20090 Benissimo Dr, Venice, FL 34293
Property image
Property image
OFF MARKET

$325,200

Trulia Estimate
as of Sep 13, 2026
  • 2 Beds
  • 2 Baths
  • 1,572 sqft

20090 Benissimo Dr, Venice, FL 34293

Home Highlights

Single-Family Home
1,572 sqft
$207/sqft

Local Information

  • Map ViewExplore the area around 20090 Benissimo Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

2026 AVAILABLE: MAY, JUN, JUL, AUG, SEP, OCT, NOV, DEC.
2027 AVAILABLE: JAN, FEB, MAR, APR.
BOOK AT: $4800/PER MONTH (SEASON IS DEC-APRIL, 3 MONTHS MINIMUM)
BOOK AT: $3000/PER MONTH (OFF SEASON IS MAY-NOV, 1 MONTH MINIMUM)
*PRICES MAY VARY DEPENDING ON NUMBER OF NIGHTS BOOKED*

This Gorgeous Villa is located in the desirable community of Gran Paradiso with its rich Italian flair and 5 Star Resort-style amenities. The fashionable and spacious two bedroom, two bath, plus den, offers just under 1,600 square feet of living space with plenty of options for your entertaining. The home provides all the comforts of Florida living with its designer touches and an attention to detail. The kitchen is appointed with stainless-steel appliances, stylish wood cabinets, granite counter tops and a breakfast bar for starting each day with a Cup-of-Joe. Complement your dining with every meal at the impressive dining table or to enjoy an evening of games. Just off the eating area you can open the double-doors to the den for a quiet lounge area that includes a twin trundle daybed. The master bedroom is spacious with two walk-in closets and adjoining private master bath with soaking tub, glass enclosed walk-in shower and dual basin sinks. The second bedroom is nicely situated with main bathroom outfitted with combination tub and shower. Extras include den, laundry room with a utility sink and washer & dryer, attached two car garage and sliders leading from both living room and master bedroom to oversized screened in patio and lanai. Gran Paradiso offers at no extra expense the Resort-style pool area with the on looking state-of-the-art fitness center, billiard and game room, walking trails, tennis courts, to the stylish Club house that includes a conference room and a grand library for enjoying a rainy day with a book. This is a fabulous location and Community for your Florida getaway!

Provided by Compass Property Management - Your direction to Annual and Seasonal Living!

~Included in rent: Water, Sewer, Garbage, Cable TV or Streaming Service, Wi-Fi, Landscaping, Electric.
~Paid in full under 90 Days, $145 Booking Fee, $1000 Security Deposit, $250 Clean, plus 13% Tax.
~Association: Application & Fee Required (Fee is Subject to Change).
~Criminal Background check is required ($50 each).

Disclaimer: information, regardless of source, is not guaranteed and should be verified.
20090 Benissimo Dr, Venice, FL 34293 is a 2 bedroom, 2 bathroom, 1,572 sqft single-family home. It last sold for $340,000 on May 7, 2021 (6,983% above the $4,800 asking price). More recently, it was listed as a rental in January 2026 with an asking price of $4,800 per month. That rental listing was removed on January 21, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $325,200.

Home Details for 20090 Benissimo Dr

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: Central AirHeating Fuel: Electric
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For DetailsAvailable: Jan 1st

Exterior Features

Exterior Home Features
Lawn
Pool
Pool

Community

Other
Playground

Building

Community rooms
Fitness Center

Additional Information

ClubhousePlaygroundTennis Court(s)

Comparable Sales for 20090 Benissimo Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
19993 BENISSIMO DRIVE, Venice, FL
0.08
Single-Family Home
$322,000
04/28/26
2
2
1,572 sqft
20176 TESORO DRIVE, Venice, FL
0.11
Single-Family Home
$337,000
03/03/26
2
2
1,572 sqft
20188 TESORO DRIVE, Venice, FL
0.10
Single-Family Home
$311,000
03/10/26
2
2
1,572 sqft
20218 BENISSIMO DRIVE, Venice, FL
0.11
Single-Family Home
$315,000
03/23/26
2
2
1,568 sqft
20289 BENISSIMO DRIVE, Venice, FL
0.14
Single-Family Home
$325,000
11/17/25
2
2
1,568 sqft
20272 TESORO DRIVE, Venice, FL
0.14
Single-Family Home
$307,000
01/02/26
2
2
1,572 sqft
20171 TESORO DRIVE, Venice, FL
0.14
Single-Family Home
$300,000
01/16/26
2
2
1,572 sqft
20345 Benissimo Dr, Venice, FL
0.21
Single-Family Home
$355,000
07/07/26
2
2
1,572 sqft
20337 BENISSIMO DRIVE, Venice, FL
0.20
Single-Family Home
$370,000
03/26/26
2
2
1,572 sqft
20219 TESORO DRIVE, Venice, FL
0.18
Single-Family Home
$405,000
07/27/26
2
2
1,572 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Venice

Last updated Aug 2026
Average rent
$2.82K
$71MoM
Available listings
727
View rental market trends in Venice, FL

Around this home

What Locals Say about Venice

At least 350 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 86 % Say car is needed

  • 85 % Say parking is easy

  • 76 % Say it's quiet

  • 75 % Say there's holiday spirit

  • 74 % Say people would walk alone at night

  • 68 % Say yards are well-kept

  • 63 % Say there's wildlife

  • 60 % Say they plan to stay for at least 5 years

  • 59 % Say there are sidewalks

  • 58 % Say neighbors are friendly

  • 56 % Say streets are well-lit

  • 42 % Say it's walkable to grocery stores

  • 41 % Say it's walkable to restaurants

  • 40 % Say there are community events

  • 38 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Karissad7790
    "No dog parks or fenced area within walking distance. Lots of off street walking but nothing for them to run freely."
    0
    Flag
  • Hollyhallowell
    "Great for dogs."
    0
    Flag
  • Frank DODY
    "Venice is safe and friendly for adults and children. Schools are supported through tax dollars and citizens."
    0
    Flag
  • Melissa Porter
    "There are few families in this neighborhood but the high school is very nearby. There are great parks and playgrounds and the overall quality of life here is excellent. "
    3
    Flag
  • Melissa Porter
    "I like when dog owners gather in the parks. Very community/neighborhood oriented. People are friendly and helpful. "
    1
    Flag
  • Pselvey
    "I love the physical activities that are available. I love the intercostal waterway plus the beach. Love the freedom boat club located here. Also have fun at the thrift stores in the area. The food is unique. "
    0
    Flag
  • Ann Capallo
    "Nice mix of young families and retirees. The schools are excellent. Our neighborhood has a beach accesssible by a ferry. It is also very quiet. Excellent medical facilities in the area"
    2
    Flag
  • Lwsmith22
    "The only gated neighborhood in the Island. It has beautiful landscaping and good amenities including a gym, tennis courts, pickleball and a heated pool. "
    1
    Flag
  • Hollyhallowell
    "Beautiful, friendly, safe, close to everything. We love living here. I work from home so I don’t have a commute. "
    3
    Flag
  • Jbmlegal
    "Quiet, safe, close to beaches, close to shopping. Great location for retirees, young families. House are in good size lots and neighbors are quiet and mostly respectful. "
    6
    Flag
  • George
    "Great access to downtown Wellen Park. Strong sense of community with friendly neighbors. Great weather and close to the coast."
    3
    Flag
  • Michellejackman13
    "I use a golf cart to go to many shops and do my grocery shopping. It is a great way to get around on the island. "
    2
    Flag
  • Mark Hood
    "Near a world class beach, fishing pier, south jetty, restaurants, shopping and nightlife and beautiful year round climate."
    3
    Flag
  • Trulia User
    "It’s perfect. We absolutely love living here. Every house is unique and well-maintained. Close to everything."
    0
    Flag
  • Trulia User
    "This area is incredibly safe and beautiful. There are plenty of trees, great beaches and lots of great places to eat. It is safe for bike riders and many people also participate in sports like basketball and tennis. There are many areas to fish. "
    3
    Flag
  • Trulia User
    "This is a wonderful community. While I don’t live here I own a small apartment here and have grown to feel at home here. It is safe, quiet, and charming and retains a sense of old Florida. I may yet move here in the future."
    2
    Flag
  • Trulia User
    "Wellfield sports complex is nearby. Also, shopping and major roads are nearby. Houses maintain their value. People seek this area."
    1
    Flag
  • Trulia User
    "yeah people walk their dogs every day, joggers, bicyclists. okay neighbors but that's just us, we have neighbors that completely blocked their view from us so.. heh.. "
    0
    Flag
  • Trulia User
    "Lots of great big amenities yet you get that cozy small community feel. It’s so close to beautiful beaches where breakfast brunches can be enjoyed while watching dolphins play! You can begin and end each day beautifully fulfilled here."
    2
    Flag
  • James P.
    "The EastGate neighborhood is a hidden gem. There are a number of nice, older homes on good-sized lots, with many being upgraded with every new owner or already renovated. There are also many future opportunities as you look around. It's a perfect location between historic downtown Venice on the Island, and east to I-75 and the new areas being built out there. There's a Publix a block over and Venice Avenue isn't as busy as Route 41. Even with all the growth and new development, this part of Venice remains low-key and very pleasant. The homes here are a good value for the money and worth either buying and renovating, or buying an upgraded one. One of the best areas in the city that is not on the island, and my family has been here since the early 90s."
    6
    Flag
  • Trulia User
    "So many opportunities for outdoor activities: walking, biking, boating, beach, swimming, surfing, shelling, shopping, dining, fishing, golfing, and so much more."
    0
    Flag
  • Beth S.
    "its nice lots of festivals a dog beach good shopping and lots of grocery stores a dog beach and pretty parks"
    1
    Flag
  • Trulia User
    "Trick-or-treat for Halloween is very active in this neighborhood. The neighborhood has sidewalks streetlights and community pool as well as baci ball court and horseshoes. It is only a mile and a 1/2 from the beach."
    0
    Flag
  • Katherineupton97
    "Dogs are generally friendly and dog parks and beaches are free and available to the public. Brohard Beach is especially good "
    11
    Flag
  • Shakira C.
    "It is a beautiful and quiet community by the beach. Restaurants are nice and there are different dining options. Sunsets on the beach are incredible beautiful. There is a fishing pier that is really nice."
    8
    Flag
  • Maddiecasella
    "I have lived in Venice for 4 years. I have lived in 4 States and plan on making Venice my forever home. It is safe. There is many things to do. The school system is well run. I live my community. It just feels like home."
    0
    Flag
  • Melissa M.
    "Friendly neighbors and safe neighborhood. Well worth living within a HOA, very well kept landscape. Close to amazing beaches! "
    10
    Flag
  • Amy R.
    "It’s ok I just think Gran Paradiso is a poor community that thinks too highly of themselves.. they’re not to keen on having renters in their properties. "
    9
    Flag
  • Jpvets
    "Not close to any public transportation. Far away from stores and grocery shopping where I live. Traffic during season is bad and takes twice as long to get anywhere than during the summer"
    8
    Flag
  • Dlremo12
    "I have no commute as I am retired. Before I commuted between 5 minutes to one and a half hours depending on when I worked on the island, Sarasota and StPete/Tampa. This is a great place to live with good roads to other communities. "
    1
    Flag
  • Juliette G.
    "Public transportation within walking distance and short commute to downtown Venice, Sarasota, Englewood and North Port"
    0
    Flag
  • Esteladavis
    "The commute to downtown is about 15 minutes and also it’s close by the beach. It’s a safe city and near Sarasota "
    1
    Flag
  • Dlremo12
    "There is a Dog park close by and it is on the beach. People enjoy walking the dogs in town and at the many fairs and fiestas as well as the farmers market. "
    6
    Flag
  • Dlremo12
    "Many people have dogs and walk them on leash. A mile away there is a beach dog park people love. There are some side wound some areas without. "
    0
    Flag
  • Idy F.
    "There is a dog beach/park where people and pets mingle. I've never seen anyone walking a dog outside of that area without a leash. Pets and pet owners appear to be happy.. as are the non pet owners who get to pet the dogs and talk to their owners. "
    0
    Flag
  • Ccvanriper
    "Music in the park every Friday night! Community events to attend most weekends, loved the bike Glow Ride!"
    0
    Flag
  • Dr. M.
    "There are a lot of dog parks, and public walkways, but most importantly... there’s a dog park on the beach! "
    0
    Flag
  • Ccvanriper
    "Neighbors help each other out. We look out for each other and watch to see if there is anything out if the ordinary. "
    0
    Flag
  • Jill M.
    "it's a safe neighborhood theirs bus routes here there's park's and good schools for the children. everybody seems very friendly and are willing to lend a helping hand without anything in return"
    0
    Flag
  • Pressley S.
    "Community events and potluck and newsletters Still new to the area and learning of events and all that is offered Nice yard maintenance. Quiet and calm area for neighborhood "
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Jan 21, 2026
Source: Zillow Rentals
ListingRemoved
$4,800
Jan 7, 2026
Source: Zillow Rentals
Listed For Rent
$4,800
Dec 3, 2025
Source: Zillow Rentals
ListingRemoved
$4,800
Oct 21, 2025
Source: Zillow Rentals
PriceChange
$4,800
Price increased by 60%
Feb 21, 2025
Source: Zillow Rentals
PriceChange
$3,000
Price decreased by 38%

Frequently asked questions about 20090 Benissimo Dr

  • What is 20090 Benissimo Dr estimated to be worth?
    Trulia's estimated value for 20090 Benissimo Dr in Venice, FL is $325,200.
  • What is the price history for 20090 Benissimo Dr?
    20090 Benissimo Dr in Venice, FL last sold for $340,000 in May 2021.
  • Is Venice a buyer's or seller's market?
    Venice is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Venice?
    The median sale price in Venice is $366K. That is down $1.33K from the prior month.
  • Does 20090 Benissimo Dr have air conditioning?
    Yes, 20090 Benissimo Dr in Venice, FL has air conditioning.
  • Does 20090 Benissimo Dr have a pool?
    Yes, 20090 Benissimo Dr in Venice, FL has a pool.

Homes for rent near 20090 Benissimo Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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