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389 Sultana Lane, Maitland
$769,000
3 Beds ⋅ 2 Baths ⋅ O6451568 MLS
Welcome to this beautifully renovated 3-bedroom Maitland pool home, featuring a spacious additional room ideal for a large 4th bedroom, home office, or bonus room, along with an expansive backyard perfect for outdoor living and entertaining. Blending timeless charm with modern sophistication, this thoughtfully updated, move-in-ready residence showcases designer finishes and the perfect balance of character, comfort, and contemporary style. Step inside to discover stunning original hardwood floors that have been meticulously refinished, complemented by updated flooring, interior doors, baseboards, and modern hardware. The beautifully renovated kitchen showcases a gas range, stylish finishes, and thoughtful upgrades, while the remodeled primary bathroom offers a fresh, elevated design. Extensive improvements provide both style and peace of mind, including new windows (2025), fresh exterior paint (2026), new gutters (2026), and updated plumbing, electrical, and much more. The exterior has been equally transformed with refreshed landscaping, new sod (2026), a newly installed driveway and walkway, and a new storage shed. The expansive backyard offers an inviting setting for entertaining, relaxing by the pool, gardening, or creating your own private outdoor retreat. With its extensive renovations, designer details, flexible living spaces, and exceptional outdoor setting, this Maitland property offers a rare opportunity to enjoy the charm of an established home with the convenience of modern updates. Schedule your private showing today!

389 Sultana Lane, Maitland

Courtesy of SOTERA LIVING

2365 Sierra Lane Unit 2365, Maitland
$339,500
2 Beds ⋅ 3 Baths ⋅ R4912212 MLS ⋅ 2365 BLDG.
Hidden Gem! This small community is quiet, independent, extremely well maintained and one of Maitland's most desirable communities. This unit is a spacious with two bedroom suites each with its own connected bathroom and an additional 1/2 bath four guest. Home is arranged with a separate dining room or office space, living room, kitchen and breakfast room. The kitchen is fully equipped with all appliances. There's also plenty of room with the breakfast nook which looks out onto the pool and tennis courts. A wood-burning fireplace creates a warm, welcoming atmosphere that links the living room, kitchen, and dining room. An additional Florida room adds a great peaceful reading room. All the of the main rooms have tall ceiling which provide open feel and lots of natural lite from the upper windows. Bedrooms are spilt plan, main bedroom is on ground floor with 10 ft ceiling. Great location.. this lot, offers a generous outdoor area where you can relax and take in the lush landscaping front and back The attached private one-car garage provides ample storage space, with easy access to the washer and dryer for added convenience. Home offers gas stove, gas water heater and gas heater. Community offers amenities including the pool and tennis courts, enhancing your lifestyle. Sellers offer possible concessions for loan buy-down or closing costs. See today! Seller offering possible concessions for closing costs and/or interest rate buy downs,

2365 Sierra Lane Unit 2365, Maitland

Courtesy of KIMBRIDGE REALTY, LLC

1951 Mohican Trail, Maitland
$925,000
5 Beds ⋅ 3 Baths ⋅ O6451533 MLS
Welcome to this charming five-bedroom, three-bath home on an oversized corner lot in the desirable Dommerich community! Featuring a versatile split-bedroom floor plan, an attached in-law suite with private entrance/own bath, and a private pool with a spacious backyard, this home combines comfortable living spaces with a location that makes everyday life convenient. Inside, engineered wood floors, wood blinds and crown molding add warmth and character throughout. The living room features a wood-burning brick fireplace, while the kitchen offers white cabinetry, granite countertops, stainless steel appliances and a farmhouse sink. The open kitchen and family room create a welcoming space for gathering and entertaining. The split-bedroom layout provides added privacy, while the attached in-law suite offers flexibility for multigenerational living, guests or a private retreat. Go outside to enjoy the fenced backyard and in-ground pool, ideal for relaxing and entertaining year-round. Updates include a 2023-roof, 2023 renovation (added third bath and in-law suite/flex space), 2026 new interior doors, 2026 new ceiling and insulation in garage, and 2026 updated landscaping. A rare feature in Dommerich, this home has natural gas service powering the water heater and furnace with additional opportunities to connect a gas range, dryer, outdoor grill, pool heater and more. Location is another standout feature. Directly across from a recreational and biking path providing access to Dommerich Elementary School and Maitland Middle School, this home offers a wonderful opportunity to enjoy the surrounding community and outdoor lifestyle. With easy access to downtown Maitland, Interstate 4, Maitland Community Park, Dommerich Elementary and Maitland Middle Schools, this home is must-see.

1951 Mohican Trail, Maitland

Courtesy of PREMIER SOTHEBY'S INTL. REALTY

1233 Wellington Terrace, Maitland
$1,139,500
4 Beds ⋅ 4 Baths ⋅ O6453544 MLS
Under contract-accepting backup offers. Nestled beneath a canopy of majestic oak trees in Maitland’s sought-after Wellington community, this beautifully maintained 4-bedroom, 3.5-bath residence offers 2,988 square feet of timeless architectural character, inviting living spaces, and glimpses of spring fed Lake of the Woods from both inside and outside the home. A sweeping circular driveway, manicured landscaping, and striking arched windows create an unforgettable first impression. Inside, a grand two-story foyer welcomes you with an elegant staircase and rich hardwood flooring, leading into thoughtfully designed spaces filled with natural light. The stunning living room is the architectural centerpiece of the home, featuring soaring vaulted ceilings with exposed wood detailing, a dramatic stone fireplace, custom built-ins, and an expansive arched window overlooking the beautifully landscaped grounds. A formal dining room with elegant millwork and built-in cabinetry provides a lovely setting for entertaining, while an adjoining open workspace offers flexibility for a home office or creative retreat. The spacious kitchen features white cabinetry, exotic natural stone countertops, generous preparation space, and a charming breakfast nook surrounded by windows. An additional living area opens directly to the pool and backyard, creating a natural extension of the home's gathering spaces. Currently enjoyed as a playroom, this versatile space can easily evolve with your family's changing needs, from a children's retreat to a game room, media lounge, or relaxed gathering space for years to come. Conveniently located on the main floor, the primary suite offers a peaceful retreat with abundant natural light, warm hardwood flooring, and an ensuite bathroom featuring dual vanities and a spacious walk-in shower. Three additional bedrooms upstairs provide comfortable accommodations and flexibility for family and guests. Step outside to discover a private backyard oasis featuring a sparkling pool, expansive lawn, mature landscaping, and multiple areas for outdoor dining, entertaining, or simply enjoying the Florida sunshine. A fully fenced backyard and two-car garage add everyday convenience, while the generous indoor and outdoor spaces create an inviting setting for everything from quiet afternoons to lively family gatherings. Residents of Wellington enjoy deeded access to Lake of the Woods, along with an exceptional location near highly regarded Seminole County schools, Winter Park’s charming Park Avenue, boutique shopping, and renowned restaurants. From peaceful mornings beneath the majestic oaks to beautiful sunsets over the neighborhood lake, this distinctive Maitland residence offers a wonderful balance of architectural charm, everyday comfort, and a place to grow and make memories for years to come.

1233 Wellington Terrace, Maitland

Courtesy of VYLLA HOME

1325 Lake Shadow Circle Unit 12103, Maitland
$199,000
2 Beds ⋅ 2 Baths ⋅ O6452783 MLS ⋅ 12 BLDG.
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

Courtesy of DALTON WADE INC

1741 Lyndale Boulevard, Maitland
$699,000
3 Beds ⋅ 2 Baths ⋅ O6453164 MLS
Virtually Staged. Less than a ten-minute drive from downtown Winter Park, Park Avenue’s shops and restaurants, and Rollins College, this completely renovated home has updates well beyond the finishes. Built in 1943 with solid block construction, it features new electrical, plumbing, central air conditioning, Jeld-Wen windows, and a tankless water heater. A wood-burning fireplace anchors the cozy living room, and the spacious renovated kitchen features white cabinetry, quartz countertops, stainless steel appliances, and a large island with seating for casual dining. The converted garage provides additional living space for a formal dining room or extra family room. Two secondary bedrooms share a renovated hall bathroom with a walk-in shower and rain showerhead. The spacious primary suite includes a custom walk-in closet and a renovated bathroom with double sinks, quartz countertops, and a walk-in shower with a rain showerhead. Sliding glass doors open from the suite to the back patio and fire pit area, with a huge backyard offering plenty of space for outdoor dining, entertaining, and play, plus room to explore adding a pool or expanding the home in the future. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School, this home puts some of the area’s favorite destinations close to home, including Lake Lily Park, Maitland’s cultural attractions, and the shops and dining along Park Avenue. Call today to schedule a private showing!

1741 Lyndale Boulevard, Maitland

Courtesy of FANNIE HILLMAN & ASSOCIATES

2312 Sierra Lane Unit 2312, Maitland
$349,600
2 Beds ⋅ 3 Baths ⋅ R4912215 MLS ⋅ 2312 BLDG.
Hidden Gem! This small community is quiet, independent, extremely well maintained and one of Maitland's most desirable communities. This unit is a spacious with two bedroom suites each with its own connected bathroom and an additional 1/2 bath four guest. Home is arranged with a separate dining room or office space, living room, kitchen and breakfast room. The kitchen is fully equipped with all appliances including a gas stove. There's also plenty of room with the breakfast nook which looks out onto the wooded back area. A wood-burning fireplace creates a warm, welcoming atmosphere that links the living room, kitchen, and dining room. An additional Florida room adds a great peaceful reading room .All the of the main rooms have tall ceiling which provide open feel and lots of natural lite from the upper windows. Bedrooms are spilt plan, main bedroom is on ground floor with 10 ft ceiling. Great location.. this lot, offers a generous outdoor area where you can relax and take in the lush landscaping front and back The attached private one-car garage provides ample storage space, with easy access to the washer and dryer for added convenience. Home offers gas stove, gas water heater and gas heater. Community offers amenities including the pool and tennis courts, enhancing your lifestyle. Sellers offer possible concessions for loan buy-down or closing costs. See today! New plumbing re-piped 2018, new roof 2018 new windows 2023, new Ac 2024 Cable and WIF provided by HOA.

2312 Sierra Lane Unit 2312, Maitland

Courtesy of KIMBRIDGE REALTY, LLC

989 Hamlet Court, Maitland
$299,999
3 Beds ⋅ 2 Baths ⋅ O6452476 MLS
An Inviting Retreat in a Prime Maitland Location!! Discover a home where comfort, charm, and convenience come together beautifully. This inviting 3-bedroom, 2-bathroom residence offers a welcoming atmosphere, thoughtfully designed spaces, and an exceptional location just 1.5 miles from Winter Park Village. Step inside to discover ceramic tile flooring throughout, creating a cohesive, timeless look while offering easy maintenance. Vaulted ceilings enhance the sense of openness, allowing the living spaces to feel bright and airy. Natural light fills the kitchen, where a charming dining area provides the perfect setting for leisurely breakfasts, morning coffee, or intimate gatherings with family and friends. Sliding glass doors extend the living space outdoors, offering easy access to the yard and creating a seamless connection between indoor comfort and outdoor enjoyment. The bedrooms are designed with everyday functionality in mind, with both the primary and secondary bedrooms featuring spacious walk-in closets for added storage. The primary suite offers a relaxing escape, complete with a private bathroom featuring a soothing garden tub and a separate walk-in shower—the perfect place to unwind and recharge. A convenient one-car garage adds another practical touch to this inviting home. A Location That Makes Every Day More Enjoyable One of this home's standout features is its desirable location. Just 1.5 miles from Winter Park Village, you'll be moments away from an exciting selection of boutiques, popular retailers, restaurants, cafés, and entertainment options. Whether you're planning a dinner out, browsing your favorite shops, or enjoying a casual afternoon close to home, this location puts the best of the surrounding area within easy reach. Combining comfortable living spaces, inviting natural light, and convenient access to local favorites, this property offers a wonderful opportunity to enjoy a lifestyle defined by both comfort and accessibility. Additional highlights include a 9-year-old roof and a low HOA fee, adding to the home's overall appeal. Comfortable living. A sought-after location. Everyday convenience.

989 Hamlet Court, Maitland

Courtesy of HOMESMART

1507 Grove Street, Maitland
$230,000
3 Beds ⋅ 2 Baths ⋅ O6452309 MLS ⋅ Park Lake Villas BLDG.
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

Courtesy of COLDWELL BANKER REALTY

1475 Lake Shadow Circle Unit 6205, Maitland
$199,900
2 Beds ⋅ 2 Baths ⋅ O6450405 MLS ⋅ 6 BLDG.
Step into easy, resort-style living in this beautifully updated 2-bedroom, 2-bathroom second-floor condo offering 1,048 square feet of thoughtfully designed space in the gated community of Visconti. With an open, light-filled floor plan and two spacious primary suites each with its own full bathroom this home delivers a flexible layout for everyday living. Luxury vinyl plank flooring runs throughout the entire home, giving every room a cohesive, modern look that's as durable as it is easy to maintain. The kitchen and living areas flow together seamlessly, creating a natural gathering space that keeps everyone connected, whether you're cooking dinner, watching a game, or settling in for the evening. Both suites are generously sized with ample closet space, and the split layout gives residents privacy when they want it. The bathrooms have been partially updated, offering a refreshed feel while leaving room to add your own finishing touches. Step outside to the large screened-in balcony a true extension of the living space, perfect for morning coffee, evening unwinding, or dining al fresco while overlooking the community's lush surroundings. The balcony also includes a dedicated storage area, keeping bikes, seasonal items, and outdoor gear neatly out of the way. A brand-new 2025 air conditioner adds comfort and peace of mind for years to come. The well-maintained, gated grounds feature mature landscaping and walking paths, along with a welcoming clubhouse for gatherings, two swimming pools for warm Florida afternoons, a fitness center for your daily workout, and tennis and basketball courts for friendly competition. HOA services cover water, sewer, pest control, and valet trash. Centrally located near shopping, dining, entertainment, and I-4, this condo offers easy access to Maitland, downtown Orlando, and area attractions. A great opportunity for low-maintenance living in a desirable Maitland location.

1475 Lake Shadow Circle Unit 6205, Maitland

Courtesy of CORCORAN PREMIER REALTY

151 Dommerich Drive, Maitland
$699,000
3 Beds ⋅ 2 Baths ⋅ O6451739 MLS
Under contract-accepting backup offers. Welcome to the desirable Dommerich Estates where timeless charm meets thoughtful modern updates. Completely renovated with an open-concept layout this home offers the kind of space and flow that makes everyday living and entertaining effortless. The heart of the home is the beautifully redesigned kitchen, featuring quartz countertops, island, solid wood cabinetry, and a full suite of stainless steel appliances including a wine refrigerator. Both bathrooms have been fully renovated with double vanities, designer finishes, shiplap accents, and a stunning primary bath complete with a frameless glass shower, marble tile, and marble countertops. The spacious primary suite also features a walk-in closet with custom built-in shelving. Natural light pours into the dining area through oversized windows that open to the backyard, creating a seamless indoor-outdoor connection. Step outside to a fully fenced backyard with a concrete patio that's perfect for grilling, relaxing, or hosting friends and family. The oversized two-car garage includes durable epoxy flooring, and a utility sink. Additional upgrades include a new water heater (2020). Location is just as impressive as the home itself. Zoned for the highly regarded Dommerich and Winter Park schools, you'll also enjoy neighborhood parks, walking trails, and community lake access and boat ramp just down the street. Homes like this don't come along often. Schedule your private showing today! The major updates have already been taken care of, new roof (2019) all-new windows (2019), a complete replumb (2019), LVT flooring throughout (2019), plus updated lighting and hardware in every room. New attic insulation 2022, all electrical outlets replaced 2022, new exterior outlets, termite protection system, Primary bedroom and guestroom closet built ins, new gutters 2021, new Carrier A/C (Garage and outdoor) 2021, new air ducts 2024, added air returns in rooms, new liftmaster garage door motors 2021, new driveway 2022, back patio resurface 2022, concrete side walkway and garbage pad 2022, rock walkway around house, exterior paint 2026, landscaping 2026

151 Dommerich Drive, Maitland

Courtesy of FANNIE HILLMAN & ASSOCIATES

1605 Grove Street Unit 550, Maitland
$200,000
3 Beds ⋅ 2 Baths ⋅ O6450169 MLS ⋅ Park Lake Villas BLDG.
Virtually Staged. Welcome to 1605 Grove Street! This single story unit offers a spacious and versatile floor plan, comfortable living areas, and the convenience of low maintenance living. Step inside to discover an open living and dining area with wood look flooring, plenty of natural light, and newer double pane windows and sliding glass doors, providing enhanced energy efficiency and comfort. The kitchen features white cabinetry, ample countertop space, a decorative tile backsplash, and a convenient pass through overlooking the main living area. Additional interior features include generously sized bedrooms, two full bathrooms, and an indoor laundry area. Step outside through the sliding glass doors to enjoy your own private, fenced patio, complete with brick pavers and room for outdoor seating. The community includes access to the community pool, insurance, exterior maintenance, grounds maintenance, and trash service, providing added convenience and helping simplify everyday living. Conveniently located in Maitland with easy access to shopping, dining, parks, major roadways, and the surrounding Winter Park and Orlando areas. Schedule your showing today!

1605 Grove Street Unit 550, Maitland

Courtesy of CREEGAN GROUP

1140 S Orlando Avenue Unit J12, Maitland
$225,000
2 Beds ⋅ 1 Baths ⋅ O6451478 MLS ⋅ J BLDG.
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

Courtesy of TARA MOORE REAL ESTATE

206 Quayside Cir Unit 203, Maitland
$950,000
2 Beds ⋅ 2 Baths ⋅ O6449915 MLS ⋅ Moorings On Lake Maitland BLDG.
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

Courtesy of PREMIER SOTHEBY'S INTL. REALTY

1909 Belford Court, Maitland
$1,429,900
4 Beds ⋅ 4 Baths ⋅ R4912181 MLS
Under contract-accepting backup offers. Welcome to 1909 Belford Court, a Mediterranean-style pool home in the highly desirable, guard-gated community of Maitland Club. Set on 0.37 acres with picturesque pond and fountain views, this four-bedroom, four-bath residence offers 4,230 square feet of living space and a two-car garage. An arched entry, mature landscaping, and palms create a welcoming first impression. Inside, tray ceilings, crown molding, plantation shutters, and extensive built-ins add character. The kitchen features abundant cabinetry, an island with seating, a bright bay-window breakfast nook, and a beverage bar with wine storage. Illuminated quartz in the kitchen and by the fireplace adds a distinctive touch. The primary suite offers a spa-like bathroom with a freestanding soaking tub, glass-enclosed shower, and gold-tone fixtures. A window-lined sunroom overlooks the private pool and pond, while the expansive paver patio, outdoor fireplace, and built-in seating create an inviting setting for entertaining. App-controlled low-voltage lighting adds ambiance after sunset. Recent upgrades include a new barrel tile roof installed approximately six months ago, new gutters, and a brand-new Trane HVAC system. Located just off I-4 at the Maitland exit, with downtown Orlando approximately seven-fifteen minutes away, this home combines Mediterranean charm with everyday convenience.

1909 Belford Court, Maitland

Courtesy of KORSHAK PROPERTY GROUP

1140 S Orlando Avenue Unit K15, Maitland
$420,000
2 Beds ⋅ 2 Baths ⋅ O6450713 MLS ⋅ K15 BLDG.
Winter Park Chain of Lakes Boat Slip Lease Included – Enjoy Boating Access with a Lease Paid in Full Through July 31, 2027, Transferable to the New Owner and Renewable! Experience the best of waterfront living at Lake Maitland Terrace with this beautifully renovated 2-bedroom, 1.5-bath condominium offering picturesque lake views, exceptional upgrades, and access to the renowned Winter Park Chain of Lakes. Imagine spending your weekends cruising the lakes, entertaining friends, or simply enjoying the waterfront lifestyle right outside your door. Inside, a sophisticated renovation brings modern elegance and functionality together. The beautifully updated kitchen features premium finishes, generous workspace, and a party-size ice maker, perfect for entertaining. The adjoining dining area offers abundant built-in storage, creating a seamless blend of style and practicality. Both bedrooms enjoy picturesque lake views, while the spacious primary suite features a walk-in closet and beautifully updated half bath. Step onto your screened front porch and take in the peaceful surroundings of this expansive lakefront community, featuring a sparkling swimming pool, fishing dock, putting green, and shuffleboard courts. Whether you're seeking a full-time residence or a seasonal retreat, this move-in-ready condominium delivers an exceptional combination of sophisticated interiors, waterfront amenities, and convenient access to one of Central Florida's most celebrated boating destinations. Your opportunity to embrace the Chain of Lakes lifestyle awaits!

1140 S Orlando Avenue Unit K15, Maitland

Courtesy of FANNIE HILLMAN & ASSOCIATES

2122 Korat Lane, Maitland
$385,000
4 Beds ⋅ 2 Baths ⋅ O6450101 MLS
Welcome to Winfield! This inviting home offers a thoughtful layout with comfortable spaces for relaxing, gathering, and entertaining. Step into a separate front living room, perfect for greeting guests or enjoying a quiet moment. The home flows into a beautiful kitchen featuring a breakfast bar and cozy dining area, with views into the family room to keep everyone connected. The split-bedroom floor plan provides a private primary suite on one side and two additional bedrooms on the other. The primary suite features an en-suite bathroom with a separate tub and shower. A versatile bonus room offers space for a home office, hobby room, or creative retreat. Step outside to a screened patio, ideal for shaded relaxation, overlooking a spacious backyard ready for weekend grilling and outdoor gatherings. Located in the desirable Winfield community, where HOA fees contribute to community exterior maintenance. This home offers convenient access to major roadways, including SR 434, SR 414, SR 429 and I-4 making commuting to Maitland, Altamonte Springs, Winter Park, and downtown Orlando more accessible. Enjoy convenient access to nearby destinations, including RDV Sportsplex, Maitland Business Center, Altamonte Mall, Wekiwa Springs State Park, and Trotters Park. With shopping, recreation, dining, and major commuter routes nearby, this Winfield home offers a convenient Central Florida lifestyle.

2122 Korat Lane, Maitland

Courtesy of MARK SPAIN REAL ESTATE

1020 Quinwood Lane, Maitland
$899,000
4 Beds ⋅ 2 Baths ⋅ O6449908 MLS
Under contract-accepting backup offers. Nestled in an established Maitland neighborhood on a lush quarter-acre lot, this beautifully renovated home offers an exceptional location just a short walk from Maitland Community Park. Thoughtfully reimagined through an extensive 2022 whole-house renovation, this 2,141-square-foot, four-bedroom, two-bathroom residence blends timeless design, modern functionality, and effortless flow. The desirable split-bedroom floor plan provides privacy and separation for the primary suite. Every detail has been carefully considered, from the light-toned, honey-oak solid hardwood floors that extend throughout the living spaces to the plantation shutters, vaulted ceilings, neutral paint palette, and smooth drywall finishes. Crown molding, updated baseboards, and thoughtfully selected finishes create a cohesive, elevated aesthetic throughout. At the heart of the home, the gourmet kitchen is an entertainer's dream, featuring custom white cabinetry, quartz countertops, a generous center island, and a separate peninsula offering abundant workspace and seating. New for 2026, the stainless steel refrigerator, dishwasher, and stove provide the latest updates to this beautifully renovated kitchen. The kitchen flows seamlessly into the dining and family rooms, where a wood-burning fireplace with an artistic surround and hearth creates an inviting focal point. A thoughtfully designed laundry and mudroom adds exceptional functionality with ample storage, a utility sink, and a spacious walk-in pantry. The primary suite offers a peaceful retreat filled with natural light and thoughtfully designed comforts. Custom closet systems provide exceptional organization, while motorized blinds add convenience and privacy. The spa-like en-suite bathroom features dual custom vanities and a beautifully appointed, glass-enclosed marble-tiled shower. Three additional bedrooms occupy a separate wing of the home, each featuring custom closet systems for effortless organization. The living experience extends outdoors to a private backyard retreat enclosed by eight-foot vinyl privacy fencing. A covered screened porch provides the perfect setting for relaxing or entertaining, while a charming brick courtyard with a pergola and custom gas firepit invites gatherings under the stars. Professional outdoor lighting enhances the landscaping and creates a welcoming atmosphere after sunset. Beyond its beautiful finishes, the home offers an impressive collection of modern upgrades and smart-home conveniences. A robust Ubiquiti network includes three Wi-Fi access points, hardwired Cat 6 connections in the office, and five exterior security cameras. Additional features include Nest smart thermostats and smart smoke detectors, motorized blinds in the primary suite, Yale smart locks, a hardwired ADT security system, Rachio Wi-Fi irrigation controls, roof 2018, HVAC 2016, and updated PEX plumbing. All windows and doors have been replaced, along with the garage door, further enhancing the home's comfort, functionality, and appeal. Ideally situated in Maitland, residents enjoy convenient access to established restaurants, neighborhood amenities, and beautiful parks. The home is zoned for Lake Sybelia Elementary, Maitland Middle, and Winter Park High School. Combining the character of an established neighborhood with the refined finishes and modern conveniences of an extensively renovated home, this exceptional property is truly move-in ready.

1020 Quinwood Lane, Maitland

Courtesy of PREMIER SOTHEBY'S INTL. REALTY

616 Lake Howell Road, Maitland
$550,000
4 Beds ⋅ 2 Baths ⋅ O6449406 MLS
Welcome to modern elegance in the heart of Maitland! This beautifully renovated home offers the perfect blend of timeless charm, contemporary finishes, and inviting living spaces. From the moment you arrive, you’ll be welcomed by a charming covered entryway featuring warm wood ceiling accents, and a beautiful sage green front door. Step inside to discover a bright, open atmosphere with gorgeous light wood flooring, fresh neutral tones, recessed lighting, and thoughtfully selected designer finishes throughout. The beautifully updated kitchen is a true showstopper, featuring warm wood cabinetry, Taj Mahal quartz countertops, elegant brass hardware, stainless steel appliances, a custom range hood, and a spacious peninsula with bar seating. Designed with both style and functionality in mind, this kitchen is perfect for entertaining and everyday living. The inviting living area features a stunning brick fireplace that adds warmth and character, while the beautifully updated bathrooms showcase modern vanities, stylish tile work, and sophisticated fixtures. The spacious bedrooms offer comfort and natural light, creating peaceful retreats throughout the home. Outside, enjoy a welcoming exterior, a spacious front yard, and an attached two car garage. Location, Location, Location! Ideally situated in the highly desirable Maitland area, this home offers convenient access to Winter Park, Downtown Orlando, shopping, dining, parks, and major roadways. With its beautiful renovations, modern finishes, and prime Central Florida location, this home is truly a must-see! Schedule your private showing today and experience everything this Maitland gem has to offer!

616 Lake Howell Road, Maitland

Courtesy of NETWORTH REALTY OF ORLANDO, LLC

140 Windglow Trail, Maitland
$910,000
4 Beds ⋅ 3 Baths ⋅ OM733685 MLS
Virtually Staged. New to the market, this amazing 2 story 4 bedroom and 3 bath Maitland home has just finished a full remodel! This home has an open floor plan which features classic elegant design style synonymous with Quarter Circle TO designs. Walking into the home, you will immediately notice the elegance. The whole home features luxurious wood style flooring, custom brick, and accent walls. All bathrooms feature waterfall showerheads and glass doors with gold finishes. The spacious and decked out kitchen features: White shaker cabinets, Quartz countertops, an island with a waterfall quartz counter top, double oven, modern cook top with stylish custom designed hood, farmhouse sink, touch screen WIFI refrigerator, wine rack, and gold hardware throughout. The spacious living room/dining room is great for hosting formal dinner parties or informal movie nights. The second living room is perfect for entertaining with a sliding glass door to the back yard and the bistro with 2 wine coolers nearby. The back yard boasts an oversized patio and a fire pit, which is fully fenced for privacy. There is an additional living room and space for an office on the second floor. This home showcases a beautiful staircase with tempered glass railings, motion sensor LED lighting up the stairs, and a 6 tier crystal chandelier. The Primary Suite features a walk-in closet and spa-like bathroom, highlights a modern bath tub, luxury shower containing waterfall and body shower heads. The fourth bedroom has French doors and its own entry to the incredible backyard. Easy access to lakes, restaurants, and shopping nearby. This home contains features of a million dollar home at this amazing price. This is a must see!

140 Windglow Trail, Maitland

Courtesy of ADDRESSUSA, INC

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 second 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

Courtesy of MIAMI TANGO INVESTMENTS REALTY

320 Alpine Drive, Maitland
$429,900
3 Beds ⋅ 2 Baths ⋅ O6446870 MLS
Under contract-accepting backup offers. Great Investor Opportunity in the Heart of Maitland & Surrounded by Beautifully Remodeled Homes and Ongoing Development. This Property Offers an Excellent Opportunity for Investors, Homeowners, or Buyers Looking to Rebuild the Property & be Part of an Area Experiencing Continued Improvement and Revitalization. The Location is Hard to Beat, Just Minutes from Top-Rated Schools, Popular Restaurants, Shopping, Downtown Orlando, Winter Park, And Major Highways Including I-4. With Neighboring Properties Being Upgraded and Continued Development Taking Place in the Area, this is an Excellent Opportunity to Invest in Maitland and Capitalize on the Area's Ongoing Transformation. Don't Miss the Opportunity to See This Property! Schedule Your Private Showing Today.

320 Alpine Drive, Maitland

Courtesy of OUTLET REALTY

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

Courtesy of SHAWFIELD REALTY GROUP

2514 Tuscarora Trail, Maitland
$899,000
4 Beds ⋅ 3 Baths ⋅ O6448334 MLS
$5000! CLOSING-COSTS CREDIT AVAILABLE! Qualified buyers who finance through the preferred lender may receive a $5,000 lender credit toward closing costs.Buyer must qualify;restrictions apply. 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, plus a bonus/flex room, 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 complete paid for 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 provide.

2514 Tuscarora Trail, Maitland

Courtesy of LPT REALTY, LLC

2141 Falkner Road, Maitland
$510,000
4 Beds ⋅ 3 Baths ⋅ S5159176 MLS
Discover the charm and convenience of Maitland living in this four-bedroom home featuring two full bathrooms and one half bathroom. A large, beautiful patio creates an inviting setting for outdoor dining, entertaining, or simply relaxing, while the fenced yard adds privacy and space to enjoy the outdoors. Newer roof, brand new flooring throughout. New Bathroom cabinetry. Interior and exterior new paint. Located at 2141 Falkner Road, this home offers the added convenience of I-4 just around the corner, making travel throughout Central Florida easy. Everyday essentials and local attractions are within approximately a seven-mile radius, including Publix at Gateway Crossing, nearby gas stations, and the restaurants and cafés of downtown Maitland’s Independence Lane and City Centre. Enjoy nearby Fennell Park, scenic Lake Lily Park, fitness and recreation at Genesis Orlando Sportsplex, and movies and dining at Enzian Theater and Eden Bar. AdventHealth Altamonte Springs also provides nearby access to hospital care. Sent from my iPhone

2141 Falkner Road, Maitland

Courtesy of HOME WISE REALTY GROUP, INC.

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

Courtesy of KELLY PRICE & COMPANY LLC

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

Courtesy of BECK REALTY LLC

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