Maitland Homes with Sidewalk Exterior Features

Maitland Homes with Sidewalk Exterior Features

Welcome to Maitland, Florida, a charming city that beautifully blends suburban tranquility with urban convenience. Nestled in the heart of Orange County, Maitland is known for its lush landscapes, picturesque lakes, and vibrant community spirit. With a rich history dating back to the 19th century, this city boasts a plethora of cultural attractions, including the Maitland Art Center and the historic Waterhouse Residence Museum, making it a delightful place to call home.

One of the standout features of Maitland is its commitment to creating a walkable and connected community. Many homes in the area feature inviting sidewalks that encourage leisurely strolls, morning jogs, or evening bike rides. This pedestrian-friendly design enhances the neighborhood feel, allowing residents to easily access local parks, shops, and dining options. Imagine taking a leisurely walk along tree-lined streets, greeting neighbors, and soaking in the warm Florida sunshine.

Maitland's real estate market offers a diverse array of homes, many of which showcase charming sidewalk exterior features, perfect for families and individuals who appreciate a sense of community and accessibility. Whether you’re seeking a cozy bungalow or a spacious family home, you’ll find properties that cater to every lifestyle.

In Maitland, you’re not just purchasing a home; you’re investing in a lifestyle. With its exceptional schools, abundant recreational opportunities, and a strong sense of community, Maitland is a place where you can truly thrive. Come explore this enchanting city and discover the perfect home with sidewalks that lead to endless possibilities!

Newest Maitland Homes with Sidewalk Exterior Features

3 Beds ⋅ 2 Baths ⋅ Winfield SubDv. ⋅ 32751 Zip Code

Beautiful Winfield Community home in Maitland Florida will not last long. This 3 bedroom/2 bath home has so much to offer. The property recently has had a new roof put on this year in 2026, new AC unit this year in 2026, and freshly painted in 2026. The kitchen features an eat in bar top as well as a large island for plenty of use-able countertop space. The back yard is fully fenced in for privacy. The home comes with a stove, refrigerator, microwave, washer, and dryer. The garage is oversized for 2 cars with extra space for storage. The flooring is ceramic in the main living areas for easy cleaning when needed. Low HOA dues for an upscale community. Dont miss out on this home.

1866 Bobtail Drive, Maitland

3 Beds ⋅ 2 Baths ⋅ Forest Brook 2nd Sec SubDv. ⋅ 32751 Zip Code

Waterfront potential on Brookside Circle! Classic 3-bedroom, 2-bathroom property situated directly on peaceful Howell Creek with canoe access to the pond. The interior layout includes a living room with a window nook, a dedicated dining area, and a primary suite located off the dining room. The kitchen features a breakfast nook and opens directly into the main living area. A split floor plan places two secondary bedrooms on the opposite side of the home, alongside an indoor, air-conditioned laundry room. The second full bath opens directly to the screened pool deck to serve as a dedicated pool bath. The property sits on an expansive lot featuring a wide side yard and a deep backyard running along the creek. Filled with warmth and pride of ownership, the home showcases unique, hand-painted artistic touches throughout that reflect years of love—ready for the next owner to bring their own style. Ready for a complete transformation, this property presents an exceptional waterfront renovation opportunity. Schedule your tour today!

535 Brookside Circle, Maitland

5 Beds ⋅ 3 Baths ⋅ Stonewood First Add SubDv. ⋅ 32751 Zip Code

**STUNNING LAKEFRONT RETREAT IN MAITLAND!** Step into your next chapter at this exceptional lakefront property, where striking curb appeal is only the beginning. Perfectly positioned along the serene shores of **Lake Ruby**, this home blends timeless character with thoughtful modern updates. Inside, natural light pours through dramatic vaulted ceilings, illuminating spacious open living areas. The main gathering space flows seamlessly into the dining area, both showcasing **panoramic lake views** through expansive **updated sliding doors**, complemented by **built-in shelving** and **skylights** that enhance the airy ambiance. For the culinary enthusiast, the kitchen is more than a workspace—it’s a creative haven featuring **Corian countertops**, **tile backsplash**, abundant cabinetry, and **stainless steel appliances**, including a **newer dishwasher**. A charming **garden window** offers the perfect spot for plants or décor, while the eat-in nook provides yet another **stunning lakefront view**. Enjoy casual meals here or take the experience outdoors to the **incredible deck**, where Florida breezes set the tone for unforgettable gatherings. The formal dining room, anchored by a **wood-burning fireplace**, invites cozy evenings and intimate celebrations. Nearby, a versatile family room adapts to your lifestyle—ideal as an office, den, playroom, or even a fifth bedroom—with sliders leading to the **screened-in porch** and more peaceful lake scenery. The master suite is a true sanctuary, complete with a **private deck** overlooking Lake Ruby—perfect for sunrise reflections or unwinding at day’s end. The spa-inspired bathroom features designer tile and a rejuvenating shower, while the walk-in closet offers exceptional organization. Additional bedrooms provide comfort for family or guests, each with access to **updated bathrooms** that balance style and practicality. The home also includes an **indoor laundry room** with sink and **2-year-new washer and dryer**, plus numerous major updates: **roof (2019)**, **water heater (2023)**, **plumbing (2022)**, **AC (2017)**, and **irrigation with reclaimed water**. The beautifully landscaped **large corner lot** enhances the property’s charm. Convenience is unmatched with easy access to Maitland’s top amenities, schools, and major highways. This isn’t just a home—it’s a lifestyle, offering beauty, comfort, and the rare opportunity to live lakefront in one of the area’s most desirable communities. Homes with this level of character and luxury don’t come around often. Claim your future here.

956 Stonewood Lane, Maitland

2 Beds ⋅ 2 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

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

4 Beds ⋅ 2 Baths ⋅ English Estates Unit 2 SubDv. ⋅ 32751 Zip Code

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

4 Beds ⋅ 3 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code

This charming 4-bedroom, 3-bath home is in sought-after Dommerich Estates, one of the area’s most desirable neighborhoods. Designed for comfort, style, and everyday living, the home features a unique open floor plan with vaulted ceilings, a warm wood-burning fireplace, and an updated kitchen with solid wood cabinetry and granite countertops. Fresh interior and exterior paint, an oversized garage with built-in shelves, an extended paver driveway, and paver walkways add to the home’s curb appeal and move-in-ready feel. Step outside to a peaceful, private covered screened porch—your own outdoor retreat for relaxing mornings, quiet evenings, or future entertaining with plumbing and electrical already in place for a summer kitchen. Major updates include a 2025 roof, 2017 AC, and 2014 water heater. Dommerich Estates is known for its welcoming community feel and was thoughtfully designed around A-rated schools, making walking and biking to school safe and convenient. Ideally located just 1 ½ blocks from the elementary and middle school and 1 ½ blocks from the neighborhood lake lot, this home offers easy access to sunsets, fishing, and launching a watercraft for a day on the lake. Enjoy the best of Maitland living—close to Orlando yet rich with small-town charm, walkable neighborhoods, parks, downtown parties, concerts, and community events. With its prime location, thoughtful updates, inviting indoor and outdoor spaces, and access to highly desirable neighborhood amenities, this Dommerich Estates home delivers the lifestyle buyers are looking for.

550 Arapaho Trail, Maitland

3 Beds ⋅ 2 Baths ⋅ Greenwood Gardens Sec 01 SubDv. ⋅ 32751 Zip Code

Virtually Staged. Step into sophisticated modern living at 761 Robinhood Drive, a beautifully renovated three-bedroom, two-bathroom Maitland residence with no HOA. Designed for effortless everyday living and entertaining, this home welcomes you with an impressive open-concept floor plan, abundant natural light, dramatic 14-foot vaulted ceilings, contemporary fixtures, and luxury vinyl plank flooring throughout the main living areas. Expansive sliding glass doors create a seamless connection to the enclosed, screened-in concrete patio—an inviting retreat for relaxing, dining, or enjoying Florida’s beautiful weather. Beyond the patio, a spacious, fully fenced backyard provides endless possibilities for entertaining, gardening, or creating your own private outdoor oasis. At the heart of the home is a chef-inspired kitchen that balances bold style with thoughtful functionality. It features elegant waterfall-edge quartz countertops, a striking black tile backsplash, new stainless steel appliances, soft-close cabinetry, matte-black hardware, a pantry, a charming breakfast nook, and a smart digital faucet with temperature display. Every detail has been selected to create a modern and refined gathering space. The spacious primary suite offers private sliding-door access to the patio and a stylish barn-door entrance to the ensuite bathroom. Inside, you’ll find designer tile flooring, an oversized glass-enclosed walk-in shower, a vanity with quartz countertops, modern fixtures, and a generous walk-in closet. Both additional bedrooms have been refreshed and feature built-in closets. The equally impressive guest bathroom includes elegant tilework, a tub with glass shower enclosure, quartz countertops, and a contemporary vanity. This move-in-ready home has been extensively updated with a brand-new water heater, updated plumbing and electrical systems, a 2023 air-conditioning system, a 2018 roof, new LG washer and dryer, and new stainless steel appliances. Surrounded by Maitland’s scenic lakes and ideally positioned near the Maitland SunRail Station, Lake Lily Park, shopping, dining, and cultural attractions, this home offers exceptional Central Florida convenience. Located near Lake Sybelia Elementary School and with easy access to North Orlando Avenue, Maitland Boulevard, and Interstate 4, downtown Orlando, Winter Park, and surrounding destinations are only minutes away. Modern design, extensive upgrades, a prime Maitland location, and no HOA—761 Robinhood Drive is the opportunity you’ve been waiting for.

761 Robinhood Drive, Maitland

3 Beds ⋅ 3 Baths ⋅ Maitland Woods Third Add SubDv. ⋅ 32751 Zip Code

Nestled beneath a canopy of majestic oak trees in the highly sought after Maitland Woods neighborhood, this beautifully updated 3 bedroom, 2.5 bathroom pool home sits on an expansive .45 acre homesite, offering timeless charm, thoughtful updates, and the lifestyle you've been searching for. From the moment you arrive, you'll appreciate the instant curb appeal of this classic brick ranch home, framed by mature landscaping and one of Maitland Woods' picturesque tree lined streets. Inside, you're welcomed by a spacious formal living room that sets the tone for the warm and inviting spaces beyond. The beautifully renovated kitchen serves as the heart of the home, featuring stylish finishes, generous workspace, and an effortless flow into the family room, where a stunning brick fireplace creates the perfect place to gather with family and friends. The spacious primary suite offers a peaceful retreat complete with a custom walk in closet and an updated ensuite bath. Two additional bedrooms provide comfortable accommodations for family, guests, or a home office.' Designed for year round Florida living, the expansive screened lanai overlooks your own private backyard oasis featuring a saltwater pool, newer pergola, outdoor shower, and an oversized fenced backyard with plenty of room to entertain, play, or simply relax beneath the shade of mature oaks. Recent improvements include a new HVAC system (2025), complete replumbing, and updated electrical, offering peace of mind for years to come. Life in Maitland Woods is about more than just the home. Enjoy evening walks around the spring fed waters of Lake Sybelia, where neighbors gather to take in beautiful sunsets beneath the oak canopy. Just minutes away, charming downtown Maitland offers local restaurants, community events, the weekly farmers market, and beloved traditions like Movies in the Park. With Orangewood Christian School within walking distance and easy access to downtown Maitland, downtown Orlando, shopping, dining, and major roadways, this location perfectly blends small town charm with everyday convenience. This is more than a home. This is the sign you've been looking for. It's an opportunity to enjoy the timeless character, community, and lifestyle that have made Maitland Woods one of Central Florida's most cherished neighborhoods.

211 Talmeda Trail, Maitland

5 Beds ⋅ 4 Baths ⋅ Dommerich/Maitland Highlands SubDv. ⋅ 32751 Zip Code

Located on quiet cul-de-sac, this one-story 5 bedroom/4 bath, 3,136 sq ft ranch-style home is a short walk to A-rated Dommerich Elementary and Maitland Middle schools. This home sits on .29 of an acre that backs up to the preserved conservation. Functional floor plan with separate formal living and dining rooms, perfect for entertaining. Eat-in kitchen opens to the cozy family room anchored by the wood-burning fireplace. Expanded in 2008, the attached 900 sq ft in-law suite has a bedroom, living room, kitchenette and bath - ideal for an elderly parent or returning college grad. This flex space would also be ideal as an exercise room or home office. Primary bedroom has screened patio access and a walk-in closet. Three secondary bedrooms with access to two additional baths. Living areas have wood and tile flooring and the bedrooms have luxury vinyl plank. Out back is a sparkling screened pool overlooking the wooded back yard. Recent improvements include all new interior paint throughout (7/26) and roof ('22). Conveniently located near I-4, several parks, and excellent neighborhood restaurants. Charming library with books to share. No HOA. Welcome home!

2051 Dyan Way, Maitland

4 Beds ⋅ 2 Baths ⋅ Forest Brook Sec 2-A SubDv. ⋅ 32751 Zip Code

Virtually Staged. Welcome home to this spacious 4-bedroom, 2-bath pool home in Maitland. From the moment you arrive, you'll appreciate the attractive brick exterior and inviting curb appeal. Inside, a welcoming foyer is flanked by a large formal living room with parquet flooring and abundant natural light, while the formal dining room features classic wainscoting and connects directly to the updated kitchen. The kitchen offers granite countertops, wood cabinetry, stainless steel appliances, a breakfast bar, and overlooks the generous family room with French doors leading to the backyard. The split-bedroom floor plan provides plenty of privacy. Two spacious secondary bedrooms with engineered hardwood flooring are located on one side of the home and share a hall bath. The primary suite is tucked away on the opposite side and features engineered hardwood floors, a walk-in closet and an ensuite bath with a walk-in shower. A fourth bedroom is centrally located, making it an ideal guest room, nursery, or home office. Just off the kitchen, you'll also find a large laundry room with built-in cabinetry for extra storage and access to the oversized two-car garage, which offers additional storage space. Step outside to a fully fenced backyard with an updated vinyl fence, a large pool ready for your personal finishing touches, and plenty of yard space for entertaining, pets, or play. Whether you choose to resurface the pool right away or customize it over time, this backyard offers great potential to create your own private outdoor retreat. Conveniently located just off Howell Branch Road, you're only minutes from I-4, Downtown Maitland, Winter Park, shopping, dining, and everyday conveniences. Call today to schedule your private showing!

564 Brookside Circle, Maitland

3 Beds ⋅ 2 Baths ⋅ Dommerich Estates 1st Add Maitland SubDv. ⋅ 32751 Zip Code

**BOATING/LAKE ACCESS** Welcome to 553 Arapaho Trail, where timeless MID-CENTURY CHARM meets thoughtful modern living in the highly sought-after DOMMERICH ESTATES community of Maitland. Offering OVER 1,500 SQUARE FEET of beautifully maintained living space, this 3-BEDROOM, 2-BATHROOM HOME features a desirable SPLIT FLOOR PLAN designed for both privacy and everyday comfort. From the moment you arrive, you'll appreciate the exceptional curb appeal with LUSH, MATURE LANDSCAPING, a NEWLY PAINTED EXTERIOR, and an EXTRA-WIDE, EXTRA-LONG BRICK PAVER DRIVEWAY with room for up to SIX VEHICLES. Inside, the home's original character has been carefully preserved while incorporating today's most important updates, including a NEW ROOF (2025), NEW GUTTERS, WHOLE-HOUSE REPIPE, ELECTRICAL UPGRADES, HARDWOOD FLOORING THROUGHOUT, NEW KITCHEN APPLIANCES, an UPGRADED PRIMARY EN-SUITE, stylish UPDATED LIGHTING FIXTURES, an EXTENDED ATTIC WITH ABUNDANT STORAGE, and a PAINTED GARAGE FLOOR. One of the neighborhood's rare homes with BURIED ELECTRICAL SERVICE, the property also offers a cleaner streetscape and added peace of mind. Step outside and discover your own private backyard retreat featuring an INCREDIBLE SCREENED-IN POOL, an expansive BRICK PAVER POOL DECK, and a charming BRICK PAVER GARDEN WALKWAY winding through beautifully landscaped grounds—perfect for entertaining or relaxing year-round. Beyond the home, DOMMERICH ESTATES continues to impress with its welcoming sense of community and location within one of Central Florida's most desirable school districts, originally designed around A-RATED SCHOOLS to make walking and biking to class safe and convenient. Residents also enjoy access to a VOLUNTARY, LOW-COST HOA that includes a PRIVATE BOAT RAMP to the WINTER PARK CHAIN OF LAKES, opening the door to BOATING, PADDLEBOARDING, FISHING, and unforgettable days on the water. The CITY OF MAITLAND offers the perfect balance of convenience and charm with its WALKABLE NEIGHBORHOODS, beautiful parks, local festivals, downtown concerts, and community events, while world-renowned PARK AVENUE in Winter Park is just minutes away for AWARD-WINNING DINING, BOUTIQUE SHOPPING, ART GALLERIES, and weekend brunch. This is more than just a home—it's an opportunity to experience one of CENTRAL FLORIDA'S MOST BELOVED NEIGHBORHOODS and lifestyles.

553 Arapaho Trail, Maitland

3 Beds ⋅ 3 Baths ⋅ Park Lake Grove Condo SubDv. ⋅ 32751 Zip Code

Welcome home to this spacious 3-bedroom, 2.5-bath condo in the desirable Park Lake Grove community. Enjoy peaceful lake views from your living room, and the convenience of an attached 1-car garage. The thoughtfully designed floor plan offers generous living space, 2 primary bedrooms with en suites upstairs, natural light, and plenty of storage. Community amenities include a pool and lake access. Conveniently located near shopping, dining, major highways, and downtown Orlando.

603 Waverly Lane Unit 405B, Maitland

Start Your Search