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)
Local Information
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Description
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!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from January 09, 2025
Home Highlights
Parking
2 Car Garage
Outdoor
Porch, Pool
View
Lake, Preserve
HOA
$704/Monthly
Price/Sqft
No Info
Listed
180+ days ago
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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Lease Term: Buyer Finance/Cash |
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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 |
Last check for updates: about 14 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

Price History for 21990 Longleaf Trail DR
| Date | Price | Event | Source |
|---|---|---|---|
| 01/09/2025 | $1,010,000 | Sold | SWFLMLS #224073898 |
| 11/06/2024 | $1,100,000 | Pending | SWFLMLS #224073898 |
| 10/01/2024 | $1,100,000 | Listed For Sale | SWFLMLS #224073898 |
| 04/05/2023 | $960,000 | Sold | N/A |
| 01/18/2023 | $960,000 | Pending | SWFLMLS #222050240 |
| 01/10/2023 | $960,000 | Listed For Sale | SWFLMLS #222050240 |
| 09/12/2022 | ListingRemoved | SWFLMLS #222050240 | |
| 07/23/2022 | $1,100,000 | Listed For Sale | SWFLMLS #222050240 |
| 02/06/2014 | $567,000 | Sold | N/A |
| 10/30/2013 | $589,000 | PriceChange | Agent Provided |
| 10/27/2013 | $489,000 | Listed For Sale | Agent Provided |
| 04/18/2011 | $599,000 | ListingRemoved | Agent Provided |
| 08/03/2010 | $555,000 | Sold | N/A |
| 04/17/2010 | $599,000 | Listed For Sale | Agent Provided |
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $11,168 |
| Assessment | $697,669 |
Home facts updated by county records
Comparable Sales for 21990 Longleaf Trail DR
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 | |
0.20 | Single-Family Home | $685,000 | 08/05/25 | 3 | 2 | 2,000 | |
0.54 | Single-Family Home | $740,000 | 04/20/26 | 3 | 2.5 | 2,337 | |
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 | |
0.31 | 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 | |
0.57 | Single-Family Home | $814,000 | 04/27/26 | 3 | 3.5 | 2,337 | |
0.46 | Single-Family Home | $600,000 | 11/14/25 | 4 | 2.5 | 2,587 | |
0.68 | Single-Family Home | $792,000 | 04/13/26 | 3 | 2.5 | 2,286 |
Assigned Schools
These are the assigned schools for 21990 Longleaf Trail DR.
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
Learn more about our methodology.
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Apartments for Rent
Homes for sale near 21990 Longleaf Trail DR

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.
Homes for rent near 21990 Longleaf Trail DR
Off Market Homes Near 21990 Longleaf Trail DR
Explore by feature
21990 Longleaf Trail DR, Estero, FL 34135 is a 3 bedroom, 3 bathroom, 2,511 sqft single-family home built in 2003. This property is not currently available for sale. 21990 Longleaf Trail DR was last sold on Jan 9, 2025 for $1,010,000 (8% lower than the asking price of $1,100,000). The current Trulia Estimate for 21990 Longleaf Trail DR is $916,900.

