27 Hildreth Dr, Saint Augustine, FL 32084
OFF MARKET

27 Hildreth Dr
Saint Augustine, FL 32084

  • 3 Beds
  • 2 Baths
  • 1,676 sqft

$577,500

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $3,505/mo*
Refinance Your Home

$577,500

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $3,505/mo*
Refinance Your Home
3 Beds
2 Baths
1,676 sqft

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Local Information

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

Description

This Mediterranean Revival is arguably one of the finest examples of the era in North City. The handhewn cypress beams were taken from an historic residence that had belonged to Captain John Masters. This home has undergone two major renovations, the last being completed by the current owner. Perfect inside and out, the private yard is perpetually green and shady so you can enjoy the patios year round. Some notice is required - please call Irene at 669.0691 for an appointment.


Marketing: Constructed some time between 1924 and 1930, the original owner was also the builder and an article that appeared in the St Augustine Record on July 4th, 1937 talked about the "great beams 83 feet long from the Old Captain John Masters house, said to have been the first house built north of the City Gates, which are now seen in the home Lee Sink built for himself in Fullerwood." These beautiful handhewn cypress beams still adorn the living room and set the tone for the rest of the house.

Pecky cypress doors open from the front porch into both the living and dining rooms. The fireplace is flanked by two casement windows as was the style in the 1920s - set high, they invite the light without compromising privacy. Three large windows overlook the street through a screen of landscaping. At the center of the house is a wonderful kitchen with ample room for cooking, consulting and kibitzing around the bar. Fully equipped, including a wine chiller, the finishes here are lovely and the flow to the living and dining rooms is easy. The guest rooms and hall bath are just off the kitchen. Comfortable and sunny, one is currently used as an office.

At the back of the house, the en-suite master will wrap its arms around you. Measuring 17' x 16', the room is spacious enough for an entire wall of shelves with a comfortable sitting area, a wall span perfect for a private media center across from the natural place to put your bed. A soaking tub with separate shower is all done in neutral earth tones and the walk-in closet is worthy of mention for its custom built-ins.

A 16' x 10' screened porch under a beamed ceiling is a wonderful outdoor gathering room and the deep eaves will keep you dry and comfortable even if it's raining. Fully fenced and decorated with bamboo, graceful palms and split-leaf philodendrons, the backyard is an oasis of green with two wooden decks connected by a wooden pathway. There's a covered 'bike and kayak' port on the west side of the property for your outdoor gear and the fence will keep the pups secure. It's a one-of-a-kind home in a one-of-a-kind city - come see for yourself.



This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
Porch, Patio, Deck
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 27 Hildreth Dr

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Interior Details
Ceiling Fan

Exterior Features

Exterior Home Features
Roof: Built UpDeckExterior: Stucco, WoodFoundation Type: ConcreteGardenPatioPorch
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1926Year Updated: 2001
Property Type / Style
Property Type: Single Family HomeArchitecture: Spanish

Community

Units in Building: 1

Lot Information

Lot Area: 6534 sqft

Price History for 27 Hildreth Dr

DatePriceEventSource
11/04/2011$290,000Sold
N/A
06/28/2011$299,000PriceChange
Agent Provided
03/11/2011$324,000PriceChange
Agent Provided
10/01/2010$369,000Listed For SaleAgent Provided
05/03/2005$399,000Sold
N/A
09/05/2003$142,500Sold
N/A
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Property Tax and Assessment

Year2024
Tax$8,561
Assessment$449,849
Home facts updated by county records

Comparable Sales for 27 Hildreth Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5 Atlantic Ave, Saint Augustine, FL
0.12
Single-Family Home
$365,000
07/22/25
3
2
1,427
57 Fullerwood Dr, Saint Augustine, FL
0.27
Single-Family Home
$310,000
04/10/26
2
2
1,383
14 Sylvan Dr, Saint Augustine, FL
0.10
Single-Family Home
$499,000
05/29/25
2
2
1,099
35 Oak St, Saint Augustine, FL
0.16
Single-Family Home
$660,000
03/13/26
3
2
2,082
25 FULLERWOOD Drive, Saint Augustine, FL
0.23
Single-Family Home
$560,000
12/29/25
3
2
1,344
6 E Park Ave, Saint Augustine, FL
0.12
Single-Family Home
$700,000
03/13/26
3
2.5
1,833
30 Macaris St, Saint Augustine, FL
0.25
Single-Family Home
$375,000
07/24/25
3
2.5
1,344
36 FULLERWOOD Drive, Saint Augustine, FL
0.20
Single-Family Home
$695,000
11/13/25
3
3
1,650
4 Court Louise, Saint Augustine, FL
0.17
Single-Family Home
$226,000
02/23/26
3
1
1,416
37 Oak St, Saint Augustine, FL
0.17
Single-Family Home
$630,000
06/20/25
3
2.5
2,418

Assigned Schools

These are the assigned schools for 27 Hildreth Dr.
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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. "
    1
    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

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Homes for rent near 27 Hildreth Dr

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Off Market Homes Near 27 Hildreth Dr

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27 Hildreth Dr, Saint Augustine, FL 32084 is a 3 bedroom, 2 bathroom, 1,676 sqft single-family home built in 1926. This property is not currently available for sale. 27 Hildreth Dr was last sold on Nov 4, 2011 for $290,000. The current Trulia Estimate for 27 Hildreth Dr is $577,500.