Roosevelt Annex
Homes for Sale in Key West, FL
All 228 homes for sale in Key West, FL · median $1,100,000 · 227 homes for sale in 33040 · Monroe County homes for sale
True comps, carrying-cost math, and listings before the portals.
Nearby homes for sale
No active listings inside ROOSEVELT ANNEX 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 | Key West, Monroe County, FL · ZIP 33040 |
|---|---|
| Homes in the community | 23 (FL DOR 2025 assessment roll) |
| Years built | 1999–2001 (median 1999) |
| Typical living area | 1,622 sq ft (median) |
| Owner-occupied (homestead) share | 39% |
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, “ROOSEVELT ANNEX key facts,” movewithmomentum.com/neighborhoods/roosevelt-annex, data as of September 20, 2026.
The market around Roosevelt Annex
Roosevelt Annex is too small for its own price trend, so here is the market around it.
In ZIP 33040, 344 homes are on the market and 15% are under contract — a slower corner of Key West.
Across Monroe County, 1,268 homes are active and 244 pending (16% under contract).
ZIP and county figures describe the wider market, not Roosevelt Annex specifically. Momentum Research analysis of MLS records.
Housing distress & ownership in ROOSEVELT ANNEX, Key West
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 Roosevelt Annex buying strategy.
If we were buying in Roosevelt Annex 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 Roosevelt Annex.
A closer look at the Roosevelt Annex market
The housing stock is 23 homes built between 1999 and 2001, and 39% 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 Roosevelt Annex. 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 Roosevelt Annex 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 Roosevelt Annex sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Roosevelt Annex, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Roosevelt Annex home worth?
Get a no-obligation home value based on real comparable sales in Roosevelt Annex, 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
How many homes are in Roosevelt Annex?
What share of Roosevelt Annex is owner-occupied?
When were the homes in Roosevelt Annex built?
Who is the best real estate agent for Roosevelt Annex?
How do I find a top Key West real estate agent who knows Roosevelt Annex?
Can Momentum Realty connect me with an agent for Roosevelt Annex?
Where is Roosevelt Annex, and what county is it in?
Data sources & freshness
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 33040)) |
| Under-contract shares | Florida Keys MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2000 (34 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.
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See how ROOSEVELT ANNEX fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Roosevelt Annex with Momentum Realty’s local guides.