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OSPREY, FL 34229 1795 HIGHLAND ROAD

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Presented By: RE/MAX ALLIANCE GROUP with 941-954-5454. - 941-954-5454
  • MLS# A4684679
  • 03/02/2026
  • Request Tour
  • Request Info
  • Beds • 3
  • Baths • 3
  • SQFT • 1,879
  • Garage • 1

Home Details

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.
Presented By: RE/MAX ALLIANCE GROUP with 941-954-5454. - 941-954-5454

Interior Features for 1795 HIGHLAND ROAD

Bedrooms

Total Bedrooms3

Bathrooms

Half Baths0
Total Baths3

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
BasementOther
Fireplace Y/NNo
FlooringCarpet, Ceramic Tile, Hardwood
Furnished Y/NNegotiable
Heating Y/NYes
Interior AmenitiesCeiling Fan(s), Crown Molding, Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s), Window Treatments
Laundry FeaturesLaundry Room
Total Stories2

General for 1795 HIGHLAND ROAD

Additional Parcels Y/NNo
AppliancesDishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Architectural StyleFlorida
Assoc Fee Paid PerMonthly
Association AmenitiesPlayground, Pool
Association Fee IncludesCommunity Pool, Maintenance Grounds, Maintenance Repairs, Pest Control, Pool Maintenance
Association NameColleen Donlevy
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Spaces1
Carport Y/NYes
CityOSPREY
Community FeaturesWater Access, Pool
Construction MaterialsVinyl Siding
CoolingCentral Air
CountySarasota
DirectionsFrom US41 turn west onto North Lane then turn left onto Highland Road. The home will be on the left.
DockY/NNo
Elementary SchoolLaurel Nokomis Elementary
Facing DirectionSouthwest
Flood Zone CodeX
Flood Zone Code XY
Full Baths3
Garage Spaces1
Garage Y/NYes
HOA Fee$150
HeatingCentral, Electric
High SchoolVenice Senior High
ILS Total SQFT679
ILS Under Air SQFT679
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionLOT 17, BLK A, LESS 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 POB, TOWNS-END SHORES
LevelsTwo
Listing TermsCash, Conventional, FHA, VA Loan
Living Area UnitsSquare Feet
Lot Size Square Feet3332
Lot Size UnitsSquare Feet
MLS Area34229 - Osprey
Middle/Junior High SchoolSarasota Middle
Minimum LeaseNo Minimum
Monthly HOA Amount150
New ConstructionNo
Occupancy TypeVacant
Other StructuresOutdoor Kitchen
OwnershipFee Simple
Patio/Porch FeaturesCovered, Patio, Porch, Screened
Pets AllowedYes
Property Attached Y/NYes
Property SubtypeSingle Family Residence
Property TypeResidential
RoofMetal
STELLAR_InLawSuiteDescrip1 Bathroom, 1 Bedroom, Attached, Kitchen, Private Entrance
STELLAR_InLawSuiteYNYes
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Subdivision NameTOWNS-END SHORES
Tax Annual Amount2808.98
Tax Lot17
Tax Year2025
Total Rooms10
UtilitiesBB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Water Connected
Virtual TourClick here
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Year Built1999
ZoningRMF2

Exterior for 1795 HIGHLAND ROAD

Building Area Total2665
Covered Spaces2
Exterior AmenitiesBalcony, Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors
FencingWood
Foundation DetailsPillar/Post/Pier
Lot FeaturesIn County
Lot Size Acres0.08
Lot Size Area3332
Parking FeaturesOversized, Under Building
Private PoolNo
Road Frontage TypeStreet Paved
Road Surface TypePaved, Asphalt
SpaNo
VegetationMature Landscaping, Trees/Landscaped
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Steven Silcock

Broker Owner
Price $385,000
MLS#A4684679
List Date 03/02/2026
Property Type Single Family
Phone 407.574.0218
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