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$2,300,000

18 Winston Dr Belleair, FL 33756

3 beds
3 full, 1 partial
3,444 sqft
0.2 acres
$668 / sqft
House

Property details

About 18 Winston Dr

This stunning Belleair waterfront pool home is a perfect blend of modern elegance and coastal living, offering a lifestyle of luxury and tranquility. As you step through the grand entrance, 20-foot ceilings soar above, and natural light cascades across the gorgeous tile floors, highlighting the breathtaking water views that fill every corner of the home. The open floorplan revolves around a sleek, sophisticated white kitchen, featuring a 16-foot quartz island with seating and hidden pop-up outlets. Designed with entertaining in mind, this culinary space includes a built-in bar with a wine fridge, appliance garage, and a dedicated coffee hutch, creating a clean, clutter-free ambiance. Behind a barn door, a walk-in pantry offers ample storage, while a separate buffet bar with a chevron backsplash, floating shelves, and a sink is ideal for large gatherings. The kitchen flows effortlessly into a spacious family room and dining room, where French doors and ample windows provide an ever-changing backdrop of water views and a cozy fireplace sets the perfect mood for cooler evenings. Outside, a sparkling pool and expansive dock await—it's as if you’re floating on the water as you enjoy sweeping sunset views. For boating and fishing enthusiasts, the dock is equipped with a lift and a floating dock, making it easy to launch kayaks or paddleboards. Nature lovers will be captivated by the ospreys, egrets, and other shorebirds that call this area home. Retreat upstairs to the luxurious primary suite, a serene haven with two walk-in closets, a private balcony with a pergola, and mesmerizing water views. The ensuite bath has been impeccably updated with double vanities featuring light-up drawers and cabinets, quartz counters, a defogger mirror, a soaker tub, a private water closet, and two skylights. A catwalk overlooking the family room leads to two additional guest rooms, each well-appointed with plentiful closet space, natural light, and a shared hall bath. The ground floor boasts a spacious over-sized two-car garage on one side, while the other side includes a one-car garage with a workspace and full bath—ideal for storing water toys or working on hobbies. With a 9-foot elevation to the living floor, this home is equipped with storm shutters, sealed casement windows, French doors, and a raised pool with a waterfall feature for added peace of mind. Perfectly located near shopping, local dining, and two exclusive private golf clubs, this home is just a short drive from world-famous, white-sand beaches, making this the perfect home to make your Florida lifestyle dream become a reality.

Highlights

Home typeSingle Family Residence
HeatingCentral, Electric, Zoned
StatusActive
CoolingCentral Air
Size3,444 sqft
Lot size0.21 Acres
Year built1988
ParkingBath In Garage, Circular Driveway, Garage Door Opener, Oversized, Workshop in Garage
MLS #TB8321661
Attached garage3 spaces
WaterfrontCanal
FireplaceLiving Room, Wood Burning
Private poolYes

Summary

  • Partial Bathrooms: 1
  • Full Bathrooms: 3
  • Appliances: Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Refrigerator, Trash Compactor, Washer, Wine Cooler
  • Flooring Type: Carpet, Tile, Terrazzo, Wood
  • Interior: Built-in Features, Ceiling Fans(s), Central Vaccum, Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Split Bedroom, Stone Counters, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
  • Fireplace: Living Room, Wood Burning
  • Total Bedroom Count: 3
  • Garage Space: 3 spaces
  • Attached Garage: Yes
  • Private Pool: Yes
  • Parking: Bath In Garage, Circular Driveway, Garage Door Opener, Oversized, Workshop in Garage
  • Waterfront: Canal
  • Exterior: Balcony, French Doors, Hurricane Shutters, Lighting
  • Heating: Central, Electric, Zoned
  • Cooling: Central Air
  • List Price: $2,300,000
  • Price/SqFt: $667
  • HOA Amount: $0
  • Annual Tax Amount: $16,246
  • Tax Year: 2023
  • Lot: Cul-De-Sac, Flood Zone, City Lot, Near Golf Course, Paved
  • Directions: From West Bay Drive in Belleair Bluffs turn North on Bluff View Drive to Belleair then turn West on Winston Drive to address.
  • Year Built: 1988
  • Stories: 3
  • Living Area: 3,444 SqFt
  • Lot Size: 0.21 Acres
  • MLS Number: TB8321661
  • MLS Name: MFRMLS
  • Office Name: COLDWELL BANKER REALTY
  • Office Phone: (727) 581-9411
  • Listing Agent: Martha Thorn

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Last updated on: 7/23/2025, 11:49:28 PM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.

Price information

Property sales

DateEventPrice
Feb 13, 2018
Home Sold
$900,000

Tax history

YearAssessmentProperty Tax
2023$859,322$16,246
2022$834,293$15,840
2021$809,993$15,840
2020$884,410$16,016
2019$847,832$18,060
2018$777,387$16,683
2017$720,492$15,264

History based on county public records data.

Nearby schools

6

Mildred Helms Elementary

Public Magnet PK-5

1.8 mi

561 Clearwater Largo Rd S

5

Ridgecrest Elementary

Public Magnet KG-5

2.2 mi

1901 119th St

8

Ponce de Leon Elementary

Public District PK-5

2.5 mi

1301 Ponce De Leon Blvd

School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.

All data from GreatSchools

Neighborhood

The neighbors living near this home have an average income of $114,858. Residents of Belleair, FL typically earn between $100k-200k each year. The majority of families are married, no kids. The majority of residents in this area have post secondary degree education.

How much money do the neighbors make?

15%
<35k
23%
35k-100k
43%
100k-200k
19%
200k+

What level of education do the neighbors have?

High School Diploma
Post Secondary Degree
Masters Degree
Doctorate

What types of families live nearby?

30%
Single, No Kids
5%
Single, with Kids
40%
Married, No Kids
25%
Married, with Kids

Are the neighbors home owners or renters?

Home Owners
Renters

How old are people in this area?

13%
<11 yrs old
9%
12-17 yrs old
7%
18-34 yrs old
52%
35-64 yrs old
19%
65+ yrs old

What do the neighbors do for fun?

  • Skiing/snowboardingSkiing/snowboarding
  • Hiking/backpackingHiking/backpacking
  • PGA/LPGAPGA/LPGA

Where do the neighbors shop?

  • NordstromNordstrom
  • Nordstrom RackNordstrom Rack
  • Chico'sChico's

Where do the neighbors go to eat?

  • California Pizza KitchenCalifornia Pizza Kitchen
  • ChipotleChipotle
  • Bonefish GrillBonefish Grill

What do the neighbors drive?

  • BMWBMW
  • MazdaMazda
  • CadillacCadillac

What do the neighbors listen to?

  • Talk/PersonalityTalk/Personality
  • RockRock
  • ClassicalClassical
All data provided by Home Junction and Claritas

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Frequently asked questions

About 18 Winston Dr

The listing price of 18 Winston Dr property is $2,300,000.

The property 18 Winston Dr is a house located in Belleair, Florida, 33756.

Active Listing: 18 Winston Dr is For Sale (Active/New) which means the seller is accepting offers.

The nearby schools for 18 Winston Dr are: Mildred Helms Elementary (GreatSchools Rating 6/10), Ridgecrest Elementary (GreatSchools Rating 5/10), Ponce de Leon Elementary (GreatSchools Rating 8/10), Largo Middle School (GreatSchools Rating 4/10), Pinellas Academy of Math and Science (GreatSchools Rating 4/10), Plato Seminole (GreatSchools Rating 5/10), Dropout Prevention School (GreatSchools Rating 2/10), Largo High School (GreatSchools Rating 5/10), Pinellas Gulf Coast Academy (GreatSchools Rating 2/10).

According to the records, the last property tax for 2023 is $16,246 (source: MLS/based on county public records data).

The last sale was on February 13, 2018 for $900,000 (source: MLS/tax record).

The property at 18 Winston Dr has 3 bedrooms and 3 full and 1 half bathrooms.

The property 18 Winston Dr is 3,444 SqFt (source: MLS/tax record).

The year of construction for 18 Winston Dr is 1988.

This home is located at 18 Winston Dr in Belleair, FL and zip code 33756. This 3,444 square foot home, which was built in 1988, sits on a 0.21 acre lot. Features: 3 bedrooms, 4 bathrooms. It has been listed on Rocket Homes since November 15, 2024 and is currently priced at $2,300,000.

In June 2025, from all listings sold in Belleair, FL there were more than 1 sold above asking price, over 6 sold below and more than 0 were sold right at the asked price. In June 2025 in Belleair, FL there were 4.7% less homes for sale than in May. The median list price of listings available in June 2025 was $800,000, while the average time on the real estate market was 114 days.

From Rocket Homes Real Estate and based on county public records data.

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