1795 HIGHLAND ROAD, Osprey, FL 34229

• 3 beds |
• 3 baths |
• 1,879 sqft

Property Description

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.

Listing Status:

Active

Date Added:

March 10, 2026

Data Last Updated:

March 12, 2026 at 7:24AM

Listing Office:

RE/MAX ALLIANCE GROUP : 941-954-5454

Listing Agent:

Rachel Tritschler : 941-993-5892

MLS ID:

A4684679

Interior

• General: Ceiling Fans(s)Crown MoldingEat-in KitchenKitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanPrimaryBedroom UpstairsSolid Wood CabinetsSplit BedroomStone CountersThermostatTray Ceiling(s)Walk-In Closet(s)Window Treatments
• Appliances: DishwasherDryerMicrowaveRangeRefrigeratorWasher
• Laundry: Laundry Room
• Basement: Other
• Flooring: CarpetCeramic TileWood
• A/C: Central Air
• Heating: CentralElectric

Exterior

• General: BalconyLightingOutdoor KitchenPrivate MailboxRain GuttersSliding Doors
• Style: Florida
• Other Structures: Outdoor KitchenPorchScreenedPatioCovered
• Parking: OversizedBasement

Construction

• Roofing: Metal
• General: Vinyl SidingTwoPillar/Post/Pier

Location

• Road/Access: AsphaltPaved
• HOA Amenities: PlaygroundPoolPoolMaintenance GroundsMaintenancePest Control150.0Monthly
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: RMF2LOT 17BLK ALESS PORTION DESC AS BEG AT NW COR OF LOT 17 TH N-62-35-43-E 90.16 FT TH S-20-24-17-E 38.08 FT TH S-69-39-18-W 90.15 FT TH N-20-25-00-W 37.99 FT TO POBTOWNS-END SHORES0156120015
• Fencing: Wood

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedPublicSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple