Osprey Luxury Homes for Sale

47 luxury homes for sale in Osprey, median asking price $1,750,000, mostly $1,100,000 – $4,670,000. Homes with an asking price of $1M or more. Osprey (ZIP 34229). Nokomis has its own page. As of Oct 9, 2026.

366 CREEK COURT, OSPREY
Active

$1,049,000

366 CREEK COURT

OSPREY, FL 34229

4 bed
3 bath
2,775 sqft

MLS# A4708943 · Listing courtesy of KELLER WILLIAMS ON THE WATER S

401 N POINT ROAD #404, OSPREY
Active

$1,025,000

401 N POINT ROAD #404

OSPREY, FL 34229

3 bed
3 bath
2,778 sqft

MLS# A4708169 · Listing courtesy of COLDWELL BANKER REALTY

422 BLUE GARDEN LANE, OSPREY
Active

$1,445,000

422 BLUE GARDEN LANE

OSPREY, FL 34229

3 bed
4 bath
3,872 sqft

MLS# A4707058 · Listing courtesy of COLDWELL BANKER REALTY

401 POINT ROAD #703, OSPREY
Active

$1,200,000

401 POINT ROAD #703

OSPREY, FL 34229

3 bed
3 bath
2,203 sqft

MLS# A4707244 · Listing courtesy of GENEROUS PROPERTY

275 LOOKOUT POINT DRIVE, OSPREY
Active

$4,590,000

275 LOOKOUT POINT DRIVE

OSPREY, FL 34229

5 bed
5 bath
5,279 sqft

MLS# A4707430 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

385 NORTH POINT ROAD #701, OSPREY
Active

$1,399,000

385 NORTH POINT ROAD #701

OSPREY, FL 34229

3 bed
3 bath
2,594 sqft

MLS# A4707336 · Listing courtesy of MICHAEL SAUNDERS & COMPANY

650 OAKS CREEK COURT, OSPREY
Active

$3,700,000

650 OAKS CREEK COURT

OSPREY, FL 34229

4 bed
4 bath
4,314 sqft

MLS# A4707301 · Listing courtesy of COLDWELL BANKER REALTY

256 SUGAR MILL, OSPREY
Active

$1,399,000

256 SUGAR MILL

OSPREY, FL 34229

3 bed
3 bath
2,695 sqft

MLS# A4707187 · Listing courtesy of KIMBERLITE WEST REALTY LLC

324 OSPREY POINT DRIVE, OSPREY
Active

$3,700,000

324 OSPREY POINT DRIVE

OSPREY, FL 34229

5 bed
5 bath
6,234 sqft

MLS# A4706333 · Listing courtesy of COLDWELL BANKER REALTY

17 BAYHEAD LANE, OSPREY
Active

$1,295,000

17 BAYHEAD LANE

OSPREY, FL 34229

3 bed
2 bath
2,850 sqft

MLS# A4706711 · Listing courtesy of COLDWELL BANKER REALTY

662 FERNWALK LANE, OSPREY
Pending

$2,800,000

662 FERNWALK LANE

OSPREY, FL 34229

4 bed
4 bath
4,188 sqft

MLS# A4706319 · Listing courtesy of COLDWELL BANKER REALTY

402 MACEWEN DRIVE, OSPREY
Active

$1,590,000

402 MACEWEN DRIVE

OSPREY, FL 34229

3 bed
4 bath
3,565 sqft

MLS# A4706228 · Listing courtesy of COLDWELL BANKER REALTY

141 SUGAR MILL DRIVE, OSPREY
Active

$1,700,000

141 SUGAR MILL DRIVE

OSPREY, FL 34229

3 bed
3 bath
3,118 sqft

MLS# A4705716 · Listing courtesy of COLDWELL BANKER REALTY

362 MACEWEN DRIVE, OSPREY
Pending

$2,175,000

362 MACEWEN DRIVE

OSPREY, FL 34229

4 bed
4 bath
4,117 sqft

MLS# A4705572 · Listing courtesy of COLDWELL BANKER REALTY

1417 LANDVIEW LANE, OSPREY
Active

$1,399,000

1417 LANDVIEW LANE

OSPREY, FL 34229

4 bed
4 bath
3,255 sqft

MLS# A4705553 · Listing courtesy of PAT WILLIAMS REALTY, LLC

794 LYTHAM CIRCLE, OSPREY
Pending

$2,600,000

794 LYTHAM CIRCLE

OSPREY, FL 34229

4 bed
4 bath
4,450 sqft

MLS# A4705432 · Listing courtesy of COLDWELL BANKER REALTY

401 N POINT ROAD #903, OSPREY
Pending

$1,250,000

401 N POINT ROAD #903

OSPREY, FL 34229

3 bed
3 bath
2,203 sqft

MLS# A4705080 · Listing courtesy of COLDWELL BANKER REALTY

112 OSPREY POINT DRIVE, OSPREY
Active Under Contract

$6,449,000

112 OSPREY POINT DRIVE

OSPREY, FL 34229

6 bed
6 bath
8,621 sqft

MLS# A4702047 · Listing courtesy of DOUGLAS ELLIMAN

401 N POINT ROAD #701, OSPREY
Pending

$1,480,000

401 N POINT ROAD #701

OSPREY, FL 34229

3 bed
3 bath
2,594 sqft

MLS# A4704870 · Listing courtesy of COLDWELL BANKER REALTY

1216 CASEY KEY ROAD, OSPREY
Active

$9,750,000

1216 CASEY KEY ROAD

OSPREY, FL 34229

5 bed
8 bath
8,050 sqft

MLS# A4704643 · Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY

226 SAINT JAMES PARK, OSPREY
Active

$1,495,000

226 SAINT JAMES PARK

OSPREY, FL 34229

3 bed
3 bath
2,591 sqft

MLS# A4704489 · Listing courtesy of KELLER WILLIAMS ON THE WATER S

154 LOOKOUT POINT DRIVE, OSPREY
Active

$2,095,000

154 LOOKOUT POINT DRIVE

OSPREY, FL 34229

4 bed
4 bath
4,578 sqft

MLS# TB8543439 · Listing courtesy of FLAT FEE MLS REALTY

296 PINE RANCH TRAIL, OSPREY
Active

$1,100,000

296 PINE RANCH TRAIL

OSPREY, FL 34229

5 bed
4 bath
3,354 sqft

MLS# A4704317 · Listing courtesy of BEYOND REALTY LLC

907 EAGLE ISLE COURT, OSPREY
Active Under Contract

$1,100,000

907 EAGLE ISLE COURT

OSPREY, FL 34229

4 bed
3 bath
3,984 sqft

MLS# A4703534 · Listing courtesy of CENTURY 21 ROSEBAY

More in Osprey

Luxury Homes for Sale nearby

Questions about Osprey Luxury Homes for Sale

How many luxury homes are for sale in Osprey?

47 luxury homes are listed on this site as of Oct 9, 2026, from Stellar MLS. The list updates every hour.

What is the median asking price of luxury homes in Osprey?

The median asking price is $1,750,000; most are listed between $1,100,000 and $4,670,000. These are asking prices, not sale prices.

Can George help me buy in Osprey?

Yes. George Predescu, REALTOR® with Horizon Realty International, can set up showings for any listing here, including ones listed by other brokers. Call or text (941) 899-3045.

Want to see one of these luxury homes?

George Predescu, REALTOR® with Horizon Realty International, can answer questions and set up showings.

Call (941) 899-3045Text GeorgeSend a message

Listings courtesy of Stellar MLS as distributed by MLS GRID

Based on information submitted to the MLS GRID as of Oct 9, 2026, 3:15 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