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:
$325,000
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
Laundry Features
Inside
Exterior
Construction Materials
Block, Stucco, Wood Frame
Exterior Features
Sidewalk, Sliding Doors
Roof
Shingle
Financial
HOA Fee
$575
HOA Frequency
Annually
HOA Name
Garrison Property Services
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
- ACREAGE & UNREC
- ANDERSON ESTATES 6
- ANNIE O MADDOX SUB
- AQUALANE HEIGHTS
- ASHTON COVEY
- AUDUBON PLACE
- BENTLEY PLACE
- BERRYHILL
- BEYMER STONER SUB
- BILTMORE SHORES
- BINGHAM JOHN A JR SUB
- BLOUNT & WHITLEDGE SUB
- BONNIE SHORES SUB
- BOUNT & WHITLEDGE SUB
- BRANDY CHASE VILLAGE A REP
- BRENTON MANOR
- BRETTON RIDGE
- BREYMANS
- BRIDGEWATER SUB
- BROGDEN POINT REP
- BROOKHAVEN VILLAGE
- BROOKHAVEN VILLAGE FIRST ADD
- BROOKHAVEN VILLAGE SECOND ADD
- BRYSONS R H SUB
- BUCKEYE HAVEN
- BUCKEYE HEIGHTS
- BUCKEYE HILLS
- BUCKEYE POINTE
- BUCKEYE RDG
- BUCKEYE TRACE
- 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 THE LAKES
- CEDAR COVE PH 01
- CENTRAL POINTE
- CHERRY LAUREL
- CHESTNUT CRK
- COKER A B ADD
- COKER A B SUB
- COLLEGE GROVE REP
- CONINE SHORE
- COOPER & SEWELL ADD
- COOPER ESTATES
- COUNTRY CLUB ESTATES
- COUNTRY CLUB TRAILS
- COUNTRY LAKE CONDO
- COUNTRY LAKE CONDO PH 01
- COUNTRY WALK
- COUNTRY WALK PH 02
- COUNTRY WALK PH 03
- COUNTRY WALK/WINTER HAVEN
- COUNTRY WALK/WINTER HAVEN PH 2
- COVENTRY COVE
- COVENTRY COVE PH II
- CRESCENT POINTE
- CRESCENT VIEW
- CROSSROADS AT LAKE REGION
- CYPRESS GROVE
- CYPRESS GROVE PH 04
- CYPRESS LANDING PH 01
- CYPRESS LANDING PH 02
- CYPRESS POINT
- CYPRESS POND
- CYPRESSWOOD
- CYPRESSWOOD ENCLAVE PH 01
- CYPRESSWOOD ENCLAVE PH 02
- CYPRESSWOOD ENCLAVE PH 2
- CYPRESSWOOD GOLF COMMUNITY
- CYPRESSWOOD GOLF VILLAS
- CYPRESSWOOD GOLF VILLAS GC-2
- CYPRESSWOOD GOLF VILLAS UN 3 B
- CYPRESSWOOD MDWS
- CYPRESSWOOD MEADOWS
- CYPRESSWOOD OAKGROVE
- CYPRESSWOOD PATIO HOMES
- CYPRESSWOOD PLANTATIONS
- CYPRESSWOOD SANDHILL
- CYPRESSWOOD TENNIS VILLAS
- CYPRESSWOOD VILLAS
- DANIELS SUB
- DEER LAKE TERRACE
- DEER LAKE TERRACE SUB
- DEERWOOD OR HARRIBEN INVESTMENT CO
- DENISON HEIGHTS ESTATES REP PT
- DEVONWOOD
- DODSONS RESUB
- DOGWOOD-HOLLY CONDOMINIUM AMENDED
- DUNDEE STATION
- EAGLE CREST
- EAGLE HEIGHTS
- EAGLE LNDG PH I
- EAGLE LNDG PH IB
- EAGLE LNDG PH II
- EAGLE POND
- EAGLE POND CONDO
- EAGLE POND CONDOMINIUMS
- EAGLES LANDING
- EAST COLLEGE ADD
- EAST VIEW PKWY
- EASTWOOD SUBDIVISION, UNIT 1
- EDGEWOOD OR STONE & MANNS
- EL OTIS PARK SUB
- ELBERT ACRES
- ELBERT HILLS
- ELNHIL ADD
- ELNHIL ADDITION
- ELOISE COVE
- ELOISE OAKS
- ELOISE POINTE ESTATES
- ELOISE WOODS
- ELOISE WOODS EAST LAKE MARIAM UNIT
- ELOISE WOODS LAKE MARIAM UN
- ELOISE WOODS LAKE MARIAM UNIT
- ELOISE WOODS LAKE ROY UN
- ELOISE WOODS LAKE ROY UNIT
- ELOISE WOODS RESUB
- ELOISE WOODS WEST LAKE FLORENCE UNIT
- ELWOOD HEIGHTS
- EMERALD PALMS
- EMILY ESTATES
- ESTATES OF LAKE FLORENCE
- ESTATES/LK FLORENCE
- EULA VISTA SUB
- FAIRVIEW VILLAGE
- FANNING SUB
- FERNWOOD ADDITION REVISED MAP OF
- FLA HIGHLANDS CO SUB
- FLORENCE CITRUS GROWERS ASSN SUB
- FLORENCE VILLAGE
- FLORIDA HIGHLAND CO
- FOREST RIDGE
- FOX RIDGE PHASE ONE
- FOXBRIAR SUB
- FOXHAVEN
- GAINES COVE
- GARDEN GROVE OAKS
- GARDEN GROVE OAKS UNIT 04
- GARDEN GROVE SOUTH ADD
- GARDEN GROVE SOUTH PH 01 & 02
- GARDEN GROVE SOUTH SECOND ADD
- GARDEN VILLAS CONDO PH 01
- GARDENS PH 01
- GARDENS PH 1
- GATES LAKE REGION
- GATES/LK REGION
- GRAYDON HILLS
- GREY FOX HOLLOW
- GROVE RDG
- GRUBBS NILON
- HAMILTON MEADOWS
- HAMILTON POINTE
- HAMPTON COVE
- HAMPTON WM SUB
- HANNA SUB
- HARBOR AT LAKE HENRY
- HARBOR AT LAKE HENRY TOWNHOMES
- HARBOUR ESTATES
- HARMONWOOD SUB
- HARMONY AT LAKE ELOISE
- HARMONY ON LAKE ELOISE
- HARMONY/LK ELOISE PH 1
- HARMONY/LK ELOISE PH 2
- HARRINGTON A B SUB
- HART LAKE COVE PH 02
- HART LAKE COVE PH 03
- HARTRIDGE HARBOR ADD
- HARTRIDGE HARBOR ADDITION
- HARTRIDGE HILLS
- HARTRIDGE LANDINGS PROPERTY OWNERS ASSOC
- HARTRIDGE MANOR
- HAVEN GROVE ESTATES
- HAVEN GROVE MANOR
- HAVEN GROVES ESTATES
- HAVEN HOMES SUB
- HAVEN SHORES
- HAVEN TERRACE
- HAVEN TERRACE PB 13 PG 26 BLK 1 LOTS 5 E1/2 & 6 W1
- HAVEN,THE A CONDOMINIUM
- HEATHER GLEN PHASE TWO
- HERON CAY
- HIGHLAND ESTATES
- HILLS LAKE ELBERT
- HILLS OF LAKE ELBERT
- HOBO ACRES
- HOFFMANS & LAKE VIEW ADD REP
- HOME PARK UNIT 1 REPLAT PB 28 PG 39
- HOMEWOOD SUB
- HOWARD CANNON PARK RESUB
- HOWARD CANYON PARK RESUB
- IDA LAKE SUB
- IDYLWILD HEIGHTS
- IMPERIAL HARBOURSPHASES 01 & 02
- INMAN F W MRS SUB
- INMAN GROVES
- INMAN GRVS PH 1
- INMAN GRVS PH 2
- INMANS ALLOTMENT
- INTERLOCHEN
- INWOOD
- INWOOD UNIT 4
- ISLAND LAKES
- JACE LNDG
- JACKSON LNDG
- JAN PHYL VILLAGE
- JAN PHYL VILLAGE ADD
- JAN PHYL VILLAGE UNIT 03 REP
- JAN PHYL VILLAGE UNIT 06
- JAN PHYL VILLAGE UNIT 12
- JARVIS HEIGHTS
- KENNEDY HEIGHTS
- KENSINGTON VIEW
- KINGS COURT
- KINGS POND PH 02
- KOPLIN SUB
- KRENSON BAY
- LAHA WA MANOR
- LAHA-WA MANOR
- LAKE ADD
- LAKE ASHTON WEST PH 01
- LAKE ASHTON WEST PH 2
- LAKE ASHTON WEST PH 2 SOUTH
- 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 DEXTER MOORINGS
- LAKE DEXTER WOODS
- LAKE DEXTER WOODS 01
- LAKE DEXTER WOODS PH 02
- LAKE ELBERT ESTATES
- LAKE ELBERT HEIGHTS
- LAKE ELBERT HEIGHTS UNIT 02 02 REP
- LAKE ELBERT HIGHLANDS
- LAKE ELOISE
- LAKE ELOISE POINTE
- LAKE FOX SHORES
- LAKE HOWARD COVE PINES N SEC REP
- LAKE HOWARD HEIGHTS
- LAKE HOWARD TERRACE
- LAKE IDYLL ESTATES
- LAKE JESSIE OR CARRS J A
- LAKE LINK ESTATES
- LAKE LUCENRNE
- LAKE LUCERNE II
- LAKE LUCERNE PH 1
- LAKE LUCERNE PH 4
- LAKE LUCERNE PH 5
- LAKE LUCERNE PH 6
- LAKE LULU TERRACE
- LAKE MARIAM HILLS REP
- LAKE N GOLF ESTATES
- LAKE N GOLF ESTATES ADD
- LAKE POINT LANDING
- LAKE REGION ESTATE
- LAKE REGION ESTATES
- LAKE ROCHELLE ESTATES
- LAKE SHIPP ADD
- LAKE SHIPP HEIGHTS
- LAKE SHIPP OR PORTERS ADD
- LAKE SILVER TERRACE
- LAKE SMART ESTATES
- LAKE SMART POINTE
- LAKE THOMAS ESTATE #1
- LAKE THOMAS ESTATES
- LAKE THOMAS WOODS ADD 03
- LAKE THOMAS WOODS FIFTH ADD
- LAKE THOMAS WOODS FIFTH ADDITION
- LAKE THOMAS WOODS FOURTH ADD
- LAKE VIEW SUB PB 3 PG 80
- LAKERIDGE CONDO
- LAKES AT LUCERNE PARK
- LAKES AT LUCERNE PARK PH 01
- LAKES AT LUCERNE PARK PH 02
- LAKES AT LUCERNE PARK PHASE FOUR
- LAKES/LUCERNE PARK PH 3
- LAKES/LUCERNE PARK PH 4
- LAKES/LUCERNE PARK PH 6
- LAKES/LUCERNE PK PH 6
- LAKESIDE ADD
- LAKESIDE LANDINGS
- LAKESIDE LANDINGS PH 01
- LAKESIDE LNDGS PH 3
- LAKESIDE RANCH FOR MOBILE HOMES
- LAKEWOOD ACRES
- LAKEWOOD ADD
- LAURENTS ADD
- LEISURE SHORES
- LEONARDS SUB
- LESLIE J A SUB
- LESNICK PARK
- LITTLE LAKE ESTATES
- LUCERNE PARK
- LUCERNE PARK FRUIT ASSN
- LUCERNE PARK RESERVE
- LUCERNE PH 4
- LUCERNE PK RESERVE
- LUCERNE SHORES
- MAGNOLIA PRESERVE
- MAGNOLIA SHORES
- MALLARD POINTE
- MANDOLIN
- MANDOLIN 02
- MAR VISTA
- MARIANA HEIGHTS
- MARTHA HEIGHTS
- MAUD MEADOWS
- MAYFAIR SUB
- MILLERS LANDING
- MIRRO MAC
- MIRRO-MAC
- MOORES EAGLE LAKE SHORES
- MORNINGSIDE
- MORNINGSIDE PH 02
- NORMANDY HEIGHTS
- NORTH LAKE ELBERT HEIGHTS
- NOT IN SUBDIVISION
- NYDEGGERS WEST ELBERT SUB
- O BERRY R J SUB
- OAK LEAF MANOR
- OAK PRESERVE PH 02
- OAKVIEW
- OAKWOOD
- OAKWOOD ESTATES
- OAKWOOD ESTS
- ORANGE HILL SUB
- ORANGE MANOR WEST COOP INC
- ORANGE PARK SUB
- ORANGE SHORES
- ORANGEWOOD HEIGHTS
- 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 FLORIDA HIGHLAND CO
- ORCHID SPRINGS PATIO HOMES
- ORCHID SPRINGS UNRECORDED
- OSPREY LANDINGS PH 01
- OSPREY LANDINGS PH 02
- OSPREY POINTE
- OVERLOOK RDG
- OVERSTREETS SUB
- PARK LAKE
- PARK LAKE #2
- PARK LAKE 03 02 AMD
- PARK LAKE ASSOC 06 PH ONEA CONDO
- PARKLAND VILLAGE
- PEACE CREEK
- PEACE CREEK RESERVE 40’S
- PEACE CREEK RESERVE 50’S
- PEACE CREEK RESERVE PB 197 PGS 5-15 LOT 469
- PEACE CRK RESERVE
- PEACE RIVER DEV
- PEACH CROSSINGS
- PINECREST ADD
- PINNACLE POINT
- PLANTERS WALK
- PLANTERS WALK PH 03
- PLAZA SUB
- POINSETTIA HEIGHTS
- POLLARD SHORES
- QUEENS COVE
- QUEENS COVE PH 03B
- QUEENS COVE PH 04
- RAMBLING WOODS
- REFLECTIONS EAST PHASE ONE
- REVISED MAP OF FERNWOOD ADD
- RICHMOND SQUARE SUB
- RIDGE ACRES PH 02
- ROBINSON SUB
- ROSEWOOD MANOR
- ROSEWOOD MANOR-FIRST AMD
- ROYAL CRESCENT CONDO
- ROYAL HILLS
- ROYONNE PLACE RESUB
- RUBY LAKE PH 01
- RUBY LAKE PH 4
- RUBY LAKE PH 5
- RUBY LAKE PHASE 3
- SANCTUARY BAY PH 03
- SANCTUARY BY THE LAKE PH 1
- SANCTUARY BY THE LAKE PH 2
- SANCTUARY BY THE LAKE PH ONE
- SANDY COVE WINTER HAVEN
- SAVANNA POINTE
- SAXON-MYERS REP PH 02
- SEASONS AT ANNABELLE ESTATES
- SHADOW WOOD
- SHIPP RECK HARBOR
- SHORES AT LAKE SEARS
- SHORES/LK SEARS
- SILVERBELL A CONDO
- SILVERCREST ADD
- SMART SUB
- SMITH IDA M SUB 2ND REPLAT PB 33 PG 16
- SOLIS GARDENS
- SOUTH COLLEGE
- SOUTH COLLEGE ADD REV
- SOUTH ROY SHORES
- SOUTH WINTER HAVEN EXTENSION OF
- SOUTHAVEN
- SOUTHEAST TERRACE
- SPANISH HAVEN
- SPIRIT LAKE SUB
- SPIRIT LNDGS
- SPRING LAKE TOWERS
- SQUIRES GROVE
- SQUIRES GROVE PH 2
- ST JAMES CROSSING
- ST JAMES XING
- STONEBRIDGE VILLAS PH 2 PRCL 8
- STONEBRIDGE VILLAS PHASE II
- STONEBRIDGE VLS PH 02
- SUGAR CRK
- SUMMERHAVEN SHORES
- SUMMIT EAST PH 01
- SUMMIT EAST PH I
- SUN RDG VILLAGE EAST
- SUN RDG VILLAGE WEST
- SUN RIDGE VILLAGE PH 01
- SUN RIDGE VILLAGE WEST
- SUNDANCE RANCH ESTATES
- SUNNYCROFT
- SUNRIDGE VILLAGE EAST
- SUNSET COVE PH 01
- SUNSET HILLS
- SUNSET PARK
- SUNSHINE TREE PH 01
- SUNSHINE TREE PH 03
- SUTTON PRESERVE
- SWAN LAKE ESTATES
- TANAMORA
- TENNIS VILLAS/CYPRESSWOOD BLDG
- TERRACE GARDENS
- TERRACE GARDENS SUB
- TERRANOVA PH 01A
- TERRANOVA PH 02
- TERRANOVA PH 03
- TERRANOVA PH 04
- TERRANOVA PHASE IV
- THOMPSON PLACE
- THORNHILL ESTATES
- THORNHILL OAKS
- TIMBER WOOD
- TIMBER WOOD UNIT 2
- TOM & JERRY
- TOWNHOUSES AT PARK LAKE 01 REP
- TRADITIIONS PH 1
- TRADITIONS
- TRADITIONS PH 01
- TRADITIONS PH 02
- TRADITIONS PH 1
- TRADITIONS PH 2A
- TRADITIONS VILLAS
- TRANQUILITY PARK 02 REP
- TWIN OAKS ADD
- UNREC HEATHER RDG
- UNRECORDED
- VALENCIA PARK
- VALENCIAWOOD HILLS
- VALHALLA
- VAN DUYNE SHORES
- VAN FLEET COMPANYS SUB
- VAN SICKLE C H SUB
- VIENNA SQUARE AND THE VILLAS AT VIENNA S
- VIENNA SQUARE DUPLEX
- VIENNA SQUARE PH 01
- VIENNA SQUARE PH 2A
- VIENNA SQUARE PH 2A AND THE VILLAS AT VI
- VIENNA SQUARE PH 2C
- VIENNA SQUARE PHASE 3A
- VILLA ESTATES SUB
- VILLA HEIGHTS
- VILLA MANOR
- VILLA MAR
- VILLA MAR PHASE 3
- VILLA MAR PHASE 3
- VILLA PARK OR STONE & MANNS
- VILLAGE EAST
- VILLAGE PARK
- 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 FOUR
- VILLAMAR PHASE 3
- VILLAMAR PHASE 5
- VILLAMAR PHASE I
- VILLANAR PH 5
- WAHNETA FARMS
- WATERS EDGE UNIT 1 REPLAT 2
- WATERSIDE VILLAGE
- WELLINGTON PT 01 BLDGS 01 02 & WELLINGTON PT 02 B
- WEST CANNON HEIGHTS
- WEST WINTER HAVEN
- WEST WINTER HAVEN REP
- WESTWOOD SUB
- WHISPER LAKE 01
- WHISPER LAKE 03
- WHISPERING TRAILS PH 01
- WHISPERING TRAILS PH 02
- WHISPERING TRLS PH 1
- WHISPERING TRLS PH I
- WILLARD REP A G WILLARDS
- WILLOWBROOK
- WINDRIDGE
- WINTER HAVEN
- WINTER HAVEN HARBOUR APTS CONDO
- WINTER HAVEN HEIGHTS
- WINTER LAKE MANOR
- WINTER LAKE MANOR ADD
- WINTER RDG CONDO
- WINTER RIDGE CONDO
- WINTERSET 01 A CONDO 02 AMD
- WINTERSET 02 A CONDO PH 01
- WINTERSET 03 A CONDO PH 01
- WOODMERE
- WOODPOINTE PH 1
- WOODPOINTE PHASE THREE
- WYNDSOR AT LAKE WINTERSET
- YONNALLY W P RESUB
- YORK HAVEN
Market Summary
Current real estate data for Single Family in WINTER HAVEN as of Mar 20, 2026
852
Single Family Listed
117
Avg DOM
180
Avg $ / SqFt
$336,438
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 $325,000 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 $108. 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 $336,438. To schedule a showing of MLS#s5146003 at 5445 CHANDLER DRIVE in WINTER HAVEN, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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