27 Oak St, Saint Augustine, FL 32084
FOR SALE
3D VIEW

27 Oak St
Saint Augustine, FL 32084

  • 3 Beds
  • 2.5 Baths
  • 1,784 sqft

$575,000

Original price: $599,900
Est. Mortgage $3,517/mo*
Get Pre-Qualified

$575,000

Original price: $599,900
Est. Mortgage $3,517/mo*
Get Pre-Qualified
3 Beds
2.5 Baths
1,784 sqft

Local Information

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

Description

Tucked away on a quiet dead end street in the heart of Uptown St. Augustine, 27 Oak Street offers an incredible opportunity to enjoy marshfront living just minutes from the historic district and the beaches of Vilano. Located in the desirable Hildreth Back Bay section of Fullerwood Park and set at a high elevation, this 3 bedroom, 2.5 bath home captures the essence of peaceful coastal living while remaining close to everything that makes St. Augustine special. Inside, the home welcomes you with fresh new interior paint, warm travertine tile floors, and a bright open layout designed for both everyday comfort and entertaining. The kitchen has been beautifully refreshed with refinished cabinetry, granite countertops, and brand new appliances, creating a clean and functional space that flows seamlessly into the main living areas. Upstairs, the primary suite is perfectly positioned to take in the tranquil marsh backdrop and features its own private balcony, an ideal place to enjoy your morning coffee while watching the sunrise over the marsh or unwind in the evening as coastal breezes roll in. Two additional bedrooms provide comfortable accommodations for family or guests, while a separate flex space offers versatility for a home office, reading nook, playroom, or loft style lounge. Outside, the spacious homesite offers sweeping marsh views and a peaceful natural setting, often visited by native birds and wildlife. The property also offers a rare level of functionality with space to discreetly store an RV or boat completely tucked away from view. Additional highlights include a garage wired for an EV charger and thoughtful interior updates that make the home completely move in ready. Located within an A rated school district and just moments from Uptown’s beloved coffee shops, restaurants, and boutiques, this home blends lifestyle, flexibility, and location. With no HOA restrictions, owners have the freedom to enjoy the property as a primary residence, second home, or short term rental. Marsh views, privacy, modern updates, and a prime Uptown location make 27 Oak Street a rare opportunity to experience the best of St. Augustine living.

Home Highlights

Parking
Garage
Outdoor
No Info
View
Water
HOA
None
Price/Sqft
$322
Listed
64 days ago

Home Details for 27 Oak St

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Master Bedroom
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1784 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, WasherDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Electric,Fireplace(s)Has CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central
Fireplace & Spa
Has a Fireplace
Windows, Doors, Floors & Walls
Flooring: Tile
Levels, Entrance, & Accessibility
Stories: 2Levels: 2 Story, SplitEntry Location: Ground LevelFloors: Tile
View
Has a ViewView: Water

Exterior Features

Exterior Home Features
Roof: MetalFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageNo Attached GarageNo Open ParkingParking Spaces: 1Parking: 1 Car Garage
Frontage
WaterfrontWaterfront: Marsh Front, Waterfront, MarshOn Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Days on Market: 64

Property Information

Year Built
Year Built: 2015
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: FrameNot a New Construction
Property Information
Parcel Number: 1504800000

Price & Status

Price
List Price: $575,000Price Per Sqft: $322

Active Status

MLS Status: Active

Location

Direction & Address
City: St AugustineCommunity: Hildreth Back Bay
School Information
Elementary School: KetterlinusJr High / Middle School: SebastianHigh School: St. Augustine

Agent Information

Listing Agent
Listing ID: 261081

Building

Building Area
Building Area: 1784 Square Feet

HOA

No HOA

Lot Information

Lot Area: 7405.2 sqft

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Rental Terms, Policies & Fees

Lease Term: 1 Week

Miscellaneous

Mls Number: 261081Water ViewWater View: Marsh View, Water
Last check for updates: about 4 hours ago
Listing courtesy of Madison Beale, (904) 295-5150
MAXREV
Source: St Augustine St Johns County BOR, MLS#261081
Also Listed on St Augustine St Johns County BOR.

Price History for 27 Oak St

DatePriceEventSource
05/08/2026$575,000PriceChange
St Augustine St Johns County BOR #261081
04/24/2026$599,900PriceChange
St Augustine St Johns County BOR #261081
03/21/2026$649,000PriceChange
St Augustine St Johns County BOR #261081
03/06/2026$679,000Listed For SaleSt Augustine St Johns County BOR #261081
04/25/2025$600,000Sold
St Augustine St Johns County BOR #250330
03/27/2025$640,000PendingSt Augustine St Johns County BOR #250330
02/01/2025$640,000PriceChange
St Augustine St Johns County BOR #250330
01/17/2025$655,000Listed For SaleSt Augustine St Johns County BOR #250330
04/08/2015$317,100Sold
N/A
12/06/2012$69,000ListingRemovedAgent Provided
07/13/2012$50,000Sold
realMLS #615197
06/09/2012$69,000PendingAgent Provided
03/18/2012$69,000PriceChange
Agent Provided
07/01/2011$59,000PriceChange
Agent Provided
06/03/2011$69,000Listed For SaleAgent Provided

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Property Tax and Assessment

Year2024
Tax$4,695
Assessment$459,438
Home facts updated by county records

Comparable Sales for 27 Oak St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
35 Oak St, Saint Augustine, FL
0.03
Single-Family Home
$660,000
03/13/26
3
2
2,082
37 Oak St, Saint Augustine, FL
0.04
Single-Family Home
$630,000
06/20/25
3
2.5
2,418
6 E Park Ave, Saint Augustine, FL
0.20
Single-Family Home
$700,000
03/13/26
3
2.5
1,833
36 FULLERWOOD Drive, Saint Augustine, FL
0.32
Single-Family Home
$695,000
11/13/25
3
3
1,650
44 HILDRETH Way, Saint Augustine, FL
0.11
Single-Family Home
$605,000
10/20/25
4
3
1,856
22 Bay View Dr, Saint Augustine, FL
0.26
Single-Family Home
$655,000
10/10/25
4
2.5
1,783
44 Hildreth Dr, Saint Augustine, FL
0.11
Single-Family Home
$605,000
10/20/25
4
3
1,856
16 COURT THEOPHELIA, Saint Augustine, FL
0.16
Single-Family Home
$506,900
03/25/26
4
3
2,513

Assigned Schools

These are the assigned schools for 27 Oak St.
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

Madison Beale, MAXREV
Agent Phone: (904) 295-5150
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. Information is deemed reliable but not guaranteed. © 2026 St Augustine & St. Johns County Board of REALTORS®. All rights reserved.
27 Oak St, Saint Augustine, FL 32084 is a 3 bedroom, 3 bathroom, 1,784 sqft single-family home built in 2015. This property is currently available for sale and was listed by St Augustine St Johns County BOR on Mar 6, 2026. The MLS # for this home is MLS# 261081.