Immaculately maintained, move in ready, 4 bed, 3 bath family home in the highly sought after Preston Square community, an established Windermere community. The home feels warm and welcoming, but also luxurious with the 10ft ceilings, crown molding and plantation shutters. The kitchen features a dining area and boasts upgraded appliances, granite countertops and 42″ cabinets. The primary bedroom is conveniently located on the first floor, a lovely refuge with tray ceiling, large walk in closet with built ins and en suite bathroom. The large upstairs bedroom, bathroom and bonus room would make a great teenager space, in law suite or entertainment area. Roof was replaced in 2022 and to save on high power bills, a complete, FULLY PAID, solar system installed in 2023!! Other upgrades include new interior paint and light fixtures in 2025, exterior painted in 2019 and a water purification system. For easy maintenance, the sod in the back yard has been replace with turf, is fully fenced and has a spacious screened patio – a serene, private place to relax with your favorite coffee or cocktail! Located in a top-rated school district and zoned for Windermere High School, this home combines luxury, convenience, and peace of mind in one of Central Florida’s most desirable communities. square has a charming atmosphere and features its own community pool, park, playground and sport court, all located just minutes from shopping, dining, and theme parks. A short drive to historic Windermere Town with its weekly farmers market, monthly food carts, historic town hall and old school house. Don’t miss the opportunity to live the Florida lifestyle in this gorgeous home located within a great school district!
Property Details
Price:
$635,000
MLS #:
S5151342
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
PRESTON SQUARE
Neighborhood:
34786windermere
Listed Date:
Jun 11, 2026
Finished Sq Ft:
2,575
Total Sq Ft:
3,293
Lot Size:
5,500 sqft / 0.13 acres (approx)
Year Built:
2009
See this Listing
Schools
Interior
Appliances
Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Solar Hot Water Owned, Washer, Water Filtration System
Bathrooms
3 Full Bathrooms
Cooling
Central Air, Zoned
Flooring
Carpet, Tile
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Tray Ceiling(s), Walk-In Closet(s), Window Treatments
Laundry Features
Laundry Room
Levels
Two
Exterior
Association Amenities
Clubhouse, Park, Playground, Pool
Attached Garage YN
1
Community Features
Clubhouse, Deed Restrictions, Park, Playground, Pool
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
North
Exterior Features
Irrigation System, Sidewalk, Sliding Doors, Sprinkler Metered
Fencing
Vinyl
Garage Spaces
2
Roof
Shingle
Financial
HOA Fee
$129
HOA Fee Frequency
Monthly
HOA Includes
Community Pool, Recreational Facilities
HOA Name
Vanguard Mgt Group – Nadia Reveron
HOA Phone
813 930 8036
Tax Year
2025
Taxes
$4,553
Map
Community
- Address6558 HELMSLEY CIRCLE WINDERMERE FL
- SubdivisionPRESTON SQUARE
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ACREAGE
- ALADAR ON LAKE BUTLER
- ASHLIN FARK PH 2
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- BELLA VITA ESTATES
- BELLARIA
- BELMERE VILLAGE
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BELMERE VILLAGE G4 50 58
- BELMERE VLG G2
- BUTLER BAY
- BUTLER BAY / LAKE CRESCENT RESERVE
- BUTLER RIDGE
- CARRINGTON
- CASA DEL LAGO REP
- CASA DEL LAGO-REPLAT
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- CREEKS RUN
- DOWN ACRES ESTATES
- DOWN POINT SUB
- DOWNS COVE CAMP SITES
- EDEN’S HAMMOCK
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE AT WINDERMERE LANDING
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTATES AT WINDERMERE
- FARMS
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- ISLEWORTH
- ISLEWORTH 01 AMD
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 03 46/104
- KEENES POINTE UNIT 1
- KEENES POINTE UNIT 7
- KEENES POINTE UNIT 9
- KEENES POINTE UT 06 50 95
- LAKE BURDEN
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #79/32 LOT 223
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CRESCENT RESERVE
- LAKE CRESENT RESERVE
- LAKE DAVIS ESTATES
- LAKE DOWN ESTATES
- LAKE DOWN RESERVE
- LAKE HANCOCK SHORES
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 3
- LAKE SAWYER SOUTH PH 5
- LAKES
- LAKES OF WINDERMERE PH 1
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE PH 3
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE AT LAKES OF WINDERMERE CONDO PH 3
- LAKESIDE VILLAGE TWNHMS
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE CONDO
- LAKESIDE/LKS/WINDERMERE PH 10
- LAKESIDE/LKS/WINDERMERE PH 3
- LAKESIDE/LKS/WINDERMERE PH 4
- LAKESIDE/LKS/WINDERMERE PH 9
- LEGADO
- LES TERRACES
- MARINA BAY ESTATES
- METCALF PARK REP
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE
- OASIS COVE II/LAKESIDE VILLAGE PH
- OASIS COVE II/LAKESIDE VILLAGE UN
- OXFORD MOOR 47/30
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- PROVIDENCE PH 2
- RESERVE AT BELMERE
- RESERVE AT BELMERE PH 02
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PHASE IV
- RESERVE AT LAKE BUTLER
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND 45/120
- RESERVE AT LAKE BUTLER SOUND UNIT 02
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- RESERVE/BELMERE PH 04
- ROBERTS LANDING
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SOUND
- SILVER WOODS PH 01
- SILVER WOODS PH 02
- SILVER WOODS PH 03A
- SILVER WOODS PH 04
- SOUTHBRIDGE VILLAGE
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT PH 02
- SUMMERPORT PH 03
- SUMMERPORT PH 04 C E F & G
- SUMMERPORT PH 05
- SUMMERPORT PH 5
- SUMMERPORT PHASE 1
- SUMMERPORT TRAIL PH 2
- SUMMERPORT TRL
- SUNSET BAY
- TENNYSON PK/SUMMERPORT
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TUSCANY RIDGE 50 141
- VINEYARDS/HORIZONS WEST PH 1B
- VINEYARDS/HORIZONS WEST PH 2A
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERSTONE
- WATERSTONE A D E F G H J L
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WEST LAKE BUTLER ESTATES
- WEST POINT COMMONS
- WESTOVER CLUB
- WESTOVER CLUB PH 02 REP
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WINDEMERE SOUND PH 2
- WINDERMERE
- WINDERMERE DOWNS
- WINDERMERE DOWNS PH 03
- WINDERMERE GRANDE
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE LNDGS PH 02
- WINDERMERE POINTE
- WINDERMERE POINTE AT LAKE ROPER
- WINDERMERE RESERVE
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PH 3B
- WINDERMERE TRAILS PHASE 1C 80/15 LOT 113
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH IA
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of Jun 13, 2026
287
Single Family Listed
100
Avg DOM
478
Avg $ / SqFt
$2,439,553
Avg List Price
Property Summary
- Located in the PRESTON SQUARE subdivision, 6558 HELMSLEY CIRCLE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $635,000 and features 4 beds, 3 baths, and has approximately 2,575 square feet of living space, and was originally constructed in 2009. The current price per square foot is $247. The average price per square foot for Single Family listings in WINDERMERE is $478. The average listing price for Single Family in WINDERMERE is $2,439,553. To schedule a showing of MLS#s5151342 at 6558 HELMSLEY CIRCLE in WINDERMERE, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
Similar Listings Nearby
Courtesy of WATSON REALTY CORP.. 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. 6558 HELMSLEY CIRCLE
WINDERMERE, FL

