Maitland Real Estate

Maitland Real Estate

Welcome to Maitland, Florida – a hidden gem nestled in the heart of Central Florida! Known for its picturesque lakes and lush greenery, Maitland is a charming city that beautifully combines suburban tranquility with urban convenience. Just a stone’s throw away from the bustling city of Orlando, Maitland offers a serene escape while keeping you connected to the vibrant culture and entertainment of the larger metropolitan area.

Maitland is rich in history, with its roots dating back to the late 1800s. The city boasts a delightful blend of historic architecture and modern amenities. Stroll through the quaint streets of the historic district, where you’ll find beautifully restored homes and delightful local shops. The enchanting Lake Lily Park is a favorite among residents, offering scenic walking paths, picnic areas, and the perfect spot to unwind amid nature.

Art enthusiasts will appreciate the Maitland Art Center, a unique cultural hub that showcases local talent and hosts various community events throughout the year. The city is also home to several excellent schools, making it an ideal place for families seeking a nurturing environment.

For those who enjoy outdoor activities, Maitland offers plenty of recreational opportunities, from boating and fishing on the sparkling lakes to biking along scenic trails. With its friendly community, diverse dining options, and convenient access to shopping and entertainment, Maitland truly embodies the best of Florida living. Whether you’re looking to settle down or invest in a vacation home, Maitland is a place where you can create lasting memories and enjoy a vibrant lifestyle. Come discover the charm of Maitland today!

Newest Listings in Maitland

$590,000
3 Beds ⋅ 2 Baths ⋅ O6431877 MLS
LOCATION! LOCATION! LOCATION! Set on a beautiful street lined with multi-million dollar homes and beautifully landscaped yards, this 1,785-square-foot, 3-bedroom, 2-bathroom single-story home offers comfortable, practical living with no HOA. The location puts the best of the area right at your doorstep. You are within short walking distance to Homer Hough Park on Lake Sybelia where you have access for kayaking or paddle boarding! A quick 3-minute drive (less than a mile) brings you to Lake Lily Park, the Maitland Community Center, and the Maitland Public Library. You are also just minutes from the new Maitland downtown shops, the Maitland Art Center, the local Farmers Market, top-rated schools, Winter Park dining, and I-4. Inside, walking through the double entry doors brings you into a bright foyer with a direct view straight into the backyard through a wall of windows. The open layout features fresh paint and newer energy-efficient windows, with easy-to-maintain laminate flooring throughout the main living areas and bedrooms, and tile in the kitchen and bathrooms. The central kitchen features granite countertops, a breakfast bar, and stainless steel appliances, including a new refrigerator and dishwasher. Right off the 2-car garage and kitchen, a large indoor laundry room acts as a functional mudroom with a utility sink and space for added storage. The primary bedroom includes a walk-in closet and an ensuite bath, while two guest bedrooms share a full hall bathroom. Out front, a circular driveway provides convenient extra parking. In the back, new sliding glass doors lead to a spacious, fully fenced yard with plenty of room for a pool, garden, or patio. Key mechanical updates include a 2021 roof, updated plumbing and electrical, and a recently serviced dual AC system.

1231 N Lake Sybelia Drive, Maitland
$189,900
2 Beds ⋅ 2 Baths ⋅ O6422482 MLS ⋅ 75 BLDG.
Look at that Price! You decide to move in Now and upgrade as you go, benefitting from this below market price point, or Fix it up as little or as much as you want and keep the added Equity. 2 Bedoom, 1.5 Bath Townhouse with Living and Dining Rooms, Single Car Garage, Inside Laundry Room, and Oversized Fenced Patio. Located between 17-92 & I-4 with short commute to Winter Park, Downtown Orlando, or Maitland Center. Community Features include Swimming Pool less than 50 yards from Unit as well as Dock on Lake in Community. All Appliances in Unit. All Electrical Panels replaced July 2026, Alumicons to satisfy insurance for aluminum wiring added July 2026, Air Conditioning Replaced in 2016, Hot Water Heater in 2018, Garage Door in 2021. Sold As Is, Priced based on current condition.

895 Park Lake Circle Unit 75, Maitland
$219,900
2 Beds ⋅ 2 Baths ⋅ O6431908 MLS ⋅ 6 BLDG.
Impressive - 2 bedroom 2 bath condo on first floor in resort style community of Visconti Maitland. This recently remodeled unit features designer paint throughout, berber carpet, new ceramic tile, a gourmet kitchen with contemporary light grey cabinets, stainless steel appliances and laundry room with w/d hook ups. Community offers its residents 2 tropical pools overlooking Lake Shadow, a fitness center, tennis - and basket ball court and car wash area. Located within minutes to major shopping, entertainment and I-4.

1475 Lake Shadow Circle Unit 6105, Maitland
$239,000
2 Beds ⋅ 2 Baths ⋅ O6431998 MLS ⋅ 5 BLDG.
Virtually Staged. Rare updated 2/2 | | Top-Rated Schools Welcome to peaceful Park Lake Villas! This fully updated single-story condo has spacious living, major energy-efficient upgrades, and an unbeatable location zoned for Dommerich Elementary, Maitland Middle, and Edgewater High. Key Features Brand New A/C (2025) & Updated R-38 Insulation Low-E Thermal Pane Windows & Slider Door replaced throughout Remodeled Kitchen with updated cabinets, appliances, paint, and a cozy dinette space Fully Remodeled Bathrooms (2024) including a private primary en-suite Private Outdoor Space: Second bedroom opens via slider to a fenced yard & patio Convenience: Indoor laundry room with washer/dryer included, pull-down attic storage, and designated parking right out front. Community & Location: Enjoy a tranquil, well-maintained neighborhood with a community pool just steps away. Walk or bike to Lake Lily Park & Farmers Market, Downtown Maitland, Enzian Theater, and local dining. Minutes to SunRail, I-4, Winter Park Village, and Park Ave!

1711 Grove Street Unit 519, Maitland
$179,990
2 Beds ⋅ 2 Baths ⋅ O6431005 MLS ⋅ N/A BLDG.
Don't miss this fantastic opportunity to own this cozy 2 bedroom 1.5 bath condo in the heart of Maitland. The owner's suite is well equipped with a walk-in closet and ensuite. This unit includes all appliances, spacious living room, covered front porch, screened-in back porch overlooking the courtyard, and 2 reserved parking spaces right in front. Additional guest parking is also available. This quiet, small, and well- maintained community is surrounded with mature trees and pathways. Association fees cover community pool, water, sewer, trash, exterior maintenance, and ground maintenance making for worry-free living. Very convenient and close to shopping, dining, and major roadways. Whether you’re a first-time buyer, downsizing, or looking for an investment, this condo is a great opportunity to own in the desirable Maitland area.

336 Cherrywood Gardens Drive Unit 336, Maitland
$810,000
4 Beds ⋅ 2 Baths ⋅ O6430241 MLS
1 year Home Warranty included. Discover Maitland Grove, a well-maintained enclave within one of Central Florida's most sought-after communities. Set in the heart of historic Maitland, celebrated for its scenic beauty and small-town charm, residents enjoy a relaxed suburban lifestyle just minutes from the urban energy, dining, entertainment, and employment centers of Downtown Orlando. Welcome to 231 White Oak Circle, a meticulously maintained 4-bedroom, 2-bath home filled with thoughtful upgrades, distinctive architectural details, and exceptional spaces for both everyday living and entertaining. This is not a cookie-cutter home; it is a property with a story, a sense of place, and details that reveal themselves from room to room. The spacious floor plan offers three separate gathering areas, including a formal living room, an inviting family room, and an oversized great room featuring a bar and access to the expansive screened patio. Natural light pours into the home through two skylights in the family room and an additional skylight in the private primary suite. Travertine flooring and genuine mahogany hardwood create warmth and character throughout. The kitchen is designed for convenience with soft-close cabinetry, two Lazy Susans, and a pot filler positioned above the range. Under-cabinet lighting adds an elegant, inviting ambiance while providing practical task lighting for cooking and meal preparation. Crown molding enhances the dining room, family room, foyer, primary bedroom, and great room, while chair rail detailing adds timeless character to the foyer, entryway, and dining room. A dedicated mudroom provides additional functionality and organization. The split-bedroom layout places the primary suite on the opposite side of the home for added privacy. A pocket door at the entrance to the secondary-bedroom wing provides additional separation and privacy for the home's three secondary bedrooms, while another pocket door at the secondary bathroom maximizes usable space and enhances functionality. The primary suite features an expansive walk-in closet, an additional closet with mirrored sliding doors, and a skylight that fills the space with abundant natural light. The spacious primary bathroom offers two separate showers, including one with a bathtub, dual sinks with granite countertops, and a dedicated makeup and dressing area with a desk. The secondary bathroom also features granite countertops and dual sinks for added convenience. Outdoor living is equally impressive, with porches surrounding the home, beautiful gardens, mature landscaping, established shade trees, rose bushes, privacy fencing, and an expansive screened patio ideal for relaxing or entertaining. An extensive French drain system provides enhanced drainage throughout the property, while four exterior faucets with hose connections are conveniently positioned around the home for easy landscape maintenance. Additional improvements include whole-house re-piping, updated ductwork, and an oversized garage with built-in shelving and a newly finished epoxy floor. A generator and air compressor are also included with the sale, providing added value and convenience. Rich in character, storage, and carefully considered upgrades, this exceptional home offers space, comfort, and timeless appeal inside and out.

231 White Oak Circle, Maitland
$315,000
2 Beds ⋅ 2 Baths ⋅ O6431089 MLS ⋅ Gladstone BLDG.
Completely renovated and move-in ready, a desired first-floor unit in the sought-after Lake Maitland Terrace! This impeccably updated two-bedroom, 1.5-bath condominium blends modern style with an unbeatable lakeside location in the heart of the Maitland/Winter Park area. Thoughtfully redesigned throughout, the home showcases a new kitchen with fresh cabinetry, granite countertops and stainless steel appliances. The baths have been tastefully reimagined with contemporary finishes, and stylish updates continue across the entire unit, delivering a turnkey home you can move into with confidence. The comfortable two-bedroom layout features a full bath in the hall plus a convenient half bath tucked within one of the bedrooms. Sunlight pours through large windows, and the easy first-floor accessibility makes everyday living a breeze. A space-saving washer/dryer combo is conveniently inside the unit, and a dedicated parking space adds day-to-day ease. Set within Lake Maitland Terrace, residents enjoy an amenity-rich community on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Take in the sparkling community pool with beautiful lake views, gather at the clubhouse with a full kitchen, and enjoy lake access from the private dock and fishing pier, plus kayak racks and tree-lined sidewalks throughout. Ideally just minutes from the charming shops, restaurants, and entertainment of downtown Maitland and Winter Park, you can walk to Lake Lily Park's popular events and the Enzian Theater, and reach Winter Park Village and Park Avenue in no time. Zoned for top-rated schools Dommerich Elementary, Maitland Middle and Winter Park High, this beautifully updated home is ready to impress. Whether you're seeking a primary residence or a seasonal retreat, don't miss your chance to claim this exceptional lakeside gem as your own.

1140 S Orlando Avenue Unit G-3, Maitland
$225,000
2 Beds ⋅ 2 Baths ⋅ O6431194 MLS ⋅ 820 Unit 11 BLDG.
Welcome to 820 Park Lake Circle, a beautifully updated two-bedroom condo tucked into one of Maitland’s most convenient locations. Offering the charm and space of a townhouse with the ease of condominium living, this inviting home is just minutes from Downtown Maitland, Park Avenue, Winter Park Village, Lake Lily, major healthcare campuses, I-4, and some of Central Florida’s best shopping and dining. Inside, the home feels fresh, comfortable, and move-in ready. Newer energy-efficient windows and sliding glass doors fill the interior with natural light, while updated flooring creates a clean, cohesive look throughout. The renovated kitchen features quartz countertops, stainless steel appliances, updated cabinetry, and a functional layout that makes everyday cooking and entertaining easy. A convenient half bath completes the main level. Step outside to a spacious, fenced courtyard offering a rare amount of private outdoor living space. Create a comfortable lounge area, grilling station, container garden, or a secure place for pets to enjoy the outdoors. The partially covered area provides additional flexibility for parking, storage, or an expanded patio. Upstairs, two remarkably spacious bedrooms provide room for king-sized furniture, home office space, or a comfortable guest retreat. Each bedroom offers generous closet storage and direct access to the shared Jack-and-Jill bathroom. An additional upstairs closet adds even more practical storage. Just beyond the front door, residents can enjoy the community pool, expansive green space, and the peaceful surroundings of Park Lake. Whether spending a sunny afternoon by the pool, taking a morning walk, or simply unwinding outdoors, the community offers welcome opportunities to relax and enjoy the Florida lifestyle. With an updated interior, private outdoor space, oversized bedrooms, newer A/C, community pool, and an exceptional Maitland location, Unit 11 offers a compelling combination of comfort, convenience, and value.

820 Park Lake Circle Unit 11, Maitland
$235,000
4 Beds ⋅ 2 Baths ⋅ O6430851 MLS
LOOK LOOK LOOK THE OPPORTUNITY WE HAVE BEEN WAITING ON!! YES ITS HERE!4-bedroom, 1.5-bath concrete block home featuring a one-story layout and 1,635 square feet of living space. The home offers a living room, family room, indoor laundry room, and ceramic tile flooring throughout. Whether you're an investor or a buyer looking to renovate and add your personal touch, this property offers great potential. Conveniently located close to I-4, Downtown Orlando, shopping, dining, museums, schools, and other local attractions. Don't miss this opportunity to bring your vision to life! I must call now!

18 Eaton Street, Maitland
$219,900
2 Beds ⋅ 2 Baths ⋅ O6430784 MLS ⋅ 2 BLDG.
Exceptional - 2 bed 2 bath condo on 1st floor in resort style community of Visconti. Featuring designer paint throughout, plush carpeting, a gourmet kitchen with newer appliances, laundry room with full size washer/dryer hook ups and screened in patio with outside storage. Community offers its residents 2 tropical pools overlooking Lake Shadow, Gym, Tennis - and basketball court, play ground and clubhouse. Located within minutes to major shopping, entertainment and Interstate 4. Call and schedule your private showing today !

1100 Lake Shadow Circle Unit 2103, Maitland
$585,000
4 Beds ⋅ 2 Baths ⋅ S5154880 MLS
Virtually Staged. Welcome to 1241 Manchester Road, a beautifully renovated home nestled in the heart of English Estates, one of Maitland's most sought-after and established neighborhoods. This exceptional 4-bedroom, 2-bath residence seamlessly blends timeless charm with modern updates, offering the perfect balance of comfort, style, and functionality. From the moment you step inside, you'll appreciate the bright open-concept floor plan, thoughtfully designed to maximize natural light and create an effortless flow between the living, dining, and kitchen areas—perfect for both everyday living and entertaining. The beautifully updated kitchen serves as the heart of the home, complemented by tastefully renovated bathrooms and a versatile flex room that can easily function as a home office, fitness room, playroom, or media space. Step outside to enjoy the lanai overlooking a backyard, offering endless possibilities for weekend gatherings, outdoor entertaining, or simply relaxing in the privacy of your own backyard. Perfectly positioned in a quiet, tree-lined neighborhood, this home offers the ideal combination of tranquility and convenience. Just minutes from Winter Park, Downtown Maitland, and Downtown Orlando, you'll enjoy quick access to I-4, US-17/92, SR-436 (Semoran Boulevard), Howell Branch Road, and SR-434, making commuting throughout Central Florida effortless. Everyday conveniences are just around the corner, including Publix, Trader Joe's, Whole Foods Market, Costco, Target, Winter Park Village, Altamonte Mall, and an impressive selection of local favorites and acclaimed restaurants. Whether you're looking for your forever home or simply want to enjoy one of Central Florida's most desirable locations, 1241 Manchester Road offers an exceptional opportunity to experience the very best of Maitland living. Schedule your private showing today and discover why homes in English Estates are always in high demand.

1241 Manchester Road, Maitland
$394,000
4 Beds ⋅ 2 Baths ⋅ O6422900 MLS
Opportunity awaits in the established English Woods community! This 3-bedroom, 2-bath pool home is full of potential and ready for its next owner to bring it back to life. Originally designed as a 4-bedroom, the home can easily be converted back, offering added flexibility and living space. Featuring a spacious floor plan, private pool, and hot tub, this property is an excellent opportunity for investors, renovators, or buyers looking to customize a home to fit their vision. Roof is 2006, water heater is 2015, and A/C is 2001. Conveniently located near shopping, dining, schools, and major roadways, this is your chance to create your dream home or add a promising investment property to your portfolio. Bring your ideas and unlock the potential this home has to offer! HUD Case #:094-528168 A Property is HUD owned & subject to HUD rules. FHA eligibility-Insured With Escrow. Sold As-Is, no post-contract repairs or credits. Buyer to independently verify square footage and all measurements, condition, and HOA information if any. The buyer is responsible for activating utilities for inspection. Investors must complete inspections prior to bidding.

2467 Fieldingwood Road, Maitland
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