Homes for Sale Near Maitland Middle in Orlando - 7 homes

Remarks: Under contract-accepting backup offers. Charming 3-bedroom, 2-bath split-plan block home in sought-after area of Orange County! This beautifully updated home features new laminate flooring, freshly painted interior, plush new carpet, and modern fixtures throughout. French doors lead to a spacious enclosed lanai perfect for relaxing, entertaining, or enjoying Florida's beautiful weather. Home features an inside laundry room, and an oversized shed that offers plenty of storage. No HOA! Nestled in the top-rated Winter Park school district, and just minutes from parks and shopping, this home is a must-see! Don’t miss out—schedule your tour today!

Listing is courtesy of: ATKINS REALTY GROUP (407-406-1909)

Listing Agent: Larry Atkins (407-443-9812)

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: 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: Nestled behind Lake Georgia in a quiet, sidewalk-lined neighborhood, this updated 3-bedroom, 2-bath home offers both convenience and calm. Just minutes from the 417 with a straight shot to UCF, the location makes getting around easy while still feeling tucked away. Inside, you’ll find a bright, open layout with luxury vinyl plank flooring throughout the main living areas. The primary suite includes a fully updated en-suite bath with a modern walk-in shower. Major updates have already been taken care of: roof (2021), AC (2019), water heater (2019), sprinkler system (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.

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

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

Remarks: This home is tucked away on a quiet, tree-lined street. Step inside and you’ll love the house flow — ideal for hosting friends, working from home, or just relaxing with your favorite book by the pool side, the wood-burning fireplace or the extra large back porch. The kitchen is a total win with granite counter tops, sleek stainless appliances, tons of cabinet space, with a pantry to keep everything organized. The primary suite is spacious and the bathroom features a walk-in shower and dual sink vanity. This house includes a recent roof (2018), new hot water heater (2021), energy efficient double paned windows and sliding glass doors with blinds built inside the two panes of glass. A new driveway was put in (2023). The garage includes an extended work shop area. Inside laundry room has a sink and cabinets for extra storage.The back yard is fully fenced with a large swimming pool which is 37’ long by 15’ at it’s widest point! Location? You’re close to everything: UCF, Trinity Prep and The Masters Academy This home is zoned for highly rated Winter Park schools. Plus, you’ll have easy access to 417, Oviedo, Winter Springs, and all the best of Winter Park. Whether you're hosting a backyard BBQ or exploring the local scene, this home checks all the boxes for modern Florida living. Don’t miss your chance — come see it today and fall in love!

Listing is courtesy of: HOME SOLD REALTY LLC (833-700-2782)

Listing Agent: Camilo Perez (833-700-2782)

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)

Remarks: BEAUTIFUL Single Story 3 Bedroom, 2 Bath, Split Floorplan Spa Home. Located in the quiet highly sought after community of Lost Lake Village. This Wonderful open floorplan home has been perfectly maintained by the owners. NEWLY installed 2026 AC SYSTEM. Remodeled Kitchen , along with a separate eat-in Nook area, features solid wood cabinets with granite counter tops and stainless appliances. Awesome natural stone fireplace in Family room. Outstanding enclosed huge screened back Patio features a built-in Spa with amazing decking. Incredible larger nicely landscaped fenced in home site. Plenty of room for family fun. Lost Lake Village is a very family and pet friendly community. It is located near everything. Major roadways, shopping and restaurants and top rated schools. This is a must see home!

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

Listing Agent: James Mccarthy (407-622-2122)