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

$590,000
4 Beds ⋅ 4 Baths ⋅ S5155524 MLS
Welcome to your next home! Nestled in the charming Rosedale Cove community in Conway, just minutes south of Downtown Orlando, this modern 4-bedroom, 3.5-bathroom home with a 2-car garage offers the perfect combination of style, space, comfort, and serenity. This beautiful home is packed with upgrades designed to make everyday living a pleasure. The spacious layout features four generously sized bedrooms upstairs, providing plenty of room for family, guests, or a home office. The modern kitchen is beautifully upgraded with high-end cabinetry, a large pantry, and an expansive kitchen island, ideal for cooking, entertaining, and gathering with family and friends. Step outside and enjoy your private, fenced backyard overlooking the pond, complete with a deck and a brand-new BBQ grill with rotisserie burner, creating the perfect setting for outdoor dining, entertaining, or simply relaxing while enjoying the peaceful water view. Situated on a quiet cul-de-sac with no through traffic, this home provides a tranquil retreat while keeping you conveniently close to Downtown Orlando, shopping, dining, entertainment, parks, and major roadways. Offering an exceptional balance of privacy, location, and comfortable living, this Rosedale Cove home is ready for its next owner. Don't miss the opportunity to make it yours schedule your private showing today and experience everything this wonderful home.

2813 Roseglen Way, Orlando
$479,900
3 Beds ⋅ 3 Baths ⋅ O6429216 MLS
Welcome home to this beautifully refreshed 3 or 4-bedroom, 2 and a half bath residence nestled in the sought-after, well-established community of Wood Green. Offering a versatile split-bedroom floor plan, generous indoor and outdoor living spaces, fresh neutral finishes, and a spectacular backyard, this inviting home combines comfort, flexibility, and an incredibly convenient Orlando location. From the moment you arrive, you'll appreciate the home's attractive landscaping and welcoming curb appeal. Recent attention to the property, including fresh paint, professionally cleaned carpeting, and exterior pressure washing, gives the home a crisp, refreshed appearance and provides a wonderful neutral canvas ready for your own personal style. Step inside to discover a light and welcoming interior enhanced by soft, neutral colors designed to complement virtually any décor. The spacious formal living area offers plenty of room for entertaining and flows naturally toward the home's wonderful outdoor living spaces. The flexible floor plan provides three bedrooms plus an additional loft that can easily function as a fourth bedroom, home office, den, playroom, or hobby space. At the heart of the home, the kitchen overlooks the family room, creating an open and comfortable gathering space where everyone can stay connected. Whether you're preparing a casual weeknight dinner, enjoying morning coffee, or entertaining friends and family, this fun layout makes everyday living easy. Florida living truly shines when you step outside to the spacious screened lanai, a wonderful extension of the home's living area. Imagine relaxing with your morning coffee, enjoying dinner outdoors, hosting weekend barbecues, or simply unwinding at the end of the day while enjoying the privacy of your own backyard. Beyond the lanai is an impressively large backyard surrounded by established landscaping, offering plenty of room for outdoor activities, pets, gardening, entertaining, or simply enjoying the Florida sunshine. Adding even more value and versatility is the large backyard storage shed, providing an abundance of space for lawn equipment, bicycles, tools, holiday decorations, hobbies, and all those extras you want conveniently stored yet easily accessible. The desirable split-bedroom design provides added privacy, while the home's spacious living areas offer flexibility for today's changing lifestyles. Fresh paint, neutral tones, cleaned carpeting, pressure-washed exterior areas, mature landscaping, and the generous outdoor spaces help make this property feel refreshed and ready for its next chapter. And when it comes to location, Wood Green delivers outstanding convenience. Tucked within a quiet, established neighborhood yet centrally located, the home offers easy access to major highways and roadways, making travel throughout Central Florida remarkably convenient. Orlando International Airport is just minutes away, while nearby Barber Park provides wonderful opportunities for recreation, sports, walking, outdoor activities, and enjoying the Florida lifestyle. With its 3 or 4-bedroom flexibility, 2 baths, split floor plan, neutral interior, fresh paint, spacious screened lanai, beautiful landscaping, oversized backyard, large storage shed, and convenient location, this Wood Green home offers tremendous versatility and plenty of room to make it your own. Come discover the space, flexibility, and possibilities this wonderful home has to offer!

5157 Formby Drive, Orlando
$379,900
3 Beds ⋅ 3 Baths ⋅ O6431022 MLS
Virtually Staged. Virtually Staged. Welcome home to Essex Point South! Turn into the community and this is the first home you see, sitting proudly across from the tennis court, fully updated and move-in ready. The front door opens to soaring two-story ceilings and a great room filled with natural light, generous enough to live like two rooms in one, with a wood-burning fireplace anchoring the space. Wood-look tile flows across the entire main level. The kitchen opens straight into the living space, with granite counters, stainless appliances, espresso cabinetry with under-cabinet lighting, and a breakfast bar. Sliding doors are steps away, so carrying food out to the patio takes no effort. A formal dining room with a bay window sits just beyond. Upstairs, the oversized primary suite features a vaulted ceiling and a recently renovated bath that is the showpiece of the house, with quartz counters, dual vanities, matte black fixtures, and marble-look polished porcelain running from the floor through the shower surround, finished with natural black basalt stone underfoot and a rainfall head overhead. Two more bedrooms share a full bath with granite counters, and all three bedrooms are upstairs together, away from the main living areas. Freshly painted inside and out, with new landscaping. Washer and dryer stay. The oversized two-car garage has room for two vehicles plus small garage storage. The backyard is fully fenced, with a paver patio. Essex Point South offers a community pool, tennis court, and a covered picnic pavilion with brick barbecue grills, on quiet oak-lined streets with sidewalks throughout. Conway puts you close to everything without living on top of it. SR 408 and SR 528 are minutes away, Orlando International Airport is about 10 minutes, and Downtown Orlando is 15. Zoned for Lake George Elementary, Conway Middle, and Boone High. Within 45 minutes you have all the attractions Orlando has to offer, and the Atlantic beaches are just over an hour away. Home Sweet Home awaits!

3109 Bridgeford Drive, Orlando
$235,000
2 Beds ⋅ 2 Baths ⋅ TB8537728 MLS ⋅ Na BLDG.
This 2 bedroom 2 bath ground floor unit at Coach Homes at Dover Village includes a private garage and is nearby the community pool and club house. Included amenities include tennis courts, maintenance of the common areas, building exteriors, garbage collection, water, sewer, cable, and internet. This unit has a newer AC (3 years old) and has ample storage with a linen closet, walk in master closet and laundry room. Washer and dryer is included. The HOA recently installed new roofs and re-piped the condos. Located minutes away from downtown, with easy access to the 408 and the Orlando International Airport.

5336 White Cliff Lane Unit 4, Orlando
$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
$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
Virtually Staged. 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
$359,900
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
$415,000
3 Beds ⋅ 3 Baths ⋅ O6417796 MLS
Don't miss this opportunity to live in the highly desirable WEDGEWOOD GROVES community at a FANTASTIC PRICE! This 3 BEDROOM, 2.5 BATH home features SOARING CEILINGS, abundant natural light, a WOOD-BURNING FIREPLACE, and a spacious OPEN FLOOR PLAN designed for comfortable living and entertaining. The RENOVATED KITCHEN is equipped with GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, and an OVERSIZED PANTRY, offering both style and functionality. The FIRST-FLOOR PRIMARY SUITE provides a private retreat with a SPA-INSPIRED BATHROOM featuring a HUGE WALK-IN SHOWER and CUSTOM WALK-IN CLOSET. Step outside to enjoy the OVERSIZED FENCED BACK YARD with plenty of room to relax, entertain, or play. Additional highlights include a COMMUNITY POOL, TENNIS COURTS, and an IDEAL LOCATION just minutes from DOWNTOWN ORLANDO, ORLANDO INTERNATIONAL AIRPORT, LAKE NONA, SR 408, and SR 528. Opportunities like this don't come along often!

2758 Waymeyer Dr, Orlando
$290,000
3 Beds ⋅ 3 Baths ⋅ O6418145 MLS ⋅ 038 BLDG.
Welcome home to this beautifully updated 2-story townhouse-style unit in a “condominium community” in the desirable Dover Green community. This charming residence features a complete kitchen and bathroom remodel in 2025. As a 2-story townhouse in this established, quiet community, it offers maintenance-free living with the HOA handling exterior upkeep, common grounds, and amenities. They just finished adding a BRAND NEW ROOF! The chef’s kitchen impresses with crisp white shaker-style cabinetry, premium quartz countertops, and a stylish herringbone marble-patterned backsplash. It is equipped with stainless steel appliances. This space is both functional and gorgeous. The spacious open-concept living area features light flooring that flows throughout the home and plenty of natural light. The thoughtful layout provides optimal flexibility and room for creativity, allowing you to arrange furniture and create the perfect setup exactly the way you want. This home offers 2.5 updated bathrooms. The primary bathroom features a chic gray vanity with white countertop, sleek fixtures, and a spacious marble-look tiled shower. Additional bathrooms include a convenient half bath downstairs and another full bath upstairs, all finished with fresh neutral tones, quality cabinetry, and modern details. Outside, enjoy a generous tiled back patio perfect for outdoor dining and entertaining. The fully fenced backyard benefits from a large mature shade tree just outside the fence that provides pleasant shade, along with plenty of space for relaxation and a covered grill area — an ideal extension of the living space. Community highlights in Dover Green include a junior Olympic-sized swimming pool, tennis and racquetball courts, and a clubhouse for events and gatherings. The community is known for its quiet, park-like setting in the desirable Dixie Belle neighborhood. With modern finishes, neutral tones, and thoughtful updates throughout, this move-in-ready home is truly turn-key. Located in the convenient 32812 zip code on a dead-end court, it provides easy access to major highways, downtown Orlando, dining, shopping, entertainment, and Central Florida attractions. Don’t miss out — schedule your private showing today!

2218 Mcmahon Court Unit 1038, Orlando
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