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Single family home for sale at 263 Deer Isle Dr, Winter Garden, FL 34787 | MLS# O6440044 | Listing updated on 2026-09-17
Photo 1 of Single family home for sale at 263 Deer Isle Dr, Winter Garden, FL 34787 | MLS# O6440044 | Listing updated on 2026-09-17
Photo 2 of Single family home for sale at 263 Deer Isle Dr, Winter Garden, FL 34787 | MLS# O6440044 | Listing updated on 2026-09-17
Photo 3 of Single family home for sale at 263 Deer Isle Dr, Winter Garden, FL 34787 | MLS# O6440044 | Listing updated on 2026-09-17
Photo 4 of Single family home for sale at 263 Deer Isle Dr, Winter Garden, FL 34787 | MLS# O6440044 | Listing updated on 2026-09-17
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$1,495,000

Monthly Est:$7,441

  • Beds Icon3 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,735sqft

263 Deer Isle Dr, Winter Garden, FL 34787

$7,441/moEst:

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  • Single Family Residence

  • Built in 1988

  • $246.83/mo HOA

  • 42,004 sqft lot

  • $547/sq.ft

Description

Under contract-accepting backup offers. Welcome home! This turnkey, exquisite custom home enables you to wake up to shimmering water views of Johns Lake and step into the lakefront lifestyle you’ve been dreaming of. On an acre in a gated community, sellers spared no expense on a complete renovation— exterior to interior and down to the studs. New windows, high end finishes, and designer details in every room rival new construction. Upon entering, you’ll be captivated by an abundance of natural light, soaring ceilings and panoramic water views. The foyer leads to the spacious living/office/flex space and dining room with stunning dry bar and 180+ bottle wine fridge. The large family room with fireplace feature wall and bay window adjoins the true gourmet kitchen for open concept living, overlooking the lake and community pond with lighted fountain. A chef’s kitchen features tall kitchen cabinets for extra storage, massive center island, large sink, Fisher and Paykel double-drawer dishwasher, Scotsman pellet icemaker. The all Viking appliance pkg includes a 36” refrigerator with 30” freezer, dbl ovens, warming drawer, 6 burner induction stove top. A plumbed, built-in Miele espresso machine provides your favorite morning coffee, hot water, and more. A reverse osmosis water filtration system feeds the kitchen sink, icemakers, coffee machine. The sunroom boasts two walls of new Pella hurricane rated slider doors that flood the home with natural light and frame the stunning waterfront scenery and provides a seamless connection between indoor and outdoor living opening onto the sandstone lanai with oversized resort style sparkling saltwater pool, spa and waterfall. The lanai roof structure is unique in that the vaulted roof and screening provides all weather protection to the pool, built in bar and overflow patio area allowing for entertaining in any weather or watching the Disney fireworks or rocket launches. The lanai is outfitted with 3 large DC ceiling fans and integrated watering system. Spacious primary bedroom with lanai access overlooks the lake and boasts a spa-like bathroom with dual vanities, frameless zero entry shower, free-standing tub and large walk-in closet. The split bedroom plan allows for maximum privacy. Secondary bedrooms are spacious with oversized closets. The exterior, with its professional landscape design and lighting, is designed for play, relaxation and beauty. Enjoy direct access to Johns Lake and spend your days boating, jet skiing, kayaking, paddle boarding, fishing or simply relaxing. A paver walkway from the house leads to the expansive back yard, beachfront, and large fire pit area, perfect for play and entertaining. Private dock with remote boat lift and double jet ski lift allows for lake enjoyment with effortless access. Dock is equipped with running water, lights and no/low maintenance composite decking and handrails. The deep garage is oversized with storage racks and an additional air-conditioned bonus space to be used as a craft/exercise room/home office or air-conditioned storage. Neighborhood amenities include community dock, boat ramp, tennis/pickleball court, basketball court, cable/internet. Conveniently and centrally located with easy access to the Turnpike, 429, 408, downtown Winter Garden and Orlando, the airport, Disney, Universal and area attractions. Minutes to restaurants, shops, hospitals, West Orange Trail.

  • Houzeo last checked: 5 hours ago
  • Listing updated: September 17, 2026 at 4:33 pm
  • Listing Provided by: Ronald Haywood (321) 888-7740 | BHHS FLORIDA REALTY (407) 876-2090
  • Source: Stellar MLS-FL | MLS#: O6440044 Stellar MLS-FL

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    1

  • County

    Orange County

  • City

    Winter Garden

  • Neighborhood

    --

  • Year Built

    1988

  • HOA Fees

    $246.83/mo

  • Finished Area

    2,735 sqft

  • Lot Size

    42,004 sqft lot

  • Basement Area

    - sqft

  • MLS Name

    Stellar MLS

  • MLS Number

    O6440044

  • MLS Status

    Pending

  • Days on Market

    38

  • Cumulative Days on Market

    2

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Location

HOA Management

Sentry Management

HOA Fees

$1,481.45/ Semi-Annually

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Security Gate Security Gate

Basket Ball Basket Ball

Internet Internet

Tennis Tennis

Cable TV Cable TV

Sports Court Sports Court

Escrow Reserves Fund Escrow Reserves Fund

Common Area Taxes Common Area Taxes

Private Road Private Road

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 3

    Bathrooms: 3

  • Great Room

    Level: First

    Area: 210.00 Square Feet

    Dimensions: 15x14

  • Kitchen

    Level: First

    Area: 272.00 Square Feet

    Dimensions: 17x16

  • Primary Bedroom

    Level: First

    Area: 252.00 Square Feet

    Dimensions: 21x12

  • Den

    Level: First

    Area: 176.00 Square Feet

    Dimensions: 16x11

  • Dining Room

    Level: First

    Area: 169.00 Square Feet

    Dimensions: 13x13

  • Bedroom 3

    Level: First

    Area: 135.00 Square Feet

    Dimensions: 13.5x10

  • Bedroom 2

    Level: First

    Area: 187.65 Square Feet

    Dimensions: 13.5x13.9

  • Florida Room

    Level: First

    Area: 747.98 Square Feet

    Dimensions: 25.1x29.8

  • Balcony/Porch/Lanai

    Level: First

    Area: 2490.39 Square Feet

    Dimensions: 53.1x46.9

  • Workshop

    Level: First

    Area: 120.93 Square Feet

    Dimensions: 13.9x8.7

Interior

  • Heating

    Central, Electric

  • Flooring

    Ceramic Tile

  • Sewer

    Septic Tank

  • Exterior Features

    Fire Pit, Lighting, Private Mailbox, Rain Gutters, Sidewalk, Storage

  • Cooling

    Central Air

  • Window Features

    Double Pane Windows

  • Appliances

    Bar Fridge, Built In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Ice Maker, Kitchen Reverse Osmosis System, Microwave, Range Hood, Refrigerator, Washer, Wine Refrigerator

  • Interior Features

    Built In Features, Ceiling Fans(s), Dry Bar, High Ceilings, Kitchen/family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Vaulted Ceiling(s), Walk In Closet(s), Wet Bar, Window Treatments

Construction

  • Year Built

    Year Built: 1988

  • Home type

    Single Family Residence

  • Foundation Details

    Slab

  • Architectural Style

    Traditional

  • Construction Materials

    Block, Stucco

  • Roof

    Shingle

  • Property Condition

    Completed

Utilities & Energy

  • Association Amenities

    Basketball Court, Cable Tv, Gated, Pickleball Court(s), Tennis Court(s)

  • Pool Features

    Gunite, Heated, In Ground, Outside Bath Access, Salt Water, Screen Enclosure

  • Utilities

    Bb/hs Internet Available, Cable Available, Electricity Connected

  • Laundry Features

    Inside, Laundry Room

  • Parking Features

    Driveway, Garage Door Opener, Garage Faces Side, Ground Level, Oversized, Workshop In Garage

  • Security Features

    Gated Community

  • Water Source

    Private, Well

  • Fireplace Features

    Decorative, Electric, Family Room

Other Features

  • Vegetation

    Fruit Trees, Mature Landscaping, Oak Trees, Trees/landscaped

  • Subdivision Name

    Deer Island

  • Patio And Porch Features

    Covered, Front Porch, Patio, Screened

  • Lot Features

    Landscaped, Level, Oversized Lot, Sidewalk, Paved, Private, Unincorporated

  • Community Features

    Deed Restrictions, Gated Community No Guard, Golf Carts Ok, Sidewalks, Tennis Court(s), Street Lights

Price History

DateEventPrice

09/17/2026

Source: mls_logoStellar MLS-FL #MFRO6440044

Contingent (Active Under Contract)

$1,495,000

$547/sqft

09/14/2026

Source: mls_logoStellar MLS-FL #MFRO6440044

Listed for Sale

$1,495,000 +193.14%

$547/sqft

12/21/2017

Source: mls_logoStellar MLS-FL #MFRO5519770

Price Decreased

$510,000 -1.73%

$186/sqft

09/18/2017

Source: mls_logoStellar MLS-FL #MFRO5519770

Sold

$519,000 -8.14%

$190/sqft

05/17/2017

Source: mls_logoStellar MLS-FL #MFRO5435255

Listing Removed

$564,999 -13.08%

$207/sqft

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Based on information from Stellar MLS® through Oct 22, 2026, 03:45PM as submitted to and distributed by MLS GRID. All data is obtained from various sources and may not have been verified by the broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end-user license agreement prescribed by the Member Participant’s applicable MLS, if any, and as amended from time to time. © 2026 Stellar MLS. All Rights Reserved.

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