21990 Longleaf Trail DR
Estero, FL 34135
- 3 Beds
- 2.5 Baths
- 2,511 sqft (on 0.30 acres)
3 Beds
2.5 Baths
2,511 sqft
(on 0.30 acres)
Home Value
Trulia Estimate
$950KSince last month
Increased$10K (+1%)Since last year
$400 (0%)Since last sale
Decreased$57K (-5.6%)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 +36% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $954K |
| July 2026 | $944K |
| June 2026 | $922K |
| May 2026 | $927K |
| April 2026 | $919K |
| March 2026 | $904K |
| February 2026 | $915K |
| January 2026 | $932K |
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 |
|---|---|---|---|---|---|---|---|
0.06 | Single-Family Home | $1,100,000 | 03/19/26 | 4 | 3.5 | 2,686 | |
0.54 | Single-Family Home | $740,000 | 04/20/26 | 3 | 2.5 | 2,337 | |
0.37 | Single-Family Home | $550,000 | 08/05/26 | 3 | 2 | 2,017 | |
0.21 | Single-Family Home | $1,850,000 | 05/05/26 | 3 | 4 | 4,145 | |
0.35 | Single-Family Home | $550,000 | 03/16/26 | 4 | 2 | 2,283 | |
0.45 | Single-Family Home | $525,000 | 06/16/26 | 3 | 2 | 2,342 | |
0.31 | Single-Family Home | $700,000 | 03/19/26 | 5 | 4 | 3,666 | |
0.31 | Single-Family Home | $430,000 | 02/20/26 | 4 | 2.5 | 2,532 | |
0.61 | Single-Family Home | $755,000 | 06/16/26 | 3 | 2 | 2,367 | |
0.36 | Single-Family Home | $600,000 | 07/27/26 | 4 | 2.5 | 2,541 |
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 |
|---|---|---|---|---|---|---|
0.06 | $1,100,000 | 4 | 3.5 | 2,686 | Recently Sold | |
0.07 | $765,400 | 2 | 2 | 1,932 | Off Market | |
0.02 | $1,054,500 | 3 | 2.5 | 2,678 | Off Market | |
0.09 | $181,400 | 2 | 2 | 886 | Off Market | |
0.11 | $116,700 | 1 | 1 | 790 | Off Market | |
0.12 | $161,200 | 2 | 2 | 903 | Off Market | |
0.11 | $175,000 | 2 | 1.5 | 700 | Recently Sold | |
0.13 | $120,000 | 1 | 1 | 865 | Recently Sold | |
0.11 | $153,900 | 2 | 2 | 919 | Off Market | |
0.09 | $849,000 | 4 | 2.5 | 2,453 | For Sale | |
0.16 | $749,000 | 3 | 2 | 2,000 | For Sale |
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
2003
Lot Size
0.3 acres
Living Area
2,511 sqft
Price/Sqft
$378
Parking
2 Car Garage
HOA
$704/Monthly
About this House
Stunning lake and fountain views from this beautifully maintained home (Kingfisher Model) with 3 Bedrooms plus Den, 2.5 Baths and a Southern Exposure! Many quality features including dual AC systems, volume ceilings, under-cabinet lighting, Stainless Steel appliances including a new LG French Door Counter Depth Smart Refrigerator and Range, Wine Cooler, recently painted interior, Quartz countertops in kitchen, an abundance of storage throughout, hurricane protection, Plantation Shutters and much more. This home is situated on a beautiful oversized pie-shaped homesite with additional privacy. Shadow Wood is an upscale community ideally situated between Ft. Myers and Naples with easy access to RSW International Airport, world class shopping, multiple excellent health-care facilities and an abundance of excellent dining options. Shadow Wood Country Club has three championship golf courses, Har Tru tennis courts, Bocce Ball, Pickleball, Private Beach Club, State-of-the-Art Fitness Center and Spa, and miles of biking/walking trails. The new Lifestyle Amenity Center is scheduled to begin in early 2025 with completion in 2026. The new Center will offer a resort-style pool, poolside dining & bar, 6 indoor Pickleball courts, new Racquets Pro Shop, and a Grab & Go Cafe!
21990 Longleaf Trail DR, Estero, FL 34135 is a 3 bedroom, 3 bathroom, 2,511 sqft single-family home built in 2003. It last sold for $1,010,000 on Jan 9, 2025 (8% below the $1,100,000 asking price). It is currently off market. The Trulia Estimate is $949,700, with a rent estimate of $6,050/month.
Last check for updates: about 15 hours ago
Listed by Nancy Woodbury, (239) 564-9534
Downing Frye Realty Inc.
John Woodbury, (239) 564-8214
Downing Frye Realty Inc.
Bought with: Wayne Taylor, (239) 300-1554, John R. Wood Properties
Co-Buyer's Agent: Jennifer Smyth, (312) 953-5809, John R. Wood Properties
Originating MLS: Naples
Source: SWFLMLS, MLS#224073898

Home Details for 21990 Longleaf Trail DR
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Interior Details Number of Rooms: 1Types of Rooms: Dining Room |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2511 Square Feet |
Appliances & Utilities Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator/Icemaker, Self Cleaning Oven, Washer, Wine CoolerDishwasherDisposalDryerLaundry: Inside,Laundry TubMicrowaveWasher |
Heating & Cooling Heating: CentralHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Central |
Fireplace & Spa Spa: In Ground, Concrete, Equipment Stays, Heated, ScreenedNo FireplaceHas a Spa |
Windows, Doors, Floors & Walls Window: Window Coverings, Shutters ElectricFlooring: Carpet, Tile |
Levels, Entrance, & Accessibility Stories: 2Number of Stories: 2Levels: TwoFloors: Carpet, Tile |
View Has a ViewView: Lake, Preserve |
Security Security: Security System, Smoke Detector(s), Gated Community |
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Exterior Home Features Roof: TilePatio / Porch: Screened Lanai/PorchOther Structures: Tennis Court(s)Foundation: Concrete BlockHas a Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Attached |
Pool Pool: In Ground, Concrete, Equipment Stays, Electric Heat, Screen EnclosurePool |
Frontage WaterfrontWaterfront: LakeFrontage Type: LakefrontOn Waterfront |
Farm & Range Not Allowed to Raise Horses |
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Year Built Year Built: 2003 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: Traditional |
Building Building: DSL/Cable AvailableConstruction Materials: Block, StuccoNot a New Construction |
Property Information Parcel Number: 354625E42900B.0430 |
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Price List Price: $1,100,000 |
Status Change & Dates Off Market Date: Thu Jan 09 2025 |
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MLS Status: Closed |
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Direction & Address City: ESTEROCommunity: LONGLEAF |
School Information Elementary School: SCHOOL CHOICEJr High / Middle School: SCHOOL CHOICEHigh School: SCHOOL CHOICE |
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Building Area Building Area: 3006 Square Feet |
Community rooms Fitness Center |
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Community Features: Clubhouse, Fitness Center, Golf, Putting Green, Restaurant, Sidewalks, Street Lights, Tennis Court(s), GatedNot Senior Community |
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Association for this Listing: NaplesHas an HOAHOA Fee: $8,449/Annually |
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Lot Area: 0.30 acres |
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Contingencies: Inspection |
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Mls Number: 224073898Water ViewWater View: Lake |
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HOA Amenities: Beach - Private,Beach Club Available,Bike And Jog Path,Bocce Court,Clubhouse,Community Room,Fitness Center,Golf Course,Internet Access,Pickleball,Play Area,Private Beach Pavilion,Private Membership,Putting Green,Restaurant,Sidewalk,Streetlight,Tennis Court(s),Underground Utility |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Jan 9, 2025 Source: SWFLMLS #224073898 | Sold | $1,010,000 |
Nov 6, 2024 Source: SWFLMLS #224073898 | Pending | $1,100,000 |
Oct 1, 2024 Source: SWFLMLS #224073898 | Listed For Sale | $1,100,000 |
Apr 5, 2023 Source: N/A | Sold | $960,000 |
Jan 18, 2023 Source: SWFLMLS #222050240 | Pending | $960,000 |
Jan 10, 2023 Source: SWFLMLS #222050240 | Listed For Sale | $960,000 |
Sep 12, 2022 Source: SWFLMLS #222050240 | ListingRemoved | |
Jul 23, 2022 Source: SWFLMLS #222050240 | Listed For Sale | $1,100,000 |
Feb 6, 2014 Source: N/A | Sold | $567,000 |
Oct 30, 2013 Source: Agent Provided | PriceChange | $589,000 Price increased by 20% |
Oct 27, 2013 Source: Agent Provided | Listed For Sale | $489,000 |
Apr 18, 2011 Source: Agent Provided | ListingRemoved | $599,000 |
Aug 3, 2010 Source: N/A | Sold | $555,000 |
Apr 17, 2010 Source: Agent Provided | Listed For Sale | $599,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $11,168 | $697,669 |
Home facts updated by county records
Market trends in Estero
Last updated July 2026
Avg. sale price
$506K
$15.83KMoM
Sale-to-List Price
96.3%
0.1%MoM
Price per sq ft
$259
$3MoM
Available listings
560
52MoM
Around this home
What Locals Say about Estero
At least 212 Trulia users voted on each feature.
88 % Say it's dog friendly
87 % Say car is needed
82 % Say parking is easy
75 % Say it's quiet
75 % Say people would walk alone at night
67 % Say there are sidewalks
67 % Say there's holiday spirit
65 % Say streets are well-lit
56 % Say there's wildlife
56 % Say they plan to stay for at least 5 years
52 % Say kids play outside
50 % Say neighbors are friendly
50 % Say yards are well-kept
43 % Say it's walkable to restaurants
42 % Say it's walkable to grocery stores
40 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections

The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS. Copyright 2026 Southwest Florida MLS. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.
Frequently asked questions about 21990 Longleaf Trail DR
- What is 21990 Longleaf Trail DR estimated to be worth?Trulia's estimated value for 21990 Longleaf Trail DR in Estero, FL is $949,700.
- What is the price history for 21990 Longleaf Trail DR?21990 Longleaf Trail DR in Estero, FL last sold for $1,010,000 in January 2025.
- Is Estero a buyer's or seller's market?Estero is currently a buyer's market, based on recent for-sale activity.
- What's the median sale price in Estero?The median sale price in Estero is $506K. That is up $15.83K from the prior month.
- Does 21990 Longleaf Trail DR have air conditioning?Yes, 21990 Longleaf Trail DR in Estero, FL has air conditioning.
- Does 21990 Longleaf Trail DR have a pool?Yes, 21990 Longleaf Trail DR in Estero, FL has a pool.

