Homes for Sale Near Maitland Middle in Orlando - 7 homes

Remarks: Welcome home to this charming 3-bedroom, 2-bath residence in the desirable Woodsong community of East Orlando. Recently updated with new flooring throughout, updated kitchen, new plumbing and hurricane resistant window. Designed with an inviting split-bedroom floor plan, this home offers the perfect balance of privacy and functionality, featuring both a spacious family room and a bright living and dining area—ideal for everyday living and entertaining. Step into the enclosed rear porch, where you can relax with your morning coffee while overlooking the fully fenced backyard with no rear neighbors creating a peaceful setting that's hard to find. The generous lot provides plenty of space for outdoor gatherings, gardening, or simply enjoying Florida's beautiful weather. Location is everything, and this home delivers. Just minutes from UCF, Valencia College, Full Sail University, major highways, shopping, dining, and Orlando International Airport, you'll enjoy easy access to work and school. Whether you're a first-time homebuyer, downsizing, or searching for a smart investment opportunity, a desirable location, and the chance to make it your own. Don't miss this opportunity to own a home that combines comfort, convenience, and endless potential in one of East Orlando's most accessible neighborhoods. MORE PICTURES to come. Buyers agent to verify all measurements

Listing is courtesy of: FIRST LADY REALTY AND INVESTMENTS (407-383-4848)

Listing Agent: Mary Reed (407-383-4848)

Remarks: WELCOME HOME to your private lakefront oasis on Lake Pearl! This exceptional pool home with 165+ feet of waterfront sits on a rare 1.3-acre lot and offers unmatched privacy, stunning views, and direct access to one of Central Florida’s most desirable spring-fed, skiable lakes. Lake Pearl is private and owner-only access, perfect for boating, water skiing, paddleboarding, and lakeside relaxation. Outdoor living shines here with a 2020 TREX dock with boat lift and a unique bat house near the lake that provides natural mosquito control for year-round comfort. The partially fenced yard is perfect for pets and outdoor play while keeping a safe distance from the water. Inside, you're welcomed by a generously sized formal living and dining area, engineered hardwood flooring, and beautiful natural light. The kitchen, living room, breakfast nook, and back guest room/office all offer stunning lake views, making everyday moments feel special. Picture yourself watching the sunset over Lake Pearl while making dinner—a lifestyle that truly sets this home apart. The family room includes a cozy gas fireplace, allowing you to enjoy the glow of a fire while taking in breathtaking sunset views over the lake. This ideal split floorplan provides privacy and comfort. The master suite is a peaceful retreat featuring pool and lake views, plus a private entrance to the pool area for easy access to morning swims or relaxing spa evenings. The en-suite bathroom includes a walk-in closet and serene waterfront vistas. Step outside to your enclosed outdoor oasis with a PebbleTec pool, a heated spa, and a spacious screened lanai perfect for entertaining, lounging, or enjoying the lakefront breeze. The home is located in an A+ rated Winter Park school district and within an optional HOA that provides access to a community park, walking trails, and tennis courts—enhancing both recreation and neighborhood lifestyle. Perfectly situated, you're just minutes from the 417, UCF, Downtown Orlando, Park Avenue in Winter Park, and Orlando International Airport, offering unmatched convenience in a premier lakefront setting. Homes on Lake Pearl rarely come to market—don’t miss this incredible opportunity to own a true lakefront lifestyle property in Orlando.

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

Listing Agent: Maria Nunez (407-782-6512)

Remarks: Under contract-accepting backup offers. Nestled on a sprawling .59-acre homesite in East Orlando, this one-of-a-kind pool home is filled with character, architectural charm, and endless potential for the buyer with vision. Ideally located near Lake Pearl you’ll enjoy easy access to UCF, Research Park, SR 408, SR 417, Waterford Lakes Town Center, and Oviedo’s shopping, dining, and entertainment options. From the moment you enter, you’re welcomed by a spacious formal dining room to the left and an oversized formal living room to the right, both enhanced by large picture windows that flood the home with natural light. The split floor plan offers privacy, with the generous primary suite tucked away on one side of the home and three spacious guest bedrooms with a full bath and a half bath on the opposite wing. The heart of the home is the updated kitchen featuring quartz countertops, shaker-style cabinetry, stainless steel appliances, a breakfast peninsula, skylight, and a convenient pass-through to the expansive Florida room, all while overlooking the family room with vaulted ceilings, exposed wood beams, and timeless character. Throughout the home you’ll find unique details including tiled and brick archways, wainscoting and plantation shutters in one of the secondary bedrooms, and an updated pool bath with a quartz vanity and shaker cabinetry. New sliding glass doors open to the 26’ x 10’ covered Florida room and screened lanai, creating seamless indoor-outdoor living. The primary bath offers a truly unique feature—a completely enclosed private atrium accessed through sliding glass doors, ready to become your personal garden retreat, outdoor shower oasis, meditation space, or secluded sanctuary. Outside, enjoy a large uncovered pool, gazebo, expansive backyard, and a detached workshop with electricity that is perfect for hobbies, projects, storage, or a future creative workspace. With no HOA restrictions on parking, there’s plenty of room for your boat, RV, trailers, and toys. NEW ROOF in 2025. If you’ve been searching for a home with soul, charm, and room to make it your own, this rare East Orlando opportunity is one you won’t want to miss.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Daniel Teston (407-509-0211)

Remarks: Wake up to a beautiful fire-lit sunrise over the water. On a private 1.6-acre lot with 150 feet of frontage along 83-acre Lake Georgia, a rare ski-friendly lake in East Orlando, 9889 Lake Georgia Drive is an extraordinary custom-built lakefront estate where every detail has been sourced, engineered and installed at the highest level. Offering five bedrooms and six and one-half baths, this is a home defined by scale and craftsmanship. Pass through the sliding gated entry, follow the brick-paved driveway toward the striking custom pivot door, framed in limestone and accented with Turkish stone, and you understand immediately that this is no ordinary address. Inside, the home opens dramatically as 48-by-48-inch porcelain tile floors extend beneath soaring volume ceilings, flanked by floor-to-ceiling windows that draw the lake directly into the living space. Custom floating stairs rise with sculptural elegance beside a crystal chandelier and glass railings, while curated designer lighting sets a tone of refined permanence throughout. A stacked-stone fireplace anchors the great room, and a wet bar with gas fireplace extends the entertaining space. The chef's kitchen is anchored by a large waterfall-edge quartz island, complemented by German custom high-gloss cabinetry, premium stainless steel appliances, a built-in Thermador espresso machine and a porcelain tile backsplash. A walk-in pantry adds everyday function to a home designed to be lived in as beautifully as it looks. The primary suite offers lake views, dual quartz vanities, glass-enclosed rain showers, a handheld bidet and a walk-in closet with custom organizers. Additional en-suite bedrooms feature luxury vinyl plank floors and designer baths with backlit mirrors and matte fixtures. Most rooms are wired for interior and exterior audio, with surround sound in the media and family rooms, all controllable by phone or remote. A dedicated home office, a game/media room ready for billiards, and a second-floor loft complete the interior. Outside, resort-caliber amenities await. A magnificent summer kitchen is outfitted with a 48-inch barbecue, four gas burners, granite counters, ice maker, mini-refrigerator and sink, all beneath a tongue-and-groove wood porch ceiling with automatic screens. The newly resurfaced lap pool features a spa, sun deck, water feature and Pebble Tec surface, surrounded by 2,000 square feet of paver decking and adjoined by a nine-person spa. Above, a balcony finished with artificial turf delivers panoramic lake views. On the water, a large covered boat dock with upper deck, boat hoist, private slip and Sea-Doo storage, plus a private boat ramp on site, completes the picture. Additional highlights include a 22,000-kilowatt generator, dual tankless water heaters, water filtration and softening, $25,000 in motorized custom blinds throughout, an insulated three-car garage with refinished floors and custom storage racks, a security surveillance system, LED lighting, gas-infused double-pane windows and doors, a lake-fed irrigation system and parking for 12-plus vehicles. Ideally located, zoned for Winter Park schools with an Orlando address, just over three miles from UCF and the Central Florida Research Park, home to Lockheed Martin, Northrop Grumman, Raytheon, Boeing and L3Harris. Downtown Orlando and Orlando Health and AdventHealth medical centers are roughly 12 miles west, while Park Avenue's boutiques and dining are minutes away. This is lakefront living at its best.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Audra Wilks (407-252-8582)

Remarks: Investor special- “BACK ON MARKET” Almost completed home nestled in Watermill Cove. Situated on an oversized, nearly half-acre corner lot. Whether you're looking to make a long-term investment or flip take advantage of “OVER $200k IN INSTANT EQUITY!” The majority of the renovation has already been done, only the final touches, like pool, kitchen, and minor finishes needed. Most of the material to finish the job is included. Don't miss out on your chance to secure this property with so much value and potential. Second time on market, seller had full price offers but decided to not sell and complete the flip, they were unable to do so. Were back and ready to sell! Financing available

Listing is courtesy of: EXP REALTY LLC (407-305-4300)

Listing Agent: Eddie Lopez (321-310-0323)

Remarks: Welcome to this beautifully presented home in Woodside Village, an established lakeside community on the shores of Lake Pearl. Situated on a spacious corner lot, this 3-bedroom, 2-bath residence offers over 1,700 square feet of comfortable living space. An inviting entry foyer opens to generous living and dining spaces, , where abundant natural light, warm wood flooring, and crown molding create an atmosphere that feels both comfortable and refined. The family room is anchored by a vaulted ceiling and cozy wood-burning fireplace, while French doors open to an oversized screened porch that naturally extends the living space outdoors. The kitchen blends timeless style with everyday functionality, featuring white shaker-style cabinetry, granite countertops, stainless steel appliances, subway tile backsplash, under-cabinet lighting, and plentiful prep space. A window above the sink overlooks the backyard, while the charming breakfast area offers direct access to the porch—ideal for morning coffee or casual dining. The spacious primary suite creates a relaxing retreat with a wall of French doors opening to the screened porch. The updated ensuite bath includes dual sinks and an oversized walk-in shower with built-in seating. A split-bedroom layout enhances privacy, with two additional bedrooms and an updated guest bath thoughtfully positioned on the opposite side of the home. A versatile laundry room adds exceptional functionality with a front-loading washer and dryer, folding space, extra storage, and a built-in desk area perfect for managing household tasks or working from home. Step outside to enjoy the expansive screened porch overlooking a beautifully landscaped, fenced backyard complete with paver patios and market lighting—perfect for outdoor gatherings. Additional highlights include newer windows, a well for irrigation, a Generac generator, and an oversized two-car garage with built-in storage cabinets, all complemented by the home’s desirable corner lot setting within this established lakeside neighborhood. Woodside Village residents enjoy exclusive access to a private boat ramp on Lake Pearl, a lakeside pool, playground, and tennis/pickleball courts. The home is also zoned for highly sought-after schools: Lakemont Elementary, Maitland Middle, and Winter Park High. Don’t miss the opportunity to own this exceptional home —where comfort, style, and community come together. Water Heater 2026, A/C 2022, Plumbing 2012, Roof 12/12.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Mary Colton (407-222-7388)

Remarks: Large lot, terrific location, top notch schools (Lakemont, Maitland and Winter Park HS), wonderfully maintained 3 bedroom PLUS office is the package this home offers! Home is centrally located making travel to downtown Winter Park or downtown Orlando very convenient. Easy access north and south with the 417 very close by! This home has been very well maintained with a newer roof and home was re piped. The floor plan offers 3 generous sized bedrooms, a dedicated office, formal dining room, kitchen with an eat in dinette, a generous living room with wood burning fireplace and a screened in lanai to enjoy the weather in fall and spring!! The Kitchen has ample storage with a pantry and cabinets that have pull out shelving. The home has no carpet and features a soft cream tile and bamboo wood flooring. Living areas, kitchen and dining room feature beautiful plantation shutters that bring elegance to these spaces. Home sits on a third of an acre in a small cul de sac corner lot. Plenty of room for a soccer game in the front yard or a pool in the back. There is a quaint front porch to enjoy friends and neighbors. Plenty of parking with extra long driveway and a 2 car garage. Perfect for the buyer seeking great schools, convenient commuting, and move-in-ready condition.

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

Listing Agent: Vonda Fields (321-438-6906)