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Back 5222 Winding Way
Off Market

5222 Winding Way

Siesta Key FL 34242

2
2
1
1900 sq. ft.
6000 sq. ft.
Single-Family
Last sold for $550,000
Bob MoffattBob Moffatt, last sold this property on 12 November 2025 after 106 days on market.

Overview

Opportunity knocking loudly! Here it is the least expensive pool home on Siesta Key. You will approach under a charming, canopy lined street. This 2BR/2BA is ready for someone to put their finishing touches on it after hurricane damage. Walls have been removed from 4 ft down, kitchen cabinets and counter removed. Nice Crown molding. Electrical was rewired and raised. Replumbed in 2020. Tankless water heater is 1 year old. A/C was new in 2023. Ductwork was replaced. Great Lap pool has new pool pump. Roof was patched and not leaking. This fabulous quiet location is a half a mile to the #1 Siesta Key Beach, this is your new place in the sun. Island living at its best.

Features

2 bedrooms
2 bathrooms
1 carspace
1 carport space
1900 sq. ft. floor area
6000 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 2 bedroom single-family properties sold in Siesta Key over the last 12 months, the estimated median property value of 5222 Winding Way is $742.5k.

Median value
$742.5k
Estimated value range
$500k - $2.25m
Median days on market
173
Estimated value trend
-33%
decrease over the last 12 months
Average days on market is based on recent, comparable sales in Siesta Key. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 5222 Winding Way

2025
Sold
$550,000
12 Nov 2025 by Bob Moffatt, of MICHAEL SAUNDERS & COMPANY
2010
Sold
$232,000
23 Jun 2010 by Sarah McGuire, of MICHAEL SAUNDERS & COMPANY

Happy sellers in Siesta Key

89%
89% of sellers in Siesta Key reported that their sale price either exceeded or met their price expectations.

Siesta Key stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 12 reviews in Siesta Key over the last 12 months.

Local market activity for 2 bedroom single-family properties in Siesta Key

In the last 12 months, 14 two-bedroom single-family properties similar to 5222 Winding Way, have been sold.

This represents a 7% decrease in two-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Siesta Key

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Mike Martino

Sellers who recommend Mike Martino have praised them for being local expert, detail-oriented, clear communication, hard-working, supportive, reliable, and honest

  •   5   (85 reviews)
  •  4 Reviews in Siesta Key
  •  7 Sales in Siesta Key
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Steve Abbe

Sellers who recommend Steve Abbe have praised them for being local expert, responsive, clear communication, supportive, reliable, patient, and well-prepared

  •   5   (152 reviews)
  •  3 Reviews in Siesta Key
  •  4 Sales in Siesta Key
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Maurice Menager

Sellers who recommend Maurice Menager have praised them for being local expert, responsive, clear communication, supportive, pleasant, great negotiation, and detail-oriented

  •   5   (51 reviews)
  •  1 Review in Siesta Key
  •  6 Sales in Siesta Key
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Christa Spalding

Christa Spalding is a recommended agent for Siesta Key.  They have 6 local sales and collected 1 local review across the last 12 months.

  •   5   (13 reviews)
  •  1 Review in Siesta Key
  •  6 Sales in Siesta Key
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