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Lasbury Tracy Realty Inc

Biggest price cuts in Osprey, FL

Every listing here has dropped its asking price, sorted by how far it fell. A deep cut is the clearest signal a seller sends: the market said no at the old number, and they listened. These update automatically as new cuts land in the MLS feed. This page is Osprey only — the coast-wide list lives at /deals/biggest-price-cuts.

47 match right now — showing the first 30, largest percentage cut first. Updated with every feed sync.

51 Macewen Dr #5
Active
$235,000
176 days
1 bd · 1 ba · 595 sqft
51 Macewen Dr #5, Osprey, FL 34229
Flood X · Fees $1,275/mo · Built 1990

Listing courtesy of 342 REAL ESTATE · MLS# A4689838

210 Patterson Ave
Active
$950,000
40 days
3 bd · 2 ba · 2,084 sqft
210 Patterson Ave, Osprey, FL 34229
Flood X · Built 1950

Listing courtesy of REALTY ONE GROUP MVP · MLS# A4704911

3621 N Point Rd #301
Active
$525,000
251 days
3 bd · 3 ba · 2,680 sqft
3621 N Point Rd #301, Osprey, FL 34229
Flood X · Fees $1,845/mo · Built 2006

Listing courtesy of COLDWELL BANKER REALTY · MLS# A4681290

18 N Casey Key Rd
Active
$1,750,000
248 days
3 bd · 2 ba · 1,977 sqft
18 N Casey Key Rd, Osprey, FL 34229
Flood AE · Built 1973

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY · MLS# A4669083

313 Lookout Point Dr
Active
$5,299,999
189 days
4 bd · 5 ba · 5,337 sqft
313 Lookout Point Dr, Osprey, FL 34229
Flood AE, X · Fees $219/mo · Built 2016

Listing courtesy of MICHAEL SAUNDERS & COMPANY · MLS# A4688995

409 North Point Rd #401
Active
$560,000
175 days
3 bd · 3 ba · 2,594 sqft
409 North Point Rd #401, Osprey, FL 34229
Flood X · Fees $2,367/mo · Built 2004

Listing courtesy of COLDWELL BANKER REALTY · MLS# A4690812

570 Blackburn Point Rd #23
Active
$89,000
111 days
Dock-Rackominium
570 Blackburn Point Rd #23, Osprey, FL 34229
Flood AE · Fees $418/mo · Built 2006

Listing courtesy of MICHAEL SAUNDERS & COMPANY · MLS# A4697977

14021 Bellagio Way #404
Active
$999,900
169 days
3 bd · 3 ba · 2,187 sqft
14021 Bellagio Way #404, Osprey, FL 34229
Flood AE · Fees $1,577/mo · Built 2006

Listing courtesy of PREMIER SOTHEBYS INTL REALTY · MLS# N6144070

385 N Point Rd #304
Active
$1,100,000
270 days
3 bd · 3 ba · 2,778 sqft
385 N Point Rd #304, Osprey, FL 34229
Flood AE · Fees $2,515/mo · Built 2000

Listing courtesy of GENEROUS PROPERTY · MLS# A4678422

2099 S Tamiami Trl
Active
$1,250,000
274 days
2.51 acre lot
2099 S Tamiami Trl, Osprey, FL 34229
Flood X500

Listing courtesy of COLDWELL BANKER REALTY · MLS# A4677875

21 Bayhead Ln
Active
$789,000
393 days
3 bd · 2 ba · 2,246 sqft
21 Bayhead Ln, Osprey, FL 34229
Flood X · Fees $858/mo · Built 2002

Listing courtesy of COLDWELL BANKER REALTY · MLS# A4664085

110 Pine Ave
Active
$649,000
556 days
3 bd · 2 ba · 2,058 sqft
110 Pine Ave, Osprey, FL 34229
Flood X · Built 1977

Listing courtesy of BRIGHT REALTY · MLS# A4646339

570 Blackburn Point Rd #11
Active
$39,500
456 days
1.04 acre lot
570 Blackburn Point Rd #11, Osprey, FL 34229
Flood AE · Fees $362/mo · Built 2006

Listing courtesy of MICHAEL SAUNDERS & COMPANY · MLS# A4658755

236 Saint James Park
Active
$2,700,000
565 days
6 bd · 7 ba · 6,246 sqft
236 Saint James Park, Osprey, FL 34229
Flood X /AE · Fees $283/mo · Built 1986

Listing courtesy of MICHAEL SAUNDERS & COMPANY · MLS# A4644125

385 N Point Rd #402
Active
$615,000
626 days
3 bd · 3 ba · 2,055 sqft
385 N Point Rd #402, Osprey, FL 34229
Flood X, AE · Fees $2,515/mo · Built 2000

Listing courtesy of GENEROUS PROPERTY · MLS# A4635708

103 Bishops Court Rd
Active
↓ $50,000
$699,000
144 days
3 bd · 2 ba · 2,034 sqft
103 Bishops Court Rd, Osprey, FL 34229
Flood X · Fees $825/mo · Built 2000

Listing courtesy of GENEROUS PROPERTY · MLS# A4694468

6100 Jessie Harbor Dr #202
Active
$798,000
163 days
3 bd · 4 ba · 3,771 sqft
6100 Jessie Harbor Dr #202, Osprey, FL 34229
Flood AE · Fees $1,101/mo · Built 2005

Listing courtesy of CORCORAN DWELLINGS REALTY · MLS# A4690969

909 Macewen Dr
Active
$1,595,000
760 days
3 bd · 4 ba · 4,241 sqft
909 Macewen Dr, Osprey, FL 34229
Flood X · Fees $133/mo · Built 1991

Listing courtesy of GENEROUS PROPERTY · MLS# A4621683

121 N Casey Key Rd
Active
$6,100,000
374 days
4 bd · 6 ba · 4,096 sqft
121 N Casey Key Rd, Osprey, FL 34229
Flood AE · Fees $33/mo · Built 1969

Listing courtesy of DOUGLAS ELLIMAN · MLS# A4667263

1527 Buoy Ln
Active
$1,100,000
183 days
3 bd · 3 ba · 2,830 sqft
1527 Buoy Ln, Osprey, FL 34229
Flood X · Fees $204/mo · Built 1989

Listing courtesy of BRIGHT REALTY · MLS# A4688266

320 Tropic Dr
Active
$185,000
155 days
2 bd · 2 ba · 1,199 sqft
320 Tropic Dr, Osprey, FL 34229
Flood X · Fees $430/mo · Built 1980

Listing courtesy of RE/MAX PALM · MLS# A4692490

154 Lookout Point Dr
Active
$2,095,000
46 days
4 bd · 4 ba · 4,578 sqft
154 Lookout Point Dr, Osprey, FL 34229
Flood X500 · Fees $219/mo · Built 1979

Listing courtesy of FLAT FEE MLS REALTY · MLS# TB8543439

348 Tropic Dr
Active
$104,900
334 days
2 bd · 2 ba · 864 sqft
348 Tropic Dr, Osprey, FL 34229
Flood X · Fees $215/mo · Built 1977

Listing courtesy of FINE PROPERTIES · MLS# A4668240

206 Four Knot Ln
Active
$1,690,000
111 days
3 bd · 2 ba · 2,411 sqft
206 Four Knot Ln, Osprey, FL 34229
Flood X500 · Fees $219/mo · Built 1991

Listing courtesy of REALTY ONE GROUP MVP · MLS# A4695429

49 Osprey Point Dr
Active
$2,399,000
334 days
4 bd · 4 ba · 3,953 sqft
49 Osprey Point Dr, Osprey, FL 34229
Flood X · Fees $475/mo · Built 1989

Listing courtesy of MICHAEL SAUNDERS & COMPANY · MLS# A4671762

852 Macewen Dr
Active
$2,395,000
450 days
3 bd · 4 ba · 4,519 sqft
852 Macewen Dr, Osprey, FL 34229
Flood AE, X · Fees $133/mo · Built 1992

Listing courtesy of GENEROUS PROPERTY · MLS# A4659276

409 N Point Rd #502
Active
$575,000
761 days
3 bd · 3 ba · 2,055 sqft
409 N Point Rd #502, Osprey, FL 34229
Flood X · Fees $2,233/mo · Built 2004

Listing courtesy of GENEROUS PROPERTY · MLS# A4621353

280 Hidden Bay Dr #302
Active
$719,000
155 days
3 bd · 2 ba · 1,937 sqft
280 Hidden Bay Dr #302, Osprey, FL 34229
Flood AE · Fees $1,500/mo · Built 2024
New construction

Listing courtesy of BERKSHIRE HATHAWAY HOMESERVICE · MLS# A4690813

109 Woodland Pl
Active
$244,900
27 days
2 bd · 2 ba · 1,223 sqft
109 Woodland Pl, Osprey, FL 34229
Flood X · Fees $820/mo · Built 1979

Listing courtesy of PREFERRED SHORE LLC · MLS# A4705745

293 Turquoise Ln
Active
$875,000
641 days
3 bd · 2 ba · 2,271 sqft
293 Turquoise Ln, Osprey, FL 34229
Flood X · Fees $895/mo · Built 2001

Listing courtesy of GENEROUS PROPERTY · MLS# A4633961

Listing information is provided in part by Stellar MLS, as distributed by MLS GRID. Based on information submitted to the MLS as of Oct 13, 2026, 6:14 PM (ET). All data is obtained from various sources and may not have been verified by broker or MLS. All information provided is deemed reliable but is not guaranteed and should be independently verified. 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.

Lasbury Tracy Realty Inc. · [email protected]