Model SnapshotRegal 36 Grande Coupe
2020–present
A 37-foot hardtop express with Volvo V8 sterndrives and joystick: the lift-friendly Grand…
5 for sale · 2 sold (12 mo)
Chicago & Lake Michigan
Used Regal Boats for Sale in Chicago
Chicago and Lake Michigan, from Michigan City and New Buffalo up through Waukegan, Kenosha and Milwaukee, is a strong freshwater Regal market.
40
Boats for sale
38
New this week
2
Sold in last 12 months
82
Avg days on market
Represented by PYM
All 40 Regals on the market · 1 in Chicago
PYM2021 Regal 33 XO
Sunny Isles Beach, Florida
$269,999
PYM2022 Regal 42 XO
Clearwater, Florida
$695,000
In Chicago2021 Regal 38 Grande Coupe
Chicago, IL
$475,000
Outside Florida2022 Regal 38 Grande Coupe
Harrison Twp, MI
$521,000
Outside Florida2023 Regal 38 SAV
Harrison Twp, MI
$595,000
Outside Florida2024 Regal 38 Grande Coupe
Traverse City, MI
$539,000
Outside Florida2020 Regal 33 OBX
Mattituck, NY
$229,900
Outside Florida2025 Regal 50 SAV
Brick, NJ
$1,499,727
Outside Florida2025 Regal 36 Grande Coupe
Wilmington, NC
$449,000
Outside Florida2023 Regal 36 Grande Coupe
Buford, GA
$429,900
Outside Florida2020 Regal 38 XO
Orange Beach, AL
$379,000
Outside Florida2022 Regal 38 Grande Coupe
Sandusky, OH
$564,900
Outside Florida2021 Regal 42 Fly
Georgetown, MD
$614,900
Miami2023 Regal 38 FXO
Aventura, FL
$789,990
Outside Florida2022 Regal 42 FXO
Charleston, SC
$654,000
Fort Lauderdale2024 Regal 38 XO
Boca Raton, FL
$599,000
Florida – Other2022 Regal LX36
New Smyrna Beach, FL
$355,000
Florida – Other2021 Regal 38 XO
Daytona Beach, FL
$439,999
Outside Florida2020 Regal 38 Grande Coupe
Bowleys Quarters, MD
$479,999
West Palm Beach2022 Regal 38 SAV
Stuart, FL
$519,900
Outside Florida2025 Regal 38 FXO
Pasadena, MD
$899,000
Miami2024 Regal LX9
Aventura, FL
$229,650
Outside Florida2025 Regal LX43
Osage Beach, MO
$1,300,000
Miami2022 Regal 36 Grande Coupe
North Miami, FL
$369,000
Outside Florida2017 Regal 42 Fly
Greenport, NY
$415,000
Miami2020 Regal 42 Fly
Miami Beach, FL
$475,000
Outside Florida2024 Regal 36 Grande Coupe
Burlington, VT
$499,900
Fort Lauderdale2019 Regal 33 OBX
Pompano Beach, FL
$179,900
Fort Lauderdale2021 Regal 33 SAV
Lauderdale-by-the-Sea, FL
$239,000
Fort Lauderdale2022 Regal 33 XO
Fort Lauderdale, FL
$279,000
Outside Florida2026 Regal LX43
Ship Bottom, NJ
$1,599,727
Florida – Other2023 Regal 38 SAV
Destin, FL
$579,990
Outside Florida2024 Regal 36 XO
Charleston, SC
$498,000
Outside Florida2022 Regal 36 Grande Coupe
Prospect, KY
$415,000
Outside Florida2024 Regal 38 XO
Boston, MA
$545,000
Florida – Other2025 Regal 36 XO
Destin, FL
$535,000
West Palm Beach2022 Regal 33 SAV
Boynton Beach, FL
$319,999
Tampa Bay2017 Regal 33 XO
Tampa, FL
$189,995
Fort Lauderdale2025 Regal 50 SAV
POMPANO BEACH, FL
$1,499,995
West Palm Beach2025 Regal 38 SAV
Stuart, FL
$599,000
Recorded Regal sales
- 2
- Sales recorded (12 months)
- 82
- Avg days to sell
- 2023
- Most active model year
Sale prices, dates and the spread from asking are in the sold report.
Get the Chicago Regal sold report
Individual sale prices and dates — delivered privately after your request.
Regal models in Chicago
Model SnapshotModel SnapshotRegal 38 Grande Coupe
2020–present
A 38-foot hardtop express with a full-beam feel, twin Volvo V8 sterndrives with joystick,…
5 for sale · 2 sold (12 mo)
Model SnapshotRegal 38 SAV
2020–present
Regal's flagship outboard day-yacht: a center-helm sport activity vessel that fishes, div…
4 for sale · 7 sold (12 mo)
Verified Model GuideRegal 38 XO
A 38-foot triple-outboard sport cruiser bridging Regal's luxury cruisers and outboard exp…
4 for sale · 6 sold (12 mo)
Verified Model GuideRegal 33 XO
Outboard-powered express cruiser on a C. Raymond Hunt hull — big-boat ride in 34 feet.
3 for sale · 8 sold (12 mo)
Model SnapshotRegal 42 Fly
2017–present
Regal's only flybridge yacht: twin Volvo IPS diesels, two staterooms, and joystick handli…
3 for sale · 3 sold (12 mo)
Model SnapshotRegal 33 OBX
2018–present
Regal's 34-foot outboard bowrider: a big open cockpit, a cuddy with a head, and twin Yama…
2 for sale · 3 sold (12 mo)
Model SnapshotRegal 33 SAV
2018–present
The boat that started Regal's SAV line: a twin-outboard, cabin-equipped sport activity ve…
2 for sale · 6 sold (12 mo)
Verified Model GuideRegal 36 XO
Outboard-powered express cruiser built for Florida day-and-overnight use.
2 for sale · 12 sold (12 mo)
Find · vet · negotiate
We find the boat worth seeing
Our process is find, vet, negotiate.
We vet it before you travel
We find the right Regal anywhere on the Lake Michigan shoreline, including boats coming out of long-term local ownership.
We negotiate on recorded numbers
We vet it against recorded sold data, winterisation and service records and an independent survey and sea trial.
Three ways to start
Market analysis
Review recorded Regal sales in Chicago. Individual prices and dates are delivered privately by email.
Request the sold reportValue my Regal
Selling or trading up needs a defensible number. We build one from recorded sales.
Get my boat evaluatedAudit my listing
Listed but not getting showings? We audit photos, copy, pricing and exposure.
Audit my listingFrom the dock in Chicago
Verified-aboard notes for Chicago are being added as we walk boats here.
Michael J. JohnsonParticipating PYM brokerVerified-aboard notes for Chicago are being added as we walk boats here.
Boat Protection Experts
Extended protection for powerboats up to 80 feet and 13 years old, quoted online in minutes.
Chicago Regal questions
The questions buyers ask us most in this market.
Are freshwater Regals really worth more?
Generally yes. Freshwater boats typically show far less corrosion on drives, hardware and electrical systems, which is why buyers in the South actively look for them.
Can you arrange delivery from Chicago to Florida?
Yes. Over-the-road transport is routine on these boats, and we coordinate quotes and scheduling as part of the purchase rather than leaving it to you afterwards.
What should I look for in winter storage history?
Documented winterisation, indoor or shrink-wrapped storage and consistent spring commissioning are the difference between an easy boat and an expensive one. We ask for the records.
How short is the buying season here?
Inventory and pricing move with the season, and late-season boats are often negotiable. Our Chicago sold report shows recorded prices, dates and days on market across the year.