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You are here: Home / 1795 HIGHLAND ROAD, OSPREY, FL, 34229

1795 HIGHLAND ROAD, OSPREY, FL, 34229

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$375,000
4 Days On Site

1795 HIGHLAND ROAD
OSPREY, FL 34229

For Sale|Single Family Residence|Active
3
Beds
3
Total Baths
3
Full Baths
1,879
SqFt
$200
/SqFt
1999
Built
Subdivision:
TOWNS-END SHORES
County:
Sarasota
Call Now: 941-421-7375
Is this the listing for you? We can help make it yours.
941-421-7375
1795 HIGHLAND ROAD1795 HIGHLAND ROAD1795 HIGHLAND ROAD1795 HIGHLAND ROAD
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Monthly Payment (Est.)

$1,711
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.
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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, 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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Listing Snapshot
Price 
$375,000
Days On Site 
4 Days
Bedrooms 
3
Inside Area (SqFt) 
1,879 sqft
Total Baths 
3
Full Baths 
3
Partial Baths 
N/A
Lot Size 
0.08 Acres
Year Built 
1999
MLS® Number 
A4684679
Status 
Active
Property Tax 
$2,808.98
HOA/Condo/Coop Fees 
$150 monthly
Sq Ft Source 
Public Records
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What's This?
Private
Recent Activity
4 days agoListing updated with changes from the MLS®
5 days agoListing first seen on site
General Features
Acres 
0.08
Attached Garage 
Yes
Carport 
1
Direction Faces 
Southwest
Foundation 
Pillar/Post/Pier
Garage 
Yes
Garage Spaces 
1
Levels 
Two
Number Of Stories 
2
Parking 
OversizedBasementAttached
Pets 
Yes
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
2665
Style 
Florida
Utilities 
Cable AvailableElectricity ConnectedSewer ConnectedWater Connected
Water Source 
Public
Zoning 
RMF2
Interior Features
Appliances 
DishwasherDryerMicrowaveRangeRefrigeratorWasher
Basement 
Other
Cooling 
Central Air
Flooring 
CarpetCeramic TileWood
Furnished 
Negotiable
Heating 
CentralElectric
Interior 
Crown MoldingEat-in KitchenOpen FloorplanStone CountersTray Ceiling(s)Walk-In Closet(s)
Laundry Features 
Laundry Room
Balcony/Porch/Lanai 
Dimensions - 19x7Level - Second
Bathroom 3 
Level - First
Bedroom 2 
Dimensions - 14x10Level - Second
Dinette 
Dimensions - 7x7Level - Second
Kitchen 
Dimensions - 10x11Level - SecondFeatures - Granite Counters
Living Room 
Level - First
Master Bedroom 
Dimensions - 19x12Level - Second
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Exterior Features
Construction Details 
Vinyl Siding
Exterior 
BalconyLightingOutdoor KitchenRain Gutters
Fencing 
Wood
Lot Features 
Paved
Other Structures 
Outdoor Kitchen
Patio And Porch 
CoveredPatioPorchScreened
Roof 
Metal
Community Features
Association Amenities 
PlaygroundPool
Association Dues 
150
Community Features 
Pool
Financing Terms Available 
CashConventionalFHAVA Loan
HOA Fee Frequency 
Monthly
MLS Area 
34229 - Osprey
Roads 
AsphaltPaved
Township 
38
Schools
School District
Unknown
Elementary School
Laurel Nokomis Elementary
Middle School
Sarasota Middle
High School
Venice Senior High
Listing courtesy of RE/MAX ALLIANCE GROUP (941) 993-5892



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-03-15 10:44 AM EDT

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
Powered by Showcase IDX, a Constellation1 Company
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The Wendy Lynn Group Sarasota exp Realty

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The Wendy Lynn Group Sarasota exp Realty

  • 1300 Main Street, Sarasota, FL 34236
  • 941-421-7375
  • info@sunnysarasotahomes.com

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Wendy Lynn on X

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
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Bradenton offers Homes for Sale & Condos in a Premier City

Bradenton offers Homes for Sale & Condos in a Premier City. Beaches, sports, boating, fishing & high quality of ...

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New construction in Parrish and Lakewood Ranch continues expanding rapidly.,#NewConstruction #Parrish,

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"Days on market have increased slightly, giving buyers more breathing room in certain communities.",#MarketUpdate,https://www.wendylynngroup.com/market-report.php

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
10 Mar 2031343083548266728

Privacy and security remain top priorities for many relocating buyers.,#GatedCommunities,

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Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
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Strategic pricing in week one often determines final sale price. Know where your home stands.,#HomeSelling #PricingStrategy,https://www.wendylynngroup.com/seller/valuation/

Wendy_Realtor avatar Wendy Lynn @Wendy_Realtor ·
6 Mar 2029908636147843408

"From Downtown to Palmer Ranch, Sarasota offers diverse living options from urban condos to established communities.",#SarasotaLiving,

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Sarasota is a True Paradise with Spectacular Homes & Condos for Sale. Beachfront, historic, luxury & country club estates & properties available.

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