Real Estate Investment Properties for Sale in Osprey, FL
Looking for investment property in Osprey, FL with high ROI ?
Explore a variety of short-term homes & houses in Osprey, FL. Invest wisely with VRBO & Osprey, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Woodlawn Investment Property for Sale in Osprey, FL
Search for Woodlawn Investment Property for Sale in Osprey, Florida. Browse all of Mashvisor’s Woodlawn Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.
Showing 222 Woodlawn Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
854 Macewen DrOSPREY, FLOne or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oak... |
4 beds | 4 baths | 9,081 sq.ft. |
$3,890,000 |
Airbnb cash on cash: -0.06%
|
730 Sarabay RdOSPREY, FLPremier Intracoastal Estate in Osprey 4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterf... |
4 beds | 5 baths | 6,308 sq.ft. |
$5,495,000 |
Airbnb cash on cash: -0.69%
|
1303 Thornapple DrOSPREY, FLINCREDIBLE Pool Home in INCREDIBLE Community!...You Will Be Impressed by this Well-Appoint... |
3 beds | 2 baths | 1,929 sq.ft. |
$674,900 |
Airbnb cash on cash: 1.48%
|
144 N Casey Key RdOSPREY, FLA striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless r... |
4 beds | 5 baths | 5,397 sq.ft. |
$5,495,000 |
Airbnb cash on cash: -0.84%
|
742 Harms DrOSPREY, FLATTENTION NATURE LOVERS: Your Own Private Hide-Away on one-half acre yet conveniently loca... |
3 beds | 2 baths | 1,293 sq.ft. |
$515,000 |
Airbnb cash on cash: 3.99%
|
14041 Bellagio Way #218OSPREY, FLElevate your expectations with this elegant waterfront home! This 3-bedroom, 2-bath FULLY ... |
3 beds | 2 baths | 2,374 sq.ft. |
$1,099,000 |
Airbnb cash on cash: -0.89%
|
1363 NEW FOREST LANEOSPREY, FLWelcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the... |
2 beds | 2 baths | 1,738 sq.ft. |
$499,000 |
Airbnb cash on cash: 2.19%
|
135 Tina Island DrOSPREY, FLIf you are ready to retreat to paradise, look no more. This home is amazing. Located in a ... |
3 beds | 4 baths | 2,572 sq.ft. |
$3,300,000 |
Airbnb cash on cash: -0.53%
|
403 Longbow TrlOSPREY, FLWelcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in o... |
4 beds | 3 baths | 2,770 sq.ft. |
$1,150,000 |
Airbnb cash on cash: 3.72%
|
494 MEADOW SWEET CIRCLEOSPREY, FLUnder contract-accepting backup offers. Modern farmhouse style in the Rivendell Cottages w... |
3 beds | 2 baths | 1,791 sq.ft. |
$595,000 |
Airbnb cash on cash: 2.41%
|
1801 Highland RdOSPREY, FLOne or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhom... |
2 beds | 2 baths | 1,165 sq.ft. |
$325,000 |
Airbnb cash on cash: 4.75%
|
1019 SCHERER WAYOSPREY, FLWelcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community o... |
4 beds | 3 baths | 2,498 sq.ft. |
$735,000 |
Airbnb cash on cash: 6.64%
|
764 Sarabay Rd #8OSPREY, FLWelcome to Paradise on Little Sarasota Bay! Heron Bay is an intimate, maintenance free, b... |
2 beds | 2 baths | 1,392 sq.ft. |
$450,000 |
Airbnb cash on cash: -0.94%
|
106 VILLA DRIVE #106OSPREY, FLUnder contract-accepting backup offers. Located West of the Trail in Sorrento Shores, Ospr... |
2 beds | 2 baths | 1,578 sq.ft. |
$199,000 |
Airbnb cash on cash: 6.3%
|
5100 Jessie Harbor Dr #403OSPREY, FLThis meticulously maintained, waterfront residence is in an amenity-rich, gated community.... |
2 beds | 2 baths | 2,143 sq.ft. |
$679,900 |
Airbnb cash on cash: -0.21%
|
104 Park Trace BlvdOSPREY, FLWelcome to this elegant and spacious luxury pool home offering over 2,500 square feet of r... |
4 beds | 3 baths | 2,557 sq.ft. |
$595,000 |
Airbnb cash on cash: 8.32%
|
393 N Point Rd #401OSPREY, FLThis spacious 3 bedroom, 3 bath with den has been completely updated with a new kitchen/ap... |
3 beds | 3 baths | 2,594 sq.ft. |
$835,000 |
Airbnb cash on cash: -1.65%
|
146 Willow Bend WayOSPREY, FLUnder contract-accepting backup offers. One or more photo(s) has been virtually staged. We... |
4 beds | 3 baths | 2,540 sq.ft. |
$699,000 |
Airbnb cash on cash: 7.29%
|
854 N Casey Key RdOSPREY, FLUnder contract-accepting backup offers. Nestled on the serene expanse of North Casey Key, ... |
4 beds | 4 baths | 3,462 sq.ft. |
$4,750,000 |
Airbnb cash on cash: -0.39%
|
1795 Highland RdOSPREY, FLWhether you are looking for the perfect winter home, investment property, or primary resid... |
3 beds | 3 baths | 1,879 sq.ft. |
$375,000 |
Airbnb cash on cash: 5.21%
|
392 PARK TRACE BOULEVARDOSPREY, FLUnder contract-accepting backup offers. Set on a premier lakefront lot in Osprey, 392 Park... |
4 beds | 3 baths | 2,802 sq.ft. |
$939,000 |
Airbnb cash on cash: 4.81%
|
124 Revolution WayOSPREY, FLThe only available home in the community with a 2 Car Garage! Welcome to Bay Street Villag... |
2 beds | 2 baths | 1,574 sq.ft. |
$388,000 |
Airbnb cash on cash: 2.37%
|
385 N Point Rd #304OSPREY, FL**MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF R... |
3 beds | 3 baths | 2,778 sq.ft. |
$1,200,000 |
Airbnb cash on cash: -1.71%
|
76 Osprey Point DrOSPREY, FLCOMPLETELY UPGRADED IS NOT AN EXAGGERATION! This Bo MacEwenâdesigned 3-bedroom, 4.5-bath... |
3 beds | 4 baths | 4,364 sq.ft. |
$1,650,000 |
Airbnb cash on cash: -0.5%
|
852 Macewen DrOSPREY, FL**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the hig... |
3 beds | 3 baths | 4,519 sq.ft. |
$2,495,000 |
Airbnb cash on cash: -0.48%
|
177 Navigation CirOSPREY, FL10K PRICE REDUCTION! NEED A QUICK CLOSE? NO PROBLEM, SELLERS HAVE MOVED TO THEIR NEW HOME!... |
3 beds | 2 baths | 1,581 sq.ft. |
$369,000 |
Airbnb cash on cash: 3.73%
|
49 Osprey Point DrOSPREY, FLThis 3 bedroom + office, 3.5 bath Oaks Bayside gem offers gorgeous lake views. As you ent... |
4 beds | 3 baths | 3,953 sq.ft. |
$2,500,000 |
Airbnb cash on cash: 1.02%
|
75 Osprey Point DrOSPREY, FL**STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on... |
4 beds | 4 baths | 4,001 sq.ft. |
$1,775,000 |
Airbnb cash on cash: 1.15%
|
409 N Point Rd #502OSPREY, FL**GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The cov... |
3 beds | 3 baths | 2,055 sq.ft. |
$599,000 |
Airbnb cash on cash: -1.62%
|
140 Sugar Mill DrOSPREY, FL**BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE RESIDENCE with Lush Garden Lan... |
4 beds | 4 baths | 3,286 sq.ft. |
$1,749,990 |
Airbnb cash on cash: 1.69%
|
110 Pine AveOSPREY, FLHeart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your... |
3 beds | 2 baths | 2,058 sq.ft. |
$699,000 |
Airbnb cash on cash: 2.06%
|
85 Sugar Mill DrOSPREY, FL**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Coun... |
3 beds | 3 baths | 4,191 sq.ft. |
$2,050,000 |
Airbnb cash on cash: -0.78%
|
120 Villa Dr #120OSPREY, FLMAINTENANCE-FREE & MOVE-IN READY!!! âWest of the Trailâ WATERFRONT VILLA WITH BOAT DOC... |
2 beds | 2 baths | 1,404 sq.ft. |
$515,000 |
Airbnb cash on cash: 2.04%
|
140 N Casey Key RdOSPREY, FLLIVE THE ULTIMATE COASTAL LIFESTYLE on the coveted Casey Key barrier island at this vibran... |
3 beds | 3 baths | 2,473 sq.ft. |
$1,999,999 |
Airbnb cash on cash: -0.83%
|
17 Bayhead LnOSPREY, FLImpeccable is the only way to describe this charming, completely remodeled 3-bedroom, 2-ba... |
3 beds | 2 baths | 2,850 sq.ft. |
$1,300,000 |
Airbnb cash on cash: -0.2%
|
401 N Point Rd #504OSPREY, FLFULLY UPDATED ⢠WATER VIEWS ⢠PRIVATE 2-CAR GARAGE ⢠OFFICE/4TH BEDROOM OPTION F... |
3 beds | 3 baths | 2,778 sq.ft. |
$990,000 |
Airbnb cash on cash: -1.5%
|
291 Hidden Bay Dr #102OSPREY, FLCentrally located between Sarasota and Venice, the gated community of Hidden Bay sits peac... |
2 beds | 2 baths | 1,479 sq.ft. |
$399,000 |
Airbnb cash on cash: 1.3%
|
510 Latitude LnOSPREY, FLStunning residence crafted by renowned builder Lee Wetherington. Nestled on a southern exp... |
3 beds | 2 baths | 2,298 sq.ft. |
$599,900 |
Airbnb cash on cash: 1.61%
|
401 N Point Rd #304OSPREY, FLGive yourself the gift of refined living in this expansive 2,778 square foot residenceât... |
3 beds | 3 baths | 2,778 sq.ft. |
$850,000 |
Airbnb cash on cash: -1.58%
|
6100 Jessie Harbor Dr #203OSPREY, FLLook no further! Blackburn Harbor is a boating & water sport enthusiast paradise! This b... |
3 beds | 3 baths | 2,630 sq.ft. |
$699,000 |
Airbnb cash on cash: 0.32%
|