355 Stirrup Key Blvd, Marathon, FL 33050
Property image
Property image
FOR SALE
NEW - 2 HRS AGO
0.44 ACRES

$3,300,000

  • 4 Beds
  • 3.5 Baths
  • 2,540 sqft (on 0.44 acres)

355 Stirrup Key Blvd, Marathon, FL 33050

Est. Mortgage $21,041/mo*
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Home Highlights

Single-Family Home
Built in 1994
0.44 acre lot
$1,299/sqft
Garage
HOA $1,200/mo

Local Information

  • Map ViewExplore the area around 355 Stirrup Key Blvd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Welcome to Sunset Anchorage, a beautifully renovated open-water home in the exclusive gated community of Stirrup Key. Set on an expansive lot and a half, this three-story CBS home offers exceptional privacy, protected dockage, a private pool, and sweeping Gulf views with spectacular sunsets.
Extensively updated, the home features a brand-new kitchen with custom cabinetry, a custom bar, updated flooring, new impact windows and doors, and new A/C units. New Hardie board siding accents the front exterior, adding texture and architectural character.
The main level features the primary suite with a newly expanded and completely renovated bathroom. An additional guest bedroom enjoys marina views with a full bath nearby. A newly extended covered back porch off the living and dining rooms offers outdoor seating and dining overlooking the pool and Gulf. Upstairs, a secondary primary suite features a private full bath and walk-out balcony with stunning bay views, while another guest bedroom and half bath also enjoy expansive open-water views.
Downstairs, a spacious covered patio and newly built tiki bar create additional entertaining space poolside. The pool has been beautifully re-tiled and refinished with new equipment, including a heater and chiller. A redone waterfront observation deck provides easy kayak access, views over the sandy bay bottom, and a front-row vantage point for spectacular sunsets.
Protected dockage is just across the street in Stirrup Key's private marina. Boat slip D41 includes a new concrete walk-out dock and a 15,000-lb boat lift, with instant bay access and quick ocean access via Vaca Cut or Seven Mile Bridge.
Additional features include a metal roof, garage, ground-floor storage, a fenced dog run, and mature tropical landscaping highlighted by a grove of gumbo limbo trees.
Sunset Anchorage brings together open-water views, protected boating, privacy, and unforgettable Florida Keys waterfront living-offered turnkey and ready to enjoy from day
Last check for updates: about 2 hours ago
Listing courtesy of Lisa Wiebe, (561) 386-4952
Coldwell Banker Schmitt Real Estate Co.
Source: FLKMLS, MLS#621321
Also Listed on FLKMLS.

Home Details for 355 Stirrup Key Blvd

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2540 Square Feet
Appliances & Utilities
Utilities: Water Separate Meter, Elect Separate MeterAppliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Freezer, Ice Maker, Stainless Steel Appliance(s)DishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Has Heating Unspecified TypeHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Has Heating Unspecified Type
Windows, Doors, Floors & Walls
Flooring: Tile, Laminate
Levels, Entrance, & Accessibility
Floors: Tile, Laminate
View
No View
Security
Security: Security Gate

Exterior Features

Exterior Home Features
Patio / Porch: Open Porch/Balcony, DeckFencing: FencedExterior: Bar, Chickee Hut, Fruit Tree(s), Rain Gutters, Lighting, StorageHas a Private Pool
Parking & Garage
Has a GarageParking: Garage
Pool
Pool: In GroundPool
Frontage
WaterfrontOn Waterfront

Days on Market

Days on Market: <1 day on Trulia

Property Information

Year Built
Year Built: 1994
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: CBSNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00333641007100Additional Parcels Description: 00333641-014600

Price & Status

Price
List Price: $3,300,000Price Per Sqft: $1,299

Active Status

MLS Status: Active

Location

Direction & Address
City: MarathonCommunity: Stirrup Key Sub (52.5)

Agent Information

Listing Agent
Listing ID: 621321

Building

Building Area
Building Area: 2540 Square Feet

Community

Community Features: Community Boat Ramp, Bike PathsNot Senior Community

HOA

HOA Fee Includes: Common Area Mnt, SecurityHas an HOAHOA Fee: $1,200/Monthly

Lot Information

Lot Area: 0.44 acres

Offer

Listing Terms: Cash, Conventional

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 621321

Additional Information

Community Boat RampBike Paths

Around this home

What Locals Say about Marathon

At least 61 Trulia users voted on each feature.

  • 83 % Say car is needed

  • 79 % Say people would walk alone at night

  • 76 % Say parking is easy

  • 72 % Say it's quiet

  • 70 % Say it's dog friendly

  • 70 % Say yards are well-kept

  • 68 % Say there's holiday spirit

  • 61 % Say it's walkable to restaurants

  • 53 % Say there's wildlife

  • 53 % Say they plan to stay for at least 5 years

  • 51 % Say there are community events

  • 49 % Say kids play outside

  • 45 % Say neighbors are friendly

  • 37 % Say it's walkable to grocery stores

  • 36 % Say there are sidewalks

  • 29 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • 4yrv5tc4qr
    "Seafood festival, theater, music festival, turtle releases, homecoming parade, 4th of July fireworks on the beach"
    1
    Flag
  • Ingridfox
    "people love walking dogs on the beach and dog dog park at Sombrero Beach. A lot of restaurants are dog friendly. This is a great place for dog owners. "
    1
    Flag
  • C E.
    "There is no place for kids to hang out really except for the skate park. There are no malls, no skating rinks, no places for kids to meet safely. "
    1
    Flag
  • Jan M.
    "We have basic public transportation. I’d take a taxi anywhere in town. .............................,,"
    0
    Flag
  • Erin F.
    "There’s plenty of grass, sidewalks and quiet roads to walk along.. plus the public beach is always a dogs favorite adventure.. just pick up after your dog!"
    2
    Flag
  • Thurmankolb
    "Yes! Dog park just down the street. Lots of neighbors know each other by our dogs. Great vets n Marathon and good groomer."
    6
    Flag
  • Thurmankolb
    "Lots of community events and activities. Fishing tournaments, seafood festival, school carnivals, etc... "
    2
    Flag
  • Jamie B.
    "Everyone gets together for the kids at Halloween. We have a community park with special events planned for the kids and the beach is the sight for a special 4th of July. "
    0
    Flag
  • Abiezer31
    "Of course ,the neighbors the owner and dog are very nice I’m very proud living in my house.and this neighborhood "
    3
    Flag
  • Darren S.
    "I live off the beaten path across the street from a golf course. It's very quiet and tranquil. throb marinas surrounding the property and can walk to All shops and stores."
    0
    Flag
  • Cyndiepalmer
    "We are a friendly neighborhood. You walk your street and say Hi anytime. It is a safe street to live "
    0
    Flag
  • Ksperkinson
    "Safe clean near ocean good police pet friendly hospital is coming along in the construction have contract here at hospital looking forward to finding a good place for 3 months"
    0
    Flag
  • Stephanie M.
    "A lot of kids and cars. A fire station that is noisey but nice. Lizards everywhere. There is one hotel on this small island. There are A lot of Vacation homes here and crab catchers. When it rains you can't see the road."
    0
    Flag
  • Lb2071
    "water front community , is a small island called Flamingo Island. We have a 9 hole golf course and just 5 minutes from Publix and Kmart. Sombrero beach is right at the outset of the canals on the Atlantic ocean and the people are very loving and friendly."
    0
    Flag
  • Gonzalez8834
    "Marathon is a great place to life and have a family, very safe, quiet and full of great people. ......"
    0
    Flag
  • Tom A. C. M.
    "I live here (14 years) and love the area. Close accessibility to shopping, schools, churches, golf, beach, walking, biking. "
    0
    Flag
  • Anne K.
    "Lived here for many years and is one of the best places to live in Marathon. Conveniently located near schools, parks, shopping and beach just minutes away."
    0
    Flag
  • Debra G.
    "Only 8 miles from Marathon. Away from the winter traffic, airport noise. Crystal clean, flow through canals. Great place to vacation and a great place to live. "
    0
    Flag

Market trends in Marathon

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
255
7MoM

Home Value

Trulia Estimate
$3.09M
Since last month
Increased$37K (+1.2%)
Since last year
Increased$174K (+5.8%)
Since last sale
Increased$672K (+26.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +100% in the last 10 years
MonthEstimated value
2026
September 2026$3.17M
August 2026$3.12M
July 2026$3.13M
June 2026$3.14M
May 2026$3.05M
April 2026$3.04M
March 2026$3.06M
February 2026$3.04M
January 2026$2.96M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
101 Windy Point Cir, Marathon, FL
0.06
Single-Family Home
$2,675,000
12/23/25
4
2.5
3,260
358 Stirrup Key Blvd, Marathon, FL
0.05
Single-Family Home
$2,155,000
06/25/26
3
2
2,534
351 Stirrup Key Blvd, Marathon, FL
0.08
Single-Family Home
$1,800,000
06/29/26
3
3
1,802
199 Stirrup Key Blvd, Marathon, FL
0.47
Single-Family Home
$2,028,000
06/23/26
5
5
3,467
359 Stirrup Key Blvd, Marathon, FL
0.02
Single-Family Home
$2,950,000
12/08/25
3
2
1,995
111 Brian Rd, Marathon, FL
0.74
Single-Family Home
$3,250,000
04/09/26
4
3.5
4,256
11243 3rd Ave, Marathon, FL
0.83
Single-Family Home
$1,500,000
10/16/25
5
4
2,416
211 Bruce Ct, Marathon, FL
0.79
Single-Family Home
$2,250,000
08/31/26
4
5
1,800
209 E Bruce Ct, Marathon, FL
0.78
Single-Family Home
$2,300,000
12/12/25
4
2
1,852

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
358 Stirrup Key Blvd, Marathon, FL 33050
0.05
$2,155,000
3
2
2,534
Recently Sold
359 Stirrup Key Blvd, Marathon, FL 33050
0.02
$2,950,000
3
2
1,995
Recently Sold
101 Windy Point Cir, Marathon, FL 33050
0.06
$2,675,000
4
2.5
3,260
Recently Sold
351 Stirrup Key Blvd, Marathon, FL 33050
0.08
$1,800,000
3
3
1,802
Recently Sold
347 Stirrup Key Boulevard, Marathon, FL 33050
0.10
$2,681,100
4
3
2,496
Off Market
339 Stirrup Key Blvd, Marathon, FL 33050
0.11
$3,457,300
4
4
2,521
Off Market
Windy Point, Marathon, FL 33050
0.10
-
-
-
-
Off Market
111 Windy Point Cir, Marathon, FL 33050
0.12
$4,083,900
3
3
2,446
Off Market
105 Pirates Cove Dr, Marathon, FL 33050
0.16
$2,041,100
4
2.5
2,720
Off Market
Pirates Cove Dr, Marathon, FL 33050
0.17
-
-
-
-
Off Market
120 Pirates Cove Dr, Marathon, FL 33050
0.21
$2,199,000
4
4
3,476
For Sale

Price and Tax history

DateEventPrice
Sep 17, 2026
Source: FLKMLS #621321
Listed For Sale
$3,300,000
May 17, 2022
Source: FLKMLS #599538
Sold
$2,500,000
Mar 30, 2022
Source: Key West AOR #599538
Contingent
$2,870,000
Mar 14, 2022
Source: MLKAR #599538
PendingToActive
$2,870,000
Mar 14, 2022
Source: FLKMLS #599538
Contingent
$2,870,000

LGBTQ Local Legal Protections

Lisa Wiebe, Coldwell Banker Schmitt Real Estate Co.
Agent Phone: (561) 386-4952
MLS Internet Data Exchange (IDX) information is provided exclusively 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, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys MLS.

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Frequently asked questions about 355 Stirrup Key Blvd

  • What is the estimated monthly payment for 355 Stirrup Key Blvd?
    Based on a $3,300,000 list price with 20% down at today's rates, the estimated monthly payment for 355 Stirrup Key Blvd in Marathon, FL is approximately $20,347 (about $18,017 principal & interest, $2,255 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Marathon?
    Residents describe Marathon, FL as easy to park in, quiet, and dog-friendly. Most residents say you need a car. See homes for sale in Marathon, FL.
  • What are the closest schools to 355 Stirrup Key Blvd?
    The closest schools to 355 Stirrup Key Blvd in Marathon, FL are Marathon School (Middle/High, rated 5/10), Stanley Switlik Elementary School (Pre-K, rated 5/10).
  • What is 355 Stirrup Key Blvd estimated to be worth?
    Trulia's estimated value for 355 Stirrup Key Blvd in Marathon, FL is $3,091,300.
  • Does 355 Stirrup Key Blvd have air conditioning?
    Yes, 355 Stirrup Key Blvd in Marathon, FL has air conditioning.
  • Does 355 Stirrup Key Blvd have a pool?
    Yes, 355 Stirrup Key Blvd in Marathon, FL has a pool.
355 Stirrup Key Blvd, Marathon, FL 33050 is a 4 bedroom, 4 bathroom, 2,540 sqft single-family home built in 1994. This property is currently available for sale and was listed by FLKMLS on Sep 17, 2026. The MLS # for this home is MLS# 621321.