Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$4,650,000 -$50,000 (-1.06%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2 Partial Baths
  • 2,446 Sq. Ft.
  • Updated 45 minutes ago
See This Home
Save This Home
See This Home
Save This Home
Embrace the RARE opportunity to own 1.75 acres of open water paradise in the prestigious, gated community of Stirrup Key. Over 750' feet of direct, open Gulf frontage, you'll enjoy spectacular sunrises and sunsets from nearly every vantage point, including a charming sunset gazebo overlooking the iconic Seven Mile Bridge in the distance. The custom Mediterranean-style residence captures the essence of resort living with expansive pavered patios, sparkling elevated pool, and spacious lounging areas absolutely perfect for entertaining against a stunning Gulf backdrop. Five protected basin docks provide sheltered boating access in the marina, while terraced tropical gardens cascade toward the water, lined with mature palms and lush landscaping for a serene coastal ambiance. Inside, soaring cathedral ceilings, wood plantation shutters, and an airy great room with real coral fireplace showcase timeless Keys craftsmanship. The split-bedroom layout ensures privacy, with a luxurious master suite featuring dual closets and skylit bath, plus separate guest quarters. Additional highlights include an elevator, 12,000-gallon cistern, huge garage for cars and golf carts, and a large lower-level storage area with workbenches, pool table, and extra laundry facilities. This gated community, with unique architecture, fewer lots, limited rentals and higher quality restrictions help to sustain a premium and private feel. Only minutes from the Marathon Airport, this one-of-a-kind estate combines open-water grandeur with island tranquility, a true Florida Keys sanctuary.

Full Property Details for 111 Windy Point Cir #& Lot 78

General

  • Price: $4,650,000
  • HOA FEE: $388/month
  • HOA FEE FREQ.: Yearly
  • Taxes: $33,533 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 619002
  • Updated: 5/27/2026
  • Added to Site: 78 day(s) ago

Interior

  • Interior Features: Workshop, Utility Room, Entrance Foyer, Walk-in Closet(s), Built-in Cabinets, Drapes/Blinds Incl, Elevator, Fireplace(s), Sky Light(s), Smoke Alarms, Split Bedroom, Storage, Whirlpool Bath Tub, Window Treatments
  • Appliances: Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, Washer
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 2
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Additional Information

  • Shared Amenities: Community Boat Ramp
  • Pool: Yes
  • Pool Description: Concrete, Heated, Above Ground, Decked, Screened In
  • Security/Safety: Electric Gate, Patrolled Area

Exterior

  • Exterior Features: Rain Gutters, Lighting, Chickee Hut, Fruit Tree(s), Storage, Boat Slip
  • Deck/Patio: Screened Patio, Open Porch/Balcony, Deck, Patio, Screened
  • Porch/Patio/Deck: Screened Patio, Open Porch/Balcony, Deck, Patio, Scree

Parking

  • Garage: Yes
  • Parking Features: Open, Guest, Off Street, Covered, RV Access/Parking, Garage Door Opener

Location

  • Area: 15 - Sombrero Bch Rd to Vaca Cut Gulfside
  • County: Monroe
  • Subdivision: Stirrup Key Sub (52.5)
  • Driving Directions: From US-1, turn onto Aviation Boulevard. Turn onto Stirrup Key Road, go through gate. Continue onto Stirrup Key Boulevard, right onto Windy Point Circle. Home will be on right.

Community

  • Association: Yes
  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air, Ceiling Fans(s)
  • Heating Type: Central, Electric

Structural Information

  • Architectural Style: Above Flood
  • Construction: CBS, Concrete
  • Roof: Tile
  • Windows/Doors: Casement, Sliding Glass Doors, Shutters
  • Square Feet: 2,446
  • Sq. Ft. Source: Property Data Card
  • Year Built: 1988

Lot Features

  • Property View: Open Water View, Bay
  • Lot Size (Acres): 1.75
  • Lot Size (Sq. Ft.): 76,230
  • Lot Size Source: Property Data Card
  • Zoning: RM - Residential Medium

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Bay Front, Gulf Front, Open Water

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $4,650
  • Assoc Fee Freq.: Yearly
  • Tax Amount: $33,533.56
  • Tax Year: 2025

Disclosures and Reports

  • Legal Description: LT 77 & 78 STIRRUP KEY SUBDIVISION PB7-4 STIRRUP KEY & DOCK LOTS 48, 49, 50, 60 AND 61
  • APN: 00333641-007700

Listed by Ocean Sotheby's International, Ally Kelley (727) 459-0493 and Ocean Sotheby's International, Jo Ann Cook (305) 360-7968

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agents

— 111 Windy Point Cir #& Lot 78 —

  • Ally Kelley

    Ocean Sotheby's International

  • Jo Ann Cook

    Ocean Sotheby's International

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 111 Windy Point Cir #& Lot 78

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Stanley Switlik Elementary School
3400 Overseas Highway, Marathon, FL 33050
PK-53.9 mi
Marathon School
350 Sombrero Beach Road, Marathon, FL 33050
6-123.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 111 Windy Point Cir #& Lot 78 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/26/2026
Price Reduced
$4,650,000
-1.06%
MLS
3/10/2026
Listed
$4,700,000
-4.08%
MLS
9/19/2023
Sold
$4,900,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 111 Windy Point Cir #& Lot 78

Year
Property Taxes
Change
Tax Assessment
Change
2024
$28,160
—
$3,188,024
6%
2024
$28,160
85%
$3,016,663
60%
2023
$15,225
11%
$1,885,187
24%
2022
$13,753
6%
$1,514,969
21%
2021
$12,963
—
$1,247,012
3%
2021
$12,963
26%
$1,215,391
23%
2019
$10,258
5%
$987,726
2%
2018
$9,741
2%
$969,310
2%
2017
$9,567
-1%
$949,374
2%
2016
$9,660
1%
$929,848
1%
2015
$9,577
-2%
$923,384
1%
2014
$9,740
1%
$916,056
2%
2013
$9,678
—
$902,518
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 111 Windy Point Cir #& Lot 78

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Ocean Sotheby's International, Ally Kelley (727) 459-0493 and Ocean Sotheby's International, Jo Ann Cook (305) 360-7968

Similar Properties near 111 Windy Point Cir #& Lot 78

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

115 Windy Point Cir, Marathon, FL 33050 - Photo 1
$4,400,000

115 Windy Point Cir  Marathon, FL 33050

  • Single Family
  • Active
  • Updated 13 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,623
    Sq. Ft.
Listed by Ocean Sotheby's International, Ally Kelley and Ocean Sotheby's International, Jo Ann Cook
8700 Overseas Hwy, Marathon, FL 33050 - Photo 1
$4,900,000

8700 Overseas Hwy  #Lot 8  Marathon, FL 33050

  • Single Family
  • Active
  • Updated 13 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,780
    Sq. Ft.
Listed by Ocean Sotheby's International, Jo Ann Cook and Ocean Sotheby's International, Ally Kelley
770 9th St, Key Colony Beach, FL 33051 - Photo 1
$3,850,000

770 9th St  Key Colony Beach, FL 33051

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 3,381
    Sq. Ft.
Listed by Keller Williams Cornerstone Re
431 12th St, Key Colony, FL 33051 - Photo 1
$3,700,000

431 12th St  Key Colony, FL 33051

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 4,369
    Sq. Ft.

Just Listed near 111 Windy Point Cir #& Lot 78

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

7041 Harbor Village Dr, Duck Key, FL 33050 - Photo 1 Just Listed
$599,000

7041 Harbor Village Dr  Duck Key, FL 33050

  • Townhouse
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 3
    Total Baths
  • 900
    Sq. Ft.
Listed by Taylor & Assoc. RE, Inc., Colbert A Taylor
65821 Overseas Hwy, Long Key, FL 33001 - Photo 1 Just Listed
$410,000

65821 Overseas Hwy  #314  Long Key, FL 33001

  • Mobile Home
  • Active
  • Updated 4 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 408
    Sq. Ft.
30860 Malaga Ln, Big Pine Key, FL 33043 - Photo 1 Just Listed
$150,000

30860 Malaga Ln  Big Pine Key, FL 33043

  • Lots/Land
  • Active
  • Updated 1 day ago
  • 0.13
    Acres
Listed by Beycome of Florida, LLC, Steven Koleno
30525 Winifred St, Big Pine Key, FL 33043 - Photo 1 Just Listed
$1,299,000

30525 Winifred St  Big Pine Key, FL 33043

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,774
    Sq. Ft.
Listed by Expert Realty LLC (HQ), Joyce Craul

Price Reduced near 111 Windy Point Cir #& Lot 78

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

112 Bimini Dr, Duck Key, FL 33050 - Photo 1 Price Reduced
-$25,000 (-0.56%)
$4,475,000

112 Bimini Dr  Duck Key, FL 33050

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 3,643
    Sq. Ft.
Listed by Florida Keys Real Estate Group, Brenner Scheel Casey
113 Snapper Creek Dr, Long Key, FL 33001 - Photo 1 Price Reduced
-$10,000 (-1.08%)
$915,000

113 Snapper Creek Dr  Long Key, FL 33001

  • Single Family
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,196
    Sq. Ft.
Listed by Ocean Sotheby's International Realty, Sabrina Wampler & Sarah Ewald
133 Zane Gray Creek Dr, Long Key, FL 33001 - Photo 1 Price Reduced
-$50,000 (-4%)
$1,200,000
Open House

133 Zane Gray Creek Dr  Long Key, FL 33001

  • Single Family
  • Active
  • Updated 6 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,096
    Sq. Ft.
Listed by Keller Williams Realty Premier Properties - Kendall, John Nazzaro PA
31478 Avenue E, Big Pine Key, FL 33043 - Photo 1 Price Reduced
-$15,001 (-2.86%)
$509,999

31478 Avenue E  Big Pine Key, FL 33043

  • Single Family
  • Active
  • Updated 6 hours ago
  • 1
    Bed
  • 1
    Total Bath
  • 557
    Sq. Ft.
Listed by Coldwell Banker Schmitt RE Co., Sabre Mendoza

Recent Sales near 111 Windy Point Cir #& Lot 78

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

14 E Ocean Dr, Marathon, FL 33050 - Photo 1 Sold
$4,100,000

14 E Ocean Dr  Marathon, FL 33050

  • Single Family
  • Closed
  • Updated 12 days ago
  • 4
    Beds
  • 5
    Total Baths
  • 3,477
    Sq. Ft.
Listed by LPT Realty, LLC, Katie Grace Carrillo
Sold by Berkshire Hathaway HomeServices Keys Real Estate, The Owen Lucas Team
254 W Seaview Cir, Duck Key, FL 33050 - Photo 1 Sold
$4,000,000

254 W Seaview Cir  Duck Key, FL 33050

  • Single Family
  • Closed
  • Updated 12 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,519
    Sq. Ft.
Listed by Coldwell Banker Schmitt Lower Keys (KW), Lisa H Ferringo
Sold by Berkshire Hathaway HomeServices Knight & Gardner Realty, Jessica A Celli
341 E Seaview Dr, Duck Key, FL 33050 - Photo 1 Sold
$4,600,000

341 E Seaview Dr  Duck Key, FL 33050

  • Single Family
  • Closed
  • Updated 12 days ago
  • 2
    Beds
  • 4
    Total Baths
  • 2,744
    Sq. Ft.
Listed by Coldwell Banker Schmitt Real Estate Co., Kim Rabito Show
Sold by Trustpoint Realty, LLC, Joseph Suarez
30085 Overseas Hwy, Big Pine Key, FL 33043 - Photo 1 Sold
$4,000,000

30085 Overseas Hwy  #1-7  Big Pine Key, FL 33043

  • Commercial
  • Closed
Listed by Coldwell Banker Schmitt Real Estate Co., Ginger C Henderson

111 Windy Point Circle #& Lot 78, Marathon, FL 33050 (MLS# 619002) is a Single Family property with 3 bedrooms, 2 full bathrooms and 2 partial bathrooms. 111 Windy Point Circle #& Lot 78 is currently listed for $4,650,000 and was received on March 10, 2026. Want to learn more about 111 Windy Point Circle #& Lot 78? Do you have questions about finding other Single Family real estate for sale in Marathon? You can browse all Marathon real estate or contact a Coldwell Banker agent to request more information.

Tour this property