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$385,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 1,879 Sq. Ft.
  • Updated 9 days ago
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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.

Full Property Details for 1795 Highland Rd

General

  • Price: $385,000
  • HOA FEE: $150/month
  • Taxes: $2,808 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4684679
  • Updated: 3/25/2026
  • Added to Site: 25 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 10
  • Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, Kitchen and Family Room Combination, 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
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Negotiable
  • Flooring: Carpet, Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Playground, Pool

Exterior

  • Exterior Features: Balcony, Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters, Sliding Doors
  • Deck/Patio: Covered, Patio, Porch, Screened
  • Porch/Patio/Deck: Covered, Patio, Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 1
  • Carports: Yes
  • Carport: 1
  • Carport Spaces: 1
  • Covered Spaces: 2
  • Parking Features: Oversized, Under Building

Location

  • Area: 34229 - Osprey
  • County: Sarasota
  • Development Name: 34229 - Osprey
  • Subdivision: TOWNS-END SHORES
  • Driving Directions: From US41 turn west onto North Lane then turn left onto Highland Road. The home will be on the left.
  • Direction Faces: Southwest

School Information

  • Elementary School: Laurel Nokomis Elementary
  • Middle School: Sarasota Middle
  • High School: Venice Senior High

Community

  • Community Name: 34229 - Osprey
  • Community Features: Water Access, Pool
  • Optional Amenities: Playground, Pool
  • Association: Yes
  • Assoc. Name: Colleen Donlevy
  • Assoc. Fees Include: Community Pool, Maintenance Grounds, Maintenance Repairs, Pest Control, Pool Maintenance
  • Pet Restrictions: Buyer and Buyer's agent to verify with association.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Public, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Florida
  • Architectural Style: Florida
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Other
  • Roof: Metal
  • Stories/Levels: Two
  • Square Feet: 1,879
  • Sq. Ft. Source: Public Records
  • Year Built: 1999

Additional Structures

  • Other Structures: Outdoor Kitchen

Lot Features

  • Lot Size (Acres): 0.08
  • Lot Size (Sq. Ft.): 3,332
  • Lot Size: 3332
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Wood

Financial Considerations

  • Association Fee: $150
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $2,808.98
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • 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
  • Flood Zone Info: X
  • APN: 156120015
  • Property ID: 156120015
  • Block/Lot/Section: A

Listed by Re/Max Alliance Group

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Listing agents

— 1795 Highland Rd —

  • Re/Max Alliance Group

  • Re/Max Alliance Group

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1795 Highland Rd

School District:Sarasota County School District
NameGradesDistance
Laurel Nokomis School
1900 Laurel Road East, Nokomis, FL 34275
PK-84 mi
Venice Senior High School
1 Indian Avenue, Venice, FL 34285
9-125.8 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1795 Highland Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/25/2026
Price Increased
$385,000
2.67%
MLS
3/10/2026
Listed
$375,000
51.21%
MLS
10/11/2018
Sold
$248,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1795 Highland Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,136
-13%
$223,129
3%
2024
$2,465
4%
$216,841
3%
2023
$2,369
3%
$210,525
3%
2022
$2,299
—
$204,393
3%
2021
$2,288
—
$198,440
1%
2021
$2,288
4%
$195,700
2%
2019
$2,194
9%
$191,300
7%
2018
$2,011
1%
$178,267
2%
2017
$1,998
493%
$174,600
52%
2016
$337
-1%
$115,047
1%
2015
$339
-72%
$114,247
1%
2014
$1,213
—
$113,340
2%
2013
$1,207
—
$111,665
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Re/Max Alliance Group

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1795 Highland Road, Osprey, FL 34229 (MLS# A4684679) is a Single Family property with 3 bedrooms and 3 full bathrooms. 1795 Highland Road is currently listed for $385,000 and was received on March 10, 2026. Want to learn more about 1795 Highland Road? Do you have questions about finding other Single Family real estate for sale in Osprey? You can browse all Osprey real estate or contact a Coldwell Banker agent to request more information.

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