Homes for Sale Near Maitland Middle in Orlando - 12 homes

Remarks: 4238 Watermill Dr, a lakefront opportunity in the heart of Winter Park. This property offers serene lake views and a peaceful setting, with close proximity to the best dining, shopping, and entertainment the area has to offer. The home features a bright sunroom perfect for relaxing or entertaining while enjoying the water backdrop. Whether you're looking to personalize your dream home or secure your next investment, this property presents a rare chance to add value in a highly desirable neighborhood. Zoned for highly sought-after Winter Park High School, one of the top-rated schools in Central Florida, this home offers strong long-term appeal for both homeowners and renters alike. With a low HOA and priced to sell, this is an exceptional opportunity for investors, renovators, or buyers looking to get into a premium location at a competitive price point. Waterfront properties in this area rarely last, don’t miss your chance.

Listing is courtesy of: KARDOSH REALTY (407-499-4466)

Listing Agent: Andre Reis (570-369-0131)

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)

Remarks: Nestled on a quiet corner lot within a prestigious cul-de-sac surrounded by million-dollar homes, this all-brick ranch residence is perfectly positioned between two serene lakes—Lake Pearl and Lake Burkett—in the highly sought-after Winter Park School District. Mature landscaping enhances the home's stately curb appeal, while views of both lakes can be admired from various points around the cul-de-sac. Inside, an abundance of living space awaits, featuring four bedrooms, two bathrooms, two separate living areas, a formal dining room, and two bonus rooms that overlook the screened pool and spa. A charming cabana hut in the backyard offers the ideal setting for summer barbecues and leisurely afternoons. Upon entering, the formal dining room greets you to the left, while a comfortable living area unfolds before you. The family room impresses with soaring vaulted ceilings that draw the eye upward to a striking stone wood-burning fireplace. This inviting space flows seamlessly into the kitchen on one side and the sunlit Florida room on the other. The Florida room, which overlooks the screened pool, leads to an additional bonus room bathed in natural light from expansive picture windows. The master bedroom, situated on the north side of the home, opens conveniently to a Florida room that provides direct access to the pool area. The master bathroom has been completely renovated, showcasing exquisite marble patterned floors in the stand-up shower, a new vanity, a private water closet, and his-and-hers closets—a truly luxurious retreat. One additional bedroom resides on this wing of the home, while the remaining two bedrooms are positioned on the opposite side of the living spaces, creating a thoughtful split-bedroom floor plan. The updated guest bathroom, also located on the side with the split bedrooms, offers both convenience for visitors and privacy for the master suite. The property has been meticulously maintained, with a new roof installed in 2018, a re-piping of the home, and both bathrooms recently renovated. Additional highlights include vaulted ceilings, a stone fireplace, a split floor plan, a fenced backyard, and a cabana area overlooking a large solar-heated pool with an in-ground spa—all within a screened porch enclosure. The yard is exceptionally pet-friendly, offering plenty of room to run and play. With its extraordinary features, recent upgrades, and unmatched location, this exceptional property will not last long.

Listing is courtesy of: MAVREALTY (727-314-3942)

Listing Agent: Robert Kirkwood, Iv (321-297-6489)

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: Welcome to this beautiful updated property offering comfort, functionality, and an incredible Florida lifestyle! This move-in-ready open concept home features numerous major upgrades, giving peace of mind for years to come. Enjoy a new AC (2025), new water heater (2025), roof replaced in 2021, and the home was replumbed in 2021. The property also includes new windows, tile flooring throughout, and a new shed for additional storage and convenience. Step outside and appreciate the mature palm trees, which are included with the property, creating a true tropical setting. Relax and unwind in the ADA-compliant walk-in hot tub, designed for comfort and accessibility. The home also comes equipped with a solar system that will be paid off at closing depending on the sales price. If not paid at closing, the solar loan is assumable, providing flexibility for the new owner. The system has a solar inverter with a 50 Amp RV plug, a 120 AC plug, cable/satellite and fiber. It also has a 30 generator plug to a 10 bank transfer switch in the garage that powers most of the house. Residents of Watermill enjoy access to a range of community amenities including tennis and basketball courts, playgrounds, scenic walking trails, and a private dock. Conveniently located just: 5 miles from UCF’s main campus 7.5 miles to Waterford Lakes Town Center 20–25 miles to Downtown Orlando, Kia Center, Orlando International Airport, and major attractions such as Universal Studios, CityWalk, International Drive, and the Orange County Convention Center Whether you're a first-time buyer, a growing family, or looking for your forever home, this property checks all the boxes. Schedule your private tour today—this one won’t last!

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

Listing Agent: Monica Cuervo (407-701-3095)

Remarks: Under contract-accepting backup offers. Special opportunity in Woodside Village, one of the University Area’s most desirable communities. Enjoy tree lined streets, sidewalks, large homesites, and outstanding amenities including lake access, community pool, tennis courts, playground, dock, and fishing pier—all part of the luxury lifestyle this neighborhood is known for. This well designed 3 bedroom home lives larger than its 1,600 sq. ft. layout. Features include a fireplaced family room, oversized living and dining areas, and an updated kitchen with stainless steel appliances and a built in island table. Large windows overlook the expansive, fully fenced backyard, and the covered, screened lanai extends your living space outdoors. The primary suite offers a remodeled primary bath with zero threshold walk in shower and a built in custom closet. Zoned for Winter Park High School, with excellent supporting middle and elementary schools. To make your move even easier, the seller is providing a one-year AHS Home Warranty—a valuable bonus that gives you added comfort and confidence.

Listing is courtesy of: REAL LIVING R E SOLUTIONS (407-253-1377)

Listing Agent: Tony Marino (407-468-2004)

Remarks: Under contract-accepting backup offers. Welcome to one of East Orlando’s hidden gems in the highly sought-after community of Georgia Cove. Tucked near Lake Georgia with immediate access to 417, close to UCF, shopping, dining, and downtown Orlando, this stunning corner-lot pool home combines space, style, and functionality in one unforgettable package. Offering 4 bedrooms, 3 full bathrooms + office/den, and 2,682 square feet of living space, this home also features a spacious 3-car garage and a resort-style heated saltwater pool retreat in the fully fenced backyard. Stepping inside you’re immediately greeted by soaring vaulted ceilings and a dramatic split staircase that creates a grand first impression. The elegant foyer opens to formal living and dining spaces while the staircase uniquely wraps around to provide access from both the front entry and the main living and kitchen areas, adding both beauty and functionality to the layout. The heart of the home is the beautifully updated country-chic kitchen featuring granite countertops, decorative tile backsplash, stainless steel appliances, a double oven range, upgraded cabinetry, and an extended butcher block island perfect for gathering and entertaining. Above the microwave, a custom wood hood-style feature adds warmth and charm, while the oversized walk-in pantry with a swing door and decorative chicken wire detail delivers character rarely found in homes. Downstairs also includes a private office/den with French doors conveniently located next to a full bathroom, making it an ideal setup for guests, multi-generational living, or a potential fifth bedroom option. Throughout the home, thoughtful design details create warmth and personality, including wood accents around windows, custom barn doors, and inviting living spaces filled with natural light. Upstairs features luxury vinyl plank flooring throughout and leads to four spacious bedrooms, including an incredible primary suite overlooking the backyard oasis. The primary bedroom showcases a beautiful wood accent wall, dual oversized walk-in closets, and French doors with enclosed blinds opening to a private covered balcony complete with roll-down privacy shades. A dedicated brand new mini-split system was added to the primary suite for those who prefer an extra-cool sleeping environment. The fully renovated primary bathroom feels like a spa retreat with a frameless glass shower enclosure, decorative tilework, oversized niche, freestanding soaking tub beneath a chandelier, and upgraded vanities, mirrors, fixtures, and hardware throughout. Additional upstairs bedrooms share an updated secondary bathroom featuring modern tile, black hardware accents, updated vanity, mirror, and lighting. Step outside through the rear sliders to your private backyard retreat featuring a heated saltwater pool with sun shelf, beautiful rock landscaping, a fire pit gathering area with string lighting, a storage shed, and plenty of green space to enjoy. The fully wood-fenced backyard creates the perfect setting for entertaining, relaxing, or enjoying Florida evenings year-round. Major updates include a brand-new water heater (2026), AC system (2022), and a BRAND NEW ROOF to be installed prior to closing, offering peace of mind for years to come. Other updates throughout include an updated irrigation system, hanging rack storage in the garage, and a smart deadbolt on the front door. Homes in Georgia Cove rarely hit the market, make an appointment to see it today!

Listing is courtesy of: THE WILKINS WAY LLC (407-874-0230)

Listing Agent: William Wygle (407-375-9005)

Remarks: Under contract-accepting backup offers. Lovely 4 Bedroom, 2 Bath, 2-car garage home on a spacious .23 Acre lot in desirable Woodside Village and zoned for sought-after WINTER PARK SCHOOLS! Feel free to BRING YOUR BOAT as you'll have RARE, DEEDED LAKE ACCESS to LAKE PEARL - a LARGE 64-Acre Lake known for its skiing, boating and fishing activities! This ONE-OWNER HOME is smartly designed with a SPLIT-FLOOR PLAN and features an UPDATED KITCHEN and an UPDATED PRIMARY BATH and has a BRAND NEW ROOF coming Soon! Other upgrades include a BRAND NEW ELECTRICAL PANEL BOX, HARDWOOD FLOORS in the Living & Dining Rooms, a WELL for lawn irrigation (Saves tons off your water bill!) and the house has also been RE-PLUMBED. The spacious Foyer welcomes you in and offers an extra-wide closet for storage. To the right you’ll see the main living area/Family Room with its cozy wood-burning Fireplace & Solar Tube and the REMODELED KITCHEN with SILESTONE COUNTERS, SOLID WOOD CABINETRY, an ISLAND BREAKFAST BAR, STAINLESS APPLIANCES, a SOLAR TUBE, as well as NEWER RECESSED LIGHTING set inside a Lovely TRAY CEILING complete with CROWN MOLDING! The Kitchen has a French Door out to the patio, and is not only open to the Family room, but also has a large pass-through opening it up to the Dining Room and Living Room. This living area features TRIPLE-SLIDING GLASS DOORS to the large screen-enclosed patio. The patio overlooks a lush, well-landscaped back yard featuring a wooden TRELLIS and a welcoming bench seat! All four bedrooms are equipped with neutral carpets and ceiling fans. The Primary Bedroom features an ensuite bath with two vanity areas and is UPDATED with lovely SHAKER-STYLE CABINETRY, CORIAN COUNTERS & a WALK-IN CLOSET. This house has solid Block & Stucco Construction with wood and stone trim and is MOVE-IN READY. The Garage is a spacious 22 x 21 ft & houses the Washer/Dryer which are included as well! Located on a picturesque TREE-LINED street, this unique neighborhood has all the AMENITIES you could want...BOAT RAMP, SKI LAKE, COMMUNITY POOL/TENNIS CTS/PLAYGROUND! Plus, the community has ways to connect that are RARELY FOUND ANYMORE such as ...Women's club, Garden club, holiday socials, book clubs, etc. Zoned for HIGHLY-RATED WINTER PARK SCHOOLS! Only 5 minutes to Trinity Prep & the 417, 10 minutes to UCF, Research Park, Westinghouse/Siemens, Full Sail & Valencia College; 15 MIN. TO DOWNTOWN ORLANDO, the Orlando International Airport, and Downtown Winter Park! Priced so you can make other updates to suit your own taste buds...call for your private showing to make this Lovely home your own!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Diane Sterling (407-761-0512)

Remarks: Don't miss this beautiful UPDATED 3-bedroom, 2-bath home! Enjoy an approximately $80 to $100 a month savings on your electric bill with the installed solar panels! Whole house renovation including NEW Kitchen and Baths, NEW Paint, New Flooring and... All Major updates have already been taken care of: NEW Plumbing (2026), NEW Roof (2021), NEW Solar (2023), NEW AC (2019), NEW Water Heater (2019), NEW Sprinkler System (2023), New Septic Drainfield (2023) and a NEW Fence(2024). Out back, the patio is surrounded by mature landscaping, including bottlebrush trees that regularly attract birds, butterflies, and hummingbirds. It’s a quiet, easy space to enjoy. The neighborhood features sidewalks throughout and access to a nearby park and lake. Zoned for Winter Park High School. Optional bonus: the current owners have established laying chickens and are open to leaving them for the next owner. Move-in ready, well located, and easy to maintain. Solar panels installed in 2023 with all warranties transferrable to new owner. Current solar contract will transfer to the new owner. Many homes in the neighborhood have followed suit due to energy cost savings.

Listing is courtesy of: PERFECT FIT PROPERTIES (407-310-3878)

Listing Agent: Christy Fauquher (407-310-3878)

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: Under contract-accepting backup offers. Welcome to 4408 Lipton Ct. a beautifully updated single-story home in Orlando’s desirable Watermill community, offering the perfect blend of modern upgrades, functional design, and an unbeatable location. This spacious 4-bedroom, 2-bath residence features UPDATED PLUMBING (2021) and REMODELED BATHROOMS (2021), giving you peace of mind and stylish, move-in-ready comfort. Inside, you’ll love the clean, cohesive feel of WOOD LAMINATE FLOORING throughout, complemented by tile in the kitchen and baths for durability and easy maintenance.The OPEN CONCEPT LIVING & DINING area is enhanced by a VAULTED CEILING, creating a bright and airy atmosphere filled with natural light from large windows and sliding glass doors. The SPLIT BEDROOM FLOOR PLAN provides privacy and flexibility for families, guests, or a home office setup. Situated on a generous .28 ACRE LOT, this property offers ample outdoor space to relax, entertain, or play. A standout feature is the serene WATER VIEW in your backyard, perfect for enjoying peaceful mornings or unwinding at the end of the day. Additional highlights include a VOLUNTARY HOA, giving you added flexibility without sacrificing community benefits. Located in established East Orlando, you’re just minutes from UCF, Valencia College, Waterford Lakes Town Center, parks, shopping, dining, and major roadways, including SR 417 and University Blvd for easy commuting. Plus, the home is zoned for A-RATED WINTER PARK HIGH SCHOOL. Whether you’re a first-time buyer or an investor seeking a prime rental opportunity, this home checks all the boxes. Don’t miss your chance schedule your private tour of Lipton Ct today!

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

Listing Agent: Frank Delesline, Iii (407-480-0157)