105 Pine St
Windermere, FL 34786
- 5 Beds
- 5.5 Baths
- 5,696 sqft (on 0.57 acres)
5 Beds
5.5 Baths
5,696 sqft
(on 0.57 acres)
Local Information
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Description
Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of Lakes. Set on an oversized, over half-acre corner lot in downtown Windermere, this custom home offers a rare blend of privacy, flexibility, and walkability to local dining, coffee shops, boutiques, and the weekly farmers market. Built in 2015 and thoughtfully expanded, this 5,696 square foot home features five bedrooms and five and a half bathrooms, including a fully separate casita ideal for in-law living, guests, or private quarters. From the moment you arrive, fresh landscaping and an exposed brick front porch create a warm and inviting entrance. Inside, the open living space is both spacious and comfortable, with high ceilings, wood beams, crown molding, and a gas fireplace, complemented by shiplap and exposed brick accents. The kitchen opens seamlessly to the main living area and overlooks the backyard, featuring a large Cambria quartz island, Kohler farm sink, walk-in pantry, Bosch double ovens, Viking gas cooktop, custom hood, LG refrigerator, soft-close cabinetry, under-cabinet lighting, and a dedicated coffee bar. The primary suite offers peaceful backyard views, two custom walk-in closets, and a well-appointed bath with dual vanities, a makeup station, a garden tub, and a large walk-in shower with floor-to-ceiling tile and dual showerheads. Additional bedrooms are thoughtfully placed, including one with an ensuite bath. A versatile flex room with a coffered ceiling, storage, and its own laundry setup connects to a private office with built-ins and a walk-in closet. A secondary primary suite provides a comfortable space for extended family or guests. In total, the home offers three separate laundry areas for added convenience. Outdoor living is designed for true Florida living. Two sets of sliding glass doors, including one from the flex room, open to a covered lanai with wood plank ceiling and fans, along with a fully equipped summer kitchen featuring an Artisan natural gas grill, vent hood, sink, and icemaker. The space extends to an expansive paver patio surrounding a heated saltwater pool and spa with water features, all overlooking a large fenced backyard. The casita, completed in 2023 and offering over 1,200 square feet, lives like a private residence with its own entrance and Spanish Mediterranean character, including wood beams, hardwood flooring, and a Kiva-style fireplace. It features a full living room, a kitchen with GE Café appliances and a quartz island, and a spacious bedroom suite with a custom walk-in closet and a beautifully finished bath. A screened lanai and separate fenced yard provide added privacy. A three-car garage with high ceilings includes an oversized RV-height door, 50-amp plug, and space for additional storage or lifts, along with a third laundry area. Additional features include dual AC systems, tankless water heaters, and a Generac generator. Residents of Windermere enjoy private access to the Butler Chain of Lakes, parks, tennis courts, and a boat ramp, all golf cart accessible. Golf cart friendly with tree-lined streets and a true small-town feel. No HOA and conveniently located near top-rated schools, major roadways, and world-class dining and entertainment. This is a truly unique Windermere home designed for modern multigenerational living. Schedule your private showing today!
Home Highlights
Parking
3 Car Garage
Outdoor
Porch, Patio, Deck, Pool
View
Pool, Water, Lake
HOA
None
Price/Sqft
$439
Listed
14 days ago
Home Details for 105 Pine St
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Interior Details Number of Rooms: 13Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Primary Bathroom, Bonus Room, Dining Room, Kitchen, Living Room, Office |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 5696 Square Feet |
Appliances & Utilities Utilities: Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Sprinkler Well, Street Lights, Water ConnectedAppliances: Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Range, Range Hood, Refrigerator, Tankless Water Heater, WasherDishwasherDisposalDryerLaundry: In Garage,Inside,Laundry Closet,Laundry RoomRefrigeratorWasher |
Heating & Cooling Heating: Central,Electric,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central |
Fireplace & Spa Fireplace: Family Room, Gas, Other RoomSpa: Heated, In GroundHas a FireplaceHas a Spa |
Gas & Electric Has Electric on Property |
Windows, Doors, Floors & Walls Window: Blinds, Window TreatmentsDoor: Outdoor Kitchen, Sliding DoorsFlooring: Ceramic Tile, Luxury Vinyl, Tile, Hardwood |
Levels, Entrance, & Accessibility Stories: 1Levels: OneFloors: Ceramic Tile, Luxury Vinyl, Tile, Hardwood |
View Has a ViewView: Pool, Water, Lake |
Security Security: Security System Owned, Smoke Detector(s) |
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Exterior Home Features Roof: ShinglePatio / Porch: Covered, Deck, Front Porch, Patio, Rear Porch, ScreenedFencing: Fenced, Other, VinylVegetation: Mature Landscaping, Oak Trees, Trees/LandscapedOther Structures: Guest House, Outdoor KitchenExterior: Irrigation System, Lighting, Outdoor Kitchen, Private Mailbox, Rain GuttersFoundation: SlabHas a Private Pool |
Parking & Garage Number of Garage Spaces: 3Number of Covered Spaces: 3Other Parking: Garage Dimensions: 40x24No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Boat,Driveway,Garage Door Opener,Garage Faces Side,Golf Cart Parking,Oversized,RV Garage |
Pool Pool: Gunite, Heated, In Ground, Salt WaterPool |
Frontage Waterfront: Lake Privileges, Skiing AllowedRoad Frontage: Private RoadResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Dirt, Other, PavedNot on Waterfront |
Water & Sewer Sewer: Septic TankWater Body: BUTLER CHAIN OF LAKES |
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Cumulative Days on Market: 9Days on Market: 14 |
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Year Built Year Built: 2015 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Custom,Florida,Other,Mediterranean,Traditional |
Building Construction Materials: Block, Concrete, StuccoNot a New ConstructionNot Attached PropertyNo Additional Parcels |
Property Information Condition: CompletedParcel Number: 172328933705000 |
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Price List Price: $2,500,000Price Per Sqft: $439 |
Status Change & Dates Off Market Date: Sat May 16 2026Possession Timing: Close Of Escrow |
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MLS Status: Pending |
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Direction & Address City: WINDERMERECommunity: WINDERMERE |
School Information Elementary School: Windermere ElemJr High / Middle School: Gotha MiddleHigh School: Olympia High |
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Listing Agent Listing ID: O6405163 |
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Building Details Builder Name: Robert Heinz/Heinz Group |
Building Area Building Area: 7296 Square Feet |
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Not Senior Community |
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Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee |
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Lot Area: 0.57 acres |
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Special Conditions: None |
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Listing Terms: Cash, Conventional, VA Loan |
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Business Information Ownership: Fee Simple |
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Mls Number: O6405163Water ViewWater View: Water, LakeShowing Advance Notice: 24Showing AttendedShowing Considerations: Pet(s) on PremisesShowing Requirements: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12095-N-172328933705000-R-N |
Last check for updates: 1 day ago
Listing Provided by: Tiffany Pantozzi, (407) 955-9716
ALIGN REAL ESTATE LLC, (305) 389-2922
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6405163

Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511
Price History for 105 Pine St
| Date | Price | Event | Source |
|---|---|---|---|
| 05/19/2026 | $2,500,000 | Pending | Stellar MLS #O6405163 |
| 05/08/2026 | $2,500,000 | Listed For Sale | Stellar MLS #O6405163 |
| 04/25/2025 | $2,285,000 | Sold | Stellar MLS #O6279246 |
| 04/04/2025 | $2,495,000 | Pending | Stellar MLS #O6279246 |
| 03/07/2025 | $2,495,000 | PriceChange | Stellar MLS #O6279246 |
| 02/13/2025 | $2,750,000 | Listed For Sale | Stellar MLS #O6279246 |
| 06/27/2014 | $325,000 | Sold | N/A |
| 10/22/2013 | $500,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $12,929 |
| Assessment | $1,070,328 |
Home facts updated by county records
Comparable Sales for 105 Pine St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.06 | Single-Family Home | $2,250,000 | 03/09/26 | 5 | 4.5 | 4,688 | |
0.30 | Single-Family Home | $2,400,000 | 09/05/25 | 5 | 4.5 | 5,111 | |
0.30 | Single-Family Home | $4,125,000 | 09/05/25 | 5 | 5 | 4,783 | |
0.43 | Single-Family Home | $3,100,000 | 09/02/25 | 4 | 3.5 | 3,923 | |
0.66 | Single-Family Home | $2,065,000 | 07/14/25 | 5 | 4 | 3,950 | |
0.44 | Single-Family Home | $2,700,000 | 07/30/25 | 3 | 2.5 | 3,469 | |
0.28 | Single-Family Home | $862,000 | 01/08/26 | 4 | 3 | 2,410 | |
0.88 | Single-Family Home | $2,171,470 | 04/29/26 | 5 | 4.5 | 3,994 | |
0.74 | Single-Family Home | $1,700,000 | 10/10/25 | 4 | 4.5 | 3,670 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 105 Pine St.
What Locals Say about Windermere
At least 270 Trulia users voted on each feature.
93 % Say it's dog friendly
92 % Say there are sidewalks
87 % Say car is needed
87 % Say parking is easy
81 % Say people would walk alone at night
80 % Say it's quiet
79 % Say there's holiday spirit
78 % Say kids play outside
75 % Say streets are well-lit
64 % Say yards are well-kept
60 % Say they plan to stay for at least 5 years
59 % Say it's walkable to grocery stores
56 % Say there's wildlife
55 % Say it's walkable to restaurants
54 % Say neighbors are friendly
40 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Tiffany Pantozzi, ALIGN REAL ESTATE LLC, (305) 389-2922
Agent Phone: (407) 955-9716

105 Pine St, Windermere, FL 34786 is a 5 bedroom, 6 bathroom, 5,696 sqft single-family home built in 2015. This property is currently available for sale and was listed by Stellar MLS on May 8, 2026. The MLS # for this home is MLS# O6405163.

