Homesinorlando.forsale Search Results

$1,165,000

Built in 2014 and set within the highly sought-after Dommerich Estates neighborhood of Maitland, this thoughtfully maintained two-story home offers a rare blend of space, function, and location. With five bedrooms, three full bathrooms, and a flexible bonus room, the layout is designed to adapt easily to modern living. The entry opens to a formal dining space, while an additional room just off the foyer provides an ideal spot for a home office, den, or reading lounge. Dark hardwood floors anchor the main living areas and create a warm, cohesive feel throughout. At the heart of the home, the open kitchen and family room flow seamlessly together and look out over the backyard—perfect for both relaxed evenings and hosting gatherings. The kitchen features Bosch stainless steel appliances, granite countertops, a generous island with seating, and custom maple cabinetry, offering both style and practicality. The primary suite is privately positioned on the main level and includes two walk-in closets. Its en-suite bath is finished with double vanities, a soaking tub, a separate shower, and ceramic tile throughout. Two additional bedrooms on the first floor share a full bathroom with ceramic tile and a granite-topped vanity. Upstairs, a spacious bonus room creates endless possibilities, accompanied by two more bedrooms connected by a Jack-and-Jill bathroom with matching granite and tile finishes. Notable extras include an interior laundry room with washer and dryer, dual HVAC systems, and a fully fenced backyard with a lovely patio and plenty of room to add a pool or play area. Ideally located just moments from the new boardwalk leading to Maitland Community Park, residents enjoy easy access to walking paths, green space, playgrounds, and nearby tennis courts, enhancing the neighborhood’s active and outdoor lifestyle. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School, the home also grants access to Lake Minnehaha, where residents enjoy a private boat ramp and fishing dock. A standout opportunity in one of Maitland’s most established and beloved lakefront communities. This home is back on the market after the previous buyer experienced a personal change in plans. No issues with the property.

5 Beds ⋅ 3 Baths ⋅ Dommerich Estates 1st Add SubDv. ⋅ 32751 Zip Code

Built in 2014 and set within the highly sought-after Dommerich Estates neighborhood of Maitland, this thoughtfully maintained two-story home offers a rare blend of space, function, and location. With five bedrooms, three full bathrooms, and a flexible bonus room, the layout is designed to adapt easily to modern living. The entry opens to a formal dining space, while an additional room just off the foyer provides an ideal spot for a home office, den, or reading lounge. Dark hardwood floors anchor the main living areas and create a warm, cohesive feel throughout. At the heart of the home, the open kitchen and family room flow seamlessly together and look out over the backyard—perfect for both relaxed evenings and hosting gatherings. The kitchen features Bosch stainless steel appliances, granite countertops, a generous island with seating, and custom maple cabinetry, offering both style and practicality. The primary suite is privately positioned on the main level and includes two walk-in closets. Its en-suite bath is finished with double vanities, a soaking tub, a separate shower, and ceramic tile throughout. Two additional bedrooms on the first floor share a full bathroom with ceramic tile and a granite-topped vanity. Upstairs, a spacious bonus room creates endless possibilities, accompanied by two more bedrooms connected by a Jack-and-Jill bathroom with matching granite and tile finishes. Notable extras include an interior laundry room with washer and dryer, dual HVAC systems, and a fully fenced backyard with a lovely patio and plenty of room to add a pool or play area. Ideally located just moments from the new boardwalk leading to Maitland Community Park, residents enjoy easy access to walking paths, green space, playgrounds, and nearby tennis courts, enhancing the neighborhood’s active and outdoor lifestyle. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High School, the home also grants access to Lake Minnehaha, where residents enjoy a private boat ramp and fishing dock. A standout opportunity in one of Maitland’s most established and beloved lakefront communities. This home is back on the market after the previous buyer experienced a personal change in plans. No issues with the property.

1750 Cheyenne Trail, Maitland

$1,798,999

Under contract-accepting backup offers. Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positioned in the prestigious neighborhood of Hollieanna Shores. As you arrive, a striking façade with an elegant arched entryway sets an unforgettable tone. Beyond the front door, soaring ceilings and designer finishes frame an expansive living room where glass sliders dissolve the boundary between indoor and outdoor living, creating a seamless transition to the lanai and resort-style backyard. At the heart of the home, a chef’s kitchen designed for both performance and beauty exceeds every expectation. Sleek quartz countertops, a full Thermador appliance suite, custom cabinetry, and an oversized walk-in pantry elevate culinary experiences to a professional standard. The primary suite is a private sanctuary intentionally crafted to evoke a spa-like retreat. A stunning bathroom showcases a freestanding tub, an expansive walk-in shower, dual vanities, and exquisite finishes, while a large boutique-style closet with custom built-ins ensures every piece has its place. The upstairs level offers a generous loft and beautifully appointed secondary bedrooms, creating the ideal separation of space for family or guests. Outdoor living is nothing short of extraordinary, featuring a huge covered lanai with a full summer kitchen overlooking a shimmering pool and expansive, fully fenced backyard. Situated in the sought-after Hollieanna Shores neighborhood, this residence places you moments from Maitland City Centre, local parks, the iconic Enzian Theatre, and Park Ave. shopping and dining. If you’re seeking a home that feels both artful and effortless, this is where elevated living becomes reality.

5 Beds ⋅ 5 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positioned in the prestigious neighborhood of Hollieanna Shores. As you arrive, a striking façade with an elegant arched entryway sets an unforgettable tone. Beyond the front door, soaring ceilings and designer finishes frame an expansive living room where glass sliders dissolve the boundary between indoor and outdoor living, creating a seamless transition to the lanai and resort-style backyard. At the heart of the home, a chef’s kitchen designed for both performance and beauty exceeds every expectation. Sleek quartz countertops, a full Thermador appliance suite, custom cabinetry, and an oversized walk-in pantry elevate culinary experiences to a professional standard. The primary suite is a private sanctuary intentionally crafted to evoke a spa-like retreat. A stunning bathroom showcases a freestanding tub, an expansive walk-in shower, dual vanities, and exquisite finishes, while a large boutique-style closet with custom built-ins ensures every piece has its place. The upstairs level offers a generous loft and beautifully appointed secondary bedrooms, creating the ideal separation of space for family or guests. Outdoor living is nothing short of extraordinary, featuring a huge covered lanai with a full summer kitchen overlooking a shimmering pool and expansive, fully fenced backyard. Situated in the sought-after Hollieanna Shores neighborhood, this residence places you moments from Maitland City Centre, local parks, the iconic Enzian Theatre, and Park Ave. shopping and dining. If you’re seeking a home that feels both artful and effortless, this is where elevated living becomes reality.

105 Tangelo Court, 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

$1,425,000

Sophisticated and timeless, this stunning one-story home was completely reimagined in 2019 by multi-award-winning builder and design through Z-Properties. Taken down to the studs and rebuilt with the finest materials, this split-plan three-bedroom, three-bath residence blends modern design with an inviting, incredible design feel. Gorgeous high grade wood flooring throughout along with expansive windows and walls of glass flood the interiors with natural light, taking advantage of picturesque views! The backyard is a sanctuary setting with Signature Landscape mature landscaping and sparkling pool and separate spa. The open concept design is ideal for daily living and entertaining, with a seamless flow extremely well thought-out living areas. A designer-inspired gas fireplace in the dining area creates a sophisticated and welcoming ambiance, while two sets of glass doors in the living room open to the inviting outdoor living spaces. The stately kitchen is a showpiece, featuring Thermador Pro Series appliances, a Sub-Zero wine tower, and elegant counters that elevate form and function. The primary suite offers a private retreat with a generous walk-in closet and a spa like well-appointed bath. Two additional bedroom suites are equally refined, each with custom closets for optimal storage and organization. Outside, every detail has been thoughtfully curated. The private front courtyard, centered around a tranquil Zen fountain private courtyard, sets the tone for the home's refined elegance. The rear outdoor living area features Brazilian IPE wood decking surrounding the heated saltwater pool, alongside lush landscaping, complete with sculpted hedges and tropical palms, creates a resort-like ambiance. A built-in summer kitchen includes a gas grill and green egg off the kitchen, and flex space is framed by a beautiful bougainvillea hedge for added serenity, ideal for effortless outdoor entertaining. Lastly there is a fully finished garage with indoor/outdoor carpeting and is temperature controlled with its mini-split AC unit. Residents of Hollieanna Shores enjoy deeded lake access to Lake Maitland, part of the prestigious Winter Park Chain-of-Lakes, via a private community boat ramp. Ideally with convenient access to major roadways, this exceptional home offers easy commutes to downtown Winter Park, Orlando and area airports, a sophisticated retreat in one of Central Florida's desirable Maitland/Winter Park hidden gem neighborhoods!

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

Sophisticated and timeless, this stunning one-story home was completely reimagined in 2019 by multi-award-winning builder and design through Z-Properties. Taken down to the studs and rebuilt with the finest materials, this split-plan three-bedroom, three-bath residence blends modern design with an inviting, incredible design feel. Gorgeous high grade wood flooring throughout along with expansive windows and walls of glass flood the interiors with natural light, taking advantage of picturesque views! The backyard is a sanctuary setting with Signature Landscape mature landscaping and sparkling pool and separate spa. The open concept design is ideal for daily living and entertaining, with a seamless flow extremely well thought-out living areas. A designer-inspired gas fireplace in the dining area creates a sophisticated and welcoming ambiance, while two sets of glass doors in the living room open to the inviting outdoor living spaces. The stately kitchen is a showpiece, featuring Thermador Pro Series appliances, a Sub-Zero wine tower, and elegant counters that elevate form and function. The primary suite offers a private retreat with a generous walk-in closet and a spa like well-appointed bath. Two additional bedroom suites are equally refined, each with custom closets for optimal storage and organization. Outside, every detail has been thoughtfully curated. The private front courtyard, centered around a tranquil Zen fountain private courtyard, sets the tone for the home's refined elegance. The rear outdoor living area features Brazilian IPE wood decking surrounding the heated saltwater pool, alongside lush landscaping, complete with sculpted hedges and tropical palms, creates a resort-like ambiance. A built-in summer kitchen includes a gas grill and green egg off the kitchen, and flex space is framed by a beautiful bougainvillea hedge for added serenity, ideal for effortless outdoor entertaining. Lastly there is a fully finished garage with indoor/outdoor carpeting and is temperature controlled with its mini-split AC unit. Residents of Hollieanna Shores enjoy deeded lake access to Lake Maitland, part of the prestigious Winter Park Chain-of-Lakes, via a private community boat ramp. Ideally with convenient access to major roadways, this exceptional home offers easy commutes to downtown Winter Park, Orlando and area airports, a sophisticated retreat in one of Central Florida's desirable Maitland/Winter Park hidden gem neighborhoods!

123 Hollie Court, Maitland

$2,550,000

Wonderful lakefront lot opportunity to create a custom legacy estate on Lake Maitland, part of the Maitland-Winter Park Chain of Lakes. Lakefront homesites are becoming increasingly rare, and this offering is truly special. Tucked away on a quiet street, the property enjoys a very private setting with the ability to be gated, along with sweeping southern lake views that capture both sunrise and sunset in equal measure. Photos #9–#14 illustrate a thoughtfully conceived design concept created specifically to complement the lot’s dimensions and orientation, while maximizing panoramic lake views and indoor-outdoor living. With approximately 18,500 square feet of upland to be developed, there is potential to build a residence of approximately 7,500 square feet (roughly 40% of the lot size). The site has already been cleared and is ready for construction, allowing a future owner to move seamlessly from vision to reality. Property enhancements include a seawall, gated front entry drive, and a covered boat lift with dock—offering immediate access to boating, fishing, and water sports. This is a rare canvas for a multi-generational lakefront estate, where architectural distinction meets a lifestyle centered on the water. Days may be spent wakeboarding, casting a fishing line, or relaxing poolside as boats glide across the lake, while evenings invite effortless cruises across the water to the Winter Park Racquet Club for dinner, cocktails, and social gatherings. Nestled in a secluded enclave of Maitland, the property is just minutes from the boutiques and dining of Park Avenue, with convenient access to downtown Maitland, major roadways, and the greater Orlando area. Note: The adjacent lakefront property, 127 Whitecaps Circle (24,472 square feet, approximately 0.56 acres) is also listed for sale, presenting a rare opportunity to combine two neighboring lakefront parcels and create a private compound for family or friends. All building calculations and development potential to be confirmed with the City of Maitland and the buyer’s builder and architect during due diligence, as any referenced figures are preliminary and not officially verified.

Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code

Wonderful lakefront lot opportunity to create a custom legacy estate on Lake Maitland, part of the Maitland-Winter Park Chain of Lakes. Lakefront homesites are becoming increasingly rare, and this offering is truly special. Tucked away on a quiet street, the property enjoys a very private setting with the ability to be gated, along with sweeping southern lake views that capture both sunrise and sunset in equal measure. Photos #9–#14 illustrate a thoughtfully conceived design concept created specifically to complement the lot’s dimensions and orientation, while maximizing panoramic lake views and indoor-outdoor living. With approximately 18,500 square feet of upland to be developed, there is potential to build a residence of approximately 7,500 square feet (roughly 40% of the lot size). The site has already been cleared and is ready for construction, allowing a future owner to move seamlessly from vision to reality. Property enhancements include a seawall, gated front entry drive, and a covered boat lift with dock—offering immediate access to boating, fishing, and water sports. This is a rare canvas for a multi-generational lakefront estate, where architectural distinction meets a lifestyle centered on the water. Days may be spent wakeboarding, casting a fishing line, or relaxing poolside as boats glide across the lake, while evenings invite effortless cruises across the water to the Winter Park Racquet Club for dinner, cocktails, and social gatherings. Nestled in a secluded enclave of Maitland, the property is just minutes from the boutiques and dining of Park Avenue, with convenient access to downtown Maitland, major roadways, and the greater Orlando area. Note: The adjacent lakefront property, 127 Whitecaps Circle (24,472 square feet, approximately 0.56 acres) is also listed for sale, presenting a rare opportunity to combine two neighboring lakefront parcels and create a private compound for family or friends. All building calculations and development potential to be confirmed with the City of Maitland and the buyer’s builder and architect during due diligence, as any referenced figures are preliminary and not officially verified.

125 Whitecaps Circle, Maitland

$995,000

BACK ON THE MARKET!! Welcome to 1630 Chinook Trail, a fully renovated custom patio-style home making its market debut. Designed by builder Phil Kerr and architect Alan Berman, this home features French doors from nearly every room opening to a sparkling pool. Inside you’ll find 3 bedrooms plus a den, guest suite with walk-in closet and ensuite bath, and a 4th bedroom converted into a spacious master closet that can easily be re-converted. The open floor plan boasts a chef’s kitchen with a 10-ft island, 2 dishwashers, double-wide fridge, double ovens with convection, pot filler, and gas range. Additional highlights include a gas fireplace, Nuvo sound system, tankless water heater, energy-efficient windows, and a 2-car garage with workshop space. Outdoors enjoy a travertine front patio, fenced backyard with deck and tree fort, and a resort-style pool with travertine decking and water feature. This home has deeded lake access and a private boat ramp into Lake Minnehaha and walking distance to top-rated schools and Maitland Community Park.

3 Beds ⋅ 3 Baths ⋅ Dommerich Woods SubDv. ⋅ 32751 Zip Code

BACK ON THE MARKET!! Welcome to 1630 Chinook Trail, a fully renovated custom patio-style home making its market debut. Designed by builder Phil Kerr and architect Alan Berman, this home features French doors from nearly every room opening to a sparkling pool. Inside you’ll find 3 bedrooms plus a den, guest suite with walk-in closet and ensuite bath, and a 4th bedroom converted into a spacious master closet that can easily be re-converted. The open floor plan boasts a chef’s kitchen with a 10-ft island, 2 dishwashers, double-wide fridge, double ovens with convection, pot filler, and gas range. Additional highlights include a gas fireplace, Nuvo sound system, tankless water heater, energy-efficient windows, and a 2-car garage with workshop space. Outdoors enjoy a travertine front patio, fenced backyard with deck and tree fort, and a resort-style pool with travertine decking and water feature. This home has deeded lake access and a private boat ramp into Lake Minnehaha and walking distance to top-rated schools and Maitland Community Park.

1630 Chinook Trail, Maitland

$1,655,000

Showpiece Charles Clayton Home in Gated Lake Colony Estates Every detail of this 5-bedroom, 4.5-bath plus office residence was designed to impress, including a full in-law apartment and an outdoor living space that feels like a private resort. Set on a prime corner lot, this home combines timeless craftsmanship with modern finishes: tile roof, travertine downstairs, hardwood upstairs, sleek wrought iron staircase, coffered ceilings, plantation shutters, and designer lighting. The chef’s kitchen is built for both cooking and entertaining—gas stove, double ovens, custom cabinetry, granite counters, oversized breakfast bar, and sunny dining nook. A two-sided stone fireplace connects the office and family room, adding warmth and character. The primary suite is a retreat of its own: spa-style shower with six body sprayers and dual rain heads, a private tankless water heater, and a two-story custom closet built for a true collection. Guests enjoy privacy with a separate stairway leading to a full in-law apartment complete with family room. Step outside to the ultimate backyard: screened, gas-heated pool, tongue-and-groove ceiling patio, outdoor kitchen with grill, sink, granite workspace, storage, TV, and built-in keg fridge. Additional highlights: spotless 3-car epoxy garage with workshop, built-in office cabinetry, 12-foot ceilings, beadboard accents, and a dog run. And the best part? All of this is in close proximity to Orangewood Christian School and just minutes from Winter Park, top-rated dining, and shopping. A rare opportunity to own a true Maitland showpiece.

5 Beds ⋅ 5 Baths ⋅ Lake Colony Ph 01 Rep SubDv. ⋅ 32751 Zip Code

Showpiece Charles Clayton Home in Gated Lake Colony Estates Every detail of this 5-bedroom, 4.5-bath plus office residence was designed to impress, including a full in-law apartment and an outdoor living space that feels like a private resort. Set on a prime corner lot, this home combines timeless craftsmanship with modern finishes: tile roof, travertine downstairs, hardwood upstairs, sleek wrought iron staircase, coffered ceilings, plantation shutters, and designer lighting. The chef’s kitchen is built for both cooking and entertaining—gas stove, double ovens, custom cabinetry, granite counters, oversized breakfast bar, and sunny dining nook. A two-sided stone fireplace connects the office and family room, adding warmth and character. The primary suite is a retreat of its own: spa-style shower with six body sprayers and dual rain heads, a private tankless water heater, and a two-story custom closet built for a true collection. Guests enjoy privacy with a separate stairway leading to a full in-law apartment complete with family room. Step outside to the ultimate backyard: screened, gas-heated pool, tongue-and-groove ceiling patio, outdoor kitchen with grill, sink, granite workspace, storage, TV, and built-in keg fridge. Additional highlights: spotless 3-car epoxy garage with workshop, built-in office cabinetry, 12-foot ceilings, beadboard accents, and a dog run. And the best part? All of this is in close proximity to Orangewood Christian School and just minutes from Winter Park, top-rated dining, and shopping. A rare opportunity to own a true Maitland showpiece.

104 E Lake Colony Drive, 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

$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

$2,770,000

Exquisite Lakeview pool home, built in 2021, combines modern elegance and timeless style. Located in the heart of Maitland, with front-row seats to unforgettable sunsets over Lake Sybelia! This Five bedroom, Five and a half bath residence boasts 4,697 square feet of tastefully designed living space. Inside you’re met by a grand foyer and airy layout flooded with natural light, soaring ceilings, wide-plank hardwood floors, custom window treatments, and designer finishes throughout. The gourmet kitchen is an entertainer's delight-equipped with top-of-the-line Wolf and Sub-zero appliances, Taj Mahal quartzite, stunning 12-foot waterfall island, 48” 8 burner gas range with pot filler, large walk-in pantry, with butler’s pantry adjoining the kitchen and dining— the open concept design is perfect for both entertaining and every day living. The living room’s quartz-accented fireplace and sleek glass folding doors provide a seamless flow between indoor and outdoor living. Retreat to the primary suite's spa-inspired bathroom with custom designed walk-in closet, dual vanities, soaking tub and double walk-through shower. A sleek cable railing staircase leads to four generously sized Bedrooms-three with ensuite baths, four bathrooms, a designated Office and versatile Loft/Flex space. Enjoy breathtaking lake views whether working or unwinding! Equally impressive is the beautifully landscaped outdoor living space, with expansive covered lanai, multiple lounge areas, fully equipped summer kitchen, gas fire pit and luxurious salt-water pool and spa. Property features smart home technology, custom closets systems, remote controlled window treatments, surround sound, full-house generator, 500 lb propane tank, 3 car garage with epoxy flooring and so much more! A short walk to Lake Lily and the Maitland Farmers Market, and minutes to Winter Park and I-4. This exceptional home combines refined luxury with an unbeatable location. Don’t miss out on this rare find!

5 Beds ⋅ 6 Baths ⋅ Poors Add SubDv. ⋅ 32751 Zip Code

Exquisite Lakeview pool home, built in 2021, combines modern elegance and timeless style. Located in the heart of Maitland, with front-row seats to unforgettable sunsets over Lake Sybelia! This Five bedroom, Five and a half bath residence boasts 4,697 square feet of tastefully designed living space. Inside you’re met by a grand foyer and airy layout flooded with natural light, soaring ceilings, wide-plank hardwood floors, custom window treatments, and designer finishes throughout. The gourmet kitchen is an entertainer's delight-equipped with top-of-the-line Wolf and Sub-zero appliances, Taj Mahal quartzite, stunning 12-foot waterfall island, 48” 8 burner gas range with pot filler, large walk-in pantry, with butler’s pantry adjoining the kitchen and dining— the open concept design is perfect for both entertaining and every day living. The living room’s quartz-accented fireplace and sleek glass folding doors provide a seamless flow between indoor and outdoor living. Retreat to the primary suite's spa-inspired bathroom with custom designed walk-in closet, dual vanities, soaking tub and double walk-through shower. A sleek cable railing staircase leads to four generously sized Bedrooms-three with ensuite baths, four bathrooms, a designated Office and versatile Loft/Flex space. Enjoy breathtaking lake views whether working or unwinding! Equally impressive is the beautifully landscaped outdoor living space, with expansive covered lanai, multiple lounge areas, fully equipped summer kitchen, gas fire pit and luxurious salt-water pool and spa. Property features smart home technology, custom closets systems, remote controlled window treatments, surround sound, full-house generator, 500 lb propane tank, 3 car garage with epoxy flooring and so much more! A short walk to Lake Lily and the Maitland Farmers Market, and minutes to Winter Park and I-4. This exceptional home combines refined luxury with an unbeatable location. Don’t miss out on this rare find!

216 N Lake Sybelia Drive, Maitland

$1,153,000

Welcome to this custom-built 4 bedroom, 3 bathroom home located in the gated community of Lake Colony Estates. This beautifully remodeled property includes an enclosed private mother-in-law suite or office, perfect for extended family, guests, or remote work. Enjoy a breathtaking courtyard view from the expansive formal living area, featuring an open and airy layout surrounded by manicured landscaping for total privacy and tranquility. This meticulously maintained home includes numerous recent upgrades which include a newer tile roof (2019), two replaced AC units, two replaced water heaters, newer double pane windows, triple-stranded bamboo flooring, newer screened in pool enclosure, brand-new above ground spa, a private putting course and more. The gourmet kitchen is outfitted with updated GE Monogram appliances, a new Bosch dishwasher, and opens seamlessly to a brand-new outdoor kitchen and grilling area. A new Samsung washer and dryer are also included for added convenience. This home is being offered furnished aside from a few personal items and a couple items with sentimental value —just bring your suitcase and move right in. This home is rare find in one of the area’s most exclusive communities. Schedule your private showing today!

4 Beds ⋅ 3 Baths ⋅ Lake Colony Ph 01 Rep SubDv. ⋅ 32751 Zip Code

Welcome to this custom-built 4 bedroom, 3 bathroom home located in the gated community of Lake Colony Estates. This beautifully remodeled property includes an enclosed private mother-in-law suite or office, perfect for extended family, guests, or remote work. Enjoy a breathtaking courtyard view from the expansive formal living area, featuring an open and airy layout surrounded by manicured landscaping for total privacy and tranquility. This meticulously maintained home includes numerous recent upgrades which include a newer tile roof (2019), two replaced AC units, two replaced water heaters, newer double pane windows, triple-stranded bamboo flooring, newer screened in pool enclosure, brand-new above ground spa, a private putting course and more. The gourmet kitchen is outfitted with updated GE Monogram appliances, a new Bosch dishwasher, and opens seamlessly to a brand-new outdoor kitchen and grilling area. A new Samsung washer and dryer are also included for added convenience. This home is being offered furnished aside from a few personal items and a couple items with sentimental value —just bring your suitcase and move right in. This home is rare find in one of the area’s most exclusive communities. Schedule your private showing today!

1353 W Lake Colony Drive, Maitland

$1,920,000

Experience the ultimate in lake lifestyle living with this beautifully renovated four-bedroom, three-bath home located on the canal to Lake Maitland — one of the most desirable lakes on the Winter Park Chain-of-Lakes. Tucked away on a quiet cul-de-sac just one house from open water, this home offers the perfect blend of waterfront serenity and access to vibrant city amenities. Inside, the residence has been thoughtfully updated over the past six years, preserving its character while incorporating modern finishes. Refinished original hardwood floors flow through the main living areas, and the remodeled kitchen features quartz countertops, a glass backsplash, a Wolf gas cooktop, and opens to a bright, sunlit family room with three sets of French doors that lead to the pool, side deck, and expansive outdoor living areas. The spacious living room and a stylish media/den with a striking marble accent wall provide comfortable spaces to relax or entertain. The primary suite features French doors to the pool and a luxurious en-suite bath with a soaking tub, large glass shower, dual sinks, and a showstopping glass walk-in closet. Two additional bedrooms share a Jack-and-Jill bath, and a fourth bedroom with a full bath adds flexibility. Outdoor living takes center stage with a completely renovated pool featuring a HeatWave heating and cooling system and a sand-blasted marble deck. A generous covered lanai offers plenty of space to relax, grill, and entertain, and includes a 20x15-foot SunSetter motorized awning with LED lighting for shade and ambiance. Enjoy canal-front lounging on the WearDeck composite deck, or hop on your boat or Jet Ski from the covered boathouse with hoist lift and floating dock. Recent upgrades include a new Bosch A/C system (2024) with 10-year warranty and a new roof (2019) with transferrable warranty. Located minutes from Park Avenue in downtown Winter Park, this home also offers quick access to Maitland’s cultural corridor with its growing list of restaurants, Lake Lily Park, the Maitland Public Library, and the popular Lake Lily Farmers’ Market. This is a rare opportunity to enjoy the best of waterfront living in an unbeatable Central Florida location.

4 Beds ⋅ 3 Baths ⋅ Maitland Isle SubDv. ⋅ 32751 Zip Code

Experience the ultimate in lake lifestyle living with this beautifully renovated four-bedroom, three-bath home located on the canal to Lake Maitland — one of the most desirable lakes on the Winter Park Chain-of-Lakes. Tucked away on a quiet cul-de-sac just one house from open water, this home offers the perfect blend of waterfront serenity and access to vibrant city amenities. Inside, the residence has been thoughtfully updated over the past six years, preserving its character while incorporating modern finishes. Refinished original hardwood floors flow through the main living areas, and the remodeled kitchen features quartz countertops, a glass backsplash, a Wolf gas cooktop, and opens to a bright, sunlit family room with three sets of French doors that lead to the pool, side deck, and expansive outdoor living areas. The spacious living room and a stylish media/den with a striking marble accent wall provide comfortable spaces to relax or entertain. The primary suite features French doors to the pool and a luxurious en-suite bath with a soaking tub, large glass shower, dual sinks, and a showstopping glass walk-in closet. Two additional bedrooms share a Jack-and-Jill bath, and a fourth bedroom with a full bath adds flexibility. Outdoor living takes center stage with a completely renovated pool featuring a HeatWave heating and cooling system and a sand-blasted marble deck. A generous covered lanai offers plenty of space to relax, grill, and entertain, and includes a 20x15-foot SunSetter motorized awning with LED lighting for shade and ambiance. Enjoy canal-front lounging on the WearDeck composite deck, or hop on your boat or Jet Ski from the covered boathouse with hoist lift and floating dock. Recent upgrades include a new Bosch A/C system (2024) with 10-year warranty and a new roof (2019) with transferrable warranty. Located minutes from Park Avenue in downtown Winter Park, this home also offers quick access to Maitland’s cultural corridor with its growing list of restaurants, Lake Lily Park, the Maitland Public Library, and the popular Lake Lily Farmers’ Market. This is a rare opportunity to enjoy the best of waterfront living in an unbeatable Central Florida location.

210 Shell Point W, Maitland

$2,650,000

Stunning waterfront residence on Lake Minnehaha, part of the celebrated Winter Park Chain of Lakes! This spacious 5-bedroom, 4.5-bath home is designed for luxurious lakefront living and effortless entertaining. The gourmet kitchen is a chef’s dream, featuring a Thermador 6-burner gas range, GE Monogram side-by-side refrigerator and freezer, Bosch dishwasher, wine refrigerator, and a separate prep area with additional GE oven and dishwasher. The expansive first-floor primary suite offers lake views, a spa-style bath with custom cabinetry, an oversized shower, and a dedicated shoe closet. An additional first-floor bedroom with a private ensuite bath is ideal for guests or in-laws. Upstairs, you’ll find three additional bedrooms, two full baths, and a private office with serene views. Enjoy Florida living year-round with a resort-style outdoor space that includes a covered lanai, sparkling pool and spa, fire pit, and a covered boat dock. Bring your ski boat and jet skis — your backyard is a waterfront playground. Plantation shutters throughout add a classic touch to the interior. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High. Rare opportunity to live on the water in one of Central Florida’s most sought-after communities!

5 Beds ⋅ 5 Baths ⋅ Dommerich Estates 2nd Add SubDv. ⋅ 32751 Zip Code

Stunning waterfront residence on Lake Minnehaha, part of the celebrated Winter Park Chain of Lakes! This spacious 5-bedroom, 4.5-bath home is designed for luxurious lakefront living and effortless entertaining. The gourmet kitchen is a chef’s dream, featuring a Thermador 6-burner gas range, GE Monogram side-by-side refrigerator and freezer, Bosch dishwasher, wine refrigerator, and a separate prep area with additional GE oven and dishwasher. The expansive first-floor primary suite offers lake views, a spa-style bath with custom cabinetry, an oversized shower, and a dedicated shoe closet. An additional first-floor bedroom with a private ensuite bath is ideal for guests or in-laws. Upstairs, you’ll find three additional bedrooms, two full baths, and a private office with serene views. Enjoy Florida living year-round with a resort-style outdoor space that includes a covered lanai, sparkling pool and spa, fire pit, and a covered boat dock. Bring your ski boat and jet skis — your backyard is a waterfront playground. Plantation shutters throughout add a classic touch to the interior. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High. Rare opportunity to live on the water in one of Central Florida’s most sought-after communities!

591 Dommerich Drive, Maitland

$1,110,000

This Is It – The Dommerich Gem You've Been Waiting For! Nestled on a beautiful corner lot in one of Maitland's most desirable neighborhoods, this completely renovated 4-bedroom, 3.5-bath pool home is truly a showstopper! From the moment you enter the foyer, you’ll be captivated by gorgeous hardwood floors, plantation shutters throughout, and an abundance of natural light that fills every corner of the home. The open-concept layout is perfect for every day living, featuring custom built-ins and a welcoming family room that flows seamlessly into a cozy bench-style dining area. The heart of the home is the chef-inspired kitchen, boasting a large island with seating for six, gas range, farmhouse sink, ample storage with a built-in desk space. Adjacent to the kitchen is a flexible formal living space—ideal for a home office, playroom, or second entertainment area. Step outside to your private backyard oasis, complete with a covered porch with tongue-and-groove ceilings, sparkling pool, lush tropical landscaping, and your very own putting green! Inside, two secondary bedrooms share a full bath, while a third features a private ensuite that was added during the renovation. The primary suite is a retreat in itself, offering dual custom closets, French doors leading to the backyard, and a luxurious bathroom with a massive marble shower, freestanding soaking tub, and double vanities. As a bonus, a small, climate-controlled office space was added in the garage—perfect for working from home. Located in the heart of Dommerich, you’re just minutes from Park Avenue’s renowned shopping and dining, top-rated schools, and everything that makes this community so special. Don’t miss this rare opportunity to make this home yours!

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

This Is It – The Dommerich Gem You've Been Waiting For! Nestled on a beautiful corner lot in one of Maitland's most desirable neighborhoods, this completely renovated 4-bedroom, 3.5-bath pool home is truly a showstopper! From the moment you enter the foyer, you’ll be captivated by gorgeous hardwood floors, plantation shutters throughout, and an abundance of natural light that fills every corner of the home. The open-concept layout is perfect for every day living, featuring custom built-ins and a welcoming family room that flows seamlessly into a cozy bench-style dining area. The heart of the home is the chef-inspired kitchen, boasting a large island with seating for six, gas range, farmhouse sink, ample storage with a built-in desk space. Adjacent to the kitchen is a flexible formal living space—ideal for a home office, playroom, or second entertainment area. Step outside to your private backyard oasis, complete with a covered porch with tongue-and-groove ceilings, sparkling pool, lush tropical landscaping, and your very own putting green! Inside, two secondary bedrooms share a full bath, while a third features a private ensuite that was added during the renovation. The primary suite is a retreat in itself, offering dual custom closets, French doors leading to the backyard, and a luxurious bathroom with a massive marble shower, freestanding soaking tub, and double vanities. As a bonus, a small, climate-controlled office space was added in the garage—perfect for working from home. Located in the heart of Dommerich, you’re just minutes from Park Avenue’s renowned shopping and dining, top-rated schools, and everything that makes this community so special. Don’t miss this rare opportunity to make this home yours!

791 Arapaho Trail, Maitland

$1,399,900

Under Construction. Exquisite One-Story Pool Home with Summer Kitchen | Over 3,200 SF of Luxury Living in beautiful Maitland on an oversized lot! Impeccably designed and ideally located, this stunning single-story estate offers luxurious and refined living space with 4 bedrooms, 3 full baths, 2 half baths, and a private study. The open floor plan showcases rich wood flooring throughout, soaring ceilings, and quartz countertops for a seamless blend of comfort and sophistication. The gourmet kitchen boasts Bosch appliances and quartz counters and flows effortlessly into the spacious great room and dining area—perfect for entertaining. The luxurious owner’s suite features a spa-like bath and generous, dual walk-in closets. Step outside to a true Florida oasis: a resort-style pool and spa, covered lanai, and a fully equipped summer kitchen designed for indoor-outdoor living year-round. Additional highlights include: Designer-appointed finishes Oversized 2-car garage Prime location near top restaurants, shopping, and I-4 access This rare, one-level luxury residence offers timeless design and modern convenience in one of Central Florida’s most desirable locations. Close to endless dining and shopping options, come see this and make it yours today. rendering is an artist's conception and may be subject to change

4 Beds ⋅ 5 Baths ⋅ Beg 635 Ft E & 430 Ft N Of Sw Cor Of Sw1/4 Of Ne1/ SubDv. ⋅ 32751 Zip Code

Under Construction. Exquisite One-Story Pool Home with Summer Kitchen | Over 3,200 SF of Luxury Living in beautiful Maitland on an oversized lot! Impeccably designed and ideally located, this stunning single-story estate offers luxurious and refined living space with 4 bedrooms, 3 full baths, 2 half baths, and a private study. The open floor plan showcases rich wood flooring throughout, soaring ceilings, and quartz countertops for a seamless blend of comfort and sophistication. The gourmet kitchen boasts Bosch appliances and quartz counters and flows effortlessly into the spacious great room and dining area—perfect for entertaining. The luxurious owner’s suite features a spa-like bath and generous, dual walk-in closets. Step outside to a true Florida oasis: a resort-style pool and spa, covered lanai, and a fully equipped summer kitchen designed for indoor-outdoor living year-round. Additional highlights include: Designer-appointed finishes Oversized 2-car garage Prime location near top restaurants, shopping, and I-4 access This rare, one-level luxury residence offers timeless design and modern convenience in one of Central Florida’s most desirable locations. Close to endless dining and shopping options, come see this and make it yours today. rendering is an artist's conception and may be subject to change

850 Hillcrest Avenue, Maitland

$3,500,000

Prime mixed-use commercial property perfectly situated between the vibrant cities of Maitland and Winter Park. This centrally located asset offers both visibility and versatility. The listing encompasses a 29-unit multifamily building, adjacent commercial building 429 E. Kennedy Blvd, and a commercial lot 34 N. West St —offering incredible potential for future development, expansion, or mixed-use revitalization. Whether you’re an investor or developer, this is a rare opportunity to be part of a growing community with active revitalization efforts. New roof installed in 2023.

Coopers Sub SubDv. ⋅ 32751 Zip Code

Prime mixed-use commercial property perfectly situated between the vibrant cities of Maitland and Winter Park. This centrally located asset offers both visibility and versatility. The listing encompasses a 29-unit multifamily building, adjacent commercial building 429 E. Kennedy Blvd, and a commercial lot 34 N. West St —offering incredible potential for future development, expansion, or mixed-use revitalization. Whether you’re an investor or developer, this is a rare opportunity to be part of a growing community with active revitalization efforts. New roof installed in 2023.

421 E Kennedy Boulevard, Maitland

$1,350,000

The home you’ve been searching for has officially hit the market! Welcome to 2047 Howell Branch Road, the four bedroom, two bath home offering 2960 square feet of pure comfort. The beautiful exterior with its striking curb appeal will immediately draw you in before you even set foot inside. Entering through the foyer, you will feel a welcoming ambiance being flanked by a home office on one side and a multi purpose room on the other, flowing right into the wide open living spaces straight ahead. The family room features a brick fireplace, high cathedral ceilings and so much natural light seamlessly connecting to the kitchen, which has been updated to perfection. The large island has a beautiful stainless farmhouse sink and the cooktop encompassed inside the whitewashed brick nook will tempt even the most novice chef into whipping up an extravagant meal. The abundant natural light reflects off the stunning countertops and decorative mirrored backsplash adorning additional countertop space and even more cabinet storage for all of your culinary supplies. The dining area sits right next to the kitchen, centered around a beautiful bay window and wooden beamed ceiling with an artistically designed chandelier. The split floor plan is tastefully done with the master off to one side featuring a large ensuite bathroom with dual closets, a seating area, a large tub and walk in shower. To the other side of the living space is a hallway with the additional three bedrooms, a bathroom, the indoor laundry room with garage access and a flight of stairs leading up to the loft overlooking the downstairs that can be used in a number of creative ways. Exiting through either the main living area or the dining room, you will walk out onto a beautifully redone patio featuring marble tile under cover with a large ceiling fan. The backyard of this home is something out of your imagination, fully encompassed by a newer wood fence and featuring a fire pit and a hand constructed tree house with ninja warrior vibes, not to mention the newly installed heated pool featuring a sizeable sun shelf and color-changing lights to keep the fun going well into the evening hours. The sheer size of the backyard alone will have you continuously coming up with ways to take the fun outdoors. With neighborhood lake access, zoning for top rated schools and close proximity to everything the cities of Maitland and Winter Park have to offer, this is the one you won’t want to miss. Schedule your life-changing showing today!

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

The home you’ve been searching for has officially hit the market! Welcome to 2047 Howell Branch Road, the four bedroom, two bath home offering 2960 square feet of pure comfort. The beautiful exterior with its striking curb appeal will immediately draw you in before you even set foot inside. Entering through the foyer, you will feel a welcoming ambiance being flanked by a home office on one side and a multi purpose room on the other, flowing right into the wide open living spaces straight ahead. The family room features a brick fireplace, high cathedral ceilings and so much natural light seamlessly connecting to the kitchen, which has been updated to perfection. The large island has a beautiful stainless farmhouse sink and the cooktop encompassed inside the whitewashed brick nook will tempt even the most novice chef into whipping up an extravagant meal. The abundant natural light reflects off the stunning countertops and decorative mirrored backsplash adorning additional countertop space and even more cabinet storage for all of your culinary supplies. The dining area sits right next to the kitchen, centered around a beautiful bay window and wooden beamed ceiling with an artistically designed chandelier. The split floor plan is tastefully done with the master off to one side featuring a large ensuite bathroom with dual closets, a seating area, a large tub and walk in shower. To the other side of the living space is a hallway with the additional three bedrooms, a bathroom, the indoor laundry room with garage access and a flight of stairs leading up to the loft overlooking the downstairs that can be used in a number of creative ways. Exiting through either the main living area or the dining room, you will walk out onto a beautifully redone patio featuring marble tile under cover with a large ceiling fan. The backyard of this home is something out of your imagination, fully encompassed by a newer wood fence and featuring a fire pit and a hand constructed tree house with ninja warrior vibes, not to mention the newly installed heated pool featuring a sizeable sun shelf and color-changing lights to keep the fun going well into the evening hours. The sheer size of the backyard alone will have you continuously coming up with ways to take the fun outdoors. With neighborhood lake access, zoning for top rated schools and close proximity to everything the cities of Maitland and Winter Park have to offer, this is the one you won’t want to miss. Schedule your life-changing showing today!

2047 Howell Branch Road, Maitland

$1,100,000

One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer & this property qualifies for a credit up to $17,250 through the seller's preferred lender | Welcome to Versailles, where timeless style meets a top to bottom 2025 RENOVATION that redefines luxury living! Taken down to the studs and rebuilt with intention, this private POOL HOME is the one you have been waiting for. Major mechanical updates include: FULL REWIRE & ELECTRICAL (2025) | ALL NEW PLUMBING (2025) | WATER HEATER (2025) | Most windows replaced with HIGH END SLIDING GLASS DOORS (2025) | FRESH EXTERIOR PAINT (2025) | NEW ROOF (2023) | A/C (2014). Inside, the layout is bright, open and effortlessly liveable evidenced in the soaring ceilings and architectural details – including wood beam accents, a dramatic floor to ceiling fireplace, and a catwalk style second floor that creates an elevated yet inviting vibe. The great room connects the family room, kitchen, and dining areas, all with views to the pool and backyard thanks to an entire back wall of windows and sliding doors. OPTIONAL 4TH BEDROOM IS THE FORMAL LIVING ROOM AND CAN BE ENCLOSED AS THE BUYER DESIRES FOR OFFICE/ 4TH BEDROOM NEEDS. The magazine worthy kitchen is equal parts chic and functional featuring solid wood two-tone cabinetry, an OVERSIZED ISLAND WITH BAR SEATING, high end appliances (including an INDUCTION COOKTOP!), and a CUSTOM WALK-IN PANTRY for all your storage needs. Just off the dining area, a cozy sunken living room adds additional versatile space for everyday living or entertaining. Your MAIN FLOOR OWNER’S SUITE is a spectacular retreat; light filled and spacious with a CUSTOM DESIGNED WALK-IN CLOSET and spa-caliber bathroom delivering ZERO ENTRY DUAL MOEN SHOWERS with digital temperature and pressure controls, and sleek finishes throughout. Upstairs, two generous bedrooms and a large guest bath with a free standing acrylic soaking tub and separate shower offer comfort and style for family or guests. Also noteworthy; your laundry room is outfitted with smart, space saving solutions that include a state of the art combination washer/dryer and abundant storage. Outside, your PRIVATE BACKYARD OASIS awaits – a large open air pool with brand new pavers and lush landscaping, all fully fenced on a .30 ACRE LOT with a covered lanai – plus mature trees, a convenient circular driveway and endless curb appeal to round out the exterior. Additional highlights; light-toned ENGINEERED HARDWARD FLOORS and UPGRADED TILE THROUGHOUT, ideal split bedroom layout, attic storage in the garage, an optional HOA and you are ZONED FOR TOP-RATED SCHOOLS. Lake Minnehaha is visible just across the street and you are only minutes from Maitland Blvd, I-4, 436 and the area’s best shopping, dining, several parks and tons of recreation. Style, substance and location, this home is the total package. Schedule your tour today and come experience quiet luxury with a modern edge in your new Maitland pool home!

4 Beds ⋅ 3 Baths ⋅ Versailles SubDv. ⋅ 32751 Zip Code

One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer & this property qualifies for a credit up to $17,250 through the seller's preferred lender | Welcome to Versailles, where timeless style meets a top to bottom 2025 RENOVATION that redefines luxury living! Taken down to the studs and rebuilt with intention, this private POOL HOME is the one you have been waiting for. Major mechanical updates include: FULL REWIRE & ELECTRICAL (2025) | ALL NEW PLUMBING (2025) | WATER HEATER (2025) | Most windows replaced with HIGH END SLIDING GLASS DOORS (2025) | FRESH EXTERIOR PAINT (2025) | NEW ROOF (2023) | A/C (2014). Inside, the layout is bright, open and effortlessly liveable evidenced in the soaring ceilings and architectural details – including wood beam accents, a dramatic floor to ceiling fireplace, and a catwalk style second floor that creates an elevated yet inviting vibe. The great room connects the family room, kitchen, and dining areas, all with views to the pool and backyard thanks to an entire back wall of windows and sliding doors. OPTIONAL 4TH BEDROOM IS THE FORMAL LIVING ROOM AND CAN BE ENCLOSED AS THE BUYER DESIRES FOR OFFICE/ 4TH BEDROOM NEEDS. The magazine worthy kitchen is equal parts chic and functional featuring solid wood two-tone cabinetry, an OVERSIZED ISLAND WITH BAR SEATING, high end appliances (including an INDUCTION COOKTOP!), and a CUSTOM WALK-IN PANTRY for all your storage needs. Just off the dining area, a cozy sunken living room adds additional versatile space for everyday living or entertaining. Your MAIN FLOOR OWNER’S SUITE is a spectacular retreat; light filled and spacious with a CUSTOM DESIGNED WALK-IN CLOSET and spa-caliber bathroom delivering ZERO ENTRY DUAL MOEN SHOWERS with digital temperature and pressure controls, and sleek finishes throughout. Upstairs, two generous bedrooms and a large guest bath with a free standing acrylic soaking tub and separate shower offer comfort and style for family or guests. Also noteworthy; your laundry room is outfitted with smart, space saving solutions that include a state of the art combination washer/dryer and abundant storage. Outside, your PRIVATE BACKYARD OASIS awaits – a large open air pool with brand new pavers and lush landscaping, all fully fenced on a .30 ACRE LOT with a covered lanai – plus mature trees, a convenient circular driveway and endless curb appeal to round out the exterior. Additional highlights; light-toned ENGINEERED HARDWARD FLOORS and UPGRADED TILE THROUGHOUT, ideal split bedroom layout, attic storage in the garage, an optional HOA and you are ZONED FOR TOP-RATED SCHOOLS. Lake Minnehaha is visible just across the street and you are only minutes from Maitland Blvd, I-4, 436 and the area’s best shopping, dining, several parks and tons of recreation. Style, substance and location, this home is the total package. Schedule your tour today and come experience quiet luxury with a modern edge in your new Maitland pool home!

941 Versailles Circle, Maitland

$6,650,000

Sold data entry.

4 Beds ⋅ 6 Baths ⋅ Hollieanna Shores 1st Add SubDv. ⋅ 32751 Zip Code

Sold data entry.

119 Whitecaps Circle, Maitland

$1,075,000

One or more photo(s) has been virtually staged. Accepted offer with home sale contingency. Seller will consider backup offers. Nestled in the heart of gated, sought-after Lake Colony Estates, this luxurious 5-bedroom, 5-bathroom pool home offers unparalleled elegance, space, and resort-style living. Meticulously crafted with custom designer details, this property boasts soaring 14’ ceilings, coffered and crown molding, wainscoting, and maple cabinetry—blending timeless sophistication with modern comfort. Exquisite Interior Features: Sprawling open floor plan with oversized rooms, perfect for grand-scale entertaining and everyday living. Gourmet kitchen with solid-surface counters, premium appliances, and abundant custom cabinetry. Grand family room with custom built-ins and a fireplace, bathed in natural light. Downstairs primary retreat featuring dual vanities, a soaking tub, walk-in closets, and a lavish shower. First-floor guest suite plus three additional bedrooms upstairs, including a huge bonus room ideal for a media lounge or playroom. Elegant office/den with custom built-in shelving, perfect for remote work or a private library. Outdoor Oasis & Location Perks: Sparkling pool surrounded by a paver deck and lush, mature landscaping—your private sanctuary for relaxation. Tree-lined streets with sidewalks in a premier gated community, just minutes to top-rated schools, shopping, and dining. Unbeatable convenience: Close to everything that you would need including restaurants, shops, highways and minutes to Park Avenue. Walkable to Orangewood School, 5 min to Maitland Blvd & I-4 Express Lanes (20 min to downtown Orlando, 30 min to airports) <1 hour to Florida’s beaches. Why This Home Stands Out: Lowest-priced estate in Lake Colony Estates—offering exceptional value for a custom-built luxury home. Prime interior lot on a quiet, desirable street in the middle of the block. Don’t miss this rare opportunity to own one of Lake Colony’s finest properties—a perfect blend of luxury, location, and lifestyle.

5 Beds ⋅ 5 Baths ⋅ Lake Colony Ph 01 Rep SubDv. ⋅ 32751 Zip Code

One or more photo(s) has been virtually staged. Accepted offer with home sale contingency. Seller will consider backup offers. Nestled in the heart of gated, sought-after Lake Colony Estates, this luxurious 5-bedroom, 5-bathroom pool home offers unparalleled elegance, space, and resort-style living. Meticulously crafted with custom designer details, this property boasts soaring 14’ ceilings, coffered and crown molding, wainscoting, and maple cabinetry—blending timeless sophistication with modern comfort. Exquisite Interior Features: Sprawling open floor plan with oversized rooms, perfect for grand-scale entertaining and everyday living. Gourmet kitchen with solid-surface counters, premium appliances, and abundant custom cabinetry. Grand family room with custom built-ins and a fireplace, bathed in natural light. Downstairs primary retreat featuring dual vanities, a soaking tub, walk-in closets, and a lavish shower. First-floor guest suite plus three additional bedrooms upstairs, including a huge bonus room ideal for a media lounge or playroom. Elegant office/den with custom built-in shelving, perfect for remote work or a private library. Outdoor Oasis & Location Perks: Sparkling pool surrounded by a paver deck and lush, mature landscaping—your private sanctuary for relaxation. Tree-lined streets with sidewalks in a premier gated community, just minutes to top-rated schools, shopping, and dining. Unbeatable convenience: Close to everything that you would need including restaurants, shops, highways and minutes to Park Avenue. Walkable to Orangewood School, 5 min to Maitland Blvd & I-4 Express Lanes (20 min to downtown Orlando, 30 min to airports) <1 hour to Florida’s beaches. Why This Home Stands Out: Lowest-priced estate in Lake Colony Estates—offering exceptional value for a custom-built luxury home. Prime interior lot on a quiet, desirable street in the middle of the block. Don’t miss this rare opportunity to own one of Lake Colony’s finest properties—a perfect blend of luxury, location, and lifestyle.

307 Running Wind Lane, Maitland

$1,525,000

Private Maitland Estate | Grand Living on 1.47 Acres. Welcome to 685 Mayo Avenue—an exceptional private estate nestled in one of Maitland’s most coveted neighborhoods. Set on expansive, lush, well-maintained grounds, this 4-bedroom, 4-bathroom, and 2 half bath home offers the perfect blend of refined elegance, modern comfort, and resort-style amenities across nearly 4,000 square feet of living space. From the moment you arrive, the long, private 375-foot paver driveway, mature oak trees, and tropical landscaping create an unforgettable sense of arrival. Inside, a gracious foyer welcomes you into an open-concept layout, thoughtfully designed for both everyday living and upscale entertaining. The gourmet kitchen is a chef’s dream—granite countertops, stainless steel appliances, gas cooktop, and custom cabinetry—all overlooking the spacious family room. French doors on all the first-floor living areas leading directly to a resort-style pool and patio, offering the perfect indoor-outdoor flow for relaxing or hosting guests. The primary suite is a serene escape with dual walk-in closets and a spa-like bath featuring travertine floors, dual vanities, a Jacuzzi tub, and a walk-in shower. Upstairs, three generously sized bedrooms include a Jack-and-Jill bath and a private bath off the third bedroom. A built-in desk area and laundry room complete the second floor. Need space for guests or extended family? The third floor of the home offers a unique flex space for movies, a pool table or a man cave. Plus, nearly 1,100 sqft of living space boasting a one-bedroom, one-bath, guest apartment above the garage that has been beautifully updated and offers complete privacy. Additional highlights include: Dedicated home office on the main level | Third-floor bonus room | Two half-baths, including a dedicated pool bath | Resort sized patio & pool | Three newer HVAC systems | Oversized 3-car garage | 1 bed/ 1 bath, 1000sqft, ADU above the garage that is not included in MLS. Perfectly positioned just minutes from top-rated schools, Lake Maitland, Park Avenue, and downtown Orlando, this estate offers the rare opportunity to own a one-of-a-kind property in an unbeatable location. Schedule your private tour today and discover what makes this Maitland estate truly exceptional.

4 Beds ⋅ 6 Baths ⋅ Maitland Forest SubDv. ⋅ 32751 Zip Code

Private Maitland Estate | Grand Living on 1.47 Acres. Welcome to 685 Mayo Avenue—an exceptional private estate nestled in one of Maitland’s most coveted neighborhoods. Set on expansive, lush, well-maintained grounds, this 4-bedroom, 4-bathroom, and 2 half bath home offers the perfect blend of refined elegance, modern comfort, and resort-style amenities across nearly 4,000 square feet of living space. From the moment you arrive, the long, private 375-foot paver driveway, mature oak trees, and tropical landscaping create an unforgettable sense of arrival. Inside, a gracious foyer welcomes you into an open-concept layout, thoughtfully designed for both everyday living and upscale entertaining. The gourmet kitchen is a chef’s dream—granite countertops, stainless steel appliances, gas cooktop, and custom cabinetry—all overlooking the spacious family room. French doors on all the first-floor living areas leading directly to a resort-style pool and patio, offering the perfect indoor-outdoor flow for relaxing or hosting guests. The primary suite is a serene escape with dual walk-in closets and a spa-like bath featuring travertine floors, dual vanities, a Jacuzzi tub, and a walk-in shower. Upstairs, three generously sized bedrooms include a Jack-and-Jill bath and a private bath off the third bedroom. A built-in desk area and laundry room complete the second floor. Need space for guests or extended family? The third floor of the home offers a unique flex space for movies, a pool table or a man cave. Plus, nearly 1,100 sqft of living space boasting a one-bedroom, one-bath, guest apartment above the garage that has been beautifully updated and offers complete privacy. Additional highlights include: Dedicated home office on the main level | Third-floor bonus room | Two half-baths, including a dedicated pool bath | Resort sized patio & pool | Three newer HVAC systems | Oversized 3-car garage | 1 bed/ 1 bath, 1000sqft, ADU above the garage that is not included in MLS. Perfectly positioned just minutes from top-rated schools, Lake Maitland, Park Avenue, and downtown Orlando, this estate offers the rare opportunity to own a one-of-a-kind property in an unbeatable location. Schedule your private tour today and discover what makes this Maitland estate truly exceptional.

685 Mayo Avenue, Maitland

$1,220,000

Rare opportunity to own a beautifully maintained pool home in Dommerich Estates with lake access to Lake Minnehaha and the Winter Park Chain of Lakes. This spacious and versatile 6 bedrooms, 4 bathrooms home features a split floor plan, a two-car garage, and a generous bonus room, making it ideal for families of all sizes. The interior offers an inviting layout, including a large primary suite with dual walk-in closets, a soaking tub, double vanity, separate shower, and an attached study that adjoins another bedroom—perfect for a nursery or home office. The open-concept living room flows seamlessly into a gourmet kitchen, creating an ideal space for entertaining. Additional highlights include a gas fireplace, wood floors, crown molding, a wine cellar for the enthusiast, and thoughtful bedroom arrangements including a Jack and Jill bath and another ensuite. The home also features a convenient laundry room with direct access to the pool deck, as well as an upstairs bonus room with ample storage. Above the garage, you’ll find a secondary primary ensuite with a walk-in closet—ideal for guests, in-laws, or older children seeking privacy. Situated on an oversized, fenced lot, the backyard is a tranquil retreat with a saltwater pool, pavered lanai, fire pit, outdoor shower, and space for a dog run or additional storage for a boat, golf cart, or other recreational vehicles. There's also extra parking available next to the driveway. Located in the highly sought-after Dommerich Elementary and Winter Park High school zone, and with no HOA, this home offers comfort, convenience, and community in one of Maitland’s most established neighborhoods.

6 Beds ⋅ 4 Baths ⋅ Dommerich Estates SubDv. ⋅ 32751 Zip Code

Rare opportunity to own a beautifully maintained pool home in Dommerich Estates with lake access to Lake Minnehaha and the Winter Park Chain of Lakes. This spacious and versatile 6 bedrooms, 4 bathrooms home features a split floor plan, a two-car garage, and a generous bonus room, making it ideal for families of all sizes. The interior offers an inviting layout, including a large primary suite with dual walk-in closets, a soaking tub, double vanity, separate shower, and an attached study that adjoins another bedroom—perfect for a nursery or home office. The open-concept living room flows seamlessly into a gourmet kitchen, creating an ideal space for entertaining. Additional highlights include a gas fireplace, wood floors, crown molding, a wine cellar for the enthusiast, and thoughtful bedroom arrangements including a Jack and Jill bath and another ensuite. The home also features a convenient laundry room with direct access to the pool deck, as well as an upstairs bonus room with ample storage. Above the garage, you’ll find a secondary primary ensuite with a walk-in closet—ideal for guests, in-laws, or older children seeking privacy. Situated on an oversized, fenced lot, the backyard is a tranquil retreat with a saltwater pool, pavered lanai, fire pit, outdoor shower, and space for a dog run or additional storage for a boat, golf cart, or other recreational vehicles. There's also extra parking available next to the driveway. Located in the highly sought-after Dommerich Elementary and Winter Park High school zone, and with no HOA, this home offers comfort, convenience, and community in one of Maitland’s most established neighborhoods.

1653 Cheyenne Trail, Maitland

$3,950,000

Exquisite contemporary waterfront retreat in Maitland. Experience modern luxury and serene waterfront living in this breathtaking five-bedroom, 5.5-bath canal-front home, newly built in 2024. Positioned on a quiet dead-end street in Maitland, this architectural masterpiece offers an unparalleled lifestyle on the Winter Park Chain of Lakes. Enter through the stunning 10-foot glass pivot door into a soaring foyer where a floating wood and glass staircase sets a dramatic tone. The expansive great room boasts a two-story ceiling and a wall of glass doors that seamlessly blend indoor and outdoor living. Go outside to your private oasis featuring a covered lanai with remote-controlled screens, a summer kitchen, gas fireplace, resort-style pool and spa, putting green, and a covered boat dock with a lift and jet ski platform, all overlooking tranquil Howell Branch Creek with direct access to Lake Maitland. The heart of the home is the chef-inspired kitchen, complete with dual oversized islands, sleek high-gloss custom cabinetry, integrated refrigerator and freezer columns, a wine refrigerator, built-in coffee maker, and a striking hood vent above a six-burner gas range. Adjacent is a stylish dining room framed by a floor-to-ceiling glass wall offering captivating water views. The main-level primary suite is a sanctuary with a private sitting area, dual walk-in closets, and a spa-style marble wet room with combined soaking tub and rainfall shower. A home office with lush front yard views, an elegant guest suite, a full bath, and the first of two laundry rooms complete the first floor. Take the elevator or statement staircase to the second level, where you'll find two additional bedrooms with en suites and walk-in closets, a fifth bedroom, a full bath, a second laundry room, and a 24-by-14-foot game room with wet bar, ideal for entertaining. Additional highlights include a three-car side-entry garage, an outdoor shower, a storage room, and verdant landscaping adorned with majestic cypress and oak trees draped in Spanish moss. Just minutes from the boutiques and fine dining of Winter Park’s Park Avenue, with easy access to major highways, hospitals, and both international and executive airports. This is Florida luxury redefined, private, peaceful and perfectly appointed.

5 Beds ⋅ 5 Baths ⋅ Maitland Shores SubDv. ⋅ 32751 Zip Code

Exquisite contemporary waterfront retreat in Maitland. Experience modern luxury and serene waterfront living in this breathtaking five-bedroom, 5.5-bath canal-front home, newly built in 2024. Positioned on a quiet dead-end street in Maitland, this architectural masterpiece offers an unparalleled lifestyle on the Winter Park Chain of Lakes. Enter through the stunning 10-foot glass pivot door into a soaring foyer where a floating wood and glass staircase sets a dramatic tone. The expansive great room boasts a two-story ceiling and a wall of glass doors that seamlessly blend indoor and outdoor living. Go outside to your private oasis featuring a covered lanai with remote-controlled screens, a summer kitchen, gas fireplace, resort-style pool and spa, putting green, and a covered boat dock with a lift and jet ski platform, all overlooking tranquil Howell Branch Creek with direct access to Lake Maitland. The heart of the home is the chef-inspired kitchen, complete with dual oversized islands, sleek high-gloss custom cabinetry, integrated refrigerator and freezer columns, a wine refrigerator, built-in coffee maker, and a striking hood vent above a six-burner gas range. Adjacent is a stylish dining room framed by a floor-to-ceiling glass wall offering captivating water views. The main-level primary suite is a sanctuary with a private sitting area, dual walk-in closets, and a spa-style marble wet room with combined soaking tub and rainfall shower. A home office with lush front yard views, an elegant guest suite, a full bath, and the first of two laundry rooms complete the first floor. Take the elevator or statement staircase to the second level, where you'll find two additional bedrooms with en suites and walk-in closets, a fifth bedroom, a full bath, a second laundry room, and a 24-by-14-foot game room with wet bar, ideal for entertaining. Additional highlights include a three-car side-entry garage, an outdoor shower, a storage room, and verdant landscaping adorned with majestic cypress and oak trees draped in Spanish moss. Just minutes from the boutiques and fine dining of Winter Park’s Park Avenue, with easy access to major highways, hospitals, and both international and executive airports. This is Florida luxury redefined, private, peaceful and perfectly appointed.

33 Eastwind Lane, Maitland

$3,500,000

An exclusive opportunity to own a lakefront parcel on the shimmering shores of Lake Maitland, part of the sought-after Winter Park Chain of Lakes. Encompassing approximately 1.45 acres, this estate site boasts over 100 waterfront feet, offering unmatched views, serenity, and potential for a truly custom dream home. Positioned on the northern banks of Lake Maitland in the heart of Adams Grove, this estate site is a rare jewel. Enjoy proximity to downtown Winter Park's Park Avenue, renowned for its boutiques, galleries, fine dining and cultural experiences. With direct frontage on Lake Maitland, your future home can enjoy luxury boating, sunset cruises, paddle boarding and kayaking. The tranquil waters create a captivating backdrop for everyday living and grand entertaining as well as postcard-worthy sunsets. This expansive lot invites architectural brilliance, design your custom sanctuary that reflects your personal lifestyle and aesthetic. Whether you're seeking an extraordinary primary residence or a signature second home, 1770 East Adams Drive presents a rare blend of privacy, elegance and natural splendor in one of Central Florida's desirable settings.

Adams Grove SubDv. ⋅ 32751 Zip Code

An exclusive opportunity to own a lakefront parcel on the shimmering shores of Lake Maitland, part of the sought-after Winter Park Chain of Lakes. Encompassing approximately 1.45 acres, this estate site boasts over 100 waterfront feet, offering unmatched views, serenity, and potential for a truly custom dream home. Positioned on the northern banks of Lake Maitland in the heart of Adams Grove, this estate site is a rare jewel. Enjoy proximity to downtown Winter Park's Park Avenue, renowned for its boutiques, galleries, fine dining and cultural experiences. With direct frontage on Lake Maitland, your future home can enjoy luxury boating, sunset cruises, paddle boarding and kayaking. The tranquil waters create a captivating backdrop for everyday living and grand entertaining as well as postcard-worthy sunsets. This expansive lot invites architectural brilliance, design your custom sanctuary that reflects your personal lifestyle and aesthetic. Whether you're seeking an extraordinary primary residence or a signature second home, 1770 East Adams Drive presents a rare blend of privacy, elegance and natural splendor in one of Central Florida's desirable settings.

1770 E Adams Drive, Maitland

$1,200,000

Stunning Estate Home in Maitland Club! Welcome home to this renovated, 4-bedroom, 3.5 bath pool home with 2-car garage. Offering 3,870 Sf of luxurious living space including formal living and dining rooms, a home office, family room, & more. Sophisticated updates have been recently completed, including a BRAND-NEW ROOF (2024), hexagon tile in the office and living room, accent wall with fireplace, and a modern kitchen that showcases high-end black appliances, contrasting cabinets and bright white Quartz countertops, brass hardware, and a herringbone backsplash. French doors off the living, family, and primary bedroom open to the covered lanai and provide pool views from every angle within the home. The first-floor primary bedrooms is generously sized and has a gorgeous en suite that's been updated with a new double-sink vanity, new lighting, new soaking tub, and new walk-in shower with elevated subway tiling. Upstairs are 3 additional bedrooms each with ample closet space and a hall bath. You'll enjoy spending time underneath the covered lanai and taking advantage of the beautiful pool during Florida's summer months. This home offers a quiet backyard wtih a brick wall for extra privacy. Located in Maitland Club residents of this community enjoy 24-hour guard gate access, quiet streets with sidewalks for walkability, and community tennis courts. Zoned for Lake Sybelia Elementary, Maitland Middle, and Edgewater High and within minutes of highly-rated private schools there are plenty of A-rated schools just around the corner. Showings are by appointment only, schedule yours today.

4 Beds ⋅ 4 Baths ⋅ Maitland Club Rep SubDv. ⋅ 32751 Zip Code

Stunning Estate Home in Maitland Club! Welcome home to this renovated, 4-bedroom, 3.5 bath pool home with 2-car garage. Offering 3,870 Sf of luxurious living space including formal living and dining rooms, a home office, family room, & more. Sophisticated updates have been recently completed, including a BRAND-NEW ROOF (2024), hexagon tile in the office and living room, accent wall with fireplace, and a modern kitchen that showcases high-end black appliances, contrasting cabinets and bright white Quartz countertops, brass hardware, and a herringbone backsplash. French doors off the living, family, and primary bedroom open to the covered lanai and provide pool views from every angle within the home. The first-floor primary bedrooms is generously sized and has a gorgeous en suite that's been updated with a new double-sink vanity, new lighting, new soaking tub, and new walk-in shower with elevated subway tiling. Upstairs are 3 additional bedrooms each with ample closet space and a hall bath. You'll enjoy spending time underneath the covered lanai and taking advantage of the beautiful pool during Florida's summer months. This home offers a quiet backyard wtih a brick wall for extra privacy. Located in Maitland Club residents of this community enjoy 24-hour guard gate access, quiet streets with sidewalks for walkability, and community tennis courts. Zoned for Lake Sybelia Elementary, Maitland Middle, and Edgewater High and within minutes of highly-rated private schools there are plenty of A-rated schools just around the corner. Showings are by appointment only, schedule yours today.

960 Brightwater Circle, Maitland

$2,250,000

Presenting a stunning new construction residence located on a quiet cul-de-sac offering a seamless blend of luxury, functionality and modern design. The main home features four spacious bedroom suites, a dedicated office and a bonus/flex area, 4 full baths and 2 half baths, while the property also includes a rare-to-find one-level detached 1,143 sf 2BE/2BA guest house that includes a kitchen and a living area... *** ideal for for multi-generational living, spacious home office, live-ins or long term guests… Beautiful wood floors extend throughout the main house living spaces, complemented by designer porcelain tile in all baths. The open floor plan showcases soaring 21-foot ceilings in the great room and dining area, anchored by a beautiful chef’s kitchen complete with a dual-fuel range, quartz waterfall island, custom blended cabinetry and an adjacent walk-in pantry. A wall of sliding glass doors in the great room opens to the expansive covered lanai and new Pebble Tec pool with autofill and auto-drain features, all surrounded by travertine decking and a masonry and aluminum privacy fence. The first-floor primary suite offers a serene retreat with private pool courtyard views, a custom walk-in closet and a spa-inspired bath with marble floors, a spacious walk-in shower and a separate soaking tub. Upstairs, there are three additional bedroom suites and a versatile loft to provide ideal space for relaxation lounge area. The side-entry two-car garage includes epoxy floors, EV charging readiness and direct access to the mudroom, laundry, pantry and kitchen for everyday convenience. Designed for year-round entertainment, the covered lanai is stubbed and ready for a summer kitchen, with additional outdoor space available for expanded amenities. Both main and guest houses are bathed in natural light thanks to generous architecturally enhancing windows and glass doors. Modern comforts include smart lighting, exterior security cameras and a built-in audio system. On a quiet cul-de-sac, this property is within visiting or biking distance to Maitland Community Park, a 25-acre wooded park with tennis courts, basketball, playgrounds, trails and pavilions! Enjoy easy access to other downtown Maitland amenities, 7-10 minute drive to Park Avenue in downtown Winter Park, quick access to major roadways & I-4, downtown Orlando, area hospitals, and both executive and international airports... Zoned for regarded Lake Sybelia Elementary, Maitland Middle and Winter Park High School, this exceptional home is a rare offering in a secluded, wonderful neighborhood.

6 Beds ⋅ 8 Baths ⋅ Terra Place SubDv. ⋅ 32751 Zip Code

Presenting a stunning new construction residence located on a quiet cul-de-sac offering a seamless blend of luxury, functionality and modern design. The main home features four spacious bedroom suites, a dedicated office and a bonus/flex area, 4 full baths and 2 half baths, while the property also includes a rare-to-find one-level detached 1,143 sf 2BE/2BA guest house that includes a kitchen and a living area... *** ideal for for multi-generational living, spacious home office, live-ins or long term guests… Beautiful wood floors extend throughout the main house living spaces, complemented by designer porcelain tile in all baths. The open floor plan showcases soaring 21-foot ceilings in the great room and dining area, anchored by a beautiful chef’s kitchen complete with a dual-fuel range, quartz waterfall island, custom blended cabinetry and an adjacent walk-in pantry. A wall of sliding glass doors in the great room opens to the expansive covered lanai and new Pebble Tec pool with autofill and auto-drain features, all surrounded by travertine decking and a masonry and aluminum privacy fence. The first-floor primary suite offers a serene retreat with private pool courtyard views, a custom walk-in closet and a spa-inspired bath with marble floors, a spacious walk-in shower and a separate soaking tub. Upstairs, there are three additional bedroom suites and a versatile loft to provide ideal space for relaxation lounge area. The side-entry two-car garage includes epoxy floors, EV charging readiness and direct access to the mudroom, laundry, pantry and kitchen for everyday convenience. Designed for year-round entertainment, the covered lanai is stubbed and ready for a summer kitchen, with additional outdoor space available for expanded amenities. Both main and guest houses are bathed in natural light thanks to generous architecturally enhancing windows and glass doors. Modern comforts include smart lighting, exterior security cameras and a built-in audio system. On a quiet cul-de-sac, this property is within visiting or biking distance to Maitland Community Park, a 25-acre wooded park with tennis courts, basketball, playgrounds, trails and pavilions! Enjoy easy access to other downtown Maitland amenities, 7-10 minute drive to Park Avenue in downtown Winter Park, quick access to major roadways & I-4, downtown Orlando, area hospitals, and both executive and international airports... Zoned for regarded Lake Sybelia Elementary, Maitland Middle and Winter Park High School, this exceptional home is a rare offering in a secluded, wonderful neighborhood.

734 Terra Place, 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

$2,535,000

Completed New Construction 2024 | Lakefront Luxury | Below Appraised Value: This extraordinary custom lakefront residence was built by Dave Konkol & is elevated on a 0.56-acre corner lot w/ approximately 112’ of lake frontage. Featuring a crisp stucco exterior, impact windows & remote-operated screened porches, the home is surrounded by professionally designed native landscaping & butterfly gardens which set the stage for a lifestyle defined by natural beauty, enduring materials, timeless design & everyday comfort. Once inside, the open floor plan showcases wide-plank, white oak engineered wood flooring & is filled w/ natural light from the large format windows that frame views of the backyard pool & serene Lake Sybelia out front. A formal dining space connects to a wet bar & opens to a functional yet casually elegant kitchen. Quartz countertops, custom soft-close cabinetry with pull-outs & a full suite of premium appliances lend functionality & refinement to the kitchen. A large walk-in pantry & adjacent drop zone add quality of life to the beautifully tailored design. The main-level primary suite is a sanctuary w/ lake views, remote-controlled blackout shades, decorative wood ceiling beams, a customized walk-in closet & a spa-like bathroom featuring Frank Lloyd Wright Brizo plumbing fixtures, a long vanity stained to match the fixtures, dual sinks, an oversized glass-enclosed shower with 21” rainhead, soaking tub & private water closet. A guest bedroom w/ adjacent full bath also functions as a pool and powder bath. The large laundry room w/ quartz countertops, GE Profile front-loading washer and dryer & a Laundry Jet Swift pneumatic laundry chute—connected to the primary suite & upstairs bedrooms and complete the main floor. Upstairs, two additional bedrooms with wide water views include customized closets & designer baths. The cozy loft and Bonus spaces flex easily for work, wellness, or play. Other interior features include built-in speakers, custom millwork, motorized blinds & smart-home wiring to enhance comfort and livability. Seamless indoor-outdoor transitions define the rear living experience, where a deep covered lanai includes recessed lighting, fans, speakers & motorized screens opening to a 7’ deep, heated, saltwater pool w/ sunshelf, outdoor shower & direct access to a full bathroom. The fenced backyard offers ample space for play, relaxation & a dog run. A custom dock w/ composite decking & covered boat lift sits on Lake Sybelia—offering year-round opportunities for boating, paddle-boarding, swimming & fishing on waters with no public access. Efficiency abounds thanks to a PES Solar system featuring 58 REC panels, four Enphase battery backups & real-time energy monitoring. Additional features include Trane HVAC systems, a commercial-grade water heater w/ recirculating pump & a new irrigation system w/ pump fed by lake water. The three-car garage includes modern paneled doors w/ openers and extra storage. Now unexpectedly available due to a change in the owners’ plans, this is a rare opportunity to purchase an almost-new custom home—combining advanced systems with timeless design—in one of Maitland’s most beloved neighborhoods, just minutes from Lake Lily Park, downtown Maitland, major thoroughfares and Winter Park’s shops and restaurants.

5 Beds ⋅ 4 Baths ⋅ Sybelia Shores Second Add SubDv. ⋅ 32751 Zip Code

Completed New Construction 2024 | Lakefront Luxury | Below Appraised Value: This extraordinary custom lakefront residence was built by Dave Konkol & is elevated on a 0.56-acre corner lot w/ approximately 112’ of lake frontage. Featuring a crisp stucco exterior, impact windows & remote-operated screened porches, the home is surrounded by professionally designed native landscaping & butterfly gardens which set the stage for a lifestyle defined by natural beauty, enduring materials, timeless design & everyday comfort. Once inside, the open floor plan showcases wide-plank, white oak engineered wood flooring & is filled w/ natural light from the large format windows that frame views of the backyard pool & serene Lake Sybelia out front. A formal dining space connects to a wet bar & opens to a functional yet casually elegant kitchen. Quartz countertops, custom soft-close cabinetry with pull-outs & a full suite of premium appliances lend functionality & refinement to the kitchen. A large walk-in pantry & adjacent drop zone add quality of life to the beautifully tailored design. The main-level primary suite is a sanctuary w/ lake views, remote-controlled blackout shades, decorative wood ceiling beams, a customized walk-in closet & a spa-like bathroom featuring Frank Lloyd Wright Brizo plumbing fixtures, a long vanity stained to match the fixtures, dual sinks, an oversized glass-enclosed shower with 21” rainhead, soaking tub & private water closet. A guest bedroom w/ adjacent full bath also functions as a pool and powder bath. The large laundry room w/ quartz countertops, GE Profile front-loading washer and dryer & a Laundry Jet Swift pneumatic laundry chute—connected to the primary suite & upstairs bedrooms and complete the main floor. Upstairs, two additional bedrooms with wide water views include customized closets & designer baths. The cozy loft and Bonus spaces flex easily for work, wellness, or play. Other interior features include built-in speakers, custom millwork, motorized blinds & smart-home wiring to enhance comfort and livability. Seamless indoor-outdoor transitions define the rear living experience, where a deep covered lanai includes recessed lighting, fans, speakers & motorized screens opening to a 7’ deep, heated, saltwater pool w/ sunshelf, outdoor shower & direct access to a full bathroom. The fenced backyard offers ample space for play, relaxation & a dog run. A custom dock w/ composite decking & covered boat lift sits on Lake Sybelia—offering year-round opportunities for boating, paddle-boarding, swimming & fishing on waters with no public access. Efficiency abounds thanks to a PES Solar system featuring 58 REC panels, four Enphase battery backups & real-time energy monitoring. Additional features include Trane HVAC systems, a commercial-grade water heater w/ recirculating pump & a new irrigation system w/ pump fed by lake water. The three-car garage includes modern paneled doors w/ openers and extra storage. Now unexpectedly available due to a change in the owners’ plans, this is a rare opportunity to purchase an almost-new custom home—combining advanced systems with timeless design—in one of Maitland’s most beloved neighborhoods, just minutes from Lake Lily Park, downtown Maitland, major thoroughfares and Winter Park’s shops and restaurants.

705 N Lake Sybelia Drive, Maitland

$1,089,000

Maitland Mediterranean home with lake access to Lake Maitland and the WP chain of lakes. This well maintained home has 4 bedrooms and 3.5 baths with over 3000 square feet of living area. Spacious gourmet kitchen with separate eat-in area. Stainless appliances, granite countertops with bar seating opening out to the family room. French doors lead out to a covered patio overlooking the private backyard complete with a relaxing spa. Butlers pantry equipped with a wine refrigerator leads to the formal dining room. First floor primary bedroom with a large bath complete with soaker tub, separate shower, and 2 separate vanities. Second floor consists of 3 bedrooms, 2 baths, and a large gathering room perfect for kids and entertaining. This fabulous location in a sought after neighborhood, great schools, and easy access to eating and shopping.

4 Beds ⋅ 4 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code

Maitland Mediterranean home with lake access to Lake Maitland and the WP chain of lakes. This well maintained home has 4 bedrooms and 3.5 baths with over 3000 square feet of living area. Spacious gourmet kitchen with separate eat-in area. Stainless appliances, granite countertops with bar seating opening out to the family room. French doors lead out to a covered patio overlooking the private backyard complete with a relaxing spa. Butlers pantry equipped with a wine refrigerator leads to the formal dining room. First floor primary bedroom with a large bath complete with soaker tub, separate shower, and 2 separate vanities. Second floor consists of 3 bedrooms, 2 baths, and a large gathering room perfect for kids and entertaining. This fabulous location in a sought after neighborhood, great schools, and easy access to eating and shopping.

123 Tangelo Court, Maitland

$3,000,000

Sold data only

Maitland Forest SubDv. ⋅ 32751 Zip Code

Sold data only

656 Bentley Lane, Maitland