One or more photo(s) has been virtually staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas.
Designed with flexibility in mind, the property features a unique two-level layout that allows you to live upstairs while renting the lower-level in-law suite, currently producing $1,500 per month on a month-to-month lease. The private suite includes its own entrance, bedroom, bathroom, kitchen, and living area, creating an ideal setup for rental income, guests, or multigenerational living.
Upstairs, the two bedroom and two bathroom primary residence offers an open and inviting layout filled with natural light. The kitchen features granite countertops, solid wood cabinetry, and a functional layout that flows easily into the living and dining areas. Crown molding, tray ceilings, wood flooring, and thoughtful design elements add character and comfort throughout the home.
Recent updates provide valuable peace of mind, including a new air conditioning system and water heater installed in 2024, while the air-conditioned garage adds versatility for storage, hobbies, or a workshop. Plus, enjoy NO FLOOD ZONE — meaning flood insurance is not required.
Outdoor living is just as appealing. Residents enjoy low HOA dues and access to the sunny community pool, along with the rare convenience of a private kayak launch, allowing you to explore nearby waterways and mangroves with ease.
The location truly sets this property apart. Bike to the beach, explore nearby Oscar Scherer State Park, or access the Legacy Trail just minutes away for miles of scenic biking and walking. You are also conveniently located near South Bay and the beautiful beaches of Casey Key, along with local dining, shopping, and coastal attractions.
Whether you are seeking a primary residence with income potential, a coastal retreat, or an investment property in a prime west-of-the-trail location, this home delivers flexibility, lifestyle, and value all in one.
Schedule your private showing today and experience the possibilities this unique property offers.
Designed with flexibility in mind, the property features a unique two-level layout that allows you to live upstairs while renting the lower-level in-law suite, currently producing $1,500 per month on a month-to-month lease. The private suite includes its own entrance, bedroom, bathroom, kitchen, and living area, creating an ideal setup for rental income, guests, or multigenerational living.
Upstairs, the two bedroom and two bathroom primary residence offers an open and inviting layout filled with natural light. The kitchen features granite countertops, solid wood cabinetry, and a functional layout that flows easily into the living and dining areas. Crown molding, tray ceilings, wood flooring, and thoughtful design elements add character and comfort throughout the home.
Recent updates provide valuable peace of mind, including a new air conditioning system and water heater installed in 2024, while the air-conditioned garage adds versatility for storage, hobbies, or a workshop. Plus, enjoy NO FLOOD ZONE — meaning flood insurance is not required.
Outdoor living is just as appealing. Residents enjoy low HOA dues and access to the sunny community pool, along with the rare convenience of a private kayak launch, allowing you to explore nearby waterways and mangroves with ease.
The location truly sets this property apart. Bike to the beach, explore nearby Oscar Scherer State Park, or access the Legacy Trail just minutes away for miles of scenic biking and walking. You are also conveniently located near South Bay and the beautiful beaches of Casey Key, along with local dining, shopping, and coastal attractions.
Whether you are seeking a primary residence with income potential, a coastal retreat, or an investment property in a prime west-of-the-trail location, this home delivers flexibility, lifestyle, and value all in one.
Schedule your private showing today and experience the possibilities this unique property offers.
Property Details
Price:
$375,000
MLS #:
A4684679
Status:
Active
Beds:
3
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
TOWNS-END SHORES
Neighborhood:
34229osprey
Listed Date:
Mar 10, 2026
Finished Sq Ft:
1,879
Total Sq Ft:
2,665
Lot Size:
3,332 sqft / 0.08 acres (approx)
Year Built:
1999
See this Listing
Schools
Elementary School:
Laurel Nokomis Elementary
Middle School:
Sarasota Middle
High School:
Venice Senior High
Interior
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile, Hardwood
Heating
Central, Electric
Laundry Features
Laundry Room
Exterior
Architectural Style
Florida
Association Amenities
Playground, Pool
Community Features
Water Access, Pool
Construction Materials
Vinyl Siding
Exterior Features
Balcony, Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors
Other Structures
Outdoor Kitchen
Parking Features
Oversized, Under Building
Roof
Metal
Financial
HOA Fee
$150
HOA Frequency
Monthly
HOA Includes
Community Pool, Maintenance Grounds, Maintenance Repairs, Pest Control, Pool Maintenance
HOA Name
Colleen Donlevy
Tax Year
2025
Taxes
$2,809
Map
Community
- Address1795 HIGHLAND ROAD OSPREY FL
- SubdivisionTOWNS-END SHORES
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN POINT MARINA VILLAGE
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- HIDDEN BAY; LAKE VISTA
- LAKE VISTA
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OSPREY EXECUTIVE PARK
- OSPREY PARK 2
- PALMER
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SORRENTO VILLAS 1
- SORRENTO VILLAS 2
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS AT OSPREY HARBOR VILLAGE
- VILLAS AT THE OSPREY HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WEBBS W D ADD
- WILLOWBEND
- WILLOWBEND PH 1
- WILLOWBEND PH 2
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WINDSOR LODGE AT THE OAKS
Market Summary
Current real estate data for Single Family in OSPREY as of Mar 20, 2026
114
Single Family Listed
125
Avg DOM
452
Avg $ / SqFt
$1,404,714
Avg List Price
Property Summary
- Located in the TOWNS-END SHORES subdivision, 1795 HIGHLAND ROAD OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $375,000 and features 3 beds, 3 baths, and has approximately 1,879 square feet of living space, and was originally constructed in 1999. The current price per square foot is $200. The average price per square foot for Single Family listings in OSPREY is $452. The average listing price for Single Family in OSPREY is $1,404,714. To schedule a showing of MLS#a4684679 at 1795 HIGHLAND ROAD in OSPREY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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Courtesy of RE/MAX ALLIANCE GROUP. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 1795 HIGHLAND ROAD
OSPREY, FL









































































