365 CHESTNUT OAK Road, Saint Augustine, FL 32092
OFF MARKET

365 CHESTNUT OAK Road
Saint Augustine, FL 32092

  • 5 Beds
  • 4.5 Baths
  • 4,242 sqft

$1,156,200

Trulia Estimate
as of May 31, 2026
Est. Refi. Payment $7,038/mo*
Refinance Your Home

$1,156,200

Trulia Estimate
as of May 31, 2026
Est. Refi. Payment $7,038/mo*
Refinance Your Home
5 Beds
4.5 Baths
4,242 sqft

Local Information

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

Description

Introducing the Brooke, a spacious 3,610-square-foot home that's designed to fit modern lifestyles with style and ease. Featuring 5 bedrooms, 3.5 bathrooms, and a three-car garage, this two-story layout brings together open spaces, cozy nooks, and flexible areas for family gatherings, entertaining, and relaxation. With ICI Homes' attention to detail and customization options, the Brooke can truly be a home that fits your unique vision. The covered front entry leads into a welcoming foyer, with a nearby study that's perfect for a home office, library, or quiet retreat. As you continue, the open floor plan unfolds with a bright dining area that flows into the heart of the home. The gourmet kitchen features a deluxe layout, complete with an expansive island, high-end appliances, a large walk-in pantry, and a convenient pass-through to the laundry room and garage. This kitchen is ready for everything from quick family breakfasts to holiday feasts, with plenty of counter space.
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. This description is from September 24, 2025

Home Highlights

Parking
Garage
Outdoor
Porch, Patio
View
No Info
HOA
$100/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 365 CHESTNUT OAK Road

Active Status

MLS Status: Closed

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 4, Bedroom 5, Bathroom 3, Dining Room, Living Room, Loft, Office, Other
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4242 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Available, Natural Gas Available, Water AvailableAppliances: Dishwasher, Disposal, Gas Cooktop, Gas Water Heater, Tankless Water HeaterDishwasherDisposalLaundry: Electric Dryer Hookup,Gas Dryer Hookup,Washer Hookup
Heating & Cooling
Heating: ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 2Levels: One
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, Patio
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageNo Attached GarageParking Spaces: 3Parking: Garage Door Opener
Frontage
Road Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 2025
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Traditional
Building
Is a New ConstructionNot Attached Property
Property Information
Condition: Under ConstructionParcel Number: 0103600001

Price & Status

Price
List Price: $1,181,680
Status Change & Dates
Off Market Date: Mon Apr 07 2025Possession Timing: Close Of Escrow

Location

Direction & Address
City: St. AugustineCommunity: Silverleaf
School Information
Elementary School: Liberty Pines AcademyJr High / Middle School: Liberty Pines AcademyHigh School: Tocoi Creek

Community

Not Senior Community

HOA

HOA Name: John's IslandHOA Fee (second): 650HOA Fee Frequency (second): AnnuallyHas an HOAHOA Fee: $1,200/Annually

Offer

Listing Terms: Cash, FHA, VA Loan

Miscellaneous

Mls Number: 2089948

Additional Information

HOA Amenities: Pool,Dog Park,Gated,Park,Pickleball,Playground,Tennis Court(s)
Last check for updates: about 2 hours ago
Listed by ALI KARGAR
ICI SELECT REALTY, INC., (386) 236-4220
Bought with: FLORIDA HOMES REALTY & MTG LLC, (904) 996-9115
Source: realMLS, MLS#2089948

Price History for 365 CHESTNUT OAK Road

DatePriceEventSource
04/07/2025$1,181,680Sold
realMLS #2089948
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Comparable Sales for 365 CHESTNUT OAK Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
44 GLENBRIAR Court, Augustine, FL
0.00
Single-Family Home
$1,103,164
08/14/25
5
3.5
3,825
74 GLENBRIAR Court, Augustine, FL
0.00
Single-Family Home
$1,209,333
10/10/25
4
4
3,536
281 CHESTNUT OAK Road, Saint Augustine, FL
0.17
Single-Family Home
$1,131,141
02/27/26
5
3.5
3,973
95 CHESTNUT OAK Road, Saint Augustine, FL
0.17
Single-Family Home
$1,471,071
02/24/26
5
3.5
4,198
515 BROOKE RIDGE Way, Augustine, FL
0.24
Single-Family Home
$1,138,386
12/15/25
5
3.5
4,338
357 BROOK RIDGE Way, Augustine, FL
0.24
Single-Family Home
$1,217,189
12/23/25
5
3.5
3,980
153 BROOK RIDGE Way, Saint Augustine, FL
0.17
Single-Family Home
$1,408,870
06/13/25
5
5
5,051
271 CHESTNUT OAK Road, Saint Augustine, FL
0.17
Single-Family Home
$963,905
12/10/25
5
4
3,058
83 CHESTNUT OAK Road, Saint Augustine, FL
0.17
Single-Family Home
$1,187,510
09/22/25
3
3.5
3,984
385 BROOK RIDGE Way, Augustine, FL
0.24
Single-Family Home
$1,240,819
12/12/25
4
4.5
3,829

Nearby homes

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Assigned Schools

These are the assigned schools for 365 CHESTNUT OAK Road.
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 669 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 90 % Say car is needed

  • 79 % Say yards are well-kept

  • 79 % Say there's holiday spirit

  • 74 % Say it's quiet

  • 74 % Say people would walk alone at night

  • 69 % Say parking is easy

  • 68 % Say kids play outside

  • 63 % Say there's wildlife

  • 63 % Say there are sidewalks

  • 60 % 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

Sourced by Trulia users. 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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Apartments for Rent

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Homes for sale near 365 CHESTNUT OAK Road

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Off Market Homes Near 365 CHESTNUT OAK Road

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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.

Homes for rent near 365 CHESTNUT OAK Road

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365 CHESTNUT OAK Road, Saint Augustine, FL 32092 is a 5 bedroom, 5 bathroom, 4,242 sqft single-family home built in 2025. This property is not currently available for sale. 365 CHESTNUT OAK Road was last sold on Apr 7, 2025 for $1,181,680 (0% higher than the asking price of $1,181,680). The current Trulia Estimate for 365 CHESTNUT OAK Road is $1,156,200.