Osprey Recently Sold Homes
26 homes sold in Osprey in the last month, median sold price $595,000.
Recent sales in Osprey.
Most recent sales first.
Sold$150,000Sold Oct 15, 2026
- 1 bed
- 1 bath
- 586 sqft
701 Pine Run Drive #701
Condo · Osprey, FL 34229
MLS# A4700416 · Listing courtesy of PAT WILLIAMS REALTY, LLC
Sold$675,000Sold Oct 15, 2026
- 4 beds
- 3 baths
- 2,683 sqft
130 Willow Bend Way
House · Osprey, FL 34229
MLS# TB8548160 · Listing courtesy of RE/MAX ALLIANCE GROUP
Sold$255,850Sold Oct 14, 2026
- 2 beds
- 2 baths
- 1,165 sqft
1801 Highland Road
Townhome · Osprey, FL 34229
MLS# N6140508 · Listing courtesy of RE/MAX ALLIANCE GROUP
Sold$2,630,000Sold Oct 14, 2026
- 3 beds
- 4 baths
- 2,665 sqft
14401 Masthead Drive
House · Osprey, FL 34229
MLS# A4684834 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
Sold$615,000Sold Oct 14, 2026
- 2 beds
- 2 baths
- 2,143 sqft
5100 Jessie Harbor Drive #304
Condo · Osprey, FL 34229
MLS# A4690942 · Listing courtesy of COLDWELL BANKER REALTY
Sold$210,000Sold Oct 14, 2026
- 2 beds
- 2 baths
- 1,325 sqft
110 Woodland Place #110
Condo · Osprey, FL 34229
MLS# A4696738 · Listing courtesy of COLDWELL BANKER REALTY
Sold$665,000Sold Oct 14, 2026
- 3 beds
- 3 baths
- 2,837 sqft
264 Woods Point Road #264
Condo · Osprey, FL 34229
MLS# A4703025 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
Sold$1,050,000Sold Oct 14, 2026
- 3 beds
- 3 baths
- 2,203 sqft
401 N Point Road #903
Condo · Osprey, FL 34229
MLS# A4705080 · Listing courtesy of COLDWELL BANKER REALTY
Sold$555,000Sold Oct 12, 2026
- 3 beds
- 2 baths
- 1,731 sqft
547 Meadow Sweet Circle
House · Osprey, FL 34229
MLS# A4701316 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
Sold$6,000,000Sold Oct 12, 2026
- 6 beds
- 6 baths
- 8,621 sqft
112 Osprey Point Drive
House · Osprey, FL 34229
MLS# A4702047 · Listing courtesy of DOUGLAS ELLIMAN
Sold$399,000Sold Oct 8, 2026
- 2 beds
- 2 baths
- 1,346 sqft
329 Bay Vista Avenue
House · Osprey, FL 34229
MLS# A4699464 · Listing courtesy of THE SHORELINE FL REALTY LLC
Sold$575,000Sold Oct 7, 2026
- 3 beds
- 3 baths
- 2,203 sqft
401 N Point Road #603
Condo · Osprey, FL 34229
MLS# A4671958 · Listing courtesy of COLDWELL BANKER REALTY
Sold$1,612,500Sold Oct 7, 2026
- 5 beds
- 8 baths
- 5,986 sqft
916 Macewen Drive
House · Osprey, FL 34229
MLS# A4698153 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY
Sold$2,910,000Sold Oct 6, 2026
- 3 beds
- 4 baths
- 3,122 sqft
321 Lookout Point Drive
House · Osprey, FL 34229
MLS# A4697345 · Listing courtesy of COLDWELL BANKER REALTY
Sold$300,000Sold Oct 5, 2026
- 3 beds
- 2 baths
- 1,430 sqft
4213 Expedition Way #107
Condo · Osprey, FL 34229
MLS# A4698337 · Listing courtesy of DALTON WADE INC
Sold$690,000Sold Oct 4, 2026
- 3 beds
- 3 baths
- 2,583 sqft
678 Faith Avenue
House · Osprey, FL 34229
MLS# A4674865 · Listing courtesy of GENEROUS PROPERTY
Sold$850,000Sold Oct 1, 2026
- 4 beds
- 3 baths
- 2,468 sqft
144 Park Trace Boulevard
House · Osprey, FL 34229
MLS# A4704235 · Listing courtesy of GOLF & BAY PROPERTIES LLC
Sold$309,000Sold Sep 29, 2026
- 3 beds
- 2 baths
- 1,528 sqft
4304 Expedition Way Way #105
Condo · Osprey, FL 34229
MLS# N6143250 · Listing courtesy of EXIT KING REALTY
Sold$759,000Sold Sep 29, 2026
- 3 beds
- 3 baths
- 2,778 sqft
401 Point Road #504
Condo · Osprey, FL 34229
MLS# A4696459 · Listing courtesy of MICHAEL SAUNDERS & COMPANY
Sold$1,075,000Sold Sep 29, 2026
- 3 beds
- 2 baths
- 2,255 sqft
292 Turquoise Lane
House · Osprey, FL 34229
MLS# A4704776 · Listing courtesy of COLDWELL BANKER REALTY
Sold$529,000Sold Sep 28, 2026
- 2 beds
- 2 baths
- 1,704 sqft
432 Shore Drive
House · Osprey, FL 34229
MLS# A4703634 · Listing courtesy of KW COASTAL LIVING III
Sold$275,000Sold Sep 24, 2026
- 2 beds
- 2 baths
- 1,316 sqft
108 Woodland Place #108
Condo · Osprey, FL 34229
MLS# A4699279 · Listing courtesy of PAT WILLIAMS REALTY, LLC
Sold$416,000Sold Sep 22, 2026
- 3 beds
- 2 baths
- 1,478 sqft
212 Washington Avenue
House · Osprey, FL 34229
MLS# O6404307 · Listing courtesy of MARK SPAIN REAL ESTATE
Sold$145,000Sold Sep 22, 2026
570 Blackburn Point Road #22
Boat slip · Osprey, FL 34229
MLS# A4704548 · Listing courtesy of BRIGHT REALTY
Homes that closed in the last month, with sold prices where the MLS reports them. Osprey (ZIP 34229). Nokomis has its own page. As of Oct 18, 2026.
Recent sales across the Sarasota area ›
Properties displayed may be listed or sold by various participants in the MLS.
What's my home worth? ›Homes sold in Osprey at a glance.
From the listings on this page, live from Stellar MLS.
- Typical size
- 2,150 sq ft
- Most common
- 3 bedrooms
- 50% of them
- Typical year built
- 2001
- Waterfront
- 19%
- Private pool
- 38%
Most listings by subdivision
- Bay Street Village 3
- Meridian at the Oaks Preserve 3
- Pine Run 3
- Oaks 2
- Park Trace Estates 2
- Rivendell Woodlands 2
Shares count only listings where the listing agent filled in that detail. Subdivision names as entered in the MLS. As of Oct 18, 2026.
More homes in Osprey.
Recently Sold Homes near Osprey.
Questions about homes sold in Osprey.
How many homes sold in Osprey in the last month?
26 homes closed in the last month as of Oct 18, 2026, from Stellar MLS. Listings update every 15 minutes; counts and prices are recalculated hourly.
What is the median sold price of homes sold in Osprey?
The median sold price is $595,000; most sold between $253,000 and $2,121,000. Sold prices are from the MLS; a few sales don't report one.
Can George help me sell in Osprey?
Yes. George Predescu, REALTOR® with Horizon Realty International, can tell you what your home could sell for based on recent sales like these. Call or text (941) 899-3045.
Why do some sales show no sold price?
A few sales don’t report the price to the MLS, so the site can’t show one. George can tell you more about a specific sale.

Selling in Osprey?
Ask George what yours is worth.
George Predescu, REALTOR® with Horizon Realty International. A free price estimate from recent sales like these.
Osprey by type
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Listings courtesy of Stellar MLS as distributed by MLS GRID
Based on information submitted to the MLS GRID as of Oct 18, 2026, 8:30 PM EDT. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. 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. Some IDX listings have been excluded from this website. Full IDX / DMCA disclaimer