533 Chicago Ave, Dunedin, FL 34698
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Property image
OFF MARKET

533 Chicago Ave
Dunedin, FL 34698

  • 2 Beds
  • 2 Baths
  • 1,550 sqft

$741,300

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $4,860/mo*
Refinance Your Home

$741,300

Trulia Estimate
as of Jul 7, 2026
Est. Refi. Payment $4,860/mo*
Refinance Your Home
2 Beds
2 Baths
1,550 sqft

Local Information

  • Map ViewExplore the area around 533 Chicago Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Welcome Home to Furnished Comfort!

This charming, fully furnished 2-bedroom, 2-bathroom residence offers 1,550 sq. ft. of living space for $3,300/month. Nestled in vibrant Dunedin, enjoy the convenience of easy access to local attractions, parks, and dining.

Key Features:

Spacious 2-bedroom layout
Application Fee: $75.00 | Security Deposit: $3,300/annual lease including landscaping
Pet-Friendly
Resident Benefit Package Includes:

Web App and Payment Portal
24/7 Maintenance Support, Credit Reporting and more
Obligo: Move in without a traditional security deposit!
Schedule your tour today!
533 Chicago Ave, Dunedin, FL 34698 is a 2 bedroom, 2 bathroom, 1,550 sqft single-family home. It last sold for $675,000 on Aug 15, 2022 (21,674% above the $3,100 asking price). More recently, it was listed as a rental in June 2025 with an asking price of $3,300 per month. That rental listing was removed on July 8, 2025. It is currently off market. The Trulia Estimate is $741,300, with a rent estimate of $3,909/month.

Home Highlights

Parking
No Info
Outdoor
No Info
View
No Info
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 533 Chicago Ave

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For DetailsAvailable: now

Price History for 533 Chicago Ave

DatePriceEventSource
07/08/2025$3,100ListingRemovedZillow Rentals
06/24/2025$3,100PriceChange
Zillow Rentals
06/10/2025$3,300Listed For RentZillow Rentals
04/29/2025$3,300ListingRemovedZillow Rentals
04/24/2025$3,300PriceChange
Zillow Rentals
04/14/2025$3,650Listed For RentZillow Rentals
03/31/2025$3,650ListingRemovedZillow Rentals
03/29/2025$3,650Listed For RentZillow Rentals
11/22/2024$3,650ListingRemovedZillow Rentals
11/16/2024$3,650PriceChange
Zillow Rentals
10/30/2024$3,900Listed For RentZillow Rentals
08/15/2022$675,000Sold
N/A
07/26/2022$599,800PendingStellar MLS #U8170924
07/22/2022$599,800Listed For SaleStellar MLS #U8170924
03/24/2016$362,000Sold
Stellar MLS #T2797298
02/22/2016$384,000PendingAgent Provided
02/17/2016$384,000PriceChange
Agent Provided
01/22/2016$399,000Listed For SaleAgent Provided
10/13/2003$195,000Sold
N/A

Market trends in Dunedin

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$399K
$28.33KMoM
Sale-to-List Price
96.8%
0.2%MoM
Price per sq ft
$293
$6MoM
Available listings
353
29MoM
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Property Tax and Assessment

Year2024
Tax$11,015
Assessment$659,724
Home facts updated by county records

Comparable Sales for 533 Chicago Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
554 Louden Ave, Dunedin, FL
0.10
Single-Family Home
$614,000
01/30/26
2
2
1,806
412 Beltrees St, Dunedin, FL
0.18
Single-Family Home
$597,500
12/08/25
2
2
1,688
525 Broadway, Dunedin, FL
0.15
Single-Family Home
$650,000
10/13/25
2
2
1,138
522 James St, Dunedin, FL
0.12
Single-Family Home
$503,000
07/08/25
2
1.5
1,129
266 Lyndhurst St, Dunedin, FL
0.20
Single-Family Home
$850,000
02/19/26
2
2
2,104
620 Jacaranda St, Dunedin, FL
0.22
Single-Family Home
$551,000
06/12/26
3
2
1,474
501 Louden Ave, Dunedin, FL
0.14
Single-Family Home
$450,000
12/22/25
3
2
1,358
612 Magnolia St, Dunedin, FL
0.21
Single-Family Home
$501,000
10/23/25
3
2
1,445
540 Milwaukee Ave, Dunedin, FL
0.16
Single-Family Home
$385,000
12/01/25
2
2
1,044
474 Glencairn Cir, Dunedin, FL
0.14
Single-Family Home
$773,000
11/07/25
3
2.5
1,472

Nearby homes

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Assigned Schools

These are the assigned schools for 533 Chicago Ave.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Dunedin

At least 372 Trulia users voted on each feature.

  • 94 % Say it's dog friendly

  • 79 % Say people would walk alone at night

  • 78 % Say car is needed

  • 78 % Say parking is easy

  • 76 % Say there's holiday spirit

  • 75 % Say there are sidewalks

  • 72 % Say yards are well-kept

  • 71 % Say it's walkable to restaurants

  • 71 % Say streets are well-lit

  • 70 % Say it's quiet

  • 59 % Say it's walkable to grocery stores

  • 59 % Say neighbors are friendly

  • 58 % Say they plan to stay for at least 5 years

  • 58 % Say kids play outside

  • 50 % Say there's wildlife

  • 35 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Travis Stangroom
    "Very walkable and dog friendly restaurants/pubs that you can travel to and from within a short enough distance "
    0
    Flag
  • Mckenzie
    "Dunedin is the best place to live besides San Diego CA. I’ve lived here since 1996. It has everything you’d ever want to do here and it’s so close. Most places is walkable. Dog friendly. Its nick name is Dogedin. "
    2
    Flag
  • Mckenzie
    "I’ve lived in this part of Dunedin a few blocks from the water for 20 years. I love this area and all of Dunedin. It’s so close to everything. Walking distance to the famous most walkable downtown which is waterfront "
    2
    Flag
  • Wizzie1
    "Great neighbors in Dunedin. Be sure you choose a neighborhood with families in the same stages of life. "
    0
    Flag
  • Mckenzie
    "We have Mardi Paws A great water front and walkable downtown. Everything is you need and want is within walking distance or just a couple of miles. "
    0
    Flag
  • Patricia Walters
    "Public schools are awful. Neighborhood is overpopulated. Water front areas smell like sewage for the past 10 years. "
    0
    Flag
  • Nicki Wiberg
    "careful with days and times, might get stuck in traffic of beach goers. a couple years ago it never got this bad but some days are just rough headed towards the water. "
    0
    Flag
  • Primejohng
    "Short commute to work. Excellent major hwy access is close. Tampa, Clearwater, Largo, St. Petersburg"
    2
    Flag
  • Christine Perkins
    "I’ve lived in this neighborhood for the past 35 years and have no interest in ever leaving here! Great neighbors who look after each other and are always willing to lend a hand !"
    1
    Flag
  • Sandra Gridley
    "Dogs are always welcomed here provided they are leashed and are friendly! Otherwise please keep them in your fenced back yard."
    1
    Flag
  • Trulia User
    "dog park nice pools and hot tub, good neighbors reasonable parking, reasonable rates.... also having quick responsive maintenance "
    1
    Flag
  • Elizabethheitmann
    "Dunedin is a very friendly town with a laid back small town vibe. Plenty to do in the area including an amazing outdoor lifestyle w biking, walking, golf, tennis, kayaking and so much more. It is also a thriving arts community. No pretentiousness here, only friendly kind people. "
    1
    Flag
  • Willdi79
    "What make this neighborhood unique is an old town with old structures and too many trees not my taste but lots of people like it. I like modern and less tree looks cleaner..."
    1
    Flag
  • Willdi79
    "Feels like a forest too many trees mostly old houses is like an old town. Too many mosquitoes and bugs I guess because all the trees maybe. "
    32
    Flag
  • Jennifer B.
    "Good schools if you live on the north side of Dunedin. South side school are just ok. Palm harbor schools are best in the county"
    2
    Flag
  • Tom K.
    "Not many children in my immediate area. The Catholic school is nearby and a number of children walking or biking is noticeable. Many walkers, dog walkers, bicyclers pass by. The corner at my house has a crossing guard as do many other nearby corners."
    8
    Flag
  • Jim P.
    "Larger yards. Very quiet and very safe. Good mix of retirees and families. Not a lot of turnover. Very stable. "
    7
    Flag
  • Tomkettle
    "The Pinellas Trail runs through Dunedin, it is 3 blocks from my house. I walk my dog on it every day and stop at several of the dog friendly establishments along the way and in town. Everybody likes the dogs and many will stop for a short chitchat about the dogs. My last dog is actually immortalized in Dunedin by having her portrait painted on two walls in town. Always feel welcome with my dog and am able to share him with anybody who wishes to pet him, which is often."
    13
    Flag
  • Jbs75
    "My commute is very light, not much traffic at all. I have 11 miles from home to work and it takes me about 13-15 min. "
    2
    Flag
  • Lindy B.
    "It's called DOGedin for a reason! they're allowed practically everywhere. Very dog friendly! Bars especially welcome them."
    8
    Flag
  • Joni W.
    "I've lived here for a year,the neighbors are all friendly and helpful to one another..stores restaurants and entertainment are all walking distance within my location the Marina and water is seconds away! this is the best neighborhood in Dunedin in my opinion, I would reccomend Buying in the area!"
    3
    Flag
  • Tomkettle
    "Christmas Parade; Farmer’s Marker; Craft Show; Highlander Games; Wine Festival; Craft Beers; Saint Patrick’s Day "
    8
    Flag
  • Tonya F.
    "I’ve been living here for 4 years & I love it! Great community, lots to do, people are friendly & I feel very safe here "
    0
    Flag
  • Tonya F.
    "This is a very family oriented community with amazing community spirit. There is always something to do & participate in. The downtown area is like nine other in Tampa Bay. "
    1
    Flag
  • Iam P.
    "Many Sheriffs throughout community. Feels safe. They also do routine car lock checks late night. I know, they left a card and friendly note reminding me to lock my car at night. "
    1
    Flag
  • Angela G.
    "Dunedin is a great location to live. A lot of little shops everywhere and it’s close to the water. Downtown Dunedin is beautiful and honeymoon island is minutes away"
    6
    Flag
  • Tiffany W.
    "Great location. Great vibe. Great people. Great location for any age. Great for visiting or living. "
    0
    Flag
  • Earphd
    "There morning traffic is quite heavy, as is the traffic from 3:30pm to 5:30pm. Otherwise, there is an easy foow of traffic."
    0
    Flag
  • Copa22316
    "It is a very comfortable but also safe neighborhood. There is always some thing of a variety of events going on through out Dunedin . Fun for family but also enjoyable for individuals which tend to meet and greet new people from the area or here visiting on vacation. The weather is nuteral in the winter months, sunshine always shinning. It’s hot in the summer in which people relax and cool off in a pool or in one of many beaches that are readily available.its a nice place to visit but I would definetiy love to live here! Me and many people feel the same way, concluding in most visitors do in fact move here!"
    0
    Flag
  • Marilynnalewajek
    "There are many dogs in our neighborhood. We have two. You see many people walking their dogs and there are some excellent dog parks in the area."
    2
    Flag
  • Shannon P.
    "Pretty easy to get in and out of neighborhood. CR1 can get bad during rush hours but it’s doable. Speed limits are strictly enforced "
    1
    Flag
  • Patpatti
    "Dunedin is a very welcoming town for dogs. Many areas for them. Drive thru the downtown area huge mural of dog. "
    1
    Flag
  • Cathyrewald4132019
    "The Jolley Trolley is great to go up and down the beaches. There is also busses that go through the area also. "
    1
    Flag
  • PC
    "Dunedin has craft shows, movie nights down town many locally owned Restaurants and businesses. Farmers market downtown. Christmas celebration with a boat show at the downtown park. "
    0
    Flag
  • Scshields97
    "It’s a great place to raise a family. The location to the community center and the pool and splash park are awesome. "
    0
    Flag
  • Babs L.
    "Almost every one has a dog here. Pets are welcome in stores and restaurants as well. They even set out water for pets downtown. "
    5
    Flag
  • Dpero
    "ride to work in golf cart. everything in this magical town is close. public transportation is readily available "
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

71 pet-friendly rentals in Dunedin, FL

Explore by feature - Garage

38 rentals with a garage in Dunedin, FL

Explore by feature - Air Conditioning

136 rentals with air conditioning in Dunedin, FL

Explore by feature - Pool

60 rentals with a pool in Dunedin, FL

Explore by feature - Washer/dryer

125 rentals with a washer/dryer in Dunedin, FL

Explore by feature - Outdoor Space

32 rentals with an outdoor space in Dunedin, FL

Homes for sale near 533 Chicago Ave

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Off Market Homes Near 533 Chicago Ave

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