$997,000 Tucked at the end of a quiet cul-de-sac beneath a canopy of mature oaks, this beautifully maintained Maitland home offers space, privacy, and thoughtful updates throughout — all within a top school zone just minutes from Winter Park and downtown Orlando. A paver driveway winds through lush, established landscaping to a covered entry framed by an arched transom window, with a tile roof crowning the home. Inside, the open floor plan unfolds around a striking floor-to-ceiling tile fireplace anchoring the family room, with vaulted ceilings, skylights, and French doors that flood the space with natural light and open directly to the screened lanai. The kitchen is a true centerpiece — rich wood cabinetry, granite countertops, a tile backsplash, and stainless steel appliances including a French door refrigerator, all overlooking the family room. A bright, bowed breakfast nook wrapped in windows offers the perfect everyday dining spot, while a separate formal dining room and living room provide room to entertain. This is a true split floor plan, with the primary suite privately tucked away from the secondary bedrooms for maximum peace and quiet. The primary retreat features a spacious layout, built-in bookshelves, and an oversized walk-in closet with custom shelving. The en-suite primary bath features dual vanities, a walk-in glass shower with a bench, and elegant lighting throughout. A versatile bonus room/loft with a full wall of built-in shelving and columned entry adds flexible space for a home office, playroom, or media room. A separate storage loft offers abundant built-in shelving — ideal for keeping everything organized and out of sight. Three additional bedrooms host generous closet space, and a well-appointed powder bath rounds out the main living areas. The oversized utility room impresses with abundant cabinetry, a utility sink, and stone countertops — plenty of room for laundry, storage, and more. Step outside to your own private oasis: a screened, covered lanai wrapping a sparkling pool, all enclosed by mature landscaping and a fully fenced yard — perfect for Florida indoor-outdoor living, entertaining, or simply relaxing under the trees. Located in a sought-after Maitland neighborhood with easy access to top-rated schools, shopping, dining, and major roadways. 4 Beds ⋅ 4 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code Tucked at the end of a quiet cul-de-sac beneath a canopy of mature oaks, this beautifully maintained Maitland home offers space, privacy, and thoughtful updates throughout — all within a top school zone just minutes from Winter Park and downtown Orlando. A paver driveway winds through lush, established landscaping to a covered entry framed by an arched transom window, with a tile roof crowning the home. Inside, the open floor plan unfolds around a striking floor-to-ceiling tile fireplace anchoring the family room, with vaulted ceilings, skylights, and French doors that flood the space with natural light and open directly to the screened lanai. The kitchen is a true centerpiece — rich wood cabinetry, granite countertops, a tile backsplash, and stainless steel appliances including a French door refrigerator, all overlooking the family room. A bright, bowed breakfast nook wrapped in windows offers the perfect everyday dining spot, while a separate formal dining room and living room provide room to entertain. This is a true split floor plan, with the primary suite privately tucked away from the secondary bedrooms for maximum peace and quiet. The primary retreat features a spacious layout, built-in bookshelves, and an oversized walk-in closet with custom shelving. The en-suite primary bath features dual vanities, a walk-in glass shower with a bench, and elegant lighting throughout. A versatile bonus room/loft with a full wall of built-in shelving and columned entry adds flexible space for a home office, playroom, or media room. A separate storage loft offers abundant built-in shelving — ideal for keeping everything organized and out of sight. Three additional bedrooms host generous closet space, and a well-appointed powder bath rounds out the main living areas. The oversized utility room impresses with abundant cabinetry, a utility sink, and stone countertops — plenty of room for laundry, storage, and more. Step outside to your own private oasis: a screened, covered lanai wrapping a sparkling pool, all enclosed by mature landscaping and a fully fenced yard — perfect for Florida indoor-outdoor living, entertaining, or simply relaxing under the trees. Located in a sought-after Maitland neighborhood with easy access to top-rated schools, shopping, dining, and major roadways. 1889 Berkeley Court, Maitland
$199,900 Welcome home to this beautifully updated and maintained 2-bedroom, 2-bath corner unit condo at Visconti West in Maitland! Located on the third floor, this light filled home features vaulted ceilings and an open, airy floor plan designed for comfortable living. The spacious primary suite includes an en-suite bathroom, while both bedrooms offer generous walk-in closets. The kitchen and bathrooms feature upgraded granite countertops and luxury vinyl plank flooring throughout the entryway, kitchen and bathrooms. Enjoy your morning coffee or unwind in the evening on the screened balcony. Additional highlights include an in-unit laundry room with washer and dryer, AC unit (2023), and hot water heater (2025). Residents enjoy gated access and resort style amenities including a pool, fitness center, clubhouse, tennis court, basketball court, valet trash pickup Monday through Friday, and a scenic pond and lake. Conveniently located just minutes from I-4, shopping, dining and entertainment, this home offers the perfect blend of style, comfort, and an unbeatable location. 2 Beds ⋅ 2 Baths ⋅ Visconti East SubDv. ⋅ 32751 Zip Code Welcome home to this beautifully updated and maintained 2-bedroom, 2-bath corner unit condo at Visconti West in Maitland! Located on the third floor, this light filled home features vaulted ceilings and an open, airy floor plan designed for comfortable living. The spacious primary suite includes an en-suite bathroom, while both bedrooms offer generous walk-in closets. The kitchen and bathrooms feature upgraded granite countertops and luxury vinyl plank flooring throughout the entryway, kitchen and bathrooms. Enjoy your morning coffee or unwind in the evening on the screened balcony. Additional highlights include an in-unit laundry room with washer and dryer, AC unit (2023), and hot water heater (2025). Residents enjoy gated access and resort style amenities including a pool, fitness center, clubhouse, tennis court, basketball court, valet trash pickup Monday through Friday, and a scenic pond and lake. Conveniently located just minutes from I-4, shopping, dining and entertainment, this home offers the perfect blend of style, comfort, and an unbeatable location. 1475 Lake Shadow Circle Unit 6307, Maitland
$1,150,000 Move-In Ready. Welcome to the Premier community of Maitland Club. The paver walkway and covered front patio lead you into the spacious foyer, featuring the elegant formal living and dining rooms with hardwood floors, crown molding and plantation shutters. The Kitchen features Granite countertops, 42” cabinets and lots of natural light. The warm and inviting family room area offers a woodburning fireplace with built-in shelving and an open floor plan. The 1st Floor Master has a Large Walk-in closet and master bathroom. Separate shower and Granite countertops. Upstairs boasts a Bonus Room, ample built-in storage, and a 5th Bedroom with a large Walk-in closet. Vaulted Ceilings throughout. The Screened Pool, Covered Lanai, and Large Fenced yard are great for entertaining. The community offers tennis and basketball courts and a 24-hour guard gated community. New roof in 2024 ($80,000 value). The carpet in the home was replaced in 2020.New A/C replacement in 2024.Termite bond which is transferable. TV's convey with the home in the living room. Pool has been resurfaced. The master bath and kitchen have been updated. Move-In Ready. This home is located within minutes of downtown Winter Park, Maitland Town Center, shopping, restaurants, hospitals, Genesis Health Club and easy access to I-4. 5 Beds ⋅ 4 Baths ⋅ Maitland Club Rep SubDv. ⋅ 32751 Zip Code Move-In Ready. Welcome to the Premier community of Maitland Club. The paver walkway and covered front patio lead you into the spacious foyer, featuring the elegant formal living and dining rooms with hardwood floors, crown molding and plantation shutters. The Kitchen features Granite countertops, 42” cabinets and lots of natural light. The warm and inviting family room area offers a woodburning fireplace with built-in shelving and an open floor plan. The 1st Floor Master has a Large Walk-in closet and master bathroom. Separate shower and Granite countertops. Upstairs boasts a Bonus Room, ample built-in storage, and a 5th Bedroom with a large Walk-in closet. Vaulted Ceilings throughout. The Screened Pool, Covered Lanai, and Large Fenced yard are great for entertaining. The community offers tennis and basketball courts and a 24-hour guard gated community. New roof in 2024 ($80,000 value). The carpet in the home was replaced in 2020.New A/C replacement in 2024.Termite bond which is transferable. TV's convey with the home in the living room. Pool has been resurfaced. The master bath and kitchen have been updated. Move-In Ready. This home is located within minutes of downtown Winter Park, Maitland Town Center, shopping, restaurants, hospitals, Genesis Health Club and easy access to I-4. 900 Brightwater Circle, Maitland
$440,000 Under contract-accepting backup offers. Inside, the home opens into a bright and airy open-concept living space highlighted by high tray ceilings, recessed lighting, oversized glossy tile flooring, and an abundance of natural light. The seamless flow between the living, dining, and kitchen areas creates the perfect setting for both entertaining and everyday luxury living. 3 Beds ⋅ 2 Baths ⋅ Pindar Sub SubDv. ⋅ 32751 Zip Code Under contract-accepting backup offers. Inside, the home opens into a bright and airy open-concept living space highlighted by high tray ceilings, recessed lighting, oversized glossy tile flooring, and an abundance of natural light. The seamless flow between the living, dining, and kitchen areas creates the perfect setting for both entertaining and everyday luxury living. 206 Moseley Avenue, Maitland
$485,000 Welcome to this beautifully maintained lakefront townhome in a highly desirable gated community in Maitland with almost 1900 square feet of thoughtfully designed living space. This 3-bedroom, 2.5-bath residence combines comfort, functionality, and picturesque lake views. Enjoy serene views of Lake Charity from the charming front porch, formal dining room, and two upstairs bedrooms. Soaring ceilings and abundant natural light create an airy, inviting atmosphere throughout the home. The spacious open-concept kitchen overlooks the family room and features ample counter seating for barstools, generous cabinetry, and a nice pantry. A private courtyard provides a welcoming outdoor retreat and leads to the oversized 2-car garage with abundant attic storage above. The separate dining room offers a perfect setting for entertaining while enjoying tranquil lake views. A convenient guest bathroom is located on the first floor as well. Upstairs, the massive Primary suite serves as a true retreat, featuring a custom walk-in closet and a spa-inspired en-suite bath with a soaking tub, separate shower, and dual vanities. Two additional bedrooms have stunning views of the lake. One includes a Murphy bed with beautiful built-ins and a custom closet. Another full bath, and a spacious laundry room with plenty of storage complete the second floor. The reasonable HOA fee includes use of the sparkling pool, the secure gate, all landscaping, all maintenance of the exterior of this townhome including the roof, repairs, and paint, and high-speed internet with cable TV, through Spectrum. Offering exceptional space, beautiful water views, and a sought-after gated location, this townhome is the ideal place to call home. *A complimentary complete one-year Home Warranty is provided for extra peace of mind. (A recent Lender's appraisal is also available.) 3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code Welcome to this beautifully maintained lakefront townhome in a highly desirable gated community in Maitland with almost 1900 square feet of thoughtfully designed living space. This 3-bedroom, 2.5-bath residence combines comfort, functionality, and picturesque lake views. Enjoy serene views of Lake Charity from the charming front porch, formal dining room, and two upstairs bedrooms. Soaring ceilings and abundant natural light create an airy, inviting atmosphere throughout the home. The spacious open-concept kitchen overlooks the family room and features ample counter seating for barstools, generous cabinetry, and a nice pantry. A private courtyard provides a welcoming outdoor retreat and leads to the oversized 2-car garage with abundant attic storage above. The separate dining room offers a perfect setting for entertaining while enjoying tranquil lake views. A convenient guest bathroom is located on the first floor as well. Upstairs, the massive Primary suite serves as a true retreat, featuring a custom walk-in closet and a spa-inspired en-suite bath with a soaking tub, separate shower, and dual vanities. Two additional bedrooms have stunning views of the lake. One includes a Murphy bed with beautiful built-ins and a custom closet. Another full bath, and a spacious laundry room with plenty of storage complete the second floor. The reasonable HOA fee includes use of the sparkling pool, the secure gate, all landscaping, all maintenance of the exterior of this townhome including the roof, repairs, and paint, and high-speed internet with cable TV, through Spectrum. Offering exceptional space, beautiful water views, and a sought-after gated location, this townhome is the ideal place to call home. *A complimentary complete one-year Home Warranty is provided for extra peace of mind. (A recent Lender's appraisal is also available.) 1106 Charming Street, Maitland
$410,000 Every detail of this home was thoughtfully curated to offer timeless beauty, upscale finishes, and modern functionality. This exceptional property blends contemporary design with everyday comfort, creating the perfect living experiences. The oversized walk-in shower creates a true resort-style experience with floor-to-ceiling marble-inspired tile, frameless glass enclosure, rainfall showerhead, and designer pebble stone flooring that adds texture and tranquility. Natural light pours through the window, enhancing the bright, airy atmosphere while highlighting the glossy porcelain tile floors that flow seamlessly throughout the space. lastly this home has the perfect blend of modern elegance and functionality in this beautifully designed gourmet kitchen. Featuring stunning granite countertops, sleek custom gray shaker cabinetry, and premium stainless-steel appliances, this space was crafted with both style and everyday living in mind. 3 Beds ⋅ 2 Baths ⋅ Pindar Sub SubDv. ⋅ 32751 Zip Code Every detail of this home was thoughtfully curated to offer timeless beauty, upscale finishes, and modern functionality. This exceptional property blends contemporary design with everyday comfort, creating the perfect living experiences. The oversized walk-in shower creates a true resort-style experience with floor-to-ceiling marble-inspired tile, frameless glass enclosure, rainfall showerhead, and designer pebble stone flooring that adds texture and tranquility. Natural light pours through the window, enhancing the bright, airy atmosphere while highlighting the glossy porcelain tile floors that flow seamlessly throughout the space. lastly this home has the perfect blend of modern elegance and functionality in this beautifully designed gourmet kitchen. Featuring stunning granite countertops, sleek custom gray shaker cabinetry, and premium stainless-steel appliances, this space was crafted with both style and everyday living in mind. 200 Moseley Avenue, Maitland
$1,199,000 Now offered below recent appraised value, this exceptional residence combines luxury, location, and outstanding value in one of Maitland's most sought-after enclaves. Pride of ownership shines throughout this beautifully maintained original-owner home tucked away on a quiet cul-de-sac in the gated community of Sybelia Cove. Offering 4 bedrooms, 4 bathrooms, a side-entry 3-car garage, and 3,902 square feet, this spacious residence blends timeless design with thoughtful updates in one of Maitland’s most desirable locations. Inside, soaring ceilings and expansive windows fill the home with natural light, while the family room fireplace and wood flooring throughout the main entertaining spaces adds warmth and character. The functional floor plan features a private downstairs primary suite along with a dedicated office, creating flexibility for both everyday living and working from home. Upstairs, a spacious loft is accompanied by three additional bedrooms and bathrooms. Fresh carpeting in select areas enhances comfort throughout the home. The kitchen has been updated with refreshed cabinetry, countertops, and GE Café stainless steel appliances, flowing seamlessly into the main living spaces designed for entertaining and gathering. Step outside to a screened-in pool and outdoor living area designed for year-round enjoyment while taking advantage of breezes from nearby Lake Sybelia located just behind the home. A brand-new roof (2024) provides additional peace of mind. Located just moments from downtown Maitland’s shops, dining, and parks, this home offers the privacy of gated living with exceptional walkability and convenience. Call today for your private showing. 4 Beds ⋅ 4 Baths ⋅ Lake Sybelia Cove Ph 01 SubDv. ⋅ 32751 Zip Code Now offered below recent appraised value, this exceptional residence combines luxury, location, and outstanding value in one of Maitland's most sought-after enclaves. Pride of ownership shines throughout this beautifully maintained original-owner home tucked away on a quiet cul-de-sac in the gated community of Sybelia Cove. Offering 4 bedrooms, 4 bathrooms, a side-entry 3-car garage, and 3,902 square feet, this spacious residence blends timeless design with thoughtful updates in one of Maitland’s most desirable locations. Inside, soaring ceilings and expansive windows fill the home with natural light, while the family room fireplace and wood flooring throughout the main entertaining spaces adds warmth and character. The functional floor plan features a private downstairs primary suite along with a dedicated office, creating flexibility for both everyday living and working from home. Upstairs, a spacious loft is accompanied by three additional bedrooms and bathrooms. Fresh carpeting in select areas enhances comfort throughout the home. The kitchen has been updated with refreshed cabinetry, countertops, and GE Café stainless steel appliances, flowing seamlessly into the main living spaces designed for entertaining and gathering. Step outside to a screened-in pool and outdoor living area designed for year-round enjoyment while taking advantage of breezes from nearby Lake Sybelia located just behind the home. A brand-new roof (2024) provides additional peace of mind. Located just moments from downtown Maitland’s shops, dining, and parks, this home offers the privacy of gated living with exceptional walkability and convenience. Call today for your private showing. 873 Cranes Court, Maitland
$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
$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
$329,900 Under contract-accepting backup offers. Back on the market through no fault of the property. Recently appraised at $340,000 and inspections were completed without issue. A great opportunity for a qualified buyer seeking a smooth transaction and quick closing. Tucked into one of Maitland's most coveted lakefront enclaves, this beautifully updated townhome sits within a quietly maintained, tree-lined setting with direct access to Lake Destiny, a private community boat ramp, resort-style pool, and tennis courts, all just minutes from I-4, the 414, RDV Sportsplex, and the dining and shopping corridors of Maitland Center. First impressions set a private and secluded tone with a wrought-iron gated courtyard leads to a covered entry porch before you reach the front door. Inside, soaring vaulted ceilings and a dramatic arched transom window above the sliding glass doors flood the main level with natural light, creating an airy, open feel that far exceeds the square footage on paper. Wide-plank tile flooring runs throughout the main living areas, connecting the open living and dining spaces to a thoughtfully updated kitchen featuring white shaker cabinetry with crown accents, solid stone countertops, stainless steel appliances including a French door refrigerator and built-in microwave, pendant lighting above the breakfast bar peninsula, and a subway tile backsplash. The sliding doors open directly to a private screened patio framed by mature landscaping, creating the kind of indoor-outdoor flow that defines Florida living at its best. Upstairs, three generously sized bedrooms each offer ceiling fans, ample closet space, and brand new carpet and paint. The primary suite stands out with a 26ft footprint, two closets including a walk-in, and an ensuite bath featuring dual vanities, a full-wall vanity mirror, and a walk-in shower. Two additional bedrooms and a full bath complete the upper level, with the layout providing genuine separation and privacy between spaces. Back on the main floor, a versatile 9x9 bonus room with indoor laundry handles the day-to-day, and the full-size washer and dryer convey. The big-ticket items are handled: 30-year tile roof replaced in 2023, HVAC installed in 2020, and brushed nickel fixtures updated throughout. The one-car garage with additional driveway parking and the gated courtyard entry give this unit a sense of privacy and security rare in townhome living. Whether you are looking for a low-maintenance primary residence, a lock-and-leave second home, or a smart investment in a well-managed community with real amenities and a lakefront address, this one makes an easy case. 3 Beds ⋅ 3 Baths ⋅ Villas Lake Destiny SubDv. ⋅ 32751 Zip Code Under contract-accepting backup offers. Back on the market through no fault of the property. Recently appraised at $340,000 and inspections were completed without issue. A great opportunity for a qualified buyer seeking a smooth transaction and quick closing. Tucked into one of Maitland's most coveted lakefront enclaves, this beautifully updated townhome sits within a quietly maintained, tree-lined setting with direct access to Lake Destiny, a private community boat ramp, resort-style pool, and tennis courts, all just minutes from I-4, the 414, RDV Sportsplex, and the dining and shopping corridors of Maitland Center. First impressions set a private and secluded tone with a wrought-iron gated courtyard leads to a covered entry porch before you reach the front door. Inside, soaring vaulted ceilings and a dramatic arched transom window above the sliding glass doors flood the main level with natural light, creating an airy, open feel that far exceeds the square footage on paper. Wide-plank tile flooring runs throughout the main living areas, connecting the open living and dining spaces to a thoughtfully updated kitchen featuring white shaker cabinetry with crown accents, solid stone countertops, stainless steel appliances including a French door refrigerator and built-in microwave, pendant lighting above the breakfast bar peninsula, and a subway tile backsplash. The sliding doors open directly to a private screened patio framed by mature landscaping, creating the kind of indoor-outdoor flow that defines Florida living at its best. Upstairs, three generously sized bedrooms each offer ceiling fans, ample closet space, and brand new carpet and paint. The primary suite stands out with a 26ft footprint, two closets including a walk-in, and an ensuite bath featuring dual vanities, a full-wall vanity mirror, and a walk-in shower. Two additional bedrooms and a full bath complete the upper level, with the layout providing genuine separation and privacy between spaces. Back on the main floor, a versatile 9x9 bonus room with indoor laundry handles the day-to-day, and the full-size washer and dryer convey. The big-ticket items are handled: 30-year tile roof replaced in 2023, HVAC installed in 2020, and brushed nickel fixtures updated throughout. The one-car garage with additional driveway parking and the gated courtyard entry give this unit a sense of privacy and security rare in townhome living. Whether you are looking for a low-maintenance primary residence, a lock-and-leave second home, or a smart investment in a well-managed community with real amenities and a lakefront address, this one makes an easy case. 1010 Winderley Place Unit 127, Maitland
$485,000 Welcome to this beautiful Mediterranean-style townhome in the exclusive, gated community of Montacino in Maitland, Florida. Updated 3 bedroom, 2.5 bath home overlooking Lake Charity. Expansive views of the lake are seen from the front porch, two bedrooms and the dining room. Separate dining room with tons of natural light. Open concept kitchen with updated cabinets and stainless steel appliances. The large family room is open to the kitchen for ease of entertaining. Situated between the garage and your back door is an open air, private courtyard. Enjoy a two and a half car garage with full attic for additional storage. The second floor includes three bedrooms, finished laundry with closets that have been professionally customized. Secondary bedroom boasts a Murphy bed for guests with build-in storage. You will enjoy resort style living with the sparkling community pool and tranquil walks along the shores of Lake Charity. Extra guest parking is located just outside the garage. Internet/TV package and lawn care included. Located just 1/4 mile from I-4 and the Maitland Boulevard exchange with easy access to Winter Park, downtown Orlando and Altamonte Springs. Close by is Trelago Market where the new Trader Joes is being built. A must see property. 3 Beds ⋅ 3 Baths ⋅ Enclave/Maitland A-F SubDv. ⋅ 32751 Zip Code Welcome to this beautiful Mediterranean-style townhome in the exclusive, gated community of Montacino in Maitland, Florida. Updated 3 bedroom, 2.5 bath home overlooking Lake Charity. Expansive views of the lake are seen from the front porch, two bedrooms and the dining room. Separate dining room with tons of natural light. Open concept kitchen with updated cabinets and stainless steel appliances. The large family room is open to the kitchen for ease of entertaining. Situated between the garage and your back door is an open air, private courtyard. Enjoy a two and a half car garage with full attic for additional storage. The second floor includes three bedrooms, finished laundry with closets that have been professionally customized. Secondary bedroom boasts a Murphy bed for guests with build-in storage. You will enjoy resort style living with the sparkling community pool and tranquil walks along the shores of Lake Charity. Extra guest parking is located just outside the garage. Internet/TV package and lawn care included. Located just 1/4 mile from I-4 and the Maitland Boulevard exchange with easy access to Winter Park, downtown Orlando and Altamonte Springs. Close by is Trelago Market where the new Trader Joes is being built. A must see property. 1106 Charming Street, Maitland
$725,000 Virtually Staged. Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid maple wood floors and a light, airy feel that carries throughout the home. To the right, the formal living room features built-in shelving and a striking brick wood-burning fireplace, while the adjoining formal dining room connects directly to the kitchen and can be closed off with pocket doors if you want a little separation. The eat-in kitchen is truly the heart of the home, showcasing rich solid cherry cabinetry, unique man-made glass countertops, a large farmhouse sink, and top-of-the-line stainless Bosch appliances including a built-in oven and gas cooktop. A generous peninsula overlooks the oversized family room, where French doors open to a stunning Florida room that fills the home with natural light. This space is a showstopper—large, lined with windows, and finished with soaring shiplap ceilings—creating the kind of room you’ll use year-round, with direct access to the backyard. The primary suite is spacious and refined with crown molding, a built-in closet plus a walk-in, and a beautifully renovated bath featuring matching glass countertops, a Kohler vanity, and a glass shower with both a large rain head and handheld fixture. Two additional bedrooms are generously sized and share an updated hall bath with a large vanity, classic subway tile, and a soaking tub. The interior also includes a well-equipped laundry room with cabinetry, a cedar storage closet, and access to the two-car garage. Out back, the fully fenced private yard offers plenty of room for entertainment, recently re-sodded with irrigation and enclosed with a brand new wood fence installed in 2025—leaving ample space for a future pool or patio if desired. Additional upgrades include smooth flat ceilings with recessed lighting throughout, new drywall, plantation shutters, updated windows and doors, and an energy-efficient hybrid water heater. Beyond the home itself, the location is hard to beat—just a short walk to Dommerich Elementary, Maitland Middle School, and Maitland Community Park offering tennis courts, indoor racquetball, and playgrounds. Zoned for highly regarded Winter Park High School. Call today to schedule your private showing! 3 Beds ⋅ 2 Baths ⋅ Highland Park Ests SubDv. ⋅ 32751 Zip Code Virtually Staged. Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid maple wood floors and a light, airy feel that carries throughout the home. To the right, the formal living room features built-in shelving and a striking brick wood-burning fireplace, while the adjoining formal dining room connects directly to the kitchen and can be closed off with pocket doors if you want a little separation. The eat-in kitchen is truly the heart of the home, showcasing rich solid cherry cabinetry, unique man-made glass countertops, a large farmhouse sink, and top-of-the-line stainless Bosch appliances including a built-in oven and gas cooktop. A generous peninsula overlooks the oversized family room, where French doors open to a stunning Florida room that fills the home with natural light. This space is a showstopper—large, lined with windows, and finished with soaring shiplap ceilings—creating the kind of room you’ll use year-round, with direct access to the backyard. The primary suite is spacious and refined with crown molding, a built-in closet plus a walk-in, and a beautifully renovated bath featuring matching glass countertops, a Kohler vanity, and a glass shower with both a large rain head and handheld fixture. Two additional bedrooms are generously sized and share an updated hall bath with a large vanity, classic subway tile, and a soaking tub. The interior also includes a well-equipped laundry room with cabinetry, a cedar storage closet, and access to the two-car garage. Out back, the fully fenced private yard offers plenty of room for entertainment, recently re-sodded with irrigation and enclosed with a brand new wood fence installed in 2025—leaving ample space for a future pool or patio if desired. Additional upgrades include smooth flat ceilings with recessed lighting throughout, new drywall, plantation shutters, updated windows and doors, and an energy-efficient hybrid water heater. Beyond the home itself, the location is hard to beat—just a short walk to Dommerich Elementary, Maitland Middle School, and Maitland Community Park offering tennis courts, indoor racquetball, and playgrounds. Zoned for highly regarded Winter Park High School. Call today to schedule your private showing! 2040 Geronimo Trail, 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
$1,199,500 Welcome home to one of the best-kept Maitland secrets, the neighborhood of Wellington. This lakefront home enjoys over 125 feet of linear frontage on Lake of Woods, a spring-fed skiable lake. Home is nearly 3,200 square feet, four bedrooms, three baths with incredible sunset views. Home is spacious with a first-floor primary suite and other bedrooms upstairs with generous flex space. Living space features a wood-burning fireplace with a vaulted ceiling and wood beam architectural accents. Two separate covered porches and screened pool make entertaining a breeze. Other features include solar power energy system (paid in full), newer roof, 2024 air conditioner, updated Hardie board siding, new windows, leaf guard gutter system, replumbed and more. This location is pristine close to many amenities and major roadways. This is a unique opportunity to enjoy lake life at its best. 5 Beds ⋅ 4 Baths ⋅ Wellington SubDv. ⋅ 32751 Zip Code Welcome home to one of the best-kept Maitland secrets, the neighborhood of Wellington. This lakefront home enjoys over 125 feet of linear frontage on Lake of Woods, a spring-fed skiable lake. Home is nearly 3,200 square feet, four bedrooms, three baths with incredible sunset views. Home is spacious with a first-floor primary suite and other bedrooms upstairs with generous flex space. Living space features a wood-burning fireplace with a vaulted ceiling and wood beam architectural accents. Two separate covered porches and screened pool make entertaining a breeze. Other features include solar power energy system (paid in full), newer roof, 2024 air conditioner, updated Hardie board siding, new windows, leaf guard gutter system, replumbed and more. This location is pristine close to many amenities and major roadways. This is a unique opportunity to enjoy lake life at its best. 1232 Wellington Terrace, Maitland
$1,100,000 Nestled in the QUIET, oak tree lined and GATED community of LAKE SYBELIA COVE, this CUSTOM-built TUSCAN-style home offers a respite from the outside world and over 3,000 sq. ft of incredibly beautiful and tranquil living space along with the convenience of daily walks around Lake Sybelia. This IMMACULATE 4-bedroom, 3.5-bath residence features thoughtful design and QUALITY CRAFTSMANSHIP throughout. The GOURMET KITCHEN is equipped with custom cabinetry, granite countertops, an onyx backsplash, a GAS cooktop, and stainless steel appliances, including premium additions like a Viking FRENCH DOOR wall oven, Wolf steam oven, and Bosch dishwasher. On the main floor, the primary suite provides convenience and privacy, along with a second bedroom and full bath. Upstairs, two additional bedrooms each open to private BALCONIES—one offering an impressive VIEW of LAKE SYBELIA. Elegant tray ceilings with crown molding accent the living room, dining room, and primary bedroom. Marble tile flooring flow seamlessly throughout the home, complemented by red oak stairs with wrought iron railings and wide 7.5-inch baseboards. Built for comfort and efficiency, the home includes a RADIANT BARRIER for energy savings, foam-insulated masonry walls on the first floor for better insulation and sound reduction, a whole-house water filtration system, and a GAS water heater. Outdoor spaces include a screened back patio, updated balconies with new drains and flooring, front porch pavers, French drains, and gutters on both the front and back.Recent updates ensure the home is move-in ready. Here are a few of the most recent improvements. NEW tile roof (2023), Exterior painting (2023), Marble flooring installation (2023), Interior painting (2024), Upstairs and downstairs Carrier heat pump HVAC systems (2024 and 2025). Additional enhancements from prior years include CUSTOM front doors and Plantation Shutters on all windows. Located in an excellent school district and just 3 miles from the RDV Sportsplex, this home is conveniently close to the dining, shopping, and all the cultural amenities of MAITLAND and nearby WINTER PARK. Make sure to see the attached video and 3D VIRTUAL Walk Through. 4 Beds ⋅ 4 Baths ⋅ Lake Sybelia Cove Ph 01 SubDv. ⋅ 32751 Zip Code Nestled in the QUIET, oak tree lined and GATED community of LAKE SYBELIA COVE, this CUSTOM-built TUSCAN-style home offers a respite from the outside world and over 3,000 sq. ft of incredibly beautiful and tranquil living space along with the convenience of daily walks around Lake Sybelia. This IMMACULATE 4-bedroom, 3.5-bath residence features thoughtful design and QUALITY CRAFTSMANSHIP throughout. The GOURMET KITCHEN is equipped with custom cabinetry, granite countertops, an onyx backsplash, a GAS cooktop, and stainless steel appliances, including premium additions like a Viking FRENCH DOOR wall oven, Wolf steam oven, and Bosch dishwasher. On the main floor, the primary suite provides convenience and privacy, along with a second bedroom and full bath. Upstairs, two additional bedrooms each open to private BALCONIES—one offering an impressive VIEW of LAKE SYBELIA. Elegant tray ceilings with crown molding accent the living room, dining room, and primary bedroom. Marble tile flooring flow seamlessly throughout the home, complemented by red oak stairs with wrought iron railings and wide 7.5-inch baseboards. Built for comfort and efficiency, the home includes a RADIANT BARRIER for energy savings, foam-insulated masonry walls on the first floor for better insulation and sound reduction, a whole-house water filtration system, and a GAS water heater. Outdoor spaces include a screened back patio, updated balconies with new drains and flooring, front porch pavers, French drains, and gutters on both the front and back.Recent updates ensure the home is move-in ready. Here are a few of the most recent improvements. NEW tile roof (2023), Exterior painting (2023), Marble flooring installation (2023), Interior painting (2024), Upstairs and downstairs Carrier heat pump HVAC systems (2024 and 2025). Additional enhancements from prior years include CUSTOM front doors and Plantation Shutters on all windows. Located in an excellent school district and just 3 miles from the RDV Sportsplex, this home is conveniently close to the dining, shopping, and all the cultural amenities of MAITLAND and nearby WINTER PARK. Make sure to see the attached video and 3D VIRTUAL Walk Through. 890 Cranes Court, Maitland
$900,000 Tucked into prestigious Maitland Florida on coveted Druid Road, this one-of-a-kind residence offers the kind of flexibility—and lifestyle—that’s hard to find and even harder to forget. With 5 bedrooms and 4 full baths, this meticulously cared-for property is designed to fit real life beautifully: a 4-bedroom, 3-bath main home, plus a private 1-bedroom, 1-bath apartment with a brand-new kitchen and its own separate entrance—perfect for guests, multi-generational living, a home office suite, or income potential. Step inside and feel the difference immediately. Freshly painted and thoughtfully updated, the home shines with new flooring, new lighting with sleek LEDs, and a layout that gives everyone room to breathe. The heart of the home is the recently remodeled chef’s kitchen—a true culinary showpiece with high-end appliances, a large island, and modern finishes that make everyday meals and entertaining feel effortless. Beyond the primary living space, a versatile secondary living room invites you to create your ideal retreat—cozy lounge, media room, game room, or quiet escape. And the upgrades go well beyond what you can see: enjoy the peace of mind and efficiency of paid-off solar panels, plus two whole-home water filtration systems with reverse osmosis for crisp, clean water throughout. Outside, the magic continues. The home opens to a private backyard oasis where the sound of a waterfall sets the tone, koi fish glide below, and gatherings naturally gravitate to the outdoor kitchen—perfect for effortless entertaining. Then, tucked away in a second outdoor living space, you’ll find the ultimate wellness setup: a pergola, cold plunge, and sauna, and an outdoor shower creating a true healthy living retreat right in your own backyard. If you’ve been waiting for a home that feels special—updated, versatile, energy-smart, and built for both connection and calm—this Maitland gem is the one. 5 Beds ⋅ 4 Baths ⋅ Druid Hills SubDv. ⋅ 32751 Zip Code Tucked into prestigious Maitland Florida on coveted Druid Road, this one-of-a-kind residence offers the kind of flexibility—and lifestyle—that’s hard to find and even harder to forget. With 5 bedrooms and 4 full baths, this meticulously cared-for property is designed to fit real life beautifully: a 4-bedroom, 3-bath main home, plus a private 1-bedroom, 1-bath apartment with a brand-new kitchen and its own separate entrance—perfect for guests, multi-generational living, a home office suite, or income potential. Step inside and feel the difference immediately. Freshly painted and thoughtfully updated, the home shines with new flooring, new lighting with sleek LEDs, and a layout that gives everyone room to breathe. The heart of the home is the recently remodeled chef’s kitchen—a true culinary showpiece with high-end appliances, a large island, and modern finishes that make everyday meals and entertaining feel effortless. Beyond the primary living space, a versatile secondary living room invites you to create your ideal retreat—cozy lounge, media room, game room, or quiet escape. And the upgrades go well beyond what you can see: enjoy the peace of mind and efficiency of paid-off solar panels, plus two whole-home water filtration systems with reverse osmosis for crisp, clean water throughout. Outside, the magic continues. The home opens to a private backyard oasis where the sound of a waterfall sets the tone, koi fish glide below, and gatherings naturally gravitate to the outdoor kitchen—perfect for effortless entertaining. Then, tucked away in a second outdoor living space, you’ll find the ultimate wellness setup: a pergola, cold plunge, and sauna, and an outdoor shower creating a true healthy living retreat right in your own backyard. If you’ve been waiting for a home that feels special—updated, versatile, energy-smart, and built for both connection and calm—this Maitland gem is the one. 1619 Druid Road, Maitland
$4,999,000 Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida. 5 Beds ⋅ 8 Baths ⋅ Floridahaven SubDv. ⋅ 32751 Zip Code Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida. 360 Lake Seminary Circle, Maitland
$255,000 Great Maitland single family home located on a quiet cul-de-sac close to shopping, restaurants, all major highways and great schools!!! This 3 bedroom 2 bathroom home also features a Florida room with fireplace, LARGE fenced yard, 2 car carport, utility storage room with washer/dryer hookup and much more. This property has been freshly painted inside and is ready for the new owner to make it shine again! Do not miss your opportunity on this one, call for your private showing today!!! 3 Beds ⋅ 2 Baths ⋅ Lakewood Shores 1st Add SubDv. ⋅ 32751 Zip Code Great Maitland single family home located on a quiet cul-de-sac close to shopping, restaurants, all major highways and great schools!!! This 3 bedroom 2 bathroom home also features a Florida room with fireplace, LARGE fenced yard, 2 car carport, utility storage room with washer/dryer hookup and much more. This property has been freshly painted inside and is ready for the new owner to make it shine again! Do not miss your opportunity on this one, call for your private showing today!!! 240 Cherrywood Drive, Maitland
$535,000 RARE OPPORTUNITY – Enjoy lakefront living with a PRIVATE BOAT SLIP on the Winter Park chain of lakes in this top-floor penthouse condo. The Moorings on Lake Maitland, one of Central Florida’s most coveted waterfront communities. This spacious 2-bedroom, 2-bath residence offers soaring vaulted ceilings, breathtaking lake views, and your own assigned private boat slip—a rare find on the Winter Park Chain of Lakes. Step inside to an abundance of natural light and a thoughtfully designed floor plan with no upstairs neighbors, ensuring maximum privacy and quiet. The large living area opens to a glass-enclosed sunroom with panoramic views of Lake Maitland—perfect for morning coffee or relaxing at sunset. The kitchen is bright and functional, featuring a breakfast nook and walk-in pantry. The split-bedroom layout offers privacy and flexibility. The primary suite includes a handicap-accessible bath, generous closet space, and tranquil lake views. The guest bedroom and full second bath are perfect for visitors or a home office. The laundry is conveniently located tucked off the main hall, and with custom closets in both bedrooms the amount of storage is great. For larger items the unit includes a locking storage closet on the landing, and is perfect for bikes, golf clubs, holiday decorations etc. The unit comes with one reserved covered parking space and plenty of guest parking. The complex has a newly renovated pool, hot tub & clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this rare top-floor condo offers an unbeatable combination of comfort, convenience, and waterfront access. Live the Florida lake lifestyle—schedule your private showing today! 2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code RARE OPPORTUNITY – Enjoy lakefront living with a PRIVATE BOAT SLIP on the Winter Park chain of lakes in this top-floor penthouse condo. The Moorings on Lake Maitland, one of Central Florida’s most coveted waterfront communities. This spacious 2-bedroom, 2-bath residence offers soaring vaulted ceilings, breathtaking lake views, and your own assigned private boat slip—a rare find on the Winter Park Chain of Lakes. Step inside to an abundance of natural light and a thoughtfully designed floor plan with no upstairs neighbors, ensuring maximum privacy and quiet. The large living area opens to a glass-enclosed sunroom with panoramic views of Lake Maitland—perfect for morning coffee or relaxing at sunset. The kitchen is bright and functional, featuring a breakfast nook and walk-in pantry. The split-bedroom layout offers privacy and flexibility. The primary suite includes a handicap-accessible bath, generous closet space, and tranquil lake views. The guest bedroom and full second bath are perfect for visitors or a home office. The laundry is conveniently located tucked off the main hall, and with custom closets in both bedrooms the amount of storage is great. For larger items the unit includes a locking storage closet on the landing, and is perfect for bikes, golf clubs, holiday decorations etc. The unit comes with one reserved covered parking space and plenty of guest parking. The complex has a newly renovated pool, hot tub & clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this rare top-floor condo offers an unbeatable combination of comfort, convenience, and waterfront access. Live the Florida lake lifestyle—schedule your private showing today! 202 Quayside Circle Unit 404, Maitland
$230,000 This rare 4-bedroom, 2-bath first-floor end-unit condo presents an exceptional opportunity in the gated community of Visconti West in Maitland, Florida—perfect timing for holiday-season buyers. Offering true resort-style living with the convenience of ground-floor access, this light-filled home features an open, functional floor plan designed for comfort and flexibility. Inside, you’ll find luxury vinyl plank flooring, 5-inch baseboards, and freshly painted interiors that create a clean, modern feel throughout. The updated kitchen includes newer countertops, sink, and disposal, while the primary bathroom has been tastefully refreshed with a modern vanity, classic subway tile, updated lighting, and a new toilet—making this condo truly move-in ready. Enjoy low-maintenance living with outstanding community amenities just steps away, including a resort-style swimming pool, scenic walking paths with tranquil lake views, a fully equipped fitness center, tennis courts, and basketball courts. Whether you’re starting your day with a walk by the water or unwinding poolside, Visconti West offers a lifestyle that feels like a vacation year-round. Ideally located in Maitland, this condo is minutes from shopping, dining, major roadways, and everything Central Florida has to offer. With its rare 4-bedroom layout, first-floor end-unit location, recent upgrades, and new attractive price, this home is an excellent option for a primary residence, second home, or investment property. Schedule your private showing today and take advantage of this value-packed opportunity before the holidays pass. 4 Beds ⋅ 2 Baths ⋅ Visconti West Condominium SubDv. ⋅ 32751 Zip Code This rare 4-bedroom, 2-bath first-floor end-unit condo presents an exceptional opportunity in the gated community of Visconti West in Maitland, Florida—perfect timing for holiday-season buyers. Offering true resort-style living with the convenience of ground-floor access, this light-filled home features an open, functional floor plan designed for comfort and flexibility. Inside, you’ll find luxury vinyl plank flooring, 5-inch baseboards, and freshly painted interiors that create a clean, modern feel throughout. The updated kitchen includes newer countertops, sink, and disposal, while the primary bathroom has been tastefully refreshed with a modern vanity, classic subway tile, updated lighting, and a new toilet—making this condo truly move-in ready. Enjoy low-maintenance living with outstanding community amenities just steps away, including a resort-style swimming pool, scenic walking paths with tranquil lake views, a fully equipped fitness center, tennis courts, and basketball courts. Whether you’re starting your day with a walk by the water or unwinding poolside, Visconti West offers a lifestyle that feels like a vacation year-round. Ideally located in Maitland, this condo is minutes from shopping, dining, major roadways, and everything Central Florida has to offer. With its rare 4-bedroom layout, first-floor end-unit location, recent upgrades, and new attractive price, this home is an excellent option for a primary residence, second home, or investment property. Schedule your private showing today and take advantage of this value-packed opportunity before the holidays pass. 1460 Lake Shadow Circle Unit 7107, Maitland
$939,000 Under contract-accepting backup offers. Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along a peaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and privacy. Re-roofed in 2023, this expansive 5 bedroom, 3 1/2 bath residence offers 4,144 HSF, and WHOLE HOUSE WATER SOFTNER, showcases a versatile TWO-LEVEL design, perfectly suited for refined living and gracious entertaining. The main level opens with a foyer leading into a bright, open living and dining area, where CEILING FANS throughout the main level add comfort and elegance. From here, step out onto the COVERED UPPER DECK with sweeping views of the SCREENED POOL, TROPICAL GARDEN, and serene backyard retreat - an ideal setting for morning coffee or evening gatherings. At the heart of the home, the GOURMET KITCHEN blends style and functionality with SOLID WOOD CABINETRY, a built-in WINE REFRIGERATOR and WINE RACK, granite countertops, and a CENTER ISLAND with SEATING, and REVERSE OSMOSIS WATER SYSTEM under the DOUBLE SINK. The adjacent laundry room offers exceptional storage, keeping household essentials organized. For added convenience , a two-car garage with built-in cabinets and workshop area, adjoins the spacious laundry room that has granite counters and washer and dryer. Also on the main level , adjacent to the primary bedroom with en-suite bath, a bedroom has been thoughtfully converted into a large closet featuring a CUSTOM CLOSET system, providing abundant space for wardrobe organization. Both levels feature inviting WOOD-BURNING FIREPLACES that add ambiance to the living spaces. On the lower level, a spacious family room, kitchenette, study/library/office, two bedrooms, full bath and half bath provide the perfect complement to easy living. Along the hallway, built-in wood shelving creates a refined showcase for books, art, or personal collections. While one bedroom includes a custom built in desk- ideal for work or study, a second bedroom adds flexibility for creative projects. This level opens onto the screened pool and patio area, designed for seamless indoor-outdoor living. Outside, tropical plantings, METERED IRRIGATION, and a winding private walkway leads along the soft murmur of the BORDERING CREEK. An added bonus is the storage room located below the kitchen which is approximately 375 sq.ft. Whether hosting guests or enjoying a quiet evening, this private oasis offers the ultimate backdrop for relaxed Florida living. Enjoy the opportunity to join the Dommerich Beach Civic Association with membership options including access to a private picnic area, boat ramp, canoe and kayak storage, and unforgettable evening sunsets. With its rare combination of design, flexible spaces, and an idyllic setting , this residence presents a unique opportunity to experience the very best of Maitland and Central Florida living. All this is convenient to some of Central Florida's finest schools, shopping, restaurants, parks, entertainment, businesses and more! 5 Beds ⋅ 4 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code Under contract-accepting backup offers. Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along a peaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and privacy. Re-roofed in 2023, this expansive 5 bedroom, 3 1/2 bath residence offers 4,144 HSF, and WHOLE HOUSE WATER SOFTNER, showcases a versatile TWO-LEVEL design, perfectly suited for refined living and gracious entertaining. The main level opens with a foyer leading into a bright, open living and dining area, where CEILING FANS throughout the main level add comfort and elegance. From here, step out onto the COVERED UPPER DECK with sweeping views of the SCREENED POOL, TROPICAL GARDEN, and serene backyard retreat - an ideal setting for morning coffee or evening gatherings. At the heart of the home, the GOURMET KITCHEN blends style and functionality with SOLID WOOD CABINETRY, a built-in WINE REFRIGERATOR and WINE RACK, granite countertops, and a CENTER ISLAND with SEATING, and REVERSE OSMOSIS WATER SYSTEM under the DOUBLE SINK. The adjacent laundry room offers exceptional storage, keeping household essentials organized. For added convenience , a two-car garage with built-in cabinets and workshop area, adjoins the spacious laundry room that has granite counters and washer and dryer. Also on the main level , adjacent to the primary bedroom with en-suite bath, a bedroom has been thoughtfully converted into a large closet featuring a CUSTOM CLOSET system, providing abundant space for wardrobe organization. Both levels feature inviting WOOD-BURNING FIREPLACES that add ambiance to the living spaces. On the lower level, a spacious family room, kitchenette, study/library/office, two bedrooms, full bath and half bath provide the perfect complement to easy living. Along the hallway, built-in wood shelving creates a refined showcase for books, art, or personal collections. While one bedroom includes a custom built in desk- ideal for work or study, a second bedroom adds flexibility for creative projects. This level opens onto the screened pool and patio area, designed for seamless indoor-outdoor living. Outside, tropical plantings, METERED IRRIGATION, and a winding private walkway leads along the soft murmur of the BORDERING CREEK. An added bonus is the storage room located below the kitchen which is approximately 375 sq.ft. Whether hosting guests or enjoying a quiet evening, this private oasis offers the ultimate backdrop for relaxed Florida living. Enjoy the opportunity to join the Dommerich Beach Civic Association with membership options including access to a private picnic area, boat ramp, canoe and kayak storage, and unforgettable evening sunsets. With its rare combination of design, flexible spaces, and an idyllic setting , this residence presents a unique opportunity to experience the very best of Maitland and Central Florida living. All this is convenient to some of Central Florida's finest schools, shopping, restaurants, parks, entertainment, businesses and more! 791 Sequoia Trail, Maitland
$1,035,000 A truly unique opportunity in the Maitland / Winter Park area, the Maitland Club community features a 24/7 guard-gated entrance for this executive home! This 4 BR, 3.5 BA home has all the features of a dream home, including a downstairs guest/in-law suite with private entry, a large front den for a home office, and a versatile bonus room ideal for a second office, gym, wine room, or hobby space. The renovated chef’s kitchen boasts wood cabinetry, granite counters, stainless steel appliances, an above-range pot filler, island seating, and a 6' x 6' walk-in pantry with custom shelving. Elegant finishes include wood floors throughout, plantation shutters, crown molding, and upgraded millwork. The family room features a cozy fireplace and offers beautiful views of the pool and mature backyard landscaping. The large primary suite showcases a seating area, custom walk-in closet, and remodeled bath with double vanities, beautiful tile work, new cabinetry, and even a window seat. The guest bedrooms on the second floor are generously sized with an updated Jack-and-Jill bath and custom storage solutions built into the closets. Enjoy a private backyard retreat with a resurfaced and heated pool featuring custom lighting, decorative tile, and a relaxing water feature, plus a covered patio and no rear neighbors. Upgrades are countless in this loved home, including ceiling storage and tool cabinets in the oversized 3-car garage, a new roof (2023), replumbed (2022), HVAC replacement (2022), new wood floors, custom closet built-ins, and even fresh paint. Community amenities include tennis, basketball, playground, and proximity to Orangewood PreK-12th grade School with quick access to Winter Park, I-4 Express, and all of Central Florida! Don't miss your chance to claim this dream custom home as your own! 4 Beds ⋅ 4 Baths ⋅ Maitland Club Rep SubDv. ⋅ 32751 Zip Code A truly unique opportunity in the Maitland / Winter Park area, the Maitland Club community features a 24/7 guard-gated entrance for this executive home! This 4 BR, 3.5 BA home has all the features of a dream home, including a downstairs guest/in-law suite with private entry, a large front den for a home office, and a versatile bonus room ideal for a second office, gym, wine room, or hobby space. The renovated chef’s kitchen boasts wood cabinetry, granite counters, stainless steel appliances, an above-range pot filler, island seating, and a 6' x 6' walk-in pantry with custom shelving. Elegant finishes include wood floors throughout, plantation shutters, crown molding, and upgraded millwork. The family room features a cozy fireplace and offers beautiful views of the pool and mature backyard landscaping. The large primary suite showcases a seating area, custom walk-in closet, and remodeled bath with double vanities, beautiful tile work, new cabinetry, and even a window seat. The guest bedrooms on the second floor are generously sized with an updated Jack-and-Jill bath and custom storage solutions built into the closets. Enjoy a private backyard retreat with a resurfaced and heated pool featuring custom lighting, decorative tile, and a relaxing water feature, plus a covered patio and no rear neighbors. Upgrades are countless in this loved home, including ceiling storage and tool cabinets in the oversized 3-car garage, a new roof (2023), replumbed (2022), HVAC replacement (2022), new wood floors, custom closet built-ins, and even fresh paint. Community amenities include tennis, basketball, playground, and proximity to Orangewood PreK-12th grade School with quick access to Winter Park, I-4 Express, and all of Central Florida! Don't miss your chance to claim this dream custom home as your own! 904 Brightwater Circle, Maitland
$500,000 One or more photo(s) has been virtually staged. Located in the heart of Maitland on a quiet cul-de-sac, this 3 bedroom, 2 bath single-story ranch home is a hidden gem. Light and bright with clean lines, this charming, renovated home is in move-in condition. The functional kitchen features stainless steel appliances, tile backsplash, ample cabinetry, a breakfast bar and an adjoining dining area overlooking the living room. With a wall of windows, the spacious living area is the heart of the home. The primary suite includes a walk-in closet, while the ensuite bath showcases a tiled shower updated vanity, lighting and fixtures. Two secondary bedrooms overlook the front yard and share a hall bath with dual sinks and a tub/shower combo. Outdoor living is a delight with an open-air covered patio, built-in grill, and a fenced back yard accented with flowering foliage. There is plenty of room to add a pool. Additional highlights include a long driveway with ample parking, a shed, a storage room off the patio and a whole-home water purification system. Conveniently located near I-4, Winter Park, SunRail, Maitland Farmer's Market and local area restaurants. Recent improvements include a dishwasher and water heater in 2025, 3-ton AC in 2022 and windows in 2020. Septic system to be replaced in September 2025. This property combines charm, function and location in one exceptional package. Welcome home! 3 Beds ⋅ 2 Baths ⋅ Northwood Heights SubDv. ⋅ 32751 Zip Code One or more photo(s) has been virtually staged. Located in the heart of Maitland on a quiet cul-de-sac, this 3 bedroom, 2 bath single-story ranch home is a hidden gem. Light and bright with clean lines, this charming, renovated home is in move-in condition. The functional kitchen features stainless steel appliances, tile backsplash, ample cabinetry, a breakfast bar and an adjoining dining area overlooking the living room. With a wall of windows, the spacious living area is the heart of the home. The primary suite includes a walk-in closet, while the ensuite bath showcases a tiled shower updated vanity, lighting and fixtures. Two secondary bedrooms overlook the front yard and share a hall bath with dual sinks and a tub/shower combo. Outdoor living is a delight with an open-air covered patio, built-in grill, and a fenced back yard accented with flowering foliage. There is plenty of room to add a pool. Additional highlights include a long driveway with ample parking, a shed, a storage room off the patio and a whole-home water purification system. Conveniently located near I-4, Winter Park, SunRail, Maitland Farmer's Market and local area restaurants. Recent improvements include a dishwasher and water heater in 2025, 3-ton AC in 2022 and windows in 2020. Septic system to be replaced in September 2025. This property combines charm, function and location in one exceptional package. Welcome home! 170 E Faith Terrace, Maitland
$2,475,000 The Winter Park Chain is the context; the shoreline of Lake Minnehaha is the setting. A three-story, columned home opens with an honest, crafted tone: new low-profile concrete tile roof, operable cypress shutters with hand-forged hardware, Chippendale balustrades, and a beveled front door offering almost 6,200 sq. ft. curated for light, views, and everyday lake living. Inside, the home is bright and airy—sunlight does the work here. A direct foyer sightline leads you to a rear wall of French doors that draw in a calm, even glow of natural light across heart-of-pine floors and disciplined millwork: raised-panel wainscot, multi-step crown molding, and architectural beams. Those doors open to a full-length covered lanai; beyond, a heated saltwater pool and spa step down to a deep backyard and a private dock with a covered boat slip and adjoining lounge deck. The kitchen is built to perform so life feels easy. Morning coffee, weeknight pasta, Saturday crowds, it handles all of it. Sub-Zero refrigeration with additional refrigerator drawers, a Thermador six-burner gas range, two dishwashers, and a warming drawer. Granite counters surround a prep island with rinse sink; the peninsula takes the laptops and late plates. A dry bar with wine cooler ties to the dining room for effortless pours and keeps glassware close at hand. Just off the family room, the primary suite claims a quiet corner and opens to the lanai; coffee at sunrise, warm light at day’s end. A large custom walk-in closet answers storage; the bath finishes the suite with tumbled marble, Kohler fixtures, and a cast-iron vintage tub. At the center of the first floor, a deliberate service run keeps daily life organized: powder bath, temperature-controlled wine cellar, a straight sightline to the first of two laundry rooms and the garage entry ending at a private interior stair to a secluded in-law/guest suite with its own full bath. It’s independent, quiet, and ideal for long stays or live-in support. The main stair brings you to a second level arranged with intent. One wing holds three bedrooms around a shared bath. An office corridor carries you to the lake-view great room under a coffered ceiling; triple French doors open to the full-length upper veranda. Another bedroom on this wing enjoys its own veranda access with a full bath close by. Above it all, the third floor is a generous, flexible loft fit for a screening room, billiards or game lounge, studio, gym, or a collector’s library with practical storage tucked to the edges. Quiet systems match the craft: Cat-5 wiring, surround sound, central vacuum, and two laundry rooms. Recent updates keep the essentials current: new HVACs (2020, 2021) and a new dock (2024). Zoned for Maitland Middle and Winter Park High, this home is tuned to everyday rhythm: water out back, light throughout, spaces that work the way you live. From lanai shade to the last light on the lake, it delivers on its promise—an honest, crafted place where the architecture serves the life it keeps. 6 Beds ⋅ 6 Baths ⋅ Packwoods Plan/Maitland SubDv. ⋅ 32751 Zip Code The Winter Park Chain is the context; the shoreline of Lake Minnehaha is the setting. A three-story, columned home opens with an honest, crafted tone: new low-profile concrete tile roof, operable cypress shutters with hand-forged hardware, Chippendale balustrades, and a beveled front door offering almost 6,200 sq. ft. curated for light, views, and everyday lake living. Inside, the home is bright and airy—sunlight does the work here. A direct foyer sightline leads you to a rear wall of French doors that draw in a calm, even glow of natural light across heart-of-pine floors and disciplined millwork: raised-panel wainscot, multi-step crown molding, and architectural beams. Those doors open to a full-length covered lanai; beyond, a heated saltwater pool and spa step down to a deep backyard and a private dock with a covered boat slip and adjoining lounge deck. The kitchen is built to perform so life feels easy. Morning coffee, weeknight pasta, Saturday crowds, it handles all of it. Sub-Zero refrigeration with additional refrigerator drawers, a Thermador six-burner gas range, two dishwashers, and a warming drawer. Granite counters surround a prep island with rinse sink; the peninsula takes the laptops and late plates. A dry bar with wine cooler ties to the dining room for effortless pours and keeps glassware close at hand. Just off the family room, the primary suite claims a quiet corner and opens to the lanai; coffee at sunrise, warm light at day’s end. A large custom walk-in closet answers storage; the bath finishes the suite with tumbled marble, Kohler fixtures, and a cast-iron vintage tub. At the center of the first floor, a deliberate service run keeps daily life organized: powder bath, temperature-controlled wine cellar, a straight sightline to the first of two laundry rooms and the garage entry ending at a private interior stair to a secluded in-law/guest suite with its own full bath. It’s independent, quiet, and ideal for long stays or live-in support. The main stair brings you to a second level arranged with intent. One wing holds three bedrooms around a shared bath. An office corridor carries you to the lake-view great room under a coffered ceiling; triple French doors open to the full-length upper veranda. Another bedroom on this wing enjoys its own veranda access with a full bath close by. Above it all, the third floor is a generous, flexible loft fit for a screening room, billiards or game lounge, studio, gym, or a collector’s library with practical storage tucked to the edges. Quiet systems match the craft: Cat-5 wiring, surround sound, central vacuum, and two laundry rooms. Recent updates keep the essentials current: new HVACs (2020, 2021) and a new dock (2024). Zoned for Maitland Middle and Winter Park High, this home is tuned to everyday rhythm: water out back, light throughout, spaces that work the way you live. From lanai shade to the last light on the lake, it delivers on its promise—an honest, crafted place where the architecture serves the life it keeps. 604 Minnehaha Lane, Maitland
$515,000 Here's your chance to own an amazing penthouse condo in the sought after community, "The Moorings on Lake Maitland". Stunning high-end updates to this corner unit with vaulted ceilings and breath taking lake views include, wood floors, custom moldings and millwork, plantation shutters, completely updated kitchen (which has been redesigned to expand into the living space), solid wood cabinetry, Australian quartzite counters, mosaic backsplash, GE Profile SS appliances and an eat-in nook. The glassed-in lanai adds even more to the living space with gorgeous views of the early morning sunrise and evening moonrise over Lake Maitland, part the Winter Park Chain of Lakes. Split bedroom plan provides maximum privacy. Primary suite which opens to the lanai has fully updated bath, dual sinks, step-in shower and a spacious walk-in closet. Fully equipped laundry room, and updated spacious guest bath. So many wonderful details including lots of storage in the custom designed closets throughout and a storage room just outside the unit on the landing, within close proximity to the elevator. New AC in 2021, Reroof 2021, Structural Weatherproofing 2022, Assigned Covered Parking Space, Pool, Spa & Club House Updates. ALL THIS & walkabililty to countless restaurants and shopping!! Schedule a showing now! This one won't last! 2 Beds ⋅ 2 Baths ⋅ Moorings On Lake Maitland Condo SubDv. ⋅ 32751 Zip Code Here's your chance to own an amazing penthouse condo in the sought after community, "The Moorings on Lake Maitland". Stunning high-end updates to this corner unit with vaulted ceilings and breath taking lake views include, wood floors, custom moldings and millwork, plantation shutters, completely updated kitchen (which has been redesigned to expand into the living space), solid wood cabinetry, Australian quartzite counters, mosaic backsplash, GE Profile SS appliances and an eat-in nook. The glassed-in lanai adds even more to the living space with gorgeous views of the early morning sunrise and evening moonrise over Lake Maitland, part the Winter Park Chain of Lakes. Split bedroom plan provides maximum privacy. Primary suite which opens to the lanai has fully updated bath, dual sinks, step-in shower and a spacious walk-in closet. Fully equipped laundry room, and updated spacious guest bath. So many wonderful details including lots of storage in the custom designed closets throughout and a storage room just outside the unit on the landing, within close proximity to the elevator. New AC in 2021, Reroof 2021, Structural Weatherproofing 2022, Assigned Covered Parking Space, Pool, Spa & Club House Updates. ALL THIS & walkabililty to countless restaurants and shopping!! Schedule a showing now! This one won't last! 204 Quayside Circle Unit 601, Maitland
$8,925,000 Villa Serenata, a lakefront legacy on Lake Maitland. Behind private iron gates along the storied shores of Lake Maitland, Villa Serenata presents a rare opportunity to own a distinguished Mediterranean estate on the renowned Winter Park Chain of Lakes. On approximately two acres of meticulously curated grounds, this extraordinary residence feels less like a home and more like a private resort, crafted for those who appreciate timeless architecture, thoughtful design and elevated lakefront living. A sweeping circular driveway welcomes you beneath a canopy of soaring royal palms and majestic live oaks, immediately setting the tone for what lies beyond. As the automated gate opens, the property reveals itself as a serene sanctuary where elegance and privacy coexist in harmony. The 6,634-square-foot main residence showcases interiors by acclaimed designer Ted Maines, unfolding across two levels of refined sophistication. The Mizner-inspired living room commands attention with dramatic 24-foot wood-beamed ceilings and twin walls of arched French doors, one framing sweeping views of Lake Maitland’s shimmering waters, the other opening to a sun-dappled courtyard where mornings naturally begin with coffee and quiet reflection. The upper level is devoted entirely to the primary suite, creating a private retreat complete with a heatless gas fireplace, spa-caliber bath with soaking tub and steam shower, a bespoke dressing room with custom built-ins, and a rooftop terrace with glass railings offering remarkable lake views. Three additional bedroom suites, each with an en-suite bath and generous walk-in closet, provide comfort and privacy for family and guests alike. At the heart of the home, the chef’s kitchen is equipped with Sub-Zero and Wolf appliances, custom cabinetry, and an expansive prep island designed to transition seamlessly from intimate family meals to catered gatherings of 50. The formal dining room features a dramatic curved wall of windows, turning every meal into a lakefront experience, while the richly paneled library and office offer a quiet space for focused work or relaxed reading. Complementing the main residence is a thoughtfully designed guest compound totaling 1,540 square feet. A private media pavilion delivers a state-of-the-art theater and listening room for film enthusiasts and audiophiles, while the one-bedroom guest apartment above provides a fully appointed living space with kitchen, living area and private entry, ideal for extended family, visiting guests or live-in staff. Outdoor living is equally exceptional. Resort-style travertine surrounds the pool amid lush tropical landscaping, creating a tranquil setting for sun-filled afternoons. A covered lanai with full summer kitchen flows effortlessly from the family room, while an expansive open-air terrace extends from the great room, an inviting backdrop for sunset cocktails overlooking the lake. Villa Serenata is more than a residence, it is a legacy estate, offering privacy, architectural distinction, and a lifestyle centered on one of Winter Park’s treasured waterfront settings. 5 Beds ⋅ 8 Baths ⋅ Adams Grove SubDv. ⋅ 32751 Zip Code Villa Serenata, a lakefront legacy on Lake Maitland. Behind private iron gates along the storied shores of Lake Maitland, Villa Serenata presents a rare opportunity to own a distinguished Mediterranean estate on the renowned Winter Park Chain of Lakes. On approximately two acres of meticulously curated grounds, this extraordinary residence feels less like a home and more like a private resort, crafted for those who appreciate timeless architecture, thoughtful design and elevated lakefront living. A sweeping circular driveway welcomes you beneath a canopy of soaring royal palms and majestic live oaks, immediately setting the tone for what lies beyond. As the automated gate opens, the property reveals itself as a serene sanctuary where elegance and privacy coexist in harmony. The 6,634-square-foot main residence showcases interiors by acclaimed designer Ted Maines, unfolding across two levels of refined sophistication. The Mizner-inspired living room commands attention with dramatic 24-foot wood-beamed ceilings and twin walls of arched French doors, one framing sweeping views of Lake Maitland’s shimmering waters, the other opening to a sun-dappled courtyard where mornings naturally begin with coffee and quiet reflection. The upper level is devoted entirely to the primary suite, creating a private retreat complete with a heatless gas fireplace, spa-caliber bath with soaking tub and steam shower, a bespoke dressing room with custom built-ins, and a rooftop terrace with glass railings offering remarkable lake views. Three additional bedroom suites, each with an en-suite bath and generous walk-in closet, provide comfort and privacy for family and guests alike. At the heart of the home, the chef’s kitchen is equipped with Sub-Zero and Wolf appliances, custom cabinetry, and an expansive prep island designed to transition seamlessly from intimate family meals to catered gatherings of 50. The formal dining room features a dramatic curved wall of windows, turning every meal into a lakefront experience, while the richly paneled library and office offer a quiet space for focused work or relaxed reading. Complementing the main residence is a thoughtfully designed guest compound totaling 1,540 square feet. A private media pavilion delivers a state-of-the-art theater and listening room for film enthusiasts and audiophiles, while the one-bedroom guest apartment above provides a fully appointed living space with kitchen, living area and private entry, ideal for extended family, visiting guests or live-in staff. Outdoor living is equally exceptional. Resort-style travertine surrounds the pool amid lush tropical landscaping, creating a tranquil setting for sun-filled afternoons. A covered lanai with full summer kitchen flows effortlessly from the family room, while an expansive open-air terrace extends from the great room, an inviting backdrop for sunset cocktails overlooking the lake. Villa Serenata is more than a residence, it is a legacy estate, offering privacy, architectural distinction, and a lifestyle centered on one of Winter Park’s treasured waterfront settings. 1640 E Adams Drive, Maitland
$725,000 Renovated Maitland Gem with newer pool, move-In ready! Tucked away in a peaceful Maitland neighborhood, this beautifully updated one-story home offers a blend of style, comfort and convenience. With three bedrooms, two baths and 1,760 square feet of thoughtfully designed living space, this property is a hidden gem. Enjoy unbeatable curb appeal with lush landscaping, newer windows/doors, a lighted walkway to the front door, and a welcoming open front deck with a stylish, modern privacy wall. The oversized brick paver driveway adds charm and functionality. Inside, tile flooring flows seamlessly throughout the entire home, enhancing its clean, cohesive look. Plantation shutters and designer lighting add a refined touch to every room, while custom closet systems maximize storage in all bedrooms. The open-concept kitchen is a dream for everyday living and entertaining, featuring soft-close cabinets and drawers, bar seating and a cozy breakfast nook. It overlooks the spacious great room and dining area, both adorned with large picture windows that frame serene views of the backyard and pool. The primary suite offers a relaxing retreat with a walk-in closet and a beautifully updated en-suite bath with a large glass-enclosed shower. Two additional bedrooms and a spacious laundry room complete the smartly designed layout. Go outside to your private backyard oasis, fully fenced for privacy and beautifully landscaped to create a picturesque setting. A sparkling, heated/saltwater pool invites you to unwind or entertain, while the generous green space provides ample room for outdoor games, gardening, pets or future enhancements. The covered patio is ideal for alfresco dining, morning coffee or simply enjoying the Florida sunshine in your tranquil retreat. Additional features include a one-car garage with a large storage room and additional refrigerator. Just minutes from downtown Winter Park, top-rated public schools, and with easy access to major roadways, this home offers the best of comfort and convenience. Don’t miss your chance to own this move-in-ready home in one of Maitland’s desirable locations. 3 Beds ⋅ 2 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code Renovated Maitland Gem with newer pool, move-In ready! Tucked away in a peaceful Maitland neighborhood, this beautifully updated one-story home offers a blend of style, comfort and convenience. With three bedrooms, two baths and 1,760 square feet of thoughtfully designed living space, this property is a hidden gem. Enjoy unbeatable curb appeal with lush landscaping, newer windows/doors, a lighted walkway to the front door, and a welcoming open front deck with a stylish, modern privacy wall. The oversized brick paver driveway adds charm and functionality. Inside, tile flooring flows seamlessly throughout the entire home, enhancing its clean, cohesive look. Plantation shutters and designer lighting add a refined touch to every room, while custom closet systems maximize storage in all bedrooms. The open-concept kitchen is a dream for everyday living and entertaining, featuring soft-close cabinets and drawers, bar seating and a cozy breakfast nook. It overlooks the spacious great room and dining area, both adorned with large picture windows that frame serene views of the backyard and pool. The primary suite offers a relaxing retreat with a walk-in closet and a beautifully updated en-suite bath with a large glass-enclosed shower. Two additional bedrooms and a spacious laundry room complete the smartly designed layout. Go outside to your private backyard oasis, fully fenced for privacy and beautifully landscaped to create a picturesque setting. A sparkling, heated/saltwater pool invites you to unwind or entertain, while the generous green space provides ample room for outdoor games, gardening, pets or future enhancements. The covered patio is ideal for alfresco dining, morning coffee or simply enjoying the Florida sunshine in your tranquil retreat. Additional features include a one-car garage with a large storage room and additional refrigerator. Just minutes from downtown Winter Park, top-rated public schools, and with easy access to major roadways, this home offers the best of comfort and convenience. Don’t miss your chance to own this move-in-ready home in one of Maitland’s desirable locations. 113 Tangelo Court, Maitland
$700,000 Welcome to this beautifully updated Maitland home in the coveted Dommerich Estates neighborhood. This home is the best value in Maitland with an assumable 2.75 Percent interest rate available! The spacious 4 Bedroom, 3 Bathroom layout features a hard-to-find split floor plan plus an abundance of storage and space that is rare in mid-century homes. The oversized half-acre homesite provides ample room to safely store your boat and RV or even explore the possibilities of adding a guest house / accessory dwelling unit (ADU) by the sparkling pool. Step inside the front of this home to discover a light-filled living room with stunning picture windows that flood the space in natural sunlight. The bright and airy feel continues as views of the backyard oasis are visible from both the living and dining rooms. A large Florida Room along the back of the home offers additional living space, ideal as a home office or just a relaxing retreat. Updates in the kitchen include granite countertops and stainless steel appliances, making it a chef’s dream. Just off the kitchen is a spacious indoor laundry room, complete with a butler's pantry and extra storage. Fresh paint and new flooring make the bedrooms truly move-in ready! Located in the heart of Maitland, you’re just minutes away from Maitland Community Park, Maitland City Centre, and the celebrated shopping, dining, and cultural attractions of Winter Park. Utilities are reliable with underground electrical lines completed by Duke and city sewer service already in place. Through the voluntary HOA, residents have access to the Winter Park Chain of Lakes from the community park and boat ramp on Lake Minnehaha. Zoned schools include Winter Park High as well as Dommerich Elementary and Maitland Middle, both of which are minutes from the home via walking sidewalks or bike lanes. This amazing home is eligible for an assumable mortgage with a 2.75 interest rate for qualified buyers! Don’t miss the opportunity to make this extraordinary Dommerich property yours! 4 Beds ⋅ 3 Baths ⋅ Dommerich Estates SubDv. ⋅ 32751 Zip Code Welcome to this beautifully updated Maitland home in the coveted Dommerich Estates neighborhood. This home is the best value in Maitland with an assumable 2.75 Percent interest rate available! The spacious 4 Bedroom, 3 Bathroom layout features a hard-to-find split floor plan plus an abundance of storage and space that is rare in mid-century homes. The oversized half-acre homesite provides ample room to safely store your boat and RV or even explore the possibilities of adding a guest house / accessory dwelling unit (ADU) by the sparkling pool. Step inside the front of this home to discover a light-filled living room with stunning picture windows that flood the space in natural sunlight. The bright and airy feel continues as views of the backyard oasis are visible from both the living and dining rooms. A large Florida Room along the back of the home offers additional living space, ideal as a home office or just a relaxing retreat. Updates in the kitchen include granite countertops and stainless steel appliances, making it a chef’s dream. Just off the kitchen is a spacious indoor laundry room, complete with a butler's pantry and extra storage. Fresh paint and new flooring make the bedrooms truly move-in ready! Located in the heart of Maitland, you’re just minutes away from Maitland Community Park, Maitland City Centre, and the celebrated shopping, dining, and cultural attractions of Winter Park. Utilities are reliable with underground electrical lines completed by Duke and city sewer service already in place. Through the voluntary HOA, residents have access to the Winter Park Chain of Lakes from the community park and boat ramp on Lake Minnehaha. Zoned schools include Winter Park High as well as Dommerich Elementary and Maitland Middle, both of which are minutes from the home via walking sidewalks or bike lanes. This amazing home is eligible for an assumable mortgage with a 2.75 interest rate for qualified buyers! Don’t miss the opportunity to make this extraordinary Dommerich property yours! 1641 E Horatio Avenue, Maitland
$979,000 Welcome to this stunning move-in ready pool home in the highly sought after Dommerich neighborhood, known for its top-rated schools and wonderful community. Nestled on an over-sized corner lot in a quiet cul-de-sac, this beautifully maintained home boasts 4 bedrooms, 2 full bathrooms, plus a convenient half bath. The lush landscaping professionally designed by a certified Landscape Designer, exudes gorgeous curb appeal and surrounds the backyard pool and heated spa, creating a private oasis. A separate screened-in porch is connected by pavers providing another quiet retreat. Step inside to find a light-filled interior with elegant finishes and plenty of room to entertain. The heart of the home is the expansive chef's kitchen with modern appliances featuring a double oven, 2 gorgeous islands with plenty of barstool seating, room for a full dining table, plus an abundance of storage and pantry space. There are 2 large separate living rooms with gorgeous wood flooring and a full bedroom on the first floor, which also makes a perfect office. Upstairs is the huge Primary bedroom and walk-in closet with its completely renovated (2023) en-suite bathroom with quartz countertops, a lovely step-in shower and another closet for additional storage. There are 2 more beautiful bedrooms with good sized closets, another full bright bathroom with double sinks, and a huge laundry room. This worry free home makes getting insurance a breeze with a brand new A/C (2024) complete new roof installation, Hardie Board siding, and an in-ground pool and spa (all in 2015), plus a full home security system with pool security alarms on all of the downstairs doors. This perfectly located home allows for walking to Maitland Community Park, riding bikes to the A-rated public schools, and driving minutes to downtown Maitland with its restaurants, shops and grocery stores. Don't miss your chance to live in this fabulous home and join this welcoming community. Schedule your private showing today! 4 Beds ⋅ 3 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code Welcome to this stunning move-in ready pool home in the highly sought after Dommerich neighborhood, known for its top-rated schools and wonderful community. Nestled on an over-sized corner lot in a quiet cul-de-sac, this beautifully maintained home boasts 4 bedrooms, 2 full bathrooms, plus a convenient half bath. The lush landscaping professionally designed by a certified Landscape Designer, exudes gorgeous curb appeal and surrounds the backyard pool and heated spa, creating a private oasis. A separate screened-in porch is connected by pavers providing another quiet retreat. Step inside to find a light-filled interior with elegant finishes and plenty of room to entertain. The heart of the home is the expansive chef's kitchen with modern appliances featuring a double oven, 2 gorgeous islands with plenty of barstool seating, room for a full dining table, plus an abundance of storage and pantry space. There are 2 large separate living rooms with gorgeous wood flooring and a full bedroom on the first floor, which also makes a perfect office. Upstairs is the huge Primary bedroom and walk-in closet with its completely renovated (2023) en-suite bathroom with quartz countertops, a lovely step-in shower and another closet for additional storage. There are 2 more beautiful bedrooms with good sized closets, another full bright bathroom with double sinks, and a huge laundry room. This worry free home makes getting insurance a breeze with a brand new A/C (2024) complete new roof installation, Hardie Board siding, and an in-ground pool and spa (all in 2015), plus a full home security system with pool security alarms on all of the downstairs doors. This perfectly located home allows for walking to Maitland Community Park, riding bikes to the A-rated public schools, and driving minutes to downtown Maitland with its restaurants, shops and grocery stores. Don't miss your chance to live in this fabulous home and join this welcoming community. Schedule your private showing today! 1621 Chippewa Trail, Maitland
$1,200,000 One or more photo(s) has been virtually staged. This meticulously maintained home in the desirable Stonehill community offers an exceptional layout with thoughtful upgrades throughout. The freshly painted exterior and recently replaced tile roof give it standout curb appeal. Inside, the grand foyer, with soaring ceilings, leads into a formal living room with French doors overlooking the sparkling screened-in pool and covered patio. To the left, the formal dining room showcases elegant coffered ceilings, while the adjacent kitchen is a chef’s dream—featuring custom-built cabinetry, stunning granite countertops, a Viking double oven, built-in Sub-Zero refrigerator with a cabinet-matching front, Miele built-in coffee maker, built-in microwave, cooktop with a pot filler, and even two additional refrigerator drawers for extra storage. The kitchen opens to a spacious dinette and family room with a wood-burning fireplace and additional French doors leading outside. On the main floor, the primary suite offers high ceilings, French doors opening to the back patio, and a spa-like bath with dual walk-in closets, two vanities, a large walk-in shower with dual showerheads, and ample storage. A versatile additional room on this level, complete with a closet, is located across from a fully renovated pool bath, making it perfect for a home office or guest space. The large laundry room, featuring built-in cabinets and a sink, sits just off the kitchen near the entrance to the two-car garage. Upstairs, a spacious bonus room with a huge storage closet provides extra living space. Two generously sized bedrooms share a Jack-and-Jill bathroom with double vanities and a tub/shower combo, while another well-sized bedroom and an additional full bath complete the upper level. Beautiful wood floors run throughout the home, complemented by high baseboards and crown molding for a polished look. Outside, the screened-in patio and sparkling pool with a water feature offer a private retreat, while the fenced backyard adds both security and privacy. Located between Maitland Ave and 17-92, this home provides easy access to top dining, shopping, and entertainment in Maitland and Winter Park. Major roads including I-4, 17-92, and SR 436 are just minutes away, and the nearby SunRail station makes commuting downtown a breeze. Call today for a private showing! 4 Beds ⋅ 4 Baths ⋅ Stonehill SubDv. ⋅ 32751 Zip Code One or more photo(s) has been virtually staged. This meticulously maintained home in the desirable Stonehill community offers an exceptional layout with thoughtful upgrades throughout. The freshly painted exterior and recently replaced tile roof give it standout curb appeal. Inside, the grand foyer, with soaring ceilings, leads into a formal living room with French doors overlooking the sparkling screened-in pool and covered patio. To the left, the formal dining room showcases elegant coffered ceilings, while the adjacent kitchen is a chef’s dream—featuring custom-built cabinetry, stunning granite countertops, a Viking double oven, built-in Sub-Zero refrigerator with a cabinet-matching front, Miele built-in coffee maker, built-in microwave, cooktop with a pot filler, and even two additional refrigerator drawers for extra storage. The kitchen opens to a spacious dinette and family room with a wood-burning fireplace and additional French doors leading outside. On the main floor, the primary suite offers high ceilings, French doors opening to the back patio, and a spa-like bath with dual walk-in closets, two vanities, a large walk-in shower with dual showerheads, and ample storage. A versatile additional room on this level, complete with a closet, is located across from a fully renovated pool bath, making it perfect for a home office or guest space. The large laundry room, featuring built-in cabinets and a sink, sits just off the kitchen near the entrance to the two-car garage. Upstairs, a spacious bonus room with a huge storage closet provides extra living space. Two generously sized bedrooms share a Jack-and-Jill bathroom with double vanities and a tub/shower combo, while another well-sized bedroom and an additional full bath complete the upper level. Beautiful wood floors run throughout the home, complemented by high baseboards and crown molding for a polished look. Outside, the screened-in patio and sparkling pool with a water feature offer a private retreat, while the fenced backyard adds both security and privacy. Located between Maitland Ave and 17-92, this home provides easy access to top dining, shopping, and entertainment in Maitland and Winter Park. Major roads including I-4, 17-92, and SR 436 are just minutes away, and the nearby SunRail station makes commuting downtown a breeze. Call today for a private showing! 142 Stone Hill Drive, Maitland