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:
$305,000
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
- ACREAGE & UNREC
- ALDORO PARK ADD
- ALMEDA PARK
- AQUALANE HEIGHTS
- ASHTON COVEY
- BENTLEY PLACE
- BERRYHILL
- BILTMORE SHORES
- BINGHAM JOHN A JR SUB
- BLOUNT & WHITLEDGE SUB
- BONNIE SHORES SUB
- BOUNT & WHITLEDGE SUB
- BRANDY CHASE VILLAGE A REP
- BRENTON MANOR
- BREYMANS
- BRIDGEWATER SUB
- BROGDEN POINT REP
- BROOKHAVEN VILLAGE
- BROOKHAVEN VILLAGE FIRST ADD
- BROOKHAVEN VILLAGE SECOND ADD
- BRYSON R H SUB
- BRYSONS R H SUB
- BUCKEYE HAVEN
- BUCKEYE HEIGHTS
- BUCKEYE POINTE
- BUCKEYE RDG
- BUCKEYE RIDGE
- BUCKEYE TRACE
- CAMPBELL & HENRY SUB
- CANTON PARK
- CAREFREE RV COUNTRY CLUB
- CASA DEL SOL CONDO VILLAGE PH 02
- CASARENA ON THE LAKE
- CASARENA ON LAKES
- CASARENA ON THE LAKES
- CEDAR COVE PH 01
- CENTRAL POINTE
- CHESTNUT CRK
- COKER A B ADD
- COLLEGE HEIGHTS OR COKER & BUZBEE
- CONINE SHORE
- COOPER & SEWELL ADD
- COOPER ESTATES
- COUNTRY CLUB ESTATES
- COUNTRY CLUB TRAILS
- COUNTRY LAKE CONDO PH 01
- 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
- COVENTRY COVE PH IL
- CRESCENT POINTE
- CRESCENT VIEW
- CROSSROADS AT LAKE REGION
- CROSSROADS/LK REGION
- CRYSTAL BEACH ESTATES
- CRYSTALS LANDING
- CYPRES LANDNG PH 02
- CYPRESS GROVE PH 04
- CYPRESS LANDING PH 01
- CYPRESS LANDING PH 02
- CYPRESS LANDING PH 03
- CYPRESS POINT
- CYPRESS POND
- CYPRESSWOOD
- CYPRESSWOOD ENCLAVE PH 01
- CYPRESSWOOD ENCLAVE PH 02
- CYPRESSWOOD GOLF VILLAS
- CYPRESSWOOD GOLF VILLAS GC-2
- CYPRESSWOOD GOLF VILLAS UN 3 B
- CYPRESSWOOD MDWS
- CYPRESSWOOD MEADOWS
- CYPRESSWOOD PALMA CEIA
- CYPRESSWOOD PATIO
- CYPRESSWOOD PATIO HOMES
- CYPRESSWOOD PLANTATIONS
- CYPRESSWOOD SANDHILL
- CYPRESSWOOD TENNIS VILLAS
- DANIELS SUB
- DEER LAKE TERRACE
- DEER LAKE TERRACE SUB
- DEERWOOD OR HARRIBEN INVESTMENT CO
- DENISON HEIGHTS ESTATES REP PT
- DEVONWOOD
- DEXTER DELL SUB
- DINNER LAKE ESTATES
- DODSONS RESUB
- DUGGER REP
- DUNDEE STATION
- DUNDEE STATION TR A
- EAGLE CREST
- EAGLE HEIGHTS
- EAGLE LNDG PH 1B
- EAGLE LNDG PH I
- EAGLE LNDG PH IB
- EAGLE LNDG PH II
- EAGLE POND CONDO
- EAGLE POND CONDOMINIUMS
- EAGLES LANDING
- EAST COLLEGE ADD
- EAST VIEW PARKWAY PB 13 PG 4
- EAST VIEW PKWY
- EASTWOOD SUBDIVISION, UNIT 1
- EDGEWOOD OR STONE & MANNS
- EL OTIS PARK SUB
- ELBERT ACRES
- ELBERT HILLS
- ELNHIL ADD
- ELOISE COVE
- ELOISE OAKS
- ELOISE POINTE ESTATES
- ELOISE WOODS EAST LAKE MARIAM UNIT
- ELOISE WOODS LAKE MARIAM UN
- ELOISE WOODS LAKE MARIAM UNIT
- ELOISE WOODS LAKE ROY UNIT
- ELOISE WOODS WEST LAKE FLORENCE UNIT
- ELWOOD HEIGHTS
- EMERALD PALMS
- ESTATES/LK FLORENCE
- EULA VISTA
- EULA VISTA SUB
- FAIRVIEW VILLAGE
- FALCON CREST
- FANNING SUB
- FLA HIGHLANDS CO SUB
- FLORENCE CITRUS GROWERS ASSN SUB
- FLORENCE VILLAGE
- FLORIDA HIGHLAND CO
- FOREST RIDGE
- FOX RIDGE PH 01
- FOX RIDGE PHASE ONE
- FOXHAVEN
- FOXHAVEN PH 02
- FOXHAVEN PH 03
- GAINES COVE
- GARDEN GROVE OAKS
- GARDEN GROVE SOUTH ADD
- GARDEN VILLAS CONDO PH 01
- GARDEN VILLAS PH VIII
- GARDENS PH 01
- GARDENS PH 2
- GATES OF LAKE REGION
- GATES/LK REGION
- GOLF VIEW HEIGHTS
- GRAYDON HILLS
- GREY FOX HOLLOW PH 02
- HAMILTON MEADOWS
- HAMILTON POINTE
- HAMILTON RIDGE
- HAMPTON COVE
- HAMPTON WM SUB
- HANNA SUB
- HARBOR AT LAKE HENRY
- HARMONWOOD SUB
- HARMONY AT LAKE ELOISE
- HARMONY ON LAKE ELOISE
- HARMONY ON LAKE ELOISE PHASE 1
- HARMONY/LK ELOISE PH 1
- HARMONY/LK ELOISE PH 2
- HARRINGTON A B SUB
- HART LAKE COVE PH 02
- HART LAKE COVE PH 03
- HART LAKE HILLS PH 02
- HART LAKE HILLS PH 2
- HARTRIDGE HILLS
- HARTRIDGE LANDINGS PROPERTY OWNERS ASSOC
- HARTRIDGE MANOR
- HARTRIDGE POINTE CONDO
- HAVEN GROVE MANOR
- HAVEN GROVES ESTATES
- HAVEN HOMES
- HAVEN HOMES SUB
- HAVEN PLACE
- HAVEN SHORES
- HAVEN TERRACE
- HAVENCREST ADD
- HAWAIIAN A CONDO
- HEATHER GLEN PH 01
- HEATHER GLEN PHASE TWO
- HERON CAY
- HESS & NAGLE SUB PB 32 PG 10
- HIGHLAND ESTATES
- HIGHLAND HARBOR
- HILLS LAKE ELBERT
- HILLS OF LAKE ELBERT
- HOME PARK
- HOME PARK UNIT 1 REPLAT PB 28 PG 39
- HOWARD CANYON PARK RESUB
- IDA LAKE SUB
- IDYLWILD HEIGHTS
- IMPERIAL HARBOURSPHASES 01 & 02
- INMAN F W MRS SUB
- INMAN GROVES
- INMAN GRVS PH 2
- INMANS ALLOTMENT
- INTERLAKEN ADD
- INWOOD
- INWOOD #4
- INWOOD UNIT 3
- INWOOD UNIT 4
- ISLAND LAKES
- JACE LNDG
- JACKSON LNDG
- JAN PHYL VILLAGE
- JAN PHYL VILLAGE UNIT 03 REP
- JAN PHYL VILLAGE UNIT 06
- JARVIS HEIGHTS
- KENILWORTH PARK
- KENNEDY HEIGHTS
- KENSINGTON VIEW
- KINGS COURT
- KINGS POND PH 02
- KINGS POND PH 1
- KINGS POND SUB
- KOPLIN SUB
- KRENSON BAY
- LAHA WA MANOR
- LAHA-WA MANOR
- LAKE ADD
- LAKE ASHTON WEST ATLEE ADD
- LAKE ASHTON WEST PH 01
- LAKE ASHTON WEST PH 2
- LAKE ASHTON WEST PH II NORTH
- LAKE ASHTON WEST PH II SOUTH
- LAKE BESS COUNTRY CLUB
- LAKE BUCKEYE CONDO
- LAKE DAISY ESTATES PHASE 2
- LAKE DAISYWOOD
- LAKE DEER
- LAKE DEER PH 2
- LAKE DEXTER MOORINGS
- LAKE DEXTER WOODS
- LAKE DEXTER WOODS 01
- LAKE DEXTER WOODS PH 02
- LAKE ELBERT ESTATES
- LAKE ELBERT HEIGHTS UNIT 01 02 REP
- LAKE ELBERT HEIGHTS UNIT 02 02 REP
- LAKE ELOISE PLACE
- LAKE ELOISE POINTE
- LAKE FOX SHORES
- LAKE HOWARD TERRACE
- 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 MAUDE ADD
- LAKE N GOLF ESTATES
- 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 ESTATES
- LAKE THOMAS WOODS ADD 03
- LAKE THOMAS WOODS FIFTH ADD
- LAKE THOMAS WOODS FOURTH ADD
- LAKE VIEW SUB PB 3 PG 80
- LAKE WINTERSET ACRES
- LAKERIDGE CONDO
- LAKES AT LUCERNE PARK PH 6
- LAKES/LUCERNE PARK PH 3
- LAKES/LUCERNE PARK PH 4
- LAKES/LUCERNE PARK PH 6
- LAKES/LUCERNE PK PH 6
- LAKESIDE LANDINGS
- LAKESIDE LANDINGS PH 01
- LAKESIDE LANDINGS PHASE 3
- LAKESIDE LANDINGS PHASE ONE
- LAKESIDE LNDGS PH 3
- LAKESIDE PRESERVE
- LAKESIDE RANCH FOR MOBILE HOMES
- LAKEWOOD ACRES
- LAURENTS ADD
- LE VALLEY SUB PB 37 PG 24
- LEISURE SHORES
- LEONARDS SUB
- LESLIE J A SUB
- LESNICK PARK
- LINGER & NICHOLS SUB
- LITTLE LAKE ESTATES
- LUCERNE PARK
- LUCERNE PARK FRUIT ASSN
- LUCERNE PARK RESERVE
- LUCERNE SHORES
- MADERA PARK SUB
- MAGNOLIA PRESERVE
- MAGNOLIA PRESERVE PH 4
- MAGNOLIA SHORES
- MALLARD POINTE
- MANDOLIN
- MARIANA HEIGHTS
- MARTHA HEIGHTS
- MAUD MEADOWS
- MAYFAIR ON LAKE PH 01
- MAYFAIR SUB
- MILLERS LNDG 3
- MIRRO-MAC
- MONTEGO PLACE
- MOORES EAGLE LAKE SHORES
- MORNINGSIDE
- MORNINGSIDE PH 02
- NORMANDY HEIGHTS
- NORTH GATE VILLAGE PB 46 PG 49 LOT 1213 & INT IN R
- NORTH LAKE ELBERT HEIGHTS
- NOT IN SUBDIVISION
- NOT IN SUBDIVISON
- NYDEGGERS WEST ELBERT SUB
- O BERRY R J SUB
- OAKVIEW
- OAKWOOD ESTATES
- OAKWOOD ESTS
- ORANGE HILL SUB
- ORANGE MANOR WEST COOP INC
- ORANGE PARK SUB
- ORANGE SHORES
- ORANGEWOOD ADD
- 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 RDG
- OVERSTREETS SUB
- PARK LAKE
- PARK LAKE #2
- PARK LAKE 03 02 AMD
- PARK LAKE ASSOC 06 PH ONEA CONDO
- PARKLAND VILLAGE
- PASCO SUB
- PEACE CREEK RESERVE
- PEACE CREEK RESERVE 40’S
- PEACE CREEK RESERVE 40S
- PEACE CREEK RESERVE 50’S
- PEACE CREEK RESERVE PB 197 PGS 5-15 LOT 469
- PEACE CRK RESERVE
- PEACH CROSSINGS
- PINE CREST HEIGHTS
- PINECREST ADD
- PINNACLE POINT
- PLANTERS WALK
- PLANTERS WALK PH 03
- PLAZA SUB
- POINSETTIA HEIGHTS
- QUEENS COVE PH 02
- QUEENS COVE PH 04
- RAMBLING WOODS
- REFLECTIONS EAST PH 01
- REFLECTIONS EAST PHASE ONE
- RENAISSANCE
- RESUBS
- REVISED MAP OF FERNWOOD ADD
- RICHMOND SQUARE SUB
- RIDGE ACRES PH 02
- RIDGE ACRES PH II
- ROSEWOOD MANOR
- ROSEWOOD MANOR-FIRST AMD
- ROYAL CRESCENT CONDO
- ROYAL HILLS
- ROYONNE PLACE RESUB
- RUBY LAKE PH 01
- RUBY LAKE PH 02
- RUBY LAKE PH 03
- RUBY LAKE PH 04
- RUBY LAKE PH 4
- SANCTUARY BAY PH 03
- SANCTUARY BY THE LAKE
- SANCTUARY BY THE LAKE PH 1
- SANCTUARY BY THE LAKE PH 2
- SANCTUARY BY THE LAKE PH TWO
- SAVANNA POINTE
- SAXON-MYERS REP PH 02
- SEASONS AT ANNABELLE ESTATES
- SHADOW WOOD
- SHAFFIELD ESTATES
- SHORES AT LAKE SEARS
- SILVER SHORES
- SILVERBELL A CONDO
- SILVERCREST ADD
- SMART SUB
- SMART SUB PB 10 PG 10
- SMITH IDA M 02 REP
- SOLIS GARDENS
- SOUTH COLLEGE
- SOUTH COLLEGE ADD
- SOUTH COLLEGE ADD REV
- SOUTH LAKE ELBERT HGHTS
- SOUTH LAKE ESLBERT HEIGHTS
- SOUTH ROY SHORES
- SOUTH WINTER HAVEN EXT
- SOUTHAVEN
- SOUTHEAST TERRACE
- SPANISH HAVEN
- SPIRIT LNDGS
- SPRING LAKE TOWERS
- SQUIRES GROVE
- SQUIRES GROVE PH 2
- ST JAMES XING
- STONEBRIDGE VILLAS PH 2 PRCL 8
- SUGAR CRK
- SUMMERHAVEN SHORES
- SUMMIT EAST PH 01
- 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 HILLS
- SUNSHINE TREE PH 01
- SUNSHINE TREE PH 03
- SWAN LAKE ESTATES
- TANAMORA
- TANGERINE PKWY
- TAPRELL TERRACE SUB
- TERRACE GARDENS
- TERRANOVA
- TERRANOVA PH 01
- TERRANOVA PH 03
- TERRANOVA PH 04
- TERRANOVA PH V
- THE HAVEN
- THORNHILL ESTATES
- THORNHILL OAKS
- TIMBER WOOD
- TIMBER WOOD UNIT 2
- TOWNHOUSES AT PARK LAKE
- 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
- UNINCORPORATED
- UNREC HEATHER RDG
- US GORVERNMENT
- VALENCIA PARK
- VALENCIA WOOD ESTS 1ST ADD
- VALENCIA WOOD HILLS
- VALENCIAWOOD HILLS
- VALHALLA
- VAN DUYNE SHORES
- VAN SICKLE C H SUB
- VARNER HEIGHTS
- VIENNA SQUARE
- VIENNA SQUARE AND THE VILLAS AT VIENNA S
- VIENNA SQUARE DUPLEX
- VIENNA SQUARE PH 01
- VIENNA SQUARE PH 2A
- VIENNA SQUARE PH 2C
- VIENNA SQUARE PH I
- VIENNA SQUARE PHASE 3A
- VILLA ESTATES SUB
- VILLA HEIGHTS
- VILLA MANOR
- VILLA MAR
- 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 6
- VILLAMAR PH 6 & PH 6D
- VILLAMAR PH FOUR
- VILLAMAR PHASE 3
- VILLAMAR PHASE 5
- VILLAMAR PHASE I
- WAHNETA FARMS
- WATERFORD OAKS
- WATERS EDGE UNIT 01 A REP
- WATERSIDE VILLAGE
- WAY SUB
- WEIS SUB
- WELLINGTON PT 01 BLDGS 01 02 & WELLINGTON PT 02 B
- WEST CANNON HEIGHTS
- WEST WINTER HAVEN
- WEST WINTER HAVEN REP
- WESTWOOD
- WESTWOOD SUB
- WHISPERING TRAILS PH 01
- WHISPERING TRAILS PH 02
- WHISPERING TRLS PH 01
- WHISPERING TRLS PH 1
- WILLARD REP A G WILLARDS
- WILLOWBROOK
- WILLOWBROOK NORTH
- WINTER HAVEN
- WINTER HAVEN HARBOUR APTS CONDO
- WINTER HAVEN HEIGHTS
- 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 NORTH
- WINTERSET PARK
- WOLF RUN
- WOODMERE
- WOODPOINTE PHASE THREE
- WYNDHAM AT LAKE WINTERSET
- WYNDSOR AT LAKE WINTERSET
- YONNALLY W P RESUB
Market Summary
Current real estate data for Single Family in WINTER HAVEN as of Jun 14, 2026
833
Single Family Listed
115
Avg DOM
180
Avg $ / SqFt
$329,541
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 $305,000 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 $101. 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 $329,541. To schedule a showing of MLS#s5146003 at 5445 CHANDLER DRIVE in WINTER HAVEN, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
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 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. 5445 CHANDLER DRIVE
WINTER HAVEN, FL