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This expansive two-story residence offers beautifully connected gathering spaces, multiple private retreats, and flexible rooms that adapt to your lifestyle.
As you arrive, a welcoming entry and foyer set the tone for the home’s inviting layout. Just off the entrance, a dedicated office provides the ideal work-from-home space, library, or quiet study. Beyond the foyer, the floor plan opens into a spacious formal living room that creates a warm first impression and offers a natural transition into the heart of the home.
At the center of the first floor, the kitchen is perfectly positioned for both daily life and entertaining, complete with a walk-in pantry, a generously sized island for seating, and a seamless connection to a separate dining room, providing an elegant setting for holidays, celebrations, and dinner parties. Natural lighting streams through multiple windows in the breakfast nook, which overlooks the outdoor living area, offering the perfect spot for casual morning coffee or relaxed meals. The family room creates an open concept gathering space where conversation flows effortlessly and allows for easy entertaining.
A thoughtfully placed half bath with access to the outdoor patio area adds easy accessibility for guests and family alike, and the attached garage offers convenient parking and direct entry into the living space, enhancing both functionality and comfort.
Upstairs, the home continues to impress with a thoughtfully designed second floor. The private primary suite is a true retreat, featuring generous proportions, multiple closet spaces, and a spa-inspired bath designed for relaxation.
Two bedrooms provide comfort and privacy for siblings and share a Jack and Jill bathroom. An additional bedroom is ideal for family or guests with access to a covered balcony, creating a private outdoor escape to enjoy Florida evenings.
A spacious flex room offers endless possibilities to create a home theater, game room, fitness studio, second office, or guest retreat to fit your needs. Completing the upper level is a third full bathroom with a walk-in shower and a laundry room, adding everyday convenience right where you need it most.
Step outside to one of the home’s standout features, an oversized covered lanai and expansive brick-paver patio designed for true Florida outdoor living. Ample space for multiple seating and dining areas, this private backyard retreat is ideal for entertaining, weekend gatherings, outdoor dining, or simply relaxing under the shade of mature trees. Lush landscaping, privacy fencing, and natural greenery create a peaceful setting with room to enjoy year-round outdoor living.
Residents enjoy a beautifully designed central gathering area featuring the community’s amenity center, resort-style pool, basketball court, playground, expansive open green space, and connected sidewalks for walking. The location is convenient, with nearby shopping, dining, and everyday essentials just minutes away at Westside Shoppes, Lakeside Village, and Windermere Village, plus additional retail and dining options throughout the surrounding Windermere area.
This expansive two-story residence offers beautifully connected gathering spaces, multiple private retreats, and flexible rooms that adapt to your lifestyle.
As you arrive, a welcoming entry and foyer set the tone for the home’s inviting layout. Just off the entrance, a dedicated office provides the ideal work-from-home space, library, or quiet study. Beyond the foyer, the floor plan opens into a spacious formal living room that creates a warm first impression and offers a natural transition into the heart of the home.
At the center of the first floor, the kitchen is perfectly positioned for both daily life and entertaining, complete with a walk-in pantry, a generously sized island for seating, and a seamless connection to a separate dining room, providing an elegant setting for holidays, celebrations, and dinner parties. Natural lighting streams through multiple windows in the breakfast nook, which overlooks the outdoor living area, offering the perfect spot for casual morning coffee or relaxed meals. The family room creates an open concept gathering space where conversation flows effortlessly and allows for easy entertaining.
A thoughtfully placed half bath with access to the outdoor patio area adds easy accessibility for guests and family alike, and the attached garage offers convenient parking and direct entry into the living space, enhancing both functionality and comfort.
Upstairs, the home continues to impress with a thoughtfully designed second floor. The private primary suite is a true retreat, featuring generous proportions, multiple closet spaces, and a spa-inspired bath designed for relaxation.
Two bedrooms provide comfort and privacy for siblings and share a Jack and Jill bathroom. An additional bedroom is ideal for family or guests with access to a covered balcony, creating a private outdoor escape to enjoy Florida evenings.
A spacious flex room offers endless possibilities to create a home theater, game room, fitness studio, second office, or guest retreat to fit your needs. Completing the upper level is a third full bathroom with a walk-in shower and a laundry room, adding everyday convenience right where you need it most.
Step outside to one of the home’s standout features, an oversized covered lanai and expansive brick-paver patio designed for true Florida outdoor living. Ample space for multiple seating and dining areas, this private backyard retreat is ideal for entertaining, weekend gatherings, outdoor dining, or simply relaxing under the shade of mature trees. Lush landscaping, privacy fencing, and natural greenery create a peaceful setting with room to enjoy year-round outdoor living.
Residents enjoy a beautifully designed central gathering area featuring the community’s amenity center, resort-style pool, basketball court, playground, expansive open green space, and connected sidewalks for walking. The location is convenient, with nearby shopping, dining, and everyday essentials just minutes away at Westside Shoppes, Lakeside Village, and Windermere Village, plus additional retail and dining options throughout the surrounding Windermere area.
Property Details
Price:
$690,000
MLS #:
O6406997
Status:
Pending
Beds:
5
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
PRESTON SQUARE
Neighborhood:
34786windermere
Listed Date:
May 14, 2026
Finished Sq Ft:
3,390
Total Sq Ft:
4,480
Lot Size:
6,165 sqft / 0.14 acres (approx)
Year Built:
2011
Pool34786 – Windermere34786windermerePreston SquareSunset Park ElemHorizon West Middle SchoolWindermere High SchoolBuyer Is Responsible For Verifying With Hoa, City And/or County Ordinances Regarding All Leasing Restrictions.No MinimumPets Allowed
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Schools
Elementary School:
Sunset Park Elem
Middle School:
Horizon West Middle School
High School:
Windermere High School
Interior
Appliances
Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Ceramic Tile, Luxury Vinyl, Porcelain Tile
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Solid Surface Counters, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry Features
Laundry Room
Levels
Two
Exterior
Association Amenities
Basketball Court, Park, Playground, Pool, Recreation Facilities, Trail(s)
Attached Garage YN
1
Community Features
Park, Playground, Pool, Sidewalks
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
South
Exterior Features
Balcony, French Doors, Irrigation System, Lighting, Private Mailbox, Sidewalk
Garage Spaces
2
Lot Features
Flag Lot, In County, Landscaped, Sidewalk
Open Parking YN
1
Parking Features
Covered, Driveway, Ground Level
Patio And Porch Features
Covered, Front Porch, Patio, Rear Porch
Roof
Shingle
Financial
HOA Fee
$99
HOA Fee Frequency
Monthly
HOA Includes
Community Pool, Pool Maintenance, Recreational Facilities
HOA Name
Jedi Management
HOA Phone
689-204-2057
Tax Year
2025
Taxes
$605
Map
Community
- Address6615 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
- BELLARIA
- BELMERE VILLAGE G2 48 65
- BELMERE VILLAGE G5
- BUTLER BAY
- CARRINGTON
- CASA DEL LAGO REP
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- CREEKS RUN
- DAVIS SHORES
- DIAMONDHEAD
- DOWN POINT SUB
- EDEN’S HAMMOCK
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE AT BERKSHIRE PARK
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTANCIA/WINDERMERE
- ESTATES AT WINDERMERE
- FARMS
- GARDENS OF ISLEWORTH
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- HARBOR ISLE
- ISLEWORTH
- ISLEWORTH WEST
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 1
- KEENES POINTE UNIT 9
- KEENES POINTE UT 06 50 95
- KELSO ON LAKE BUTLER
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #35 36
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUTLER PARK PT REP
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CRESCENT RESERVE
- LAKE DOWN ESTATES
- LAKE DOWN RESERVE
- LAKE DOWN SHORES REP
- LAKE REAMS TOWNHOMES
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 02
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 05
- LAKE SAWYER SOUTH PH 1
- LAKE SAWYER SOUTH PH 3
- LAKES
- LAKES OF WINDERMERE PH 2A
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE LAKE REAMS
- LAKES/WINDERMERE LAKE REAMS TWNH
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 03 P & Q
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE AT LAKES OF WINDERMERE CONDO PH 3
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE A CONDO
- LAKESIDE/LKS/WINDERMERE PH 3
- LEGADO
- MARINA BAY ESTATES
- MERRICK LNDG
- METCALF PARK REP
- OASIS COVE 2 AT LAKESIDE VILAGE
- OASIS COVE AT LAKE SIDE
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE PH
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- RESERVE AT BELMERE
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PH 03 51 01
- RESERVE AT BELMERE PHASE IV
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- ROBERTS LANDING
- ROYAL ESTATE
- ROYAL ESTATES
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SHORES SUB
- SAWYER SOUND
- SILVER WOODS PH 02
- SILVER WOODS PH 03
- SILVER WOODS PH 04
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT BEACH
- SUMMERPORT PH 03
- SUMMERPORT PH 05
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TUSCANY RIDGE 50 141
- VINEYARDS/HORIZONS WEST PH 1A
- VINEYARDS/HORIZONS WEST PH 1B
- VINEYARDS/HORIZONS WEST PH 2A
- VINEYARDS/HORIZONS WEST PH 2B
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERSTONE
- WATERSTONE A D E F G H J L
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WEST POINT COMMONS
- WESTOVER CLUB PH 01 44/139
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WILLOWS AT LAKE RHEA PH 02
- WILLOWS AT LAKE RHEA PH 03
- WINDEMERE SOUND PH 2
- WINDEMERE TRLS PH 3B
- WINDERMERE
- WINDERMERE DOWNS
- WINDERMERE DOWNS PH 03
- WINDERMERE ISLE
- WINDERMERE ISLE-PH 2
- WINDERMERE LANDINGS
- WINDERMERE LANDINGS PH 2
- WINDERMERE LNDGS FD-1
- WINDERMERE LNDGS PH 02
- WINDERMERE POINTE
- WINDERMERE REP
- WINDERMERE RESERVE
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PHASE 5A 80/102 LOT 39
- WINDERMERE TRLS PH 1A
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH 5A
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of Jun 09, 2026
289
Single Family Listed
99
Avg DOM
481
Avg $ / SqFt
$2,425,703
Avg List Price
Property Summary
- Located in the PRESTON SQUARE subdivision, 6615 HELMSLEY CIRCLE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $690,000 and features 5 beds, 4 baths, and has approximately 3,390 square feet of living space, and was originally constructed in 2011. The current price per square foot is $204. The average price per square foot for Single Family listings in WINDERMERE is $481. The average listing price for Single Family in WINDERMERE is $2,425,703. To schedule a showing of MLS#o6406997 at 6615 HELMSLEY CIRCLE in WINDERMERE, FL, contact your Preferred Real Estate Brokers agent at 4076987254.
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Courtesy of EXP REALTY 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 Preferred Real Estate Brokers include the name of the listing broker. Neither the listing company nor Preferred Real Estate Brokers 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. 6615 HELMSLEY CIRCLE
WINDERMERE, FL





