1066 Cheyenne Dr, St Augustine, FL 32086
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Property image
OFF MARKET

1066 Cheyenne Dr
St Augustine, FL 32086

  • 4 Beds
  • 2 Baths
  • 2,282 sqft (on 0.78 acres)

$481,800

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $3,058/mo*
Refinance Your Home

$481,800

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $3,058/mo*
Refinance Your Home
4 Beds
2 Baths
2,282 sqft
(on 0.78 acres)

Home Value

Trulia Estimate
$482K
Since last month
Increased$1K (+0.3%)
Since last year
Increased$10K (+2.1%)
Since last sale
Increased$276K (+134.8%)
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 +102% in the last 10 years
MonthEstimated value
2026
August 2026$481K
July 2026$481K
June 2026$480K
May 2026$479K
April 2026$477K
March 2026$473K
February 2026$472K
January 2026$463K
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
901 Delcie Dr, Saint Augustine, FL
0.36
Single-Family Home
$170,000
08/22/25
4
2
1,797
217 S SHADOWWOOD Drive, Saint Augustine, FL
0.23
Single-Family Home
$700,000
07/14/26
3
2
2,067
3640 FORT PEYTON Circle, Saint Augustine, FL
0.34
Single-Family Home
$223,300
01/02/26
3
2
1,381
324 N Shadowwood Dr, Saint Augustine, FL
0.42
Single-Family Home
$545,000
05/08/26
4
2
2,067
3589 RED CLOUD Trail, Saint Augustine, FL
0.43
Single-Family Home
$545,000
02/05/26
3
2
1,972
200 S SHADOWWOOD Drive, Saint Augustine, FL
0.31
Single-Family Home
$625,000
05/22/26
3
2.5
2,256
3776 ARROWHEAD Drive, Saint Augustine, FL
0.11
Single-Family Home
$675,000
01/07/26
6
4
3,231
1212 Fort Peyton Dr, Saint Augustine, FL
0.37
Single-Family Home
$409,000
09/15/25
3
2
1,233
3644 Fort Peyton Cir, Saint Augustine, FL
0.37
Single-Family Home
$265,000
10/03/25
2
2
996
4109 Pine Run Cir, Saint Augustine, FL
0.62
Single-Family Home
$375,000
02/26/26
2
2
2,320

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
1060 CHEYENNE Drive, Saint Augustine, FL 32086
0.03
$704,500
4
2.5
2,560
Off Market
1084 Cheyenne Dr, Saint Augustine, FL 32086
0.06
$427,200
3
2
2,237
Off Market
3765 Arrowhead Dr, Saint Augustine, FL 32086
0.08
$522,300
3
2
1,842
Off Market
1030 CHEYENNE Drive, Saint Augustine, FL 32086
0.13
$175,000
-
-
-
For Sale
1191 Brookside Ct, Saint Augustine, FL 32086
0.13
$799,000
4
2.5
2,884
For Sale
3757 Arrowhead Dr, Saint Augustine, FL 32086
0.12
$539,100
3
2
2,094
Off Market
3776 ARROWHEAD Drive, Saint Augustine, FL 32086
0.11
$675,000
6
4
3,231
Recently Sold
113 Woodcutters Trl, Saint Augustine, FL 32086
0.18
$601,700
4
2
2,175
Off Market
3788 Arrowhead Dr, Saint Augustine, FL 32086
0.13
$444,000
3
2
1,842
Off Market
1030 Winterhawk Dr, Saint Augustine, FL 32086
0.19
$405,500
4
2
1,476
Off Market
217 S SHADOWWOOD Drive, Saint Augustine, FL 32086
0.23
$700,000
3
2
2,067
Recently Sold
101 WOODCUTTERS Trail, Saint Augustine, FL 32086
0.24
$814,900
4
3
2,892
Off Market

Local Information

  • Map ViewExplore the area around 1066 Cheyenne Dr.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1990
Lot Size
0.78 acres
Living Area
2,282 sqft
Price/Sqft
$211
Parking
Garage

About this House

GREAT LOCATION WITH YOUR OWN PRIVATE WOODS AND CREEK IN THE REAR. 3/4 ACRE WITH VERY TALL WINDOWS TO GIVE STUNNING VIEWS OF THE WOODS FROM THE LARGE GREAT ROOM. GREAT FOR ENTERTAINING.SELLER AND AGENT MAKE NO REPRESENTATIONS OR WARRANTIES, UNAWARE OF ANY DEFECTS OR LEAD BASED PAINTS. BEING SOLD ''AS IS''. ALL INFO TO BE VERIFIED BY BUYER. PROOF OF FUNDS
1066 Cheyenne Dr, St Augustine, FL 32086 is a 4 bedroom, 2 bathroom, 2,282 sqft single-family home built in 1990. It last sold for $205,000 on Nov 4, 2013. It is currently off market. The Trulia Estimate is $481,800, with a rent estimate of $2,643/month.

Home Details for 1066 Cheyenne Dr

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2Floors: Other, Carpet
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Stucco, WoodFoundation Type: Concrete
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1990Year Updated: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.78 acres

Price and Tax history

DateEventPrice
Nov 4, 2013
Source: N/A
Sold
$205,000
Aug 21, 2013
Source: realMLS #660621
Sold
$118,000
Jul 21, 2013
Source: Agent Provided
PriceChange
$124,900
Price decreased by 7%
Jun 26, 2013
Source: Agent Provided
PriceChange
$134,900
Price decreased by 7%
May 29, 2013
Source: Agent Provided
PriceChange
$144,900
Price decreased by 6%

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
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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 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
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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
    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
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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
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  • 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
  • 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
  • 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
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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
    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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Homes for sale near 1066 Cheyenne Dr

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Off Market Homes Near 1066 Cheyenne Dr

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Frequently asked questions about 1066 Cheyenne Dr

  • What is 1066 Cheyenne Dr estimated to be worth?
    Trulia's estimated value for 1066 Cheyenne Dr in St Augustine, FL is $481,800.
  • What is the price history for 1066 Cheyenne Dr?
    1066 Cheyenne Dr in St Augustine, FL last sold for $205,000 in November 2013.
  • Is St Augustine a buyer's or seller's market?
    St Augustine is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in St Augustine?
    The median sale price in St Augustine is $432K. That is up $13.33K from the prior month.
  • Does 1066 Cheyenne Dr have air conditioning?
    Yes, 1066 Cheyenne Dr in St Augustine, FL has air conditioning.
  • How big is the lot at 1066 Cheyenne Dr?
    The lot at 1066 Cheyenne Dr in St Augustine, FL is about 0.78 acres (33,976 sq ft).