957 Windward Way, Saint Augustine, FL 32080
Property image
Property image
OFF MARKET

$458,000

Trulia Estimate
as of Nov 7, 2026
  • 3 Beds
  • 2 Baths
  • 1,580 sqft

957 Windward Way, Saint Augustine, FL 32080

Home Highlights

Single-Family Home
Built in 2002
1,580 sqft
$290/sqft
Garage

Local Information

  • Map ViewExplore the area around 957 Windward Way.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Two-car garageTwo bathroomsOpen floor planWasher and dryer hookupsSpacious primary suiteVaulted ceilings
Welcome to your new home in the desirable Commodores Club community on Anastasia Island, just one mile from beautiful St. Augustine Beach. This charming single-family block home features a split floor plan with three spacious bedrooms and two bathrooms, offering comfort and privacy. The open floor plan includes vaulted ceilings and a screened porch overlooking a pond, creating a relaxing space to enjoy the Florida lifestyle. The home features a combination of tile and brand-new vinyl plank flooring throughout for a fresh, modern look and easy maintenance. The galley-style kitchen includes a pantry and eat-in area for casual dining, along with a separate dining area for more formal meals. The spacious primary suite features a generous walk-in closet and a bathroom with dual sinks. Additional features include a two-car garage and washer and dryer hookups. Lawn care and HOA fees are included in the rent, allowing you to enjoy the well-maintained community without the hassle. Commodores Club offers a variety of amenities, including a 30' x 50' swimming pool, pavilion with summer kitchen and restrooms, tennis and basketball courts, playground, and multiple lakes with fountains. With its convenient location near the beach and local attractions, this home offers an excellent opportunity to enjoy comfortable island living. Qualified, long-term tenants receive the first month's rent FREE! Call the office for details and qualifications. $100 application fee per adult. Second month's rent and security deposit are due at lease signing.
957 Windward Way, Saint Augustine, FL 32080 is a 3 bedroom, 2 bathroom, 1,580 sqft single-family home built in 2002. It last sold for $182,200 on May 1, 2002 (6,237% above the $2,875 asking price). More recently, it was listed as a rental in October 2026 with an asking price of $2,875 per month. That rental listing was removed on October 20, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $458,000, with a rent estimate of $2,682/month.

Home Details for 957 Windward Way

Interior Features

Heating & Cooling
Heating: Central, ElectricAir ConditioningCooling System: Air Conditioner, Central Air, ElectricHeating Fuel: Central
Levels, Entrance, & Accessibility
Stories: 1
Appliances & Utilities
DishwasherRefrigeratorWasher

Property Information

Year Built
Year Built: 2002
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Long Term

Exterior Features

Pool
Pool
Parking & Garage
GarageParking: Garage, On Site

Additional Information

Tennis Court(s)

Comparable Sales for 957 Windward Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
980 Windward Way, Saint Augustine, FL
0.06
Single-Family Home
$390,000
11/21/25
3
2
1,512 sqft
1109 Compass Row, Saint Augustine, FL
0.12
Single-Family Home
$450,000
12/30/25
3
2
1,580 sqft
1300 FLAGSHIP Court, Saint Augustine, FL
0.12
Single-Family Home
$436,000
03/20/26
3
2
1,580 sqft
1121 Compass Row, Saint Augustine, FL
0.10
Single-Family Home
$435,000
05/08/26
3
2
1,443 sqft
2372 Commodores Club Blvd, Saint Augustine, FL
0.14
Single-Family Home
$405,000
12/19/25
3
2
1,656 sqft
1116 Compass Row, Saint Augustine, FL
0.08
Single-Family Home
$539,900
02/13/26
3
2
1,580 sqft
1021 Windward Way, Saint Augustine, FL
0.09
Single-Family Home
$496,000
01/29/26
3
2
1,512 sqft
1013 Windward Way, Saint Augustine, FL
0.08
Single-Family Home
$485,000
07/31/26
3
2
1,781 sqft
1301 FLAGSHIP Court, Saint Augustine, FL
0.10
Single-Family Home
$480,000
08/31/26
3
2
1,796 sqft
116 Tidal Ln, Saint Augustine, FL
0.11
Single-Family Home
$515,000
12/12/25
3
2
1,540 sqft

Nearby homes

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Price and Tax history

DateEventPrice
Oct 20, 2026
Source: St Augustine St Johns County BOR #263176
ListingRemoved
$2,875
Oct 13, 2026
Source: St Augustine St Johns County BOR #263176
Listed For Rent
$2,875
Oct 12, 2026
Source: Zillow Rentals
ListingRemoved
$2,700
Oct 7, 2026
Source: Zillow Rentals
PriceChange
$2,700
Price decreased by 6%
Sep 21, 2026
Source: Zillow Rentals
PriceChange
$2,875
Price decreased by 3%

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
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  • 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
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  • 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
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  • 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
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  • Lesley Plott
    "The neighborhood is car dependent but public transportation is easily accessible. The area is growing rapidly."
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • Srrossi
    "Quiet. Plenty of Law Enforcement in the neighborhood. I trust my neighbors. I enjoy my 2 mile walk through our neighborhood."
    0
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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LGBTQ Local Legal Protections

Frequently asked questions about 957 Windward Way

  • What is 957 Windward Way estimated to be worth?
    Trulia's estimated value for 957 Windward Way in Saint Augustine, FL is $458,000.
  • What is the price history for 957 Windward Way?
    957 Windward Way in Saint Augustine, FL last sold for $182,200 in May 2002.
  • 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 $434K. That is up $5K from the prior month.
  • Does 957 Windward Way have air conditioning?
    Yes, 957 Windward Way in Saint Augustine, FL has air conditioning.
  • Does 957 Windward Way have a pool?
    Yes, 957 Windward Way in Saint Augustine, FL has a pool.

Homes for rent near 957 Windward Way

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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