27 Madeira Dr, Saint Augustine, FL 32080
Property image
Property image
OFF MARKET

27 Madeira Dr
Saint Augustine, FL 32080

  • 2 Beds
  • 2 Baths
  • 1,573 sqft

$477,300

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $3,035/mo*
Refinance Your Home

$477,300

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $3,035/mo*
Refinance Your Home
2 Beds
2 Baths
1,573 sqft

Local Information

  • Map ViewExplore the area around 27 Madeira 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
1957
Living Area
1,573 sqft
Price/Sqft
$303

About this House

Beautiful Beach Cottage with a POOL. This 2bed 2 bath with 2 oversized living room areas, a large kitchen island, and screened in porch overlooking the inground pool is only 2 miles from the beautiful St Augustine Beach Oceanfront. Host guests under your covered grilling area, around the pool or enjoy the weekly farmers markets, music festivals, great restaurants all within a 5 minute drive. Bike across the Bridge of Lions to Old Town St Augustine and enjoy Top Restaurants and great nightlife. Perfect for an investment rental or smaller family as it sits on a cul-de-sac with a perfect back yard for entertaining. This home will not last long!
27 Madeira Dr, Saint Augustine, FL 32080 is a 2 bedroom, 2 bathroom, 1,573 sqft single-family home built in 1957. It last sold for $265,000 on Apr 26, 2019. It is currently off market. The Trulia Estimate is $477,300, with a rent estimate of $3,930/month.

Home Details for 27 Madeira Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Other, Hardwood

Exterior Features

Exterior Home Features
Roof: MetalExterior: Cement ConcreteFoundation Type: ConcreteGardenPatioSprinkler System
Pool
Pool

Property Information

Year Built
Year Built: 1957Year Updated: 1988
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 8276 sqft

Price History for 27 Madeira Dr

DatePriceEventSource
04/26/2019$265,000Sold
realMLS #969200
03/20/2019$295,000PendingAgent Provided
01/09/2019$295,000Listed For SaleAgent Provided
03/08/2012$159,500Sold
N/A
01/04/2012$169,900PendingAgent Provided
12/21/2011$169,900PriceChange
Agent Provided
11/11/2011$174,900Listed For SaleAgent Provided
10/25/2002$144,000Sold
N/A

Market trends in Saint Augustine

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$418K
$1.67KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$226
$2MoM
Available listings
1897
43MoM
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Property Tax and Assessment

Year2025
Tax$3,309
Assessment$424,780
Home facts updated by county records

Comparable Sales for 27 Madeira Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
17 Marilyn Ave, Saint Augustine, FL
0.11
Single-Family Home
$495,000
03/18/26
2
2
1,539
1095 Anastasia Blvd, Saint Augustine, FL
0.24
Single-Family Home
$450,000
06/05/26
2
1.5
1,200
30 Madeira Dr, Saint Augustine, FL
0.04
Single-Family Home
$80,000
07/08/26
3
2
1,552
106 Spoonbill Point Ct, St Augustine, FL
0.21
Single-Family Home
$679,000
01/30/26
3
2
1,700
3 Madeira Dr, Saint Augustine, FL
0.16
Single-Family Home
$559,000
02/17/26
3
2
1,180
22 Madeira Dr, Saint Augustine, FL
0.05
Single-Family Home
$565,000
08/15/25
4
3
1,838
125 SPOONBILL POINT Court, Saint Augustine, FL
0.11
Single-Family Home
$273,000
10/08/25
5
4
2,537
19 CASANOVA ROAD, Saint Augustine, FL
0.10
Single-Family Home
$412,500
12/01/25
3
2
2,415
16 Baru Rd, Saint Augustine, FL
0.21
Single-Family Home
$850,000
03/09/26
4
2
2,205
1053 San Rafael St, Saint Augustine, FL
0.36
Single-Family Home
$809,000
10/15/25
3
2
1,664

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Madeira Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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
    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
  • 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
    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

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Apartments for Rent

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Explore by feature - Pet Friendly

319 pet-friendly rentals in Saint Augustine, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

95 rentals with an outdoor space in Saint Augustine, FL

Homes for sale near 27 Madeira Dr

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Off Market Homes Near 27 Madeira Dr

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Frequently asked questions about 27 Madeira Dr

  • What is 27 Madeira Dr estimated to be worth?
    Trulia's estimated value for 27 Madeira Dr in Saint Augustine, FL is $477,300.
  • What is the price history for 27 Madeira Dr?
    27 Madeira Dr in Saint Augustine, FL last sold for $265,000 in April 2019.
  • 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 $418K. That is down $1.67K from the prior month.
  • Does 27 Madeira Dr have air conditioning?
    Yes, 27 Madeira Dr in Saint Augustine, FL has air conditioning.
  • Does 27 Madeira Dr have a pool?
    Yes, 27 Madeira Dr in Saint Augustine, FL has a pool.