285 Bayside Dr, Clearwater, FL 33767
OFF MARKET

$2,809,000

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 3,500 sqft

285 Bayside Dr, Clearwater, FL 33767

Clearwater Beach
Est. Refi. Payment $19,172/mo*
Refinance Your Home
Currently Off Market - Sold Jan 5, 2009 for $1,600,000

Home Value

Trulia Estimate
$2.81M
Since last month
Decreased$42K (-1.5%)
Since last year
Increased$251K (+9.6%)
Since last sale
Increased$1M (+79.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +95% in the last 10 years
MonthEstimated value
2026
September 2026$2.87M
August 2026$2.88M
July 2026$2.91M
June 2026$2.74M
May 2026$2.67M
April 2026$2.64M
March 2026$2.64M
February 2026$2.6M
January 2026$2.56M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
246 BAYSIDE DRIVE, Clearwater, FL
0.09
Single-Family Home
$1,600,000
09/08/26
3
3
1,648
887 S GULFVIEW BOULEVARD, Clearwater, FL
0.25
Single-Family Home
$2,990,000
11/03/25
4
3
2,996
173 DEVON DRIVE, Clearwater, FL
0.36
Single-Family Home
$1,700,000
08/10/26
3
2
2,106
295 BAYSIDE DRIVE, Clearwater Beach, FL
0.06
Single-Family Home
$4,550,000
04/02/26
5
4.5
5,051
106 MIDWAY ISLAND, Clearwater, FL
0.72
Single-Family Home
$1,625,000
09/26/25
3
3.5
2,821
108 BAYSIDE DRIVE, Clearwater, FL
0.44
Single-Family Home
$2,900,000
07/28/26
4
4
4,022
94 DEVON DRIVE, Clearwater, FL
0.56
Single-Family Home
$1,250,000
07/23/26
3
2.5
1,982
13 WINDWARD ISLAND, Clearwater, FL
0.66
Single-Family Home
$1,500,000
01/02/26
3
2
1,667
74 WINDWARD ISLAND, Clearwater, FL
0.73
Single-Family Home
$1,300,000
10/10/25
3
2
2,563
301 MIDWAY ISLAND, Clearwater, FL
0.88
Single-Family Home
$2,199,000
04/10/26
4
3
4,176

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
290 BAYSIDE DRIVE, Clearwater, FL 33767
0.04
$3,390,000
4
3
4,519
For Sale
295 BAYSIDE DRIVE, Clearwater Beach, FL 33767
0.05
$4,550,000
5
4.5
5,051
Recently Sold
277 BAYSIDE DRIVE, Clearwater, FL 33767
0.02
$5,000,400
5
4.5
5,106
Off Market
246 BAYSIDE DRIVE, Clearwater, FL 33767
0.09
$1,600,000
3
3
1,648
Recently Sold
205 BRIGHTWATER DRIVE #202, Clearwater, FL 33767
0.17
$999,000
3
3
2,017
Foreclosure
868 BAYWAY BOULEVARD #303, Clearwater, FL 33767
0.18
$521,400
2
2
1,007
Off Market
868 BAYWAY BOULEVARD #306, Clearwater, FL 33767
0.18
$489,200
2
2
1,007
Off Market
868 BAYWAY BOULEVARD #101, Clearwater, FL 33767
0.18
$515,000
2
2
1,181
For Sale
868 BAYWAY BOULEVARD #108, Clearwater, FL 33767
0.18
$450,000
2
2
1,181
Recently Sold
868 BAYWAY BOULEVARD #206, Clearwater, FL 33767
0.18
$435,000
2
2
1,007
Recently Sold
868 BAYWAY BOULEVARD #210, Clearwater, FL 33767
0.18
$500,000
2
2
1,007
Recently Sold
868 BAYWAY BOULEVARD #307, Clearwater, FL 33767
0.18
$549,000
2
2
1,181
For Sale

Local Information

  • Map ViewExplore the area around 285 Bayside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1977
3,500 sqft
$803/sqft
Garage

About this House

This custom built waterfront home feels like a private resort with panoramic vistas of Clearwater Bay, abundant outdoor living spaces, boating amenities close to the Gulf of Mexico and indoor entertainment areas. The property is situated on a quiet Clearwater Beach cul-de-sac only minutes from the Gulf of Mexico. The deep water L-shaped lighted dock features a boat house with boat lift to accommodate a 35' boat. Double entry doors open to a foyer hall. Located on this level is a large media room/recreation room with French doors opening to the 30,000 gallon swimming pool with new Pebble Sheen finish, slide, diving board, pool sweep and auto fill feature plus a raised heated waterfall spa. An alcove bar includes custom cabinetry, granite counters and full sized refrigerator with ice maker. A guest bedroom with built-in desk adjoins the pool bath. Brick flooring continues into the billiards room which opens both to a private front yard brick courtyard and to the waterside Ultra Wood deck and canopied horseshoe shaped bar. Imagine the entertainment possibilities for outdoor and indoor living. On the second floor the great room features a natural gas fireplace, entertainment center cabinetry, vaulted wood beam ceiling, Italian ceramic tile flooring and a 30 foot cantilevered deck overlooking the water. The open dining area adjoins a remodeled kitchen offering natural maple cabinets, granite counters and backsplash, breakfast bar, Thermador five burner gas cook top, Sub Zero refrigerator, warming drawer, lighted wine rack and concealed pantry. The master bedroom, which was updated in 2006, includes a vaulted wood beam ceiling, waterfront deck, lighted closets with California Closets features and private bath with dual sink vanity, two person Jetta therapy spa tub and Italian tile shower. The second bedroom, currently used as an office, features a vaulted ceiling and private bath. Additional amenities include stained glass windows, security system, irrigation system with reclaimed water, reverse osmosis water filters, oversized two car garage with workshop area, four zones heat and air, natural gas tank-less hot water heater, central vacuum and clay brick pavers. Truly this home is an entertainment paradise.
285 Bayside Dr, Clearwater, FL 33767 is a 3 bedroom, 3 bathroom, 3,500 sqft single-family home in Clearwater Beach, built in 1977. It last sold for $1,600,000 on Jan 5, 2009. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,809,000, with a rent estimate of $6,553/month.

Home Details for 285 Bayside Dr

Interior Features

Heating & Cooling
Heating: Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile
Interior Details
AtticWet BarCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: MetalDeckExterior: Wood, Cement ConcreteFoundation Type: WoodGardenLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1977Year Updated: 1987
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 10168 sqft

Price and Tax history

DateEventPrice
Apr 21, 2011
Source: Agent Provided
ListingRemoved
$2,199,000
Apr 19, 2011
Source: Agent Provided
Listed For Sale
$2,199,000
Mar 9, 2011
Source: Agent Provided
ListingRemoved
$2,199,000
Mar 8, 2011
Source: Agent Provided
Listed For Sale
$2,199,000
Jan 5, 2009
Source: Stellar MLS #U7319074
Sold
$1,600,000

Market trends in Clearwater

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$368K
$10KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$261
$0MoM
Available listings
1417
24MoM

Around this home

Neighborhood Overview

Clearwater Beach
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Clearwater Beach

At least 30 Trulia users voted on each feature.

  • 76 % Say it's quiet

  • 76 % Say people would walk alone at night

  • 74 % Say it's dog friendly

  • 74 % Say it's walkable to restaurants

  • 73 % Say car is needed

  • 69 % Say there's holiday spirit

  • 69 % Say there are sidewalks

  • 69 % Say streets are well-lit

  • 59 % Say they plan to stay for at least 5 years

  • 50 % Say parking is easy

  • 44 % Say yards are well-kept

  • 42 % Say there are community events

  • 40 % Say it's walkable to grocery stores

  • 35 % Say kids play outside

  • 31 % Say there's wildlife

  • 30 % Say neighbors are friendly

Sourced by Trulia users. Learn more about our methodology.
  • Rafalskiedward
    "Very doggie friendly and a nice vibe…lots of new construction taking place and will continue to evolve into a really nice place to settle…"
    1
    Flag
  • Ericstillwellevans
    " bar crawls pot lucks and picnics. We also have a yearly beach picnic for the boat races which is well attended by all. The bike parade is one of the best events of the year. "
    1
    Flag
  • Trulia User
    "I'm friendly with pets however I'm gonna love playing with dogs and doing a handshake with them i do have my own pet in my country "
    0
    Flag
  • Trulia User
    "It is a very prominent tourist location we a great sense of community. I feel as thought it’s exactly the correct place to raise children. It is beautiful here through and through. "
    0
    Flag
  • Trulia User
    "Well I have a vehicle but if you didn’t there are plenty bus stops and trolly pickups around………………….😃"
    0
    Flag
  • Wac46
    "Easy commute, good roads, excellent condition for driving around nice seascape very relaxing place to get around "
    1
    Flag
  • Garyevagedes
    "It seems to be a relatively safe area, although it might be a bit boring for children. There is a playground in the central area of the island, but the northern part of the island is very quiet. As an older adult I have to say that I quite like it!"
    3
    Flag
  • Mona G.
    "We have lived in Clearwater Beach area for five plus years. It is expensive to live here, but probably the best place to live in Tampa Bay area! Pier 60 has something going almost everyday. Very safe area, can go for walks anytime of the day. Lots of good restaurants. Clearwater Beach deserves to be considered one of the best beaches in the country and likely in the world. We live on the water on Devon Drive across from the Clearwater Beach main area. Wild life is just wonderful! It is truly living like a dream. Only drawback is traffic, especially on holiday weekends or in spring break and housing is lot more expensive than inland."
    1
    Flag
  • Keith
    "We have not attended any community events other than events and activities in the beach area. They are well done. "
    0
    Flag
  • Shay H.
    "Best beach and area in FL! White sands, quiet, restaurants and the Pier are great. Good distance to amusement parks, aquariums etc. "
    5
    Flag
  • Fitgirllauramcclure
    "Holiday events and any kind of festivals that could come such as arts, music, food for all ages. It feels safe and I truly feel like I belong here"
    1
    Flag
  • Fitgirllauramcclure
    "Feels safe, nice people and very beautiful area. Would love to live here permanently. Neighbors are so friendly."
    0
    Flag
  • Carlos A.
    "Everybody walk the dogs in the daytime and in the night without a problem. The dog's beach is the very nice place to go with them."
    4
    Flag
  • Carlos A.
    "All the place. The beach close to us. The sunsets and the crazy way to reach Mandalay Ave. with the traffic."
    1
    Flag
  • Carlos A.
    "I like the dogs Beach !! Its very nice!! The big problem is the parking!! Sometimes somebody is in my parking space! "
    1
    Flag
  • Alphiesd
    "I live in Orlando Florida and all my life I have seen Tampa as a field because where I had only visited was my family that lives in the tampa fields but I never imagined that the city of tampa and clear water would love me so much and for that reason I want to start looking for a house in tampa"
    0
    Flag
  • Keyairuh
    "I like the safety of the building. You must have a key to swipe. There are restaurants and grocery stores walking distance as well as plenty of parking. "
    0
    Flag
  • JP A.
    "This is the best beach location in the whole of Tampa Bay. 15 minutes walking distance to Caladesi State Park along the beach, and 15 minutes walking to the Clearwater Beach pier walking the other. Zero traffic noise. Dolphins pelicans seagulls terns sandpipers and amazing sunsets every day. Paradise on earth."
    0
    Flag
  • bobbernoodle
    "What a fabulous home, steps to the beach, perfect for families, visitors, and retirees who love to entertain, or just a couple who want their own piece of paradise. Traffic is average getting to the island, spring break, it's heavier, but what a fabulous place to be."
    0
    Flag
  • Denis K.
    "Old Florida Gulf coast at its best. Relax with one of the world's nicest beaches and great restaurants with a welcome from everyone you meet. Watersports abound and the local deserted beaches such as Caldesi National park have no equal."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 285 Bayside Dr

  • What is 285 Bayside Dr estimated to be worth?
    Trulia's estimated value for 285 Bayside Dr in Clearwater, FL is $2,809,000.
  • What is the price history for 285 Bayside Dr?
    285 Bayside Dr in Clearwater, FL last sold for $1,600,000 in January 2009.
  • Is Clearwater a buyer's or seller's market?
    Clearwater is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Clearwater?
    The median sale price in Clearwater is $368K. That is up $10K from the prior month.
  • Does 285 Bayside Dr have air conditioning?
    Yes, 285 Bayside Dr in Clearwater, FL has air conditioning.
  • Does 285 Bayside Dr have a pool?
    Yes, 285 Bayside Dr in Clearwater, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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