Homes for Sale Near Conway Middle in Orlando - 103 homes

Remarks: Under contract-accepting backup offers. Welcome to 4536 Simmons Road—an updated and versatile property offering space, flexibility, and an unbeatable location in the heart of Orlando. Situated on an expansive .35-acre lot, this home delivers both comfort and functionality with room to grow, entertain, and store all your toys. Step inside to an open-concept living and dining area filled with natural light, seamlessly flowing into a beautifully updated kitchen featuring granite countertops and a massive island—perfect for gathering, cooking, and everyday living. The split-bedroom floor plan provides added privacy, while the oversized Florida room offers incredible bonus space for relaxing, entertaining, or creating your ideal indoor-outdoor retreat. Practical features abound, including an indoor laundry room, two carports, and ample off-street parking with plenty of space for multiple vehicles, boats, or recreational equipment. The fully fenced yard adds privacy and room to roam. A standout feature of this property is the detached studio/in-law suite, complete with its own kitchenette and full bath—ideal for guests, extended family, rental income, or a private workspace. Conveniently located just 10 minutes from Orlando International Airport and 15 minutes to Downtown Orlando, this home offers easy access to everything Central Florida has to offer. Zoned for Boone High School. A rare combination of space, flexibility, and location—this is one you don’t want to miss.

Listing is courtesy of: LAKESIDE REALTY (321-303-2850)

Listing Agent: Kristen Whipple (407-493-6255)

Remarks: Beautiful Condo with Peaceful Nature Views! Enjoy serene views of trees and local wildlife from this charming condo located in a desirable gated community. Perfect as an investment property or a starter home, this residence offers a low HOA and access to multiple amenities. Inside, you’ll find fresh interior paint, vinyl flooring, and updated kitchen cabinets, creating a clean and modern feel throughout. Conveniently situated near major highways, shopping, dining, and the airport—this location truly has it all.

Listing is courtesy of: PREFERRED REAL ESTATE BROKERS II (407-440-4900)

Listing Agent: Marilyn Diez (689-266-8267)

Remarks: Welcome to this beautifully maintained condo at Regency Gardens, located in the heart of Orlando. This second-floor unit offers a bright, open layout with comfortable living and dining spaces, perfect for both relaxing and entertaining. The kitchen features ample cabinet storage and flows seamlessly into the main living area. Spacious bedrooms provide a peaceful retreat, while the private balcony is ideal for enjoying your morning coffee or unwinding in the evening. Situated in a well-kept community with convenient access to major highways, shopping, dining, and Orlando International Airport, this condo is perfect for homeowners or investors alike. Whether you’re looking for a primary residence, second home, or rental opportunity, this centrally located property offers comfort, convenience, and value in one of Orlando’s most accessible areas.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)

Listing Agent: Chase Mckeel (407-538-1094)

Remarks: Under contract-accepting backup offers. Seller is offering a 1% lender credit when using the preferred lender. Why rent when you can own, or secure a solid investment opportunity in a highly convenient Orlando location? This 2-bedroom, 2-bath condo is located in the gated Wimbledon community and offers top-floor living with no upstairs neighbors for added privacy. The layout is functional and filled with natural light, creating a comfortable space for everyday living or strong rental potential. A cozy fireplace adds character to the main living area, creating a warm focal point you don’t often find in condo living. Enjoy a private screened-in patio, perfect for relaxing or unwinding, along with in-unit laundry hookups for added convenience. The open living and dining areas flow easily into the kitchen, making the space feel connected and practical. Wimbledon offers a full range of amenities including a community pool, tennis courts, fitness center, clubhouse, and maintained grounds, all within a gated setting. The HOA includes these amenities, providing easy, low-maintenance living. Located along Semoran Blvd, you’re just minutes from Orlando International Airport, major highways including 408 and 417, and a wide range of shopping, dining, and everyday conveniences. Easy access to Downtown Orlando and Lake Nona makes this a highly connected and desirable area. Move-in ready with room to make it your own over time, this is a great opportunity for a primary residence or investment in an established Orlando community. Don’t hesitate and schedule your showing today.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Cassandra King (407-462-2762)

Remarks: Excellent location in the heart of Orlando! This centrally located condominium offers controlled access and convenient access to Highway 408. Ideally situated near Orlando International Airport, Valencia College, Downtown Orlando, supermarkets, restaurants, and major shopping destinations. This property is a fantastic opportunity for first-time homebuyers, investors, or anyone seeking comfort, convenience, and accessibility within an affordable and well-connected community. The unit also includes a washer and dryer for added convenience.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Miriam Rodriguez Rivera (407-225-2895)

Remarks: Under contract-accepting backup offers. Prime Location + Income Potential! This 3-bedroom, 2.5-bath half duplex is ideally located just 10 minutes from Orlando International Airport and about 20 minutes to all major attractions—putting you right where you want to be. Major updates include a roof replaced in 2023 and A/C from 2021 (exterior unit). Inside, the home features an updated kitchen and bathrooms with granite countertops and newer cabinetry, along with vinyl flooring throughout and tile in the bathrooms. All appliances are included. The layout feels open and inviting with vaulted ceilings, skylights, and a cozy fireplace that adds character to the main living space. There’s also a comfortable dinette area for everyday meals or casual gatherings. Step outside to a cute and spacious patio, perfect for barbecues or relaxing, and enjoy the convenience of the community pool just a short walk away. Some photos have been virtually staged to show the home’s potential.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Patti Alonzo (407-432-2777)

Remarks: Single Family Home Alert! - Welcome to 4490 Simmons Road, a beautifully updated and move-in ready home located in the desirable Conway / Gatlin Gardens area of Orlando. This charming single-story residence blends classic mid-century character with modern finishes and thoughtful upgrades throughout. Offering two bedrooms, two full bathrooms, and approximately 1,334 square feet of living space on a generous 7,500 square-foot lot, this home perfectly balances warmth, functionality, and location—all with no HOA. From the moment you arrive, you’ll notice the inviting curb appeal and large front deck that stretches across the home, creating the perfect space for morning coffee, outdoor dining, or entertaining guests in true Florida style. Inside, natural light fills the open floor plan, creating an airy, welcoming feel from the living room through to the dining and kitchen areas. You’ll fall in love with the rich elegance of the wood plank–look tile, installed throughout the home, which combines timeless style with modern durability. The kitchen has been beautifully updated with gleaming quartz countertops, modern cabinetry, and stainless-steel appliances—all included in the sale. In 2025, the seller installed a new microwave and new washer, giving you the peace of mind that key appliances are fresh and efficient. Just off the kitchen, the spacious dining room features a stunning quartz beverage-serving area with ample cabinetry—ideal for entertaining, a coffee bar, or extra storage. The open layout provides a seamless flow for gatherings while maintaining the cozy intimacy of a traditional home. Both bedrooms are generously sized, with convenient access to two full baths, offering flexibility for guests, a home office, or a roommate setup. The home’s interior laundry area adds convenience and functionality to daily living. Structural and mechanical peace of mind come with the roof, which is only about six years old (2019), ensuring durability and reduced maintenance for years to come. Outdoor living shines here—Installed in July 2025, the vinyl fencing adds privacy and definition to the backyard, creating an inviting space for gardening, outdoor gatherings, or relaxing under the Florida evening sky. The property’s size offers plenty of space for entertaining, adding a patio, or even a future expansion. The home includes tile flooring, central A/C and heat, and public utilities, combining efficiency with comfort. Its convenient location puts you minutes from the SoDo District, Orlando International Airport, Downtown Orlando, and the major roadways of 408 and 528, making commuting simple and shopping and dining easily accessible. Zoned for highly regarded Shenandoah Elementary, Conway Middle, and Boone High School, this home offers an exceptional lifestyle opportunity in one of Orlando’s most established neighborhoods. With no HOA, a nearly new roof, quartz-finish upgrades, stainless appliances, a brand-new fence, a huge front deck, and 2025 appliance updates, 4490 Simmons Road delivers move-in readiness and timeless appeal. Whether you’re a first-time buyer, downsizing, or looking for an investment property in a sought-after central location, this home combines character, comfort, and convenience in a way that’s truly hard to find in today’s market. Schedule your showing today and experience all that this lovingly maintained Conway gem has to offer.

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Scott Pettengill, Llc (207-735-4270)

Remarks: LOCATION ! LOCATION! just about 6 minutes from Downtown and the Orlando International AIRPORT. This Stunning FIRST FLOOR 1 bedroom 1 bathroom Condo in the desirable resort style Regency Garden Community. Located at First Floor Features an open floor plan, Granite counter top in the kitchen and a bright living area with a fireplace. You will enjoy the screened private porch also all the amenities that include pool, fitness Center, club house, tennis court, playgrounds and more. A shopping Center with a Walmart Neighborhood is across the street for your convenience. The water is already included in the HOA payment. Calling investors for an extra income or it could be your home sweet home for a very convenient price.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Hilma Lemus Lamothe (407-617-9516)

Remarks: Beautiful home that lives much larger than it appears. If you drive past this one…you’d be missing one of the best values in the Conway area at under $400K. Come Check out this move-in ready 3-bedroom, 2-bath home offers a surprisingly spacious layout with multiple living areas that create flexibility for everyday living, entertaining, or working from home. Inside, you’ll find a bright and airy home with an open floor plan, updated flooring, a bright and inviting living space, and a dining area overlooking the backyard. The additional living/flex space makes this home feel significantly larger than expected. Come entertain in the large kitchen with loads of storage space and large granite countertops. Relax and enjoy piece of mind with major updates have already be done for you, including a Newer Roof (2021) and an HVAC system isntalled in 2022—giving you peace of mind and saving you thousands. Step outside to a large private, partially fenced backyard with plenty of room to relax or create your ideal outdoor space. Plenty of space to add a summer kitchen, pool, or BBQ. The possibilities are endless and of course NO HOA!!!! Location perks: Your new home is Near the Conway Chain of Lakes where there is boating, fishing, and plenty of water activities to keep you entertained and is within 3-4 miles to the public boat ramp. Enjoy your morning cup of coffee at FoxTail Coffee, Local brews in the evening at Hourglass Brewery. Relax and Stretch at the Peaceful Peacock and great food at the Hourglass Social Hall that are all within 4 miles. In berber Park (less than 3 miles away) you can experience activities such as pickle ball, splash pad, or even the outdoor rolling Hockey Rinks just to name a few. Minutes to Barber Park, & the Hourglass District, your new home is also less than 5 iles to Downtown Orlando. Easy access to Orlando International Airport, UCF & major attractions. Zoned for Conway Elementary, Conway Middle & Boone High. Homes with this much usable space and no HOA at this price point in Conway Gardens area and near Downtown Orlando are hard to find—come see it in person before it’s gone.

Listing is courtesy of: HOMEVINE REALTY (407-929-4632)

Listing Agent: Camille Ruiz (407-929-4632)

Remarks: Under contract-accepting backup offers. Investor opportunity! Beautiful 1-bedroom, 1-bath condo located in a well-maintained community in the heart of Orlando. This second-floor unit offers 846 sq ft of bright, functional living space and features brand-new laminate flooring throughout and fresh interior paint, giving the home a clean, modern feel. AC 1.5 years old // The community offers resort-style amenities, including a swimming pool, clubhouse, and beautifully landscaped common areas. The HOA covers cable TV, high-speed internet, sewer, trash, pest control, exterior maintenance, and full access to amenities. // 5 miles from FULL SAIL UNIVERSITY and 13 miles UCF! // Conveniently located just minutes from Orlando International Airport, major highways (528 & 408), shopping, dining, and Downtown Orlando, making this an excellent opportunity for both owner-occupants and investors. *** HOA information, including fees, rules, and restrictions, measurements, etc. is believed to be accurate but not guaranteed. Buyers are advised to independently verify all HOA details and governing documents prior to closing ***

Listing is courtesy of: BRICKELL REALTY GROUP INTERNATIONAL LLC (305-799-6410)

Listing Agent: Alva Ricci (801-615-4385)

Remarks: One or more photo(s) has been virtually staged. **NEW PRICE** Welcome to 3640 Sickle Street in Orlando, a beautifully refreshed home offering 1,661 square feet of well-designed living space with 3 bedrooms and 2 bathrooms in a desirable split floor plan. Vaulted ceilings create an open, airy feel, while recent updates—including a newly installed HVAC system, whole-house repipe, brand-new carpeting, and fresh interior paint throughout—make this home truly move-in ready. Located within a gated community, the property also features a fully fenced backyard, perfect for pets, play, or peaceful evenings outdoors. Set on a quiet street directly across from Lake Warren Park, you’ll enjoy immediate access to tennis courts, playgrounds, picnic areas, and serene lakefront views—no membership required, just step outside. All this, just minutes from Orlando International Airport, downtown Orlando, and the scenic shores of Lake Conway, makes this home a rare blend of comfort, convenience, and classic Florida living. A solid home, in a great spot, with the big updates already done—this one checks all the boxes.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: Welcome to this condominium located in the established Registry at Michigan community. This residence features a bright and functional layout, a well-equipped kitchen with a breakfast bar, a private balcony, and an in-unit laundry area for added convenience. Located in a gated community offering a fitness center, two swimming pools, hot tub, and clubhouse. The HOA includes water, basic cable and internet, exterior maintenance, onsite management, pest control, and trash service. Tenant-occupied with a lease in place, offering immediate rental income for investors. Conveniently located near major highways, shopping, dining, Downtown Orlando, and Orlando International Airport, providing easy access to everyday conveniences and major employment centers.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Daniela Bou Mansour (305-590-3843)

Remarks: A 30 year experienced Orlando licensed contractor has redesigned and renovated the interior of this house for today's new home enjoyment. The house has not been lived in since the renovation. Some of the new features are large kitchen with new custom wood cabinets and quartz tops, new GE Profile appliances, large island with seating, walk-in pantry, separate laundry room, kitchen open to view custom wood burning brick fireplace in family room, and also a full table size nook, all complemented by vaulted ceilings. This split plan home has 3 sets of new French Doors opening to a large, vaulted ceiling porch ready for a new summer kitchen and swimming pool. In the renovation all walls and ceilings have been primed and finish coated with Sherwin Williams paint. The A/C system was modified to include a return air in each bedroom. A new garage door with a side mount electric opener and exterior keypad. The primary bedroom has an adjoining room area ideal for nursery, exercise, working or relaxing, a multi-shelved/rod walk-in closet, 2-person shower with 3 heads and a five-foot bench, separate sink cabinets and mirrors. The exterior is stucco over concrete block with detailed custom brick columns and accents. If you want new at a discounted price, this house deserves a visit. Some seller financing available.

Listing is courtesy of: RUBY DAVIS, BROKER (407-721-7690)

Listing Agent: Ruby Davis (407-721-7690)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this charming ground-floor condominium in the sought-after Coach Homes of Mariners Village, conveniently between downtown Orlando and Orlando International Airport. This 1,192-square-foot, two-bedroom, two-bath residence features an attached single-car garage with additional driveway parking, offering comfort and convenience. Inside, a bright and open floor plan creates a welcoming atmosphere. The well-appointed kitchen provides ample cabinetry and counter space, while the primary suite offers a private en-suite bath. A second bedroom provides flexibility for guests or a home office, and an in-unit laundry room enhances everyday convenience. Enjoy the screened rear patio, which overlooks lush green space, providing a serene retreat. Residents can enjoy the community pool just a short walk away, an ideal place to relax and unwind. Zoned for the highly rated Boone High School, this home offers access to top-tier education, adding to its appeal for those seeking quality schools in the area. Condominium fees include cable, internet, water, trash and community maintenance, ensuring a hassle-free lifestyle. With easy access to shopping, dining, major roadways and recreational amenities, this residence is ideally positioned. Schedule your showing today.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)

Listing Agent: Shane Carson (407-462-1310)

Remarks: This 4/2 close to UCF, 436, and Orlando Int airport has it all: screened in pool area, lot space for days w/ only 1 neighbor, and split floorplan, perfect for any large family. The refined interior touches like the gold handles on the soft blue cabinets & solid stone marble countertops in the bathrooms & kitchen gives the home a royal flavor. Some repairs/updating needed. Serious about buying? The seller is serious about selling! Call today to view, easy to show!

Listing is courtesy of: TOWER TEAM REALTY, LLC (786-233-4959)

Listing Agent: Brandon Ford (305-305-0105)

Remarks: Welcome to Regency Gardens—an exceptional opportunity for both homeowners and investors alike. Ideally located just minutes from shopping, dining, and Orlando International Airport, this 2-bedroom, 2-bath condominium offers convenience, comfort, and strong potential. Inside, you’ll find a spacious living area, walk-in closets, and the added convenience of an in-unit washer and dryer—perfect for everyday living or attracting quality tenants. For homeowners, this condo provides a low-maintenance lifestyle in a well-located community with amenities including a pool, clubhouse, and recreational spaces. For investors, the community’s management services and desirable location make it a compelling rental opportunity with consistent demand. Whether you're looking to settle in or expand your portfolio, this well-maintained property delivers value and versatility in the heart of Orlando. Seller financing available. Don’t miss your chance to secure a property that works for you—schedule your showing today.

Listing is courtesy of: FLORIDA TOP REALTY (407-731-9938)

Listing Agent: Anna Cheng Cheung (407-731-9938)

Remarks: There’s something special about a home that gives you a starting point—and the freedom to make it entirely your own. Tucked into the heart of Orlando, this 3-bedroom ranch-style home offers a layout that feels open, functional, and ready for its next chapter. Inside, the wide-open living space creates an easy flow from room to room, anchored by wood flooring and modern recessed lighting that bring warmth and dimension throughout. The kitchen features rich wood cabinetry and a layout that invites reimagining—whether you keep it classic or take it to the next level. Step outside to a screened-in back porch and fully fenced yard, giving you a private outdoor space with plenty of room to design your own retreat—garden, fire pit, or entertaining area, the choice is yours. Set in a location that puts you right in the middle of it all, you’re just minutes from Downtown Orlando, major roadways, shopping, dining, and everyday essentials. It’s the kind of spot that makes both daily living and long-term value make sense. For buyers or investors who see beyond the ordinary, this is a home with direction, flexibility, and upside—ready to become something truly personal.

Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)

Listing Agent: David Weiss (407-765-9020)

Remarks: Step into comfort and style in this beautifully maintained 3-bedroom, 2-bathroom home featuring a spacious loft and eye-catching spiral staircase that adds architectural charm and character. The fully renovated kitchen is a standout, boasting sleek quartz countertops, a modern tile backsplash, brand-new stainless steel appliances, and rich solid wood cabinetry—perfect for both everyday living and entertaining. Wood-grain tile flows seamlessly throughout the home, offering durability with a warm, elegant feel. Gather around the stunning brick fireplace, which serves as a cozy focal point in the living space, while abundant natural light fills every room, creating a bright and inviting atmosphere. Enjoy ample storage throughout, making organization effortless. Step outside to your private outdoor lanai—an ideal spot for relaxing or entertaining on warm Florida evenings. Located in the desirable Bryn Mawr community, residents enjoy access to an array of amenities including two sparkling pools, a scenic lake perfect for duck spotting, tennis and pickleball courts, a playground, and a clubhouse for social gatherings and events. The neighborhood is known for its peaceful, walkable setting and convenient proximity to shopping, major highways, and top-rated schools. Major updates provide added peace of mind, including a roof replaced in 2018, AC system updated in 2017 with a new interior unit installed in 2025, and a transferable termite bond that has been consistently maintained. This home offers the perfect blend of comfort, style, and community living—ready for you to move in and enjoy.

Listing is courtesy of: COLONIALTOWN REALTY (407-896-7300)

Listing Agent: Brooke Lambert (407-223-2558)

Remarks: **Price Improvement** Discover a rare opportunity to own a true lakefront gem in the highly sought-after Conway area, just minutes from the vibrant SODO District. This spacious 4-bedroom, 3-bathroom home offers over 2,500 square feet of living space and sits on an impressive half-acre lot with sweeping views of the lake. Built in 1964 and cherished by its original owner for more than 60 years, this residence is filled with character and timeless charm. While the home has not been updated, it provides the perfect canvas for those who wish to create their dream lakefront retreat. Generously sized living areas, a functional floorplan, and plenty of natural light showcase the potential this property holds. Outside, the large lot provides room to enjoy the tranquility of lakefront living, with ample space for outdoor entertaining, gardening, or even adding a pool. The peaceful setting is perfectly balanced by its convenient location close to downtown Orlando, shopping, dining, and top schools. This is more than just a house—it’s a chance to own a piece of Orlando history and create a lakefront lifestyle tailored to you.

Listing is courtesy of: THOMAS LYNNE REALTY GROUP LLC (407-808-0899)

Listing Agent: Jeffrey Bauer (407-334-8056)

Remarks: PRICE IMPROVEMENT! Welcome to this charming 3 bedroom, 2 bathroom single-family home located on an oversized corner lot and nestled in the desirable Conway area. Many wonderful features this home has to offer includes new roof, new vinyl fence, open layout with laminate wood and tile flooring, updated kitchen and bathrooms. The living room and guest bedroom includes sliding doors, leading to the screened backyard patio. Step outside and enjoy true Florida living in your spacious backyard paradise with mature landscaping, a new vinyl fence and screened patio, perfect for entertaining friends and family. EXCELLENT LOCATION zoned for top-rated schools, property benefits from a quiet neighborhood feel while remaining conveniently close to major roadways, the Orlando International Airport and downtown amenities. Come take a tour of this charming 3 bedroom, 2 bathroom single-family home located on a spacious oversized corner lot today!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Carlos Rocha (321-662-3344)