Luxury living awaits at 14423 Hampshire Bay Circle in prime Winter Garden! Spanning ~3,000 sq. ft., this executive 4-bed, 3.5-bath rental blends contemporary elegance with resort-style outdoor comfort. The gourmet chef’s kitchen boasts premium appliances, including a Sub-Zero refrigerator and professional gas range. Unwind in the spacious primary suite or host guests in your private backyard oasis featuring a heated saltwater pool and spa. Complete with luxury finishes, high-end laundry appliances, and convenient access to fine dining, shopping, and major roadways. Contact us today to schedule your private showing!
Property Details
Price:
$5,600
MLS #:
O6454905
Status:
Active
Beds:
4
Baths:
3.5
Type:
Rental
Subtype:
Single Family Residence
Subdivision:
BAY ISLE 48 17
Neighborhood:
34787wintergardenoakland
Listed Date:
Nov 4, 2026
Finished Sq Ft:
2,945
Total Sq Ft:
3,784
Lot Size:
16,876 sqft / 0.39 acres (approx)
Year Built:
2006
See this Listing
Schools
Elementary School:
SunRidge Elementary
Middle School:
Union Park Middle
High School:
West Orange High
Interior
Appliances
Dishwasher, Dryer, Microwave, Range, Range Hood, Refrigerator
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Ceramic Tile, Luxury Vinyl
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, Solid Wood Cabinets, Split Bedroom, Thermostat, Walk-In Closet(s)
Laundry Features
Inside
Levels
Two
Exterior
Association Amenities
Park, Playground
Attached Garage YN
1
Community Features
Dock, Fishing
Covered Spaces
3
Garage Spaces
3
Spa Features
Heated
Financial
HOA Name
Bay Isle / Jim Gordon
Map
Community
- Address14423 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL
- SubdivisionBAY ISLE 48 17
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
- .
- 001
- 30 NORTH PARK
- ACREAGE & UNREC
- ALEXANDER RIDGE
- AMBERLEIGH
- AMBERLEIGH 47/7
- ARROWHEAD LAKES
- AVALON COVE
- AVALON RDG
- AVALON RIDGE
- AVALON WOODS
- BAY ISLE 48 17
- BAY ST PARK
- BELLE MEADE PH 02 H
- BELLE MEADE-PH I B D & G
- BLACK LAKE PARK PH 01
- BLACK LAKE PARK PH 02
- BLACK LAKE PRESERVE
- BLOCK Q SUMMERLAKE PD PH 1B
- BORDERS & WOOSLEY SUB
- BRADFORD CREEK
- BRADFORD CREEK PHASE II
- BRADFORD CRK PH I
- BRADFORD CRK-PH II
- BRANDY CREEK
- BRONSONS LANDING
- BRONSONS LNDGS F & M
- BURCHSHIRE
- CAMBRIDGE CROSSING PH 01A 45/21
- CAMBRIDGE CROSSING PH 1A
- CANOPY OAKS PH 1
- CARRIAGE POINTE
- CARRIAGE POINTE A-I & L
- CHAPIN STATION
- COOPER & SEWELL ADD
- COUNTRY LAKES
- COVINGTON CHASE PH 2B
- COVINGTON PARK
- COVINGTON PARK A B D E F G & J
- CROWN POINT BUS PARK PH 01 43/6
- CROWN POINT SPRINGS
- CROWN POINT TOWN
- CYPRESS RESERVE PH 1
- DANIELS CROSSING
- DANIELS CROSSING PH 03 43/50
- DANIELS CROSSING REP
- DANIELS LANDING
- DANIELS LNDG A-J
- DEERFIELD PLACE A-G
- DEL WEBB OASIS
- DEL WEBB OASIS PH 2
- DEL WEBB OASIS PH 3
- DILLARD PLACE CONDO
- EAST GARDEN MANOR ADD 03
- EAST GARDEN MANOR ADD 03 REP
- EAST GARDEN MANOR REP
- EDGEWATER BEACH
- EMERALD RDG H
- EMERALD RIDGE
- ENCLAVE AT HAMLIN
- ENCLAVE/HAMLIN
- ENCORE AT OVATION
- ENCORE/OVATION PH 2
- ENCORE/OVATION PH 3
- ENCORE/OVATION PH 4B
- ENCORE/OVATION-PH 3
- ESPLANADE AT MCKINNON GROVES
- ESTATES AT LAKEVIEW PRESERVE
- ESTS/LAKEVIEW PRESERVE
- FRIES SURVEY OF WINTER GARDEN
- FRIES WINTER GARDEN
- FULLERS CROSSING PH 01 44/14
- FULLERS LNDG B
- FULLERS OAK
- GARDEN HEIGHTS
- GARDEN WEST
- GLENVIEW ESTATES 1ST ADD
- GLYNWOOD 51 32
- GLYNWOOD II
- GROVA RESIDENCE & SPA HOTEL CONDO 3
- GROVE PK/STONE CREST A-E
- GROVE RESIDENCE & SPA HOTEL
- GROVE RESIDENCE & SPA HOTEL CONDO 1
- GROVE RESIDENCE & SPA HOTEL CONDO 2
- GROVE RESIDENCE & SPA HOTEL CONDO 3
- GROVE RESIDENCE & SPA HOTEL CONDO I
- GROVE RESIDENCE & SPA HOTEL CONDO II
- GROVE RESIDENCE & SPA HOTEL CONDO IL
- GROVE RESIDENCE & SPA HOTEL CONDO LI
- GROVE RESORT
- GROVE RESORT & SPA
- GROVE RESORT & SPA HOTEL CONDO 3
- GROVE RESORT & SPA HOTEL CONDO IV
- GROVE RESORT & SPA HOTEL CONDOMINIUM
- GROVE RESORT AND SPA
- GROVE RESORT AND SPA HOTE CONDOMINIUM 3
- GROVE RESORT AND SPA HOTEL
- GROVE RESORT AND SPA HOTEL CONDO
- GROVE RESORT AND SPA HOTEL CONDO 1
- GROVE RESORT AND SPA HOTEL CONDO 2
- GROVE RESORT AND SPA HOTEL CONDOMIMIUM BUILDING 2
- GROVE RESORT AND SPA HOTEL CONDOMINIUM
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 1
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 2
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 22019039615
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 3
- GROVE RESORT AND SPA HOTEL CONDOMINIUM II
- GROVE RESORT AND WATER PARK
- GROVE RESORT AND WATERPARK
- GROVE/OAKLAND
- GROVEHURST
- GROVEHURST A-D
- HAMILTON GARDENS
- HAMLIN MEADOWS
- HAMLIN MEADOWS AT HAMLIN
- HAMLIN POINTE
- HAMLIN RDG
- HAMLIN RESERVE
- HAMLIN SOUTHWEST
- HARVEST AT OVATION
- HARVEST AT OVATION PHASE 3A
- HARVEST/OVATION
- HARVEST/OVATION PH 2
- HAWKSMOOR
- HAWKSMOOR PH 2
- HAWKSMOOR PH 3
- HAWKSMOOR PH 4
- HAWKSMOOR-PH 1
- HAWKSMOOR-PHASE 1
- HERITAGE/PLANT STREET
- HICKORY HAMMOCK
- HICKORY HAMMOCK PH 1D
- HICKORY HAMMOCK PH 2A
- HICKORY LAKE ESTATES
- HIGHLAND RDG
- HIGHLAND RDG PH 2
- HIGHLAND RIDGE
- HIGHLAND RIDGE PHASE 2
- HIGHLANDS AT SUMMERLAKE GROVES PHASE 1
- HIGHLANDS/SUMMERLAKE GROVE PH 2
- HIGHLANDS/SUMMERLAKE GRVS #1
- HIGHLANDS/SUMMERLAKE GRVS PH 2
- HIGHLANDS/SUMMERLAKE GRVS PH 3
- HIGHLANDS/SUMMERLAKE GRVS PH I
- HILLCREST
- HORIZON ISLE
- HORIZON OAKS
- HULL ISLAND/OAKLAND
- INDEPENDENCE / SIGNATURE LAKES PH 02
- ISLAND POINTE SUB
- ISLES/LK HANCOCK PH III
- J L DILLARD SUB
- J L DILLARD SUB 3
- J S LOVELESS ADD
- J W JONES ADD
- JOE LOUIS PARK
- JOHNS LAKE HOMESITES
- JOHNS LAKE POINTE
- JOHNS LAKE POINTE A & S
- KENNY COURT
- KINGS BAY
- LAGO VISTA TR A
- LAKE APOPKA SOUND
- LAKE APOPKA SOUND PH 1
- LAKE AVALON GROVES
- LAKE AVALON GROVES REP
- LAKE COVE POINTE 46/58
- LAKE COVE POINTE PH 02
- LAKE FOREST SEC 10A
- LAKE HANCOCK PRESERVE
- LAKE ROBERTS LANDING
- LAKE ROBERTS LNDG E
- LAKE STAR AT OVATION
- LAKE STAR AT OVATION PHASE 1B
- LAKE STAR/OVATION PH 1B
- LAKESHORE PRESERVE
- LAKESHORE PRESERVE PH 1
- LAKESHORE PRESERVE PH 2
- LAKESHORE PRESERVE PH 4
- LAKESHORE PRESERVE PH 5
- LAKESHORE PRESERVE PHASE I
- LAKESIDE AT HAMLIN
- LAKESIDE/HAMLIN
- LAKEVIEW POINTE/HORIZON WEST P
- LAKEVIEW POINTE/HORIZON WEST PH
- LAKEVIEW PRESERVE
- LAKEVIEW PRESERVE PH 2
- LAKEVIEW PRESERVE PHASE 2
- LAKEVIEW RESERVE
- LAKEVIEW RESERVE 46/149
- LAKEVIEW VILLAGE ESTATES
- LATHAM PARK NORTH
- LATHAM PARK SOUTH
- LOVELESS & SEWELL
- LOVELESS J S ADD 01
- M C BRITT SUB 1
- MAGNOLIA WOOD FIFTH ADD
- MAGNOLIA WOOD THIRD ADDITION
- MANNS FIRST ADD
- MARY JEAN SUB
- MCALLISTER LNDG
- MERCHANTS SUB
- MEZZANO
- MEZZANO TOWNHOMES
- MT PARK ORANGE GROVE
- NORTHLAKE AT OVATION
- NORTHLAKE AT OVATION PHASE 1
- NORTHLAKE AT OVATION PHASE 2 & 3
- NORTHLAKE AT OVATION PHASE 2 & 3 119/60 LOT 225
- NORTHLAKE AT OVATION PHASE 4
- NORTHLAKE/OVATION PH 1
- OAK PARK AT WINTER GARDEN
- OAKGLEN ESTATES
- OAKLAND HILLS
- OAKLAND PARK
- OAKLAND PARK B-2
- OAKLAND PARK UNIT 1B-1B
- OAKLAND PARKA
- OAKLAND PARKA F1 & F2
- OAKLAND TRAILS
- ORANGE COVE
- ORCHARD
- ORCHARD A1-A26 B1 B2 C D1-D4
- ORCHARD HILLS PH 1
- ORCHARD HILLS PH 2
- ORCHARD HILLS PH 3
- ORCHARD HILLS PH 4
- ORCHARD HILLS PHASE 2
- ORCHARD PK/STILLWATER XING PH
- OSPREY RANCH
- OSPREY RANCH PH 1
- OSPREY RANCH PH I
- OSPREY RANCH-PH 1
- OVERLOOK 2/HAMLIN PH 2 & 5
- OVERSTREET CRATE
- OXFORD CHASE
- PALISADES
- PANTHER VIEW
- PARK AVE ESTATES
- PARK PLACE AT WINTER GARDEN
- PARK PLACE/WINTER GARDEN
- PARKVIEW AT HAMLIN
- PARKVIEW/HAMLIN
- RAVENNA PH 1
- REGAL POINTE PH 02 47/133
- REGENCY OAKS F
- ROPER RESERVE
- SANCTUARY/TWIN WATERS
- SCHENLEY PARK
- SERANADE/OVATION PH 1
- SERENADE AT OVATION
- SERENADE/OVATION PH 1
- SHOREFRONT COVE AT HORIZON WEST
- SIGNATURE LAKES
- SIGNATURE LAKES – PARCEL 1C
- SIGNATURE LAKES – PHASE 2
- SIGNATURE LAKES INDEPENDENCE
- SIGNATURE LAKES PARCEL 1B
- SIGNATURE LAKES PH 02 A B H I J
- SIGNATURE LAKES PH 2
- SIGNATURE LAKES PH 3B-4 3B-5
- SIGNATURE LAKES PH 3B-4 3B-5 &
- SIGNATURE LAKES PH 3B-4 3B-5 & 3
- SIGNATURE LAKES PH 3B-6
- SIGNATURE LAKES PRCL 01C
- SIGNATURE LKS-PCL 01B
- SIGNATURE LKS-PCL 01D PH 01
- SIGNATURE LKS-PCL 01D PH 02
- SIGNATURE LKS-PCL 01D PH 02 – INDEPENDENCE
- SILVERLEAF OAKS
- SILVERLEAF OAKS AT HAMLIN PHASE 3B
- SILVERLEAF OAKS/HAMLIN PH 3A
- SILVERLEAF RESERVE
- SILVERLEAF RESERVE AT HAMLIN
- SILVERLEAF RESERVE/HAMLIN PH 2
- SOUTHERN PINES
- SOUTHERN PINES CONDO
- STANTON ESTATES
- STARLITE COMMERCE CENTER 48 137
- STONE CREEK 48 140
- STONE CREEK UNIT 4
- STONE CRK
- STONE CRK A-1 & A-2
- STONE CRK UN #4
- STONEYBROOK EXCHANGE COMMERCIA
- STONEYBROOK WEST
- STONEYBROOK WEST 44/134
- STONEYBROOK WEST 47/78
- STONEYBROOK WEST D
- STONEYBROOK WEST I
- STONEYBROOK WEST UN 06
- STONEYBROOK WEST UNIT 8
- STONEYBROOK WEST UT 04 48 48
- STOREY GROVE
- STOREY GROVE PH 1A-1
- STOREY GROVE PH 1B 1
- STOREY GROVE PH 1B-1
- STOREY GROVE PH 1B-2
- STOREY GROVE PH 1B-3
- STOREY GROVE PH 2
- STOREY GROVE PH 3
- STOREY GROVE PH 4
- STOREY GROVE PH 5
- STOREY GRV PH 4
- SUBURBAN SHORES
- SUMMERLAKE
- SUMMERLAKE GRVS
- SUMMERLAKE GRVS PH 2
- SUMMERLAKE PD PH 1B
- SUMMERLAKE PD PH 1B – A REP BLK P LOT 14
- SUMMERLAKE PD PH 1B-A REP
- SUMMERLAKE PD PH 2A & 2B
- SUMMERLAKE PD PH 2C 2D 2E
- SUMMERLAKE PD PH 2C-2E
- SUMMERLAKE PD PH 3A
- SUMMERLAKE PD PH 3B
- SUMMERLAKE PD PH 4A
- SUMMERLAKE PD PH 4B
- SUMMERLAKE PD PHASE 2A AND 2B
- SUMMERLAKE RESERVE
- SUMMERLAKES / HIGHLANDS AT SUMMERLAKE GROVES
- SUNSET LAKES
- TEACUP SPGS COVE
- THE GROVE RESORT
- THE GROVE RESORT AND SPA
- THE HARBOR
- TILDEN PLACE
- TILDEN PLACE/WINTER GARDEN
- TOWNHOMES WINTER GARDEN
- TRIBUTE/OVATION
- TUCKER OAKS
- TUCKER OAKS CONDO
- TUCKER OAKS PH 8
- TUSCANY
- TWIN CITY DEV CO SUB
- TWINWATERS
- VALENCIA SHORES
- VERDE PARK PH 1
- VERDE PARK PH 2
- VILLAGE GROVE PH 01
- VILLAGE GROVE PH 02
- VILLAS/TUCKER OAKS
- WALKERS GROVE TWNHMS
- WATER MARK PHASE 4
- WATERLEIGH
- WATERLEIGH PH 1A
- WATERLEIGH PH 1B
- WATERLEIGH PH 1C
- WATERLEIGH PH 2A
- WATERLEIGH PH 2B
- WATERLEIGH PH 2D
- WATERLEIGH PH 2E
- WATERLEIGH PH 3
- WATERLEIGH PH 3A
- WATERLEIGH PH 3B 3C & 3D
- WATERLEIGH PH 3B-3D
- WATERLEIGH PH 4A
- WATERLEIGH PH 4B & 4C
- WATERLEIGH PH 5
- WATERLEIGH PHASE 1A
- WATERLEIGH PHASE 1C
- WATERLEIGH PHASE 2D
- WATERLEIGH PHASE 3BCD
- WATERLEIGH PHASE 4A
- WATERLEIGH PHASES 4B AND 4C
- WATERMARK
- WATERMARK AT HORIZON WEST
- WATERMARK PH 1B
- WATERMARK PH 2A
- WATERMARK PH 2B
- WATERMARK PH 2C
- WATERMARK PH 3
- WATERMARK PH 4
- WATERMARK PH 4A
- WATERMARK PHASE 2C
- WATERSIDE
- WATERSIDE ON JOHNS LAKE
- WATERSIDE ON JOHNS LAKE – PHASE 2C
- WATERSIDE ON JOHNS LAKE PH 1
- WATERSIDE/JOHNS LAKE PH 1
- WATERSIDE/JOHNS LAKE PH 2B
- WATERSIDE/JOHNS LAKE PH 2C
- WATERSIDE/JOHNS LK-PH 1
- WATERSIDE/JOHNS LK-PH 2B
- WATERSIDE/JOHNS LK-PH 2C
- WEST LAKE HANCOCK ESTATES
- WESTFIELD LAKES PH 04 A-F
- WESTHAVEN AT OVATION
- WESTHAVEN/OVATION
- WESTLAKE MANOR
- WESTLAKE MANOR 1ST ADD
- WESTSIDE TOWNHOMES PHASE 2 19/100 LOT 5 BLK 11
- WESTSIDE TWNHMS PH 03
- WESTSIDE TWNHMS PH 04
- WINCEY GRVS PH 2
- WINDING BAY
- WINDING BAY PH 1B
- WINDING BAY PH 2
- WINDING BAY PH 3
- WINDING BAY PRESERVE
- WINDTREE GARDENS
- WINDTREE GARDENS CONDO PH 03
- WINDTREE GARDENS CONDO PH 04
- WINDTREE GARDENS CONDO PH 06
- WINDWARD CAY
- WINDWARD CAY 48 125
- WINTER GARDEN EXECUTIVE CENTRE
- WINTER GARDEN MANOR
- WINTER GARDEN SHORES ADD 02
- WINTER GARDEN SHORES FIRST ADD
- WINTER GARDEN SHORES REP
- WINTER GDN MANOR
- WINTER GROVE
- WINTER GRV
- WINTER OAKS
- WINTERMERE HARBOR
- WINTERMERE HARBOR PH 02 48 21
- WINTERMERE POINTE
- WNDING BAY PH 3
- WOODBRIDGE ON GREEN
Market Summary
Current real estate data for Rental in WINTER GARDEN as of Nov 14, 2026
233
Rental Listed
54
Avg DOM
2
Avg $ / SqFt
$3,095
Avg List Price
Property Summary
- Located in the BAY ISLE 48 17 subdivision, 14423 HAMPSHIRE BAY CIRCLE WINTER GARDEN FL is a Rental for sale in WINTER GARDEN, FL, 34787. It is listed for $5,600 To schedule a showing of MLS#o6454905 at 14423 HAMPSHIRE BAY CIRCLE in WINTER GARDEN, FL, contact your CENTURY 21 Carioti agent at 2392986550.
Similar Listings Nearby
Courtesy of BROKER HUB REALTY GROUP LLC. 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. 14423 HAMPSHIRE BAY CIRCLE
WINTER GARDEN, FL