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$675,000
3 Beds ⋅ 2 Baths ⋅ Dixie Terrace SubDv. ⋅ 32751 Zip Code
Welcome to 1655 Sunnyside Drive, a beautifully charming home nestled on a picturesque corner lot in the heart of Maitland. Set on classic brick-lined roads, this 3-bedroom, 2-bathroom residence offers 1,418 square feet of thoughtfully designed living space filled with character and warmth. From the moment you arrive, you'll notice the inviting curb appeal, mature landscaping, and the undeniable charm that sets this home apart from the rest. Inside, the home exudes personality with unique architectural touches, cozy living spaces, and abundant natural light throughout. The well-appointed kitchen flows effortlessly into the main living area, making it perfect for both relaxing and entertaining. Each bedroom is spacious and comfortable, while the bathrooms offer tasteful finishes. Whether you're sipping coffee on the front porch or enjoying the peaceful surroundings, you'll feel right at home in this special space. Situated just minutes from the vibrant shops and restaurants of Park Avenue, this home also features two separate driveways, offering plenty of parking for guests or multiple vehicles—a rare find in this area. With its unbeatable location, timeless charm, and practical layout, 1655 Sunnyside Drive is the perfect blend of convenience and character. Don’t miss your opportunity to own a true gem in one of Maitland’s most desirable neighborhoods. ROOF: 2021 PLUMBING: 2021 AC: 2021 ELECTRICAL: 2021

1655 Sunnyside Drive, Maitland
$539,900
3 Beds ⋅ 2 Baths ⋅ Roosevelt Place SubDv. ⋅ 32751 Zip Code
This charming home boasts a wealth of valuable upgrades and improvements, making it an enticing opportunity for anyone seeking a move-in ready property The roof was replaced in 2024, ensuring long-lasting durability. A significant renovation in 2024 Both Bathrooms FULLY REMODELED, New AC inside and outside, all new baseboards too much to list. Extra Large kitchen, including all kitchen appliances and luxurious vinyl plank flooring, with extra flooring thoughtfully left in the house for future use. Two electric fireplaces provide cozy ambiance, and a fully functional wood fireplace offers additional charm and warmth if the buyer wishes to restore it. The property also received a host of exterior enhancements in 2017 and 2018, including a paver patio, fence, and a newly installed drain field for the septic system. The well pump was replaced around the same time Refurbished water treatment system. A relatively new Kinetico Premier water system, though exact installation date eludes memory, comes with operational paperwork for easy use. Further updates in 2020 include new windows in the garage and three bedrooms, a generator switch box, and new electrical panels. The attic received fresh insulation, and the ducts were professionally cleaned, ensuring energy efficiency. To top it all off, a brand-new shed was added in 2022, providing ample storage space for your convenience. This meticulously maintained property is a true gem, offering both modern amenities and peace of mind for years to come. Don't miss the chance to make it your own!

135 Roosevelt Place, Maitland
$600,000
Hollieanna Shores SubDv. ⋅ 32751 Zip Code
Perfect opportunity to make this your dream home or add to your investment portfolio. This home is located on a 8x100 lot in the heart of Maitland and is walking to distance to Dommerich Elementary and Maitland Middle schools. This property provides loads of potential and offers a fenced backyard and a 2-car garage. Set up your showing today.

107 Tangelo Court, Maitland
$600,000
3 Beds ⋅ 3 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code
Perfect opportunity to make this your dream home or add to your investment portfolio. This home is located on an 80x100 lot in the heart of Maitland and is walking to distance to Dommerich Elementary and Maitland Middle schools. This property provides loads of potential and offers a fenced backyard and a 2-car garage. Set up your showing today.

107 Tangelo Court, Maitland
$575,000
4 Beds ⋅ 2 Baths ⋅ Forest Brook 3rd Sec SubDv. ⋅ 32751 Zip Code
Experience refined living in this impeccably maintained 4Bd/2Ba pool home with a spacious layout, perfectly situated in a desirable, well-established neighborhood close to shopping, dining and everyday essentials. The customized kitchen is a true showpiece—featuring an expansive pull-out pantry, double pull-out corner cabinet system, built-in spice rack, and a spacious island designed for both function and elegance. Abundant natural light, updated flush mount lighting, and ample storage create a space that is as beautiful as it is practical. Throughout the home, you’ll find timeless finishes including crown molding, wood-look porcelain tile, and double-pane windows that enhance both style and comfort. Step outside to your private oasis—an extra-large refinished pool (2017) surrounded by premier artificial turf and lush landscaping offering the perfect balance of luxury and low maintenance. The oversized garage impresses with extra shelving, an insulated door with DC quiet opener and battery backup, and the refrigerator is included. Peace of mind comes with thoughtful updates: Roof (2021), HVAC (2016), and new ductwork, R30 insulation and aluminum soffits (2024). A home where craftsmanship meets comfort—modern sophistication and meticulous care make this a rare opportunity not to be missed. CALL TODAY to schedule your private viewing.

671 Brookside Road, Maitland
$571,430
3 Beds ⋅ 2 Baths ⋅ Indian Hills Unit 9 SubDv. ⋅ 32751 Zip Code
RENOVATIONS OF THE HIGHEST STANDARD!! Sunshine State Home’s experienced design team continues to exceed the expectations of today’s discerning Buyer’s. The renovation of this classic Mid-Century Maitland home brings delightful charm within a highly sought after NON-HOA neighborhood of Indian Hills. The finished product “punches above it’s weight” in every possible way. KITCHEN offers two-tone, solid wood cabinetry topped with contemporary quartz counters. Stylish finishes including an undermount sink with long-neck faucet, upgraded black-matte cabinet door pulls and a modern stainless steel appliance package create a delightful cooking environment. LARGE LIVING SPACES including living / bonus / dinette and separate family rooms offer an abundance of options catering to a variety of lifestyle preferences and activities. BEDROOMS within this split-plan layout include His/Hers closets in the primary suite and a large 2nd bedroom and 3rd bedroom situated privately in the far corner of home. FLOORING throughout the home, upgraded Luxury Vinyl Plank was laid “wall-to-wall” and topped with upgraded 5 ¼“ baseboards, creating a peaceful yet contemporary feel to every room. BATHROOMS (both primary and secondary) have been fully remodeled including sinks, faucets, shower, tub, toilets, lighting and more. FINISHES including modern door hardware & hinges, ceiling fan and LED lighting throughout, wire rack shelving in all closets, updated electrical outlets and switches all combine to bring this vintage home up to today’s look & feel. OUTSIDE, a covered area on the back patio lanai provides the perfect shaded gathering place amidst a sun-filled day splashing in the inground swimming pool. Fully fenced and private, the backyard offers an oasis for sunbathing and a midnight swim. 4-POINT inspection items including roof (2023), hot-water heater (2025), HVAC (2019) will provide peace of mind. COMMUNITY events and activities abound within Indian Hills. Kewannee Park, a county park, offers walking trails and a boardwalk, fishing ponds, basketball court, and playgrounds all within walking distance. A-Rated Seminole County Public School district.

2666 Derbyshire Road, Maitland
$779,500
3 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code
Welcome to this charming, move-in ready home nestled in the desirable, family-friendly Dommerich neighborhood. Featuring 3 bedrooms, 2 full bathrooms, and an open-concept living area filled with natural light, this home has the perfect blend of comfort and style. Featuring 2 additional dedicated office rooms, ideal for remote work or creative space, this home is ideal for modern living. The updated kitchen boasts stainless steel appliances, marble countertops, and ample cabinet space. Step into an open, light-filled interior with brand new flooring throughout and breathtaking floor-to-ceiling windows that has panoramic views of the sparkling saltwater pool. In the cooler months enjoy your own wood burning fireplace. Outside, enjoy a spacious paver driveway, a large 2-car garage, and a private backyard oasis. Major upgrades include a brand new roof (2025), ensuring peace of mind for years to come. Additional upgrades include recessed lighting, new flooring throughout, marble bathroom tiling, energy-efficient windows, new paver driveway and fresh interior/exterior paint. Enjoy private boat ramp access to the Winter Park Chain of Lakes. Zoned for A-rated Dommerich Elementary, Maitland Middle School and Winter Park High School. Walking distance to the Maitland Community Park, Maitland Social and the Maitland City Center. Minutes from Winter Park’s Park Avenue, known for its exquisite shopping and dining. Don’t miss out on this opportunity!

421 Arapaho Trail, Maitland
$500,000
4 Beds ⋅ 2 Baths ⋅ Indian Hills Unit 1 Rep SubDv. ⋅ 32751 Zip Code
**2025 ROOF** | **POOL HOME** Start your new life to one of Orlando's most prestigious suburbs! Located in the heart of Maitland and zoned for great schools! This 4 bedroom, 2 bath home is a sanctuary for a growing family or to start yours. In this stunning home comfort meets timeless charm. Outside you will find a Zen-like screened pool area and a serene back yard lushly landscaped with mature fruit trees. Enjoy the benefits of a newly installed roof and upgraded insulation, providing energy efficiency and cost savings. This home offers the perfect blend of value and comfort, situated minutes from downtown Winter Park, downtown Orlando and just walking distance from Kewanee Park. Here you’ll enjoy proximity to upscale boutiques, cafés and fine dining, making this home convenient and comfortable for everyday living. This is a rare opportunity to own a meticulously maintained and perfectly situated home. Ready for you to move in and enjoy!

2632 Derbyshire Road, Maitland
$680,000
3 Beds ⋅ 4 Baths ⋅ Orangedale Park SubDv. ⋅ 32751 Zip Code
HUGE Price Reduction!! There is simply nothing that compares to this deal! This exquisite attached single family home blends contemporary elegance with unbeatable convenience in a truly coveted Maitland address. Just a stroll from Maitland Preparatory School and mere minutes from the vibrant heart of Downtown Winter Park, this residence offers the best of both worlds. From the moment you arrive, you’ll sense the refined lifestyle within. soaring ceilings, abundant natural light, and premium finishes throughout. The chef’s kitchen is a showpiece sleek cabinetry, stone countertops, and top-tier appliances. Entertain effortlessly with open living spaces that flow seamlessly to relaxing patios or balconies. With 3 bedrooms and 3½ baths, each space is a sanctuary. The primary suite impresses with its spa-style bath and custom closets. Upstairs, the laundry is tucked neatly beside the bedrooms for ease and efficiency. Thoughtfully designed storage niches and built-ins complete the picture. The real magic is the location. You’re only 5 minutes from Winter Park’s world-class dining, boutique shops, cultural venues, riverside parks, and Sunday farmer’s market. Stroll through cobbled streets, enjoy al fresco cafés, or catch live music on Park Avenue this home gives you that full lifestyle. Live luxuriously in a community where neighbors share the same roof and an unspoken sense of sophistication reigns. While it feels like condominium living, this is fee simple ownership in a four-unit enclave with NO HOA fees. You get the benefits without the burden. This is more than just a home it’s a statement. Don’t miss your opportunity to own a residence that’s as beautiful as it is brilliantly located.

183 Orange Place, Maitland
$970,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code
Sold data entry only

2031 Chippewa Trail, Maitland
$350,000
3 Beds ⋅ 2 Baths ⋅ English Ests Unit 1 SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Nestled in the sought-after English Estates neighborhood, this classic Medallion home offers timeless character and the perfect opportunity to make it your own. Featuring its original Medallion hallmark in the kitchen pantry, this retro gem includes formal living and dining rooms, a cozy breakfast nook off the galley-style kitchen, and original terrazzo flooring. Recent updates include a reroof and exterior paint (2021), fresh interior paint (2025), hot water tank (2021) and an upgraded A/C system with UV light (2019). Your new home was replumbed in 2015 and the electrical updated in 2012. The interior laundry room adds convenience, while the spacious enclosed and screened porch provides a peaceful retreat to relax and enjoy the evening sunset. Don't miss the chance to bring your vision to this well-maintained mid-century treasure.

2065 Derbyshire Road, Maitland
$365,000
3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code
Welcome to Montacino, a gated community offering both convenience and charm. This updated 3-bedroom, 2.5-bath townhome combines modern finishes with a comfortable, functional layout. The first floor features an open design with spacious living, dining, and kitchen areas that flow seamlessly for everyday living or entertaining. The kitchen includes granite countertops, stainless steel appliances, and a stylish backsplash, with views of the covered back porch overlooking a peaceful green space. A convenient half bath is also located downstairs. Upstairs, the primary suite offers a private balcony, walk-in closet, and en-suite bath with dual vanities and a walk-in shower. Two additional bedrooms, a full bathroom, and a conveniently located laundry closet with washer and dryer complete the second level. Recent updates include new laminate flooring downstairs, along with a new microwave and refrigerator. The home also includes a one-car garage. Residents enjoy truly maintenance-free living, with the HOA fee covering internet, cable TV, exterior pest/termite control, roof repair and/or replacement, and exterior upkeep, as well as access to a resort-style pool, beautifully landscaped grounds, and lakeside sidewalks perfect for a stroll. A transferable home warranty is also available for added peace of mind. Ideally located near I-4, Winter Park, and Downtown Orlando, this home offers the perfect balance of a peaceful retreat and city convenience.

1291 Blessing Street, Maitland
$635,000
Dixie Terrace SubDv. ⋅ 32751 Zip Code
Tucked away on a quiet dead-end street, this rare double lot is framed by a stately mature oak tree, setting the tone for the estate you’ve always envisioned. Positioned right on the border of Maitland and Winter Park, the location offers the best of both worlds, minutes from Park Avenue’s dining and boutiques, lake days on Lake Maitland, and seamless connectivity to I-4. Surrounded by top-rated schools and established luxury homes, this property offers limitless potential to design and build with the builder of your choice. More than just land, this is an opportunity to create your own sanctuary in one of Central Florida’s most desired enclaves.

1630 Lyndale Boulevard, Maitland
$375,000
3 Beds ⋅ 3 Baths ⋅ Ultra Vista Condo SubDv. ⋅ 32751 Zip Code
Stunning, renovated condo in Maitland’s Ultra Vista community with attached one-car garage. Expect to be impressed as you enter this luxury residence boasting vaulted ceilings which fill the home with natural light! Fall in love with this remodeled kitchen with a butcher block island, 42-inch white cabinetry, soft-close drawers, pantry, tile flooring, and stainless-steel appliances. Wonderful great room with wood-burning fireplace, dining room, and sliding doors leading to the enclosed outdoor porch, perfect for entertaining! Gorgeous wood flooring brings warmth to the home. Retreat to the primary suite with an impressive, updated bath featuring stone counters, walk-in closet, and spacious walk-in shower. The 2nd bedroom is bright and spacious with an updated en-suite bath with soaking tub. The downstairs bedroom with updated en-suite bath is perfectly positioned for a guest suite, home office or den. Enjoy the privacy outdoors with the stone patio and beautiful landscaping overlooking a conservation area. Updates include a new roof (2024), new electrical panel (2024), replumbed, AC (2016) and new exterior paint coming soon. This private community offers a sparkling swimming pool and dog park for its residence. Incredible location, minutes to Winter Park’s Park Ave for shopping and dining. This is the one you have been waiting for!

1990 Kenaston Road Unit 1990, Maitland
$251,500
2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Live on Lake Maitland, part of the Winter Park Chain of Lakes, for just $250,000! This 2-bedroom, 1.5-bath condo in Lake Maitland Terrace is one of the most desirable units in the community, offering 816 square feet and a prime second-floor corner location with a screened-in front porch. Inside, you’ll find spacious living areas with bamboo flooring, plantation shutters, and abundant natural light. The porch extends your living space and is the perfect spot to quietly sip your morning coffee. Thoughtful upgrades set this home apart. The washer and dryer are conveniently located in the hallway, preserving closet space in both bedrooms. The primary bedroom features a true walk-in closet, and both bedrooms include custom closet systems that maximize storage and style. Opportunities to live on the Winter Park Chain of Lakes at this price point are incredibly rare. With its generous layout, upgraded features, and unbeatable location, this condo is a standout that won’t last long.

1140 S Orlando Avenue Unit F9, Maitland
$285,000
3 Beds ⋅ 2 Baths ⋅ Lake Eulalia Heights SubDv. ⋅ 32751 Zip Code
Tucked away in a tranquil setting, this charming 1958 split-level home offers a peaceful retreat surrounded by lush, thoughtfully landscaped gardens. As you arrive, you’ll feel an immediate sense of calm, greeted by a welcoming stairway and a serene garden path that invites you to explore before you even step inside. The main level features a spacious, light-filled living and dining area—perfect for entertaining or relaxing with loved ones. Large windows frame picturesque views of the gardens, flooding the space with natural light. Beneath the main level carpet, discover the timeless beauty of original terrazzo flooring, just waiting to be uncovered and restored. The lower-level bonus room is designed for both fun and function, complete with custom cabinetry and a sleek granite bar—ideal for hosting game nights or casual gatherings. Whether you’re entertaining or unwinding, this space offers flexibility and comfort. Step outside into your own tropical oasis, where mature landscaping, stone pathways, and private garden nooks create a perfect environment for relaxation and connection with nature. *The info in MLS is thought to be correct but not guaranteed*

721 Lake Avenue, Maitland
$255,000
1 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Step inside this beautifully reimagined Lake Maitland Terrace condo, where every detail has been thoughtfully updated for style and function. Renovated in 2021, this spacious one-bedroom residence embraces a modern design with clean lines, custom finishes, and a touch of industrial character from the exposed ceiling piping. The open layout features a bright great room that flows seamlessly into the kitchen, designed with both cooking and entertaining in mind. Highlights include Caesarstone quartz countertops, a mirrored backsplash, a farmhouse sink, KraftMaid soft-close cabinetry, and an oversized island with seating. Premium appliances such as a KitchenAid convection oven with induction cooktop, Bosch dishwasher, French-door refrigerator, and in-unit washer and dryer add convenience and sophistication. Originally configured as a two-bedroom, the condo has been transformed into a larger one-bedroom retreat but can easily be converted back if desired. The bathroom offers a tub/shower combination and an extra-wide pedestal sink. Enjoy a low-maintenance lifestyle with resort-style amenities, including a community pool, shuffleboard courts, fishing pier, and access to Lake Maitland and the Chain of Lakes. The unbeatable location puts you within walking distance of the Enzian Theater and Lake Lily, while Winter Park Village, Park Avenue, and A-rated schools are just minutes away.

1140 S Orlando Avenue Unit J2, Maitland
$545,000
4 Beds ⋅ 2 Baths ⋅ English Estates Unit 3 SubDv. ⋅ 32751 Zip Code
Seller is willing to assist with buyer closing costs or assist with interest rate buy down. This stunning 4-bedroom, 2-bathroom home has been completely reimagined from the ground up, offering flawless design, and premium finishes. Situated on a generous lot in a sought-after Maitland neighborhood, this home combines comfort, function, and style in every detail. Step inside to an inviting open-concept layout with luxury vinyl plank flooring, new lighting, and abundant natural light streaming through vinyl windows. The designer kitchen steals the spotlight with updates cabinetry, granite countertops with, and new appliances—crafted for the modern entertainer. The primary suite offers a tranquil retreat with a spa-inspired en suite bathroom featuring beautiful tilework and elegant fixtures. Both bathrooms have been tastefully renovated to reflect timeless design. Enjoy the added flexibility of a dedicated laundry room and a 2 car garage offering extra storage and workspace. Outside, the expansive backyard with a newly resurfaced in ground pool is your canvas for creating the outdoor lifestyle you've always wanted—whether it's hosting gatherings, gardening, or relaxing in the Florida sunshine. Located just minutes from top-rated schools, parks, shopping, and dining, 1470 Winston isn’t just move-in ready—it’s transformation perfected. Schedule your private showing today and fall in love with everything this exceptional home has to show. Clean 4 point inspection available by request.

1470 Winston Road, Maitland
$490,000
3 Beds ⋅ 2 Baths ⋅ Oakland Shores SubDv. ⋅ 32751 Zip Code
Beautiful Mid-Century Modern in Maitland! Sylish 3-bed, 2-bath, single-story home with 2-car garage + office on a quiet, tree-lined street. Features include vaulted ceilings, hardwood floors (no carpet), updated kitchen and baths, and a wood-burning fireplace. Enjoy a sunny Florida Room overlooking the fully fenced backyard. Upgrades include NEW energy-efficient windows, built-in closets, smart lighting and cameras, and fresh, modern paint colors. The chef’s kitchen offers stainless appliances, farmhouse sink, and ample cabinetry. Perfect for entertaining—dine al fresco on the large patio under shade trees or gather inside the Florida Room. No HOA. Just minutes from Maitland City Centre, the 414 for easy travel and 10 minutes to Park Avenue. Call today for your private showing.

515 W Faith Terrace, Maitland
$455,000
3 Beds ⋅ 2 Baths ⋅ Greenwood Gardens Sec 01 SubDv. ⋅ 32751 Zip Code
Step into this delightful 3-bedroom, 2-bath split plan home, perfectly nestled in one of Maitland's best-kept secret neighborhoods. As you approach, a spacious front porch welcomes you—the perfect spot to enjoy your morning coffee or an evening unwind. Inside, you'll find a home that's been thoughtfully updated and is ready for its new owners. Freshly painted walls and brand-new bedroom carpets create a clean, inviting canvas. The main living areas feature beautiful saltillo tile, a stylish and durable foundation just waiting for your personal touch. The home's open floor plan is anchored by a kitchen that was remodeled in 2013, complete with a cozy eating area that's ideal for casual meals or gatherings. The spacious living room is the heart of the home, boasting vaulted ceilings, with two skylights, and a charming wood-burning fireplace that adds warmth and character. One of the standout features is the incredible backyard, a true entertainer's paradise. A 500-square-foot patio with a wooden pergola provides a fantastic space for relaxing or hosting get-togethers. The generously sized, fully fenced yard offers plenty of room for outdoor fun and games. Plus, a versatile outdoor shed is ready to be transformed into your dream workshop, a tranquil "he/she shed," or even an outdoor kitchen. This home offers the perfect balance of privacy and convenience. Key updates include a new roof (2022) and a complete repipe (2016), giving you peace of mind. Its prime location puts you just minutes from local favorites like the Enzian theater, Publix, Kappy's Subs, the Sunrail station, and the vibrant dining and shopping scene of Winter Park and Lake Lily. Ready to see this Maitland gem for yourself? Let me know if you'd like to schedule a showing!

741 Robinhood Drive, Maitland
$475,000
4 Beds ⋅ 3 Baths ⋅ Maitland Village SubDv. ⋅ 32751 Zip Code
Charming and Spacious Townhome in Maitland! Welcome to 1938 Michael Tiago a beautifully maintained 4-bedroom, 2.5 bathroom home located in the desirable Maitland Village Community with a POND VIEW and END UNIT. This stunning property offers a perfect blend of classic charm and modern convenience, making it an ideal place to call home. As you approach this inviting residence, you’ll notice the lush landscaping and curb appeal that instantly sets the tone for what’s inside. Step into the spacious living area, where natural light pours in through large windows, creating a warm and inviting atmosphere. The open-concept floor plan seamlessly flows into the dining area and kitchen, making this space perfect for both everyday living and entertaining guests. Crown molding enhances the rooms adding just that right touch! Custom Plantation Shutters adorn all the windows downstairs & upstairs. The kitchen is a chef's dream, featuring stainless steel appliances, granite countertops, and ample cabinet space for all your culinary needs. A walk in panty is another feature of the kitchen. Whether you're preparing a weeknight meal or hosting a dinner party, this kitchen will exceed your expectations. The primary suite is generously sized and offers a peaceful retreat, complete with a private en-suite bathroom featuring a dual vanity, soaking tub, and a separate walk-in shower. Two additional well-appointed bedrooms provide plenty of space for family. The fourth bedroom featuring French Doors is located downsttairs...it can also be used as an office if needed. The Loft upstairs is light & bright and would make a great office or home school area. The Tile Roof brings long lasting peace of mind. This is an End Unit which allows for more light to filter thru from outside. Hot Water Heater is new. New Stainless Steel Dishwasher & Disposal are being installed. HOA fees cover exterior maintenance, 500 Mbps internet, 250 channel cable, water, sewer, trash, lawn care, sprinklers, streetlights, community pool, clubhouse, gate access and management services. Your low HOA fee takes care of all the yard work so you can enjoy the Community Pool. This makes living here "totally carefree living at its best". Other highlights include tile & engineered wood flooring throughout downstairs, a covered porch with a pond view, no neighbor on one side and a 2-car garage that has 2-car EV-ready. Located just minutes from shopping, dining, and major roadways, this home offers the convenience of being close to everything while providing a quiet, serene neighborhood feel. Don't miss your chance to own this charming Maitland home. Schedule a showing today and make 1938 Michael Tioga your new address!

1938 Michael Tiago Court, Maitland
$647,000
3 Beds ⋅ 3 Baths ⋅ Greenwood Gardens Sec 02 Rep 01 SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Step inside this home from anywhere! To experience a fully immersive walk-through of this home click on the Video or Virtual Tour button on this page. Welcome to one of Maitland’s best-kept secrets! Tucked away in a peaceful, no-through street with Maitland Park right across the way, this charming corner-lot home offers the perfect balance of privacy, comfort, and convenience. From your doorstep, you can walk to favorite restaurants, coffee shops, and the Brightline station, while Lake Lily Farmers Market, Downtown Maitland, and vibrant Winter Park are only minutes away. Step inside and you’ll be greeted by a spacious open layout, filled with natural light and designed for easy living. Wood-look tile flows seamlessly throughout, offering both style and low maintenance. The large living room centers around a cozy wood-burning fireplace, creating the perfect gathering spot for family and friends. The kitchen is a true standout with warm wood cabinetry, granite countertops, stainless steel appliances, and a sleek tile backsplash. Just off the kitchen, an enormous bonus room adds incredible flexibility—use it as a second living area, playroom, home gym, theater, or anything your lifestyle requires. The split floor plan ensures privacy for the oversized primary suite, which includes ample space for a sitting area or home office, a huge walk-in closet, and a spa-inspired bath with dual sinks and a glass-enclosed tile shower. Two additional generously sized bedrooms share a full bath with a tub/shower combo, while a third full bath with a walk-in shower provides added convenience for family or guests. Practicality meets comfort with a large indoor laundry room complete with folding space, plus a two-car side-entry garage with an epoxy floor. Sliding doors open to the fenced backyard with a covered patio—ideal for entertaining or enjoying Florida’s sunshine in peace. Recent updates include a new roof (2023), fresh interior paint, and a newer AC system, giving you peace of mind for years to come. All of this is in a prime Maitland location with quick access to I-4, highly rated schools (both public and private), and endless parks, trails, and activities. This home offers the lifestyle you’ve been waiting for—don’t miss the opportunity to make it yours!

955 Gamewell Avenue, Maitland
$915,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code
One-story home in Dommerich Hills within walking distance to Dommerich Elementary and Maitland Middle schools. Move-in ready with wonderful pool. Beautifully landscaped.

2021 Chippewa Trail, Maitland
$335,000
2 Beds ⋅ 2 Baths ⋅ Branch Tree SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Welcome to this beautifully updated Branch Tree duplex, where style meets convenience! Step inside to discover a brand-new kitchen with sleek granite countertops and modern cabinetry, complemented by fresh paint throughout. The primary suite impresses with a fully renovated bathroom featuring a spacious walk-in shower and dual vanity. Luxury vinyl floors flow seamlessly through the open living spaces, highlighted by soaring ceilings that create a bright and airy atmosphere. Enjoy a private backyard for relaxing or entertaining, plus the convenience of a one-car garage. Perfectly situated near shopping, dining, UCF, and charming downtown Winter Park, this home offers both comfort and a prime location. Don’t miss your chance to make this move-in-ready gem yours!

419 Poplar Court, Maitland
$395,000
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code
SELLER PAYING CONCESSIONS OF 6 MONTH HOA FEES. Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the Moorings on Lake Maitland. Enjoy relaxing on the Lake Front Dock or on your own Private Enclosed Patio! Step inside this spacious 2 bedroom 2 bath great room plan, perfect for relaxing or entertaining. The beautifully upgraded kitchen has stainless steel appliances and granite counters and a charming dining nook. The master suite features an updated ensuite bath with dual sinks and a walk in shower with a custom glass enclosure. There is a generous walk in closet with custom built ins. Imagine coffee in the morning with lake views from your living room or your spacious patio. Only 5 minute drive to Winter Park's shops & Sidewalk Dining along the famed Park Avenue. Stroll over to Maitland's lovely Lake Lilly Park for Seasonal Events, Art Festivals, Concerts and local Farmer's Market! Incredible Location & Lifestyle!!!!

204 Quayside Circle Unit 304, Maitland
$178,900
2 Beds ⋅ 2 Baths ⋅ Cherrywood Gardens SubDv. ⋅ 32751 Zip Code
Welcome to Cherrywood Gardens! This charming 2-bedroom, 1.5-bath condominium offers 953 sq. ft. of comfortable living space in the heart of Maitland. Step inside to find an inviting living and dining room combo, a bright kitchen with included appliances, and a primary suite with a walk-in closet. Enjoy your mornings on the front porch or take advantage of the community’s amenities, including a pool & clubhouse. Association fees cover water, sewer, trash, exterior maintenance, and grounds upkeep—making for worry-free living. Located near top-rated schools, shopping, dining, and major roadways, this home provides both comfort and convenience. Whether you’re a first-time buyer, downsizing, or looking for an investment, this condo is a great opportunity to own in a desirable Maitland community.

107 Cherrywood Gardens Drive Unit 8, Maitland
$899,000
4 Beds ⋅ 3 Baths ⋅ Maitland Isle SubDv. ⋅ 32751 Zip Code
This beautifully updated residence, nestled on a desirable corner lot in the tranquil Maitland Isle Subdivision, offers nearly 2,900 square feet of refined living with four bedrooms and two and a half baths. The home enjoys private lake access to Lake Maitland on the Winter Park Chain of Lakes, combining natural beauty with everyday convenience. Designed with a split, open floor plan filled with abundant natural light, it showcases a completely renovated kitchen (2020) featuring a large island with granite countertops, wood cabinetry and stainless steel appliances. Upstairs, the spacious primary suite is a private retreat with its own balcony overlooking the pool and backyard, while the lushly landscaped grounds include mango, avocado and tangerine trees, creating a serene tropical escape. Recent updates elevate this home’s appeal, including new carpet (2025), a pool cleaner (2025), one A/C unit (2025), plantation shutters (2025), dishwasher (2025), new windows (2024), a car charger installation (2024), washing machine (2024) and attic insulation (2022). Additional enhancements include renovated baths, luxury vinyl plank flooring, updated exterior doors, outdoor fencing and energy-efficient solar panels (2018) that provide approximately $250 per month in electricity savings. The roof, pool equipment, and more have also been thoughtfully upgraded for peace of mind. Perfectly positioned within an excellent school district—Lake Sybelia Elementary, Maitland Middle and Winter Park High—this home is close to Maitland City Center, Park Avenue, and local dining, parks and recreation. Combining comfort, modern updates and an exceptional location, this Maitland Isle property is an outstanding opportunity in one of the area’s most sought-after neighborhoods.

121 Mariner Way, Maitland
$240,000
2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Welcome to Lake Maitland Terrace, where lakeside living meets modern style! This beautifully updated first-floor condo offers comfort and convenience in one of Maitland’s most sought-after communities. Inside, you’ll find brand-new upgrades completed in 2025, including fresh flooring, a new water heater, and a new in-unit washer and dryer. The kitchen is a true highlight, featuring stainless steel appliances, quartz countertops, white shaker cabinets, a stylish backsplash, a center island, and a cozy breakfast nook that’s perfect for enjoying your morning coffee. Lake Maitland Terrace is all about lifestyle. Residents enjoy a lakefront pool and sundeck with stunning views of Lake Maitland, a clubhouse with Wi-Fi, a fully stocked kitchen, and a coffee bar. The community also offers a large dock for fishing or simply relaxing, boat slips for rent, kayak and paddleboard racks, shuffleboard, a putting green, and an enclosed bicycle garage. Additional conveniences include designated parking, gas grills by the pool, a car wash area, and on-site laundry facilities. Perfectly located, this condo is just minutes from local favorites like Eden Bar and the Enzian Theater, Luke’s Kitchen and Francesco’s, along with the Shoppes at Maitland and all the dining and boutiques of nearby Park Avenue. With its modern upgrades, resort-style amenities, and unbeatable location, this home is the perfect blend of comfort and Florida lakefront living. Don’t miss your chance to make it yours, schedule your private showing today!

1140 S Orlando Avenue Unit F2, Maitland
$285,000
3 Beds ⋅ 2 Baths ⋅ Hamlet At Maitland SubDv. ⋅ 32751 Zip Code
Welcome to 1073 Hamlet Drive—an updated 3-bedroom, 2-bathroom block home with over 1,000 square feet of comfortable living space, a 1-car garage, and a prime location in the highly sought-after community of Hamlet at Maitland. From the moment you step inside, you'll be greeted by vaulted ceilings, an abundance of natural light, and an open floor plan that’s ideal for entertaining. The spacious living room flows effortlessly to a sliding glass door that leads out to a cozy patio—perfect for summer BBQs and enjoying the Florida sunshine. The kitchen is well-appointed with stainless steel appliances, granite countertops, shaker-style cabinetry, and a dedicated food pantry for extra storage. The large owner’s suite offers a true retreat with its walk-in closet and en-suite bathroom featuring a dual-sink vanity with granite countertops, an oversized, well-lit mirror, and a garden tub with shower—perfect for soaking the day away. The home also includes a full guest bathroom and two additional guest bedrooms, one of which includes a walk-in closet. Situated in a friendly, owner-occupied community with a low HOA fee, Hamlet at Maitland places you near top-rated schools like Dommerich Elementary and Maitland Middle and just minutes from the best dining, shopping, and amenities of both Maitland and Winter Park. Schedule your private showing today—this one won't last!

1073 Hamlet Drive, Maitland
$552,000
4 Beds ⋅ 4 Baths ⋅ Dommerich Hills Fifth Add SubDv. ⋅ 32751 Zip Code
Distinctive Dommerich Hills Home with Flexible Floor Plan and Modern Upgrades. Welcome to this truly unique residence in the highly desirable Dommerich Hills neighborhood, where character, thoughtful updates, and a versatile layout come together to create the ideal setting for modern living. Perfectly situated just minutes from Winter Park and Maitland—and zoned for Dommerich Elementary, Maitland Middle, and Winter Park High—this home combines charm with convenience in one of Central Florida’s most sought-after locations. The spacious two-story design features four bedrooms plus a flexible bonus room, two full bathrooms, and two half baths. The main-level primary suite offers both privacy and comfort, complete with direct access to the backyard retreat. Upstairs, dual staircases provide easy flow to additional bedrooms and extensive hidden storage that spans the length of the home. The bonus room, outfitted with a Murphy bed and an adjacent half bath, is perfect for guests, a home office, or a fifth bedroom option. At the heart of the home, the chef’s kitchen is as functional as it is stylish, boasting gas appliances, butcher block counters with pop-up outlets, spice and oil niches, appliance hideaways, a pet nook, and a convenient pass-through window to the outdoor entertaining space. A butler’s pantry with beer and wine fridge, commercial-grade washer and dryer, and built-in bar elevate both everyday living and entertaining. Recent updates bring peace of mind: new roof (2022), HVAC (2019), windows (2021), garage door, tankless gas water heater, water softener, and new city sewer connection. Gas lines for the dryer, grill, or generator add extra efficiency. Outdoors, enjoy the Florida lifestyle in a private setting with a deck, gazebo, outdoor shower, and pergola-covered seating area. A private well feeds the irrigation system, keeping the landscaping lush year-round, while a cedar façade enhances curb appeal and architectural detail. This is not a cookie-cutter home—it’s a property designed for those who appreciate creativity, comfort, and functionality. With its top-rated schools, prime location, and a floor plan built for today’s needs, this Dommerich Hills treasure is a rare opportunity. Schedule your private showing today—homes like this don’t come along often.

1135 Thunder Trail, Maitland