stirrup Key Woods is in Marathon, Monroe County, FL, ZIP 33050.

Data sources & freshness

Housing stock & ownershipFlorida DOR assessment roll (street-list match (2 streets, ZIP 33050))
Under-contract sharesFlorida Keys MLS records, as of 2026-09-20
Historical depthClosed-sale records back to 2011 (11 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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Nearby Communities

Explore more neighborhoods near Stirrup Key Woods with Momentum Realty’s local guides.

Stirrup Key Condo0.0 mi awayKey Colony0.3 mi away · median $475K, 5 sales/12 moSea Air Estates0.4 mi away · median $1.90M, 7 sales/12 moOcean Isles Fishing0.5 mi away · median $510K, 4 sales/12 moPalms The (Monroe)0.5 mi away · 36 homes, built 1964–22S Marathon Shores0.5 mi away · 17 homes, built 1946–53Farara Shores0.5 mi awayCoral Colony0.5 mi away · 33 homes, built 1956–23

Browse all neighborhood guides →

Thinking of selling in STIRRUP KEY WOODS? 1 recorded closings (window ending 2026-09-20). See the Monroe County sell-now-or-wait data, what made 201,552 Florida listings fail in the last 12 months, or compare a cash offer vs. listing. Compiled from MLS records; deemed reliable but not guaranteed.
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