Welcome to 5445 Chandler in Winter Haven—a great opportunity for buyers looking to add their own personal touch! This home offers generous square footage and plenty of living space, giving you room to spread out, entertain, or reimagine the layout to fit your needs.
The property has already seen some key updates, including a brand-new roof and fresh interior paint, providing a solid foundation for future improvements. Inside, you’ll find a functional layout with large living areas and ample space, making it ideal for those seeking both comfort and potential.
While the home could use some additional updates and TLC, it presents an excellent chance for homeowners or investors to build equity and truly make it their own.
Conveniently located near shopping, dining, and Winter Haven’s beautiful lakes, this property offers both space and opportunity. If you’re looking for a home with room to grow and the ability to add value, this is one you won’t want to miss!
The property has already seen some key updates, including a brand-new roof and fresh interior paint, providing a solid foundation for future improvements. Inside, you’ll find a functional layout with large living areas and ample space, making it ideal for those seeking both comfort and potential.
While the home could use some additional updates and TLC, it presents an excellent chance for homeowners or investors to build equity and truly make it their own.
Conveniently located near shopping, dining, and Winter Haven’s beautiful lakes, this property offers both space and opportunity. If you’re looking for a home with room to grow and the ability to add value, this is one you won’t want to miss!
Property Details
Price:
$290,000
MLS #:
S5146003
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BENTLEY PLACE
Neighborhood:
33884winterhavencypressgardens
Listed Date:
Mar 17, 2026
Finished Sq Ft:
3,010
Total Sq Ft:
3,010
Lot Size:
5,772 sqft / 0.13 acres (approx)
Year Built:
2006
See this Listing
Schools
Interior
Appliances
Built-In Oven, Cooktop, Microwave
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile, Laminate
Heating
Central, Electric
Interior Features
Eating Space In Kitchen, High Ceilings, Thermostat, Walk-In Closet(s)
Laundry Features
Inside
Levels
Two
Exterior
Attached Garage YN
1
Construction Materials
Block, Stucco, Wood Frame
Covered Spaces
2
Direction Faces
Southwest
Exterior Features
Sidewalk, Sliding Doors
Garage Spaces
2
Roof
Shingle
Financial
HOA Fee
$575
HOA Fee Frequency
Annually
HOA Name
Garrison Property Services
HOA Phone
863-353-2558
Tax Year
2025
Taxes
$5,827
Map
Community
- Address5445 CHANDLER DRIVE WINTER HAVEN FL
- SubdivisionBENTLEY PLACE
- CityWINTER HAVEN
- CountyPolk
- Zip Code33884
Subdivisions in WINTER HAVEN
- ACREAGE
- ALMEDA PARK
- ANNA MAR
- AQUALANE HEIGHTS
- ASHTON COVEY
- AUDUBON PLACE
- BENTLEY PLACE
- BERRYHILL
- BILTMORE SHORES
- BLOUNT & WHITLEDGE SUB
- BOOKERS SUB
- BOUNT & WHITLEDGE SUB
- BRADYS SUB
- BRANDY CHASE VILLAGE A REP
- BRENTON MANOR
- BRETTON RIDGE
- BRIDGEWATER
- BROGDEN POINT SUB
- BROOKHAVEN VILLAGE
- BROOKHAVEN VILLAGE FIRST ADD
- BROOKHAVEN VILLAGE SECOND ADD
- BRYSON R H SUB
- BRYSON R H SUBDIVISION
- BUCKEYE HEIGHTS
- BUCKEYE POINTE
- BUCKEYE RDG
- BUCKEYE RIDGE
- BUCKEYE TRACE
- CAMPBELL & HENRY SUB
- CANTON PARK
- CAREFREE COVE
- CAREFREE RV COUNTRY CLUB
- CASA DEL SOL CONDO VILLAGE PH 01
- CASA DEL SOL CONDO VILLAGE PH 02
- CASARENA ON THE LAKE
- CASARENA ON LAKES
- CASARENA ON THE LAKES
- CEDAR COVE PH 01
- CHASE S O SUB
- CHESTNUT CREEK
- CHRIS BROWN CEMETERY REPLAT
- CINNAMON RIDGE PH 03
- COKER A B ADD
- COLLEGE HEIGHTS OR COKER & BUZBEE
- CONINE SHORE
- COOPER ESTATES
- COUNTRY CLUB ESTATES
- COUNTRY LAKE CONDO
- COUNTRY WALK ESTATES PH 03
- COUNTRY WALK PH 02
- COUNTRY WALK PH 03
- COUNTRY WALK/WINTER HAVEN
- COUNTRY WALK/WINTER HAVEN PH 2
- COVENTRY COVE PH II
- CRESCENT POINTE
- CRESCENT VIEW
- CRESTWOOD
- CROSSROADS AT LAKE REGION
- CRYSTALS LANDING
- CYPRESS GROVE
- CYPRESS GROVE PH 04
- CYPRESS LANDING PH 02
- CYPRESS LANDING PH 03
- CYPRESS POINT
- CYPRESS POND
- CYPRESS WOOD
- CYPRESSWOOD
- CYPRESSWOOD ENCLAVE PH 01
- CYPRESSWOOD ENCLAVE PH 02
- CYPRESSWOOD ENCLAVE PH 2
- CYPRESSWOOD FAIRWAY PATIO HOMES
- CYPRESSWOOD GOLF VILLAS
- CYPRESSWOOD GOLF VILLAS BLDG G
- CYPRESSWOOD GOLF VILLAS GC-2
- CYPRESSWOOD GOLF VILLAS GI-4
- CYPRESSWOOD GREENFIELD VILLAGE
- CYPRESSWOOD MDWS
- CYPRESSWOOD MEADOWS
- CYPRESSWOOD PALMA CEIA
- CYPRESSWOOD PATIO HOME
- CYPRESSWOOD PATIO HOMES
- CYPRESSWOOD PLANTATIONS
- CYPRESSWOOD TENNIS VILLAS
- DANIELS SUB
- DEER LAKE TERRACE SUB
- DEERWOOD OR HARRIBEN INVESTMENT CO
- DENISON HEIGHTS ESTATES REP PT
- DEVONWOOD
- DINNER LAKE ESTATES
- DODSONS RESUB
- DOGWOOD-HOLLY CONDO AMD
- DUGGER REP
- DUNDEE STATION
- EAGLE CREST
- EAGLE HEIGHTS
- EAGLE LANDING PHASE II
- EAGLE LNDG PH 1
- EAGLE LNDG PH I
- EAGLE LNDG PH IB
- EAGLE LNDG PH II
- EAGLE POND CONDO
- EAGLES LANDING
- EAST VIEW PKWY
- EDGEWATER MANOR
- EDGEWOOD OR STONE & MANNS
- ELBERT ACRES
- ELBERT HILLS
- ELBERT LANDINGS
- ELOISE COVE
- ELOISE POINTE ESTATES
- ELOISE POINTE ESTATES PB 72 PGS 4&5
- ELOISE WOODS LAKE MARIAM UN
- ELOISE WOODS LAKE MARIAM UNIT
- ELOISE WOODS LAKE RING UNIT
- ELOISE WOODS LAKE ROY UNIT
- ELOISE WOODS WEST LAKE FLORENCE UNIT
- ELWOOD HEIGHTS
- EMERALD ACRES
- EMERALD PALMS
- EMILY ESTATES
- ESTATES/LK FLORENCE
- EULA VISTA SUB
- FAIRVIEW VILLAGE
- FLA HIGHLANDS CO SUB
- FLORENCE CITRUS GROWERS ASSN SUB
- FLORENCE VILLAGE
- FLORIDA HIGHLAND CO
- FLORIDA HLND CO SUB
- FOREST RIDGE
- FOX RIDGE PH 01
- FOX RIDGE PH 02
- FOX RIDGE PHASE ONE
- FOXHAVEN
- FOXHAVEN PH 02
- FOXHAVEN PH 03
- GAINES COVE
- GARDEN GROVE OAKS
- GARDEN GROVE SOUTH
- GARDEN GROVE SOUTH ADD
- GARDEN GROVE SOUTH PH 01 & 02
- GARDEN VILLAS 02 PH 01
- GARDEN VILLAS CONDO PH 01
- GARDEN VILLAS PH 5
- GARDENS INTERLOCHEN
- GARDENS PH 01
- GATES LAKE REGION
- GATES OF LAKE REGION
- GROVE RIDGE
- GRUBBS NILON
- HABITAT FOR HUMANITY 01
- HAMILTON POINTE
- HAMILTON WEST PH 01
- HAMPTON COVE
- HAMPTON WM SUB
- HANNA SUB
- HARBOR AT LAKE HENRY
- HARBOUR ESTATES
- HARMONWOOD SUB
- HARMONY AT LAKE ELOISE
- HARMONY ON LAKE ELOISE
- HARMONY ON LAKE ELOISE PHASE 1
- HARMONY ON LAKE ELOISE PHASE 2
- HARMONY ON LAKE ELOISE PHASE 4
- HARMONY/LK ELOISE PH 1
- HARMONY/LK ELOISE PH 2
- HARRINGTON A B SUB
- HART LAKE COVE PH 02
- HART LAKE HILLS PH 02
- HARTRIDGE HARBOR ADDITION
- HARTRIDGE POINTE CONDO
- HAVEN GROVE MANOR
- HAVEN HOMES
- HAVEN HOMES SUB
- HAVEN PLACE
- HAVEN SHORES
- HAVEN TERRACE
- HAWAIIAN A CONDO
- HEATHER GLEN PH 01
- HEATHER GLEN PH 02
- HEATHER GLEN PHASE TWO
- HERON CAY
- HESS & NAGLE SUB
- HIDDEN CREEK
- HIGHLAND HARBOR
- HILLS LAKE ELBERT
- HILLS OF LAKE ELBERT
- HOFFMANS & LAKE VIEW ADD REP
- HOME PARK UNIT 1 REPLAT PB 28 PG 39
- HOMEWOOD SUB
- HUTCHINSON ADD
- IDA LAKE SUB
- IDYLWILD HEIGHTS
- IMPERIAL HARBOURS
- IMPERIAL HARBOURSPHASES 01 & 02
- IMPERIAL VILLAS
- INMAN F W MRS SUB
- INMAN GROVES
- INMAN GRVS PH 1
- INMAN GRVS PH 2
- INMANS ALLOTMENT
- INTERLAKEN ADD
- INTERLOCHEN
- INWOOD
- INWOOD UN #4
- INWOOD UNIT 3
- IRWIN SUB
- ISLAND LAKES
- JACE LNDG
- JACKSON LNDG
- JAN PHYL VILLAGE
- JAN PHYL VILLAGE #1
- JAN PHYL VILLAGE UNIT 02 PB 37 PG 50
- JARVIS HEIGHTS
- KENILWORTH PARK
- KENNEDY HEIGHTS
- KENSINGTON VIEW
- KINGS COURT
- KINGS POND PH 02
- KOPLIN SUB
- KRENSON BAY
- LAHA WA MANOR
- LAKE ADD
- LAKE ASHTON W PH 2 S
- LAKE ASHTON WEST PH 01
- LAKE ASHTON WEST PH II NORTH
- LAKE ASHTON WEST PH II SOUTH
- LAKE BESS COUNTRY CLUB
- LAKE BUCKEYE CONDO
- LAKE DAISY ESTATES
- LAKE DAISY ESTATES PHASE 2
- LAKE DAISYWOOD
- LAKE DEER
- LAKE DEER PH 2
- LAKE DEXTER MOORINGS
- LAKE DEXTER WOODS 01
- LAKE ELBERT ADD
- LAKE ELBERT ESTATES
- LAKE ELBERT HEIGHTS
- LAKE ELBERT HEIGHTS UNIT 01 02 REP
- LAKE ELBERT HEIGHTS UNIT 02 02 REP
- LAKE ELBERT HEIGHTS UNIT 2 2ND REPLAT
- LAKE HOWARD TERRACE
- LAKE IDYLL ESTATES
- LAKE JESSIE OR CARRS J A
- LAKE KIT
- LAKE KIT CONDO
- LAKE LINK ESTATES
- LAKE LUCERNE II
- LAKE LUCERNE PH 1
- LAKE LUCERNE PH 2 & 3
- LAKE LUCERNE PH 4
- LAKE LUCERNE PH 5
- LAKE LUCERNE PH 6
- LAKE LULU TERRACE
- LAKE MARIAM HILLS REP
- LAKE MAUDE ADD
- LAKE N GOLF ESTATES
- LAKE N GOLF ESTATES ADD
- LAKE N GOLF ESTATES ADD A REP TR B
- LAKE POINT LANDING
- LAKE REGION ESTATE
- LAKE ROCHELLE ESTATES
- LAKE SHIPP HEIGHTS
- LAKE SHIPP OR PORTERS ADD
- LAKE SILVER TERRACE
- LAKE SMART ESTATES
- LAKE SMART POINTE
- LAKE THOMAS ESTATES
- LAKE THOMAS WOODS ADD 03
- LAKE THOMAS WOODS EIGHT ADD
- LAKE THOMAS WOODS SIXTH ADD
- LAKE VIEW SUB PB 3 PG 80
- LAKERIDGE CONDO
- LAKES AT LUCERNE PARK PH 02
- LAKES AT LUCERNE PARK PH 6
- LAKES/LUCERNE PARK PH 4
- LAKES/LUCERNE PARK PH 6
- LAKES/LUCERNE PK PH 6
- LAKESIDE ADD
- LAKESIDE LANDINGS PH 01
- LAKESIDE LANDINGS PHASE 3
- LAKESIDE LNDGS PH 3
- LAKESIDE RANCH FOR MOBILE HOMES
- LAKEWOOD
- LAKEWOOD ACRES
- LAKEWOOD ADD
- LAMPLIGHTER VILLAGE
- LAURENTS ADD
- LE VALLEY SUB PB 37 PG 24
- LEASNICK PARK
- LEISURE SHORES
- LEONARDS SUB
- LESLIE J A
- LESLIE J A SUB
- LESNICK PARK
- LINGER & NICHOLS SUB
- LONGVIEW TERRACE
- LUCERNE PARK
- LUCERNE PARK FRUIT ASSN
- LUCERNE PARK RESERVE
- LUCERNE SHORES
- MADERA PARK SUB
- MAGNOLIA PRESERVE PH 4
- MAGNOLIA SHORES
- MALLARD POINTE
- MANDOLIN
- MANDOLIN 02
- MARIANA HEIGHTS
- MARTHA HEIGHTS
- MAUD MEADOWS
- MAYFAIR ON LAKE PH 01
- MAYFAIR REP
- MAYFAIR SUB
- MILLERS LNDG 3
- MILLSITE SHORES
- MORNINGSIDE
- NORMANDY HEIGHTS
- NORTH GATE VILLAGE PB 46 PG 49 LOT 1213 & INT IN R
- NORTH LAKE ELBERT HEIGHTS
- NOT IN SUBDIVISION
- O BERRY R J SUB
- OAKGROVE SUB
- OAKVIEW
- OAKWOOD ESTATES
- OAKWOOD ESTS
- ORANGE HILL SUB
- ORANGE MANOR WEST COOP INC
- ORANGE PARK SUB
- ORANGE SHORES
- ORANGEWOOD ADD
- ORCHID SPGS
- ORCHID SPGS PATIO HOMES
- ORCHID SPGS VILL 100 CONDO
- ORCHID SPGS VILL 100 CONDOMINIUM
- ORCHID SPGS VILL 200 CONDO
- ORCHID SPGS VILL 300 BARCELONA
- ORCHID SPGS VILL 400 SAN MIGUEL
- ORCHID SPGS VILLAGE #300
- ORCHID SPRINGS PATIO HOMES
- ORCHID SPRINGS UNRECORDED
- ORLEANS
- OSPREY LANDINGS PH 01
- OSPREY POINTE
- OVERLOOK ESTATES
- OVERLOOK ESTS PH 3
- OVERLOOK RDG
- OVERLOOK RIDGE
- OVERSTREETS SUB
- PALMETTO RIDGE ESTATES
- PARK LAKE
- PARK LAKE #2
- PARK LAKE #3
- PARK LAKE 03 02 AMD
- PARKLAND VILLAGE
- PASCO SUB
- PEACE CREEK RESERVE
- PEACE CREEK RESERVE 40’S
- PEACE CREEK RESERVE 40S
- PEACE CREEK RESERVE 50’S
- PEACE CRK RESERVE
- PEACE RIVER DEV
- PEACH CROSSINGS
- PINE CREST HEIGHTS
- PINECREST ADD
- PINNACLE POINT
- PLANTERS WALK PH 03
- PLAZA SUB
- POINSETTIA PARK
- QUEENS COVE
- QUEENS COVE PH 02
- QUEENS COVE PH 03A
- QUEENS COVE PH 04
- RAINBOW KEY SUB
- RAMBLING WOODS
- REFLECTIONS EAST PH 01
- REFLECTIONS EAST PH 02
- RENAISSANCE
- RESIDENCES AT WINTER HAVEN
- REVISED MAP OF FERNWOOD ADD
- RICHMOND SQUARE SUB
- RIDGE ACRES PH 02
- RIDGE ACRES PH II
- ROBINSON SUB
- ROSEWOOD MANOR
- ROYAL CRESCENT CONDO
- ROYAL HILLS
- ROYONNE PLACE RESUB
- RUBY LAKE PH 02
- RUBY LAKE PH 03
- RUBY LAKE PH 04
- SABAL BEND PH 02
- SANCTUARY BAY PH 03
- SANCTUARY BY THE LAKE
- SANCTUARY BY THE LAKE PH 2
- SANCTUARY BY THE LAKE PH ONE
- SANDALWOOD SUB
- SANDY COVE WINTER HAVEN
- SAVANNA POINTE
- SAVANNAH ESTATES
- SAXON-MYERS REP PH 02
- SEASONS AT ANNABELLE ESTATES
- SHADOW WOOD
- SHORES AT LAKE SEARS
- SILVER SHORES
- SILVER SHORES REP
- SILVERCREST ADD
- SMART SUB
- SMITH IDA M 02 REP
- SOLIS GARDENS
- SOUTH COLLEGE
- SOUTH COLLEGE ADD REV
- SOUTHAVEN
- SOUTHEAST TERRACE
- SPIRIT LNDGS
- SPRING LAKE TOWERS
- SQUIRES GROVE
- SQUIRES GROVE PH 2
- ST JAMES XING
- STONEBRIDGE VLS PH 02
- SUMMIT EAST PH 01
- SUMMIT EAST PH 02
- SUN RIDGE VILLAGE PH 01
- SUNDANCE RANCH ESTATES
- SUNNYCROFT
- SUNRIDGE VILLAGE EAST
- SUNSET COVE PH 01
- SUNSET HILLS
- SUNSET PARK
- SUNSHINE TREE PH 01
- SWAN LAKE ESTATES
- TANAMORA
- TAPRELL TERRACE SUB
- TERRANOVA PH 01
- TERRANOVA PH 02
- TERRANOVA PH 03
- TERRANOVA PH 04
- TERRANOVA PH 05
- TERRANOVA PH 05A
- TERRANOVA PH V
- THE HAVEN
- THOMPSON PLACE
- THORNHILL ESTATES
- THORNHILL OAKS
- TIMBER WOOD
- TOWNHOUSES AT PARK LAKE
- TOWNHOUSES AT PARK LAKE 01 REP
- TRADITIIONS PH 1
- TRADITIONS PH 01
- TRADITIONS PH 02
- TRADITIONS PH 1
- TRADITIONS PH 2A
- TRADITIONS PH I
- TRADITIONS PHASE 1
- TRADITIONS VILLAS
- TRAILS TR 22
- TUSCANY AT WINTERSET
- UNINCORPORATED
- UNREC CYPRESSWOOD GOLF VILLAS
- UNREC HEATHER RDG
- US GORVERNMENT
- VALENCIA WOOD ESTATES FIRST ADD
- VALENCIAWOOD HILLS
- VALHALLA
- VAN DUYNE SHORES
- VAN FLEET COMPANYS SUB
- VAN SICKLE C H SUB
- VARNER HEIGHTS
- VIENNA SQUARE
- VIENNA SQUARE DUPLEX
- VIENNA SQUARE PH 01
- VIENNA SQUARE PH 2A
- VIENNA SQUARE PH 2C
- VIENNA SQUARE PH I
- VIENNA SQUARE PHASE 3A
- VILLA HEIGHTS REV
- VILLA MAR
- VILLA MAR 40’S
- VILLA MAR PHASE 3
- VILLAGE PARK
- VILLAGE SPIRIT LAKE ADD
- VILLAGE SPIRIT LAKE PH 01
- VILLAGE/CRYSTAL BEACH
- VILLAMAR
- VILLAMAR PH 1
- VILLAMAR PH 2
- VILLAMAR PH 2A
- VILLAMAR PH 3
- VILLAMAR PH 4
- VILLAMAR PH 5
- VILLAMAR PH 6
- VILLAMAR PH 6 & PH 6D
- VILLAMAR PH 7
- VILLAMAR PH FOUR
- VILLAMAR PHASE 3
- VILLAMAR PHASE 5
- VILLAMAR PHASE 6
- VILLAMAR PHASE 6 PB 203 PG 7-17 LOT 225
- VILLAMAR PHASE 6 AND PHASE 6D
- VILLAMAR PHASE 7
- VILLAMAR PHASE 7 PB 211 PGS 50-57 LOT 280
- VILLAMAR PHASE I
- WAHNETA FARMS
- WAHNETA FARMS RESUB
- WATERFORD OAKS
- WATERS EDGE UNIT 01 A REP
- WATERS EDGE UNIT 01 A REP 02
- WAY SUB
- WELLINGTON PT 01 BLDGS 01 02 & WELLINGTON PT 02 B
- WEST CANNON HEIGHTS
- WEST CANNON TERRACE
- WEST CANNON TERRACE PB 66 PG 7
- WEST OF LAKE HOWARD
- WEST WINTER HAVEN
- WESTWOOD
- WESTWOOD SUB
- WHISPER LAKE 01
- WHISPER LAKE I
- WHISPERING TRAILS PH 01
- WHISPERING TRAILS PH 02
- WILLOWBROOK NORTH
- WILLOWBROOK SOUTH
- WINTER HAVEN
- WINTER HAVEN HARBOUR APTS CONDO
- WINTER HAVEN HEIGHTS
- WINTER HAVEN INDUST PARK
- WINTER LAKE MANOR
- WINTER RDG CONDO
- WINTER RIDGE CONDO
- WINTERSET
- WINTERSET 01 A CONDO 02 AMD
- WINTERSET 02 A CONDO PH 01
- WINTERSET 03 A CONDO PH 01
- WINTERSET GARDENS
- WINTERSET N PH5 PB82 PG 35 LOT 11
- WOLF RUN
- WOODMERE
- WOODPOINTE PH 01
- WOODPOINTE PHASE THREE
- WYNDSOR AT LAKE WINTERSET
Market Summary
Current real estate data for Single Family in WINTER HAVEN as of Sep 08, 2026
814
Single Family Listed
124
Avg DOM
180
Avg $ / SqFt
$329,190
Avg List Price
Property Summary
- Located in the BENTLEY PLACE subdivision, 5445 CHANDLER DRIVE WINTER HAVEN FL is a Single Family for sale in WINTER HAVEN, FL, 33884. It is listed for $290,000 and features 4 beds, 3 baths, and has approximately 3,010 square feet of living space, and was originally constructed in 2006. The current price per square foot is $96. The average price per square foot for Single Family listings in WINTER HAVEN is $180. The average listing price for Single Family in WINTER HAVEN is $329,190. To schedule a showing of MLS#s5146003 at 5445 CHANDLER DRIVE in WINTER HAVEN, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of TRANSCEND REALTY. 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 CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti 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. 5445 CHANDLER DRIVE
WINTER HAVEN, FL