Under contract-accepting backup offers. 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:
Pending
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
- ADDITION TO MARY JEAN SUB
- ALEXANDER RIDGE
- ANNIE L BERRY SUB
- ARROWHEAD LAKES
- AVALON ESTATES
- AVALON HILLS SUB
- AVALON RDG
- AVALON RESERVE VILLAGE 1
- AVALON RIDGE
- AVALON WOODS
- BAY ISLE 48 17
- BAY ST PARK
- BELLE MEADE PH 02 H
- BELLE MEADE PH 2
- BELLE MEADE-PH I B D & G
- BLACK LAKE
- BLACK LAKE PARK PH 01
- BLACK LAKE PARK PH 02 F-1
- BLACK LAKE PRESERVE
- BLACK LK PK PH 1
- BRADFORD CREEK-PH II
- BRADFORD CRK PH I
- BRADFORD CRK PH II
- BRANDY CREEK
- BRAY J W F ADD 01
- BRONSONS LNDGS F & M
- BURCHSHIRE
- BURCHSHIRE Q/138 LOT 8 BLK B
- CAMBRIDGE CROSSING PH 02 43/147
- CANOPY OAKS PH 1
- CANOPY OAKS PHASE 1
- CARRIAGE POINTE A-I & L
- CITRUS COVE UNIT 01
- COOPER & SEWELL ADD
- COUNTRY LAKES
- COURTLEA OAKS
- COURTLEA OAKS PH 01A
- COVINGTON CHASE
- COVINGTON CHASE PH 2A
- COVINGTON PARK A B D E F G & J
- CROWN POINT SPGS
- CYPRESS RESERVE PH 2
- DANIEL CROSSING
- DANIELS LANDING
- DANIELS LNDG A-J
- DEER ISLAND
- DEER ISLAND PH 02
- DEERFIELD PLACE A-G
- DEL WEBB OASIS
- DEL WEBB OASIS PH 3
- EAST GARDEN MANOR ADD 03 REP
- ELLMAN PARK
- EMERALD ACRES
- ENCLAVE AT HAMLIN
- ENCORE AT OVATION
- ENCORE AT OVATION – PHASE 4B 111/103 LOT 410
- ENCORE AT OVATION-PH 3
- ENCORE/OVATION PH 1
- ENCORE/OVATION PH 2
- ENCORE/OVATION PH 3
- ENCORE/OVATION PH 4B
- ENCORE/OVATION-PH 3
- ENCORE/OVATION-PH 4B
- ESTATES AT LAKEVIEW
- ESTATES AT LAKEVIEW PRESERVE
- ESTS/LAKEVIEW PRESERVE
- FOXCREST
- FRIES SURVEY OF WINTER GARDEN
- FRIES WINTER GARDEN
- FULLERS XING PH 03 A-G
- G T SMITH SUB
- G T SMITH SUB 3
- G T SMITH SUB 4
- GLENVIEW ESTATES
- GLENVIEW ESTATES 2ND ADD
- GREYSTONE PH 01
- 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 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 Y SPA HOTEL CONDO II
- GROVE RESORT
- GROVE RESORT & SPA
- GROVE RESORT & SPA HOTEL CONDO IV
- GROVE RESORT AND SPA
- GROVE RESORT AND SPA HOTEL
- GROVE RESORT AND SPA HOTEL CONDO 1
- 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 3
- GROVE RESORT AND SPA HOTEL CONDOMINIUM U
- GROVE RESORT HOTEL AND SPA HOTEL CONDO 1
- GROVEHURST
- HAMILTON GARDENS
- HAMILTON GARDENS PH 2A & 2B
- HAMLIN POINTE
- HAMLIN RDG
- HAMLIN RESERVE
- HAMLIN RIDGE
- HARVEST AT OVATION
- HARVEST/OVATION
- HARVET AT OVATION
- HAWKSMOOR – PHASE 2
- HAWKSMOOR PH 1
- HAWKSMOOR PH 3
- HAWKSMOOR PH 4
- HAWKSMOOR-PH 1
- HAWKSMOOR-PH 3
- HERITAGE/PLANT STREET
- HICKORY HAMMOCK PH 1B
- HICKORY HAMMOCK PH 1D
- HICKORY HAMMOCK PH 2A
- HICKORY HAMMOCK PH 2B
- HIGHLAND RDG
- HIGHLAND RDG PH 2
- HIGHLAND RIDGE
- HIGHLAND RIDGE 110/69 LOT 19
- HIGHLANDS/SUMMERLAKE GROVE PH 2
- HIGHLANDS/SUMMERLAKE GRVS PH 1
- HIGHLANDS/SUMMERLAKE GRVS PH 2
- HIGHLANDS/SUMMERLAKE GRVS PH 3
- HILLCREST
- HORIZON ISLE
- ILVERLEAF OAKS AT HAMLIN
- INDEPENDENCE COMMUNITY
- ISLAND POINTE SUB
- ISLES/LK HANCOCK PH 3
- ISLES/LK HANCOCK PH III
- J L DILLARD SUB 3
- J S LOVELESS ADD
- JOE LOUIS PARK
- JOHNS LAKE POINTE
- JOHNS LAKE POINTE A & S
- K HOVNANIAN WINDING BAY PRESERVE
- LAKE APOPKA SOUND
- LAKE APOPKA SOUND PH 1
- LAKE AVALON GROVES
- LAKE AVALON GROVES 2ND REP
- 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 STAR AT OVATION
- LAKE VIEW ADD
- LAKESHORE PRESERVE PH 1
- LAKESHORE PRESERVE PH 2
- LAKESHORE PRESERVE PH 5
- LAKESHORE PRESERVE PH I
- LAKESIDE AT HAMLIN
- LAKEVIEW POINTE/HORIZON WEST
- LAKEVIEW POINTE/HORIZON WEST 1
- LAKEVIEW POINTE/HORIZON WEST P
- LAKEVIEW PRESERVE
- LAKEVIEW PRESERVE PH 2
- LAKEVIEW PRESERVE PHASE 2
- LAKEVIEW RESERVE 46/149
- LATHAM PARK
- LATHAM PARK NORTH
- LATHAM PARK SOUTH
- LATHAN PARK NORTH
- LOVELESS & SEWELL ADD
- LOVELESS J S ADD 01
- MANNS FIRST ADD
- MARY JEAN SUB
- MCALLISTER LNDG
- MCALLISTER LNDG PH 2
- MERCHANTS SUB
- MEZZANO
- MOUNTAIN PARK ORLANGE GROVES
- NORTHLAKE AT OVATION
- NORTHLAKE AT OVATION PHASE 1 109/122 LOT 37
- NORTHLAKE AT OVATION PHASE 2 & 3
- NORTHLAKE/OVATION PH 1
- OAKLAND PARK
- OAKLAND PARKB
- OAKLAND PARKB-1B A
- OAKLAND PK UN 7 SOUTH 112/136 LOT 175
- OAKLAND TRLS PH 1
- OAKS/BRANDY LAKE
- OAKS/BRANDY LAKE O
- ORANGE COVE
- ORCHARD A1-A26 B1 B2 C D1-D4
- ORCHARD HILLS
- ORCHARD HILLS PH 1
- ORCHARD HILLS PH 2
- ORCHARD HILLS PH 3
- ORCHARD HILLS PH 4
- ORCHARD HILLS PH I
- ORCHARD HILLS PHASE 3
- ORCHARD PK/STILLWATER XING PH
- OSPREY RANCH
- OSPREY RANCH PH 1
- OSPREY RANCH-PH 1
- OVERLOOK 2 AT HAMLIN PHASE 2 AND 5
- OVERLOOK 2/HAMLIN PH 1 & 6
- OVERLOOK 2/HAMLIN PH 2 & 5
- OVERLOOK 2/HAMLIN PH 3 & 4
- OVERLOOK AT HAMLIN
- OVERSTREET CRATE
- OXFORD CHASE
- PALISADES
- PALISADES CONDO
- PANTHER VIEW
- PARK PLACE
- PARK PLACE/WINTER GARDEN
- PARK SUB
- PARKVIEW AT HAMLIN
- PARKVIEW/HAMLIN
- PLEASANT PARK
- QUESINBERRY SUB
- RAVENNA
- RAVENNA PH 1
- REGENCY OAKS F
- REGENCY OAKS PH 02 A-C
- RESERVE/CARRIAGE POINT PH 1
- RESERVE/CARRIAGE POINTE PH 1
- ROLLING HILLS AVALON ANNEX
- ROPER RESERVE
- SANCTUARY/HAMLIN
- SANCTUARY/TWIN WATERS
- SAVANNAH RIDGE SUB
- SERENADE AT OVATION
- SERENADE AT OVATION PHASE I
- SERENADE/OVATION PH 1
- 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 2A
- SIGNATURE LAKES PH 3B-1
- SIGNATURE LAKES PH 3B-4, 3B-5
- SIGNATURE LAKES PH 3B-4, 3B-53B-
- SIGNATURE LAKES PH 3B-5 & 3B-7
- SIGNATURE LAKES PH 3B-6
- SIGNATURE LAKES PRCL 01C
- SIGNATURE LAKES, INDEPENDENCE
- SIGNATURE LKS-PCL 01A
- SIGNATURE LKS-PCL 01B
- SIGNATURE LKS-PCL 01D PH 01
- SIGNATURE LKS-PCL 01D PH 02
- SILVER SPRINGS BUNGALOWS
- SILVERLEAF OAK
- SILVERLEAF OAKS
- SILVERLEAF OAKS AT HAMLIN PHASE 3A
- SILVERLEAF OAKS/HAMLIN PH 3A
- SILVERLEAF RESERVE
- SILVERLEAF RESERVE AT HAMLIN
- SILVERLEAF RESERVE AT HAMLIN PHASE 2A
- SILVERLEAF RESERVE BUNGALOWS
- SILVERLEAF RESERVE/HAMLIN
- SILVERLEAF RESERVE/HAMLIN PH 2
- SIPLIN HEIGHTS
- SOUTHERN PINES
- SOUTHERN PINES CONDO
- STONE CREEK 44/131
- STONE CRK
- STONE CRK A-1 & A-2
- STONEYBROOK WEST
- STONEYBROOK WEST 44/134
- STONEYBROOK WEST 47/78
- STONEYBROOK WEST D
- STONEYBROOK WEST I
- STONEYBROOK WEST UN 08 I
- STONEYBROOK WEST UNIT 4 REP
- STONEYBROOK WEST UNIT 8
- STONEYBROOK WEST UT 04 48 48
- STOREY GROVE
- STOREY GROVE 50
- STOREY GROVE PH 1
- STOREY GROVE PH 1A-2
- STOREY GROVE PH 1B-1A
- STOREY GROVE PH 1B-2
- STOREY GROVE PH 1B-3
- STOREY GROVE PH 1B-4
- STOREY GROVE PH 2
- STOREY GROVE PH 4
- STOREY GROVE PH 5
- STOREY GROVE PHASE 5
- STOREY GRV PH 2
- STORY ROAD BUS PARK
- SUBURBAN SHORES
- 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/REPLAT
- 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 RESERVE
- SUNSET LAKES
- THE GROVE RESORT
- THE GROVE RESORT AND SPA CONDOMINIUM
- TILDEN PLACE/WINTER GARDEN
- TOWNHOMES WINTER GARDEN
- TRADITIONS SUB
- TRIBUTE AT OVATION
- TROYNELLE BY LAKE APOPKA
- TUCKER OAKS
- TUSCANY
- TUSCANY PH 02
- TWINWATERS
- VALENCIA SHORES
- VERDE PARK PH 1
- VILLAGE GROVE PH 01
- VILLAGE GROVE PH 02
- VILLAS/TUCKER OAKS
- WALKERS GROVE TOWNHOMES
- WALKERS GROVE TWNHMS
- WATERLEIGH
- WATERLEIGH PH 1A
- WATERLEIGH PH 1B
- WATERLEIGH PH 1C
- WATERLEIGH PH 2A
- WATERLEIGH PH 2B
- WATERLEIGH PH 2C-1
- WATERLEIGH PH 2C-2 & 2C-3
- WATERLEIGH PH 2D
- WATERLEIGH PH 2E
- WATERLEIGH PH 3A
- WATERLEIGH PH 3B & 3C
- WATERLEIGH PH 3B 3C & 3D
- WATERLEIGH PH 4A
- WATERLEIGH PH 4B & 4C
- WATERLEIGH PHASE 3A
- WATERLEIGH PHASE 4A
- WATERLEIGH PHASE 5
- WATERMARK
- WATERMARK PH 1A
- WATERMARK PH 1B
- WATERMARK PH 2A
- WATERMARK PH 2B
- WATERMARK PH 2C
- WATERMARK PH 3
- WATERMARK PH 4
- WATERMARK PHASE 4 97/87 LOT 704
- WATERSIDE – THE STRAND
- WATERSIDE ON JOHNS LAKE
- WATERSIDE/JOHNS LAKE PH 2A
- WATERSIDE/JOHNS LAKE PH 2B
- WATERSIDE/JOHNS LAKE PH 2C
- WATERSIDE/JOHNS LK-PH 2A
- WATERSIDE/JOHNS LK-PH 2B
- WEST LAKE HANCOCK ESTATES
- WESTCHESTER PLACE
- WESTFIELD LAKES
- WESTHAVEN
- WESTHAVEN AT OVATION
- WESTHAVEN/OVATION
- WESTLAKE MANOR 1ST ADD
- WESTSIDE TOWNHOMES
- WESTSIDE TOWNHOMES PH 04
- WESTSIDE TWNHMS
- WESTSIDE TWNHMS PH 02
- WESTSIDE TWNHMS-PH 05 A B & C
- WINCEY GROVES
- WINCEY GROVES PHASE 2
- WINCEY GRVS PH 2
- WINDING BAY
- WINDING BAY PH 1B
- WINDING BAY PH 2
- WINDING BAY PH 3
- WINDING BAY PRESERVE
- WINDTREE GARDENS CONDO PH 01
- WINDTREE GARDENS CONDO PH 02
- WINDTREE GARDENS CONDO PH 03
- WINDTREE GARDENS CONDO PH 04
- WINDTREE GARDENS CONDO PH 05
- WINDTREE GARDENS PH 6
- WINTER GARDEN SHORES
- WINTER GARDEN SHORES REP
- WINTER GARDEN TRLS 01-3
- WINTER GROVE
- WINTER OAKS
- WINTERMERE POINTE
- WOODBRIDGE ON GREEN
Market Summary
Current real estate data for Single Family in WINTER GARDEN as of Jun 19, 2026
863
Single Family Listed
102
Avg DOM
283
Avg $ / SqFt
$778,232
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 $283. The average listing price for Single Family in WINTER GARDEN is $778,232. To schedule a showing of MLS#o6409675 at 516 S HIGHLAND AVENUE in WINTER GARDEN, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
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 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. 516 S HIGHLAND AVENUE
WINTER GARDEN, FL