4852 99th Way North

Off Market

4852 99th Way North

Bay Pines FL 33708

4356 sq. ft.

12667 sq. ft.

Single-Family

Last sold for $1,020,000

Christopher Wescott, last sold this property on 12 March 2026 after 34 days on market.

Overview

Refined One-Level Luxury Home in Sought-after Bay Pines Estates within minutes to Madeira Beach. This exceptional custom-built residence offers 3,393 square feet of beautiful living space (4,356 total square feet) thoughtfully designed across a single-level floor plan. With an emphasis on architectural integrity, privacy, and effortless entertaining, the home delivers a rare blend of sophistication and functionality. The residence features four bedrooms, including two expansive primary suites, three bathrooms,a stately office and an oversized two-car garage, making it ideally suited for both elegant family living and hosting on a grand scale. Originally constructed in 2005, the home makes a striking first impression with an arched entryway framed by substantial columns, setting the stage for the refined interiors within. Inside, soaring tray ceilings and generous ceiling heights enhance the open layout, complemented by polished hardwood floors, curated designer tones, and modern finishes that balance warmth with understated luxury. Architectural enhancements include crown molding, custom window trim, LED smart lighting, and oversized windows that bathe the home in natural light. The thoughtfully designed bedroom layout prioritizes privacy, with three bedrooms offering en-suite accommodations. The primary suite is privately positioned opposite the additional bedrooms, creating a true owner’s retreat, while a second oversized suite provides exceptional flexibility for multi-generational living or extended guests. At the heart of the home, the great room unfolds as a sunlit gathering space, seamlessly connecting the kitchen and dining areas for effortless everyday living and entertaining. From the moment you enter your eyes are drawn through the main living areas to the remarkable outdoor entertaining retreat, creating a sense of openness and flow throughout. Significant upgrades enhance both comfort and long-term value, including a custom-designed, heated saltwater pool and oversized spa with full screened enclosure, completed in 2022. A solar panel system, also added in 2022, has historically offset the home’s typical electrical usage based on prior occupancy. Additional improvements include dual HVAC systems and a comprehensive kitchen remodel with updated appliances completed in 2020. Situated at an elevated 44-foot elevation and located in Flood Zone X, the property offers the notable benefit of no flood insurance requirement. Outdoors, a private resort-style setting awaits, designed for year-round enjoyment. The screened enclosure features remote-controlled custom privacy blinds, an entertainer-focused layout, and seamless indoor-outdoor living. Meticulous maintenance, thoughtful garage upgrades, and a premier location further distinguish this offering. Move-in ready and impeccably upgraded, this residence presents a rare opportunity to experience elevated Florida living in one of the area’s most desirable communities.

Features

4 bedrooms

3 bathrooms

2 carspaces

2 garage spaces

4356 sq. ft. floor area

12667 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Bay Pines over the last 12 months, the estimated median property value of 4852 99th Way North is $1m.

Median value

$1m

Estimated value range

$235k - $3.6m

Median days on market

Estimated value trend

27%

increase over the last 12 months

Average days on market is based on recent, comparable sales in Bay Pines. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 4852 99th Way North

2026

Sold

$1,020,000

12 Mar 2026 by Christopher Wescott, of CHARLES RUTENBERG REALTY INC

2020

Sold

$629,000

24 Nov 2020 by Jessica Holand, of KELLER WILLIAMS SOUTH SHORE

Happy sellers in Bay Pines

73%

73% of sellers in Bay Pines reported that their sale price either exceeded or met their price expectations.

Bay Pines stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 14 reviews in Bay Pines over the last 12 months.

Local market activity for 4 bedroom single-family properties in Bay Pines

In the last 12 months, 36 four-bedroom single-family properties similar to 4852 99th Way North, have been sold.

This represents a 10% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Bay Pines for a market analysis.

Patricia Hughes

at COLDWELL BANKER REALTY

(32 reviews)

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Bonnie Schultheis PA

at CHARLES RUTENBERG REALTY INC

(15 reviews)

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Ellen Schwandt

at THE AMBROSIO GROUP

(57 reviews)

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Tara Beheshti

at COASTAL PROPERTIES GROUP INTERNATIONAL

(50 reviews)

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Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Bay Pines

Patricia Hughes

Patricia Hughes is a recommended agent for Bay Pines. They have 4 local sales and collected 5 local reviews across the last 12 months.

5 (32 reviews)
5 Reviews in Bay Pines
4 Sales in Bay Pines

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Bonnie Schultheis PA

Bonnie Schultheis PA is an award winning recommended agent for Bay Pines. They have 4 local sales and collected 5 local reviews across the last 12 months.