1795 HIGHLAND ROAD Osprey, FL $ 375,000
1795 HIGHLAND ROAD
$ 375,000
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1795 HIGHLAND ROAD

Osprey, FL, 34229
$ 375,000
Bedrooms3 Baths3.0 Sq 1,879

Monthly Estimate*

$ 2,309

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Single Family Home for sale in Osprey, FL

for $375,000 with 3 bedrooms and 3 full baths. This 1,879 square foot home was built in 1999 on a lot size of 0.08.

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.

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Single Family Active

Price

$ 375,000

Bedrooms

3

Full Bath

3

Property Type

Single Family

Taxes

$ 2,808

Style

Florida

Lot Size

0.08

Year Built

1999

Town/City

Osprey

County/Region

Sarasota

MLS | Web ID

A4684679

Features
General
Sewer Public Sewer
Heating Central Electric
Cooling Central Air
Utilities BB/HS Internet Available Cable Available Electricity Connected Public Sewer Connected Water Connected
Roof Metal
Appliances Dishwasher Dryer Microwave Range Refrigerator Washer
Zoning RMF2
HOA Fee 150
Garage Spaces 1
Association Fee Includes Community Pool Maintenance Grounds Maintenance Repairs Pest Control Pool Maintenance
Patio/Porch Features Covered Patio Porch Screened
Architectural Style Florida
Construction Materials Vinyl Siding
Pets Allowed Yes
Year Built 1999
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Water Access Pool
Assoc Fee Paid Per Monthly
County Sarasota
New Construction false
Property Type Residential
Association Amenities Playground Pool
Attached Garage true
Subdivision Name TOWNS-END SHORES
Facing Direction Southwest
Garage Y/N true
Other Structures Outdoor Kitchen
Total Rooms 10
Full Baths 3
Status Active
Directions From US41 turn west onto North Lane then turn left onto Highland Road. The home will be on the left.
High School Venice Senior High
City OSPREY
Association Name Colleen Donlevy
Senior Community Y/N false
MLS Area 34229 - Osprey
Lot Size Units Square Feet
Lot Size Square Feet 3332
Carport Spaces 1
Carport Y/N true
Listing Terms Cash Conventional FHA VA Loan
Elementary School Laurel Nokomis Elementary
Property Attached Y/N true
Land Lease Y/N false
Tax Annual Amount 2808.98
Middle/Junior High School Sarasota Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/A4684679 https://poff-media-group.aryeo.com/sites/rmovxlwg/unbranded
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 17
Legal Description LOT 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
Minimum Lease No Minimum
Water Access Y/N false
Monthly HOA Amount 150
ILS Total SQFT 679
ILS Under Air SQFT 679
Water View Y/N false
Flood Zone Code X
DockY/N false
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Interior
Interior Amenities Ceiling 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
Basement Other
Flooring Carpet Ceramic Tile Hardwood
Furnished Y/N Negotiable
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 0
Laundry Features Laundry Room
Total Bedrooms 3
Total Baths 3
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Exterior
Exterior Amenities Balcony Lighting Outdoor Kitchen Private Mailbox Rain Gutters Sliding Doors
Vegetation Mature Landscaping Trees/Landscaped
Fencing Wood
Parking Features Oversized Under Building
Lot Features In County
Water Source Public
Lot Size Area 3332
Foundation Details Pillar/Post/Pier
Spa false
Building Area Total 2665
Lot Size Acres 0.08
Road Surface Type Paved Asphalt
Private Pool false
Waterfront Y/N false
Covered Spaces 2
Road Frontage Type Street Paved
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* Excluded Features
List By
Re/Max Alliance Group

Broker

Rachel@teamtritschler.com

Email

Affordability Calculator

$2,543
Per Month
91%
9%
0%
Monthly Principal & Interest
$2,309
Monthly Property Taxes
$234
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Venice Senior High High School High School
Pricing History
DatePricePrice ChangeDescription
3/10/2026$375,000 Listed Price

Map


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1795 HIGHLAND ROAD, Osprey, FL, 34229 is a Single Family Home for sale at $375,000 with 1,879 sqft and a lot size of 0.08. 1795 HIGHLAND ROAD has 3 bedrooms, 3.0 baths, and was built in 1999. The property's zip code is 34229 which is in Osprey, FL