Maitland FL Homes for Sale

2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Maitland's Hidden Gem! Discover comfort, style, and convenience in this BEAUTIFULLY MAINTAINED 2-bedroom, 1.5-bath condo in the desirable Park Lake Townhouses community of Maitland with NEW A/C 2026 and NEW Water Heater 2026. Located minutes from Park Ave, Trader Joes, Lifetime Fitness and all Winter Park/Maitland has to offer! Offering the FEEL OF A TOWNHOME with two spacious levels, a private patio, and a one-car garage, this home is tucked away in a QUIET LOCATION with PEACEFUL GREEN SPACE VIEWS from the front. Step inside to find EASY-CARE TILE FLOORING throughout the main level and a bright, welcoming Living Room filled with NATURAL LIGHT from the large front window. A convenient half bath and SPACIOUS CLOSET are located just off the hallway before the home opens into the Dining and Kitchen areas. Perfect for both everyday living and entertaining, the Dining area features sliding glass doors leading to a PRIVATE FENCED PATIO, creating a wonderful outdoor space for morning coffee, grilling, or relaxing evenings. The patio also provides direct access to the ATTACHED ONE-CAR GARAGE. Just off the Dining area, you'll find a DEDICATED LAUNDRY ROOM complete with an included washer and dryer. The beautiful Kitchen is sure to impress with its abundance of cabinetry, GRANITE COUNTERTOPS, stainless steel appliances, CHIC TILE BACKSPLASH, and center island that adds both functionality and style. Upstairs, two generously sized bedrooms provide comfortable retreats. The Primary Bedroom features ATTRACTIVE HARDWOOD FLOORING, while the second bedroom is carpeted for added comfort. Both bedrooms offer DOUBLE MIRRORED CLOSET DOORS and share a well-appointed en suite bath. FROSTED GLASS-PANELED INTERIOR DOORS throughout the home add a modern and distinctive touch. Adding even more value and peace of mind, the home features a NEW AC SYSTEM and NEW WATER HEATER. Residents of Park Lake Townhouses enjoy a SPARKLING COMMUNITY POOL along with HOA-covered trash collection, lawn care and exterior maintenance, including the roof, making for a LOW-MAINTENANCE LIFESTYLE. Ideally located, you're just minutes from the boutiques, restaurants, and cafés of PARK AVENUE IN WINTER PARK, as well as CULTURAL DESTINATIONS such as Rollins College, Morse Museum of American Art, and Winter Park Scenic Boat Tour. Nearby shopping, dining, and entertainment options abound at MAITLAND CITY CENTRE, while commuters will appreciate EASY ACCESS to I-4, SR 414, and downtown Orlando. With its STYLISH UPDATES, private outdoor space, attached garage access, and EXCEPTIONAL LOCATION near some of Central Florida's most beloved destinations, this CHARMING residence is ready to welcome you home. Act quickly—this GEM won't last long!

892 Park Lake Circle Unit 69, Maitland

$415,000

4 Beds ⋅ 2 Baths ⋅ Indian Hills Unit 1 Rep SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Discover a beautifully transformed 4-bedroom, 2-bath Maitland gem, a turnkey showpiece that blends modern style, smart upgrades, and undeniable curb appeal. The home greets you with a fresh look, mature landscaping, manicured hedges, and a custom front deck with modern horizontal railing, creating a welcoming entry and the perfect spot to enjoy your morning coffee. Step inside to an open and airy layout with abundant natural light, wood-look flooring, updated lighting fixtures, and multiple living areas ideal for both everyday living and entertaining. The renovated kitchen features white shaker cabinetry, modern countertops, stylish backsplash details, stainless steel appliances, and ample cabinet space. The dishwasher and oven were recently updated between 2022 and 2024. The kitchen flows seamlessly into the dining and living areas, creating a functional and inviting layout. The home offers spacious bedrooms along with versatile flex spaces perfect for a home office, guest room, or additional living area. The primary suite includes an updated ensuite bathroom with a glass-enclosed walk-in shower and a custom-designed primary closet with built-in organization. Out back, enjoy a fully refreshed backyard featuring brand new sod, a brand new paver patio, and a covered, screened back porch ideal for relaxing or entertaining year-round. Additional upgrades include a brand new driveway, solar panels for energy efficiency (to be paid off in full by the sellers at closing upon an accepted offer), smart home features, updated bathrooms, and modern finishes throughout. Adding to the appeal, HOA membership is optional, offering buyers the freedom of homeownership without mandatory HOA dues or restrictions. Conveniently located near shopping, dining, parks, and major roadways, this beautifully maintained Maitland home combines comfort, functionality, and contemporary style in one of Central Florida's most desirable communities.

1327 Chipola Trail, Maitland

$355,000

4 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code

All roads lead to Visconti East! Located in Maitland, bordering nearby scenic Winter Park (Park Ave./ Rollins College) this distinctive 3 story, 4 Bed/2.5 Bath townhome is situated directly off of I-4 and SR414, within 10 minutes to Downtown Orlando, Park Avenue, and close access to SR429, Winter Garden, and North Orlando. This home offers a one-of-a-kind floor plan with the entry foyer, hall closet, half bath and uniquely set up two car garage on the first floor, living room/kitchen + primary bedroom/bath on the second floor, and 3 bedrooms/ full bathroom, large hallway closet on the third level. All bedrooms feature spacious walk-in closets. Situated next to two fountain ponds that are overlooked from both sides of the unit on 2nd/3rd floors. No need to worry about additional projects, this very special and unique townhouse is move-in ready with top-quality updated features and architectural design, including imported Bianca Antico granite countertops, Italian travertine flooring and showers, stylish arches, and a massive built in bookcase. Shopping, Entertainment and Major Retail are all within miles, including downtown Maitland and Winter Park Village. Premier luxury gyms Genesis Health Club and Lifetime Fitness minutes away for ice skating, pickleball, aquatics and wellness community. Beautiful and safe bike trails accessible just by a short walk/ride. Come see all that this home and community has to offer! Call today for your private showing!

2401 Legacy Lake Drive Unit 2401, Maitland

$975,000

3 Beds ⋅ 3 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code

Located in a premier Maitland neighborhood, 119 Hollie Ct presents a rare opportunity to own a beautifully maintained home in an established pocket community where properties seldom come on the market. This secluded one-level residence sits on a private lot and includes deeded access to the neighborhood boat ramp and the renowned Chain of Lakes, bringing waterfront recreation within easy reach. Inside, you will find 2,192 square feet of bright and inviting living space across 3 bedrooms and 3 bathrooms. The kitchen opens directly into the gathering room, where a cozy fireplace creates a warm focal point for relaxing or hosting friends and family. An adjoining sunroom takes full advantage of the home's southern exposure, filling the interior with natural light throughout the day and adding a cheerful energy to everyday living. The split floor plan is designed with privacy in mind. The oversized primary suite occupies one side of the home and features a large ensuite bathroom with double sinks, a separate shower, and a soaking tub for those well-deserved moments of relaxation. On the opposite side, two additional bedroom suites provide comfortable and independent spaces for family members or visiting guests. A small bonus area adds welcome flexibility, serving nicely as a home office, hobby room, or creative studio. Outside, the backyard offers a true personal retreat. A sparkling pool and a terrace shaded by a beautiful pergola create the perfect setting for entertaining outdoors or simply unwinding in peace. The seamless blend of indoor and outdoor spaces makes this home ideal for the Florida lifestyle. Beyond the property itself, the location delivers everyday convenience with easy access to shopping, restaurants, theme parks, major roads, and the airport. You get the best of quiet suburban living without sacrificing proximity to everything Central Florida has to offer. Homes in this neighborhood rarely become available, making this a truly unique opportunity. Schedule your private showing today and see everything this special property has to offer before it is gone.

119 Hollie Court, Maitland

$1,995,000

4 Beds ⋅ 4 Baths ⋅ Kings Row SubDv. ⋅ 32751 Zip Code

Welcome to 220 Adams Drive — a breathtaking, completely remodeled single-story masterpiece nestled in the heart of Maitland's coveted Kings Row neighborhood. Thoughtfully reimagined from the studs out with exquisite craftsmanship and elevated design, this stunning home offers 4 bedrooms, a dedicated private office, 3.5 baths, and over 3,000 square feet of refined living on a fully fenced, oversized lot. The renovation is truly comprehensive — all-new plumbing, electrical, ductwork, and three separate AC units provide complete peace of mind. Spray foam insulation delivers exceptional energy efficiency, propane gas powers the chef's kitchen cooktop and tankless hot water heater, and Lutron touch-slide dimmers indoors plus automated Lutron outdoor lighting give the home a level of sophistication and control that is rarely found at any price. French drains round out a property that has been engineered as thoughtfully as it has been finished. Step through a charming covered front porch and into a bright, open-concept interior where elevated ceilings, rich wood floors, and designer recessed lighting create an effortlessly elegant atmosphere. The chef's kitchen is a showstopper — outfitted with high-end appliances including a gas cooktop, custom white cabinetry, clever appliance garages, and bespoke built-ins that marry beauty with function. The warm and inviting living room anchors the home with a wood-burning fireplace and seamless sliding doors to the pool beyond. The split-bedroom layout offers exceptional privacy for every member of the household. The oversized primary suite features a spa-inspired en suite with a double-sink vanity, walk-in glass shower, and soaking tub — plus a large walk-in closet with custom built-ins. The second bedroom enjoys its own private en suite with a walk-in shower, perfect for guests or multi-generational living. Bedrooms three and four share a well-appointed hall bath with a tub/shower combination. Outside, your private resort awaits. The saltwater pool with sunshelf is the perfect centerpiece, framed by a covered cabana with fireplace and a fully equipped outdoor kitchen. The Lutron automated lighting system extends seamlessly to the exterior, creating effortless ambiance day and night. The fully fenced yard offers privacy and room to breathe. The property features a two-car garage and a separate one-car garage — both finished with epoxy floors. The one-car garage is currently appointed as a private home gym with an adjacent storage room, offering flexible utility from day one. Located in a quiet, tucked-away neighborhood with a community park and playground, this home is just minutes from Winter Park, Park Avenue, the Winter Park Racquet Club, and scenic parks and trails. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High School. Homes of this caliber — fully rebuilt, impeccably finished, with every system new — are extraordinarily rare. Schedule your private showing today.

220 Adams Drive, Maitland

$410,000

3 Beds ⋅ 2 Baths ⋅ Pindar Sub SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Every detail of this home was thoughtfully curated to offer timeless beauty, upscale finishes, and modern functionality. This exceptional property blends contemporary design with everyday comfort, creating the perfect living experiences. The oversized walk-in shower creates a true resort-style experience with floor-to-ceiling marble-inspired tile, frameless glass enclosure, rainfall showerhead, and designer pebble stone flooring that adds texture and tranquility. Natural light pours through the window, enhancing the bright, airy atmosphere while highlighting the glossy porcelain tile floors that flow seamlessly throughout the space. lastly this home has the perfect blend of modern elegance and functionality in this beautifully designed gourmet kitchen. Featuring stunning granite countertops, sleek custom gray shaker cabinetry, and premium stainless-steel appliances, this space was crafted with both style and everyday living in mind.

200 Moseley Avenue, Maitland

$231,000

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

$719,990

3 Beds ⋅ 2 Baths ⋅ Dixie Terrace SubDv. ⋅ 32751 Zip Code

Charming Newly Renovated Bungalow in Prime Maitland Location – Move-In Ready with Endless Potential! Discover this beautifully updated 3-bedroom, 2-bath bungalow at 1741 Lyndale Blvd, Maitland, FL 32751 – perfectly positioned on the edge of Winter Park for an unbeatable blend of tranquility and convenience. Freshly renovated and move-in ready, this home offers immediate comfort while situated in a sought-after neighborhood where many properties are being transformed into spacious, high-end residences. It's an ideal opportunity to enjoy modern luxury today and customize further tomorrow in one of Maitland's most desirable areas. Step into a bright, open floor plan where the family room integrates effortlessly with the dining area, anchored by a cozy fireplace – perfect for gatherings. The heart of the home is the fully renovated kitchen, featuring abundant cabinetry, sleek quartz countertops, and a large kitchen island with seating for four at the breakfast bar – ideal for casual meals or entertaining. Spacious primary suite with a custom walk-in closet and sliding doors opening to the back patio and fire pit area –your private oasis for relaxing in the backyard. The en-suite primary bathroom boasts dual sinks, quartz counters, and a walk-in shower with a nice rain showerhead. Two generously sized secondary bedrooms with ample closet space, sharing a beautifully updated hall bathroom with another walk-in shower and rain showerhead. Brand-new Jeld-Wen windows, updated water and electrical systems, new tankless water heater, and new efficient central A/C system. Luxury vinyl plank flooring flows seamlessly through the entire home, delivering durability and style. Nestled in a peaceful, family-friendly neighborhood, this home offers quick access to top-rated Orange County schools, including nearby Dommerich Elementary and strong feeders to Maitland Middle and Winter Park High. Enjoy a short drive or easy stroll to Scenic Lake Lily Park, with walking trails, picnic spots, playgrounds, and charming events; Maitland's vibrant cultural scene; excellent dining options; Premier golfcourses, boutique shopping, and the upscale charm of Park Avenue in Winter Park; and convenient proximity to major Orlando attractions, themeparks, airports, and employment hubs – all while enjoying Maitland's quiet, tree-lined streets. This move-in-ready gem combines modern finishes with tremendous upside in a rapidly appreciating location. Don't miss your chance to own in one of Central Florida's most desirable pockets!

1741 Lyndale Boulevard, Maitland

$1,149,900

4 Beds ⋅ 5 Baths ⋅ Terra Place SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Virtually Staged. Private Pool Retreat with Two Primary Suites in Terra Place. Nestled in Terra Place, one of Maitland’s best-kept-secret neighborhoods, where every street ends in a cul-de-sac and a community park is just steps away, this custom one-story pool home offers space, privacy, and functionality—with no mandatory HOA. Soaring cathedral ceilings, including in the kitchen, and an abundance of windows fill the home with natural light. The open-concept layout flows seamlessly between the kitchen, dining, and living spaces, making everyday living and entertaining effortless. At the center of the home, the spacious kitchen offers casual bar-top seating, stainless steel appliances including a GAS RANGE, and an abundance of storage and workspace for effortless everyday living and entertaining. The kitchen also enjoys direct views of the backyard, covered patio, and saltwater pool, offering the kind of sight lines families love and making hosting feel effortless. With TWO PRIMARY SUITES and a highly-desirable THREE-WAY SPLIT floor plan allowing for maximum privacy, EACH BEDROOM features its own ENSUITE BATH. The spacious primary retreat offers a spa-like bath experience with dual sinks, private water closet, a large shower and soaking tub under a perfectly placed window. Large-format tile and wood flooring throughout (no carpet), generous room sizes, and thoughtfully designed spaces provide a clean, timeless backdrop ready for your personal style. This north-facing property provides soft, steady natural light year-round to enjoy whether you're under the covered patio, playing with the pets in the fully fenced backyard, or posting up on the sun shelf in the saltwater pool. An oversized two-car garage with an epoxy floor and mini split AC unit, NEW ROOF (2026) and SMART HOME (All Lutron light switches/fans, smart thermostats, door locks, alarm, and cameras) features add even more value and peace of mind. Boat Parking on the right side of the home through the double gate can accommodate all of your recreational vehicles. Enjoy walking or biking to Maitland Community Park, a 25-acre wooded park with tennis courts, basketball courts, playgrounds, trails, and pavilions. Conveniently located just minutes from downtown Maitland, Park Avenue in Winter Park, downtown Orlando, major roadways, area hospitals, and both executive and international airports. Zoned for highly regarded Lake Sybelia Elementary, Maitland Middle, and Winter Park High School, this exceptional home is a rare opportunity in one of Maitland’s most secluded and desirable neighborhoods. Call today for your private showing.

766 Terra Place, Maitland

$2,999,000

6 Beds ⋅ 5 Baths ⋅ Lake Sybelia Shores SubDv. ⋅ 32751 Zip Code

Welcome to luxury lakefront living at its absolute finest in the heart of Maitland, Florida. Nestled along the pristine shores of Lake Sybelia, this extraordinary three-story estate offers an unparalleled combination of elegance, comfort, and breathtaking waterfront views. Boasting 5,355 square feet of thoughtfully designed living space, this stunning residence features six spacious bedrooms, four and a half bathrooms, and an open-concept floor plan perfectly crafted for both entertaining and everyday living. Expansive walls of glass fill the home with natural light while showcasing panoramic lake views from nearly every room. The main living area seamlessly connects the gourmet kitchen, dining room, living room, and family room, all overlooking the sparkling waters of skiable Lake Sybelia. Designed with indoor-outdoor living in mind, each floor features a balcony spanning the entire width of the rear of the home, creating multiple spaces to relax and enjoy Florida’s spectacular sunsets. Step outside to your private resort-style oasis complete with a gorgeous pool, lush landscaping, and direct lake access with your own private boat dock and lift, perfect for boating, skiing, and waterfront recreation year-round. The upstairs retreat is anchored by an impressive primary suite featuring serene lake views and private balcony access. The upper level also includes a dedicated private office, ideal for working from home while enjoying stunning lakefront views. Two additional bedrooms share a beautifully designed Jack-and-Jill bathroom, while another flexible bedroom space can easily serve as a nursery, fitness room, or additional guest bedroom. Every level of the home has been carefully designed to maximize comfort, privacy, and functionality while maintaining a sophisticated and timeless aesthetic throughout. The lower level offers endless entertainment possibilities with a spacious game room, a full movie theatre, an additional guest bedroom, and a full bathroom ideal for visitors or multi-generational living. Completing this exceptional property is a beautiful temperature controlled wine cellar holding almost 2,000 wine bottles, a two-car garage with additional storage space, a large home generator, and countless luxury details throughout. This one-of-a-kind Lake Sybelia estate delivers the perfect balance of upscale living, modern convenience, and the ultimate waterfront lifestyle in one of Central Florida’s most desirable locations.

1166 N Lake Sybelia, Maitland

$765,000

4 Beds ⋅ 2 Baths ⋅ Maitland Woods SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Don't miss this rare opportunity to purchase your dream home in the established Maitland Woods neighborhood. This charming 4-bedroom, 2-bath home has been meticulously maintained and contains premium finishes throughout. The open floor plan includes a large family/great room, dining room, and an enclosed patio, perfect for entertaining. The updated kitchen features a handmade subway tile backsplash, quartzite countertops, stainless steel appliances, a coffee bar, and a versatile indoor laundry/ second office or crafting room. The primary bathroom has been completely renovated, with a double-sink marble vanity, large shower, and walk-in closet. The second full bathroom is centrally located, with additional access to the enclosed patio, making it also an optional (future) pool bath. This home includes a large (0.29-acre) fully fenced backyard, ideal for children and/or pets to play. Some notable exterior improvements include: a new front brick patio, a new firepit area for entertaining, a vegetable/flower garden and beautiful landscaping. Maitland Woods is conveniently located near I-4, making commuting to either downtown Orlando or Lake Mary a breeze. In addition, the home is within walking distance to Orangewood Christian School, Lake Sybelia Elementary, the shops and restaurants of downtown Maitland (home of a weekly farmer’s market), city events at Lake Lily, and Lake Sybelia’s very own Homer Hough Park. Homer Hough Park is the area’s best-kept secret, with a playground, fishing, and pavilions for family events. This home will not last, call to schedule your private showing today! Age of major components includes water heater 2022; NEW front patio 2026; roof 2016; HVAC 2024/2025; Replumb CPVC 2020; inside and outside electrical panels 2025; and double-pane windows 2016-2023 – with lifetime warranty.

1191 Willowbrook Trail, Maitland

$519,000

3 Beds ⋅ 2 Baths ⋅ Druid Hills Estates 1st Add SubDv. ⋅ 32751 Zip Code

VIDEO/VIRTUAL TOUR AVAILABLE! This Maitland pool home features 3 bed/2 bath in the main house with a 4th room addition on the other side of the garage. The 4th room has it's own separate entrance and it's own rear door access to the pool! Use it as a home office, creative studio, home gym, or income-producing suite — with no HOA to answer to. The cozy fireplace, hardwood floors, and split bedroom floor plan makes it feel like home. The oversized rectangular pool and deck were recently resurfaced and a screen enclosure was added to make maintenance a breeze. There’s still plenty of backyard space to enjoy on the huge 0.28 acre lot equipped with a white vinyl fence and storage shed. Minutes from excellent Maitland private schools and the Winter Park private school corridor, you’ll love the area! It’s close to Trader Joe’s, Winter Park Shopping & Dining, Audubon Center for Birds of Prey, Maitland Art Center, Lake Lily Park, and Enzian Theater. The RDV Sportsplex Athletic Club — with 400+ monthly classes — is an incredible convenience as well! Highway I-4 is close by and the SunRail Maitland Station is only 1 mile away, making downtown Orlando just 24 min commute on the Sunrail. Downtown Maitland is walkable with acclaimed restaurants anchored by a weekly Farmers' Market and the annual Jazz & Blues Festival. Roof is 2020, and water heater is brand new 2026. To see more of the house, WATCH THE VIDEO/VIRTUAL TOUR!

1065 Gregory Dr, Maitland

$520,000

4 Beds ⋅ 2 Baths ⋅ Druid Hills Estates 1st Add SubDv. ⋅ 32751 Zip Code

Nestled in the heart of highly desirable Maitland, this spacious 4-bedroom, 2-bath pool home offers the perfect blend of location, functionality, and outdoor living on an oversized .28-acre lot with more than 12,000 square feet of property. Surrounded by mature trees and established neighborhoods, this prime location places you just minutes from Downtown Maitland, Historic Winter Park, Downtown Orlando, world-class shopping, dining, entertainment, and Central Florida’s renowned attractions. Maitland is loved for its charming restaurants, weekend farmer’s market, beautiful lakes, and scenic tree-lined streets, all while bordering some of the most prestigious real estate in Central Florida.The backyard is truly the showstopper of this property, featuring a sparkling open pool, beautiful vinyl fencing, and an expansive yard that is far larger than many homes in the area. Recent landscaping enhancements include a hardscaped entertaining space and decorative stone half wall, creating the perfect setting for relaxing, hosting guests, or enjoying Florida outdoor living under the shade of the beautiful oak tree.Inside, the home features a desirable split-bedroom floor plan with formal living and dining rooms, plus a spacious family room offering plenty of flexibility for everyday living and entertaining. The galley-style kitchen is equipped with granite countertops and overlooks the living areas for easy functionality. Attractive laminate wood flooring and tile flow throughout the home, while all bedrooms have been updated with new ceiling fans. Additional improvements include electrical upgrades, new exterior doors, a new roof installed in 2020, and added attic insulation for enhanced energy efficiency. Built with sturdy concrete block construction, this home offers lasting durability and peace of mind. The indoor laundry room includes the washer and dryer for added convenience. This is a rare opportunity to own a pool home with a large backyard in one of Central Florida’s most established and desirable locations.

1010 Gregory Drive, Maitland

$325,000

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

One or more photo(s) has been virtually staged. Where Maitland's pristine waters meet a modern lifestyle! This luxury condominium in the coveted Lake Maitland Terrace community offers a rare blend of elegance and convenience on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Nestled among lush green spaces, this impeccably maintained mid-century modern complex boasts easy access to boutique shops, upscale dining, and vibrant entertainment. This unit stands out with its unique two-bedroom, one-and-a-half-bath layout—a rare find in the community, where most units are built with just one bath. Sunlight floods in through large windows, and warm wood floors flow throughout. This charming efficiently designed kitchen, with light cabinetry with contrasting hardware, quartz counters, and stainless steel appliances, is perfect for entertaining. Beyond the comforts of the home, enjoy the exclusive opportunity to secure a boat slip—a prized amenity in this tranquil lakeside retreat. Complex is amenity-rich with sidewalks, a community pool where residents enjoy lake access with beautiful views. The amenities include a clubhouse with a full kitchen, kayak racks, a fishing pier, and a personal storage unit. Walk to Lake Lily Park’s events, the Enzian Theater, and be just minutes from Winter Park Village and Park Avenue. Zoned for top-rated schools—Dommerich Elementary, Maitland Middle, and Winter Park High—this is a chance to embrace the best of Maitland living. Don’t miss your chance to claim this exceptional retreat as your own.

1140 S Orlando Avenue Unit I14, Maitland

$1,499,000

5 Beds ⋅ 3 Baths ⋅ Ravndals Rep SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Tucked between the shores of Lake Nina and Lake Maitland, this beautifully reimagined California ranch blends modern design with effortless everyday living in one of Maitland’s most desirable locations. Completely remodeled in 2022, the home showcases a fresh, sophisticated aesthetic with thoughtfully curated finishes throughout. The light-filled interior offers seamless flow between living spaces, combining clean modern lines with warm, inviting character. The renovated kitchen features a brand-new range, oven, and microwave, creating a stylish and functional centerpiece for both entertaining and daily life. Custom closets throughout the home provide elevated organization and exceptional storage. In addition to the main living areas, a spacious bonus room offers incredible flexibility and can easily function as a second family room, home office, fitness studio, playroom, or media space to fit your lifestyle needs. Step outside to a private backyard retreat designed for entertaining, complete with a sparkling pool, expansive outdoor living space, and plenty of room for gatherings, dining, and relaxing under the Florida sunshine. The indoor-outdoor flow perfectly captures the essence of California-inspired living. Ideally positioned in a picturesque pocket of Maitland between two beautiful lakes, this home also benefits from zoning for top-rated schools while offering convenient access to dining, shopping, parks, and major roadways. A rare opportunity to enjoy modern California-inspired living in an exceptional location.

541 Manor Road, Maitland

$700,000

3 Beds ⋅ 2 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code

Located in the sought after Dommerich neighborhood, this beautifully maintained pool home is just a short walk to Dommerich Elementary and Maitland Middle School. Hardwood floors and an open floor plan create an easy flow for everyday living and entertaining, centered around a spacious kitchen with a gas range, breakfast bar, and generous gathering space. Additional features include a wood burning fireplace and an indoor laundry room. Major updates provide peace of mind, including a roof replaced four years ago, a six year old HVAC system, a water heater less than one year old, updated electrical and plumbing completed during the 2010 renovation, and a whole house generator powered by a 500 gallon propane tank. Outside, enjoy a large backyard with a pool, heated spa, and plenty of room to entertain, while a welcoming covered front porch with pavers and a tongue and groove ceiling adds warmth and curb appeal.

703 Nicoma Trail, Maitland

$215,000

2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Virtually Staged. Resort-style amenities, low-maintenance living at a reasonable price, and a move-in ready home come together at 1927 Legacy Cove in beautiful Maitland. As you approach this GATED COMMUNITY, you will feel at ease with the added layer of security. Parking at the condo, you will see an extremely rare feature - an ATTACHED 2 CAR GARAGE! Inside, your eyes will be immediately drawn to the kitchen features: NEW STONE COUNTERTOPS, updated cabinets, STAINLESS STEEL APPLIANCES, pantry, tile backsplash, and breakfast bar. FRESH INTERIOR PAINT and tall ceilings throughout the home give it a clean, bright feel. Laminate floors and crown molding give the main living spaces a special touch. Upstairs, you will find NEW CARPET and a walk-in closet in both bedrooms. The conveniently-located 2nd floor laundry area is situated near the main bedrooms for everyday ease. The HOA provides exceptional value with a comparatively low monthly fee that includes: water/sewer, concierge trash pickup, and exterior maintenance, and resort-style amenities including a gorgeous COMMUNITY POOL, fitness center, clubhouse, playground, a basketball court, fishing pier, and tennis courts. They also just replaced the roof on this building within the last year or so. Conveniently located less than 1.5 miles from I-4 and approx 1 mile from SR-414, this home offers easy access throughout Greater Orlando. Historic Park Avenue in Winter Park is just 5 miles away, and Lake Eola in Downtown Orlando is approx 8 miles away. Altamonte Mall, multiple hospitals, Seminole State College, Rollins College, and even Orlando’s famed theme parks are all within easy reach.

1927 Legacy Cove Drive Unit 1927, Maitland

$1,795,000

3 Beds ⋅ 3 Baths ⋅ Sheridan Place SubDv. ⋅ 32751 Zip Code

Welcome to an extraordinary lakefront sanctuary at 631 Lake Catherine Drive, where sophisticated luxury meets serene waterfront living in one of Maitland's most coveted locations. This meticulously renovated residence, rebuilt down to the studs, represents the pinnacle of modern Florida elegance and is offered at $1,795,000. Positioned on an elevated lot overlooking the sparkling waters of Lake Catherine, this stunning home captures breathtaking lake views from nearly every room while offering the privacy and tranquility of a gated rear driveway accessible from a peaceful cul-de-sac. The heart of this home is the chef's kitchen, appointed with premium Cafe appliances, a Miele dishwasher, gleaming quartz countertops, and the convenience of a pot filler faucet. Expansive glass sliders seamlessly connect the kitchen to an inviting deck, creating the perfect setting for alfresco dining while drinking in panoramic lake vistas. The adjacent laundry room elevates everyday living with a built-in coffee bar and sink, transforming a functional space into a stylish amenity. Throughout the home, rich wood flooring flows beneath soaring vaulted ceilings accented by architectural beams, while recessed lighting and all-new windows bathe every corner in natural light. The luxurious primary suite offers a private retreat with its own mini-split system for personalized climate control, a spacious dressing room within the walk-in closet, and a spa-inspired ensuite bathroom featuring double vanities and a generous walk-in shower. Two additional well-appointed bedrooms provide flexibility, with the second bedroom boasting its own private ensuite with walk-in shower, while the third bedroom offers versatility as either a guest room or sophisticated home office. A third full bathroom in the hallway ensures comfort and convenience for family and guests alike. The attached garage has been thoughtfully enhanced with a dedicated gym area, while the exterior showcases fresh landscaping and a newer roof. Beyond the walls of this exceptional residence lies an equally impressive lifestyle. Zoned for the highly regarded Lake Sybelia Elementary and Maitland Middle Schools, this walkable community places you in close proximity to neighboring lakes and the charming ambiance of Lake Lily. Just ten minutes from Winter Park's iconic Park Avenue, residents enjoy effortless access to world-class shopping, dining, and cultural experiences. This is more than a home; it is a lifestyle of refined waterfront living where every detail has been carefully considered to create an absolutely stunning residence that must be experienced to be truly appreciated.

631 Lake Catherine Drive, Maitland

$439,000

3 Beds ⋅ 3 Baths ⋅ Brittany Gardens SubDv. ⋅ 32751 Zip Code

Location, Location, Location. Welcome to your new home in Maitland! This conviently located gated community home is a charming dwelling place featuring a cozy fireplace to uplift the ambiance of your living space. The home benefits from a tasteful neutral color paint scheme throughout, providing a welcoming canvas for your interior design aspirations. The kitchen is a cook's paradise, complete with a natural gas range, a stunning accent backsplash that truly makes the room pop and new applicances. Enjoy the luxury of a generous walk-in closet in the primary bedroom, perfect for all your storage needs. The primary bathroom offers the convenience of double sinks, making morning routines smooth and efficient. The shower in the primary bathroom add an opulent touch to your personal spa-like retreat. Relax or entertain with ease with a patio for outdoor gatherings. The fenced-in backyard promises privacy for all your outdoor activities. The home benefits from a newer roof, new AC, new hot water tank, ensuring peace of mind for years to come. The appeal of the property is enhanced by fresh interior paint and fresh exterior paint to the entire home. The comfort features continue with new flooring throughout, ensuring all areas of the home are updated. Take advantage of this home's remarkable attributes and turn this dwelling place into your personal sanctuary. Some pictures virtually staged.

499 Julian Lane, Maitland

$204,950

1 Beds ⋅ 1 Baths ⋅ Lake Maitland Terrace Apts SubDv. ⋅ 32751 Zip Code

PRICE IMPROVEMENT! Live the lake lifestyle in this beautifully updated 1-bedroom condo located in the iconic mid-century modern community of Lake Maitland Terrace. Completely refreshed in 2025, this first-floor residence features a brand-new HVAC system, new appliances including washer, dryer, and kitchen disposal, updated kitchen countertops, and new flooring throughout the living areas. Freshly painted and thoughtfully enhanced, the home blends timeless mid-century character with modern comfort and style. The spacious bedroom showcases sleek modern concrete flooring, adding to the authentic architectural aesthetic and contemporary feel. Perfectly positioned within a charming two-story mid-rise building, this residence offers effortless access to the community’s exceptional waterfront amenities and relaxed lakefront atmosphere. Set on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—residents enjoy direct lake access for boating, kayaking, canoeing, fishing, and water-skiing. A private community dock is located on-site, while the City of Maitland public boat ramp sits conveniently next door. Boat slips may also be available upon request. The location is truly unbeatable. Just one block from Lake Lily and Fort Maitland Park, and only minutes from Park Avenue, residents can walk to the Maitland Farmers Market, local restaurants, coffee shops, gym, dry cleaning, barber shop, boba tea, and more—all directly across the street. Enjoy easy biking access to Park Avenue for premier shopping, dining, and entertainment. Residents of Lake Maitland Terrace enjoy outstanding amenities including a newer community pool, lakefront clubhouse with breathtaking views available for private events, on-site laundry facilities, free unlimited water, and twice-weekly valet trash service. Experience maintenance-free living where iconic mid-century modern design meets modern updates and an unmatched Central Florida lakefront lifestyle.

1140 S Orlando Avenue Unit E2, Maitland

$899,000

5 Beds ⋅ 4 Baths ⋅ Forest Brook SubDv. ⋅ 32751 Zip Code

JUST REDUCED - Welcome to this meticulously updated, one-story masterpiece situated on a sprawling, professionally landscaped 1/3-acre lot. This 5-bedroom, 3.5-bath sanctuary plus bonus room seamlessly blends high-end design with modern efficiency. At the heart of the home lies an extra-large gourmet kitchen designed for the serious chef, featuring double ovens, dual microwaves, and two dishwashers. The culinary space flows effortlessly into an impressively large dining room, while the living room offers a cozy retreat centered around a classic wood-burning fireplace, perfect for crisp winter mornings. The interior has been refreshed with a brand-new neutral paint palette that complements the fully updated bathrooms and high-end finishes found throughout. Outside, the large fully fenced backyard serves as a private oasis, boasting a stunning pool and ample space for grand-scale entertaining. A massive storage shed, equivalent in size to a full garage bay, conveys with the property to provide incredible storage or workshop potential. This home offers ultimate peace of mind with significant mechanical upgrades, including a 2021 AC unit, 2019 water heater, 2013 roof, and a new pool pump, new interior doors throughout and new door hardware as well Also Plantation Shutters throughout. Sustainability meets savings with a solar panel system that slashes the electric bill to approximately $50 a month for this expansive home. Whether you are seeking a fabulous primary residence, vacation home or a high-performing investment property, that can also be rented as a short -term rental/Airbnb this is the home for you. Available furnished or unfurnished. Garage was converted to a bonus room and laundry with a ½ bath and a small second kitchen. It can easily be converted back to a garage. HUGE STORAGE SHED IN SIDE YARD EQUAL TO A ONE CAR GARAGE. Well water used for in ground sprinklers, a huge savings on your water bill. This rare find delivers the space, privacy, and modern luxury today’s buyers demand. Near everything including Whole Foods, Trader Joes, Great Winter Park- Park Ave Shopping, Dining and galleries.

614 Brookwood Lane, Maitland

$315,000

3 Beds ⋅ 2 Baths ⋅ Lake Faith Villas Condo SubDv. ⋅ 32751 Zip Code

One or more photo(s) has been virtually staged. Tucked away in this delightful and quiet lakefront community this beautifully renovated GROUND FLOOR condo offers so much, including a 2 PARKING SPACES - one is a deeded carport and the other is an open assigned parking spot... And there is a separate storage closet too! Situated on one level, this condo overlooks the charming grounds and a peek of Lake Faith from the living areas and porch. Inside is a treat for sure with a large open living and dining room layout that is light and bright. The unit has a luxury vinyl plank flooring throughout most of the unit and tile flooring in the kitchen and baths. The kitchen is updated with granite countertops and plenty of cabinetry. Off the living room is an expansive back porch that has tile flooring and was recently updated with newer windows and entry door (2024) .... And off the dining area is a charming, covered porch. So, lots of areas to enjoy day to day or if you like to entertain. The master bedroom is a spacious size and also opens to the back porch… You will love the master bath - completely redone with a large shower, a stylish vanity with ample storage as well as a make-up vanity and a generous walk-in closet. The 2 additional bedrooms are both a good size with great closet storage. Other notable features and updates are the inside laundry closet with open shelving and LG washer and dryer (2024) and the custom shades installed in the living areas and bedrooms (2023). Along with these upgrades, there have been system updates including hot water heater (2015) and AC (2016) as well as replumbed (2013) ... And HOA replaced the roofs in 2021! As well, they cover water, sewer and trash in your monthly fee. This complex offers a private, tranquil atmosphere and has terrific amenities including a gated entrance, clubhouse, and pool. And the location couldn’t be more convenient, with easy access to I-4 as well as a new retail and restaurant development within a short stroll. This is one not to miss!

249 W Lake Faith Drive Unit 205, Maitland

$139,900

2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code

Sought-after Visconti community of Maitland. The lowest 2-2 entry point currently available. This third-floor, 2-bed, 2-bath, 1,048 sqft condo features updated flooring, designer paint, LED lighting, new ceiling fans, updated faucets, and a screened patio with exterior storage. Community amenities include two pools overlooking Lake Shadow, tennis courts, lakeside walking paths, dog stations, and car wash stations, minutes to I-4, 429, downtown Orlando. Sold as-is, priced to sell.

1150 Lake Shadow Circle Unit 3304, Maitland

$850,000

5 Beds ⋅ 4 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code

Virtually Staged. Located in one of Maitland’s established and tree-lined communities, this distinctive Mid-Century Inspired Chalet residence offers exceptional space, dramatic design elements, and endless potential for modern transformation. Positioned within sought-after school district the home benefits from access to some of the area’s most well-regarded schools. The home’s impressive pavered approach sets the stage for its chalet-inspired architecture, where soaring A-frame rooflines, dramatic window walls, and natural stone detailing create an unforgettable presence beneath a canopy of mature trees — where “Colorado ski chalet meets Old Florida.” With 5 bedrooms and 3.5 bathrooms, the home is filled with high ceilings, expansive windows, and retro-inspired details that create character throughout. A striking open staircase with vintage styling showcases craftsmanship and design elements rarely found in today’s construction, while a massive paver courtyard welcomes guests and enhances the home’s unique indoor-outdoor lifestyle. Inside, the formal dining and sunken living room feature coffered ceilings and a dramatic circular brick fireplace centerpiece, while walls of windows flood the interiors with natural light. The spacious kitchen includes a cooking island, double wall ovens, closet pantry, breakfast nook, and an abundance of windows overlooking the private backyard area. Adding exceptional flexibility, the home also features a private in-law suite with its own separate entrance. The space includes a sleeping area, small seating/living space, private bathroom, kitchenette area with refrigerator and countertop workspace, and an eat-in area — ideal for multigenerational living, long-term guests, a private home office setup, or potential income-producing opportunities. The upstairs bedrooms open onto a rear balcony, creating a true retreat feel among the mature trees and landscaped surroundings. The primary bath features angular ceilings, oversized triangular windows, and a custom mosaic tile tub and double vanity that reflect the home’s original retro contemporary character. Outdoors, enjoy a sparkling swimming pool surrounded by shade trees, an expansive paver deck, and a fully fenced yard ideal for entertaining, gardening, or creating a private oasis. Recent updates include new roof 2024, along with a transferrable shingle warranty, both A/C HVAC units replaced 2019 and 2023, hot water heater was replaced in 2019, 2023 electrical work done, 2022 high end Samsung dishwasher installed, transferrable premium home appliance warranty expiring Feb 3 2027, gas-powered portable generator and underground utilities. This home presents an exciting opportunity for buyers seeking architectural character and the chance to personalize a spacious residence with cosmetic updates including flooring, wall finishes, and modern design enhancements. Conveniently located near top-rated dining, shopping, parks, and major commuter routes, Maitland remains one of Central Florida’s most desirable established communities, known for its timeless charm, mature landscapes, and exceptional location.

751 Sequoia Trail, Maitland

$645,000

3 Beds ⋅ 2 Baths ⋅ Greenwood Gardens Sec 02 Rep 01 SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Tucked away in the heart of Maitland, this thoughtfully updated three-bedroom, two bath residence blends everyday comfort with meaningful, modern upgrades. Freshly painted interior (June 2026) and a private spa pool WITH BRAND NEW POOL PUMP creates a serene outdoor retreat—perfect for unwinding or entertaining year-round in true Florida style. Inside, the home offers both function and peace of mind with a dedicated laundry room featuring a brand-new washer (2026) and newer dryer (2024). Major system updates have already been taken care of, including a new water heater (2025) and a recently installed HVAC system (April 2026), providing efficiency, reliability, and confidence from day one. Ideally located with close proximity to I-4 for easy commuting, and just a short walk to Maitland Community Park and Lake Lily, this home offers the perfect balance of convenience and lifestyle. A move-in-ready opportunity where the essential upgrades are already done for you.

910 Gamewell Avenue, Maitland

$550,000

3 Beds ⋅ 2 Baths ⋅ Druid Hills Ests SubDv. ⋅ 32751 Zip Code

Welcome to a rare opportunity in the beautiful neighborhood of Druid Hills in Maitland—this charming single-family home is on the market for the first time in 45 years. Built with solid block construction, this home offers exceptional durability, structural soundness, and reliable weather resistance, giving peace of mind for years to come. Situated on an expansive and highly desirable corner lot, the property provides a unique blend of privacy, space, and long-term potential. With .41 acres of land, this double lot offers endless possibilities, whether you’re looking to enjoy the generous yard or explore the option to split it into two separate parcels. Inside, the home features 3 bedrooms and 2 bathrooms across 1,623 square feet of thoughtfully designed living space. A spacious layout provides comfort and functionality, while large windows invite in natural light, creating a warm and welcoming atmosphere throughout. The 2-car garage offers ample storage and convenience, complementing the home’s practical appeal for everyday living. Outside, the oversized lot is truly the standout feature—lush, open, and full of potential for outdoor living, expansion, or future development. With its prime location, generous lot size, and first-time availability in decades, this is a one-of-a-kind opportunity you won’t want to miss.

9001 Lake Charity Drive, Maitland

$1,199,000

4 Beds ⋅ 4 Baths ⋅ Lake Sybelia Cove Ph 01 SubDv. ⋅ 32751 Zip Code

Now offered below recent appraised value, this exceptional residence combines luxury, location, and outstanding value in one of Maitland's most sought-after enclaves. Pride of ownership shines throughout this beautifully maintained original-owner home tucked away on a quiet cul-de-sac in the gated community of Sybelia Cove. Offering 4 bedrooms, 4 bathrooms, a side-entry 3-car garage, and 3,902 square feet, this spacious residence blends timeless design with thoughtful updates in one of Maitland’s most desirable locations. Inside, soaring ceilings and expansive windows fill the home with natural light, while the family room fireplace and wood flooring throughout the main entertaining spaces adds warmth and character. The functional floor plan features a private downstairs primary suite along with a dedicated office, creating flexibility for both everyday living and working from home. Upstairs, a spacious loft is accompanied by three additional bedrooms and bathrooms. Fresh carpeting in select areas enhances comfort throughout the home. The kitchen has been updated with refreshed cabinetry, countertops, and GE Café stainless steel appliances, flowing seamlessly into the main living spaces designed for entertaining and gathering. Step outside to a screened-in pool and outdoor living area designed for year-round enjoyment while taking advantage of breezes from nearby Lake Sybelia located just behind the home. A brand-new roof (2024) provides additional peace of mind. Located just moments from downtown Maitland’s shops, dining, and parks, this home offers the privacy of gated living with exceptional walkability and convenience. Call today for your private showing.

873 Cranes Court, Maitland

$239,900

3 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Beautifully well-maintained 3 bedroom, 2 bathroom condo located in the desirable Maitland area. This second floor unit features an updated kitchen, laminate flooring throughout, and an ope-concept layout that offers abundant natural light, including a bright and inviting porch space. The spacious primary-suite includes two walk-in closets. The communit offers a playground, fitness center, clubhouse a nice pool. Located closed to major roads and is walking distance to Publix, Starbucks and many other stores. Don't miss this exceptional opportunity!

444 Banyon Tree Circle Unit 202, Maitland

$549,000

5 Beds ⋅ 3 Baths ⋅ Northgate SubDv. ⋅ 32751 Zip Code

This AMAZING!, spacious 5-bedroom, 3-bath split-level home is located in a fantastic neighborhood and is packed with standout features. Upstairs, you’ll find beautiful engineered hardwood flooring throughout the main living areas, with carpet in the bedrooms and tile in the baths. A stunning screened-in porch overlooks the backyard and pool, offering a perfect spot to relax or entertain. The bright and airy formal living room provides plenty of space, while the dining room includes sliding doors that lead out to the porch. The large eat-in kitchen offers ample cabinet storage and even features a convenient pass-through window to the porch/outside bar—ideal for hosting. The upper level includes three bedrooms two bathrooms. Just a few steps down, the lower level opens to a massive family room with tile floors set to entertain family and friends with two additional bedrooms with carpet and a full bath. Tile flooring runs throughout this level. Additional highlights include outdoor spa , updated windows, a re-piped plumbing system, updated Electrical, and a well-maintained interior full of character. The home comes with paid in full solar panels and a Terminix termite bond and Well Maintained sprinkler system on well. Washer/Dryer are located in the garage. The garage include cabinets for additional storage. The yard features mature Citrus trees and Magnolia trees adding to the home’s charm. With its flexible layout, inviting screened porch, and beautiful salt water pool area, this home truly has it all.

1511 Glastonberry Road, Maitland

$215,000

2 Beds ⋅ 2 Baths ⋅ Park Lake Twnhs SubDv. ⋅ 32751 Zip Code

A beautiful affordable condo in Maitland. 2 bedrooms and 1 ½ baths with a 1 car garage. The kitchen has been updated with white cabinets and new counter tops. The appliances have been updated. There is a large dining room and separate living room. The utility room is on the 1st floor with an updated barn door for access. The 1st floor has wood flooring while the second floor has carpeting. The second floor has two bedrooms with an updated bathroom. The shower has been remodeled to allow easy access. This home has a large patio with artificial grass flooring. The one car garage is an added bonus. The property has had the window replaced, a new water heater (2026) and the electrical panel upgraded within the past couple of years. The A/C system was replaced in 2022. This wonderful unit is at a great price and will not last long.

814 Park Lake Circle Unit 8, Maitland

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