Maitland / Eatonville Homes with Private Pool type

Maitland / Eatonville Homes with Private Pool type

Welcome to Maitland and Eatonville, two enchanting communities nestled in the heart of Central Florida. Known for their rich history, vibrant culture, and picturesque surroundings, these areas offer a unique blend of suburban tranquility and urban convenience. With lush landscapes, scenic lakes, and a warm climate, Maitland and Eatonville are perfect for those seeking a serene lifestyle while still being close to the bustling city of Orlando.

One of the most appealing features of homes in this region is the availability of properties with private pools. Imagine stepping out into your backyard oasis, where you can unwind in your own sparkling pool, perfect for cooling off on those sunny Florida days or hosting summer gatherings with friends and family. These homes often come with spacious outdoor areas, ideal for barbecues, sunbathing, or simply enjoying the stunning sunsets that Florida is famous for.

Maitland boasts a range of amenities, including charming boutiques, delightful restaurants, and beautiful parks, making it a great place for families and individuals alike. Meanwhile, Eatonville, one of the oldest African American municipalities in the U.S., is rich in cultural heritage, with a strong sense of community and events that celebrate its history.

Whether you’re looking for a cozy family home, a luxurious retreat, or a charming abode with a private pool, Maitland and Eatonville offer an array of options to fit your lifestyle. Dive into the Florida dream and discover the joys of living in a community that truly feels like home!

Newest Maitland / Eatonville Homes with Private Pool type

161 White Oak Circle, Maitland
$899,000
4 Beds ⋅ 3 Baths ⋅ Maitland Grove SubDv. ⋅ 32751 Zip Code
Finally, a home for sale in the desirable Maitland Grove! Step through the front door into bright, open living spaces, thoughtfully redesigned in 2024 to connect the great room, dining area, and kitchen. At the heart of the home, an oversized waterfall quartz island anchors a beautifully renovated kitchen with custom cabinetry, abundant pantry storage, and updated appliances. Continue into the family room, where an electric fireplace and custom storage create a comfortable place to gather. The four-bedroom layout includes two primary suites and three full bathrooms, offering flexibility for guests or a home office. Waterproof laminate flooring carries through the home, while the Florida room adds another inviting space with a custom bar overlooking the backyard. Outside, enjoy a 60-foot lap pool and room to relax or entertain. Major improvements include a 2022 roof and whole-house repiping, along with copper electrical rewiring in 2024. near Lake Sybelia and Lake Catherine, the home offers easy access to downtown Maitland, Winter Park, and Orlando. There are many more upgrades throughout—ask for the detailed list of improvements. Schedule your private showing today!

161 White Oak Circle, Maitland
120 Minnehaha Road, Maitland
$1,349,000
3 Beds ⋅ 3 Baths ⋅ Packwood Sub SubDv. ⋅ 32751 Zip Code
Virtually Staged. CAR ENTHUSIAST’S DREAM! Welcome to 120 Minnehaha Road, a truly unique Maitland property offering beautiful interior finishes, exceptional energy efficiency, incredible versatility, and plenty of room to spread out on nearly half an acre. Even better, you’re just one block from shopping, offering incredible convenience while still enjoying the space and flexibility of this impressive property. Step inside to a bright and inviting interior filled with thoughtful architectural details. The gorgeous kitchen serves as the heart of the home, featuring generous cabinetry and counter space with an open layout perfect for everyday living and entertaining. Beautiful coffered ceilings add character and dimension to the living spaces and give the home an elevated, custom feel. The spacious primary suite is a retreat of its own, featuring an impressively large walk-in closet and a stunning primary bathroom designed with both style and function in mind. Generously sized secondary bedrooms and flexible living areas provide plenty of room for family, guests, or working from home. The home was also designed with energy efficiency in mind, helping create a comfortable and efficient living environment. The property features an approximately 10-year-old metal roof, along with a lightning avoidance/protection system. Another major benefit for car enthusiasts and EV owners is the 400-amp electrical service, which, per the seller, provides capacity to support multiple EV chargers or other similar high-demand electrical uses. And then there’s the detached workshop/guest house—a standout feature with incredible possibilities. Per the seller, the City of Maitland has designated the outbuilding as a “Guest House” for zoning purposes, adding even more potential for its future use. The sellers have also brought a sewer line to the building in preparation for future plumbing. Imagine the possibilities for a future in-law apartment, guest house, detached home office, studio, or multigenerational living space, or continue using it as an incredible workshop for your cars, projects, and hobbies. The existing guest-house designation may be advantageous for a future kitchen/bath addition or ADU-style use; buyers should independently verify permitted uses, zoning, and requirements with the City of Maitland. Enjoy a fantastic Maitland location just one block from shopping and convenient to Winter Park, Downtown Orlando, dining, entertainment, and major roadways. With its gorgeous interior, energy-efficient design, 400-amp electrical service, spacious primary suite, nearly half-acre setting, impressive detached workshop/guest house, and incredible future possibilities, 120 Minnehaha Road is anything but ordinary. Schedule your private showing and come experience everything this special property has to offer!

120 Minnehaha Road, Maitland
233 Flame Avenue, Maitland
$799,000
3 Beds ⋅ 5 Baths ⋅ Hidden Estates Unit 3 SubDv. ⋅ 32751 Zip Code
A RARE OPPORTUNITY IN HIDDEN ESTATES— NEARLY AN ACRE, LOW HOA & AN INCREDIBLE ENTERTAINER’S PARADISE! Tucked away in one of Maitland’s best-kept secrets, this expansive home offers over 3,200 square feet of living space on an oversized lot. With a long driveway providing abundant parking, a fully fenced yard and privacy sound wall, this property offers a level of space and privacy that is increasingly hard to find! The spacious and flexible floor plan features 3 bedrooms plus a large office that could easily be converted to a 4th bedroom, along with a living room, dining room, family room with a cozy fireplace, spacious eat-in kitchen, wet bar and an upstairs study area. The enormous first-floor primary suite includes a seating area, large ensuite bath with garden tub and separate shower, and two closets. One of which is oversized and large enough to create an office, dressing room, nursery or even a home gym. Upstairs, two additional bedrooms share a convenient dual Jack-and-Jill bath, offering excellent privacy and functionality. But the true showstopper is the outdoor living and entertainment space! A beautiful sunroom opens directly to the pool and an incredible backyard designed for entertaining. The sun room serves as a massive game room. The outdoor space has a beautiful freshly painted deck, multiple covered bar areas and an abundance of space for pool parties, family gatherings, game nights or simply relaxing in your own private retreat. A shed and expansive fenced yard provide even more room for hobbies, recreation and storage. The roof and HVAC were replaced in 2020. This is an incredible canvas to make your own while enjoying the space, privacy and amenities that are already here. Hidden Estates is a well-maintained, tucked-away community where homes rarely become available, yet you're still conveniently close to everything Maitland has to offer with easy access into Downtown Orlando, tons of shopping and dining options, great schools & hospitals. Call for more information and for your private showing today!

233 Flame Avenue, Maitland
1501 Oranole Road, Maitland
$650,000
3 Beds ⋅ 4 Baths ⋅ Bretton Woods SubDv. ⋅ 32751 Zip Code
Elegant Pool Home with Classic Florida Charm & Modern Comfort in Bretton Woods. Discover timeless charm and modern convenience in this stunning brick ranch, ideally situated on an expansive lot in desirable Bretton Woods. Thoughtfully updated for today’s lifestyle, this one-of-a-kind home combines character, comfort, and exceptional functionality. It’s easy to fall in love with this special property from the moment you arrive. Mature oak trees frame the front yard, while a welcoming porch sets the stage for the beautifully updated interior, featuring engineered hardwood flooring and a gourmet kitchen outfitted with top-of-the-line stainless steel appliances, including an induction Bosch cooktop, GE Monogram French door wall oven, GE Advantium microwave/oven, GE French door refrigerator, and KitchenAid dishwasher. A butler’s pantry provides exceptional storage and a seamless extension of the gourmet kitchen, making entertaining and everyday living effortless. The spacious owner’s suite offers a private retreat with an en-suite bath and cedar sauna. French doors open to an enclosed spa for the ultimate relaxation experience. A generous guest suite includes its own full bath and walk-in closet. A centrally located half bath provides added convenience for family and guests, while a separate full pool bath offers easy access from the outdoor living spaces. Recent improvements provide added peace of mind, efficiency, and year-round comfort. These include a newer roof, kitchen and powder room remodel, new Trane HVAC system with new ductwork featuring three separate zones, each with its own thermostat, new windows, pool pump, irrigation controls, and exterior paint. Step outside to your own private oasis. The expansive, fully fenced backyard features a sparkling pool framed by a large screened lanai, offering the perfect setting for entertaining, relaxing, or enjoying Florida’s beautiful weather. A large double gate provides convenient side-yard access for boat parking, while an outdoor shower adds to the poolside experience. Practicality is just as impressive, with a sizable laundry room, abundant storage, a circular driveway, and a two-car garage. A dedicated parking pad in front of the garage can accommodated an RV. Blending the warmth and character of old Florida with thoughtful modern updates, this exceptional property offers space, privacy, and convenience just minutes from I-4 and all that the Orlando area has to offer. A truly distinctive home with an unforgettable combination of charm and amenities to accommodate your lifestyle.

1501 Oranole Road, Maitland
315 Lake Seminary Circle, Maitland
$460,000
3 Beds ⋅ 2 Baths ⋅ Floridahaven 1st Add SubDv. ⋅ 32751 Zip Code
Charming 3-bedroom, 2-bath pool home in Maitland with tons of potential! This home is ready for a buyer with the vision to renovate, restore, and make it their own. The property needs substantial TLC throughout, but offers a wonderful opportunity to customize it to your personal style. Features include a private pool, screened patio, spacious yard, and covered parking. Conveniently located near shopping, dining, schools, and major roadways. Property is being sold AS-IS. Seller will not make repairs. Cash or conventional financing only.

315 Lake Seminary Circle, Maitland
210 Magnolia Road Unit 207, Maitland
$339,000
2 Beds ⋅ 2 Baths ⋅ Maitland House SubDv. ⋅ 32751 Zip Code
LOCATION, LIFESTYLE & LOW-MAINTENANCE LIVING IN THE HEART OF MAITLAND/WINTER PARK! Welcome to Maitland House, a hidden gem perfectly positioned between Maitland and Winter Park, where convenience, character and an unbeatable lifestyle come together. Located just steps from the iconic Enzian Theater and its lush Eden Bar, and minutes from Winter Park Village, Lake Lily and Park Avenue, this beautifully updated second floor 2 bedroom, 2 bath condo puts some of Central Florida’s best dining, entertainment, shopping and nightlife right outside your door. Inside, you’ll find a bright and inviting open floor plan with thoughtful updates throughout. The spacious living area features a wood burning fireplace, granite countertops, plantation shutters and custom-built closet systems with abundant shelving, drawers, shoe storage and hanging space. Step outside to your screened, pool view porch, the perfect spot for morning coffee, an evening glass of wine or simply enjoying the peaceful surroundings. The kitchen is equipped with a 2025 dishwasher, 2021 refrigerator, range and microwave, while the home also features a BRAND NEW water heater. The 2019 HVAC system includes electrostatic filtration and a UVC air purification system, with air ductwork replaced in 2024. Additional improvements include updated windows and attic insulation replaced in 2021. Maitland House offers the kind of amenities and conveniences that make everyday living easy. Enjoy a tranquil pool and clubhouse, community bathrooms, Weber Genesis grill, covered dog walk area, community laundry room with three large washers and three dryers, covered assigned parking and an assigned storage unit. The community itself has been well maintained, with exterior painting completed in 2025 and the parking lot resurfaced in 2026. And the HOA delivers exceptional value. Included with the association are water, sewer, exterior maintenance, and an impressive Spectrum entertainment and connectivity package. Schedule your showing today!

210 Magnolia Road Unit 207, Maitland
313 Macarthur Place, Maitland
$940,000
4 Beds ⋅ 4 Baths ⋅ Sybelia Place SubDv. ⋅ 32751 Zip Code
Beautiful two-story home nestled on a quiet cul-de-sac in desirable Maitland, FL right off of Lake Sybelia. Featuring a private pool, spacious layout, luxury kitchen, high ceilings and an ideal location. Sub-Zero Pro refrigerator, Wolf duel-fuel range, quartzite counter tops, custom cabinetry, gas tankless water heater. Walking distance from Lake Sybelia, Maitland farmer's market, library and restaurants. This 4 bedroom, 3 1/2 bathroom home offers the perfect blend of comfort and privacy in this perfect neighborhood!

313 Macarthur Place, Maitland
2051 Dyan Way, Maitland
$799,000
5 Beds ⋅ 4 Baths ⋅ Dommerich/Maitland Highlands SubDv. ⋅ 32751 Zip Code
Fantastic Maitland location! Situated 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, Maitland Middle and Winter Park High. This one-story 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
2624 Tuscarora Trail, Maitland
$785,500
3 Beds ⋅ 2 Baths ⋅ Dommerich Hills Second Add SubDv. ⋅ 32751 Zip Code
Discover a rare waterfront, pool-home in the desirable Dommerich Hills neighborhood. This exceptional property offers the ideal combination of family-friendly living, modern convenience, and breathtaking natural beauty. The open floor plan welcomes you with vaulted ceilings and natural light in the living room, dining room, kitchen, and family room. Bamboo flooring enhances the bedrooms and living room, while cool and durable tile flooring extends throughout the remaining living areas. The family room features a wood-burning stone fireplace, French doors to lanai, walk-in closet, Just outside, a lakeside fire pit is perfect for relaxing with family and friends while taking in peaceful water views and sunsets. The 12-foot-deep lanai overlooks the screened swimming pool and the 120 feet of lake frontage. Across the water lies a protected nature preserve, providing a backdrop of trees and nature. Whether hosting holiday gatherings, celebrating special occasions, or enjoying quiet evenings at home, the layout provides flexibility and comfort. Imagine your own pineapple patch and fruit trees! You’ll have seasonal oranges, Key limes, plums, and kumquats. Whether you're enjoying your morning coffee overlooking the lake or spending evenings under the stars, the outdoor spaces invite you to slow down and savor every season. The original 1968 home was replaced with a new home in 1998, including new electrical and plumbing and incorporating the updated building codes that required hurricane-resistance structures. In 2026 the home was connected to the new City of Maitland sewer system. The home has fresh paint throughout, new fixtures, and new water heater. This is more than just a home; it's a lifestyle. Here, families have room to grow, creating lasting memories, and nature is always just outside the door. This home has an exceptional waterfront setting and is situated very close to the Maitland and Winter Park Chain of Lakes. With a bright and inviting interior, thoughtful features, and an outstanding location, with A-rated schools, this property offers a rare opportunity to enjoy peaceful lakeside living without sacrificing convenience.

2624 Tuscarora Trail, Maitland
229 Flame Avenue, Maitland
$969,000
4 Beds ⋅ 4 Baths ⋅ Hidden Estates Unit 3 SubDv. ⋅ 32751 Zip Code
NEW PRICE + HOME WARRANTY! Seller is offering a one-year home warranty valued up to $810 for added peace of mind! Now priced at an exceptional value compared to recent comparable sales in the area. Seller welcomes offers—bring yours today! Welcome to Hidden Estates, where luxury, space, and flexibility come together in one of Maitland's most sought-after neighborhoods. Nestled on a quiet cul-de-sac, this rare single-story custom residence offers over 4,000 square feet of thoughtfully designed living space on an expansive three-quarter-acre lot. From the moment you arrive, you'll appreciate the impressive curb appeal, oversized driveway, and exceptional parking with plenty of room for multiple vehicles, boats, RVs, trailers, and recreational equipment. Inside, the home's spacious open layout is designed for both everyday living and entertaining, featuring soaring ceilings, hardwood flooring, crown molding, skylights, custom built-ins, plantation shutters, and a wood-burning fireplace. At the center of the home is a beautifully appointed chef's kitchen with custom mahogany cabinetry, granite countertops, a Thermador refrigerator, six-burner gas cooktop, double ovens, an oversized island with bar seating, and a generous walk-in pantry. The luxurious primary suite serves as a private retreat with its own sitting area, walk-in closet, heated bathroom floors, dual vanities, oversized walk-in shower, and freestanding soaking tub. One of the home's most unique features is its flexible layout, including a private guest suite situated on the opposite side of the home and a separate office overlooking a tranquil atrium, offering endless possibilities for guests, multigenerational living, a home office, or creative space. Step outside to your own private backyard oasis featuring a screened saltwater pool and spa with waterfall, an expansive covered lanai, and abundant outdoor living space designed for year-round Florida enjoyment. The oversized lot provides exceptional privacy while offering ample room to relax, entertain, or personalize the outdoor space. Additional highlights include a metal roof with copper fascia (2018), new septic drain field, and an unbeatable Maitland location convenient to shopping, dining, parks, major roadways, and everyday conveniences. This is a rare opportunity to experience the space, privacy, and versatility that define luxury living in Maitland.

229 Flame Avenue, Maitland
900 Brightwater Circle, Maitland
$1,125,000
5 Beds ⋅ 4 Baths ⋅ Maitland Club Rep SubDv. ⋅ 32751 Zip Code
Move-In Ready. Welcome to the Premier community of Maitland Club. The paver walkway and covered front patio lead you into the spacious foyer, featuring the elegant formal living and dining rooms with hardwood floors, crown molding and plantation shutters. The Kitchen features Granite countertops, 42” cabinets and lots of natural light. The warm and inviting family room area offers a woodburning fireplace with built-in shelving and an open floor plan. The 1st Floor Master has a Large Walk-in closet and master bathroom. Separate shower and Granite countertops. Upstairs boasts a Bonus Room, ample built-in storage, and a 5th Bedroom with a large Walk-in closet. Vaulted Ceilings throughout. The Screened Pool, Covered Lanai, and Large Fenced yard are great for entertaining. The community offers tennis and basketball courts and a 24-hour guard gated community. New roof in 2024 ($80,000 value). The carpet in the home was replaced in 2020.New A/C replacement in 2024.Termite bond which is transferable. TV's convey with the home in the living room. Pool has been resurfaced. The master bath and kitchen have been updated. Move-In Ready. This home is located within minutes of downtown Winter Park, Maitland Town Center, shopping, restaurants, hospitals, Genesis Health Club and easy access to I-4.

900 Brightwater Circle, Maitland
2494 Castlewood Road, Maitland
$560,000
4 Beds ⋅ 2 Baths ⋅ English Woods SubDv. ⋅ 32751 Zip Code
Virtually Staged. Owner welcomes all offers! Seller is motivated and open to considering all reasonable offers. Schedule your showing today! Welcome to 2494 Castlewood Road, a beautifully updated pool home situated on a spacious corner lot in one of Maitland's most established neighborhoods. This move-in-ready residence offers peace of mind with a newer roof, solar panels, updated HVAC, and extensive interior renovations throughout. Inside, you'll find an open and inviting floor plan featuring luxury vinyl flooring, updated bathrooms, modern fixtures, quartz countertops, and custom cabinetry. The spacious primary suite includes a walk-in closet and renovated en-suite bath, while the additional bedrooms provide flexibility for family, guests, or a home office. A large screened Florida room overlooks the backyard and creates the perfect space for year-round entertaining. Outside, enjoy the oversized swimming pool, expansive patio deck, fully fenced yard, and storage shed, offering plenty of room for recreation and outdoor living. Conveniently located just minutes from Downtown Maitland, Winter Park, Park Avenue, AdventHealth, shopping, dining, and major roadways including I-4, this home combines modern updates, energy-efficient features, and an exceptional location in the heart of Central Florida.

2494 Castlewood Road, Maitland
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