$385,000
Off-Market Date: 04/03/20261795 Highland Road Osprey, FL 34229
Pending MLS# A4684679
3 beds 3 baths 1,879 sq ft Single Family
Details for 1795 Highland Road
MLS# A4684679
Description for 1795 Highland Road, Osprey, FL, 34229
Under contract-accepting backup offers. 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, 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.
Listing Information
Property Type: Residential, Single Family Residence
Status: Pending
Bedrooms: 3
Bathrooms: 3
Lot Size: 0.08 Acres
Square Feet: 1,879 sq ft
Year Built: 1999
Garage: Yes
Stories: 2 Story
Construction: Vinyl Siding
Property Attached: Yes
Subdivision: Towns-End Shores
Foundation: Pillar/Post/Pier
County: Sarasota
School Information
Elementary: Laurel Nokomis Elementary
Middle: Sarasota Middle
High: Venice Senior High
Room Information
Main Floor
Living Room:
Kitchen:
Bathroom 3:
Bathroom 3:
Upper Floor
Primary Bedroom: 12x19
Porch: 7x19
Dinette: 7x7
Living Room: 17x23
Kitchen: 11x10
Bedroom 2: 10x14
Bathrooms
Full Baths: 3
Additonal Room Information
Laundry: Laundry Room
Interior Features
Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Flooring: Carpet,Ceramic Tile,Wood
Basement: Other
Doors/Windows: Window Treatments
Additional Interior Features: Ceiling Fan(s), Eat-In Kitchen, Window Treatments, Split Bedrooms, Walk-In Closet(s), Stone Counters, Wood Cabinets, Open Floorplan, Upper Level Primary, Crown Molding, Kitchen/Family Room Combo, Living/Dining Room, Tray Ceiling(s), Built-in Features
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Cable Available,Electricity Connected,High Speed Internet Available,Municipal Utilities,Sewer Connected,Water Connected
Cooling: Central Air, Ceiling Fan(s)
Heating: Electric, Central
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 1
Parking Description: Covered, Oversized
Roof: Metal
Pool: Association, Community
Fencing: Wood
Additional Exterior/Lot Features: Rain Gutters, Outdoor Kitchen, Lighting, Balcony, Balcony, Covered, Patio, Porch, Screened, Landscaped, Outside City Limits
Out Buildings: Outdoor Kitchen
Community Features
Community Features: Water Access, Pool
Association Amenities: Pool, Playground
HOA Dues Include: Maintenance Structure, Pool(s), Maintenance Grounds, Pest Control
Homeowners Association: Yes
HOA Dues: $150 / Monthly
Driving Directions
From US41 turn west onto North Lane then turn left onto Highland Road. The home will be on the left.
Financial Considerations
Terms: Cash,Conventional,FHA,VA Loan
Tax/Property ID: 0156120015
Tax Amount: 2808.98
Tax Year: 2025
A broker reciprocity listing courtesy: RE/MAX ALLIANCE GROUP
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Copyright 2026 Stellar MLS as distributed by the MLS GRID. All Rights Reserved.
Sales History & Tax Summary for 1795 Highland Road
Sales History
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Tax Summary
| Tax Year | Estimated Market Value | Total Tax |
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 1795 Highland Road
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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