1557 W Windy Willow Dr, Saint Augustine, FL 32092
Property image
Property image
OFF MARKET

$394,700

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 1,750 sqft

1557 W Windy Willow Dr, Saint Augustine, FL 32092

Est. Refi. Payment $2,605/mo*
Refinance Your Home
Currently Off Market - Sold Aug 5, 2014 for $178,000

Home Value

Trulia Estimate
$395K
Since last month
$100 (0%)
Since last year
Increased$15K (+3.9%)
Since last sale
Increased$216K (+121.3%)
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
September 2026$394K
August 2026$394K
July 2026$399K
June 2026$393K
May 2026$390K
April 2026$393K
March 2026$389K
February 2026$391K
January 2026$386K
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
1564 W WINDY WILLOW Drive, Saint Augustine, FL
0.06
Single-Family Home
$400,000
04/29/26
4
2
1,886
1525 W Windy Willow Dr, Saint Augustine, FL
0.09
Single-Family Home
$440,750
11/24/25
4
2
2,005
1575 E WINDY WILLOW Drive, Saint Augustine, FL
0.10
Single-Family Home
$374,000
12/22/25
3
2
1,652
464 JOHNS CREEK Parkway, Saint Augustine, FL
0.16
Single-Family Home
$495,000
09/03/26
4
2
2,005
2110 THORN HOLLOW Court, Saint Augustine, FL
0.12
Single-Family Home
$480,000
04/10/26
4
2.5
2,867
1436 TINTERN Lane, Saint Augustine, FL
0.38
Single-Family Home
$426,000
06/08/26
4
2
1,935
1524 AUSTIN Lane, Saint Augustine, FL
0.39
Single-Family Home
$370,000
11/03/25
3
2
1,718
1051 GARRISON Drive, Saint Augustine, FL
0.29
Single-Family Home
$450,000
05/20/26
3
2
2,250
1624 AUSTIN Lane, Saint Augustine, FL
0.44
Single-Family Home
$469,900
05/28/26
3
2
1,762
1441 TINTERN Lane, Saint Augustine, FL
0.42
Single-Family Home
$420,000
06/15/26
3
2
1,772

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
1553 W WINDY WILLOW Drive, Saint Augustine, FL 32092
0.01
$437,200
4
2
2,005
Off Market
1549 W WINDY WILLOW Drive, Saint Augustine, FL 32092
0.03
$414,700
4
2
1,886
Off Market
2000 SPRING MEADOWS Court, Saint Augustine, FL 32092
0.07
$519,900
4
3
2,402
Off Market
1541 W WINDY WILLOW Drive, Saint Augustine, FL 32092
0.05
$380,500
3
2
2,070
Off Market
372 JOHNS CREEK Parkway, Saint Augustine, FL 32092
0.08
$417,500
3
2
1,862
Off Market
412 JOHNS CREEK Parkway, Saint Augustine, FL 32092
0.05
$389,600
4
2
1,673
Off Market
2020 Spring Meadows Ct, Saint Augustine, FL 32092
0.10
$423,900
4
2
2,038
Off Market
1564 W WINDY WILLOW Drive, Saint Augustine, FL 32092
0.06
$400,000
4
2
1,886
Recently Sold
2114 THORN HOLLOW Court, Saint Augustine, FL 32092
0.12
$529,900
5
4
3,072
Recently Sold
1525 W Windy Willow Dr, Saint Augustine, FL 32092
0.09
$440,750
4
2
2,005
Recently Sold
2110 THORN HOLLOW Court, Saint Augustine, FL 32092
0.12
$480,000
4
2.5
2,867
Recently Sold
1532 W WINDY WILLOW DRIVE, Saint Augustine, FL 32092
0.09
$380,500
3
2
1,630
Off Market

Local Information

  • Map ViewExplore the area around 1557 W Windy Willow Dr.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2004
1,750 sqft
$226/sqft
Garage

About this House

What's unique:Cozy fireplacePrivate backyardCovered patioSpacious bedroomsGorgeous natural lightingSmart home
This single-family home is located at 1557 W Windy Willow Dr, Saint Augustine, FL. 1557 W Windy Willow Dr is in Saint Augustine, FL and in ZIP code 32092. This property has 4 bedrooms, 2 bathrooms and approximately 1,750 sqft of floor space. This property has a lot size of 9600 sqft and was built in 2004.
1557 W Windy Willow Dr, Saint Augustine, FL 32092 is a 4 bedroom, 2 bathroom, 1,750 sqft single-family home built in 2004. It last sold for $178,000 on Aug 5, 2014. More recently, it was listed as a rental in June 2022 with an asking price of $2,365 per month. That rental listing was removed on June 4, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $394,700, with a rent estimate of $2,511/month.

Home Details for 1557 W Windy Willow Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Interior Details
Types of Rooms: Walk In Closet, Dining Room, Family Room, Master Bath
Heating & Cooling
Air Conditioning
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: BrickFoundation Type: Concrete
Parking & Garage
GarageParking: None, Garage

Property Information

Year Built
Year Built: 2004Year Updated: 2004
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 9600 sqft

Price and Tax history

DateEventPrice
Jun 4, 2022
Source: Zillow Rental Network Premium
ListingRemoved
Jun 3, 2022
Source: Zillow Rental Network Premium
Listed For Rent
$2,365
Oct 14, 2016
Source: Agent Provided
ListingRemoved
$1,635
Sep 14, 2014
Source: Agent Provided
ListingRemoved
$1,645
Aug 28, 2014
Source: Agent Provided
Listed For Rent
$1,645

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

Frequently asked questions about 1557 W Windy Willow Dr

  • What is 1557 W Windy Willow Dr estimated to be worth?
    Trulia's estimated value for 1557 W Windy Willow Dr in Saint Augustine, FL is $394,700.
  • What is the price history for 1557 W Windy Willow Dr?
    1557 W Windy Willow Dr in Saint Augustine, FL last sold for $178,000 in August 2014.
  • 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.
  • How big is the lot at 1557 W Windy Willow Dr?
    The lot at 1557 W Windy Willow Dr in Saint Augustine, FL is about 0.22 acres (9,600 sq ft).
  • Does 1557 W Windy Willow Dr have a garage?
    Yes, 1557 W Windy Willow Dr in Saint Augustine, FL has a garage.

Explore by feature - Pet Friendly

311 pet-friendly rentals in Saint Augustine, FL

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Apartments for Rent

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Off Market Homes Near 1557 W Windy Willow Dr

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