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575 MADISON AVENUE, NEW YORK, NY 10022. 212.891.7000 © 2025 DOUGLAS ELLIMAN REAL ESTATE. EQUAL EMPLOYMENT OPPORTUNITY PROVIDER. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES, OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS, AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT, OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY.LISTING DATA REFRESHED ON NOV 17 2025 AT 3:41 AM.

DOUGLAS ELLIMAN IS A LICENSED REAL ESTATE BROKER IN CALIFORNIA WITH LICENSE # 01947727, COLORADO WITH LICENSE # EC100053892, CONNECTICUT WITH LICENSE # REB.0314827, THE DISTRICT OF COLUMBIA WITH LICENSE # REO40000160, FLORIDA WITH LICENSE # CQ1020232, MARYLAND WITH LICENSE # 645270, MASSACHUSETTS WITH LICENSE # 422764, NEVADA WITH LICENSE # 1454643, NEW JERSEY WITH LICENSE # 0572105, NEW YORK WITH LICENSE # 10991211812, TEXAS WITH LICENSE # 9008706, AND VIRGINIA WITH LICENSE # 0226035659.

POWERED BY PURLIN.AI

500 S RIVERSIDE Dr

new smyrna beach, FL 32168

$1,475,000

  • 4 BR
    3 BA
    APPROX. 1,905 SF

INTERESTED? LET'S CONNECT

For the first time in decades, this rare riverfront treasure on historic Riverside Drive in New Smyrna Beach is available—an authentic circa 1900 4BR/3BA home with riparian rights to a deepwater dock & boathouse (needs repair) just across the street. Perfectly positioned on a corner lot with a detached oversized 2-car garage (32x24), this charming property sits within the exclusive Bed & Breakfast Overlay Zone (allowing short-term rentals with a 2-night minimum)—a truly uncommon find on Riverside Drive. Step onto the wide front porch and enjoy the serenity of boats passing by and gentle ocean and river breezes, just four blocks from the vibrant Canal Street Historic District, where you can stroll or golf cart to shops, restaurants, breweries, art shows, and the weekly farmers market. The first floor boasts river views from the living room, dining room, kitchen, and sunroom—all of which open to wraparound porches and decks perfect for entertaining. Two spacious bedrooms and two full baths are conveniently located downstairs, along with a laundry/mudroom that opens to the rear courtyard and garage. The second floor features a private primary suite with panoramic river views and access to a large balcony overlooking the water, plus an additional guest bedroom, full bath, and a second kitchen with its own balcony and stairway to the courtyard—ideal for rental income or extended family. With original hardwood floors throughout, charming period details like French doors, tall windows, herringbone brick entry, and exposed roof rafters under a certified metal roof (10–15 years of life remaining), this home embodies timeless craftsmanship. The kitchen blends history with modern convenience, featuring wood cabinetry, stone countertops, and stainless-steel appliances. Just across the bridge, you’ll find the lively Flagler Avenue beachside district for more shopping, dining, and nightlife—all just minutes from your porch swing. With a transferable termite bond, a solid power grid near Advent Hospital, and endless possibilities to restore or reimagine a new home, this property offers both historic charm and unmatched location in the heart of coastal New Smyrna Beach living. ALL INFORMATION IS ASSUMED ACCURATE BUT NOT GUARANTEED. ALL MEASUREMENTS ARE ESTIMATED. BUYERS AND THEIR AGENTS TO VERIFY ALL INFORMATION DEEMED IMPORTANT TO THEM.

Details

1,905 Sq Ft

7,500 Sq Ft Lot Size

Single Family Home

$4,313 Annual Tax

Built in 1943

MLS/Listing ID NS1086457

Amenities & Features

Parking - Off Street

Parking - Garage Faces Side

Parking - Alley Access

Wrap Around

Side Porch

Rear Porch

Porch

Patio

Front Porch

Deck

Covered

Water View

River Front

Parking - Oversized

Parking - Workshop in Garage

Style - Craftsman

Style - Historic Antique

Dishwasher

Disposal

Dryer

Microwave

Range

Refrigerator

Washer

Wine Refrigerator

Lot - City Lot

Lot - Historic District

Inside

Laundry Room

Built-in Features

Stone Countertops

Heating - Electric

Pillar Post Pier

Hardwood

Living Room Fireplace

Balcony

Storage

Cooling - Central Air

Construction - Wood Frame

Construction - Wood Siding

Style - Bungalow

Style - Cape Cod

Style - Cottage

Intracoastal Waterway

Metal

Parking - Golf Cart Parking

Lot - Sidewalk

Lot - Near Marina

Solid Wood Cabinets

Ceiling Fans

Crawlspace

Sidewalk

Rain Barrel/Cistern(s)

Style - Key West

Style - Florida

Style - Coastal

STELLAR

estimate my mortgage

TOTAL MONTHLY COST

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  • PRINCIPAL & INTEREST

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  • PROPERTY TAXES

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  • COMMON CHARGES

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HOME PRICE
DOWN PAYMENT
term
INTEREST

Interested in 500 S RIVERSIDE Dr?