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$529,900 Just Listed
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Property Description
There are homes that simply provides space... and there are homes that invite you to slow down and enjoy it. Welcome to 153 Duncan Trail, a distinctive multi-level residence tucked into one of the most peaceful corners of Longwood. Set on a generous ¼ acre lot with no rear neighbors, this 3-bedroom, 2-bath home with 2,596 sq ft offers privacy, character, and room to live in ways that many newer homes simply can't replicate. From the moment you step inside, the home reveals its personality. The main living room centers around a charming fireplace, creating a warm focal point before the space opens toward the backyard deck. It's the kind of room that naturally becomes the heart of the home, whether it's a quiet evening by the fire or gathering with friends before stepping outside. The kitchen has been remodeled (2017) and sits comfortably alongside the dining area. The dining space feels almost like an interior balcony, overlooking the living areas and adding visual openness and architectural interest. Nearby, a spacious dinette and laundry room with washer and dryer make daily life practical and convenient. The layout unfolds across three levels, creating natural separation between living and resting areas. Two bedrooms are located on the lower level, while the primary suite occupies the upper level, offering a sense of retreat from the rest of the home. The primary bedroom is oversized, with plenty of room not only for furniture but for a reading corner, workspace, or private sitting area. A sliding door opens to an elevated outdoor view above the covered porch roof, an unexpected architectural feature that allows natural light and a quiet connection with the outdoors. Step outside and the experience continues. An enclosed back porch with large storage space transitions to an open deck surrounded by nature, where mornings can start with coffee and the sound of birds coming from the conservation behind the property. The backyard also features a dedicated fire-pit area, perfect for evenings under the Florida sky. The property backs up to lush conservation, creating a peaceful natural backdrop. There is even potential for the next owner to enhance the connection with nature by adding a gate from the patio area for easier access to the conservation behind the home. Practical details haven't been overlooked. Major system upgrades have already been completed, including a new architectural roof and gutters (2024), full-home PEX repiping (2024), and a Carrier A/C system installed in 2022, water heater replaced in 2020, fireplace last inspected 2020, Bathrooms remodeled (2017), Interior paint (2025) providing peace of mind for years to come (Last serviced summer 2025). The two-car garage is exceptionally well maintained, finished with an epoxy floor and a functional workbench, ideal for projects, storage, or anyone who appreciates an organized workspace. Homes like this delivers something rare: space, privacy, character, and opportunity, all in one of Central Florida's most established communities.
Full Property Details
Full Property Details for 153 Duncan Trail
General
- Price: $529,900
- HOA FEE: $22/month
- Taxes: $4,477 (2024)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6388268
- Updated: 3/12/2026
- Added to Site: 4 day(s) ago
Rental Information
- Min. Lease: 7 Months
Interior
- Number of Rooms: 12
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Open Floorplan, PrimaryBedroom Upstairs, Skylight(s), Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Living Room
- Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer
- Furnishings: Unfurnished
- Flooring: Carpet, Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Basketball Court, Clubhouse, Park, Pickleball Court(s), Playground, Racquetball, Recreation Facilities, Tennis Court(s), Trail(s)
- Security/Safety: Closed Circuit Camera(s)
Exterior
- Exterior Features: Garden, Private Mailbox, Rain Gutters, Sliding Doors
- Deck/Patio: Deck, Rear Porch, Screened
- Porch/Patio/Deck: Deck, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
Location
- Area: 32779 - Longwood/Wekiva Springs
- County: Seminole
- Development Name: 32779 - Longwood/Wekiva Springs
- Subdivision: WEKIVA HILLS SEC 07
- Driving Directions: From Interstate 4 take Exit 94 for FL-434 toward Longwood/Winter Springs. Head west on FL-434 toward Longwood. Continue for approximately 2.5 miles, then turn right onto Wekiva Springs Road. Drive about 1 mile, then turn left onto Duncan Trail. Continue straight and 153 Duncan Trail will be on the left.
- Direction Faces: East
School Information
- Elementary School: Wekiva Elementary
- Middle School: Teague Middle
- High School: Lake Brantley High
Community
- Community Name: 32779 - Longwood/Wekiva Springs
- Community Features: Clubhouse, Park, Playground, Racquetball, Tennis Court(s)
- Optional Amenities: Basketball Court, Clubhouse, Park, Pickleball Court(s), Playground, Racquetball, Recreation Facilities, Ten
- Association: Yes
- Assoc. Name: Dan Manbracken
- Assoc. Fees Include: Recreational Facilities
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Public
Structural Information
- Exterior Const.: Block, Stucco
- Roof: Shingle
- Stories/Levels: Two
- Square Feet: 2,596
- Sq. Ft. Source: Public Records
- Year Built: 1978
Lot Features
- Lot Size (Acres): 0.25
- Lot Size (Sq. Ft.): 10,968
- Lot Size: 10968
- Street/Road Desc.: Paved
Financial Considerations
- Association Fee: $22
- Assoc Fee Freq.: Monthly
- Assoc Fee Desc.: Required
- Tax Amount: $4,477
- Tax Year: 2024
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: LOT 14 WEKIVA HILLS SEC 7 PB 21 PGS 57 & 58
- Flood Zone Info: AE
- APN: 3120295EP00000140
- Property ID: 3120295EP00000140
Listed by La Rosa Realty Cw Properties L
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Schools
Schools serving 153 Duncan Trail
School District:Seminole County School District
| Name | Grades | Distance |
|---|---|---|
Wekiva Elementary School 1450 E Wekiva Trl, Longwood, FL 32779 | K-5 | 1.2 mi |
Teague Middle School 1350 McNeil Road, Altamonte Springs, FL 32714 | 6-8 | 2.3 mi |
Lake Brantley High School 991 Sand Lake Road, Altamonte Springs, FL 32714 | 9-12 | 2.3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 153 Duncan Trail
Date
Details
Price
Change
Source
3/12/2026
Listed
$529,900
58.18%
MLS
10/30/2020
Sold
$335,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 153 Duncan Trail
Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,525
1%
$361,179
3%
2024
$4,477
2%
$351,000
3%
2023
$4,373
4%
$340,777
6%
2021
$4,191
-2%
$321,215
-3%
2022
$4,266
2%
$330,851
55%
2021
$4,191
57%
$213,820
4%
2018
$2,673
1%
$205,116
2%
2017
$2,655
-2%
$200,897
2%
2016
$2,704
—
$196,765
-6%
2019
$2,698
-1%
$209,013
7%
2015
$2,735
1%
$195,397
1%
2014
$2,711
-1%
$193,846
2%
2013
$2,740
—
$190,981
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 153 Duncan Trail
153 Duncan Trail, Longwood, FL 32779 (MLS# O6388268) is a Single Family property with 3 bedrooms and 2 full bathrooms. 153 Duncan Trail is currently listed for $529,900 and was received on March 12, 2026. Want to learn more about 153 Duncan Trail? Do you have questions about finding other Single Family real estate for sale in Longwood? You can browse all Longwood real estate or contact a Coldwell Banker agent to request more information.

