Homesinorlando.forsale Search Results

$425,000

Under contract-accepting backup offers. Welcome to Montacino at Enclave, Maitland—a peaceful, gated oasis where style, comfort, and convenience come together. This move-in-ready 3-bedroom, 2.5-bath townhome showcases timeless character, quality craftsmanship, and a premium location with no rear neighbors, offering tranquil, private views. The A/C system is less than one year old, providing added peace of mind. Inside, the open-concept living, dining, and kitchen area is perfect for entertaining, featuring beautiful ceramic tile flooring, elegant crown molding, and an abundance of natural light. Designer upgrades throughout—including updated lighting, mirrors, and hardware—create a refined, modern feel. Just off the kitchen, a covered rear patio overlooks a spacious, tree-lined green space that is fully maintained by the HOA, allowing you to enjoy the outdoors without the upkeep. The welcoming foyer is flanked by a convenient half bath on one side and access to the attached one-car garage on the other. Upstairs, the spacious primary suite has elegant wood flooring and features a private balcony, a generous walk-in closet, and a well-appointed en-suite bath. Two additional bedrooms, a full bathroom, and a laundry closet with built-in storage shelves complete the second floor, offering comfort and functionality for everyday living. Perfectly located just minutes from Downtown Orlando and Winter Park, this home offers the best of both worlds—easy access to shopping, dining, and entertainment while nestled in a serene lakeside community. Residents enjoy a resort-style pool, scenic sidewalks overlooking Lake Charity, and the security and convenience of low-maintenance living in a beautifully maintained gated neighborhood. This is your opportunity to enjoy resort-style living in one of Maitland's most desirable gated communities. (Attached to pics is additional info on HOA amount)

3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Welcome to Montacino at Enclave, Maitland—a peaceful, gated oasis where style, comfort, and convenience come together. This move-in-ready 3-bedroom, 2.5-bath townhome showcases timeless character, quality craftsmanship, and a premium location with no rear neighbors, offering tranquil, private views. The A/C system is less than one year old, providing added peace of mind. Inside, the open-concept living, dining, and kitchen area is perfect for entertaining, featuring beautiful ceramic tile flooring, elegant crown molding, and an abundance of natural light. Designer upgrades throughout—including updated lighting, mirrors, and hardware—create a refined, modern feel. Just off the kitchen, a covered rear patio overlooks a spacious, tree-lined green space that is fully maintained by the HOA, allowing you to enjoy the outdoors without the upkeep. The welcoming foyer is flanked by a convenient half bath on one side and access to the attached one-car garage on the other. Upstairs, the spacious primary suite has elegant wood flooring and features a private balcony, a generous walk-in closet, and a well-appointed en-suite bath. Two additional bedrooms, a full bathroom, and a laundry closet with built-in storage shelves complete the second floor, offering comfort and functionality for everyday living. Perfectly located just minutes from Downtown Orlando and Winter Park, this home offers the best of both worlds—easy access to shopping, dining, and entertainment while nestled in a serene lakeside community. Residents enjoy a resort-style pool, scenic sidewalks overlooking Lake Charity, and the security and convenience of low-maintenance living in a beautifully maintained gated neighborhood. This is your opportunity to enjoy resort-style living in one of Maitland's most desirable gated communities. (Attached to pics is additional info on HOA amount)

1395 Benevolent Street, Maitland

$975,000

Under contract-accepting backup offers. Built in 2020, this pristine townhome offers over 3,000 square feet of thoughtfully designed living space with NO HOA, two primary suites (one on each floor), 10-foot ceilings throughout, a private fully fenced backyard, and an unbeatable location just north of Park Avenue, tucked behind the Enzian Theater. Enjoy easy access to downtown Winter Park, Whole Foods, the recently revitalized Winter Park Village, Maitland, and Orlando. Designed for effortless, move-in-ready living, this modern 4-bedroom, 3.5-bath home features a spacious 2-car garage, abundant storage, and an ideal floor plan. The main level showcases distinctive stained and sealed concrete floors, while the open-concept living spaces are filled with natural light from 8-foot glass sliders overlooking the private backyard and patio. The beautifully appointed kitchen features white cabinetry extending to the 10-foot ceilings, granite countertops, a large center island, walk-in pantry, stainless steel appliances, a new Bosch dishwasher (Nov. 2024), a range, second built-in oven, and warming drawer. The adjoining dining and living areas are enhanced by a custom wood-plank accent wall and an open wood staircase. With over $60,000 in recent upgrades and improvements, this home has been thoughtfully enhanced with fresh interior paint, upgraded LED lighting and ceiling fans, custom accent walls, artificial turf, new gutters and drainage, UV window film, whole-house surge protection, an electric vehicle charging station, epoxy garage flooring, custom garage storage, and more. The first-floor primary suite offers two closets, including a walk-in closet and a second closet with washer/dryer hookups, plus a luxurious bath with a zero-entry glass shower and private water closet. Upstairs, a second primary suite features dual walk-in closets and a spacious bath, while two additional bedrooms, a full bath with dual sinks, a generous bonus room, and a large laundry room provide exceptional flexibility. Combining newer construction, quality upgrades, an exceptional floor plan, and a prime location, this move-in-ready home truly offers the best of low-maintenance living. Zoned for sought-after Dommerich Elementary, Maitland Middle School, and Winter Park High School.

4 Beds ⋅ 4 Baths ⋅ Coffins Sub SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Built in 2020, this pristine townhome offers over 3,000 square feet of thoughtfully designed living space with NO HOA, two primary suites (one on each floor), 10-foot ceilings throughout, a private fully fenced backyard, and an unbeatable location just north of Park Avenue, tucked behind the Enzian Theater. Enjoy easy access to downtown Winter Park, Whole Foods, the recently revitalized Winter Park Village, Maitland, and Orlando. Designed for effortless, move-in-ready living, this modern 4-bedroom, 3.5-bath home features a spacious 2-car garage, abundant storage, and an ideal floor plan. The main level showcases distinctive stained and sealed concrete floors, while the open-concept living spaces are filled with natural light from 8-foot glass sliders overlooking the private backyard and patio. The beautifully appointed kitchen features white cabinetry extending to the 10-foot ceilings, granite countertops, a large center island, walk-in pantry, stainless steel appliances, a new Bosch dishwasher (Nov. 2024), a range, second built-in oven, and warming drawer. The adjoining dining and living areas are enhanced by a custom wood-plank accent wall and an open wood staircase. With over $60,000 in recent upgrades and improvements, this home has been thoughtfully enhanced with fresh interior paint, upgraded LED lighting and ceiling fans, custom accent walls, artificial turf, new gutters and drainage, UV window film, whole-house surge protection, an electric vehicle charging station, epoxy garage flooring, custom garage storage, and more. The first-floor primary suite offers two closets, including a walk-in closet and a second closet with washer/dryer hookups, plus a luxurious bath with a zero-entry glass shower and private water closet. Upstairs, a second primary suite features dual walk-in closets and a spacious bath, while two additional bedrooms, a full bath with dual sinks, a generous bonus room, and a large laundry room provide exceptional flexibility. Combining newer construction, quality upgrades, an exceptional floor plan, and a prime location, this move-in-ready home truly offers the best of low-maintenance living. Zoned for sought-after Dommerich Elementary, Maitland Middle School, and Winter Park High School.

1424 Ridgewood Avenue, Maitland

$235,000

A rare 4 BR condo with A rated High School could be your next home. Visconti is a high end luxury community featuring a huge lakeside pool with beach entry, fitness center that rivals many commercial gyms, tennis courts, walking paths, and a fantastic clubhouse. The 2nd floor condo has an extremely functional layout that separates the master BR from the other 3 bedrooms. The kitchen is stunning with updated cabinets, solid surface counters and a gorgeous back splash. The common areas feature wood laminate floors with carpet in the bedrooms. Conveniently located in Maitland, this homes is just minutes away from restaurants, shops, I4, 414, and the Maitland business center. A fantastic choice for your main home, a 2nd home or an addition to a rental portfolio.

4 Beds ⋅ 2 Baths ⋅ Visconti West Condo SubDv. ⋅ 32751 Zip Code

A rare 4 BR condo with A rated High School could be your next home. Visconti is a high end luxury community featuring a huge lakeside pool with beach entry, fitness center that rivals many commercial gyms, tennis courts, walking paths, and a fantastic clubhouse. The 2nd floor condo has an extremely functional layout that separates the master BR from the other 3 bedrooms. The kitchen is stunning with updated cabinets, solid surface counters and a gorgeous back splash. The common areas feature wood laminate floors with carpet in the bedrooms. Conveniently located in Maitland, this homes is just minutes away from restaurants, shops, I4, 414, and the Maitland business center. A fantastic choice for your main home, a 2nd home or an addition to a rental portfolio.

1460 Lake Shadow Circle Unit 7207, Maitland

$195,900

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

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

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

1140 S Orlando Avenue Unit E11, Maitland

$140,000

Welcome to Carrington Park — one of Maitland’s most conveniently located communities! This ground-floor 2-bedroom, 2-bathroom condo offers 1,200+ square feet of comfortable living space at an unbeatable price point, making it an ideal primary residence or a smart addition to any investment portfolio.The open living and dining area flows naturally to a private screened patio perfect for enjoying Florida’s year-round weather without the bugs. Both bedrooms are generously sized, and the split-style layout offers privacy for owners and guests alike.Residents enjoy access to community amenities including a sparkling pool, fitness center, and more, all just steps from your front door. Situated at the corner of Howell Branch and SR-436, you’re minutes from shopping, dining, and major employers, with easy access to UCF, Full Sail, and Downtown Orlando.Whether you’re looking for a place to call home or a turnkey rental opportunity in a high-demand corridor, this one checks all the boxes. Priced at $140,000, schedule your showing before it’s gone.

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

Welcome to Carrington Park — one of Maitland’s most conveniently located communities! This ground-floor 2-bedroom, 2-bathroom condo offers 1,200+ square feet of comfortable living space at an unbeatable price point, making it an ideal primary residence or a smart addition to any investment portfolio.The open living and dining area flows naturally to a private screened patio perfect for enjoying Florida’s year-round weather without the bugs. Both bedrooms are generously sized, and the split-style layout offers privacy for owners and guests alike.Residents enjoy access to community amenities including a sparkling pool, fitness center, and more, all just steps from your front door. Situated at the corner of Howell Branch and SR-436, you’re minutes from shopping, dining, and major employers, with easy access to UCF, Full Sail, and Downtown Orlando.Whether you’re looking for a place to call home or a turnkey rental opportunity in a high-demand corridor, this one checks all the boxes. Priced at $140,000, schedule your showing before it’s gone.

2329 Coawood Unit 103, Maitland

$429,900

This beautifully positioned residence offers an open and inviting layout designed for easy living and entertaining. Enjoy peaceful water views of Lake Destiny with no rear neighbors, creating a private backdrop and a rare sense of space and tranquility. Whether relaxing indoors or stepping outside, the serene setting delivers a true sense of comfort and escape. The home also features a spacious 2-car garage, providing convenience and additional storage. Thoughtfully updated and move-in ready, this home offers valuable recent improvements including a new A/C unit (2022), water heater (2022), tile roof replacement (2022), updated paint and modern light fixtures (2023), and both bathrooms beautifully renovated in 2021. The kitchen is complemented by newer appliances, adding both style and functionality. Step outside and enjoy even more value with the outdoor deck currently being replaced, creating an enhanced outdoor living space to take in the beautiful lake setting. Residents enjoy access to exceptional community amenities including a pool, tennis courts, and access to Lake Destiny, all within a dog-friendly community designed to support an active and enjoyable lifestyle. Ideally located with quick access to major highways, dining, shopping, business centers, and everything Maitland and the greater Orlando area have to offer, this property delivers the perfect blend of lifestyle and accessibility. Whether enjoying your morning coffee overlooking Lake Destiny or coming home after a busy day, this residence offers the privacy, views, updates, and location today’s buyers are searching for.

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

This beautifully positioned residence offers an open and inviting layout designed for easy living and entertaining. Enjoy peaceful water views of Lake Destiny with no rear neighbors, creating a private backdrop and a rare sense of space and tranquility. Whether relaxing indoors or stepping outside, the serene setting delivers a true sense of comfort and escape. The home also features a spacious 2-car garage, providing convenience and additional storage. Thoughtfully updated and move-in ready, this home offers valuable recent improvements including a new A/C unit (2022), water heater (2022), tile roof replacement (2022), updated paint and modern light fixtures (2023), and both bathrooms beautifully renovated in 2021. The kitchen is complemented by newer appliances, adding both style and functionality. Step outside and enjoy even more value with the outdoor deck currently being replaced, creating an enhanced outdoor living space to take in the beautiful lake setting. Residents enjoy access to exceptional community amenities including a pool, tennis courts, and access to Lake Destiny, all within a dog-friendly community designed to support an active and enjoyable lifestyle. Ideally located with quick access to major highways, dining, shopping, business centers, and everything Maitland and the greater Orlando area have to offer, this property delivers the perfect blend of lifestyle and accessibility. Whether enjoying your morning coffee overlooking Lake Destiny or coming home after a busy day, this residence offers the privacy, views, updates, and location today’s buyers are searching for.

1010 Winderley Place Unit 149, Maitland

$1,499,000

Under contract-accepting backup offers. A premier street offering an accessible lifestyle to Maitland’s vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. Five bedrooms, four baths, stretching across 4,814 square feet with bonus space, there are many ways to make it your own. Inspired by classic Charleston architecture with Florida influences, the exterior features French doors across the front and rear elevations, lantern-style lighting and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters and upper-level balconies at both sides of home complete the design. Enter inside to a sweeping staircase with elegant iron details, with neutral travertine flooring that flows throughout the main level and finished with volume ceilings. The kitchen, living and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink and high-end stainless-steel appliances. Generous laundry and pantry storage are bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround-sound speakers and direct access to outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms, and the spacious primary retreat opens to a private balcony spanning across the back of home and with pool views. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light, and great closet storage and additional loft are a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining or a private workspace. Outdoor speaker system adds to the ambience. Additional improvements and features include a newer metal roof (2020), two HVACs (2021), water heater (tankless Rinnai installed by Maitland/Winter Park plumbing), plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and primary suite have ceiling-installed concert speakers and outdoor speakers. Lower-floor speakers have individual room controls and are served by a pantry stereo system. This exceptional home offers a desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a standout in one of Maitland’s special neighborhoods.

5 Beds ⋅ 4 Baths ⋅ Replat Blk B Poors Add SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. A premier street offering an accessible lifestyle to Maitland’s vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. Five bedrooms, four baths, stretching across 4,814 square feet with bonus space, there are many ways to make it your own. Inspired by classic Charleston architecture with Florida influences, the exterior features French doors across the front and rear elevations, lantern-style lighting and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters and upper-level balconies at both sides of home complete the design. Enter inside to a sweeping staircase with elegant iron details, with neutral travertine flooring that flows throughout the main level and finished with volume ceilings. The kitchen, living and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink and high-end stainless-steel appliances. Generous laundry and pantry storage are bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround-sound speakers and direct access to outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms, and the spacious primary retreat opens to a private balcony spanning across the back of home and with pool views. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light, and great closet storage and additional loft are a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining or a private workspace. Outdoor speaker system adds to the ambience. Additional improvements and features include a newer metal roof (2020), two HVACs (2021), water heater (tankless Rinnai installed by Maitland/Winter Park plumbing), plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and primary suite have ceiling-installed concert speakers and outdoor speakers. Lower-floor speakers have individual room controls and are served by a pantry stereo system. This exceptional home offers a desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a standout in one of Maitland’s special neighborhoods.

255 W George Avenue, Maitland

$331,000

Experience the best of lakeside living in this beautifully updated third-floor corner residence with panoramic views of Lake Maitland. Perfectly positioned along Orlando Avenue and adjacent to Fort Maitland boat ramp, the home combines convenience with a truly unique lifestyle just minutes from Winter Park’s shopping, dining, and cultural attractions. Inside, you’ll find luxury vinyl plank flooring throughout and a stunning kitchen designed for modern living, showcasing quartz countertops, sleek stainless steel appliances, custom cabinetry, and stylish finishes that create an inviting atmosphere for both cooking and entertaining. The spacious primary suite is highlighted by a custom-designed closet for optimal storage and comfort. Enjoy community amenities that make every day feel like a retreat, including a pool overlooking the lake and access to boat slips (via waitlist) on the highly coveted Winter Park Chain of Lakes. Whether you’re seeking a serene escape or a vibrant, connected lifestyle, this condo delivers the rare combination of location, water views, and thoughtful updates in one of Central Florida’s most desirable areas.

2 Beds ⋅ 2 Baths ⋅ Maitland Harbour Apts SubDv. ⋅ 32751 Zip Code

Experience the best of lakeside living in this beautifully updated third-floor corner residence with panoramic views of Lake Maitland. Perfectly positioned along Orlando Avenue and adjacent to Fort Maitland boat ramp, the home combines convenience with a truly unique lifestyle just minutes from Winter Park’s shopping, dining, and cultural attractions. Inside, you’ll find luxury vinyl plank flooring throughout and a stunning kitchen designed for modern living, showcasing quartz countertops, sleek stainless steel appliances, custom cabinetry, and stylish finishes that create an inviting atmosphere for both cooking and entertaining. The spacious primary suite is highlighted by a custom-designed closet for optimal storage and comfort. Enjoy community amenities that make every day feel like a retreat, including a pool overlooking the lake and access to boat slips (via waitlist) on the highly coveted Winter Park Chain of Lakes. Whether you’re seeking a serene escape or a vibrant, connected lifestyle, this condo delivers the rare combination of location, water views, and thoughtful updates in one of Central Florida’s most desirable areas.

1000 S Orlando Avenue Unit A31, Maitland

$2,999,000

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.

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

$325,000

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.

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

$405,000

Nestled within the exclusive gated lakeside community of Montacino, this impeccably maintained Spanish/Mediterranean-inspired townhome offers refined living surrounded by serene natural beauty. The sought-after two-story Barclay model features an elegant open-concept design, seamlessly blending the spacious great room, dining area, and well-appointed kitchen—thoughtfully designed for both everyday comfort and effortless entertaining. The chef-inspired kitchen showcases rich wood cabinetry, stainless steel appliances with upgraded microwave and dishwasher. The refrigerator and oven to be replaced with Stainless steel appliances by the sellers prior to closing. Expansive windows invite in abundant natural light while framing picturesque views of the lush green space beyond. Step outside to the covered rear patio and enjoy the rare privacy and tranquility of the only Barclay unit in the community backing directly onto this beautiful preserve-like setting, enhanced by custom patio pavers added in 2024. Thoughtful updates throughout the home create a move-in-ready experience. The interior was refreshed with modern gray paint, kitchen and bathroom cabinetry were updated. The Stone countertops were updated with a beautiful Carrera style epoxy in the kitchen and baths, and the primary shower frame was refinished. Smart-home enhancements include Alexa-compatible light switches in the kitchen and primary bedroom, an upgraded alarm system, and a Ring doorbell. All three toilets have been upgraded, along with updated bathroom fixtures including shower rods and accessories. Enhancing the home’s elevated design, the entire first floor features stunning premium oversized luxury vinyl plank flooring, offering both timeless style and durability. Upstairs, the expansive primary suite serves as a peaceful retreat, complete with a generous walk-in closet and a charming private balcony overlooking the greenery beyond. The luxurious en-suite bath features dual vanities and ample room to unwind. Two additional bedrooms, a full secondary bath, and a conveniently located laundry closet complete the second level. Additional highlights include a newer HVAC system, crown molding throughout, engineered hardwood flooring across the second floor, and a one-car garage. Residents of Montacino enjoy access to a sparkling resort-style pool and the scenic beauty of Lake Charity, all while being ideally located just minutes from I-4, premier dining, shopping, and the very best of Orlando living.

3 Beds ⋅ 3 Baths ⋅ Enclave At Maitland SubDv. ⋅ 32751 Zip Code

Nestled within the exclusive gated lakeside community of Montacino, this impeccably maintained Spanish/Mediterranean-inspired townhome offers refined living surrounded by serene natural beauty. The sought-after two-story Barclay model features an elegant open-concept design, seamlessly blending the spacious great room, dining area, and well-appointed kitchen—thoughtfully designed for both everyday comfort and effortless entertaining. The chef-inspired kitchen showcases rich wood cabinetry, stainless steel appliances with upgraded microwave and dishwasher. The refrigerator and oven to be replaced with Stainless steel appliances by the sellers prior to closing. Expansive windows invite in abundant natural light while framing picturesque views of the lush green space beyond. Step outside to the covered rear patio and enjoy the rare privacy and tranquility of the only Barclay unit in the community backing directly onto this beautiful preserve-like setting, enhanced by custom patio pavers added in 2024. Thoughtful updates throughout the home create a move-in-ready experience. The interior was refreshed with modern gray paint, kitchen and bathroom cabinetry were updated. The Stone countertops were updated with a beautiful Carrera style epoxy in the kitchen and baths, and the primary shower frame was refinished. Smart-home enhancements include Alexa-compatible light switches in the kitchen and primary bedroom, an upgraded alarm system, and a Ring doorbell. All three toilets have been upgraded, along with updated bathroom fixtures including shower rods and accessories. Enhancing the home’s elevated design, the entire first floor features stunning premium oversized luxury vinyl plank flooring, offering both timeless style and durability. Upstairs, the expansive primary suite serves as a peaceful retreat, complete with a generous walk-in closet and a charming private balcony overlooking the greenery beyond. The luxurious en-suite bath features dual vanities and ample room to unwind. Two additional bedrooms, a full secondary bath, and a conveniently located laundry closet complete the second level. Additional highlights include a newer HVAC system, crown molding throughout, engineered hardwood flooring across the second floor, and a one-car garage. Residents of Montacino enjoy access to a sparkling resort-style pool and the scenic beauty of Lake Charity, all while being ideally located just minutes from I-4, premier dining, shopping, and the very best of Orlando living.

1295 Blessing Street, Maitland

$1,495,000

A rare opportunity on one of Maitland’s most coveted cul-de-sac streets, where custom estates line a quiet neighborhood bordering the Winter Park Chain of Lakes, this stunning Mediterranean estate offers the privacy of a secluded retreat while placing you just moments from Maitland City Centre, Publix & the area’s vibrant dining and shopping scene. Completely reimagined in 2007 w/ a 2,000+ SF addition, including a new façade, expansive covered front porch & 2-car garage, this 4-bedroom, 3-bath home offers 3,797 SF of beautifully renovated living space on a fully fenced 0.35-acre lot. A paver circular drive welcomes guests, while the arched covered entry sets the tone for the character found throughout. Inside, the foyer offers a gracious arrival w/ a custom built-in library, wood floors & a wood-burning fireplace w/ brick surround. The dining room flows seamlessly to a well-appointed butler’s pantry & wet bar with second dishwasher, beverage refrigerator & sink. Both the dining room and kitchen open to the spacious and comfortable family room, creating exceptional flow for everyday living & entertaining. The kitchen features a Dacor 6-burner professional gas cooktop, GE Monogram double wall ovens with warming drawer, honed oversized black granite countertops, 42” wood cabinetry, travertine floors, designer lighting & an oversized island with seating for four or more. A generously sized eat-in area provides comfortable casual dining, while the adjacent family room features tall ceilings, extensive millwork, decorative wood beams & French doors overlooking the backyard oasis. Privately positioned on the opposite side of the home, the primary suite is a true sanctuary w/ two organized walk-in closets, back porch access & a renovated spa bath featuring a freestanding soaking tub, frameless glass shower & beautifully appointed vanity. Located near the primary suite on the main level, a versatile second bedroom sits across the hall from a full bath and works well as a guest suite, office, nursery or fitness room. The first floor is further enhanced by an exceptional media room with platform theater-style seating & surround sound set up, along w/ a large laundry room featuring exceptional storage & a second-floor laundry chute. Upstairs, two generous bedrooms w/ decorative beamed ceilings & ample closets share a Jack-and-Jill bath w/ jetted tub, while the rear bedroom opens to a deep balcony overlooking the grounds. Outside, the fully fenced lot delivers a resort-like setting with sparkling pool, covered porch w/ a tongue and groove ceiling, open entertaining deck & mature landscaping designed for both privacy and enjoyment. A rear gate offers direct access to Maitland City Centre, the farmers market, restaurants, retail & grocery just three blocks away. New roof w/ skylight 2021. Three upgraded HVAC systems 2021–2023. Twenty-five new double-pane, Low-E, argon-filled window, double-strength glass currently in progress & expected to be completed by the end of May. Satisfactory 4-Point Inspection and professional measurement completed May 2026. Offering exceptional privacy, generous living spaces & a remarkably walkable location, this is your opportunity to own a beautifully updated home in one of Maitland’s most desirable neighborhoods, zoned for highly regarded Winter Park High School & convenient to Orlando Avenue, Minnehaha Park, Lake Lily, Fort Maitland, and less than ten minutes from the shops and restaurants of Winter Park's Park Avenue.

4 Beds ⋅ 3 Baths ⋅ Packwood Sub SubDv. ⋅ 32751 Zip Code

A rare opportunity on one of Maitland’s most coveted cul-de-sac streets, where custom estates line a quiet neighborhood bordering the Winter Park Chain of Lakes, this stunning Mediterranean estate offers the privacy of a secluded retreat while placing you just moments from Maitland City Centre, Publix & the area’s vibrant dining and shopping scene. Completely reimagined in 2007 w/ a 2,000+ SF addition, including a new façade, expansive covered front porch & 2-car garage, this 4-bedroom, 3-bath home offers 3,797 SF of beautifully renovated living space on a fully fenced 0.35-acre lot. A paver circular drive welcomes guests, while the arched covered entry sets the tone for the character found throughout. Inside, the foyer offers a gracious arrival w/ a custom built-in library, wood floors & a wood-burning fireplace w/ brick surround. The dining room flows seamlessly to a well-appointed butler’s pantry & wet bar with second dishwasher, beverage refrigerator & sink. Both the dining room and kitchen open to the spacious and comfortable family room, creating exceptional flow for everyday living & entertaining. The kitchen features a Dacor 6-burner professional gas cooktop, GE Monogram double wall ovens with warming drawer, honed oversized black granite countertops, 42” wood cabinetry, travertine floors, designer lighting & an oversized island with seating for four or more. A generously sized eat-in area provides comfortable casual dining, while the adjacent family room features tall ceilings, extensive millwork, decorative wood beams & French doors overlooking the backyard oasis. Privately positioned on the opposite side of the home, the primary suite is a true sanctuary w/ two organized walk-in closets, back porch access & a renovated spa bath featuring a freestanding soaking tub, frameless glass shower & beautifully appointed vanity. Located near the primary suite on the main level, a versatile second bedroom sits across the hall from a full bath and works well as a guest suite, office, nursery or fitness room. The first floor is further enhanced by an exceptional media room with platform theater-style seating & surround sound set up, along w/ a large laundry room featuring exceptional storage & a second-floor laundry chute. Upstairs, two generous bedrooms w/ decorative beamed ceilings & ample closets share a Jack-and-Jill bath w/ jetted tub, while the rear bedroom opens to a deep balcony overlooking the grounds. Outside, the fully fenced lot delivers a resort-like setting with sparkling pool, covered porch w/ a tongue and groove ceiling, open entertaining deck & mature landscaping designed for both privacy and enjoyment. A rear gate offers direct access to Maitland City Centre, the farmers market, restaurants, retail & grocery just three blocks away. New roof w/ skylight 2021. Three upgraded HVAC systems 2021–2023. Twenty-five new double-pane, Low-E, argon-filled window, double-strength glass currently in progress & expected to be completed by the end of May. Satisfactory 4-Point Inspection and professional measurement completed May 2026. Offering exceptional privacy, generous living spaces & a remarkably walkable location, this is your opportunity to own a beautifully updated home in one of Maitland’s most desirable neighborhoods, zoned for highly regarded Winter Park High School & convenient to Orlando Avenue, Minnehaha Park, Lake Lily, Fort Maitland, and less than ten minutes from the shops and restaurants of Winter Park's Park Avenue.

221 Minnehaha Road, Maitland

$107,000

Beautiful condo located in the desirable Carrington Park community! This well-maintained unit offers a spacious layout, comfortable living spaces, and a great location close to shopping, restaurants, major highways, and UCF. Community amenities include multiple swimming pools, fitness center, playground, and more. Great opportunity for homeowners or investors alike!

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

Beautiful condo located in the desirable Carrington Park community! This well-maintained unit offers a spacious layout, comfortable living spaces, and a great location close to shopping, restaurants, major highways, and UCF. Community amenities include multiple swimming pools, fitness center, playground, and more. Great opportunity for homeowners or investors alike!

508 Banyon Tree Circle Unit 202, Maitland

$139,900

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.

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

$260,000

This is the kind of first home that makes life easier. With over 1,500 SqFt, 3 bedrooms, 2.5 baths, and thoughtful updates throughout, this Maitland condo gives you room to grow without the heavy upkeep of a single family home. The remodeled kitchen features quartz counters, stainless steel appliances, and updated cabinetry, while downstairs tile flooring keeps maintenance simple. Enjoy a large dining area, separate living room, laundry room, enclosed patio, and attached garage. Upstairs, the spacious primary suite opens to a balcony overlooking the courtyard. The community pool, lake access, and HOA covered exterior maintenance add even more value, all in a location close to Maitland favorites, Winter Park, and downtown Orlando.

3 Beds ⋅ 3 Baths ⋅ Park Lake Twnhs Ph 02 SubDv. ⋅ 32751 Zip Code

This is the kind of first home that makes life easier. With over 1,500 SqFt, 3 bedrooms, 2.5 baths, and thoughtful updates throughout, this Maitland condo gives you room to grow without the heavy upkeep of a single family home. The remodeled kitchen features quartz counters, stainless steel appliances, and updated cabinetry, while downstairs tile flooring keeps maintenance simple. Enjoy a large dining area, separate living room, laundry room, enclosed patio, and attached garage. Upstairs, the spacious primary suite opens to a balcony overlooking the courtyard. The community pool, lake access, and HOA covered exterior maintenance add even more value, all in a location close to Maitland favorites, Winter Park, and downtown Orlando.

868 Town Circle Unit 123, Maitland

$549,000

*Seller is Offering 20k Credit to buyers at closing towards future upgrades!* 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, 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.

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

*Seller is Offering 20k Credit to buyers at closing towards future upgrades!* 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, 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

$1,695,000

Under contract-accepting backup offers. Priced for quick sale! Modern, mediterranean lakefront residence in one of Maitland’s most desirable GATED communities, positioned on a private cul-de-sac atop a natural rise. Set on over 1.3 acres with approximately 179 feet of frontage on Lake Jackson (ski lake), the property offers a rare combination of elevation, privacy and expansive water views in a central Maitland location with quick access to I-4, downtown Maitland and Park Avenue, Winter Park. Lake Colony Estates is conveniently located across the street from Orangewood School. The home was custom built by Keith Groninger, a 10-time Parade of Homes winner. A tree-lined drive leads to a paved driveway and a welcoming entry with imported hand-crafted 8-foot wood doors and tile roof. Inside, the foyer opens to a dramatic great room with 20-foot cathedral ceilings, clerestory windows and a floor-to-ceiling wood burning fireplace, butlers pantry and wet bar. The home has been refreshed with white interior paint, enhancing the natural light and giving the interiors a timeless backdrop. The gourmet kitchen is designed for both function and gathering, featuring 3cm granite countertops, a large island, 5-burner gas cooktop with custom stone and mortar arch detail, tumbled marble backsplash and vaulted ceilings with exposed wood beams sourced from Pennsylvania. Expansive lake-facing pocketing windows frame Lake Jackson and open the chef’s kitchen to the screened porch for effortless outdoor dining and entertaining The first-floor primary suite features engineered hardwood floors, direct access to the outdoor pool and a spacious bath finished in tumbled marble with a soaking tub, dual vanities and walk-in shower. A large custom walk-in closet provides generous storage. Upstairs, three oversized bedrooms each offer ensuite baths and a large bonus room overlooking the lake. Outdoor living is centered around the covered, screened porch, lakefront setting and gated pool. The private and expansive lawn -179 feet of shoreline, complemented by a private boathouse (newer lift) with direct access to Lake Jackson for boating, skiing, jet skis, canoes, paddleboards and more! Also, enjoy sunrise views over Lake Jackson! Additional features include two new ACs, oversized three-car garage, amazing storage and closet spaces, mature and new landscaping and carefully maintained architectural detailing throughout. Four point, roof certification and wind mitigation reports will be provided by the sellers. Seawall maintained by HOA. No flood insurance required on the home.

4 Beds ⋅ 5 Baths ⋅ Lake Colony Ph 02 SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Priced for quick sale! Modern, mediterranean lakefront residence in one of Maitland’s most desirable GATED communities, positioned on a private cul-de-sac atop a natural rise. Set on over 1.3 acres with approximately 179 feet of frontage on Lake Jackson (ski lake), the property offers a rare combination of elevation, privacy and expansive water views in a central Maitland location with quick access to I-4, downtown Maitland and Park Avenue, Winter Park. Lake Colony Estates is conveniently located across the street from Orangewood School. The home was custom built by Keith Groninger, a 10-time Parade of Homes winner. A tree-lined drive leads to a paved driveway and a welcoming entry with imported hand-crafted 8-foot wood doors and tile roof. Inside, the foyer opens to a dramatic great room with 20-foot cathedral ceilings, clerestory windows and a floor-to-ceiling wood burning fireplace, butlers pantry and wet bar. The home has been refreshed with white interior paint, enhancing the natural light and giving the interiors a timeless backdrop. The gourmet kitchen is designed for both function and gathering, featuring 3cm granite countertops, a large island, 5-burner gas cooktop with custom stone and mortar arch detail, tumbled marble backsplash and vaulted ceilings with exposed wood beams sourced from Pennsylvania. Expansive lake-facing pocketing windows frame Lake Jackson and open the chef’s kitchen to the screened porch for effortless outdoor dining and entertaining The first-floor primary suite features engineered hardwood floors, direct access to the outdoor pool and a spacious bath finished in tumbled marble with a soaking tub, dual vanities and walk-in shower. A large custom walk-in closet provides generous storage. Upstairs, three oversized bedrooms each offer ensuite baths and a large bonus room overlooking the lake. Outdoor living is centered around the covered, screened porch, lakefront setting and gated pool. The private and expansive lawn -179 feet of shoreline, complemented by a private boathouse (newer lift) with direct access to Lake Jackson for boating, skiing, jet skis, canoes, paddleboards and more! Also, enjoy sunrise views over Lake Jackson! Additional features include two new ACs, oversized three-car garage, amazing storage and closet spaces, mature and new landscaping and carefully maintained architectural detailing throughout. Four point, roof certification and wind mitigation reports will be provided by the sellers. Seawall maintained by HOA. No flood insurance required on the home.

1244 E Lake Colony Drive, Maitland

$169,900

Amazing upgraded two-bedroom, one bath Condo in the gated waterfront community at Visconti in Maitland with features of spacious living and comfortability. This stunning Condo Unit features with large windows letting in plenty of natural light and giving the common living area a fresh air feel. The dining/living combo opens to a big, screened patio through sliding glass doors. The kitchen overlooks the living and dining room and contains a full suite, including the refrigerator, range, dishwasher, disposal and plenty of cabinet and countertop. The bedroom is also including a large walk-in closet. This unit has oversized laundry room that includes full-size washer and dryer.Visconti community comes with professional maintenance of Ponds, professionally landscaped and well-maintained common areas as well as a BEAUTIFUL Resort Style Pool and Club House along with tennis court, fitness, basketball court, car washing area ext. Primely located close to all shopping, entertainment areas and just minutes to major highways, I4. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures are not included to the listing

2 Beds ⋅ 1 Baths ⋅ Visconti West SubDv. ⋅ 32751 Zip Code

Amazing upgraded two-bedroom, one bath Condo in the gated waterfront community at Visconti in Maitland with features of spacious living and comfortability. This stunning Condo Unit features with large windows letting in plenty of natural light and giving the common living area a fresh air feel. The dining/living combo opens to a big, screened patio through sliding glass doors. The kitchen overlooks the living and dining room and contains a full suite, including the refrigerator, range, dishwasher, disposal and plenty of cabinet and countertop. The bedroom is also including a large walk-in closet. This unit has oversized laundry room that includes full-size washer and dryer.Visconti community comes with professional maintenance of Ponds, professionally landscaped and well-maintained common areas as well as a BEAUTIFUL Resort Style Pool and Club House along with tennis court, fitness, basketball court, car washing area ext. Primely located close to all shopping, entertainment areas and just minutes to major highways, I4. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures are not included to the listing

1375 Lake Shadow Circle Unit 11203, Maitland

$190,000

Virtually Staged. Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the sought-after Visconti community, where comfort, convenience, and lifestyle come together. Located on the third floor, this light-filled residence features soaring vaulted ceilings that create an open, airy feel, complemented by abundant natural light throughout. Ideally positioned just steps from the clubhouse, you’ll enjoy effortless access to resort-style amenities, including a sparkling pool and fully equipped fitness center—perfect for both relaxation and an active lifestyle. This move-in ready condo is an excellent opportunity for both homeowners and investors alike. With quick access to I-4, commuting to Downtown Orlando is easy, while the shopping, dining, and entertainment of Altamonte Springs are just minutes away. Opportunities like this in Visconti don’t last—schedule your private showing today.

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

Virtually Staged. Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the sought-after Visconti community, where comfort, convenience, and lifestyle come together. Located on the third floor, this light-filled residence features soaring vaulted ceilings that create an open, airy feel, complemented by abundant natural light throughout. Ideally positioned just steps from the clubhouse, you’ll enjoy effortless access to resort-style amenities, including a sparkling pool and fully equipped fitness center—perfect for both relaxation and an active lifestyle. This move-in ready condo is an excellent opportunity for both homeowners and investors alike. With quick access to I-4, commuting to Downtown Orlando is easy, while the shopping, dining, and entertainment of Altamonte Springs are just minutes away. Opportunities like this in Visconti don’t last—schedule your private showing today.

1100 Lake Shadow Circle Unit 2307, Maitland

$155,000

Nice one-bedroom unit on the ground floor featuring brand-new laminate countertops in both the kitchen and bathroom, along with stainless steel appliances. Located in a gated, resort-style community offering top amenities including a pool, fitness center, tennis and basketball courts, playground, clubroom, and car wash. All in an excellent Maitland location!

1 Beds ⋅ 1 Baths ⋅ Visconti West Condo SubDv. ⋅ 32751 Zip Code

Nice one-bedroom unit on the ground floor featuring brand-new laminate countertops in both the kitchen and bathroom, along with stainless steel appliances. Located in a gated, resort-style community offering top amenities including a pool, fitness center, tennis and basketball courts, playground, clubroom, and car wash. All in an excellent Maitland location!

1400 Lake Shadow Circle Unit 10103, Maitland

$467,000

Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated spacious kitchen features stainless steel appliances and a breakfast nook situated in a bay window. The dining living room combo is very spacious making it perfect for relaxing or entertaining. The condo offers washer and dryer in the unit as well as a private storage closet on the same floor just across the hall. The Moorings Lakefront community offers an amazing recently updated pool and spa area along a large clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this condo and community offers an amazing combination of comfort and convenience.

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code

Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated spacious kitchen features stainless steel appliances and a breakfast nook situated in a bay window. The dining living room combo is very spacious making it perfect for relaxing or entertaining. The condo offers washer and dryer in the unit as well as a private storage closet on the same floor just across the hall. The Moorings Lakefront community offers an amazing recently updated pool and spa area along a large clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this condo and community offers an amazing combination of comfort and convenience.

204 Quayside Circle Unit 201, Maitland

$362,500

This beautiful Maitland Florida town home feels like living in a gated resort! 3 bedrooms, 2 1/2 baths, plus garage and loaded with upgrades including hardwood floors on both levels, crown molding, tall wood cabinets, stone counters and so much more. Welcoming entry foyer with half bath, kitchen with island sink, large breakfast bar, stainless appliances, granite counters and custom backsplash. Inviting living room and dining area offer plenty of space for entertaining, french door opens to private covered porch which overlooks the rear yard. Upstairs the ensuite primary bedroom has a walk-in closet, great covered balcony area and a dual sink bathroom with glass enclosed shower. Additional 2 bedrooms in the front of the upstairs share a hall bath and laundry closet with washer and dryer included. Montacino is a gated European feeling award winning community with amazing pool area, lake frontage and a convenient location to shopping and i4. This townhouse has a quiet location within the community offering privacy in the back area. All exterior maintenance is included (roof and paint too)! HOA dues include new fiber with internet and channel package and all Montacino amenities.

3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code

This beautiful Maitland Florida town home feels like living in a gated resort! 3 bedrooms, 2 1/2 baths, plus garage and loaded with upgrades including hardwood floors on both levels, crown molding, tall wood cabinets, stone counters and so much more. Welcoming entry foyer with half bath, kitchen with island sink, large breakfast bar, stainless appliances, granite counters and custom backsplash. Inviting living room and dining area offer plenty of space for entertaining, french door opens to private covered porch which overlooks the rear yard. Upstairs the ensuite primary bedroom has a walk-in closet, great covered balcony area and a dual sink bathroom with glass enclosed shower. Additional 2 bedrooms in the front of the upstairs share a hall bath and laundry closet with washer and dryer included. Montacino is a gated European feeling award winning community with amazing pool area, lake frontage and a convenient location to shopping and i4. This townhouse has a quiet location within the community offering privacy in the back area. All exterior maintenance is included (roof and paint too)! HOA dues include new fiber with internet and channel package and all Montacino amenities.

1393 Benevolent Street, Maitland

$175,000

Welcome to Visconti! A Gated Waterfront Community in the Heart of Maitland. Step into an easy, low-maintenance living with this move-in ready 2-bedroom, 2-bath condo located on the third floor, offering added privacy and a peaceful, elevated feel. With all new flooring and fresh interior paint, this home is completely refreshed and ready for its next owner. The split floor plan layout offers a comfortable and functional flow, ideal for both everyday living and entertaining. Natural light fills the space, creating a bright and inviting atmosphere throughout. Whether you’re starting your day or winding down in the evening, this home delivers a relaxed, low-stress environment that truly feels like home. Located within the highly desirable Visconti community, residents enjoy resort-style amenities including a sparkling pool, fitness center, clubhouse, tennis and basketball courts, playground, and scenic walking paths with a waterfront gazebo. The gated entry and beautifully maintained grounds enhance both privacy and curb appeal. The HOA includes water service and valet trash, helping simplify your monthly expenses and making condo living even more convenient. Positioned in one of Maitland’s most central locations, you’ll have quick access to I-4, 414, and 434, with nearby shopping, dining, and entertainment options including Maitland Promenade, Winter Park Village, Cranes Roost Park, and Uptown Altamonte. Downtown Orlando is just a short drive away. If you’re looking for a fully updated, move-in ready condo in a gated community with strong amenities and an unbeatable location, this one checks all the boxes.

2 Beds ⋅ 2 Baths ⋅ Visconti West Condo SubDv. ⋅ 32751 Zip Code

Welcome to Visconti! A Gated Waterfront Community in the Heart of Maitland. Step into an easy, low-maintenance living with this move-in ready 2-bedroom, 2-bath condo located on the third floor, offering added privacy and a peaceful, elevated feel. With all new flooring and fresh interior paint, this home is completely refreshed and ready for its next owner. The split floor plan layout offers a comfortable and functional flow, ideal for both everyday living and entertaining. Natural light fills the space, creating a bright and inviting atmosphere throughout. Whether you’re starting your day or winding down in the evening, this home delivers a relaxed, low-stress environment that truly feels like home. Located within the highly desirable Visconti community, residents enjoy resort-style amenities including a sparkling pool, fitness center, clubhouse, tennis and basketball courts, playground, and scenic walking paths with a waterfront gazebo. The gated entry and beautifully maintained grounds enhance both privacy and curb appeal. The HOA includes water service and valet trash, helping simplify your monthly expenses and making condo living even more convenient. Positioned in one of Maitland’s most central locations, you’ll have quick access to I-4, 414, and 434, with nearby shopping, dining, and entertainment options including Maitland Promenade, Winter Park Village, Cranes Roost Park, and Uptown Altamonte. Downtown Orlando is just a short drive away. If you’re looking for a fully updated, move-in ready condo in a gated community with strong amenities and an unbeatable location, this one checks all the boxes.

1440 Lake Shadow Circle Unit 8305, Maitland

$113,000

Great opportunity to own this 1-bedroom, 1-bathroom first-floor unit in a desirable and well-maintained community! This property offers a comfortable and functional layout with easy first-floor access, perfect for both homeowners and investors alike. Currently tenant-occupied with a lease in place through June 30, 2026, providing immediate rental income with future flexibility for personal use. Residents enjoy access to excellent community amenities, including a sparkling pool, fitness center, and playground, all within a lovely and welcoming environment. Conveniently located near major highways, shopping, dining, and entertainment, this property offers both lifestyle and investment potential. Don’t miss this versatile opportunity!

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Great opportunity to own this 1-bedroom, 1-bathroom first-floor unit in a desirable and well-maintained community! This property offers a comfortable and functional layout with easy first-floor access, perfect for both homeowners and investors alike. Currently tenant-occupied with a lease in place through June 30, 2026, providing immediate rental income with future flexibility for personal use. Residents enjoy access to excellent community amenities, including a sparkling pool, fitness center, and playground, all within a lovely and welcoming environment. Conveniently located near major highways, shopping, dining, and entertainment, this property offers both lifestyle and investment potential. Don’t miss this versatile opportunity!

2422 Branch Way Unit 100, Maitland

$299,000

Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away.

2 Beds ⋅ 2 Baths ⋅ Sun Bay Club Condo SubDv. ⋅ 32751 Zip Code

Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away.

1000 Winderley Place Unit 239, Maitland

$250,000

Welcome to Lake Maitland Terrace. Corner unit with screened in porch and lake view. As-is property.

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

Welcome to Lake Maitland Terrace. Corner unit with screened in porch and lake view. As-is property.

1140 S Orlando Avenue Unit K10, Maitland

$599,000

TURN KEY AND RENOVATED IN SOUGHT-AFTER WEST COVE!! Wake up to breathtaking sunrises with a stunning, unobstructed view stretching across Lake Maitland—the largest lake in the highly sought-after Winter Park Chain of Lakes—from this beautifully renovated, truly turnkey condominium. All flooring, bathrooms, fixtures, paint, AC, water heater, sliding door to balcony, kitchen/appliances, and closet systems have been painstakingly updated to the highest level, making for an unparalleled opportunity to simply move right in and begin enjoying immersive lake views. The primary suite has been reimagined and has its own ensuite bath and a new built-in closet with copious storage, complete with signature views of Lake Maitland. This spacious residence offers an ideal central location, just moments from an array of dining options, Lake Lily Park, Enzian Theater, and convenient access to Interstate 4 via Lee Road or Maitland Boulevard. The monthly association fee—lower than most lakefront communities—provides exceptional value and includes access to lakefront docks (with boat slips available on a first-come basis), a fitness center, an inviting lobby for entertaining, a heated pool and spa, a grilling area with seating, storage for canoes, kayaks, and paddleboards, assigned and guest parking, laundry facilities on every floor, Spectrum cable and internet, as well as water, sewer, and trash services. This property may be under audio/visual surveillance.

2 Beds ⋅ 2 Baths ⋅ West Cove Condo SubDv. ⋅ 32751 Zip Code

TURN KEY AND RENOVATED IN SOUGHT-AFTER WEST COVE!! Wake up to breathtaking sunrises with a stunning, unobstructed view stretching across Lake Maitland—the largest lake in the highly sought-after Winter Park Chain of Lakes—from this beautifully renovated, truly turnkey condominium. All flooring, bathrooms, fixtures, paint, AC, water heater, sliding door to balcony, kitchen/appliances, and closet systems have been painstakingly updated to the highest level, making for an unparalleled opportunity to simply move right in and begin enjoying immersive lake views. The primary suite has been reimagined and has its own ensuite bath and a new built-in closet with copious storage, complete with signature views of Lake Maitland. This spacious residence offers an ideal central location, just moments from an array of dining options, Lake Lily Park, Enzian Theater, and convenient access to Interstate 4 via Lee Road or Maitland Boulevard. The monthly association fee—lower than most lakefront communities—provides exceptional value and includes access to lakefront docks (with boat slips available on a first-come basis), a fitness center, an inviting lobby for entertaining, a heated pool and spa, a grilling area with seating, storage for canoes, kayaks, and paddleboards, assigned and guest parking, laundry facilities on every floor, Spectrum cable and internet, as well as water, sewer, and trash services. This property may be under audio/visual surveillance.

1100 S Orlando Avenue Unit 306, Maitland

$324,000

Offered at a newly improved price, this highly desirable residence at Maitland Harbour is located within a boutique 38-unit lakefront condominium community nestled in the heart of Maitland. Ideally positioned on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—this intimate and picturesque enclave offers access to the entire chain and a truly exceptional waterfront lifestyle. A hidden gem, Maitland Harbour blends timeless Mid-Century Modern architecture with the serenity of lakefront living. Designed by renowned architect Manfred Lopatka, a protégé of Frank Lloyd Wright, and built in 1964, the community reflects a distinctive Central Florida interpretation of classic modernist design. Inside this beautifully updated 2-bedroom, 2-bath residence offering 952 square feet, you will find light-filled living space with a clean, cohesive aesthetic throughout. The kitchen, renovated in 2020, features quartz countertops, a subway tile backsplash, open wood shelving, and a pass-through to the dining area, creating both functionality and visual connection to the main living space. The open-concept living and dining areas are bright and inviting, with warm-toned wood flooring and neutral finishes. The primary suite is a true retreat, complete with updated flooring (2020), soft natural light, newly added barn-style closet doors for improved storage access, and direct access to the private balcony—ideal for enjoying morning coffee or evening breezes. The en-suite bath, renovated by a previous owner, features neutral finishes and a glass-enclosed shower. The secondary bedroom is spacious and offers consistent updated flooring and fresh paint, and is located adjacent to a full guest bath with recent updates including vanity, lighting, and fixtures. Additional improvements include a new refrigerator (2023), new windows (2024), new HVAC (2025), and fresh interior paint (2025/2026). The community has completed major improvements including new roofs, pool enclosure, and exterior paint, and both the milestone inspection and structural integrity reserve study have been completed and are available for review. Residents enjoy a full suite of lakefront amenities including a waterfront pool, courtyard, boat slips, fishing pier, kayak storage, community room, private storage, covered parking, and an expansive entertaining deck overlooking Lake Maitland. The location is adjacent to historic Fort Maitland Park and directly across from Lake Lily, the heart of Maitland’s Cultural Corridor, known for concerts, the Maitland Art Festival, and the Sunday Farmers Market, and is just a short walk to the Enzian Theater and local dining, with easy access to Winter Park’s Park Avenue offering premier shopping, restaurants, museums, and year-round events. Enjoy low-maintenance lakefront living with beautiful interior spaces, a private balcony, and access to one of Central Florida’s most sought-after waterfront settings.

2 Beds ⋅ 2 Baths ⋅ Maitland Harbour Apts SubDv. ⋅ 32751 Zip Code

Offered at a newly improved price, this highly desirable residence at Maitland Harbour is located within a boutique 38-unit lakefront condominium community nestled in the heart of Maitland. Ideally positioned on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—this intimate and picturesque enclave offers access to the entire chain and a truly exceptional waterfront lifestyle. A hidden gem, Maitland Harbour blends timeless Mid-Century Modern architecture with the serenity of lakefront living. Designed by renowned architect Manfred Lopatka, a protégé of Frank Lloyd Wright, and built in 1964, the community reflects a distinctive Central Florida interpretation of classic modernist design. Inside this beautifully updated 2-bedroom, 2-bath residence offering 952 square feet, you will find light-filled living space with a clean, cohesive aesthetic throughout. The kitchen, renovated in 2020, features quartz countertops, a subway tile backsplash, open wood shelving, and a pass-through to the dining area, creating both functionality and visual connection to the main living space. The open-concept living and dining areas are bright and inviting, with warm-toned wood flooring and neutral finishes. The primary suite is a true retreat, complete with updated flooring (2020), soft natural light, newly added barn-style closet doors for improved storage access, and direct access to the private balcony—ideal for enjoying morning coffee or evening breezes. The en-suite bath, renovated by a previous owner, features neutral finishes and a glass-enclosed shower. The secondary bedroom is spacious and offers consistent updated flooring and fresh paint, and is located adjacent to a full guest bath with recent updates including vanity, lighting, and fixtures. Additional improvements include a new refrigerator (2023), new windows (2024), new HVAC (2025), and fresh interior paint (2025/2026). The community has completed major improvements including new roofs, pool enclosure, and exterior paint, and both the milestone inspection and structural integrity reserve study have been completed and are available for review. Residents enjoy a full suite of lakefront amenities including a waterfront pool, courtyard, boat slips, fishing pier, kayak storage, community room, private storage, covered parking, and an expansive entertaining deck overlooking Lake Maitland. The location is adjacent to historic Fort Maitland Park and directly across from Lake Lily, the heart of Maitland’s Cultural Corridor, known for concerts, the Maitland Art Festival, and the Sunday Farmers Market, and is just a short walk to the Enzian Theater and local dining, with easy access to Winter Park’s Park Avenue offering premier shopping, restaurants, museums, and year-round events. Enjoy low-maintenance lakefront living with beautiful interior spaces, a private balcony, and access to one of Central Florida’s most sought-after waterfront settings.

1000 S Orlando Avenue Unit B25, Maitland

$1,010,000

PRICE REDUCTION, Incredible price for this property! LOCATION, LOCATION, LOCATION! Ideally situated just off Park Avenue in the highly desirable Maitland/Winter Park area, this beautifully maintained home offers the perfect blend of charm, functionality, and convenience. Featuring 4 bedrooms and 3.5 bathrooms, the home welcomes you with elegant formal living and dining spaces enhanced by detailed trim work, crown molding, and updated lighting. The spacious kitchen is designed for both everyday living and entertaining, showcasing a large quartz island and seamlessly overlooking the inviting family room, highlighted by a stunning fireplace. Step outside to a private backyard retreat complete with a spacious deck and covered patio—ideal for enjoying Florida’s outdoor lifestyle and hosting gatherings year-round. The primary suite, located on the second floor, offers a peaceful escape with its own private balcony—perfect for morning coffee or evening relaxation. The spa-like primary bathroom has been fully updated with a large walk-in shower, freestanding soaking tub, and modern finishes, along with an expansive walk-in closet featuring custom built-ins. Additional highlights include a freshly painted interior, a newer roof (2023), a fully fenced yard, large shed and beautifully landscaped grounds with irrigation and mature fruit trees. The extended driveway leads to a detached 2-car garage equipped with an electric vehicle charging station for modern convenience. Home is zoned for Winter Park Highs school and Dommerich Elementary. It is also conveniently located just minutes from Enzian Theater, Park Maitland School and the top shopping and dining destinations Winter Park has to offer, this move-in ready home delivers exceptional living in one of Central Florida’s most sought-after locations.

4 Beds ⋅ 4 Baths ⋅ Dixie Terrace SubDv. ⋅ 32751 Zip Code

PRICE REDUCTION, Incredible price for this property! LOCATION, LOCATION, LOCATION! Ideally situated just off Park Avenue in the highly desirable Maitland/Winter Park area, this beautifully maintained home offers the perfect blend of charm, functionality, and convenience. Featuring 4 bedrooms and 3.5 bathrooms, the home welcomes you with elegant formal living and dining spaces enhanced by detailed trim work, crown molding, and updated lighting. The spacious kitchen is designed for both everyday living and entertaining, showcasing a large quartz island and seamlessly overlooking the inviting family room, highlighted by a stunning fireplace. Step outside to a private backyard retreat complete with a spacious deck and covered patio—ideal for enjoying Florida’s outdoor lifestyle and hosting gatherings year-round. The primary suite, located on the second floor, offers a peaceful escape with its own private balcony—perfect for morning coffee or evening relaxation. The spa-like primary bathroom has been fully updated with a large walk-in shower, freestanding soaking tub, and modern finishes, along with an expansive walk-in closet featuring custom built-ins. Additional highlights include a freshly painted interior, a newer roof (2023), a fully fenced yard, large shed and beautifully landscaped grounds with irrigation and mature fruit trees. The extended driveway leads to a detached 2-car garage equipped with an electric vehicle charging station for modern convenience. Home is zoned for Winter Park Highs school and Dommerich Elementary. It is also conveniently located just minutes from Enzian Theater, Park Maitland School and the top shopping and dining destinations Winter Park has to offer, this move-in ready home delivers exceptional living in one of Central Florida’s most sought-after locations.

1610 Lyndale Boulevard, Maitland

$504,000

LAKEFRONT PARADISE ON LAKE MAITLAND AND THE WINTER PARK CHAIN OF LAKES. Cue the Jimmy Buffett music as you arrive home to your own serene tropical lakefront paradise here at The Moorings on Lake Maitland. The pace feels a bit more relaxed here on the water! This beautiful, move-in ready FULL lakefront condo is located on the third floor of building 3 which is closest to the water. Imagine every day feeling like a tropical vacation in this coveted community with no outside maintenance for you to tend to. Step onto the elevator and effortlessly arrive at your front door. Step inside to find breathtaking panoramic views of sparkling Lake Maitland through oversized glass doors leading to your own private balcony. Enjoy lake views from every single room, even from both bathtubs! Start your mornings with quiet reflections on your peaceful balcony with the soothing sounds of nature and the lake waters gently lapping on the shoreline. Wind down your evenings visiting with friends on the community lawn or expansive dock under painted skies with cool lake breezes. Launch a kayak from the community dock and explore the wonders and natural beauty found throughout the coveted Chain of Lakes. Have your own boat? Newly renovated Fort Maitland Park is next door with day parking and a convenient boat launch. And from time to time, it’s possible that a private boat slip at The Moorings could come available for private purchase or lease. The spacious interior of this condo offers a pleasing neutral color palette with luxury vinyl wood flooring in the living area and primary suite. Attractive oversized tile graces the foyer, kitchen, dining alcove, bathrooms, and balcony. The current décor leans into a vintage Florida tropical vibe allowing you to easily envision the vacation-every-day-feeling! The spacious foyer includes a walk-in storage closet. The well-appointed kitchen is outfitted with custom wood cabinetry, gorgeous granite counters, stainless appliances, a closet pantry in the hall, and glorious water views from the large pass-through opening with breakfast bar. Dine with friends surrounded by water views from the dinette, from the main dining area (currently used as additional living area), or from your balcony. No worries about lugging laundry to a community space--enjoy a double door laundry closet. The combo living dining area is currently set up as all living space providing wonderful entertaining and lounging opportunities. Wake up every morning to serene water views in this private primary suite with double windows for unobstructed views and French door access to the balcony. The beautiful en-suite has a granite dual sink vanity, walk-in closet, and a garden soaking tub and shower with water views as well! Imagine the relaxing baths you could have here! BR two has cozy carpet and a double door closet with easy access to the hall bath with granite sink vanity and a tub/shower. This is a tranquil community with abundant privacy, but opportunities abound for connection if you’d like. The clubhouse has regular gatherings and events, and the recently refurbished pool and spa are ideal for total relaxation or for connecting with friends. Popular restaurants such as Luke’s, Antonio’s, and Athena’s are found just outside the community and a stone’s throw will land you at Enzian Theater with Eden Bar, the Maitland Art Center, all of the wonderful cultural venues and retail establishments of Winter Park and Orlando, and so much more. Welcome home!

2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo Bldg 03 SubDv. ⋅ 32751 Zip Code

LAKEFRONT PARADISE ON LAKE MAITLAND AND THE WINTER PARK CHAIN OF LAKES. Cue the Jimmy Buffett music as you arrive home to your own serene tropical lakefront paradise here at The Moorings on Lake Maitland. The pace feels a bit more relaxed here on the water! This beautiful, move-in ready FULL lakefront condo is located on the third floor of building 3 which is closest to the water. Imagine every day feeling like a tropical vacation in this coveted community with no outside maintenance for you to tend to. Step onto the elevator and effortlessly arrive at your front door. Step inside to find breathtaking panoramic views of sparkling Lake Maitland through oversized glass doors leading to your own private balcony. Enjoy lake views from every single room, even from both bathtubs! Start your mornings with quiet reflections on your peaceful balcony with the soothing sounds of nature and the lake waters gently lapping on the shoreline. Wind down your evenings visiting with friends on the community lawn or expansive dock under painted skies with cool lake breezes. Launch a kayak from the community dock and explore the wonders and natural beauty found throughout the coveted Chain of Lakes. Have your own boat? Newly renovated Fort Maitland Park is next door with day parking and a convenient boat launch. And from time to time, it’s possible that a private boat slip at The Moorings could come available for private purchase or lease. The spacious interior of this condo offers a pleasing neutral color palette with luxury vinyl wood flooring in the living area and primary suite. Attractive oversized tile graces the foyer, kitchen, dining alcove, bathrooms, and balcony. The current décor leans into a vintage Florida tropical vibe allowing you to easily envision the vacation-every-day-feeling! The spacious foyer includes a walk-in storage closet. The well-appointed kitchen is outfitted with custom wood cabinetry, gorgeous granite counters, stainless appliances, a closet pantry in the hall, and glorious water views from the large pass-through opening with breakfast bar. Dine with friends surrounded by water views from the dinette, from the main dining area (currently used as additional living area), or from your balcony. No worries about lugging laundry to a community space--enjoy a double door laundry closet. The combo living dining area is currently set up as all living space providing wonderful entertaining and lounging opportunities. Wake up every morning to serene water views in this private primary suite with double windows for unobstructed views and French door access to the balcony. The beautiful en-suite has a granite dual sink vanity, walk-in closet, and a garden soaking tub and shower with water views as well! Imagine the relaxing baths you could have here! BR two has cozy carpet and a double door closet with easy access to the hall bath with granite sink vanity and a tub/shower. This is a tranquil community with abundant privacy, but opportunities abound for connection if you’d like. The clubhouse has regular gatherings and events, and the recently refurbished pool and spa are ideal for total relaxation or for connecting with friends. Popular restaurants such as Luke’s, Antonio’s, and Athena’s are found just outside the community and a stone’s throw will land you at Enzian Theater with Eden Bar, the Maitland Art Center, all of the wonderful cultural venues and retail establishments of Winter Park and Orlando, and so much more. Welcome home!

206 Quayside Circle Unit 302, Maitland