500 Chicago Ave, Dunedin, FL 34698
OFF MARKET

$864,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,926 sqft (on 0.26 acres)

500 Chicago Ave, Dunedin, FL 34698

Est. Refi. Payment $5,798/mo*
Refinance Your Home
Currently Off Market - Sold May 30, 2018 for $460,000

Home Value

Trulia Estimate
$865K
Since last month
Decreased$14K (-1.6%)
Since last year
Increased$13K (+1.6%)
Since last sale
Increased$404K (+87.8%)
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 +193% in the last 10 years
MonthEstimated value
2026
August 2026$864K
August 2026$863K
July 2026$878K
June 2026$892K
May 2026$884K
April 2026$885K
March 2026$908K
February 2026$880K
January 2026$857K
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
501 LOUDEN AVENUE, Dunedin, FL
0.16
Single-Family Home
$450,000
12/22/25
3
2
1,358
554 LOUDEN AVENUE, Dunedin, FL
0.16
Single-Family Home
$614,000
01/30/26
2
2
1,806
250 ABERDEEN STREET, Dunedin, FL
0.21
Single-Family Home
$965,000
03/19/26
3
2
1,784
224 LYNDHURST STREET, Dunedin, FL
0.24
Single-Family Home
$600,000
08/12/26
3
2
1,359
220 LYNDHURST STREET, Dunedin, FL
0.26
Single-Family Home
$650,000
07/28/26
3
3
1,952
612 MAGNOLIA STREET, Dunedin, FL
0.26
Single-Family Home
$501,000
10/23/25
3
2
1,445
525 BROADWAY, Dunedin, FL
0.12
Single-Family Home
$650,000
10/13/25
2
2
1,138
266 LYNDHURST STREET, Dunedin, FL
0.16
Single-Family Home
$850,000
02/19/26
2
2
2,104
412 BELTREES STREET, Dunedin, FL
0.13
Single-Family Home
$597,500
12/08/25
2
2
1,688
620 JACARANDA STREET, Dunedin, FL
0.26
Single-Family Home
$551,000
06/12/26
3
2
1,474

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
442 LYNDHURST STREET, Dunedin, FL 34698
0.04
$615,000
4
2
1,624
Recently Sold
515 DOUGLAS PLACE, Dunedin, FL 34698
0.02
$940,000
4
3.5
2,415
Recently Sold
456 CHICAGO AVENUE, Dunedin, FL 34698
0.03
$1,265,000
4
2
1,960
Recently Sold
510 DOUGLAS PLACE, Dunedin, FL 34698
0.03
$929,900
4
3.5
2,316
For Sale
453 DOUGLAS AVENUE, Dunedin, FL 34698
0.04
$939,600
4
3
1,806
Off Market
448 LOCKLIE STREET, Dunedin, FL 34698
0.10
$1,499,000
3
3
4,373
For Sale
605 DOUGLAS AVENUE, Dunedin, FL 34698
0.13
$736,500
3
2.5
1,623
Off Market
525 BROADWAY, Dunedin, FL 34698
0.12
$636,300
2
2
1,138
Off Market
600 HIGHLAND AVENUE, Dunedin, FL 34698
0.14
$608,200
2
2
1,080
Off Market
600 HIGHLAND AVENUE LOT 1, Dunedin, FL 34698
0.14
-
-
-
-
Off Market
501 BROADWAY, Dunedin, FL 34698
0.12
$985,000
2
1.5
1,236
For Sale
412 BELTREES STREET, Dunedin, FL 34698
0.13
$597,500
2
2
1,688
Recently Sold

Local Information

  • Map ViewExplore the area around 500 Chicago Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1953
0.26 acre lot
1,926 sqft
$449/sqft
Garage

About this House

Fantastic opportunity to own a premier property in Dunedin! This newly renovated home is just 4 blocks from the popular Main Street attractions in downtown and 2 blocks to the waterfront. No detail was left unnoticed from the modern renovation features, to the incredible outdoor living space with pool this home has it all. Situated on over a quarter acre lot, the home has been completely upgraded in 2015 with all new plumbing, sewer replaced, water piping, gas piping, AC unit, roof, flooring, paint, outdoor kitchen, pool, landscaping, and fencing. A split floor plan, this home features, 3 bedrooms, 2 baths, bonus family room, indoor laundry and wide open kitchen with gas appliances and separate dining area. Outside you will find a one-of-a-kind, fully stocked kitchen featuring an outdoor sink, kegerator, ice maker, gas grill with separate gas range, Big Green Egg, and mini refrigerator and freezer all of which convey with the home. It is also wired for a flat screen TV and surround sound speakers. The 10k gallon pool was put in in 2015 and features new paver decking, a beach with fire-pit, and grassy area for pets/kids. Primely located near downtown, this home is competitively priced for today's market, & offers an amazing opportunity to own a premier property in Dunedin at an exceptional value.
500 Chicago Ave, Dunedin, FL 34698 is a 3 bedroom, 2 bathroom, 1,926 sqft single-family home built in 1953. It last sold for $460,000 on May 30, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $864,800, with a rent estimate of $4,455/month.

Home Details for 500 Chicago Ave

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile
Interior Details
Number of Rooms: 8Types of Rooms: Dining RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Cement ConcreteFoundation Type: FootingLawnPatioPorch
Pool
Pool
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1953Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Bungalow

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price and Tax history

DateEventPrice
May 30, 2018
Source: N/A
Sold
$460,000
Mar 29, 2018
Source: Agent Provided
Pending
$499,000
Mar 20, 2018
Source: Agent Provided
PriceChange
$499,000
Price decreased by 9%
Feb 5, 2018
Source: Agent Provided
PriceChange
$549,000
Price decreased by 6%
Feb 1, 2018
Source: Agent Provided
PriceChange
$584,000
Price decreased by 3%

Market trends in Dunedin

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$403K
$17.52KMoM
Sale-to-List Price
96.8%
0.2%MoM
Price per sq ft
$296
$2MoM
Available listings
322
11MoM

Around this home

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

LGBTQ Local Legal Protections

Frequently asked questions about 500 Chicago Ave

  • What is 500 Chicago Ave estimated to be worth?
    Trulia's estimated value for 500 Chicago Ave in Dunedin, FL is $864,800.
  • What is the price history for 500 Chicago Ave?
    500 Chicago Ave in Dunedin, FL last sold for $460,000 in May 2018.
  • Is Dunedin a buyer's or seller's market?
    Dunedin is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Dunedin?
    The median sale price in Dunedin is $403K. That is down $17.52K from the prior month.
  • Does 500 Chicago Ave have air conditioning?
    Yes, 500 Chicago Ave in Dunedin, FL has air conditioning.
  • Does 500 Chicago Ave have a pool?
    Yes, 500 Chicago Ave in Dunedin, FL has a pool.

Explore by feature - Pet Friendly

60 pet-friendly rentals in Dunedin, FL

Explore by feature - Garage

31 rentals with a garage in Dunedin, FL

Explore by feature - Air Conditioning

114 rentals with air conditioning in Dunedin, FL

Explore by feature - Pool

53 rentals with a pool in Dunedin, FL

Explore by feature - Washer/dryer

95 rentals with a washer/dryer in Dunedin, FL

Explore by feature - Outdoor Space

19 rentals with an outdoor space in Dunedin, FL

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Off Market Homes Near 500 Chicago Ave

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