1795 Highland Road, Osprey, FL 34229
Local realty services provided by:Better Homes and Gardens Real Estate Synergy
Listed by: rachel tritschler, rick tritschler, jr.
Office: re/max alliance group
MLS#:A4684679
Source:MFRMLS
Price summary
- Price:$385,000
- Price per sq. ft.:$144.47
- Monthly HOA dues:$150
About this home
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, NEW ROOF 2026 with 10 year warranty! 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....
Contact an agent
Home facts
- Year built:1999
- Listing ID #:A4684679
- Added:90 day(s) ago
- Updated:June 09, 2026 at 07:44 AM
Rooms and interior
- Bedrooms:3
- Total bathrooms:3
- Full bathrooms:3
- Flooring:Carpet, Ceramic Tile, Wood
- Dining Description:Eat In Kitchen, Living Room/Dining Room Combo
- Kitchen Description:Dishwasher, Eat-in Kitchen, Kitchen/Family Room Combo, Microwave, Range, Refrigerator, Solid Wood Cabinets, Stone Counters
- Bedroom Description:Primary Bedroom Upstairs, Split Bedroom, Walk-In Closet(s)
- Basement:Yes
- Basement Description:Pillar/Post/Pier
- Living area:1,879 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central, Electric
- Central air:Yes
Structure and exterior
- Roof:Metal
- Year built:1999
- Building area:1,879 sq. ft.
- Lot area:0.08 Acres
- Lot Features:Paved
- Architectural Style:Florida
- Construction Materials:Vinyl Siding
- Exterior Features:Balcony, Covered Porch/Patio, Lighting, Outdoor Kitchen, Patio, Porch, Private Mailbox, Rain Gutters, Screened
- Foundation Description:Pillar/post/pier
- Levels:2 Story
Schools
- High school:Venice Senior High
- Middle school:Sarasota Middle
- Elementary school:Laurel Nokomis Elementary
Utilities
- Water:Public, Water Connected
- Sewer:Public, Public Sewer, Sewer Connected
Finances and disclosures
- Price:$385,000
- Price per sq. ft.:$144.47
- Tax amount:$2,809 (2025)
Features and amenities
- Appliances:Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Laundry features:Dryer, Laundry Room, Washer
- Amenities:BB/HS Internet Available, Cable Available, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Playground, Pool, Primary Bedroom Upstairs, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s), Window Treatments
- Pool features:Pool, Public Pool
Parking
- Parking description:1 Car Carport, Attached Garage, Basement, Oversized
- Garage:Yes
- Garage spaces:1
- Carport spaces:1
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