Maitland Homes with Pool

Maitland Homes with Pool

Welcome to Maitland, Florida – a charming city that beautifully blends the tranquility of suburban living with the vibrancy of urban conveniences. Nestled just north of Orlando, Maitland is renowned for its picturesque landscapes, lush parks, and a rich cultural scene. With its tree-lined streets and friendly neighborhoods, it's no wonder that this hidden gem has become a sought-after destination for families, retirees, and professionals alike.

Maitland boasts a variety of recreational opportunities, including the stunning Lake Maitland and the serene Lake Sybelia, perfect for boating, fishing, or simply enjoying a peaceful afternoon by the water. The city is also home to a thriving arts community, with venues like the Maitland Art Center and the Enzian Theater offering a taste of local culture and entertainment.

For those seeking a home that embodies the essence of Florida living, Maitland's real estate market features an array of stunning properties, including homes with inviting pools. Imagine stepping into your backyard oasis on a warm Florida day, where a sparkling pool awaits you, perfect for refreshing swims and entertaining friends and family. Whether you prefer a modern design or a classic style, Maitland offers a diverse selection of homes with pools that cater to every taste and lifestyle.

Living in Maitland means enjoying the best of both worlds – a serene suburban atmosphere with easy access to the excitement of Orlando. With top-rated schools, shopping, and dining options just moments away, it’s the ideal place to call home. Discover your dream home with a pool in Maitland today, and experience the perfect blend of comfort and convenience in this enchanting city!

Newest Maitland Homes with Pool

448 Banyon Tree Circle Unit 206, Maitland
$120,000
3 Beds ⋅ 2 Baths ⋅ O6448873 MLS ⋅ 448 BLDG.
Excellent investment opportunity in Carrington Park! This 3-bedroom, 2-bathroom condominium is located on the first floor and offers a convenient location in Maitland, with easy access to shopping, dining, major roadways, and nearby employment and educational centers. The property is currently rented for $1,650 monthly through August 31, 2027, providing rental income for the new owner from day one. The community is centrally located near the shopping and commercial areas along Howell Branch Road and SR 436, with convenient access to Full Sail University, Winter Park, and surrounding areas. The HOA covers water, sewer, and exterior maintenance, offering additional convenience for property owners. Whether you are expanding your investment portfolio or looking for a property in a desirable Central Florida location, this condo presents an excellent opportunity. Don't miss the chance to own an income-producing property in a convenient and well-connected area of Maitland!

448 Banyon Tree Circle Unit 206, Maitland
1275 Lake Shadow Circle Unit 13107, Maitland
$164,900
1 Beds ⋅ 1 Baths ⋅ O6448232 MLS ⋅ 1275 BLDG.
Welcome to luxury, comfort, and convenience at this beautifully transformed ground-floor 1-bedroom, 1-bath condo in the gated community of Visconti West. Every square foot reflects thoughtful upgrades, quality, and style. The stylish and functional kitchen features $5,500 in brand new appliance upgrades completed in 2024, including a built-in microwave. The laundry room includes a new washer and dryer, added shelving, and cabinetry. The home has also been freshly painted throughout, creating a crisp, modern, move-in-ready feel. Additional 2024 improvements include a $10,000 bathroom remodel featuring a walk-in shower, a $1,500 double-paned bedroom window, $300 in lighted ceiling fans, and $300 in overhead lighting. All-new electrical outlets, a new fire alarm system, and new blinds add even more function and convenience. The tile floors have been professionally deep cleaned and re-grouted, and the air ducts have been cleaned too. For added peace of mind, the air conditioner was updated in August 2026 at a cost of $2,200, providing an important recent improvement to the home. Beyond the condo, enjoy the serene waterfront setting and resort-style amenities Visconti West has to offer, including a clubhouse, fitness center, playground, sparkling pool, tennis courts, sidewalks for leisurely strolls, and a designated pet-walking area. With convenient access to I-4 and close proximity to Winter Park, Altamonte Springs, and the RDV Sportsplex, this home offers an ideal combination of location, lifestyle, and extensive recent improvements. Move in, settle in, and enjoy a home where much of the updating has already been done for you.

1275 Lake Shadow Circle Unit 13107, Maitland
2514 Tuscarora Trail, Maitland
$899,000
4 Beds ⋅ 3 Baths ⋅ O6448334 MLS
Welcome to 2514 Tuscarora Trail, a beautiful, fully renovated lakeview pool home nestled in the heart of Maitland, Florida! This spacious single-story residence offers 4 bedrooms, 3 bathrooms, and approximately 3,000 square feet of living space on a generous 0.43-acre lot. Step inside to discover an inviting open floor plan featuring spacious living and dining areas, a brand new gourmet kitchen, and plenty of natural light. The thoughtfully designed layout provides comfortable spaces for everyday living and entertaining. This home features a brand new HVAC unit, 2024 roof, the home has been fully repiped, including the all sewer lines. Step outside to your own private retreat, featuring a sparkling swimming pool, covered patio, expansive backyard, and peaceful lake views. Whether relaxing poolside or hosting outdoor gatherings, this property offers an exceptional Florida lifestyle. Additional highlights include a solar panel system, ample parking, and convenient access to Winter Park's popular shopping, dining, entertainment, and recreational destinations. Enjoy the perfect combination of space, comfort, outdoor living, and a convenient Central Florida location. Schedule your private showing and discover everything this Maitland property has to give

2514 Tuscarora Trail, Maitland
219 Quayside Circle Unit B9, Maitland
$799,000
2 Beds ⋅ 3 Baths ⋅ O6448045 MLS ⋅ Na BLDG.
Tucked inside The Moorings, one of Maitland's most charming lakeside enclaves, 219 Quayside Circle sets a new standard for the community, and it comes with its own DEEDED BOAT SLIP on Lake Maitland, your gateway to the Winter Park Chain of Lakes. This two-story townhome-style condo has been completely reworked around an open, light-filled floor plan. The kitchen takes center stage with a 13-foot island wrapped in waterfall quartz. The same quartz runs across the counters and climbs the walls as a dramatic full-height backsplash, paired with GE Monogram and Café appliances and solid wood soft-close cabinetry. In the living room, soaring ceilings frame a wood-burning fireplace, and a sunroom/den just off the dining area makes an easy spot for morning coffee, a home office or a reading nook. Upstairs, two en-suite bedrooms each offer their own private retreat. The primary features a vertical wood-slat accent wall with sconce lighting, a generous walk-in closet, and a spa-inspired bath with an oversized walk-in shower that encloses a soaking tub. Throughout the home you'll find exquisite tile work, new PGT insulated windows and Andersen French doors that pour in natural light, recessed lighting, iron stair railings, and all-new baseboards and trim. A 2023 HVAC system and water heater add peace of mind, and the attached one-car garage includes a laundry room. Residents enjoy a community pool, recreation hall and dock, with Lake Lily Park and its year-round events right nearby. Park Avenue's boutiques and restaurants are about five minutes away. Move-in ready with true lock-and-leave convenience, this is lake living without the upkeep.

219 Quayside Circle Unit B9, Maitland
1100 S Orlando Avenue Unit 306, Maitland
$599,900
2 Beds ⋅ 2 Baths ⋅ O6447927 MLS ⋅ West Cove BLDG.
Exquisitely remodeled, from top to bottom, 2 bdrm 2 bath luxury condo on Lake Maitland, the largest of the Winter Park Chain of Lakes. Enjoy panoramic lake views and unimaginable sunrises and space shuttles from your large balcony or sitting in your living room or kitchen or from your primary bedroom. Home features EVERYTHING NEW, electrical, plumbing, ductwork, fixtures, appliances; beautiful crown moldings, engineered wood floors, built-ins, spacious baths -- while located in the heart of Maitland walking distance to the Enzian, Lake Lilly, and several restaurants. Easy access to I-4 and major roads and a 5 minutes drive to shopping and restaurants on Winter Park's Park Avenue. Community features a clubhouse, fitness center, large pool and spa, kayak racks, patio and grilling area. Fee includes internet/cable; water, sewer, trash and on-site management. Enjoy condo living at its finest.

1100 S Orlando Avenue Unit 306, Maitland
1140 S Orlando Avenue Unit H-16, Maitland
$625,000
2 Beds ⋅ 1 Baths ⋅ O6438189 MLS ⋅ Hawthorne House BLDG.
EXQUISITE CONDO WITH BOAT SLIP AND DOCK ON THE WINTER PARK CHAIN OF LAKES! This stunningly reimagined corner unit boasting extra windows for light/space and a limestone porcelain zero entry threshold which extends inside-out opening out to a singular plane patio, showcasing a long lake view of Lake Maitland and extraordinary view of the morning sunrise over the lake, which is nestled on the Winter Park Chain of Lakes bordering Winter Park-and less than a mile to Park Avenue. This is penthouse style living, with a fully extensive elevated remodel by W DESIGNS LTD leaving nothing spared.As you enter the home, it features an exquisite wall of natural limestone spanning floor to ceiling which meets a beautiful and coffer ceiling of meticulously crafted millwork. An electric fireplace adds to the ambiance and is flanked by two custom bookcases. The dining area, also carries the refined custom millwork paneling throughout, with a built in banquette for seating which also provides ample storage. Aloft the solid wood dining table with custom French feather & down daybed cushions, there is a sophisticated sculpted artisanal chandelier by Cynara lined with gold leaf, lighting the area with prisms. The daybeds allow a comfortable and cozy area to watch TV. The open concept galley kitchen is completely built-in with custom paneling and cabinetry, adorned with brass cabinet pulls, and a fully integrated Fisher & Paykel paneled refrigerator . All appliances are 3 years of age with little use. Master bedroom, also features beautiful millwork throughout including a custom built-in wall unit for extra storage and custom-made bookshelves. New solid wood paneled doors are embellished with polished nickel and lucite knobs. All extra wide louvered shutters throughout, are custom hand milled shutters by Lloyd’s Shutter Shoppe. Bathroom has been redesigned with commercial grade, for longevity, seagrass wallpaper, a lacquered Italian floating vanity, marble wainscoting with architecture detail, marble shower with soaking tub, Contemporary Signature Hardware waterfall faucets offer the jewelry for the bathroom. This masterfully done jewel box, Pied-à-Terre, is the epitome of simple luxury perfectly situated in this cozy community on Lake Maitland.

1140 S Orlando Avenue Unit H-16, Maitland
223 Quayside Circle Unit C11, Maitland
$537,000
3 Beds ⋅ 3 Baths ⋅ O6447408 MLS ⋅ 223 BLDG.
Enjoy the charm of The Moorings on Lake Maitland in this inviting three-bedroom, two-and-a-half-bath townhome with an attached one-car garage. High ceilings, natural light, and warm wood flooring complement the living spaces, while a wood-burning fireplace gives the living room a welcoming focal point. The kitchen features white cabinetry with glass-front accents, stainless steel appliances, and a breakfast nook framed by a bay window. A separate dining area provides space for gathering, and French doors open to a screened porch overlooking the community’s green space and mature trees. All three bedrooms are upstairs, including the primary suite with a walk-in closet and an updated bathroom featuring a double vanity and walk-in shower. Two additional bedrooms share a full bathroom, with a convenient half bath downstairs. Plantation shutters in most rooms add character and privacy. Residents enjoy a community pool, clubhouse, and community dock on Lake Maitland. Walk over to Lake Lily Park for the Sunday morning farmers’ market or enjoy Luke’s Kitchen + Bar and Antonio’s restaurant + Italian market just across the street! Nearby Maitland Plaza and Maitland Social offer additional shopping and dining, with pharmacies, medical offices, and fitness studios also close by. Publix, Whole Foods, Nordstrom Rack, and Sephora are within a few blocks, while the hopping Winter Park Village and Park Avenue’s boutiques, restaurants, and cultural attractions are just minutes away. Convenient access to I-4 and excellent nearby public and private schools further enhance this central Maitland location.

223 Quayside Circle Unit C11, Maitland
623 Green Meadow Avenue, Maitland
$525,000
3 Beds ⋅ 2 Baths ⋅ O6448059 MLS
Welcome Home! Check out this beautiful 3 bedroom 2 bathroom single family home with a beautiful pool in a NO HOA neighborhood! Take full advantage of the morning sunrise directly in your backyard facing due east. This home features a gorgeous backyard with a beautiful pergola and screened in porch overlooking your spacious backyard oasis private pool. This property backs up to a conservation lot so no rear neighbors! As soon as you walk up you'll notice the archway that is covered in beautiful flowers when in season! As soon as you walk into the foyer you'll notice the massive open living area with a great Kitchen, Living Room & Dining room combo! The kitchen is sure to bring out your inner chef! Featuring plenty of lighting, a massive kitchen island and ample countertop & cabinet space! This home is perfect for entertaining, with the French doors out to your beautiful screened in patio and backyard steps away! The master bedroom features updated flooring, a spacious walk in closet and private master bathroom. This home is an amazing canvas for you to come in and make it your own! Reach out to the listing agent today to schedule your showing! Roof, HVAC & Water Heater 2021.

623 Green Meadow Avenue, Maitland
1161 Charming Street, Maitland
$585,000
4 Beds ⋅ 4 Baths ⋅ O6446305 MLS ⋅ 1161 BLDG.
Sunrises over Lake Charity, two primary suites, and a kitchen made for serious cooking — this Montacino townhouse isn’t like anything else on the market. With 4 bedrooms, 3.5 baths, and new luxury vinyl flooring throughout, it’s effortlessly modern and move-in ready. The first-floor primary suite offers single-level living with a spa-inspired bathroom with two vanities, a tub and shower and generous closet space. The second-floor primary provides a private retreat for guests or family — a rare and highly sought-after layout. The brand new LG induction oven with air fryer and Café double dishwasher make cooking and cleaning a breeze, and the private back patio is perfect for morning coffee, entertaining or evening relaxation. An extra-large two-car garage adds plenty of storage for bikes, tools, or hobbies. Nestled in a gated community with a pool, this home blends comfort, security, and lifestyle convenience. With minutes to I-4, Winter Park, Downtown Orlando, and all of Maitland’s best dining and shopping are within easy reach. A rare floor plan, thoughtful updates, and flexible living spaces — this Montacino gem truly stands apart.

1161 Charming Street, Maitland
1010 Winderley Place Unit 100, Maitland
$349,000
2 Beds ⋅ 3 Baths ⋅ O6444498 MLS
Discover the best of Maitland living in this light and bright end-unit townhome in the gated, lakefront community of Lake Destiny. Offering 2 bedrooms, 2.5 bathrooms, and 1,640 square feet, this inviting home features vaulted ceilings, a versatile loft perfect for a home office, media room, or additional living space, and plenty of valuable upgrades. The updated kitchen showcases crisp white cabinetry and contemporary quartz countertops as well as a dining area for special gatherings. Low-maintenance ceramic tile and laminate flooring flow throughout the first floor, drawing you into the two-story living room. This space is enhanced with transom windows, adding even more natural light creating an airy feel. Upstairs, the loft and two spacious bedrooms offer comfortable retreats, with brand-new carpet adding a fresh touch. The primary features a walk-in closet and plenty of storage in the ensuite bathroom. You also have a beautiful water view further adding to the tranquilty of the space. For added convenience, there’s an interior laundry room and a one-car garage. Step outside and take in the serene water feature view from your private patio or walk over to the community pool for a relaxing afternoon soaking up the sunshine. When you’re heading off to work or play, I-4 and 414 are just minutes away and one of Orlando’s most popular fitness facilities, Genesis Health Club, is just 1.5 miles away. Costco, Target, Home Depot, along with a variety of shopping and dining options are a short 10 minute drive and Winter Park and downtown Orlando are less than 20 minutes from the home as well. Recent improvements include new upstairs carpeting, a Kinetico whole-home water softener and filtration system with reverse osmosis filtration at the kitchen sink, a roof replaced in 2023, a 2020 water heater, and an AC system updated in 2018/2019. **The home is available to be sold unfurnished or fully furnished for a complete turnkey experience!**

1010 Winderley Place Unit 100, Maitland
1310 Winston Road, Maitland
$635,000
4 Beds ⋅ 3 Baths ⋅ O6446286 MLS
Welcome to this exceptional four-bedroom, two-and-a-half-bathroom pool home in the heart of Maitland, offering an ideal blend of comfort, privacy, and Florida-style living. Situated in an established neighborhood near Kewannee Park, this beautifully maintained residence welcomes you with a long driveway, side-entry two-car garage, manicured landscaping, and a charming paver walkway leading to an elegant double-door entry. Step inside to a light, bright, and spacious open-concept floor plan featuring tile flooring throughout the main living areas. The well-appointed kitchen is designed for both everyday living and entertaining, showcasing granite countertops, rich cherry wood cabinetry, stainless-steel appliances, a center island with cooktop, and a stylish vent hood. The adjacent dining area provides an inviting space for gatherings, while the expansive living room features an impressive 72-inch ceiling fan and abundant natural light. A comfortable family room creates the perfect gathering space and features a wood-burning fireplace, adding warmth and character to the home. French doors open to your private outdoor oasis—an impressive screened-in lanai featuring a sparkling swimming pool, spacious sundeck, relaxing spa, and attractive water feature. Whether you’re enjoying your morning coffee, soaking up the Florida sunshine, or entertaining family and friends, this exceptional outdoor living space is designed to be enjoyed year-round. Beyond the pool area, the property offers a peaceful conservation view with no rear neighbors, creating an enhanced sense of privacy and a serene natural backdrop rarely found in such a convenient location. The spacious primary suite provides a private retreat with a generous walk-in closet and an ensuite bathroom featuring dual vanities, granite countertops, and a beautifully tiled walk-in shower. Three additional generously sized bedrooms offer flexibility for family, guests, a home office, or a hobby room. A secondary bathroom features a granite vanity and convenient shower/tub combination. Additional highlights include a roof replaced in 2019, ceiling fans throughout, spacious living areas, a side-load two-car garage, and a desirable established-community setting. Location is another standout feature. Enjoy easy access to SR 17-92, SR 436, and I-4, providing convenient connectivity throughout Central Florida. You’re just a short drive from Orlando, Winter Park, Casselberry, and Altamonte Springs, as well as shopping, dining, fitness centers, banks, supermarkets, Lowe’s, Home Depot, parks, and everyday conveniences. With its private pool, screened lanai, conservation setting, no rear neighbors, spacious open floor plan, updated kitchen features, primary suite, and highly convenient Maitland location, this home offers the perfect opportunity to enjoy the best of the Central Florida lifestyle.

1310 Winston Road, Maitland
1931 Michael Tiago Circle, Maitland
$445,000
3 Beds ⋅ 3 Baths ⋅ O6445127 MLS ⋅ 1931 BLDG.
Welcome to this beautiful 3-bedroom, 2.5-bath townhome offering approximately 2,100 square feet of comfortable living space in the gated community of Maitland Village. The open floor plan features spacious living and dining areas with abundant natural light, creating an inviting setting for everyday living and entertaining. The kitchen flows seamlessly into the main living areas, while all three bedrooms are located upstairs for added privacy. The generous primary suite provides a relaxing retreat with an en-suite bathroom and ample closet space. Additional features include an interior laundry area, a private outdoor patio, and an attached two-car garage. Maitland Village offers gated access, a community pool, clubhouse, sidewalks, and beautifully maintained surroundings, also includes water, Cable & internet . Conveniently located near I-4, Maitland Center, Winter Park, Downtown Orlando, shopping, dining, and entertainment. Schedule your private showing and discover the space, convenience, and lifestyle this Maitland townhome has to offer!

1931 Michael Tiago Circle, Maitland
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