539 CHESTNUT OAK Road, Saint Augustine, FL 32092
SOLD
MAR 27, 2026

$1,721,700

Trulia Estimate
  • 4 Beds
  • 4.5 Baths
  • 3,492 sqft

539 CHESTNUT OAK Road, Saint Augustine, FL 32092

Est. Refi. Payment $11,202/mo*
Refinance Your Home
Currently Off Market - Sold Mar 27, 2026 for $1,707,107 (20% above list price)

Home Value

Trulia Estimate
$1.72M
Since last month
Decreased$3K (-0.1%)
Since last year
Increased$300K (+21.1%)
Since last sale
Increased$11K (+0.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +21% in the last 10 years
MonthEstimated value
2026
September 2026$1.72M
August 2026$1.72M
July 2026$1.72M
June 2026$1.71M
May 2026$1.71M
April 2026$1.71M
March 2026$1.71M
February 2026$1.42M
January 2026$1.42M
2025

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
407 BROOK RIDGE Way, Augustine, FL
0.00
Single-Family Home
$1,497,013
10/14/25
4
4.5
3,508
447 CHESTNUT OAK Road, Saint Augustine, FL
0.00
Single-Family Home
$1,640,293
06/09/26
4
4.5
4,067
419 BROOK RIDGE Way, Augustine, FL
0.00
Single-Family Home
$1,731,434
12/22/25
3
4
3,719
385 BROOK RIDGE Way, Augustine, FL
0.00
Single-Family Home
$1,240,819
12/12/25
4
4.5
3,829
607 CHESTNUT OAK Road, Saint Augustine, FL
0.00
Single-Family Home
$1,594,218
11/21/25
5
4.5
5,163
70 FOREST VALLEY Court, Augustine, FL
0.06
Single-Family Home
$1,666,909
12/19/25
4
5.5
4,739
357 BROOK RIDGE Way, Augustine, FL
0.00
Single-Family Home
$1,217,189
12/23/25
5
3.5
3,980
273 BROOK RIDGE Way, Augustine, FL
0.00
Single-Family Home
$1,501,138
05/28/26
5
5.5
4,413
71 FOREST VALLEY Court, Augustine, FL
0.00
Single-Family Home
$1,423,700
09/26/25
5
4.5
5,229

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
65 FOREST VALLEY Court, Augustine, FL 32092
0.00
$3,607,333
4
5
6,127
Recently Sold
612 CHESTNUT OAK Lane, Augustine, FL 32092
0.00
$1,905,300
5
5.5
4,749
Off Market
395 BROOK RIDGE Way, Augustine, FL 32092
0.00
$1,280,300
4
4
3,849
Off Market
407 BROOK RIDGE Way, Augustine, FL 32092
0.00
$1,514,600
4
4.5
3,508
Off Market
71 FOREST VALLEY Court, Augustine, FL 32092
0.00
$1,438,800
5
4.5
5,229
Off Market
515 BROOKE RIDGE Way, Augustine, FL 32092
0.00
$1,138,386
5
3.5
4,338
Recently Sold
607 CHESTNUT OAK Road, Saint Augustine, FL 32092
0.00
$1,619,800
5
4.5
5,163
Off Market
385 BROOK RIDGE Way, Augustine, FL 32092
0.00
$1,240,819
4
4.5
3,829
Recently Sold
357 BROOK RIDGE Way, Augustine, FL 32092
0.00
$1,217,189
5
3.5
3,980
Recently Sold
419 BROOK RIDGE Way, Augustine, FL 32092
0.00
$1,731,434
3
4
3,719
Recently Sold
613 CHESTNUT OAK Road, Saint Augustine, FL 32092
0.00
$1,694,466
7
6
5,753
Recently Sold
273 BROOK RIDGE Way, Augustine, FL 32092
0.00
$1,501,138
5
5.5
4,413
Recently Sold

Local Information

  • Map ViewExplore the area around 539 CHESTNUT OAK Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2025
3,492 sqft
$489/sqft
Garage
HOA $100/mo

About this House

What's unique:Thoughtful detailsFour bedroomsFour-car garageExpansive spaces
The Monica floor plan is a masterclass in modern luxury, blending expansive spaces with thoughtful details that make daily living a pleasure. Spanning an impressive 3,488 square feet, this one-story home offers four bedrooms, four and a half baths, and a four-car garage. Every corner of this home is designed for both comfort and sophistication, making it ideal for families who appreciate the finer things.
539 CHESTNUT OAK Road, Saint Augustine, FL 32092 is a 4 bedroom, 5 bathroom, 3,492 sqft single-family home built in 2025. It last sold for $1,707,107 on Mar 27, 2026 (20% above the $1,428,141 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,721,700, with a rent estimate of $5,445/month.
Last check for updates: about 2 hours ago
Listed by ALI KARGAR
ICI SELECT REALTY, INC., (386) 236-4220
Bought with: ALI KARGAR, ICI SELECT REALTY, INC.
Source: realMLS, MLS#2114158

Home Details for 539 CHESTNUT OAK Road

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Living Room, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3492 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Available, Natural Gas Available, Water AvailableAppliances: Dishwasher, Disposal, Gas Cooktop, Gas Water Heater, Tankless Water HeaterDishwasherDisposal
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Levels, Entrance, & Accessibility
Stories: 1Levels: One
View
No View

Exterior Features

Parking & Garage
Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageNo Attached GarageParking Spaces: 4Parking: Garage,Garage Door Opener
Frontage
Not on Waterfront

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: 0099830770

Price & Status

Price
List Price: $1,428,141Price Per Sqft: $489/sqft
Status Change & Dates
Off Market Date: Mon Oct 20 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: Closed

Location

Direction & Address
City: St. AugustineCommunity: Silverleaf
School Information
High School: Tocoi Creek

Community

Not Senior Community

HOA

HOA Fee (second): 650HOA Fee Frequency (second): AnnuallyHas an HOAHOA Fee: $1,200/Annually

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Miscellaneous

Mls Number: 2114158

Price and Tax history

DateEventPrice
Mar 27, 2026
Source: realMLS #2114158
Sold
$1,707,107
Oct 20, 2025
Source: realMLS #2114158
Pending
$1,428,141
Oct 20, 2025
Source: realMLS #2114158
Listed For Sale
$1,428,141

Market trends in Saint Augustine

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$429K
$2.5KMoM
Sale-to-List Price
97.4%
Price per sq ft
$228
$0MoM
Available listings
1730
61MoM

Around this home

What Locals Say about Saint Augustine

At least 670 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

  • 70 % Say parking is easy

  • 68 % Say kids play outside

  • 63 % Say there's wildlife

  • 63 % Say there are sidewalks

  • 60 % Say neighbors are friendly

  • 56 % 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
    "Great place to raise your family. The kids are kind and friendly and the schools are awesome! Plenty of community parks."
    0
    Flag
  • Trulia User
    "Great place to raise kids "
    0
    Flag
  • 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
  • Sabena H.
    "No public transportation. Still a little remote, but is building quickly. Bartram Trail School district."
    2
    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

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.

Frequently asked questions about 539 CHESTNUT OAK Road

  • What is 539 CHESTNUT OAK Road estimated to be worth?
    Trulia's estimated value for 539 CHESTNUT OAK Road in Saint Augustine, FL is $1,721,700.
  • What is the price history for 539 CHESTNUT OAK Road?
    539 CHESTNUT OAK Road in Saint Augustine, FL last sold for $1,707,107 in March 2026.
  • Is Saint Augustine a buyer's or seller's market?
    Saint Augustine is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Saint Augustine?
    The median sale price in Saint Augustine is $429K. That is down $2.5K from the prior month.
  • Does 539 CHESTNUT OAK Road have air conditioning?
    Yes, 539 CHESTNUT OAK Road in Saint Augustine, FL has air conditioning.
  • Does 539 CHESTNUT OAK Road have a garage?
    Yes, 539 CHESTNUT OAK Road in Saint Augustine, FL has a garage.

Explore by feature - Pet Friendly

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