5 Hilton Haven Drive, Key West, FL 33040
Sources: Florida Keys MLS (listings + 12-mo closed sales), FEMA, modeled insurance. Interpretation: Momentum Research. Data notes
As of October 1, 2026, 5 Hilton Haven Drive in Hilton Haven Sec 1 A (2.0), Key West is listed at $1,695,000. That sits within a few percent of Hilton Haven Sec 1 A (2.0)'s median closed sale of $1,550,000 over the last 12 months (31 recorded sales). It came to market within the past week. Listing facts: built in 1955, a private pool, waterfront, no HOA. Figures are from the MLS record and county data; deemed reliable but not guaranteed.
- No CDD assessment on record
- Built 1955 · 71 yrs
- Active listing
- No HOA reported by the listing (confirm)
About this home
LOCATION! Situated on Garrison Bight, across the canal from the Key West Yacht Club, 5 Hilton Haven Dr. provides the best boating access on Key West.
Tremendous opportunity for a buyer with a vision. The 4-bedroom, 4.5 bath, 2,027 sq. ft.
home is currently divided into 4 separate units in need of extensive repair. Or this home could be a good candidate for rebuilding as your single-family dream home with a pool and 60' of dockage. Tucked away on one of Key West's few private drives, the home enjoys limited traffic and added privacy.
Equipped with 2 electric meters and 9,058 sq. ft. lot, this property offers options and flexibility for bringing your vision to life.
All 7 photos
Description provided by Coldwell Banker Schmitt Real Estate Co. (KW) and reproduced from the MLS; not independently verified.
Every fact, sourced
Listing data, public records, our calculations, and what to verify — each fact shown once. Estimates and calculations shown are for general information only, are not appraisals or advice, and should be independently verified.
Listing facts MLS
Public records & third-party data
Calculated estimates
Buyer should verify Buyer verify
Estimated monthly payment
- Principal & interest $9,278/mo 79%
- Taxes $1,483/mo 13%
- Insurance $920/mo 8%
$11,681/mo at 20% down, 30-yr @ 7.28% · edit any field to update.
Editable estimate — not a loan offer. Estimates only; see data & estimate notes.
Flood zone & elevation
Sourced environmental data for the parcel. Confirm with FEMA and your insurer.
Not yet verified for this address. Look up the parcel at msc.fema.gov before relying on any flood assumption.
Approximate parcel elevation from USGS; confirm exact elevation with a survey.
Monroe County is on the Florida coast; wind coverage is a major part of the premium. Premiums and coverage vary by home (roof age, wind mitigation, claims history); obtain a quote from a licensed insurer.
Natural hazard risk
FEMA National Risk Index for Monroe County, FL: overall Relatively Moderate. Ratings compare this county with every county in the United States for expected annual loss from each hazard.
Source: FEMA National Risk Index (county level, hazard risk ratings only). Ratings describe the county, not this parcel; the flood zone shown above is parcel-specific. Verify insurance requirements with your lender and agent.
Internet & broadband
Address-level fiber service is not confirmed for this home. Check the FCC National Broadband Map (broadbandmap.fcc.gov) or the provider for this address.
Cable broadband is common in Florida and Georgia towns but not confirmed for this address; verify with the provider.
5G home internet and satellite service depend on the exact location; check coverage for this address.
Pricing & the Sugarloaf Shores (17.0) market
How this home is priced against recent nearby sales, and where Sugarloaf Shores (17.0) has been over 25 years. Momentum Research analysis of Florida Keys MLS records; closed sales, deemed reliable but not guaranteed. Estimates only; see data notes.
Median sale price by year
12-month median closed price, 2012–2026.
Market Heat by year (0–100)
Momentum Market Heat, 2013–2026. Now 42 (normal).
This home’s history
- 1955BuiltPer public record
- Oct 2, 2026First seen on movewithmomentum.comObserved at $1,695,000
- NowActiveCurrently for sale
Build year is from public record. The MLS list date is approximate (today minus the cumulative days on market the MLS reports, which can span relistings). Other milestones reflect movewithmomentum.com’s own observations since we began tracking this listing and are not the MLS listing history; dates and prices are deemed reliable but not guaranteed.
Price & listing history
Building permits
Comparable recent sales
No closed sales of a similar home within about 10 miles in Monroe County in the last 18 months are in our MLS data set, so this page shows no comparable-sales median or automated estimate for Hilton Haven Sec 1 A (2.0). A licensed Momentum Realty agent can prepare a property-specific comparative market analysis on request.
Momentum Property Score
48/100 is below average across the objective indicators below. It reflects only those measures — not the home’s quality, condition, or desirability.
A 0-100 score built from objective property and market data: flood risk, insurance, pricing, supply, affordability, and recent sales. Higher means more measures line up in a buyer’s favor. It reflects only the factors below.
Coverage: 4 of 8 indicators had valid data for this home; indicators without data are left out, not scored as zero. Momentum Scores are objective, rules-based indicators computed from listing facts, public records, and recent comparable sales. They do not measure property condition, quality, or investment suitability, and they are not appraisals, valuations, investment advice, or judgments about a neighborhood or who should live there. Verify independently.
The Momentum read
Recent Sugarloaf Shores (17.0) sales closed near 92.3% of original asking.Why it matters: the community’s own record shows how far opening prices typically move, and how often buyers compete without financing.Momentum Research analysis of Florida Keys MLS records, community-level, 12 months ending September 20, 2026. Aggregates only; deemed reliable but not guaranteed.
What’s unique here: one of only 1167 active listings in Sugarloaf Shores (17.0), no CDD assessment.
Jump to: About this home · Every number, sourced · Monthly cost · Flood & risk · History · FAQ
Updated October 1, 2026 · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
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Listed by Coldwell Banker Schmitt Real Estate Co. (KW) · MLS # 621480
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Similar homes for sale near Hilton Haven Sec 1 A (2.0)
Active listings nearby at a comparable size and price. Listings held by brokerages other than Momentum Realty are marked with the listing broker. Deemed reliable but not guaranteed.
Newest listings in Hilton Haven Sec 1 A (2.0)
- 98381 Windward Avenue · $487,500 · 2 bd / 2.0 ba · listed October 1, 2026 (courtesy of Berkshire Hathaway HomeServices Keys Real Estate - Islamorada)
- 2506 Seidenberg Avenue · $799,000 · 3 bd / 3.0 ba · listed October 1, 2026 (courtesy of Keller Williams Realty Professionals (KW))
- 1716 Laird Street · $2,195,000 · 3 bd / 2.0 ba · listed October 1, 2026 (courtesy of The Agency Florida Keys)
- 701 Spanish Main Drive #455 · $399,999 · 1 bd / 1.0 ba · listed October 1, 2026 (courtesy of Coldwell Banker Schmitt RE Co.)
- 1901 S Roosevelt Boulevard #208E · $1,349,000 · 3 bd / 2.0 ba · listed October 1, 2026 (courtesy of Truman & Co. (KW))
- 1422 Boca Chica Road · $1,259,000 · 3 bd / 2.0 ba · listed October 1, 2026 (courtesy of Realty Executives Florida Keys Old Town)
Recently off market in Hilton Haven Sec 1 A (2.0)
- 990 41st Street Gulf #10 · last listed $3,475,000 · 2026-10-01
- 98202 Windward Avenue · last listed $399,000 · 2026-10-01
- 87 Marina Avenue · last listed $749,000 · 2026-10-01
- 615 Cuda Lane · last listed $1,349,000 · 2026-10-01
- 4016 Dorn Road · last listed $775,000 · 2026-10-01
- 339 Windley Road · last listed $1,200,000 · 2026-10-01
Just listed: new homes for sale in the Florida Keys in the last 48 hours · updated hourly · RSS · The Florida Keys market today: new listings, price cuts, pendings
More on Monroe County
Explore Monroe County
Browse market data, schools, taxes, and homes for sale across the county.
Assigned schools
Schools currently assigned to this address in Monroe County, provided as neutral factual data. Assignments can change — confirm current zoning with the school district. This is not a statement about the home's suitability for any person or family.
City, county & community guides
Where this home sits, with links to the matching guides. General reference only.
Groceries, dining, and parks for this city — see the city guide.
View →Schools, taxes, and services are county-administered — see the county guide.
View →Amenities and HOA/CDD detail on the neighborhood guide.
Buyer research checklist
Items worth confirming for 5 Hilton Haven Drive, chosen from what the record shows. This is general guidance, not advice about this specific property.
- Built in 1955 (71 years): ask for the roof and HVAC replacement dates — insurers commonly ask for roof age on homes this old, and it changes the premium.
- The listing reports no HOA: confirm with the county record that no deed restrictions or mandatory association apply to this parcel.
- Look up the parcel on FEMA's Flood Map Service Center and confirm with your insurer whether flood insurance is required.
- Get a homeowners insurance quote for this specific address in Monroe County; a wind-mitigation inspection and, on older homes, a four-point inspection can change the premium.
- Private pool: confirm the barrier or alarm meets the state residential pool safety code and ask for pump, heater, and resurfacing records.
- Waterfront: confirm seawall or dock condition and permits, and ask who owns and maintains the shoreline.
- Confirm square footage and room dimensions independently.
- Order a survey to confirm lot boundaries and easements.
- Review permit history with the county.
- Property taxes: the estimate on this page (about $17,798/yr) assumes reassessment at the list price; the seller's current bill is not a guide Exemptions and portability change the actual bill — confirm with the county property appraiser.
- Confirm school zoning directly with the district.
Data sources & freshness
| Listing record | Florida Keys MLS, refreshed hourly (last: October 1, 2026) |
| Comparable sales | Fewer than 3 defensible closed sales within about 10 miles in Monroe County — no medians or automated estimate shown |
| Flood zone & elevation | Not verified for this address — look it up at msc.fema.gov |
| Taxes & monthly cost | Typical county effective rate applied to the list price; an estimate, not a bill |
| Insurance figure | Modeled estimate; obtain a real quote before offering |
| Schools | 2025-26 district assignments; verify with the district |
Momentum Research lines are our own analysis of Florida Keys MLS records; MLS data is deemed reliable but not guaranteed. Estimates are informational, not appraisals or advice. Methodology: how Momentum scores are computed.
Frequently asked questions
How big is 5 Hilton Haven Drive and when was it built?
Per the listing record, 5 Hilton Haven Drive was built in 1955 and has 4 bedrooms and 4.5 bathrooms. Living area and lot size come from the MLS record and should be verified against the county property appraiser.
What community is 5 Hilton Haven Drive in?
5 Hilton Haven Drive is in Hilton Haven Sec 1 A (2.0) in Key West, Monroe County. Too few comparable closed sales exist nearby for this page to show local sales statistics; a licensed agent can prepare a comparative market analysis.
Does 5 Hilton Haven Drive have an HOA?
The listing reports no HOA. Confirm with the county record that no deed restrictions or mandatory association apply to the parcel.
Why might property taxes on 5 Hilton Haven Drive differ from the current owner's?
The estimate on this page (about $17,798 per year) assumes reassessment at the list price less the homestead exemption. Florida reassesses a home after it sells; for a homesteaded seller the Save Our Homes cap on their assessment does not transfer, and a buyer's own exemptions and portability are applied separately, so the two bills usually differ. Any tax figure shown here is an estimate, not the actual bill — confirm with the county property appraiser and tax collector.
Is 5 Hilton Haven Drive in a flood zone?
A flood designation has not been verified for this address. Look up the parcel on FEMA's Flood Map Service Center (msc.fema.gov) and confirm with your insurer.
Can I rely on the figures on this page?
No. Estimated taxes, insurance, payments, and any market or comparable-sales summary are opinions and estimates for general information only and should not be relied upon. Verify all information independently before making any decision.
See 5 Hilton Haven Drive in person
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Opinion & estimate — do not rely on this page. Any figure on this page that is not a verbatim fact from the listing or a public record — including estimated property taxes, insurance, CDD/HOA amounts, mortgage payments, comparable-sales summaries, and market statistics — is an opinion and estimate provided for general informational purposes only. These figures may be inaccurate or out of date, are not appraisals, valuations, or financial, legal, tax, or investment advice, and should not be relied upon. Do not make any purchase, offer, financing, or other decision based on this page. Independently verify everything — price, square footage, lot size, year built, taxes, CDD/HOA, flood status, school assignments, permits, and community rules — with the listing broker, the county, your lender, a licensed inspector, an insurer, and your own advisors before acting.
Estimate methodology. Tax estimates apply county millage to the list price (less the homestead exemption where the parcel is matched to the certified roll) and will differ from the actual assessed bill. Cost and market figures are derived from available data and simple calculations, not a professional appraisal. We make no representation that any estimate reflects fair market value.
Equal Housing Opportunity. Content on this page is compiled from public records, MLS data, and automated sources and may contain errors or be out of date. It is general information only, not a representation about any specific property, community, builder, or association. Verify information independently before relying on it. Momentum Realty supports the Fair Housing Act and does not discriminate on the basis of race, color, religion, sex, handicap, familial status, national origin, sexual orientation, or gender identity. Information about schools, distances, and amenities is provided as neutral factual data to help you research the property and is not a statement about who should or should not live here or the suitability of the home or neighborhood for any person or group. School data may change — confirm current assignments with the school district.
Found an error? If you are the owner, listing agent, or a party to this property and believe any information is inaccurate, email and we will review and correct or remove it promptly.
Automated content. Some summaries, distances, and estimates on this page are generated automatically from public and proprietary data sources and may contain errors or omissions. We strive for accuracy but cannot guarantee the completeness or accuracy of any information. Verify anything important independently.
No warranty; measurements & photos. No guarantee, warranty, or representation of any kind is made regarding the completeness or accuracy of any information, descriptions, or measurements on this page — including square-footage measurements and property condition — all of which should be independently verified through appropriate means, including in-person inspection and public records. Photographs may be virtually staged or digitally enhanced and may not reflect actual property conditions. Momentum Realty and its agents expressly disclaim any liability in connection with the information provided.
MLS / IDX. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Florida Keys MLS, Inc. Internet Data Exchange. Real estate listings held by brokerage firms other than Momentum Realty are marked with the listing broker's name and include the name of the listing agent. Data provided is deemed reliable but is not guaranteed by the MLS to be accurate. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Source: Florida Keys MLS, Inc.. © 2026 Florida Keys MLS, Inc. All rights reserved.
Listing data is deemed reliable but is not guaranteed and is subject to change or withdrawal without notice. Square footage and lot size are approximate. Real estate brokerage services provided by Momentum Realty, licensed in Florida and Georgia. © 2026 Move With Momentum LLC.