One or more photo(s) has been virtually staged. PRICE IMPROVEMENT. Don’t skip this one because of the flood zone. No history of flooding + low insurance premium available. This is your opportunity to own one of Longwood’s most distinctive homes at an unbeatable price per square foot.
Welcome to 153 Duncan Trail, a private retreat on a generous 1/4-acre conservation lot with no rear neighbors. The three-level split layout creates natural separation of space rarely found at this price point. The main living area is centered around a fireplace and opens directly to the backyard deck. The remodeled kitchen (2017) flows alongside an elevated dining area that overlooks the living spaces below, adding architectural character throughout.
The oversized primary suite occupies the upper level, a true private retreat with room for a sitting area or workspace, plus a sliding door opening to an elevated outdoor view above the covered porch. Two additional bedrooms are on the lower level. A spacious dinette, dedicated laundry room with washer/dryer, and epoxy-floored 2-car garage with built-in workbench complete the picture.
Outside, an enclosed back porch leads to an open deck surrounded by conservation, ideal for morning coffee, evening relaxation, or gathering around the dedicated fire-pit area.
MAJOR UPDATES: New architectural roof + gutters (2024) | Full PEX repipe (2024) | Carrier A/C (2022) | Water heater (2020) | Remodeled kitchen & bathrooms (2017) | Fresh interior paint (2025) | All systems serviced (Summer 2025).
Space. Privacy. Peace of mind. Schedule your private showing today.
Welcome to 153 Duncan Trail, a private retreat on a generous 1/4-acre conservation lot with no rear neighbors. The three-level split layout creates natural separation of space rarely found at this price point. The main living area is centered around a fireplace and opens directly to the backyard deck. The remodeled kitchen (2017) flows alongside an elevated dining area that overlooks the living spaces below, adding architectural character throughout.
The oversized primary suite occupies the upper level, a true private retreat with room for a sitting area or workspace, plus a sliding door opening to an elevated outdoor view above the covered porch. Two additional bedrooms are on the lower level. A spacious dinette, dedicated laundry room with washer/dryer, and epoxy-floored 2-car garage with built-in workbench complete the picture.
Outside, an enclosed back porch leads to an open deck surrounded by conservation, ideal for morning coffee, evening relaxation, or gathering around the dedicated fire-pit area.
MAJOR UPDATES: New architectural roof + gutters (2024) | Full PEX repipe (2024) | Carrier A/C (2022) | Water heater (2020) | Remodeled kitchen & bathrooms (2017) | Fresh interior paint (2025) | All systems serviced (Summer 2025).
Space. Privacy. Peace of mind. Schedule your private showing today.
Property Details
Price:
$515,000
MLS #:
O6388268
Status:
Pending
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WEKIVA HILLS SEC 07
Neighborhood:
32779longwoodwekivasprings
Listed Date:
Mar 12, 2026
Finished Sq Ft:
2,596
Total Sq Ft:
3,540
Lot Size:
10,968 sqft / 0.25 acres (approx)
Year Built:
1978
See this Listing
Schools
Elementary School:
Wekiva Elementary
Middle School:
Teague Middle
High School:
Lake Brantley High
Interior
Appliances
Dishwasher, Dryer, Microwave, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Tile
Heating
Central
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)
Laundry Features
Laundry Room
Levels
Two
Exterior
Association Amenities
Basketball Court, Clubhouse, Park, Pickleball Court(s), Playground, Racquetball, Recreation Facilities, Tennis Court(s), Trail(s)
Attached Garage YN
1
Community Features
Clubhouse, Park, Playground, Racquetball, Tennis Court(s)
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
East
Exterior Features
Garden, Private Mailbox, Rain Gutters, Sliding Doors
Garage Spaces
2
Patio And Porch Features
Deck, Rear Porch, Screened
Roof
Shingle
Security Features
Closed Circuit Camera(s)
Financial
HOA Fee
$22
HOA Fee Frequency
Monthly
HOA Includes
Recreational Facilities
HOA Name
Dan Manbracken
HOA Phone
407-774-6111
Tax Year
2024
Taxes
$4,477
Map
Community
- Address153 DUNCAN TRAIL LONGWOOD FL
- SubdivisionWEKIVA HILLS SEC 07
- CityLONGWOOD
- CountySeminole
- Zip Code32779
Subdivisions in LONGWOOD
- ACREAGE & UNREC
- ALAQUA LAKES
- ALAQUA LAKES PH 1
- ALAQUA LAKES PH 4
- BAY LAGOON UNIT 2
- BAY MEADOW FARMS
- BEASON SUB
- BELLA VISTA
- BIG TREE CROSSING PH 2
- BRADLEYS ADD
- BRANTLEY COVE
- BRANTLEY COVE NORTH
- BRANTLEY SHORES 1ST ADD
- CHELSEA PLACE
- CLUBSIDE AT SABAL POINT A CONDO
- COR JESU
- COUNTRY CLUB HEIGHTS UNIT 1
- CROWN OAKS
- CROWN OAKS 1ST ADD
- CRYSTAL CREEK UNIT 1
- CUTLER COVE
- DANBURY MILL UNIT 3A
- DES PINAR ACRES
- DEVONSHIRE
- DON PABLO TWNHMS AT MYRTLE STREET
- ENTZMINGER FARMS ADD 3
- ENTZMINGERS ADD 1
- FAIRWAY VILLAS
- FLORIDA CENTRAL COMMERCE PARK
- GOVERNORS POINT PH 2
- GOVERNORS POINT PH 3 SEC 1
- GOVERNORS POINT PH 3 SEC 2
- GREENWOOD ESTATES
- HANOVER POINTE
- HANOVER POINTE REP – REP
- HENSONS ACRES
- HENSONS ACRES REV OF BLK A
- HIDDEN OAK ESTATES
- HIGHLAND HILLS 1ST REP
- JENNIFER ESTATES
- KATHRYN PARK
- KNOLLWOOD 2ND ADD
- KNOLLWOOD 3RD ADD AMD
- LAKE BRANTLEY HILLS
- LAKE BRANTLEY ISLES 2ND ADD
- LAKE BRANTLEY ISLES AMD
- LAKE SEARCY SHORES
- LAKE VISTA AT SHADOWBAY
- LAKE WAYMAN HEIGHTS LAKE ADD
- LAKESIDE AT SHADOWBAY
- LAKEWOOD POINTE OFFICE PARK A LAND SITE CONDO
- LANDINGS THE
- LAZY ACRES
- LONGDALE
- LONGWOOD
- LONGWOOD CLUB
- LONGWOOD GREEN AMD
- LONGWOOD GREEN HILLS
- LONGWOOD NORTH
- LONGWOOD PARK
- LONGWOOD PLANTATION
- LONGWOOD-MARKHAM ESTATES
- MANCHESTER OAKS
- MANDARIN SEC 2
- MANDARIN SEC 8
- MARKHAM GLEN
- MARKHAM MEADOWS
- MEADOWS UNIT 1
- MEETS AND BOUNDS
- MEREDITH MANOR GOLF VIEW ESTATES SEC
- MEREDITH MANOR NOB HILL SEC
- MOLNARS ADD TO LONGWOOD
- MONTEREY SOUTH
- MYRTLE LAKE HILLS
- NELSON COURT
- NORTH COVE
- NORTHRIDGE RESERVE
- OAKMONT RESERVE
- PALM SPGS CONDO AT THE SPGS
- RANDS ADD TO LONGWOOD
- RANGELINE WOODS
- RAVENSBROOK
- RAVENSBROOK 1ST ADD
- RESERVE AT LAKE WILDMERE – PH 1
- RESIDENCES AT SABAL POINT A CONDO
- RESIDENCES AT SABAL POINT A CONDOMINIU
- RETREAT AT LAKE BRANTLEY
- RIVERSIDE AT THE SPGS
- SABAL POINT AMD
- SABAL POINT AT SABAL GREEN
- SABAL POINT SABAL GLEN AT
- SABAL POINT SABAL RIDGE AT
- SABAL POINT SABAL TRAIL AT
- SAN MARCO VILLAS A CONDO
- SANLANDO COUNTRY CLUB ESTATES
- SANLANDO SPGS
- SANLANDO SPGS LAKE OAKS SEC
- SANLANDO SPRINGS LAKE OAKS SECTION
- SHADOWBAY UNIT 1
- SHADOWBAY UNIT 2
- SHADOWBAY UNIT 2 PH 2
- SKY LARK IN THE WOODS UNIT 2
- SKY LARK UNIT 2 REP
- SLADES PLAN ROCK LAKE
- SLEEPY HOLLOW
- SPRINGS LANDING THE ESTATES AT
- SPRINGS LANDING UNIT 2
- SPRINGS LANDING UNIT 4
- SPRINGS THE
- SPRINGS THE DEERWOOD ESTATES
- SPRINGS THE SHADOWOOD VILLAGE
- SPRINGS THE SHADOWOOD VILLAGE SEC 2
- SPRINGS WHISPERING PINES
- SPRINGS WHISPERING PINES SEC 1
- SPRINGS WHISPERING PINES SEC 2
- SPRINGWOOD
- SPRINGWOOD VILLAGE
- SWEETWATER CLUB
- SWEETWATER CLUB ESTATES
- SWEETWATER CLUB UNIT 1
- SWEETWATER CLUB UNIT 1-A
- SWEETWATER CLUB UNIT 3
- SWEETWATER CLUB UNIT 4
- SWEETWATER COVE
- SWEETWATER OAKS
- SWEETWATER OAKS SEC 02
- SWEETWATER OAKS SEC 03
- SWEETWATER OAKS SEC 04
- SWEETWATER OAKS SEC 06
- SWEETWATER OAKS SEC 07
- SWEETWATER OAKS SEC 09
- SWEETWATER OAKS SEC 12
- SWEETWATER OAKS SEC 15
- SWEETWATER OAKS SEC 17
- SWEETWATER OAKS SEC 18
- SWEETWATER OAKS SWEETWATER SHORES 2
- SWEETWATER SPGS
- TERRA OAKS
- THE ENTERPRISE BLDG A CONDO
- THE SPRINGS
- TIBERON COVE
- WEKIVA CLUB ESTATES SEC 04
- WEKIVA COVE PH 4
- WEKIVA FAIRWAY TWNHMS
- WEKIVA GOLF VILLAS SEC 2
- WEKIVA GREEN
- WEKIVA HILLS SEC 02
- WEKIVA HILLS SEC 05
- WEKIVA HILLS SEC 08
- WEKIVA HUNT CLUB 1 FOX HUNT SEC 1
- WEKIVA HUNT CLUB 3 FOX HUNT SEC 3
- WEKIVA HUNT CLUB CONDO
- WEKIVA VILLAS CONDO
- WEKIVA VILLAS ON THE GREEN 2
- WEST WILDMERE
- WESTLAKE MANOR UNIT 1
- WHISPER WOOD AT SABAL POINT
- WHISPERING WINDS PH 2
- WILDMERE
- WILDMERE AMD
- WILDMERE MANOR
- WINDSOR AT SABAL WALK A CONDO
- WINDTREE WEST
- WINDTREE WEST UNIT 2
- WINGFIELD NORTH 2
- WINGFIELD RESERVE PH 2
- WINSOR MANOR
- WINSOR MANOR 1ST ADD
- WOODLANDS SEC 2
- WOODLANDS SEC 4
- WOODLANDS SEC 5
Market Summary
Current real estate data for Single Family in LONGWOOD as of Apr 30, 2026
207
Single Family Listed
72
Avg DOM
275
Avg $ / SqFt
$809,468
Avg List Price
Property Summary
- Located in the WEKIVA HILLS SEC 07 subdivision, 153 DUNCAN TRAIL LONGWOOD FL is a Single Family for sale in LONGWOOD, FL, 32779. It is listed for $515,000 and features 3 beds, 2 baths, and has approximately 2,596 square feet of living space, and was originally constructed in 1978. The current price per square foot is $198. The average price per square foot for Single Family listings in LONGWOOD is $275. The average listing price for Single Family in LONGWOOD is $809,468. To schedule a showing of MLS#o6388268 at 153 DUNCAN TRAIL in LONGWOOD, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
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Courtesy of LA ROSA REALTY CW PROPERTIES L. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than Charles Rutenberg Realty include the name of the listing broker. Neither the listing company nor Charles Rutenberg Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 153 DUNCAN TRAIL
LONGWOOD, FL