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Carol Bernard
REALTOR®
(941) 580-2933
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$1,400,000

105 21st Avenue Saint Pete Beach, FL 33706 Residential - Single Family Active

  • 105 21st Avenue, Saint Pete Beach, FL 33706 Main Photo

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Description

The 1934 Historic Pineapple house is on the market and should be on your radar! This rare 92 year old Coastal Compound in the Heart of Pass-a-Grille is a one-of-a-kind property offering the perfect blend of historic island charm and modern updates with a beautifully renovated 3-bedroom, 2-bath main residence plus a second story 2-bedroom, 2-bath guest house, separated by a large solid wood and insulated conjoining door that offers the new buyer the option of having a 5-bedroom 4-bath with two kitchens, two indoor laundry locations, with endless possibilities for extended family, guests, or additional income potential.No Pass-a-Grille parking problem here as the home has a side by side two vehicle parking garage and two vehicle carport.Rich in character, the main home features soaring tongue-and-groove ceilings, exposed wood beams, original hardwood floors, and abundant natural light throughout. The updated kitchen offers shaker cabinetry, stone countertops, stainless steel appliances, and leads into the living spaces designed for relaxed coastal living. The spacious second floor primary suite is timeless and serves as a private retreat with a spa-inspired bath, and connecting bonus room perfect for a home office or coffee/wine bar. The additional guest bedrooms provide comfort for family and guests.The attached guest house has been thoughtfully updated maintaining its timeless coastal character, offering a full kitchen, spacious living area, two bedrooms, and two full baths.The exterior private and a covered entertainment area boasts a large kitchen counter, flat screen tv, and power and gas line to add outdoor refrigerator and and gas grill, perfect for gathering after a day at the beach.Located just steps from the sugar sand beaches of Pass-a-Grille, boutique shopping, waterfront dining, marinas, and historic 8th Avenue, this exceptional property offers a rare opportunity to own one of the area's classic island homes. Whether you're searching for a primary residence, vacation retreat, or an investment with exceptional flexibility, this unique coastal compound truly has it all.The 2/2 guest quarters is currently rented for $3000 a month plus renter pays utilities. Main house rents monthly between $6000 to $15,000 a month depending on the season. 24 hour notice for showings as the property is currently occupied. Currently July, August, December 2026 and January, March-April 14, 2027 are rented.

Property Highlights

Property Type: Residential - Single Family
Cooling: Central Air
Fenced: Yes
Garage: 2 car attached
Heating: Central
Lot Size: 0.11 Acres
Roof Type: Metal
Stories: 2.0
Taxes: $14,666
Year Built: 1934

General Information

Bedrooms: 5
Bathrooms: 4 Full
Sqft: 2,765
County: Pinellas
High School: Boca Ciega High-PN
Subdivision: PHILLIPS DIV REV MAP
Listed By:
Brandon Tecklenburg EXP REALTY 727-592-2286

Amenities

Ceiling Fans(s)
Stone Counters
Balcony
French Doors
Outdoor Shower
Rain Gutters

Room Information

Kitchen: 13.6x8.6
Living Room: 13.6x14.9
Primary Bedroom: 38.5x17

Property Features

Additional Rooms: Bonus Room
Appliances: Disposal
Days on Site: 1
Directions: From Gulf Blvd heading south, GUlf Blvd turns into Pass a Grille way. At the stop sign, turn right onto 21st Ave property will be on the right
Exterior: Frame, Wood Siding
Fencing: Fenced, Vinyl
Fireplace: Wood Burning
Fireplace Y/N: Yes
Flood Zone Code: AE
Flooring: Luxury Vinyl, Tile
Foundation: Pillar/Post/Pier
Garage Dimensions: 26x17
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot: Historic District, Near Golf Course, Near Marina, Near Public Transit, Sidewalk
Lot Dimensions: 0.11
Other Structures: Guest House
Ownership: Fee Simple
Parking: Garage Faces Rear
Parking Notes: Garage Faces Rear
Patio/Porch: Covered, Enclosed, Patio
Pets Allowed: Yes
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Sewer: Public Sewer
Showing Instructions: Appointment Only, Lock Box Electronic, ShowingTime
Special Sale Provisions: None
Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
Water: Public
Water Access Y/N: No
Windows: Blinds
$1,400,000
5beds
4.0baths
2,765sqft
2cars
New to the Market Active
BEDS5 BATHS4 full SQUARE FEET2,765 MLS#TB8520827
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONPHILLIPS DIV REV MAP

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105 21st Avenue, Saint Pete Beach, FL 33706.

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Estimated Payment

$ 6,352.47 per month $4,721.97 Principal & Interest $1,222.17 Property Tax $408.33 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/28/2026. The listing information on this page last changed on 06/28/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sun 06/28/2026 12:00:22 AM EST) or Stellar MLS (last updated Sat 06/27/2026 11:45:50 PM EST). Real estate listings held by brokerage firms other than Wagner Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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