Some Photos virtually staged. Solidly built mid-century home in an exceptional Downtown Winter Garden location, just moments from Plant Street shopping and dining, Crooked Can Brewing Company, Garden Theatre, the splash pad, and all the charm of the golf cart district. Enjoy dinner downtown, then take your golf cart to Newton Park to catch breathtaking sunsets over Lake Apopka. Hard to find, timeless charm and well maintained!
Offering 1,716 sq. ft. per the property appraiser, including a spacious laundry room. The roof was replaced in 2016, windows have been updated, and the home includes a termite bond for added peace of mind.
Rare opportunity to own a one owner (since the 60’s) home, lovingly cared for in a Prime Downtown location~ Schedule your private showing today!
Offering 1,716 sq. ft. per the property appraiser, including a spacious laundry room. The roof was replaced in 2016, windows have been updated, and the home includes a termite bond for added peace of mind.
Rare opportunity to own a one owner (since the 60’s) home, lovingly cared for in a Prime Downtown location~ Schedule your private showing today!
Property Details
Price:
$500,000
MLS #:
O6409675
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
REP PT PLEASANT PARK SUB
Neighborhood:
34787wintergardenoakland
Listed Date:
May 25, 2026
Finished Sq Ft:
1,716
Total Sq Ft:
2,037
Lot Size:
9,021 sqft / 0.21 acres (approx)
Year Built:
1955
See this Listing
Schools
Interior
Appliances
Dishwasher, Dryer, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Ceramic Tile
Heating
Electric
Interior Features
Window Treatments
Laundry Features
Inside, Laundry Room
Levels
One
Exterior
Construction Materials
Block
Covered Spaces
1
Direction Faces
East
Exterior Features
French Doors, Irrigation System
Lot Features
City Lot
Other Structures
Shed(s)
Patio And Porch Features
Rear Porch
Roof
Shingle
View
Garden
Window Features
Blinds, Drapes
Financial
Tax Year
2025
Taxes
$709
Map
Community
- Address516 S HIGHLAND AVENUE WINTER GARDEN FL
- SubdivisionREP PT PLEASANT PARK SUB
- CityWINTER GARDEN
- CountyOrange
- Zip Code34787
Subdivisions in WINTER GARDEN
- .
- 30 NORTH PARK
- ACREAGE
- ACREAGE & UNREC
- ALEXANDER RIDGE
- AMBERLEIGH
- AMBERLEIGH 47/7
- ARROWHEAD LAKES
- AVALON COVE
- AVALON ESTATES
- AVALON HILLS SUB
- AVALON RESERVE
- AVALON RESERVE – VILLAGE 1
- AVALON RESERVE VILLAGE 1
- AVALON RIDGE
- AVALON WOODS
- BAY ISLE 48 17
- BAY ST PARK
- BELLE MEADE-PH I B D & G
- BLACK LAKE
- BLACK LAKE PARK PH 01
- BLACK LAKE PARK PH 02
- BLACK LAKE PRESERVE
- BRADFORD CREEK
- BRADFORD CRK PH I
- BRADFORD CRK PH II
- BRAY J W F ADD 01
- BRONSON’S LANDING
- BRONSONS LNDGS F & M
- BURCHSHIRE
- CANOPY OAKS PHASE 1
- CARRIAGE POINTE
- CARRIAGE POINTE A-I & L
- CITRUS COVE UNIT 01
- COBBLESTONE/WINTER GARDEN
- COURTLEA OAKS
- COURTLEA OAKS PH 02B
- COVINGTON CHASE
- COVINGTON CHASE PH 2C
- COVINGTON PARK A B D E F G & J
- CROWN POINT SPGS
- CROWN POINT SPRINGS UT 2
- CYPRESS RESERVE PH 1
- CYPRESS RESERVE PH 2
- CYPRESS RESERVE PHASE 2
- DANIEL CROSSING
- DANIELS CROSSING
- DANIELS CROSSING REP
- DANIELS LANDING
- DANIELS LANDING A-J
- DANIELS LNDG
- DANIELS LNDG A-J
- DEER ISLAND
- DEER ISLAND PH 02
- DEERFIELD PLACE A-G
- DEL WEBB OASIS
- DEL WEBB OASIS PH 2
- DEL WEBB OASIS PH 3
- DEL WEBB OASIS PHASE 2
- DEL WEBB OASIS PHASE 3
- EAST GARDEN MANOR FIRST ADD
- EMERALD ACRES
- ENCLAVE/HAMLIN
- ENCORE AT OVATION
- ENCORE AT OVATION – PHASE 4B 111/103 LOT 410
- ENCORE AT OVATION-PH 3
- ENCORE/OVATION PH 3
- ENCORE/OVATION-PH 2
- ENCORE/OVATION-PH 3
- ENCORE/OVATION-PH 4B
- ESTS/LAKEVIEW PRESERVE
- FRIES WINTER GARDEN
- FULLERS CROSSING PH 01 44/14
- FULLERS LNDG B
- FULLERS XING PH 03 A-G
- GARDEN HEIGHTS
- GARDEN WEST
- GROVE PK/STONE CREST A-E
- GROVE RES & SPA HOTEL CONDO 3
- GROVE RES & SPA HOTEL CONDO IV
- GROVE RESIDENCE & SPA HOTEL
- GROVE RESIDENCE & SPA HOTEL CONDO
- GROVE RESIDENCE & SPA HOTEL CONDO 1
- 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 Y SPA HOTEL CONDO II
- GROVE RESORT
- GROVE RESORT & SPA
- GROVE RESORT & SPA HOTEL CONDO I
- GROVE RESORT & SPA HOTEL CONDO IV
- GROVE RESORT AND SPA
- GROVE RESORT AND SPA CONDOMINIUM 2
- GROVE RESORT AND SPA HOTEL
- GROVE RESORT AND SPA HOTEL CONDO 1
- GROVE RESORT AND SPA HOTEL CONDO II
- 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 2 201903961
- GROVE RESORT AND SPA HOTEL CONDOMINIUM 3
- GROVE RESORT AND SPA HOTEL CONDOMINIUM U
- GROVE RESORT AND WATER PARK
- GROVEHURST A-D
- HAMILTON GARDENS
- HAMILTON GARDENS PH 2A & 2B
- HAMLIN MEADOWS
- HAMLIN MEADOWS AT HAMLIN
- HAMLIN POINTE
- HAMLIN RDG
- HAMLIN RESERVE
- HAMLIN RIDGE
- HARVEST AT OVATION
- HARVEST AT OVATION PHASE 2
- HARVEST/OVATION
- HARVEST/OVATION PH 2
- HAWKSMOOR PH 1
- HAWKSMOOR PH 3
- HAWKSMOOR PH 4
- HAWKSMOOR-PH 1
- HAWKSMOOR-PH 2
- HAWKSMOOR-PH 3
- HERITAGE/PLANT STREET
- HICKORY HAMMOCK
- HICKORY HAMMOCK EMERALD POINTE
- HICKORY HAMMOCK PH 1A
- HICKORY HAMMOCK PH 1D
- HICKORY HAMMOCK PH 2A
- HIGHLAND RDG
- HIGHLAND RDG PH 2
- HIGHLAND RIDGE
- HIGHLAND RIDGE 110/69 LOT 19
- HIGHLANDS AT SUMMERLAKE GROVES
- HIGHLANDS/SUMMERLAKE GROVE
- HIGHLANDS/SUMMERLAKE GROVE PH 2
- HIGHLANDS/SUMMERLAKE GRVS #1
- HIGHLANDS/SUMMERLAKE GRVS PH 1
- HIGHLANDS/SUMMERLAKE GRVS PH 2
- HIGHLANDS/SUMMERLAKE GRVS PH 3
- HILLCREST
- HORIZON ISLES
- INDEPENDENCE
- INDEPENDENCE COMMUNITY
- INDEPENDENCE, SIGNATURE LAKES
- ISLAND POINTE SUB
- ISLES LAKE HANCOCK
- ISLES OF LAKE HANCOCK
- J L DILLARD SUB 3
- JOE LOUIS PARK
- JOHNS LAKE POINTE
- JOHNS LAKE POINTE A & S
- K HOVNANIAN WINDING BAY PRESERVE
- KING BAY
- LAKE APOPKA SOUND
- LAKE AVALON GROVES
- LAKE AVALON GROVES REP
- LAKE AVALON GROVES REP 02
- LAKE AVALON GRVS 2ND REP
- LAKE AVALON HEIGHTS
- LAKE FOREST SEC 10A
- LAKE HANCOCK PRESERVE
- LAKE ROBERTS LNDG E
- LAKE STAR AT OVATION
- LAKESHORE PRESERVE
- LAKESHORE PRESERVE PH 1
- LAKESHORE PRESERVE PH 2
- LAKESHORE PRESERVE PH 4
- LAKESHORE PRESERVE PH 5
- LAKESIDE AT HAMLIN
- LAKESIDE/HAMLIN
- LAKEVIEW POINTE
- LAKEVIEW POINTE/HORIZON WEST
- LAKEVIEW POINTE/HORIZON WEST P
- LAKEVIEW PRESERVE
- LAKEVIEW PRESERVE PH 2
- LAKEVIEW RESERVE 46/149
- LATHAM PARK NORTH
- LATHAM PARK SOUTH
- LIFT STATION/COBBLESTONE/WINTE
- LOVELESS J S ADD 01
- MAGNOLIA WOOD
- MAGNOLIA WOOD FIFTH ADD
- MANNS FIRST ADD
- MARY JEAN SUB
- MCALLISTER LNDG
- MCALLISTER LNDG PH 2
- MERCHANTS SUB
- MEZZANO
- MILLERS PT WINTER GARDEN
- MT PARK ORANGE GROVE
- NORTHLAKE AT OVATION
- NORTHLAKE AT OVATION PHASE 1 109/122 LOT 135
- NORTHLAKE AT OVATION PHASE 2 & 3
- NORTHLAKE AT OVATION PHASE 2 & 3 119/60 LOT 194
- NORTHLAKE/OVATION PH 1
- OAK PARK AT WINTER GARDEN
- OAKLAND
- OAKLAND PARK
- OAKLAND PARK UT 1B – 1A
- OAKLAND PARKB-1
- OAKLAND PARKB-2
- OAKS/BRANDY LAKE 01 REP A & B
- OAKS/BRANDY LAKE O
- ORANGE COVE
- ORANGE GROVE SUB
- ORCHARD A1-A26 B1 B2 C D1-D4
- ORCHARD HILLS PH 1
- ORCHARD HILLS PH 2
- ORCHARD HILLS PH 2 SIGNATURE LAKES
- ORCHARD HILLS PH 3
- ORCHARD HILLS PHASE 2
- ORCHARD PK/STILLWATER XING
- ORCHARD PK/STILLWATER XING PH
- OSPREY RANCH
- OSPREY RANCH PH 1
- OSPREY RANCH-PH 1
- OVERLOOK 2 AT HAMLIN
- OVERLOOK 2/HAMLIN PH 1 & 6
- OVERLOOK 2/HAMLIN PH 2 & 5
- OVERLOOK AT HAMLIN/WEST LAKE HANCOCK ESTATES
- OVERSTREET CRATE
- OXFORD CHASE
- PALISADES
- PALISADES CONDO
- PANTHER VIEW
- PARK PLACE
- PARK PLACE/WINTER GARDEN
- PARKVIEW AT HAMLIN
- PARKVIEW/HAMLIN
- PROMINENT POINTE PHASE 2
- RAVENNA
- RAVENNA PH 1
- REGAL POINTE PH 01 43/129
- REGAL POINTE PH 02 47/133
- REGENCY OAKS F
- REGENCY OAKS PH 02 A-C
- RESERVE AT CARRIAGE POINTE
- RESERVE CARRIAGE POINTE
- ROPER RESERVE
- SANCTUARY/HAMLIN
- SANCTUARY/TWIN WATERS
- SAVANNAH RIDGE SUB
- SCHENLEY PARK
- SERENADE AT OVATION
- SHADOW LAWN
- SHOREFRONT COVE
- SHOWALTER PARK
- SIGNATURE LAKES
- SIGNATURE LAKES PARCEL 1A
- SIGNATURE LAKES PARCEL 1D
- SIGNATURE LAKES PH 02 A B H I J
- SIGNATURE LAKES PH 2
- SIGNATURE LAKES PH 3B-2 & 3B-3
- SIGNATURE LAKES PH 3B-4, 3B-5
- SIGNATURE LAKES PH 3B-4, 3B-5 & 3B-7 83/27 LOT 184
- SIGNATURE LAKES PH 3B-6
- SIGNATURE LAKES PHASE 3B-6 83/8 LOT 1807
- SIGNATURE LAKES PRCL 01C
- SIGNATURE LAKES-PCL 01D PH 02
- SIGNATURE LAKES, INDEPENDENCE
- SIGNATURE LKS-PCL 01A
- SIGNATURE LKS-PCL 01B
- SIGNATURE LKS-PCL 01D PH 01
- SIGNATURE LKS-PCL 01D PH 02
- SILVERLEAF OAKS
- SILVERLEAF OAKS AT HAMLIN PHASE 3A
- SILVERLEAF OAKS/HAMLIN PH 3A
- SILVERLEAF RESERVE
- SILVERLEAF RESERVE BUNGALOWS
- SILVERLEAF RESERVE/HAML PH 2A
- SILVERLEAF RESERVE/HAMLIN PH 2
- SIPLIN HEIGHTS
- SOLOMON SUB
- SOUTHERN PINES
- SOUTHERN PINES CONDO
- SOUTHERN PINES CONDOMINIUM
- STARLITE COMMERCE CENTER 48 137
- STONE CREEK 44/131
- STONE CREEK UNIT 4
- STONE CRK A-1 & A-2
- STONEYBROOK WEST
- STONEYBROOK WEST 44/134
- STONEYBROOK WEST D
- STONEYBROOK WEST I
- STONEYBROOK WEST UT 04 48 48
- STONEYBROOK WEST UT 04 REP 49 121
- STOREY GROVE
- STOREY GROVE 50
- STOREY GROVE PH 1A-1
- STOREY GROVE PH 1B-1
- STOREY GROVE PH 1B-2
- STOREY GROVE PH 1B-4
- STOREY GROVE PH 1B-4A
- STOREY GROVE PH 2
- STOREY GROVE PH 3
- STOREY GROVE PH 4
- STOREY GROVE PH 5
- STOREY GROVE PHASE 4
- STOREY GRV PH 2
- STORY ROAD BUS PARK
- SUMMERLAKE
- SUMMERLAKE GRVS
- SUMMERLAKE GRVS PH 2
- SUMMERLAKE PD PH 01A
- SUMMERLAKE PD PH 1A
- SUMMERLAKE PD PH 1B
- SUMMERLAKE PD PH 1B A REP
- 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 3C
- SUMMERLAKE PD PH 4B
- SUMMERLAKE PD PHASES 2C, 2D, 2E 83/145 LOT 9 BLK I
- SUMMERLAKE RESERVE
- THE GROVE RESORT
- THE GROVE RESORT AND SPA
- TILDEN PLACE/WINTER GARDEN
- TOWNHOMES OF WINTER GARDEN CONDO
- TOWNHOMES WINTER GARDEN
- TRIBUTE AT OVATION
- TRIBUTE AT OVATION WAY
- TRIBUTE OF OVATION
- TRIBUTE/OVATION
- TROYNELLE BY LAKE APOPKA
- TROYNELLE/BIG LAKE APOPKA
- TUCKER OAKS
- TUCKER OAKS CONDO PH 1
- TUCKER OAKS CONDO PH 7
- TUSCANY
- TUSCANY PH 02
- TWINWATERS
- TWINWATERS HOMEOWNERS’ ASSOCIATION, INC.
- VALENCIA SHORES
- VERDE PARK PH 1
- VILLAGE GROVE PH 01
- VILLAGE GROVE PH 02
- VILLAGE GROVE PHASE 2
- VILLAS AT TUCKER OAKS
- VININGS ADD WINTER GARDEN
- WALKERS GROVE TWNHMS
- WATERLEIGH
- WATERLEIGH PH 1A
- WATERLEIGH PH 1B
- WATERLEIGH PH 2A
- WATERLEIGH PH 2B
- WATERLEIGH PH 2C-1
- WATERLEIGH PH 2D
- WATERLEIGH PH 2E
- WATERLEIGH PH 3A
- WATERLEIGH PH 3B & 3C
- WATERLEIGH PH 3B 3C & 3D
- WATERLEIGH PH 3B-3D
- WATERLEIGH PH 4A
- WATERLEIGH PH 4B & 4C
- WATERLEIGH PH 4B 4C
- WATERLEIGH PH 5
- WATERLEIGH PHASE 5 116/135 LOT 228
- WATERMARK
- WATERMARK PH 1A
- WATERMARK PH 1B
- WATERMARK PH 2A
- WATERMARK PH 2B
- WATERMARK PH 2B1
- WATERMARK PH 2C
- WATERMARK PH 3
- WATERMARK PH 4
- WATERMARK PHASE 4A
- WATERSIDE ON JOHNS LAKE
- WATERSIDE ON JOHNS LAKE PH 1
- WATERSIDE/JOHNS LAKE PH 2A
- WATERSIDE/JOHNS LAKE PH 2C
- WATERSIDE/JOHNS LK-PH 1
- WATERSIDE/JOHNS LK-PH 2A
- WATERSIDE/JOHNS LK-PH 2B
- WEST LAKE HANCOCK ESTATES
- WESTCHESTER PLACE
- WESTFIELD LAKES PH 04 A-F
- WESTHAVEN AT OVATION
- WESTHAVEN/OVATION
- WESTLAKE MANOR 1ST ADD
- WESTSIDE TOWNHOMES
- WESTSIDE TWNHMS
- WINCEY GROVES
- WINCEY GROVES PHASE 2
- WINCEY GRVS PH 1
- WINCEY GRVS PH 2
- WINDING BAY II LLC
- WINDING BAY PH 1B
- WINDING BAY PH 2
- WINDING BAY PH 3
- WINDING BAY PRESERVE
- WINDTREE GARDENS
- WINDTREE GARDENS CONDO PH 01
- WINDTREE GARDENS CONDO PH 02
- WINDTREE GARDENS CONDO PH 03
- WINDTREE GARDENS CONDO PH 05
- WINDTREE GARDENS PHASE 5
- WINTER GARDEN MANOR
- WINTER GARDEN SHORES REP
- WINTER GARDEN TRLS 01-3
- WINTER GROVE
- WINTERMERE POINTE
- WINTERMERE POINTE PH 02 46/141
- WINTERS LNDG PH 01 A D F & G
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of May 26, 2026
808
Single Family Listed
109
Avg DOM
282
Avg $ / SqFt
$767,912
Avg List Price
Property Summary
- Located in the REP PT PLEASANT PARK SUB subdivision, 516 S HIGHLAND AVENUE WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $500,000 and features 3 beds, 2 baths, and has approximately 1,716 square feet of living space, and was originally constructed in 1955. The current price per square foot is $291. The average price per square foot for Single Family listings in WINTER GARDEN is $282. The average listing price for Single Family in WINTER GARDEN is $767,912. To schedule a showing of MLS#o6409675 at 516 S HIGHLAND AVENUE in WINTER GARDEN, FL, contact your WINDERMERE INTERNATIONAL REALTY agent at 4079901329.
Similar Listings Nearby
Courtesy of WINDSOR REALTY GROUP INC. 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 WINDERMERE INTERNATIONAL REALTY include the name of the listing broker. Neither the listing company nor WINDERMERE INTERNATIONAL 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. 516 S HIGHLAND AVENUE
WINTER GARDEN, FL