Maitland Homes with Pool Amenities

Maitland Homes with Pool Amenities

Welcome to Maitland, a charming city located in the beautiful state of Florida. Known for its rich history, picturesque landscapes, and vibrant community, Maitland offers an excellent quality of life for residents and visitors alike.

Situated in the heart of the Sunshine State, Maitland boasts a prime location that provides easy access to all that Central Florida has to offer. Whether you're looking for outdoor adventures, world-class entertainment, or top-notch shopping and dining options, you'll find it all within a short drive from Maitland.

One of the standout features of Maitland's real estate market is the availability of homes with pool amenities. With the warm Florida climate, having a pool in your backyard is a fantastic way to beat the heat and enjoy the outdoors in the comfort of your own home. Whether you're looking for a cozy single-family home or a spacious luxury estate, Maitland offers a variety of options with pool amenities to suit every lifestyle and budget.

Having a pool at home not only provides a refreshing escape during hot summer days but also adds value to your property. It creates a perfect setting for entertaining guests, hosting pool parties, or simply relaxing with your loved ones. Imagine spending your weekends lounging by the pool, soaking up the sun, and creating lasting memories with family and friends.

If you're searching for a home in Maitland, be sure to explore the numerous listings that feature pool amenities. From modern designs to traditional styles, there's a home for everyone in this vibrant city. Contact a local real estate agent to help you find the perfect Maitland home with a pool that meets your needs and preferences.

Don't miss out on the opportunity to experience the best of Florida living in Maitland. Start your search today and find your dream home with pool amenities in this idyllic city.

Newest Maitland Homes with Pool Amenities

1325 Lake Shadow Circle Unit 12103, Maitland
$199,000
2 Beds ⋅ 2 Baths ⋅ Visconti West SubDv. ⋅ 32751 Zip Code
Virtually Staged. Enjoy convenient first-floor living in the gated lakeside community of Visconti West! This two-bedroom, two-bath condominium offers an open living and dining area, high ceilings, and a split-bedroom layout. Each bedroom features an en-suite bathroom and walk-in closet, providing comfort and privacy. The kitchen includes a breakfast bar and closet pantry, while an interior laundry room accommodates the washer and dryer. A screened, covered patio offers space to relax outdoors, with an additional storage closet for everyday convenience. Community amenities include two lakeside pools, a fitness center, clubhouse, tennis and basketball courts, and a car wash area. The monthly association fee includes water, sewer, trash service, and exterior and grounds maintenance. Located near Maitland Boulevard and I-4, Visconti West offers convenient access to downtown Orlando, Winter Park, shopping, dining, and entertainment. Discover a comfortable home with first-floor convenience and an array of community amenities.

1325 Lake Shadow Circle Unit 12103, Maitland
1507 Grove Street, Maitland
$230,000
3 Beds ⋅ 2 Baths ⋅ Park Lake Villas Condo SubDv. ⋅ 32751 Zip Code
Welcome home to this beautifully maintained 3 bedroom, 2 bath, one-story condo offering 1,256 square feet of comfortable living space in one of Central Florida's most sought-after school districts, zoned for Dommerich Elementary and Maitland Middle School. This move-in-ready home features significant recent upgrades, including a brand-new roof (2024) , new HVAC system (2024), and new Electrical panel (2026), providing peace of mind and energy efficiency for years to come. Inside, you'll find a functional floor plan with spacious living and dining areas, generous bedrooms, and abundant natural light throughout. Step outside to your large, private, fully fenced back patio, ideal for entertaining, relaxing, or enjoying outdoor living. The patio offers direct access to the community pool, making it easy to enjoy Florida's year-round sunshine. Ideally located near shopping, dining, and major roadways, this home combines low-maintenance living with top-rated schools and outstanding community amenities.

1507 Grove Street, Maitland
1140 S Orlando Avenue Unit J12, Maitland
$225,000
2 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
Welcome to this amazing opportunity to own inside the highly coveted Lake Maitland Terrace community. This second floor condo is two bedrooms and one bathroom and ready to be renovated & updated. It’s time to enjoy a low-maintenance turnkey lifestyle in the perfect walkable location…just steps away from dining, famed Enzian Theater, Fort Maitland Park, Lake Lily Park and a moments drive to all other conveniences of Maitland, Winter Park and all surrounding areas. Lake Maitland Terrace amenities include a large community pool, grill area, shuffleboard, fishing dock & pier, kayak storage and direct access to Lake Maitland and the beautiful chain of lakes. Enjoy peaceful lakefront sitting & views EVERY DAY. BRAND NEW HVAC - September 2026. Water & trash is included in your monthly fees. Private small storage unit located near the condo. Multiple laundry centers onsite in the community plus an option to plumb inside the condo for private laundry (project completed by multiple condo owners). One (1) assigned parking space and multiple open spaces. Zoned for TOP schools. WELCOME HOME!

1140 S Orlando Avenue Unit J12, Maitland
206 Quayside Cir Unit 203, Maitland
$950,000
2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo Bldg 03 SubDv. ⋅ 32751 Zip Code
This Winter Park Chain of Lakes condominium has been completely reimagined to the highest of standards with meticulous attention to detail, providing luxury living in the ideal Maitland location. The sale includes a desirable, dedicated boat slip, giving you access to the entire Winter Park Chain of Lakes for year-round enjoyment and unparalleled lake views. A corner unit, the property is filled with beautiful natural light, creating a bright, fresh ambiance against the quintessential Florida backdrop of sunshine. The home has been entirely reconstructed from ground up, featuring updated electrical, plumbing, HVAC, windows, sheetrock, an on-demand water heater, a whole-home water filter, in-floor heating, flooring, paint, lighting, a kitchen and baths. Every interior detail showcases bespoke craftsmanship, including authentic oak chevron floors, designer wall and trim treatments, handcrafted base and crown moldings and a Level 5 sheetrock finish with sprayed matte paint. Elevating the modern aesthetic are a double-sided Dimplex fireplace, integrated Lutron lighting and shades, handcrafted HVAC vents and built-in Samsung Frame TVs. The home also offers brilliant storage solutions, featuring a large hidden storage closet concealed behind the entryway mirror alongside integrated hallway doors for seamless HVAC and closet access. The gourmet kitchen flows openly into the gathering space with direct views of the lake, centering around a seated island and an intimate eat-in area perfect for dining or entertaining. Designed to be efficient, sleek and integrated with the formal living spaces, it boasts a restaurant-quality induction cooktop and speed oven, custom cabinetry with real brass inlays and brass doors, a Brizo touch faucet with on-demand hot water and an integrated Thermador refrigerator with touch-sensitive doors. The luxurious owner's retreat enjoys stunning water views, upgraded lighting, a fully organized walk-in closet and the ambiance of the double-sided fireplace. The primary bath offers an indulgent, spa-like experience with book-matched porcelain marble slabs, a shower with body sprays, in-floor heating and a heated towel warmer. Thoughtful conveniences include a private water closet with a Kohler Veil intelligent toilet and bidet, seamless marble finishes and double sinks paired with oversized medicine cabinets for ample storage. Perfectly positioned in a premier Lake Maitland location, the property is just across the street from hours of scenic trails weaving around the lakes of Maitland and Winter Park. Exceptional dining and coffee options like Luke’s, Francesco’s, Antonio’s and Starbucks are just a short distance away, alongside numerous other local restaurants and bars. Daily conveniences are effortless with Whole Foods, Trader Joe's, Publix, Target, Home Depot and REI all within a five-minute drive, while the historic Enzian Theater is close by for the ideal movie night.

206 Quayside Cir Unit 203, Maitland
1100 S Orlando Avenue Unit 306, Maitland
$599,900
2 Beds ⋅ 2 Baths ⋅ West Cove SubDv. ⋅ 32751 Zip Code
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 ⋅ Lake Maitland Terrace SubDv. ⋅ 32751 Zip Code
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 ⋅ Moorings On Lake Maitland Condo Bldg 05 SubDv. ⋅ 32751 Zip Code
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
559 Flemming Way Unit 203, Maitland
$103,000
1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code
Virtually Staged. Welcome to this well-maintained and move-in-ready second-floor condo, offering comfort, convenience, and a great location! This charming 1-bedroom, 1-bathroom unit features a spacious layout, a large walk-in closet, and a private outdoor patio where you can enjoy your morning coffee or relax after a long day. The property is currently vacant and ready to show, making it an excellent opportunity for a first-time homebuyer, seasonal resident, or investor looking for a low-maintenance property. The community offers a variety of desirable amenities, including a beautiful swimming pool, playground, and green spaces, and a great fitness/exercise room for residents to enjoy. The low HOA fee makes this property even more attractive for those looking for an affordable and convenient lifestyle. Laundry facilities are conveniently located outside across from the building. Located in a convenient area close to public transportation, stores, shops, restaurants, and everyday necessities, this condo provides easy access to everything you need. Whether you are looking for a comfortable place to call home or a great investment opportunity, this property offers an excellent combination of location, amenities, affordability, and convenience. Don't miss the opportunity to see this beautiful second-floor condo. The unit is vacant, in good condition, and ready for its new owner. Schedule your showing today!

559 Flemming Way Unit 203, Maitland
2520 Caper Lane Unit 204, Maitland
$130,000
1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code
**LOCATION, LOCATION!** Welcome to this charming and cozy 1-bedroom, 1-bathroom condo, ideally located in a convenient and desirable area near Semoran Blvd and Howell Branch Rd. This move-in-ready second-floor unit offers comfort, convenience, and easy access to everything you need. Enjoy being just walking distance from shopping, restaurants, supermarkets, and everyday essentials. The community offers a refreshing swimming pool, perfect for relaxing or enjoying quality time with family and friends, as well as ample parking for residents and guests. The property is also conveniently located near schools and educational institutions, including Rollins College, making it an excellent opportunity for professionals, or anyone looking for a convenient Central Florida location. HOA includes water, adding even more value and convenience. Whether you're looking for your next home, a low-maintenance place to live, or an investment opportunity, this condo is one you won't want to miss! Schedule your showing today and come see all this property has to provide.

2520 Caper Lane Unit 204, Maitland
856 Park Lake Circle Unit 51, Maitland
$228,000
2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
FIRST 6 MONTHS OF HOA PAYMENTS COVERED BY SELLER! The Park Lake Townhome Community is Maitland's hidden treasure! Offering for sale this extremely well-maintained townhome with 2 levels of comfortable living, a one-car garage, a generously sized laundry room under air, along with a lovely private screened back patio. As you step inside, look over your shoulder at the community pool that is literally steps from your front door! Once inside you will immediately fall in love with the wood-look easy care tile throughout the first floor. The large living room has the cutest window seat, streaming in tons of natural sunlight, with room for many different seating configurations. A convenient half bath to your left leads you into the kitchen and dining areas of the home. The large open concept kitchen features new appliances and shiny granite countertops with plenty of counterspace for the chef in the family. Off the dining area you'll find a set of sliding glass doors leading out to a private screened-in patio, perfect for morning coffees, grilling or entertaining friends and family. The patio also provides access to the attached one-car garage with garage door opener. This garage leads into the oversized indoor laundry room complete with a washer and dryer and a large storage area. As we head up the stairs, you'll notice the brand-new carpet in a lovely neutral color running on the stair treads and into the first bedroom for comfort and style. The 2nd bedroom features the wood-look flooring for added convenience. Both bedrooms share a well-appointed en-suite bathroom with a newly reglazed tub and shower. Freshly painted inside makes this home truly turn-key, either as a residence or as an investment. Residents of the Park Lake Townhome Community not only enjoy the sparkling community pool, but your HOA also covers trash collection, exterior maintenance (including the roof!) and lawn care! BONUS, there is a dock on the lake accessible by the community (think about walks to the lake in the mornings to watch the sunrise with your coffee or in the evenings to watch the sunset with your glass of wine!). Low Maintenance Living at its Best! And have I mentioned this AMAZING LOCATION? This lovely townhome community is less than 1 mile from N Park Avenue and less than 1/2 mile to 17/92 (Orlando Avenue)! The convenience to Maitland City Center, Rollins College, shops, restaurants, and the ease of commuting to work is 2nd to none. Make an appt to see this home, it is a gem! Note, some photos have been virtually staged for furniture placement.

856 Park Lake Circle Unit 51, Maitland
895 Park Lake Circle Unit 75, Maitland
$174,900
2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code
Look at that NEW Price! You decide to move in Now and upgrade as you go, benefitting from this below market price point, or Fix it up as little or as much as you want and keep the added Equity. 2 Bedroom, 1.5 Bath Townhouse with Living and Dining Rooms, Single Car Garage, Inside Laundry Room, and Oversized Fenced Patio. Located between 17-92 & I-4 with short commute to Winter Park, Downtown Orlando, or Maitland Center. Community Features include Swimming Pool less than 50 yards from Unit as well as Dock on Lake in Community. All Appliances in Unit. All Electrical Panels replaced July 2026, Alumicons to satisfy insurance for aluminum wiring added July 2026, Air Conditioning Replaced in 2016, Hot Water Heater in 2018, Garage Door in 2021. Sold As Is, Priced based on current condition.

895 Park Lake Circle Unit 75, Maitland
1140 S Orlando Avenue Unit E11, Maitland
$188,900
1 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code
LAKE ACCESS LIVING in one of Central Florida's most desirable locations! Welcome to 1140 S. Orlando Ave E11, a move in ready condo ideally located on the Winter Park and Maitland border in the sought after Lake Maitland Terrace community. Enjoy private access to Lake Maitland, part of the prestigious Winter Park Chain of Lakes, where you can spend your days paddle boarding, kayaking, boating, fishing, or simply relaxing by the water. Community amenities include a brand new lakefront pool, clubhouse available for private events, shuffleboard, putting green, community laundry facilities, COMMUNITY DOCK and additional storage. Inside, you'll find a functional floor plan with separate living and dining spaces, abundant natural light, and a well maintained interior that's ready to enjoy or personalize over time. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo offers exceptional value in an unbeatable location. Just minutes from Park Avenue and walking distance to local favorites including the Enzian Theater, Eden Bar, Luke's Kitchen and Bar, Antonio's, Francesco's, the Shoppes at Maitland, and beautiful Lake Lily Park. With easy access to downtown Winter Park, downtown Orlando, I 4, shopping, dining, and entertainment, this is low maintenance Florida living at its best.

1140 S Orlando Avenue Unit E11, Maitland
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