EasyStreet

Call to Schedule a Showing

(407) 718-3706

(407) 718-3706

5127 Leeward Way, Orlando, FL 32809

$1,650,000

Charming brick home with mature landscaping, manicured lawn, and a welcoming brick pathway at 5127 Leeward Way, Orlando, FL 32809
  • Bedrooms

    4

  • Baths

    3

  • Sq. Feet

    3836

  • Year Built

    1972

  • Days On Market

    20

  • $/SqFt

    $430

100 Photos

  • Charming brick home with mature landscaping, manicured lawn, and a welcoming brick pathway at 5127 Leeward Way, Orlando, FL 32809
  • Inviting front porch with brick accents, decorative sconces, and a stylish double door entry at 5127 Leeward Way, Orlando, FL 32809
  • Elegant foyer featuring decorative tile, chandelier, and an archway to the dining area at 5127 Leeward Way, Orlando, FL 32809
  • Bright living room with hardwood floors and sliding glass doors leading to an outdoor pool at 5127 Leeward Way, Orlando, FL 32809
  • Open living room with hardwood floors, recessed lighting, and views of the backyard pool at 5127 Leeward Way, Orlando, FL 32809
  • Cozy living room features hardwood flooring, recessed lights, and bright backyard view at 5127 Leeward Way, Orlando, FL 32809
  • Spacious living area showcasing hardwood floors, natural light, and an open layout to the kitchen at 5127 Leeward Way, Orlando, FL 32809
  • Bright, open space that seamlessly blends the kitchen bar area and living room at 5127 Leeward Way, Orlando, FL 32809
  • Spacious kitchen featuring an island with bar seating, granite countertops, and stainless steel appliances at 5127 Leeward Way, Orlando, FL 32809
  • Luxury kitchen with large island, custom cabinets, granite counters, and stainless steel appliances at 5127 Leeward Way, Orlando, FL 32809
  • Spacious kitchen island with granite counters and seating, perfect for entertaining and casual dining at 5127 Leeward Way, Orlando, FL 32809
  • Modern kitchen with wood cabinets, granite countertops, stainless steel appliances, and an island at 5127 Leeward Way, Orlando, FL 32809
  • Open-concept kitchen boasts an island with granite counters, and stainless steel appliances, connecting to the living room at 5127 Leeward Way, Orlando, FL 32809
  • Bright open kitchen with island, granite countertops, stainless appliances, and ample cabinet storage at 5127 Leeward Way, Orlando, FL 32809
  • Well-organized pantry with ample shelving and counter space for storage and food preparation at 5127 Leeward Way, Orlando, FL 32809
  • Elegant dining room with hardwood floors, decorative lighting, and ample natural light from the window at 5127 Leeward Way, Orlando, FL 32809
  • Open-concept dining room with hardwood floors, decorative lighting, and seamless flow to the kitchen at 5127 Leeward Way, Orlando, FL 32809
  • Living room with hardwood floors, elegant furniture, and an arched doorway at 5127 Leeward Way, Orlando, FL 32809
  • Cozy bedroom with hardwood floors, and plenty of closet space at 5127 Leeward Way, Orlando, FL 32809
  • Cozy dining room with hardwood floors, elegant furniture, and a large mirror at 5127 Leeward Way, Orlando, FL 32809
  • Spacious living room featuring hardwood floors and natural lighting from the large windows at 5127 Leeward Way, Orlando, FL 32809
More Photos \/
  • Gym featuring hardwood floors, weights, lighting, and white bi-fold closet doors at 5127 Leeward Way, Orlando, FL 32809
  • Gym featuring hardwood floors, weights, lighting, and a window at 5127 Leeward Way, Orlando, FL 32809
  • Bedroom featuring hardwood floors, a bed, lighting, bi-fold closet doors, and a window at 5127 Leeward Way, Orlando, FL 32809
  • Bathroom featuring a toilet, sink, and mirror at 5127 Leeward Way, Orlando, FL 32809
  • Spacious bedroom with hardwood floors, tray ceiling, and french doors to the outdoors at 5127 Leeward Way, Orlando, FL 32809
  • Spacious main bedroom featuring hardwood floors, a ceiling fan, french doors and mirrors at 5127 Leeward Way, Orlando, FL 32809
  • Spacious main bedroom featuring hardwood floors, a ceiling fan, doors, and mirrors at 5127 Leeward Way, Orlando, FL 32809
  • Large walk-in closet with custom wood shelving and hardwood floors at 5127 Leeward Way, Orlando, FL 32809
  • Luxurious bathroom featuring double vanities, a soaking tub, and neutral tile at 5127 Leeward Way, Orlando, FL 32809
  • Bright bathroom featuring a soaking tub, large vanity, and a framed mirror at 5127 Leeward Way, Orlando, FL 32809
  • Bright bathroom featuring a soaking tub, vanity and decorative tile work at 5127 Leeward Way, Orlando, FL 32809
  • Bright bathroom with tile floor, soaking tub, vanity, and decorative wall art at 5127 Leeward Way, Orlando, FL 32809
  • Bright bathroom featuring soaking tub, vanity, and walk-in shower at 5127 Leeward Way, Orlando, FL 32809
  • Spacious tile shower with multiple shower heads and controls at 5127 Leeward Way, Orlando, FL 32809
  • Inviting living room with hardwood floors, connecting to outdoor pool area at 5127 Leeward Way, Orlando, FL 32809
  • Spacious living room with hardwood floors and view of the screened pool at 5127 Leeward Way, Orlando, FL 32809
  • Hardwood floors in living room with large sliding doors overlooking a screened pool at 5127 Leeward Way, Orlando, FL 32809
  • Bright living room with hardwood floors and view of the screened pool at 5127 Leeward Way, Orlando, FL 32809
  • Office space with hardwood floors, desk, and view to the bedroom at 5127 Leeward Way, Orlando, FL 32809
  • Charming bedroom featuring a comfortable bed, hardwood floors, and plenty of natural light at 5127 Leeward Way, Orlando, FL 32809
  • Cozy bedroom featuring hardwood floors, a comfortable bed, closet, and bright natural light at 5127 Leeward Way, Orlando, FL 32809
  • Comfortable bedroom featuring hardwood floors, a day bed, and bright natural light at 5127 Leeward Way, Orlando, FL 32809
  • Bright foyer featuring tile flooring, a decorative light fixture and view down a hardwood hall at 5127 Leeward Way, Orlando, FL 32809
  • Comfortable bedroom featuring hardwood floors, a day bed, closet and ensuite bathroom at 5127 Leeward Way, Orlando, FL 32809
  • Accessible bathroom featuring a tile walk-in shower, grab bars, and storage at 5127 Leeward Way, Orlando, FL 32809
  • Accessible bathroom featuring a tile walk-in shower, grab bars, sink and overhead lighting at 5127 Leeward Way, Orlando, FL 32809
  • Well-organized laundry room with white cabinets, countertops, sink, and modern washer and dryer at 5127 Leeward Way, Orlando, FL 32809
  • Spacious outdoor kitchen featuring stainless steel appliances, ample counter space, and a ceiling fan at 5127 Leeward Way, Orlando, FL 32809
  • Outdoor kitchen featuring stainless steel appliances, ample counter space and a double-door entrance at 5127 Leeward Way, Orlando, FL 32809
  • An outdoor kitchen boasts stainless steel appliances, an island, and access to the pool area for convenient entertaining at 5127 Leeward Way, Orlando, FL 32809
  • An indoor kitchen features a stainless steel island, access to the pool area, and a sleek and modern design at 5127 Leeward Way, Orlando, FL 32809
  • The stainless steel kitchen boasts a commercial-grade stove, prep area, and ample counter space for culinary enthusiasts at 5127 Leeward Way, Orlando, FL 32809
  • The outdoor kitchen offers stainless steel appliances, ample counter space, and easy access to the outdoor pool area at 5127 Leeward Way, Orlando, FL 32809
  • Outdoor kitchen featuring a stainless steel range, island prep space, and a convenient pass-through to the dining area at 5127 Leeward Way, Orlando, FL 32809
  • Enjoy the view of the screened pool area, perfect for relaxation and entertainment from the comfort of the house at 5127 Leeward Way, Orlando, FL 32809
  • A screened-in pool area offers ample space for swimming, lounging, and outdoor enjoyment with serene backyard views at 5127 Leeward Way, Orlando, FL 32809
  • A screened-in pool and spa is perfect for outdoor enjoyment and relaxation, surrounded by lush landscaping at 5127 Leeward Way, Orlando, FL 32809
  • Outdoor dining near a screened-in pool, offering ample seating and a relaxed atmosphere for entertaining and leisure at 5127 Leeward Way, Orlando, FL 32809
  • A tranquil deck offers ample seating and serene outdoor views, perfect for relaxation and gatherings in a peaceful setting at 5127 Leeward Way, Orlando, FL 32809
  • Expansive wooden deck perfect for outdoor entertaining and relaxation, with an entrance into the home at 5127 Leeward Way, Orlando, FL 32809
  • Wooden deck showcasing outdoor seating and views of the landscaped yard at 5127 Leeward Way, Orlando, FL 32809
  • Backyard patio area with outdoor seating, lush greenery, and charming pergola at 5127 Leeward Way, Orlando, FL 32809
  • Landscaped backyard featuring a charming patio and lush greenery, perfect for relaxation at 5127 Leeward Way, Orlando, FL 32809
  • Large magnolia tree adding natural beauty to the lush lawn and landscape at 5127 Leeward Way, Orlando, FL 32809
  • Path and pergola entwined with vines and greenery, creating a serene backyard escape at 5127 Leeward Way, Orlando, FL 32809
  • Outdoor patio with pergola, lush landscaping, and comfortable seating for entertaining at 5127 Leeward Way, Orlando, FL 32809
  • Backyard featuring a patio area, wrought iron table and chairs, landscaping, and charming pergola at 5127 Leeward Way, Orlando, FL 32809
  • Cozy backyard patio with a vine-covered pergola, perfect for outdoor lounging and entertaining at 5127 Leeward Way, Orlando, FL 32809
  • Secluded backyard patio with lush greenery and comfortable seating, ideal for outdoor relaxation at 5127 Leeward Way, Orlando, FL 32809
  • Inviting backyard patio with screened-in porch, mature trees, and charming outdoor seating area at 5127 Leeward Way, Orlando, FL 32809
  • Beautiful backyard patio with mature trees, outdoor seating area, and lush landscaping at 5127 Leeward Way, Orlando, FL 32809
  • Spacious covered patio with brick flooring, string lights, and a built-in outdoor kitchen setup at 5127 Leeward Way, Orlando, FL 32809
  • Expansive covered patio features brick flooring, outdoor lighting, and a convenient grilling area at 5127 Leeward Way, Orlando, FL 32809
  • Exterior view features a brick entryway, double doors, and well-maintained landscaping at 5127 Leeward Way, Orlando, FL 32809
  • The home's two-car garage is complemented by an outdoor patio and lovely greenery at 5127 Leeward Way, Orlando, FL 32809
  • A beautiful yard is home to a wonderful Magnolia tree with a charming swing underneath at 5127 Leeward Way, Orlando, FL 32809
  • Shady backyard featuring a charming Magnolia tree with swing, a well-kept lawn and home with a patio at 5127 Leeward Way, Orlando, FL 32809
  • Picturesque boat dock with boat lift, patio furniture, and canopy offering sun protection at 5127 Leeward Way, Orlando, FL 32809
  • Backyard showing a boat dock, lovely lawn, patio furniture covered by a red shade at 5127 Leeward Way, Orlando, FL 32809
  • Upstairs exterior view of home with wooden deck and plenty of outdoor seating at 5127 Leeward Way, Orlando, FL 32809
  • Spacious upstairs living room with rich wood floors and lots of natural light at 5127 Leeward Way, Orlando, FL 32809
  • Bright living room with hardwood floors, neutral paint, and a door to the outdoor deck at 5127 Leeward Way, Orlando, FL 32809
  • Large room with hardwood floors, pool table, pinball machine, and bar-height dining table at 5127 Leeward Way, Orlando, FL 32809
  • Enjoy a spacious deck with outdoor seating perfect for entertaining guests at 5127 Leeward Way, Orlando, FL 32809
  • Lovely upstairs deck with outdoor seating offering stunning views of the surrounding landscape at 5127 Leeward Way, Orlando, FL 32809
  • Aerial view of the house showcasing the upstairs deck and beautiful landscaping at 5127 Leeward Way, Orlando, FL 32809
  • Aerial view of private dock with multiple boat houses and direct lake access at 5127 Leeward Way, Orlando, FL 32809
  • Picture of lakefront dock with boat lifts, covered seating area, and an American flag at 5127 Leeward Way, Orlando, FL 32809
  • Lakefront dock with boat lifts and outdoor seating on a charming waterway at 5127 Leeward Way, Orlando, FL 32809
  • Breathtaking waterfront view with dock, boat lift, and beautiful natural surroundings, perfect for lake living at 5127 Leeward Way, Orlando, FL 32809
  • Stunning aerial view of luxury homes with pools, lush landscaping, and waterfront access, showcasing upscale living at 5127 Leeward Way, Orlando, FL 32809
  • Breathtaking aerial shot of luxurious waterfront homes, revealing impressive pools and meticulously kept landscaping at 5127 Leeward Way, Orlando, FL 32809
  • Expansive aerial view showcases exquisite waterfront homes, with lush landscaping and prime lakeside location at 5127 Leeward Way, Orlando, FL 32809
  • Majestic aerial view captures stunning lakeside properties with private docks, swimming pools, and lush green surroundings at 5127 Leeward Way, Orlando, FL 32809
  • Captivating aerial view of premier lakeside homes, highlighting their private docks, pools, and picturesque landscaping at 5127 Leeward Way, Orlando, FL 32809
  • Detailed floor plan showcasing the layout of this spacious home, including main house, garage, and guest house at 5127 Leeward Way, Orlando, FL 32809
  • Detailed floor plan showcasing the layout of this spacious home's main house at 5127 Leeward Way, Orlando, FL 32809
  • Floor plan showing the spacious layout of the home's garage at 5127 Leeward Way, Orlando, FL 32809
  • Floor plan showing the layout of the spacious detached guest house at 5127 Leeward Way, Orlando, FL 32809
Less Photos /\

Tour This Home

Thu
5 Jun
Fri
6 Jun
Sat
7 Jun
Sun
8 Jun
Mon
9 Jun
Tue
10 Jun
Wed
11 Jun

Home Description

This home is a private oasis WATERFRONT with a Direct Access to the Conway Chain of lakes right in your own back yard. Every corner invites you to unwind, gather, and create unforgettable moments. Spend your days lounging by the fully screened pool and spa, dining al fresco in the gourmet outdoor kitchen, or enjoying a sunset cruise from the shaded dock and Covered Lift. The lush backyard is a sanctuary featuring a meditation garden, vibrant tropical landscaping, and an abundant garden path offering fresh carambola and avocado. Enjoy the whimsical charm of the air-conditioned she shed/ work room, complete with a chandelier—perfect for painting, sewing, or creative escapes. Challenge friends to a game of hook and ring, or relax under the pergola by the fire pit or on the swing beneath the grand magnolia tree. Inside, the home is equally impressive with a thoughtfully designed layout that blends function and style. The expansive cook’s kitchen is the heart of the home, featuring double ovens, warming drawer, full-size side-by-side refrigerator and freezer, oversized island and separate breakfast bar, icemaker, and space for a coffee station. The kitchen opens to a spacious family room, ideal for casual gatherings, while the formal dining and living rooms provide elegant spaces for entertaining. The large primary suite is an expansive owner’s haven, offering two walk-in closets, a luxurious jetted tub, walk-in shower, and an adjacent office or flexible den space. Three additional bedrooms are located on the opposite side of the home for ultimate privacy, along with two full bathrooms, one with convenient pool access and an accessible shower. Tucked above the detached three-car garage is a spacious bonus game room with a private deck overlooking the beautifully manicured backyard and Lake Gatlin—perfect for entertaining, relaxing, or taking in the serene lake views. Additional features include a 2018 roof, updated HVAC systems (2024), and a prime location on one of Orlando’s most desirable chains of lakes. This is more than a home—it’s a lifestyle of lakefront living, effortless entertaining, and everyday moments made extraordinary. Schedule your private tour today.

  • MLS #: O6309938
  • Address: 5127 Leeward Way
  • Levels: One
  • City: Orlando
  • Zip: 32809
  • County: Orange
  • Subdivision: River Oaks
  • Community Features: Street Lights
  • Private Pool: True
  • Pool Features: Gunite,In Ground,Salt Water,Screen Enclosure
  • Spa Features: In Ground
  • Water View: Canal,Lake - Chain of Lakes
  • Water Name: CONWAY CHAIN OF LAKES
  • Water Frontage: Canal - Freshwater,Canal Front
  • Water Feet: 0
  • Water Extras: Lift,Lift - Covered,Skiing Allowed
  • Water Access: Canal - Freshwater,Lake,Lake - Chain of Lakes
  • Interior Features: Eat-in Kitchen,Living Room/Dining Room Combo,Primary Bedroom Main Floor,Split Bedroom,Stone Counters,Tray Ceiling(s)
  • Appliances: Built-In Oven,Convection Oven,Cooktop,Dishwasher,Disposal,Dryer,Ice Maker,Microwave,Refrigerator,Tankless Water Heater,Washer
  • Floor Covering: Ceramic Tile,Wood
  • Exterior Features: Lighting,Outdoor Grill,Outdoor Kitchen,Private Mailbox,Sliding Doors
  • Exterior Contruction: Block
  • Foundation: Block
  • Front Exposure: West
  • Roof: Shingle
  • Building Sqft: 4941

Available now at $1,650,000

Approximate Room Sizes / Descriptions

Kitchen19x19FirstCeramic Tile
Family Room27x16FirstWood
Dining Room13x14First
Game Room22x36Second
Living Room13x14First
Florida Room14x33First
Bedroom 111x10FirstWood
Bedroom 214x10FirstWood
Bedroom 314x16FirstWood
Primary Bedroom19x22FirstWood
  • Attached Garage: False
  • Garage: True
  • Garage Spaces: 3
  • Garage Feature: Oversized,Parking Pad,Workshop in Garage
  • Carport: False
  • Carport Spaces: 0
  • Air Conditioning: Central Air
  • Heating: Central
  • Utilities: Cable Available,Public
  • Lot Sqft: 26636.00
  • Lot Acres: 0.6100
  • Total Acre: 1/2 to less than 1
  • Lot Num: 43
  • HOA Fees: $175 Annually
  • HOA Monthly Amount: $15
  • HOA/Community Assoc: Required
  • Senior Community: False
  • Style: Single Family Residence
  • Pets Allowed: No
  • : 888-455-6040

Neighborhood

The average asking price of a 4 bedroom Orlando home in this zip code is $582,895 (64.7% less than this home).

This home is priced at $430/sqft, which is 37.3% less than similar homes in the 32809 zip code.

Potential Great Value

Map | Street | Birds Eye

Print Map | Driving Directions

Financial

  • Approx Payment:$8,027*
  • Taxes:$8,717

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at (407) 718-3706 and speak with one of our real estate consultants.

Listing Courtesy of FATHOM REALTY FL LLC. For information or to schedule a viewing of this property (MLS# O6309938), call: 407 718 3706

5127 Leeward Way, Orlando FL is a single family home of 3836 sqft and is currently priced at $1,650,000 . This single family home has 4 bedrooms. A comparable home for sale at 837 Quintilian Ave in Orlando is listed at $350,000. In addition to single family homes, EasyStreet also makes it easy to find Homes, Condos, New Homes and Foreclosures in Orlando, FL. Highlands Lake Conway, Mandalay Shores and Wind Harbor are nearby neighborhoods. MLS O6309938 has been posted on this site since 5/17/2025 (today).

2025 6/5/2025.

Message Agent

Send

Schedule a tour

5127 Leeward Way Orlando FL 32809

Choose a day and time

You Requested

We'll be in touch shortly to confirm your tour time and other details. Please let us know how to reach you.

Schedule Tour

CLOSE

Your message has been sent!

The agent will be in touch with you in just a minute.