Is a car needed in Monterey, Jacksonville, FL?

As of early 2026, 94% of users say car is needed

Is Monterey, Jacksonville, FL dog-friendly?

As of early 2026, 92% of users say it's dog friendly

Is parking easy in Monterey, Jacksonville, FL?

As of early 2026, 84% of users say parking is easy

Are the streets well-lit in Monterey, Jacksonville, FL?

As of early 2026, 64% of users say streets are well-lit

Does Monterey, Jacksonville, FL have sidewalks?

As of early 2026, 60% of users say there are sidewalks

Is Monterey, Jacksonville, FL quiet?

As of early 2026, 56% of users say it's quiet

Does Monterey, Jacksonville, FL show holiday spirit?

As of early 2026, 50% of users say there's holiday spirit

Do kids play outside in Monterey, Jacksonville, FL?

As of early 2026, 47% of users say kids play outside

Are neighbors friendly in Monterey, Jacksonville, FL?

As of early 2026, 39% of users say neighbors are friendly

Is Monterey, Jacksonville, FL walkable to restaurants?

As of early 2026, 29% of users say it's walkable to restaurants

Are yards well-kept in Monterey, Jacksonville, FL?

As of early 2026, 27% of users say yards are well-kept

Is Monterey, Jacksonville, FL walkable to grocery stores?

As of early 2026, 27% of users say it's walkable to grocery stores

Do residents of Monterey, Jacksonville, FL plan to stay at least 5 years?

As of early 2026, 21% of users say they plan to stay for at least 5 years

Is there wildlife in Monterey, Jacksonville, FL?

As of early 2026, 17% of users say there's wildlife

Would people walk alone at night in Monterey, Jacksonville, FL?

As of early 2026, 15% of users say people would walk alone at night

Are there community events in Monterey, Jacksonville, FL?

As of early 2026, 12% of users say there are community events

What is 5566 Windermere Dr estimated to be worth?

Trulia's estimated value for 5566 Windermere Dr in Jacksonville, FL is $163,100 .

Is Jacksonville a buyer's or seller's market?

Jacksonville is currently a balanced market, based on recent for-sale activity.

What's the median sale price in Jacksonville?

The median sale price in Jacksonville is $287K. That is up $3.33K from the prior month.

What do residents say about the Monterey neighborhood?

Residents describe the Monterey neighborhood in Jacksonville, FL as dog-friendly, easy to park in, and pedestrian-friendly. See recently sold homes in Monterey, Jacksonville .

Does 5566 Windermere Dr have air conditioning?

Yes, 5566 Windermere Dr in Jacksonville, FL has air conditioning.

How big is the lot at 5566 Windermere Dr?

The lot at 5566 Windermere Dr in Jacksonville, FL is about 0.19 acres (8,440 sq ft).

OFF MARKET

$163,100

Trulia Estimate

3 Beds
1 Bath
970 sqft

5566 Windermere Dr, Jacksonville, FL 32211

Monterey

Est. Refi. Payment $1,188/mo*

Refinance Your Home

Home Value

Trulia Estimate

$163K

Since last month

$8K (-4.9%)

Since last year

$1K (+0.7%)

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 +160% in the last 10 years

Month	Estimated value
2026
September 2026	$162K
August 2026	$163K
July 2026	$170K
June 2026	$167K
May 2026	$173K
April 2026	$168K
March 2026	$169K
February 2026	$168K
January 2026	$157K
2025
December 2025	$156K
November 2025	$159K
October 2025	$151K
September 2025	$155K
August 2025	$160K
July 2025	$162K
2024
December 2024	$164K
November 2024	$171K
October 2024	$162K
September 2024	$163K
August 2024	$167K
July 2024	$172K
June 2024	$175K
May 2024	$175K
April 2024	$175K
March 2024	$172K
February 2024	$164K
January 2024	$161K
2023
December 2023	$161K
November 2023	$160K
October 2023	$162K
September 2023	$164K
August 2023	$167K
July 2023	$164K
June 2023	$167K
May 2023	$171K
April 2023	$168K
March 2023	$168K
February 2023	$166K
January 2023	$170K
2022
December 2022	$171K
November 2022	$175K
October 2022	$179K
September 2022	$176K
August 2022	$181K
July 2022	$184K
June 2022	$182K
May 2022	$180K
April 2022	$178K
March 2022	$174K
February 2022	$165K
January 2022	$163K
2021
December 2021	$160K
November 2021	$158K
October 2021	$156K
September 2021	$157K
August 2021	$158K
July 2021	$158K
June 2021	$159K
May 2021	$163K
April 2021	$159K
March 2021	$144K
February 2021	$142K
January 2021	$138K
2020
December 2020	$134K
November 2020	$130K
October 2020	$120K
September 2020	$119K
August 2020	$119K
July 2020	$118K
June 2020	$117K
May 2020	$121K
April 2020	$121K
March 2020	$119K
February 2020	$116K
January 2020	$115K
2019
December 2019	$114K
November 2019	$121K
October 2019	$123K
September 2019	$123K
August 2019	$124K
July 2019	$126K
June 2019	$120K
May 2019	$119K
April 2019	$118K
March 2019	$116K
February 2019	$113K
January 2019	$111K
2018
December 2018	$113K
November 2018	$114K
October 2018	$113K
September 2018	$107K
August 2018	$107K
July 2018	$104K
June 2018	$98K
May 2018	$93K
April 2018	$85K
March 2018	$85K
February 2018	$82K
January 2018	$85K
2017
December 2017	$87K
November 2017	$90K
October 2017	$88K
September 2017	$90K
August 2017	$88K
July 2017	$84K
June 2017	$85K
May 2017	$83K
April 2017	$81K
March 2017	$72K
February 2017	$72K
January 2017	$77K
2016
December 2016	$77K
November 2016	$80K
October 2016	$61K
September 2016	$62K

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
5704 MICHIGAN Avenue, Jacksonville, FL	0.18	Single-Family Home	$210,000	06/15/26	3	1	984
1421 Bretta St, Jacksonville, FL	0.19	Single-Family Home	$75,000	10/15/25	3	1	1,056
5317 RIVER FOREST Drive, Jacksonville, FL	0.27	Single-Family Home	$199,000	10/30/25	3	1	1,006
5540 WINDERMERE Drive, Jacksonville, FL	0.04	Single-Family Home	$247,500	09/30/25	3	2	1,244
5318 S RIVER ROAD, Jacksonville, FL	0.32	Single-Family Home	$200,000	09/10/26	3	1	962
5377 RIVER FOREST Drive, Jacksonville, FL	0.19	Single-Family Home	$226,500	07/17/26	2	1	1,204
1407 MAGNOLIA Circle E, Jacksonville, FL	0.25	Single-Family Home	$225,000	03/09/26	2	1	1,060
5308 S RIVER Road, Jacksonville, FL	0.33	Single-Family Home	$260,000	05/22/26	3	1	1,376
5861 MICHIGAN Avenue, Jacksonville, FL	0.36	Single-Family Home	$230,000	05/14/26	3	1	1,257
5528 N OLIVER Street, Jacksonville, FL	0.13	Single-Family Home	$334,000	05/22/26	3	2	1,513

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
5519 RIVER FOREST Drive, Jacksonville, FL 32211	0.05	$230,000	3	2	1,574	For Sale
5540 WINDERMERE Drive, Jacksonville, FL 32211	0.04	$250,100	3	2	1,244	Off Market
5489 OAK FOREST Drive, Jacksonville, FL 32211	0.06	$285,000	3	2	1,404	Recently Sold
5659 ANSLEY Street, Jacksonville, FL 32211	0.14	$267,000	4	2	1,872	Recently Sold
0 UNIVERSITY Boulevard, Jacksonville, FL 32211	0.10	$214,600	2	1	676	Off Market
5640 WILTSHIRE STREET, Jacksonville, FL 32211	0.12	$244,100	3	1	1,376	Off Market
1424 EASTER Street, Jacksonville, FL 32211	0.14	$137,900	1	1	687	Recently Sold
5436 RIVER FOREST Drive, Jacksonville, FL 32211	0.13	$201,500	3	1	1,103	Off Market
5431 RIVER FOREST Drive, Jacksonville, FL 32211	0.12	$259,000	4	2	1,487	For Sale
1441 CLOCK Street, Jacksonville, FL 32211	0.14	$228,100	3	1	1,248	Off Market
5419 RIVER FOREST Drive, Jacksonville, FL 32211	0.14	$159,000	3	2	1,470	Recently Sold
1814 UNIVERSITY Boulevard N, Jacksonville, FL 32211	0.13	$238,300	4	2	1,593	Off Market

Local Information

Map ViewExplore the area around 5566 Windermere Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1950

970 sqft

$168/sqft

About this House

This is a beautiful SFH home in Jacksonville! Lots of space and in great condition! The only thing this property needs to get a good paying tenant inside is some upgrades. Visit this property today to see the potential, won't last long!

5566 Windermere Dr, Jacksonville, FL 32211 is a 3 bedroom, 1 bathroom, 970 sqft single-family home in Monterey, built in 1950. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $163,100, with a rent estimate of $1,475/month.

Home Details for 5566 Windermere Dr

Interior Features
Levels, Entrance, & Accessibility Stories: 1Floors: Other
Interior Details Number of Rooms: 1
Heating & Cooling Air ConditioningCooling System: Central
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherExterior: Other

Property Information
Year Built Year Built: 1950Year Updated: 1970
Property Type / Style Property Type: Single Family HomeArchitecture: Other

Community
Units in Building: 1

Lot Information
Lot Area: 8440 sqft

Price and Tax history

Date	Event	Price
Dec 29, 2016 Source: Agent Provided	ListingRemoved	$80,000
Dec 6, 2016 Source: Agent Provided	PriceChange	$80,000 Price decreased by 4%
Nov 10, 2016 Source: Agent Provided	Listed For Sale	$83,000

Year	Property tax	Tax assessment
2025	$2,255	$158,703

Additional Cost

Market trends in Jacksonville

Last updated August 2026

Avg. sale price

$287K

$3.33KMoM

Sale-to-List Price

98.4%

0.1%MoM

Price per sq ft

$180

$1MoM

Available listings

5070

44MoM

Around this home

Arlington Elementary School
PK-5
Public
178 Students
Duval County Public Schools
5/10
GreatSchools Rating
Parent Rating Average
Always nice and helpful when asked questions.
Parent Review
9y ago
9 Reviews

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.

Neighborhood Overview

Monterey

9 Homes For You
Buy: $99.5k - $650k

See Local Highlights

Neighborhood stats provided by third party data sources.

What Locals Say about Monterey

At least 12 Trulia users voted on each feature.

94 % Say car is needed
92 % Say it's dog friendly
84 % Say parking is easy
64 % Say streets are well-lit
60 % Say there are sidewalks
56 % Say it's quiet
50 % Say there's holiday spirit
47 % Say kids play outside
39 % Say neighbors are friendly
29 % Say it's walkable to restaurants
27 % Say yards are well-kept
27 % Say it's walkable to grocery stores
21 % Say they plan to stay for at least 5 years
17 % Say there's wildlife
15 % Say people would walk alone at night
12 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Monica P.
Resident
7y ago
"no special events, we as owners and fellow neighbors just look out for each other and our properties. ensuring that the place we lay our heads at are safe and welcoming. "
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Frequently asked questions about 5566 Windermere Dr

What is 5566 Windermere Dr estimated to be worth?
Trulia's estimated value for 5566 Windermere Dr in Jacksonville, FL is $163,100.
Is Jacksonville a buyer's or seller's market?
Jacksonville is currently a balanced market, based on recent for-sale activity.
What's the median sale price in Jacksonville?
The median sale price in Jacksonville is $287K. That is up $3.33K from the prior month.
What do residents say about the Monterey neighborhood?
Residents describe the Monterey neighborhood in Jacksonville, FL as dog-friendly, easy to park in, and pedestrian-friendly. See recently sold homes in Monterey, Jacksonville.
Does 5566 Windermere Dr have air conditioning?
Yes, 5566 Windermere Dr in Jacksonville, FL has air conditioning.
How big is the lot at 5566 Windermere Dr?
The lot at 5566 Windermere Dr in Jacksonville, FL is about 0.19 acres (8,440 sq ft).