301 Winding Oak Way, Saint Augustine, FL 32084
Property image
Property image
OFF MARKET

$437,000

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,978 sqft

301 Winding Oak Way, Saint Augustine, FL 32084

Est. Refi. Payment $2,822/mo*
Refinance Your Home
Currently Off Market - Sold Nov 4, 2022 for $458,000

Home Value

Trulia Estimate
$437K
Since last month
Increased$700 (+0.2%)
Since last year
Decreased$6K (-1.4%)
Since last sale
Decreased$21K (-4.5%)
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 +75% in the last 10 years
MonthEstimated value
2026
August 2026$438K
August 2026$437K
July 2026$437K
June 2026$443K
May 2026$443K
April 2026$446K
March 2026$442K
February 2026$444K
January 2026$441K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
308 WINDING OAK Way, Saint Augustine, FL
0.04
Single-Family Home
$370,000
12/10/25
4
2
2,091
271 ROARING BROOK Drive, Saint Augustine, FL
0.29
Single-Family Home
$425,000
09/12/25
3
2
1,838
96 CYPRESS BLUFF Way, Saint Augustine, FL
0.32
Single-Family Home
$465,000
03/27/26
3
2
2,066
266 Roaring Brook Dr, Saint Augustine, FL
0.28
Single-Family Home
$520,000
03/02/26
4
2
1,800
367 MISSION TRACE Drive, Saint Augustine, FL
0.42
Single-Family Home
$540,000
06/10/26
3
2
1,906
119 MISSION TRACE Drive, Saint Augustine, FL
0.50
Single-Family Home
$389,500
03/18/26
3
2
2,139
775 Blackmoor Gate Ln, Saint Augustine, FL
0.63
Single-Family Home
$473,500
10/30/25
3
2
1,868
526 Montiano Cir, Saint Augustine, FL
0.54
Single-Family Home
$600,900
10/20/25
3
2
1,984
49 MISSION COVE Circle, Saint Augustine, FL
0.44
Single-Family Home
$362,000
05/29/26
4
2
2,126
486 Hefferon Dr, Saint Augustine, FL
0.51
Single-Family Home
$401,000
03/20/26
4
2
2,050

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
305 WINDING OAK WAY, Saint Augustine, FL 32084
0.02
$436,700
4
3.5
2,594
Off Market
308 WINDING OAK Way, Saint Augustine, FL 32084
0.04
$370,000
4
2
2,091
Recently Sold
113 Grafft Ln, Saint Augustine, FL 32084
0.04
$608,000
3
3
2,806
Off Market
125 GRAFFT Lane, Saint Augustine, FL 32084
0.01
$526,900
4
2
2,091
Off Market
141 Grafft Ln, Saint Augustine, FL 32084
0.07
$499,900
3
2
1,858
For Sale
140 Grafft Ln, Saint Augustine, FL 32084
0.08
$433,000
4
3
2,056
Off Market
209 Roaring Brook Dr, Saint Augustine, FL 32084
0.08
$476,900
3
3
2,770
Off Market
1770 Woodlawn Rd, Saint Augustine, FL 32084
0.18
$1,200,000
-
-
-
For Sale
940 STATE ROAD 16, Saint Augustine, FL 32084
0.17
-
-
-
-
Off Market
930 State Road 16 St, Saint Augustine, FL 32084
0.17
$2,100,000
-
-
-
For Sale
262 Roaring Brook Dr, Saint Augustine, FL 32084
0.27
$491,000
4
2.5
3,037
Off Market
804 Oakland Ave, Saint Augustine, FL 32084
0.33
$263,200
3
2.5
1,297
Off Market

Local Information

  • Map ViewExplore the area around 301 Winding Oak Way.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2015
1,978 sqft
$221/sqft
Garage

About this House

Coastal contemporary single-story home built in 2015 w/3-car garage on quiet cul-de-sac in charming Olde Florida. Open plan w/vaulted ceilings & formal dining room that could be converted to an office or den. Gourmet kitchen w/spacious island, granite countertops, 42" upper cabinets, tile floor, & stainless appliances. Owners suite includes French door to screened lanai, large walk-in closet, dual vanities, garden tub, & roomy tiled shower. Private mostly-fenced yard; low HOA only $215/quarter.
301 Winding Oak Way, Saint Augustine, FL 32084 is a 3 bedroom, 2 bathroom, 1,978 sqft single-family home built in 2015. It last sold for $458,000 on Nov 4, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $437,000, with a rent estimate of $2,268/month.

Home Details for 301 Winding Oak Way

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
Types of Rooms: Walk In Closet, Dining RoomCeiling Fan
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: StuccoFoundation Type: ConcretePorch
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2015
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 9583 sqft

Price and Tax history

DateEventPrice
Nov 4, 2022
Source: N/A
Sold
$458,000
Jun 28, 2022
Source: N/A
Sold
$440,900
Apr 15, 2020
Source: Agent Provided
ListingRemoved
$284,900
Apr 15, 2020
Source: Agent Provided
Listed For Sale
$284,900
Apr 14, 2020
Source: realMLS #1020121
Sold
$279,000

Market trends in Saint Augustine

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$432K
$13.33KMoM
Sale-to-List Price
97.5%
0.3%MoM
Price per sq ft
$227
$1MoM
Available listings
1789
109MoM

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

Frequently asked questions about 301 Winding Oak Way

  • What is 301 Winding Oak Way estimated to be worth?
    Trulia's estimated value for 301 Winding Oak Way in Saint Augustine, FL is $437,000.
  • What is the price history for 301 Winding Oak Way?
    301 Winding Oak Way in Saint Augustine, FL last sold for $458,000 in November 2022.
  • 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 $432K. That is up $13.33K from the prior month.
  • Does 301 Winding Oak Way have air conditioning?
    Yes, 301 Winding Oak Way in Saint Augustine, FL has air conditioning.
  • Does 301 Winding Oak Way have laundry facilities?
    Yes, 301 Winding Oak Way in Saint Augustine, FL has in-unit laundry.

Explore by feature - Pet Friendly

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