Welcome to one of Windermere’s finest offerings — an impressive 5-bedroom, 4.5-bath estate spanning almost 6,000 sq ft on a premium 0.62-acre direct water-view lot in the exclusive 24-hour guard-gated community of Tildens Grove. This is a luxury build that combines sophistication with fun and accommodates an active lifestyle for family and entertaining: a custom private movie theater, resort-style pool with spa and panoramic screen overlooking the water, gourmet kitchen, a dedicated gym, plus two generous family / entertainment spaces upstairs and down… all create a floor plan that handles both grand entertaining and relaxed everyday living. Updates to HVAC, lighting, fixtures, media systems, and wood flooring throughout. Soaring ceilings with architectural features, and elegant architectural details define every room. Bedroom layout creates a lot of options with one of the downstairs bedrooms featuring a separate side entry just off of the driveway with direct access to a full bathroom – ideal for guests and multi-generational living. Three-car garage, paver driveway, lush mature landscaping. Tildens Grove offers larger homesites and amenities including tennis, pickleball, basketball, playground, and a scenic park. Minutes to Disney World, Restaurant Row, Windermere Chain of Lakes boat ramp access, top-rated schools, quick SR-429 access for easy day trips to the beach, and approximately 30 minutes to Orlando International Airport. Luxury, privacy, and convenience — all in one remarkable home. Owners have this priced right so don’t delay in setting up your private showing today.
Property Details
Price:
$1,999,900
MLS #:
O6402594
Status:
Active
Beds:
5
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
TILDENS GROVE PH 01 47/65
Neighborhood:
34786windermere
Listed Date:
May 1, 2026
Finished Sq Ft:
5,922
Total Sq Ft:
7,592
Lot Size:
27,126 sqft / 0.62 acres (approx)
Year Built:
2005
See this Listing
Schools
Elementary School:
Windermere Elem
Middle School:
Bridgewater Middle
High School:
Windermere High School
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Ceramic Tile, Engineered Hardwood
Heating
Electric
Interior Features
Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Coffered Ceiling(s), Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Walk-In Closet(s), Wet Bar, Window Treatments
Laundry Features
Inside
Levels
Two
Exterior
Architectural Style
Contemporary, Custom
Attached Garage YN
1
Community Features
Deed Restrictions, Gated Community – Guard, Golf Carts OK, Park, Playground, Sidewalks, Tennis Court(s)
Construction Materials
Block, Concrete
Covered Spaces
3
Direction Faces
Southeast
Exterior Features
Balcony, Irrigation System, Outdoor Kitchen, Private Entrance, Private Mailbox, Private Yard, Storage
Fencing
Fenced
Garage Spaces
3
Lot Features
Landscaped, Level, Oversized Lot, Private, Sidewalk
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener, Garage Faces Side, Guest, Oversized
Patio And Porch Features
Covered, Enclosed, Front Porch, Screened
Roof
Concrete, Tile
Security Features
Gated Community, Security Gate, Security System, Smoke Detector(s)
Spa Features
Heated, In Ground
View
Water
Financial
HOA Fee
$950
HOA Fee Frequency
Quarterly
HOA Includes
24-Hour Guard, Recreational Facilities, Security
HOA Name
Angela Timmons
HOA Phone
407-333-7787
Tax Year
2025
Taxes
$17,783
Map
Community
- Address5421 TILDENS GROVE BOULEVARD WINDERMERE FL
- SubdivisionTILDENS GROVE PH 01 47/65
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ACREAGE
- ALADAR ON LAKE BUTLER
- ASHLIN FARK PH 2
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- ASHLIN PK PH 2
- BELLARIA
- BELMERE VILLAGE G-5
- 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
- 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 01
- KEENES POINTE UNIT 1
- KEENES POINTE UNIT 7
- KEENES POINTE UNIT 9
- KEENES POINTE UT 04 SEC 31 48 82
- 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 DAVIS RESERVE A & B
- LAKE DOWN ESTATES
- LAKE DOWN POINTE 50 42
- LAKE DOWN RESERVE
- LAKE DOWN SHORES REP
- 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
- 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
- LANDINGS AT LAKE SAWYER
- 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 PHASE IV
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- ROBERTS LANDING
- ROSSER RESERVE REP
- ROYAL ESTATE
- ROYAL ESTATES
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SHORES SUB
- SAWYER SOUND
- SILVER WOODS
- SILVER WOODS PH 03
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT BEACH
- SUMMERPORT PH 03
- SUMMERPORT PH 05
- SUMMERPORT PH 1
- SUMMERPORT PHASE 4
- SUNSET BAY
- 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
- 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
- WINDEMERE SOUND PH 2
- WINDEMERE TRLS PH 3B
- WINDERMERE
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- 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 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
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of May 10, 2026
291
Single Family Listed
94
Avg DOM
470
Avg $ / SqFt
$2,326,866
Avg List Price
Property Summary
- Located in the TILDENS GROVE PH 01 47/65 subdivision, 5421 TILDENS GROVE BOULEVARD WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $1,999,900 and features 5 beds, 5 baths, and has approximately 5,922 square feet of living space, and was originally constructed in 2005. The current price per square foot is $338. The average price per square foot for Single Family listings in WINDERMERE is $470. The average listing price for Single Family in WINDERMERE is $2,326,866. To schedule a showing of MLS#o6402594 at 5421 TILDENS GROVE BOULEVARD in WINDERMERE, FL, contact your WINDERMERE INTERNATIONAL REALTY agent at 4079901329.
Similar Listings Nearby
Courtesy of DERENTHAL REALTY. 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. 5421 TILDENS GROVE BOULEVARD
WINDERMERE, FL
