Orlando/Conway / Belle Isle Homes with Two Story Style

Orlando/Conway / Belle Isle Homes with Two Story Style

Welcome to the vibrant region of Orlando, specifically the charming neighborhoods of Conway and Belle Isle in Orange County, FL. Known for their picturesque surroundings and close-knit communities, these areas offer the perfect blend of suburban tranquility and urban convenience.

If you're in the market for a home with a two-story style, you're in luck! Conway and Belle Isle boast a variety of properties that cater to this preference. From traditional colonial-inspired designs to modern and sleek architecture, there's a two-story home to suit every taste.

Imagine waking up to the Florida sunshine streaming through the windows of your spacious second-floor bedroom, or enjoying a relaxing evening on the balcony overlooking your lush backyard. With a two-story home in Conway or Belle Isle, the possibilities are endless.

Whether you're drawn to the excellent schools, proximity to Orlando's world-class attractions, or simply the laid-back Florida lifestyle, Conway and Belle Isle have something for everyone. Don't miss the opportunity to make your dream of owning a two-story home in this desirable region a reality. Let us help you find the perfect property to call home in Conway or Belle Isle.

Newest Orlando/Conway / Belle Isle Homes with Two Story Style

$385,000
3 Beds ⋅ 3 Baths ⋅ O6429246 MLS
Welcome to this charming 3-bedroom, 2.5-bath half duplex nestled in the desirable Essex Pointe community of Bryn Mawr. Offering a functional two-story layout, all three bedrooms and two full bathrooms are located upstairs, while the main living areas and convenient half bath are downstairs, perfect for both everyday living and entertaining. Inside, you’ll appreciate the soaring vaulted ceilings that create an open, airy feel, along with numerous updates completed in 2026, including fresh interior paint, new carpet throughout the upstairs, and partial bathroom renovations, making this home move-in ready with peace of mind. In 2022 the kitchen and primary bathroom were remodeled. Main components of the home: 2026 ROOF, 2026 RE-PLUMBING, 2022 AC SYSTEM. Situated on an oversized .25 acre lot, the backyard offers endless potential to create your own private outdoor retreat. Mature landscaping provides shade, character, and a beautiful backdrop for gardening, entertaining, or designing the backyard oasis you’ve always envisioned. Ideally located in the established Bryn Mawr community, residents enjoy a convenient location with easy access to Downtown Orlando, Orlando International Airport, major highways, shopping, dining, and everyday conveniences.

5305 Denver Drive, Orlando
$340,000
3 Beds ⋅ 3 Baths ⋅ O6430487 MLS ⋅ 1 BLDG.
Virtually Staged. Don’t miss this opportunity to own the builder’s model home complete with all of the upgrades in this stunning, gated community! As you enter you are welcomed by a bright and open floor plan with vaulted ceilings and wood flooring throughout the first floor. The kitchen comes complete with granite countertops, breakfast bar/island and huge pantry. The Owner’s Suite has tray ceilings, a walk-in closet and a spacious bathroom with dual vanities. Enjoy your back patio with composite deck with planter boxes built in overlooking a large green space. Schedule your private showing today!

3811 Brighton Park Circle, Orlando
$439,900
3 Beds ⋅ 3 Baths ⋅ O6429454 MLS
Discover Contemporary Comfort in This Spacious 3-Bedroom, 2.5-Bath Home This beautiful two-story contemporary home offers the perfect blend of modern updates, warm architectural character, and effortless living on a low-maintenance lot. From the moment you step inside, you are greeted by dramatic vaulted ceilings, abundant natural light, and a bright, open floor plan that feels both inviting and elegant. At the heart of the home lies the newly renovated kitchen, featuring designer tile, solid wood cabinetry, granite countertops, and a center island that serves as the ideal gathering spot. It flows seamlessly into the combined living and dining area, where a beautiful fireplace adds ambiance and charm—perfect for cozy nights or gatherings with friends and family. The first-floor primary suite offers tranquility and privacy, featuring a fully updated bathroom with dual sinks, a sleek new shower, and a walk-in closet with custom organizers. Upstairs, three spacious secondary bedrooms provide versatility for guests, family, a home office, or a creative space. The second-floor full bathroom also impresses, boasting dual sinks, ample storage, and a classic tub/shower combination. Additional features include: Indoor laundry room Spacious 2-car garage Quality wood-frame construction Bright, airy interiors throughout Low-maintenance yard ideal for easy living Fully fenced backyard with durable vinyl fencing The community truly elevates the experience. Known for its friendly, close-knit atmosphere, this is a neighborhood where people genuinely look out for one another. The well-managed homeowners association takes pride in keeping the area impeccably maintained. Residents enjoy a resort-style community pool, a welcoming clubhouse, and well-kept tennis courts, offering endless opportunities for recreation and relaxation. During the holidays, the entire neighborhood transforms—festive lights, joyful gatherings, and a warm sense of community make it one of the most special places to live. Move-in ready, beautifully updated, and located in a community that feels like home from the very first moment—this contemporary gem has it all.

2640 Waymeyer Drive, Orlando
$675,000
5 Beds ⋅ 4 Baths ⋅ O6429514 MLS
Welcome to this stunning 5-bedroom, 4-bathroom pool home offering over 3,100 square feet of beautifully designed living space in the exclusive, gated community of The Landing at Lake George. With just 34 homes in the neighborhood, this rare opportunity combines privacy, elegance, and an unbeatable location. From the moment you arrive, you'll be impressed by the stately curb appeal and oversized 3-car garage. Step inside to a dramatic two-story foyer filled with natural light, soaring volume ceilings, crown molding, and an open, inviting floor plan. Just off the entry is a versatile bonus room with a beautiful bay window—perfect as a home office, formal living room, or playroom. Designed for both everyday living and entertaining, the spacious kitchen features granite countertops, stainless steel appliances, a center island, breakfast bar, and sunny breakfast nook. The kitchen flows seamlessly into the dining area and expansive family room, where sliding glass doors open to your private backyard oasis. Enjoy Florida living at its finest with a screened porch overlooking the heated saltwater pool and spa, all surrounded by a fully fenced backyard—ideal for relaxing, entertaining, or spending time with family and friends. The first-floor primary suite is a peaceful retreat, complete with dual walk-in closets and a spacious en-suite bathroom. An additional first-floor bedroom and full bathroom provide the perfect setup for guests or multi-generational living. A large laundry room with a utility sink adds everyday convenience. Upstairs, you'll find a generous loft that offers flexible living space for a media room, game room, or second family room, along with three additional bedrooms and two full bathrooms. Every bedroom features large closets, providing exceptional storage throughout the home. Additional highlights include a new roof (2023), heated saltwater pool and spa, security system, irrigation system, sewer, Terminix termite bond, and ultra-fast 5 Gig fiber optic internet. This exceptional home offers the perfect combination of space, comfort, and modern amenities. Conveniently located just minutes from Orlando International Airport, Downtown Orlando, Lake Nona Medical City, major highways, shopping, dining, and top-rated schools, you'll enjoy easy access to everything Central Florida has to offer.

3342 Herringridge Drive, Orlando
$535,000
4 Beds ⋅ 3 Baths ⋅ O6429377 MLS
Welcome to your own waterfront retreat in a beautiful gated community in the heart of Orlando! Nestled on a stunning lakefront lot, this exceptional 4-bedroom, 2.5-bath home with a versatile flex room offers the perfect blend of luxury, comfort, and convenience. BRAND NEW Vinyl Plank flooring throughout living room, kitchen and master bedroom. New Dishwasher just installed. Wake up to breathtaking water views and experience the tranquility of lakefront living—all while being just minutes from the Conway Chain of Lakes, Orlando International Airport, Downtown Orlando, major highways, shopping, dining, and entertainment. Designed with both functionality and elegance, this spacious home features a highly desirable first-floor primary suite, providing privacy and convenience. The expansive primary retreat includes separate his-and-her walk-in closets and an en-suite bathroom, creating the perfect space to unwind. The thoughtfully designed floor plan offers generous living areas filled with natural light and a flexible bonus room that can easily serve as a home office, media room, playroom, or fitness space. The seamless indoor-outdoor flow makes entertaining effortless while showcasing the spectacular lake views. Whether you’re enjoying your morning coffee overlooking the water, hosting family and friends, or simply appreciating the security and exclusivity of a gated community, this home delivers an exceptional Florida lifestyle in one of Orlando’s most convenient locations. Don’t miss this rare opportunity to own a beautiful lakefront home that perfectly combines privacy, elegance, and accessibility. Schedule your private showing today!

3701 Seminole Drive, Orlando
$550,000
4 Beds ⋅ 3 Baths ⋅ O6427391 MLS
Welcome to 4723 Conway Road! This beautifully upgraded home has 4 bedrooms, 2.5 baths plus an office. Locate on an oversized lot with plenty of room to relax, entertain and truly enjoy everything the lifestyle has to offer. Built in 2020, this home is loaded with upgrades: gorgeous ceramic tile throughout the first floor, granite countertops, window treatments and stylish light fixtures accent the open floor plan. The kitchen has a focal point island with contrasting color cabinets, soft close drawers and doors, stainless steel appliances (including a brand-new fridge) and a large walk-in pantry. The spacious primary bedroom has 2 walk-in closets and ensuite bathroom featuring dual sinks, and a sleek frameless glass shower for a spa-like feel. Outside, you'll find a fenced front yard with black fencing and a privacy hedge, gutters with leaf guard installed, and an expansive rear yard complete with privacy fencing, a patio that features a wall-mounted television including a Storm Shell cover, and a cozy fire pit area — perfect for quiet evenings or get-togethers. Additional peace of mind comes with a new AC unit (installed December 2025, 10-year warranty), complete irrigation system and perimeter termite protection with an active termite bond. A security system and attached 2-car garage provides extra convenience and safety. Best of all, there's NO HOA, and you're conveniently located near restaurants and shopping, with easy access to the airport and major highways.

4723 Conway Road, Orlando
$699,900
5 Beds ⋅ 3 Baths ⋅ O6425858 MLS
Welcome to one of Conway's most distinctive renovated homes, where timeless design, modern comfort, and exceptional versatility come together on an oversized cul-de-sac lot in one of Orlando's most desirable neighborhoods. Offering five bedrooms, three full bathrooms, over 2,200 square feet of beautifully updated living space, and a detached guest house, this home delivers a rare combination of style, flexibility, and functionality. From the moment you arrive, the charming Craftsman-inspired exterior, mature oak tree, and inviting curb appeal set the tone. Inside, a bright open-concept floor plan welcomes you with luxury vinyl plank flooring, abundant natural light, and seamless spaces designed for both everyday living and effortless entertaining. The heart of the home is the beautifully appointed kitchen, featuring shaker-style soft-close cabinetry, quartz countertops, stainless steel appliances, a custom range hood, and an oversized peninsula with seating that naturally becomes the gathering place for family and friends. The spacious first-floor primary suite offers a private retreat with a beautifully renovated spa-inspired bath featuring dual vanities and modern finishes. Upstairs, additional bedrooms—including two connected by a Jack-and-Jill bathroom—provide flexibility for family, guests, home offices, or hobbies. 2 separate AC units. Upstairs unit is roughly 5 years old, downstairs is 2024 (high efficiency). 2023 roof and 2024 water heater. Beyond the stunning renovation, the current owners have continued investing in the home with thoughtful improvements that enhance comfort and efficiency, including new blown-in attic insulation for improved year-round energy performance. Step outside and discover the backyard that truly sets this home apart. The expansive screened lanai overlooks a sparkling saltwater pool and spa, creating the perfect setting for relaxing, entertaining, or enjoying Florida living year-round. The oversized, fully fenced backyard provides exceptional privacy and space that's increasingly difficult to find. The detached 429-square-foot guest house with mini split offers endless possibilities. Whether you're looking for a private home office, fitness studio, creative space, guest suite, or multi-generational living, this flexible space adapts to your lifestyle and even offers future rental potential where permitted. Additional features include a water filtration system, irrigation system, washer and dryer, a two-car garage, no HOA, and the peace of mind of being located in Flood Zone X. Ideally located in the heart of Conway, you'll enjoy quick access to Downtown Orlando, SoDo, the Hourglass District, Orlando International Airport, Lake Conway, shopping, dining, parks, and major commuter routes while enjoying the charm of one of Orlando's most established communities. Beautifully renovated, thoughtfully upgraded, and meticulously maintained, this is more than a home—it's a lifestyle. Opportunities to own a property with this combination of flexible living space, resort-style outdoor amenities, and an unbeatable Conway location are rare. Schedule your private showing today and experience everything this home has to offer.

3237 Kew Gardens Lane, Orlando
$650,000
3 Beds ⋅ 3 Baths ⋅ O6424727 MLS
Welcome to this distinctive New Orleans-inspired home in Greenview at Dover, set on a generous quarter-acre corner lot shaded by mature oak trees and enhanced by a brick driveway, wraparound brick walkway, front awning, and side-entry two-car garage. Offering 3 bedrooms, 2.5 baths, a dedicated office, and approximately 2,232 square feet, the home blends memorable architectural details with comfortable spaces designed for everyday living, working from home, and entertaining. Wood flooring throughout means there is no carpet, while interior shutters, double-hung vinyl windows, fresh paint, and abundant natural light create a warm and polished atmosphere. The private office provides a quiet place for remote work, reading, or hobbies without taking away from the home’s main living areas. The recently renovated kitchen is a true centerpiece with granite countertops, stainless steel appliances, a breakfast bar, handcrafted copper range hood, copper farmhouse sink, and coordinating tile backsplash. It opens naturally to the family room, where a gas fireplace creates an inviting gathering space for quiet evenings or time with guests. Three sets of French doors extend the living areas outdoors, allowing gatherings to flow easily between the interior and patio. The primary suite offers an additional gas fireplace and a comfortable private retreat, while attic storage and a well-equipped laundry room with cabinetry add practical space for everyday organization. Outdoor living is one of the home’s defining features. A spacious brick patio spans the rear of the residence beneath a tongue-and-groove wood ceiling, creating a welcoming setting for morning coffee, outdoor dining, weekend gatherings, or relaxing at the end of the day. A retractable awning provides added shade and shelter, while the fenced backyard features a decorative brick fountain, exterior lighting, and a greenhouse equipped with water and electricity. Whether used for growing herbs and flowers, tending a plant collection, pursuing hobbies, or creating a peaceful retreat, the backyard offers multiple ways to enjoy the Florida lifestyle. A seven-zone irrigation system supplied by private wells helps support the landscaping, and the wraparound brick walkway provides convenient access around the home. Additional features include a 2022 roof, solar-energy system, whole-house generator with automatic transfer switch, EV charging station, central vacuum, whole-house water softener, upgraded electrical panel, hybrid heat-pump water heater, and two heat-pump HVAC systems. The garage is equipped with its own mini-split system, creating a more comfortable environment for parking, projects, storage, exercise, or workshop use. Conveniently located near shopping, dining, parks, major roadways, downtown Orlando, and Orlando International Airport, this home offers a rare combination of distinctive character, thoughtful upgrades, flexible living spaces, and an enjoyable Central Florida lifestyle.

900 Lenmore Court, Orlando
$399,000
3 Beds ⋅ 3 Baths ⋅ O6421227 MLS
3-bedroom, 2.5-bath home in the Wedgewood Groves community with a new roof installed in 2022. Features include separate living and dining rooms with plantation shutters, a kitchen with a dinette area, indoor laundry, and a 2-car garage. All bedrooms are located upstairs. Enjoy a screened patio overlooking the fenced backyard. Community amenities include a pool and tennis courts. Conveniently located near Downtown Orlando, Orlando International Airport, shopping, dining, and major highways.

3837 Holston Way, Orlando
$160,000
1 Beds ⋅ 1 Baths ⋅ O6422228 MLS ⋅ 5468 BLDG.
Move-in ready and full of potential, this 1-bedroom, 1-bathroom condo in the Siesta Lago gated community offers a low-maintenance lifestyle just minutes from Downtown Orlando. This two-story unit features neutral finishes, laminate and ceramic tile flooring, and a walk-in closet in the spacious bedroom. Built in 1990, it offers a clean, functional layout ideal for a first-time buyer, downsizer, or investor. The community is packed with resort-style amenities including a pool, clubhouse, tennis courts, dog park, playground, and a fitness center. Assigned parking is included. Conveniently located just a short drive from shopping, restaurants, Orlando International Airport, and everything the city has to offer. This Orlando condo is your key to comfort, convenience, and value in one of the area’s most accessible neighborhoods.

5468 E Michigan Street Unit 5468-4, Orlando
$2,285,000
5 Beds ⋅ 3 Baths ⋅ O6418107 MLS
Welcome to your contemporary Mediterranean waterfront estate on the prestigious Lake Conway Chain of Lakes, where timeless architectural elegance meets sophisticated modern design. This stunning 5-bedroom, 3-bathroom estate offers 3,625 feet of thoughtfully designed living space. The moment you walk through the front door, you'll notice the beautiful white oak hardwood flooring that flows throughout the entire home. Completely remodeled inside and out, this exceptional residence has been reimagined from top to bottom with extensive high-end upgrades, thoughtful design, and an ideal split floor plan. Designed for both everyday living and entertaining, the main living areas are filled with natural light, while the chef-inspired kitchen and breathtaking Lake Conway views serve as the home's focal points. The kitchen features solid wood soft-close cabinetry, quartz countertops, a large custom island, and high-end appliances with manufacturer warranties. All new front windows and sliding glass doors, custom mahogany front doors, designer lighting and fans, and select smart lighting features further enhance the home. The spacious primary suite offers lake views, direct access to the pool area, and a luxurious spa-inspired bathroom featuring custom vanities, frameless glass showers, and a high-end soaking tub. On the opposite side of the home, you'll find three additional bedrooms and two beautifully updated bathrooms, including a convenient pool bath with direct access to the outdoor living area. An additional flex room provides endless possibilities and can easily serve as a fifth bedroom, private office, gym, or hobby room. Upstairs, the bonus loft opens to a private balcony overlooking the lake, offering the perfect place to enjoy your morning coffee or unwind while taking in the incredible water views. Outdoor living is equally impressive, featuring a resurfaced pool patio, cedar-covered lanai, custom outdoor built-in grill, updated lighting, and a beautifully maintained beach area overlooking the lake. A newly installed dock in 2025, complete with a covered boat lift, provides direct access to the Lake Conway Chain for boating, skiing, fishing, and making memories on the water. Conveniently located near Downtown Orlando, Orlando International Airport, world-famous theme parks, premier dining, and entertainment, this exceptional property offers the perfect blend of luxury, location, and waterfront living. Schedule your private tour today and experience everything this extraordinary Lake Conway waterfront estate has to offer.

2501 Trentwood Boulevard, Orlando
$369,900
2 Beds ⋅ 2 Baths ⋅ O6421233 MLS
Fully Remodeled 2 Bed 1.5 Bath Lakefront half duplex with multiple balconies and large private backyard. Everything is Brand New and Fully Upgraded inside and out including the Kitchen with Quartz Countertops and Shaker Cabinets, Brand New Stainless Steal Appliances, New Doors, New Sliding Glass Doors, New Fixtures throughout, New Water Heater, New Roof, New A/C, Fresh Interior/Exterior Paint, Premium Commercial-Grade LVP Flooring, New Showers and Cabinetry including New Quartz in Bathrooms, Front loader washer/dryer, new hardware throughout, new baseboards and much more. This lakefront property has NO HOA and is centrally located in the Conway Area close to dining, shopping, and top-rated schools.

3058 Graceland Court, Orlando
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