367 FIVE ISLAND Drive, Saint Augustine, FL 32080
FOR SALE
3D VIEW
0.3 ACRES

367 FIVE ISLAND Drive
Saint Augustine, FL 32080

  • 4 Beds
  • 3 Baths
  • 2,627 sqft (on 0.30 acres)

$1,890,000

Est. Mortgage $11,513/mo*
Get Pre-Qualified

$1,890,000

Est. Mortgage $11,513/mo*
Get Pre-Qualified
4 Beds
3 Baths
2,627 sqft
(on 0.30 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

ICW access!
Welcome to your private waterfront sanctuary where refined luxury and effortless coastal living converge. This impeccably designed 4-bedroom, 3-bath residence has been thoughtfully curated with modern upgrades and premium finishes throughout.
At the heart of the home, a custom chef's kitchen impresses with striking waterfall countertops, gas-cooktop, designer lighting, and state-of-the-art fixtures perfectly suited for both everyday living and elevated entertaining. Seamlessly blending indoor and outdoor spaces, step onto the expansive $50,000 paver deck featuring a fully equipped gourmet outdoor kitchen with marble countertops and a new in-ground spa, ideal for hosting unforgettable waterfront gatherings.
Beyond, the impressive dock delivers a true boater's dream, complete with a twin wave-runner lift, a full boat lift, floating dock, kayak holders, and gangway providing effortless access to the deep water adventures. Watch dolphins and Mantatee wildlife from your own home. The upstairs primary suite is a serene retreat, offering a private balcony with sweeping lighthouse views an idyllic setting to enjoy breathtaking sunrises and sunsets. The spa-inspired primary bath is nothing short of extraordinary, custom walk-in closets, and a lavish oversized shower featuring six showerheads, including an 18-inch rainfall shower, showcasing marble tiles and stone-pebble flooring.

Additional highlights include elegant Jellyfish exterior lighting, an oversized 8-foot garage with a striking tri-color epoxy floor, and a living room designed to impress with an electric fireplace and triple sliding glass doors framing unobstructed water views. Outside, relax in the new 8-person hot tub nestled among beautifully designed pavers, creating a tranquil oasis under the open sky. The Antigua community offers an in-ground pool and kayak launch and is just a short drive away from shopping fine dining and the St. Augustine beach.

The dining room's extended bay window sets the stage for memorable evenings, offering stunning sunset views that elevate every meal. With all-new landscaping enhancing its curb appeal, this exceptional home embodies the pinnacle of waterfront luxury living where every detail has been carefully considered and every view is simply unforgettable.

Home Highlights

Parking
2 Car Garage
Outdoor
Patio
View
Intracoastal, Protected Preserve
HOA
$134/Monthly
Price/Sqft
$719
Listed
94 days ago

Home Details for 367 FIVE ISLAND Drive

Active Status

MLS Status: Active

Interior Features

Interior Details
Wet Bar
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2627 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water ConnectedAppliances: Convection Oven, Dishwasher, Disposal, Electric Oven, ENERGY STAR Qualified Dishwasher, ENERGY STAR Qualified Refrigerator, ENERGY STAR Qualified Water Heater, Gas Cooktop, Gas Water Heater, Instant Hot Water, Microwave, Plumbed For Ice Maker, Refrigerator, Tankless Water Heater, Water Softener OwnedDishwasherDisposalMicrowaveRefrigerator
Heating & Cooling
Heating: Central,ZonedHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Number of Fireplaces: 1Fireplace: ElectricSpa: PrivateHas a FireplaceHas a Spa
Windows, Doors, Floors & Walls
Flooring: Carpet, Stone, Tile, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Stone, Tile, Wood
View
Has a ViewView: Intracoastal, Protected Preserve
Security
Security: Carbon Monoxide Detector(s), Security System Owned, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, PatioFencing: Fenced, Back Yard, Wrought IronOther Structures: Outdoor Kitchen, Shed(s)Exterior: Balcony, Boat Lift, Dock, Fire Pit, Outdoor Kitchen
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached,Covered,Electric Vehicle Charging Station(s),Garage Door Opener
Frontage
WaterfrontWaterfront: Intracoastal, Marsh, Navigable WaterRoad Frontage: City StreetRoad Surface Type: AsphaltOn Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Days on Market: 94

Property Information

Year Built
Year Built: 2022
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Craftsman,Traditional
Building
Construction Materials: Composition SidingNot a New ConstructionNot Attached Property
Property Information
Condition: Updated/RemodeledParcel Number: 1612520850

Price & Status

Price
List Price: $1,890,000Price Per Sqft: $719
Status Change & Dates
Possession Timing: Close Of Escrow, Negotiable

Media

Location

Direction & Address
City: St. AugustineCommunity: Antigua

Agent Information

Listing Agent
Listing ID: 2128125

Community

Not Senior Community

HOA

HOA Name: Leland MangementHOA Phone: 904-483-2985Has an HOAHOA Fee: $403/Quarterly

Lot Information

Lot Area: 0.30 acres

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous

Mls Number: 2128125Water ViewWater View: Intracoastal

Additional Information

HOA Amenities: Pool
Last check for updates: about 3 hours ago
Listing courtesy of Beatrice Bredeson, (847) 648-0626
MOMENTUM REALTY, (904) 903-1558
Source: realMLS, MLS#2128125
Also Listed on realMLS.

Price History for 367 FIVE ISLAND Drive

DatePriceEventSource
02/02/2026$1,890,000Listed For SalerealMLS #2128125
11/01/2025$14,000ListingRemovedZillow Rentals
10/13/2025$1,850,000ListingRemovedrealMLS #2074599
08/22/2025$14,000Listed For RentZillow Rentals
07/23/2025$1,850,000PriceChange
realMLS #2074599
05/14/2025$1,940,000Listed For SalerealMLS #2074599
04/24/2025$1,940,000ListingRemovedrealMLS #2074599
03/08/2025$1,940,000Listed For SalerealMLS #2074599
12/07/2022$1,167,326Sold
N/A

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Property Tax and Assessment

Year2024
Tax$16,084
Assessment$846,497
Home facts updated by county records

Comparable Sales for 367 FIVE ISLAND Drive

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
354 Five Island Dr, Saint Augustine, FL
0.04
Single-Family Home
$1,650,000
09/12/25
4
3.5
2,658
129 Saint Barts Ave, Saint Augustine, FL
0.18
Single-Family Home
$690,000
08/25/25
4
3
2,495
57 Guanahani Trl, Saint Augustine, FL
0.12
Single-Family Home
$738,675
03/27/26
4
3
2,500
148 ANCIENT ISLAND Drive, Saint Augustine, FL
0.12
Single-Family Home
$615,500
10/31/25
4
3
2,495
108 Fiddler Crab Ln, Saint Augustine, FL
0.46
Single-Family Home
$1,105,500
04/27/26
4
2.5
3,108
64 ST BARTS Avenue, Saint Augustine, FL
0.19
Single-Family Home
$615,000
04/24/26
3
2.5
2,327
5 Anastasia Lakes Dr, Saint Augustine, FL
0.53
Single-Family Home
$699,500
03/13/26
4
2.5
2,410
104 Fiddler Crab Ln, Saint Augustine, FL
0.46
Single-Family Home
$1,335,000
09/02/25
4
3.5
3,358
1536 San Rafael Way, Saint Augustine, FL
0.59
Single-Family Home
$795,000
06/09/25
3
2.5
2,598

Assigned Schools

These are the assigned schools for 367 FIVE ISLAND Drive.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Saint Augustine

At least 668 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 90 % Say car is needed

  • 79 % Say there's holiday spirit

  • 79 % Say yards are well-kept

  • 74 % Say people would walk alone at night

  • 73 % Say it's quiet

  • 69 % Say parking is easy

  • 68 % Say kids play outside

  • 64 % Say there are sidewalks

  • 63 % Say there's wildlife

  • 59 % Say neighbors are friendly

  • 55 % Say they plan to stay for at least 5 years

  • 53 % Say streets are well-lit

  • 40 % Say there are community events

  • 35 % Say it's walkable to restaurants

  • 31 % Say it's walkable to grocery stores

Learn more about our methodology.
  • Trulia User
    "My neighborhood is attractive and peaceful. It’s green and full of unique houses and friendly people. The only problem is that the traffic is loud and too fast. "
    0
    Flag
  • Trulia User
    "There are nice decorations for each holiday. Other than that it’s just a friendly neighborhood and everyone is friendly and nice. "
    0
    Flag
  • Xavier.rivera11
    "Its very safe. I like it a lot. A lot of families and friendly people. I feel that the area is growing and still needs more activities in the amenity to have a better community "
    1
    Flag
  • Tiffany Villano
    "It’s a great community. Lots of kids and amenities Both close to Jacksonville downtown and Saint Augustine Lots of shopping food commercial lots of restaurants"
    0
    Flag
  • Ilester1862
    "I’ve lived in this neighborhood for over 5 years and love it. Neighbors are great and care for their homes. Very active community. Feel safe."
    1
    Flag
  • Tiffany Villano
    "Schools are decent. Lots to do every where even though people complain that there isnt. There’s more infrastructure to come in the next couple years. Overall quiet calm communities working families Love it here "
    0
    Flag
  • Gregory McCain
    "Lots of space for walking dogs in natural surroundings including small lakes and ponds. Almost everyone uses a leash when walking their dog."
    0
    Flag
  • Trulia User
    "Fish market, veggie stand and a historical park all in walking very short distance and no HOA, intercoastal is right here too"
    0
    Flag
  • Connie Worley
    "It is quiet and off the main road. Neighbors are friendly and polite. There is a good mixture of families, middle aged and retirees. The neighborhood borders a state preserve, so no development will be allowed to the east. It’s only a ten minute drive to the beach."
    0
    Flag
  • Evan Martinez
    "It is a kid friendly neighborhood, the can play unsupervised in culdasac and neighbors watch out for them "
    0
    Flag
  • Qgsdn2x7dk
    " Nice it’s really nice to live here and grow up here very kid friendly and great for walks I love it here"
    0
    Flag
  • Lesley Plott
    "The neighborhood is car dependent but public transportation is easily accessible. The area is growing rapidly."
    0
    Flag
  • kathyafleming
    "From here it’s walkable to work eats and downtown. All the sites are within walking distance. It’s a great community for walking. There is a drawbridge off the island so traffic can back up but it clears fast. It’s a slower pace. "
    0
    Flag
  • 66alice69
    "Busy on week days commute times morning and But easy travel mid day and also weekends best on Sunday"
    0
    Flag
  • Syn2267
    "Having a Friendly dog and pick up after your dog. Master should be able to tame their dog. Not curbing your dog. "
    0
    Flag
  • Nichols
    "We have lived in our neighborhood for four years. Everything that we could want is only a 10 minute drive from us"
    0
    Flag
  • Randi Simmons
    "Trailmark is a family friendly Neighborhood and beautiful community. It is a gem of a place to live! "
    0
    Flag
  • stewart_mendenhall
    "We have many miles of walkways as well as a dog park. There are a lot of people that walk their dogs through our neighborhood and all seem very friendly for the most part. "
    0
    Flag
  • kathyafleming
    "St augustine is growing rapidly. Sometime you wait 15 or 20 minutes in traffic to get downtown. It’s friendly but be prepared to have ups and downs in traffic if you are carting children to snd from activities. "
    0
    Flag
  • Trulia User
    "Principals in downtown is shady af. Staff is smug. No counselors so be mindful of how the school handles students mental health."
    0
    Flag
  • kathyafleming
    "You can walk downtown or to restaurants and brewery’s on the boulevard. It’s got wide quiet residential streets and beautiful trees. People are friendly and everyone knows everyone else. There are amazing landmarks near by, a marina, the lighthouse and the Castillo. "
    0
    Flag
  • kathyafleming
    "Driving is easy but crowded during tourist season. Mornings are generally not bad at all. At 5 pm commute may be crowded x "
    0
    Flag
  • Elizabeth Skidmore
    "There aren’t any open areas to walk with your dog and the community areas do not have doggie bags or disposal areas. Also many of the neighbors post signs that are not dog friendly, even for something as harmless as walking on their grass "
    30
    Flag
  • Renee Hulse
    "Old town USA. You can fish, kayak, hike and swim. The amenities are wonderful and the neighbors are even better"
    6
    Flag
  • Xtxp5qb76x
    "No side walks to scoot around, not many activities organised by the county, libraries don’t offer as much for kids as other states. Even thought great place to raise a family "
    9
    Flag
  • Sabena H.
    "No public transportation. Still a little remote, but is building quickly. Bartram Trail School district."
    2
    Flag
  • Vicki.perry
    "Great for families. Palencia has an elementary school in the community. Lots of places to ride your bike and take walks too."
    4
    Flag
  • Adrianna H.
    "There is No dog park. Which would be nice. But plenty of walk ways and trails to walk. Most of the dogs are very friendly. "
    9
    Flag
  • Peter T.
    "Nice place to live many people very friendly it’s hot though bring sun screen and water but also bug spray because mosquitos are a plenty "
    4
    Flag
  • Adrianna H.
    "Every Friday is Food Truck Friday up at the amenity center. Also kids sporting events and certain holiday activities as well. "
    0
    Flag
  • Srrossi
    "Quiet. Plenty of Law Enforcement in the neighborhood. I trust my neighbors. I enjoy my 2 mile walk through our neighborhood."
    0
    Flag
  • Sarah K.
    "This town is growing as a dog friendly area. There is a lot of neighborhoods and local businesses that allow dogs. Most people are super excited to great your and your pup. "
    1
    Flag
  • Candice S.
    "Christmas stroll and lights display make this town special. Small town feel, fabulous food. History makes this place special."
    1
    Flag
  • Kristen K.
    "You need transportation for this community. There is no public transportation. You average about 30 minutes from most places ."
    0
    Flag
  • Richard D.
    "There are a lot of them in the neighborhood. Many people own dogs, but it is important to pick up after pets and not let them run wild."
    1
    Flag
  • Egbacro
    "Epic theatre is close by, and downtown is about a 10min drive. The beach is located in Anastasia Island which has a lot of activities. the Lighthouse is nearby, and Saint Augustine’s beach is through the 312 bridge. There is an Amphitheatre close by which has many local and international events. Loads of restaurants, wine tasting and bars, shops/boutiques, museums including the Fountain of youth ca be visited."
    1
    Flag
  • Tkendall344
    "Always an event. St Augustine people care regardless if they know you or not the community always come together during crisis or when someone need assistance. We are St. Augustine Strong"
    0
    Flag
  • Terri.degrande
    "No specific events. It’s just a nice, established, well-maintained neighborhood with a cheap home owners association that really is functional, and neighbors are friendly and range widely in age. There’s tons of sidewalks, parks, ponds, wildlife, and very easy access to all types of stores and restaurants. "
    1
    Flag
  • Melvinemccall
    "Neighbors watch out for each other and are always ready to help. Cookouts about twice a year in the neighborhood open to all "
    0
    Flag
  • Jacqueline
    "We do not have many events in our neighborhood we only have quarterly yard sales. The neighbors are friendly and the neighborhood is beautiful."
    0
    Flag

LGBTQ Local Legal Protections

Beatrice Bredeson, MOMENTUM REALTY, (904) 903-1558
Agent Phone: (847) 648-0626
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by realMLS.
367 FIVE ISLAND Drive, Saint Augustine, FL 32080 is a 4 bedroom, 3 bathroom, 2,627 sqft single-family home built in 2022. This property is currently available for sale and was listed by realMLS on Feb 2, 2026. The MLS # for this home is MLS# 2128125.