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.
Pending
Price increase: $10K (3/25)
$385,000
1795 Highland Rd, Osprey, FL 34229
3beds
1,879sqft
Est.:
Single Family Residence
Built in 1999
3,332 Square Feet Lot
$372,100 Zestimate®
$205/sqft
$150/mo HOA
What's special
Air-conditioned garagePrivate kayak launchUnique two-level layoutWood flooringTray ceilingsCrown molding
- 45 days |
- 566 |
- 18 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listing Provided by:
Rachel Tritschler 941-993-5892,
RE/MAX ALLIANCE GROUP 941-954-5454,
Rick Tritschler, Jr. 941-928-1292,
RE/MAX ALLIANCE GROUP
Source: Stellar MLS,MLS#: A4684679
Originating MLS: Sarasota - Manatee
Originating MLS: Sarasota - Manatee
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Features: En Suite Bathroom, Walk-In Closet(s)
- Level: Second
- Area: 228 Square Feet
- Dimensions: 19x12
Bedroom 2
- Features: En Suite Bathroom, Built-in Closet
- Level: Second
- Area: 140 Square Feet
- Dimensions: 14x10
Bathroom 3
- Level: First
Bathroom 3
- Features: Built-in Closet
- Level: First
Balcony porch lanai
- Level: Second
- Area: 133 Square Feet
- Dimensions: 19x7
Dinette
- Level: Second
- Area: 49 Square Feet
- Dimensions: 7x7
Kitchen
- Level: First
Kitchen
- Features: Granite Counters
- Level: Second
- Area: 110 Square Feet
- Dimensions: 10x11
Living room
- Level: First
Living room
- Features: Ceiling Fan(s)
- Level: Second
- Area: 391 Square Feet
- Dimensions: 23x17
Heating
- Central, Electric
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
- Laundry: Laundry Room
Features
- 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)
- Flooring: Carpet, Ceramic Tile, Hardwood
- Doors: Outdoor Kitchen, Sliding Doors
- Windows: Window Treatments
- Basement: Other
- Has fireplace: No
Interior area
- Total structure area: 2,665
- Total interior livable area: 1,879 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Oversized, Under Building
- Attached garage spaces: 1
- Carport spaces: 1
- Covered spaces: 2
- Details: Garage Dimensions: 11x30
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered, Patio, Porch, Screened
- Exterior features: Balcony, Lighting, Outdoor Kitchen, Private Mailbox, Rain Gutters
- Fencing: Wood
Lot
- Size: 3,332 Square Feet
- Features: In County
- Residential vegetation: Mature Landscaping, Trees/Landscaped
Details
- Additional structures: Outdoor Kitchen
- Parcel number: 0156120015
- Zoning: RMF2
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Florida
- Property subtype: Single Family Residence
- Attached to another structure: Yes
Materials
- Vinyl Siding
- Foundation: Pillar/Post/Pier
- Roof: Metal
Condition
- New construction: No
- Year built: 1999
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Water Connected
Community & HOA
Community
- Features: Water Access, Pool
- Pet fee: $0 monthly
- Subdivision: TOWNS-END SHORES
HOA
- Has HOA: Yes
- Amenities included: Playground, Pool
- Services included: Community Pool, Maintenance Grounds, Maintenance Repairs, Pest Control, Pool Maintenance
- HOA fee: $150 monthly
- HOA name: Colleen Donlevy
- HOA phone: 407-325-2873
Location
- Region: Osprey
Financial & listing details
- Price per square foot: $205/sqft
- Tax assessed value: $307,900
- Annual tax amount: $2,808
- Date on market: 3/10/2026
- Cumulative days on market: 43 days
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 18000
- Electric utility on property: Yes
- Road surface type: Paved, Asphalt
Estimated market value
$372,100
$353,000 - $391,000
$3,457/mo
Price history
| Date | Event | Price |
|---|---|---|
| 4/6/2026 | Pending sale | $385,000$205/sqft |
Source:  Stellar MLS #A4684679 Report a problem | ||
| 3/25/2026 | Price change | $385,000+2.7%$205/sqft |
Source: Stellar MLS #A4684679 Report a problem | ||
| 3/10/2026 | Listed for sale | $375,000+51.2%$200/sqft |
Source: Stellar MLS #A4684679 Report a problem | ||
| 12/27/2025 | Listing removed | $1,500$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 12/12/2025 | Price change | $1,500-6.3%$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 11/28/2025 | Listed for rent | $1,600+14.3%$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 7/3/2025 | Listing removed | $1,400$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 6/21/2025 | Listed for rent | $1,400$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 4/5/2025 | Listing removed | $1,400$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 3/17/2025 | Price change | $1,400-6.7%$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 3/13/2025 | Price change | $1,500+15.4%$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 3/12/2025 | Listed for rent | $1,300$1/sqft |
Source: Zillow Rentals Report a problem | ||
| 10/12/2018 | Sold | $248,000-3.9%$132/sqft |
Source: Public Record Report a problem | ||
| 9/15/2018 | Pending sale | $258,000$137/sqft |
Source: Keller Williams Realty Select #A4408365 Report a problem | ||
| 6/17/2018 | Listed for sale | $258,000+18.9%$137/sqft |
Source: Owner Report a problem | ||
| 5/23/2016 | Sold | $217,000+65.6%$115/sqft |
Source: Public Record Report a problem | ||
| 5/23/2002 | Sold | $131,000-0.8%$70/sqft |
Source: Public Record Report a problem | ||
| 12/30/1999 | Sold | $132,000$70/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $2,809 +13.9% | $223,129 +2.9% |
| 2024 | $2,465 +4.1% | $216,841 +3% |
| 2023 | $2,369 +3% | $210,525 +3% |
| 2022 | $2,299 +0.5% | $204,393 +3% |
| 2021 | $2,288 +0% | $198,440 +1.4% |
| 2020 | $2,288 +4.3% | $195,700 +2.3% |
| 2019 | $2,194 | $191,300 +7.3% |
| 2018 | $2,194 +9.1% | $178,267 +2.1% |
| 2017 | $2,011 +492.6% | $174,600 -0.7% |
| 2016 | $339 | $175,900 +16.9% |
| 2015 | $339 | $150,500 +34.8% |
| 2014 | $339 -71.9% | $111,665 |
| 2013 | $1,207 +3.2% | $111,665 +1.7% |
| 2012 | $1,170 +5.3% | $109,798 +3% |
| 2011 | $1,111 -7.8% | $106,600 -4.4% |
| 2010 | $1,205 -45.6% | $111,500 -19.3% |
| 2009 | $2,212 | $138,100 -30.2% |
| 2008 | $2,212 -22.2% | $197,900 -16.1% |
| 2007 | $2,843 | $235,900 -5% |
| 2006 | -- | $248,400 +30.2% |
| 2005 | -- | $190,800 +10.5% |
| 2004 | $2,752 -2.8% | $172,600 +0.2% |
| 2003 | $2,831 +28.3% | $172,300 +33.8% |
| 2002 | $2,207 +12.2% | $128,800 +7.9% |
| 2001 | $1,968 +4.9% | $119,400 +7.3% |
| 2000 | $1,875 | $111,300 |
Find assessor info on the county website
Monthly payment
Est. payment
$2,419/mo
Principal & interest
$1862
Property taxes
$407
HOA Fees
$150
More affordability tools
Climate risks
Neighborhood: 34229
Nearby schools
GreatSchools rating
- 8/10Laurel Nokomis SchoolGrades: PK-8Distance: 4 mi
- 6/10Venice Senior High SchoolGrades: 9-12Distance: 5.8 mi
Schools provided by the listing agent
- Elementary: Laurel Nokomis Elementary
- Middle: Sarasota Middle
- High: Venice Senior High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Sarasota County
- Osprey
- 34229
- 1795 Highland Rd
Nearby cities
Nearby zip codes
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