Homesinorlando.forsale Search Results

$159,000

Welcome to Lake Maitland Terrace, a charming lakeside community of Mid-Century Miami Modern condos set within eleven cottage-style buildings along the shores of Lake Maitland. Residents enjoy resort-style amenities, including a recently renovated lakeside pool, fishing dock, putting green, shuffleboard courts, and a clubhouse with kitchen. This first-floor, two-bedroom, one-bath condo in the Arlington Building has been maintained by the same owner for nearly 30 years. Updates include a 2021 AC, 4-year-old water heater, newer windows and front door, and a new roof (2023–2024). The open great room flows into the dining area, and the adjacent kitchen features a 2nd entrance. Much of the interior remains in original condition, and the old carpet has been removed, providing an ideal opportunity for a new owner to update and make it their own. Additional features include one designated parking space, ample guest parking, enclosed bicycle storage, convenient laundry facilities, and racks for kayaks and paddleboards. The location is unbeatable—walk to the Enzian Theater and Lake Lily, or drive just five minutes to downtown Winter Park with easy access to I-4. Condo is being sold AS IS.

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

Welcome to Lake Maitland Terrace, a charming lakeside community of Mid-Century Miami Modern condos set within eleven cottage-style buildings along the shores of Lake Maitland. Residents enjoy resort-style amenities, including a recently renovated lakeside pool, fishing dock, putting green, shuffleboard courts, and a clubhouse with kitchen. This first-floor, two-bedroom, one-bath condo in the Arlington Building has been maintained by the same owner for nearly 30 years. Updates include a 2021 AC, 4-year-old water heater, newer windows and front door, and a new roof (2023–2024). The open great room flows into the dining area, and the adjacent kitchen features a 2nd entrance. Much of the interior remains in original condition, and the old carpet has been removed, providing an ideal opportunity for a new owner to update and make it their own. Additional features include one designated parking space, ample guest parking, enclosed bicycle storage, convenient laundry facilities, and racks for kayaks and paddleboards. The location is unbeatable—walk to the Enzian Theater and Lake Lily, or drive just five minutes to downtown Winter Park with easy access to I-4. Condo is being sold AS IS.

1140 S Orlando Avenue Unit A5, Maitland

$540,000

Welcome to The Moorings, a rarely available lakeside community perfectly positioned across from beautiful Lake Lily. This fully renovated 4th-floor condo combines modern elegance with stunning water views of Lake Maitland, visible right from your living room and screened-in balcony. Inside, you’ll find an open, light-filled layout with white-oak luxury vinyl flooring that sets a clean, contemporary tone. The kitchen has been completely updated with premium appliances, quartz countertops, and brass fixtures, creating a space that’s both stylish and functional. The primary bedroom suite features a spacious walk-in closet and a beautifully finished en-suite bathroom with a large walk-in shower. A second bedroom and full bath offer plenty of room for guests or a home office. Additional conveniences include an in-unit laundry room with washer and dryer, plus elevator access for easy entry. Residents of The Moorings enjoy a host of amenities, including a sparkling community pool, private boat docks, a scenic pier with seating area, a fitness center, and a clubhouse for gatherings. Located just minutes from top-rated restaurants, shopping, and entertainment in Maitland and Winter Park, this condo offers the ideal blend of tranquility and city convenience. Come experience lakefront living at its finest.

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

Welcome to The Moorings, a rarely available lakeside community perfectly positioned across from beautiful Lake Lily. This fully renovated 4th-floor condo combines modern elegance with stunning water views of Lake Maitland, visible right from your living room and screened-in balcony. Inside, you’ll find an open, light-filled layout with white-oak luxury vinyl flooring that sets a clean, contemporary tone. The kitchen has been completely updated with premium appliances, quartz countertops, and brass fixtures, creating a space that’s both stylish and functional. The primary bedroom suite features a spacious walk-in closet and a beautifully finished en-suite bathroom with a large walk-in shower. A second bedroom and full bath offer plenty of room for guests or a home office. Additional conveniences include an in-unit laundry room with washer and dryer, plus elevator access for easy entry. Residents of The Moorings enjoy a host of amenities, including a sparkling community pool, private boat docks, a scenic pier with seating area, a fitness center, and a clubhouse for gatherings. Located just minutes from top-rated restaurants, shopping, and entertainment in Maitland and Winter Park, this condo offers the ideal blend of tranquility and city convenience. Come experience lakefront living at its finest.

206 Quayside Circle Unit 404, 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

$120,000

**ATTENTION INVESTORS** Take advantage of this great opportunity and Add this income producing property to your portfolio with tenant in place. Corner unit 1 bed 1 bath condo with new laminate floors and granite countertops. This second floor unit means there is no one above you and has a pool view located steps away. The mailbox and pool are only a few steps away. Location is walking distances to Publix, Starbucks and many other stores. It is also just a 10 min drive to Full Sail University and a 30 minute drive to the parks. Best location in Orlando! Best Return available!

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

**ATTENTION INVESTORS** Take advantage of this great opportunity and Add this income producing property to your portfolio with tenant in place. Corner unit 1 bed 1 bath condo with new laminate floors and granite countertops. This second floor unit means there is no one above you and has a pool view located steps away. The mailbox and pool are only a few steps away. Location is walking distances to Publix, Starbucks and many other stores. It is also just a 10 min drive to Full Sail University and a 30 minute drive to the parks. Best location in Orlando! Best Return available!

2517 Caper Lane Unit 205, Maitland

$397,000

Welcome to 2494 Castlewood Road, a spacious 4-bedroom, 2-bath pool home offering 2,086 square feet of potential on a large corner homesite in a quiet, tree-lined neighborhood. This property is ideal for investors or cash buyers looking for a renovation project in a desirable area with strong resale and rental potential. The home’s major systems have been recently updated, including: Solar Panels (2021); Roof (2021) with updated gutters, fascia, and soffits; HVAC System (2020); Water Heater (2020). A Four Point inspection was performed to ensure these new items are in great working order! The interior is ready for renovation, allowing you to create the perfect modern home or flip. The large pool needs some tlc, but offers great potential for the backyard. Enjoy a prime location near desirable English Estates Elementary (just a half-mile walk) and easy access to Oxford Road — an area currently seeing major investment and redevelopment by Seminole County. The neighborhood features sidewalk-lined streets, mature trees, and no required HOA fees, plus affordable taxes from no city property taxes, as the property is located in unincorporated Seminole County. Whether you’re looking for your next fix-and-flip or a long-term income property, this Maitland gem offers all the right ingredients: location, size, and built-in equity potential.

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

Welcome to 2494 Castlewood Road, a spacious 4-bedroom, 2-bath pool home offering 2,086 square feet of potential on a large corner homesite in a quiet, tree-lined neighborhood. This property is ideal for investors or cash buyers looking for a renovation project in a desirable area with strong resale and rental potential. The home’s major systems have been recently updated, including: Solar Panels (2021); Roof (2021) with updated gutters, fascia, and soffits; HVAC System (2020); Water Heater (2020). A Four Point inspection was performed to ensure these new items are in great working order! The interior is ready for renovation, allowing you to create the perfect modern home or flip. The large pool needs some tlc, but offers great potential for the backyard. Enjoy a prime location near desirable English Estates Elementary (just a half-mile walk) and easy access to Oxford Road — an area currently seeing major investment and redevelopment by Seminole County. The neighborhood features sidewalk-lined streets, mature trees, and no required HOA fees, plus affordable taxes from no city property taxes, as the property is located in unincorporated Seminole County. Whether you’re looking for your next fix-and-flip or a long-term income property, this Maitland gem offers all the right ingredients: location, size, and built-in equity potential.

2494 Castlewood Road, Maitland

$850,000

Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island, the heart of a kitchen designed for entertaining and everyday luxury. The GE Monogram and Café appliance suite, paired with custom solid wood, soft-close cabinetry, makes every detail feel bespoke. Natural light fills the living spaces through PGT double-pane insulated windows and Andersen French doors, framing tranquil garden views that create a sense of calm and privacy. Upstairs, two spacious bedroom suites offer comfort and style, each crafted with high-end finishes and thoughtful touches throughout. Beyond the walls, enjoy the rare privilege of a dedicated boat slip on Lake Maitland, Winter Park’s largest and sought-after body of water. Cruise the connected lakes, explore the historic canals or simply unwind at sunset, all just near home. Built in 1985 and completely transformed with modern systems, including a 2023 HVAC and water heater, this residence offers peace of mind to match its beauty. A one-car garage adds convenience, while every finish reflects care, quality and craftsmanship. Here, luxury isn’t just found inside, it’s a way of life, lived by the water.

2 Beds ⋅ 3 Baths ⋅ Moorings On Lake Maitland Condo Bldg 05 SubDv. ⋅ 32751 Zip Code

Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island, the heart of a kitchen designed for entertaining and everyday luxury. The GE Monogram and Café appliance suite, paired with custom solid wood, soft-close cabinetry, makes every detail feel bespoke. Natural light fills the living spaces through PGT double-pane insulated windows and Andersen French doors, framing tranquil garden views that create a sense of calm and privacy. Upstairs, two spacious bedroom suites offer comfort and style, each crafted with high-end finishes and thoughtful touches throughout. Beyond the walls, enjoy the rare privilege of a dedicated boat slip on Lake Maitland, Winter Park’s largest and sought-after body of water. Cruise the connected lakes, explore the historic canals or simply unwind at sunset, all just near home. Built in 1985 and completely transformed with modern systems, including a 2023 HVAC and water heater, this residence offers peace of mind to match its beauty. A one-car garage adds convenience, while every finish reflects care, quality and craftsmanship. Here, luxury isn’t just found inside, it’s a way of life, lived by the water.

219 Quayside Circle, Maitland

$775,000

Sought-after Dommerich Hills POOL Home with no HOA! This spacious block-construction residence sits on an oversized lot—over a quarter acre—and offers nearly 3,000 square feet of living space with a rare dual-primary-suite floor plan. The first primary suite is conveniently located on the main level, featuring a private en-suite bath with French doors that open directly to the pool. Upstairs, the second primary suite creates a true retreat with a huge oversized bedroom, walk-in closet, additional closet, custom built-ins, and recently updated bathroom. The large kitchen offers abundant cabinet space, granite counters and a double oven—perfect for holiday cooking and entertaining. Other highlights include a formal dining room, separate family room, and a generous living room with built-ins, fireplace and French doors that lead to the pool and very large private backyard. Fully fenced yard is perfect for pets, or you could building an outdoor kitchen and entertainment area, lots of possibilities. Roof 2021, fresh exterior paint (October 2025), and tons of storage space throughout the home. Large indoor laundry room with tons of cabinetry with new flooring. 2 car garage. The home is equipped with a Ring security system covering the front door, driveway, and backyard. Located in one of Maitland’s most desirable neighborhoods—Dommerich Hills. Zoned for top-rated, A+ schools. Dommerich Elementary, Maitland Middle and Winter Park High. Home is surrounded by multiple parks, including one just minutes away with basketball courts, playground, and picnic area. This is the lifestyle everyone wants!

4 Beds ⋅ 3 Baths ⋅ Dommerich Hills Fifth Add SubDv. ⋅ 32751 Zip Code

Sought-after Dommerich Hills POOL Home with no HOA! This spacious block-construction residence sits on an oversized lot—over a quarter acre—and offers nearly 3,000 square feet of living space with a rare dual-primary-suite floor plan. The first primary suite is conveniently located on the main level, featuring a private en-suite bath with French doors that open directly to the pool. Upstairs, the second primary suite creates a true retreat with a huge oversized bedroom, walk-in closet, additional closet, custom built-ins, and recently updated bathroom. The large kitchen offers abundant cabinet space, granite counters and a double oven—perfect for holiday cooking and entertaining. Other highlights include a formal dining room, separate family room, and a generous living room with built-ins, fireplace and French doors that lead to the pool and very large private backyard. Fully fenced yard is perfect for pets, or you could building an outdoor kitchen and entertainment area, lots of possibilities. Roof 2021, fresh exterior paint (October 2025), and tons of storage space throughout the home. Large indoor laundry room with tons of cabinetry with new flooring. 2 car garage. The home is equipped with a Ring security system covering the front door, driveway, and backyard. Located in one of Maitland’s most desirable neighborhoods—Dommerich Hills. Zoned for top-rated, A+ schools. Dommerich Elementary, Maitland Middle and Winter Park High. Home is surrounded by multiple parks, including one just minutes away with basketball courts, playground, and picnic area. This is the lifestyle everyone wants!

2550 Big Bend Trail, Maitland

$221,000

Incredible location! This beautifully updated 2 bedroom, 1.5 bath condo in Maitland is located minutes from shops, restaurants and offers easy access to I-4!. New windows! New electrical panels 2026, New water heater 2026. The stylish kitchen features granite countertops, 42 inch cabinetry, built-in wine glass rack, stainless appliances, pass thru window, and a long breakfast bar. Updated half bath downstairs for convenience. Both spacious bedrooms are located upstairs and share an updated bath with a glass enclosed tiled shower with rain shower fixtures. Laminate wood and tile flooring throughout! No carpet! Indoor laundry room with lots of storage with Maytag appliances. French doors lead you to a private fenced patio and one car garage! Step right outside the front door to the sparkling pool! Security system included. Zoned for sought-after schools, Dommerich Elementary, Maitland Middle, and Winter Park High. The neighborhood features a community pool, dock on Lake Gem and gorgeous landscaping and trees.

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

Incredible location! This beautifully updated 2 bedroom, 1.5 bath condo in Maitland is located minutes from shops, restaurants and offers easy access to I-4!. New windows! New electrical panels 2026, New water heater 2026. The stylish kitchen features granite countertops, 42 inch cabinetry, built-in wine glass rack, stainless appliances, pass thru window, and a long breakfast bar. Updated half bath downstairs for convenience. Both spacious bedrooms are located upstairs and share an updated bath with a glass enclosed tiled shower with rain shower fixtures. Laminate wood and tile flooring throughout! No carpet! Indoor laundry room with lots of storage with Maytag appliances. French doors lead you to a private fenced patio and one car garage! Step right outside the front door to the sparkling pool! Security system included. Zoned for sought-after schools, Dommerich Elementary, Maitland Middle, and Winter Park High. The neighborhood features a community pool, dock on Lake Gem and gorgeous landscaping and trees.

1009 Grove St Unit 1009, Maitland

$549,000

Under contract-accepting backup offers. HUGE PRICE DROP! Whole Duplex. 6/4 (3 bed 2 bath in each unit). The Duplex is located in a cul-de-sac on a large lot that backs up to walking trail. Oakmont neighborhood has access directly to Sunrail Maitland Station. No HOA. Unit 933 has a fireplace for those cold Florida winters. The backyard is fully fenced and has an above-the-ground pool and a fully functionable bar with electric and running water. Great Investment Opportunity! Reroofed in 2018. FREE 1-0 Temporary Buydown Rate (receive a 1% lower rate for 12 months) through the seller's preferred lender. Ask your agent for more info!! Offer expires June 30th.

6 Beds ⋅ 4 Baths ⋅ Oakwood SubDv. ⋅ 32751 Zip Code

Under contract-accepting backup offers. HUGE PRICE DROP! Whole Duplex. 6/4 (3 bed 2 bath in each unit). The Duplex is located in a cul-de-sac on a large lot that backs up to walking trail. Oakmont neighborhood has access directly to Sunrail Maitland Station. No HOA. Unit 933 has a fireplace for those cold Florida winters. The backyard is fully fenced and has an above-the-ground pool and a fully functionable bar with electric and running water. Great Investment Opportunity! Reroofed in 2018. FREE 1-0 Temporary Buydown Rate (receive a 1% lower rate for 12 months) through the seller's preferred lender. Ask your agent for more info!! Offer expires June 30th.

933 and 935 Robinhood Court, Maitland

$613,000

Elegant lakefront on the shores of Lake Maitland! Experience timeless refinement in this exquisitely renovated lakefront condominium, where bespoke craftmanship meets modern luxury. Every detail has been thoughtfully curated - from the custom millworker and intricate moldings to the tailored built-ins that evoke charm of a grand London flat. Light filled living spaces open to serene lake views, creating an atmosphere of both grace and tranquility. The gourmet kitchen is a study in elegance and function, featuring hand finished cabinetry, premium appliances, and stone surfaces. Gracious living room flows seamlessly into a charming sunroom, featuring French doors and classic brick flooring. The primary suite offers a peaceful, retreat with lake views, spa-inspired finishes and impeccable attention to detail. With rich textures, layered lighting, and designer finishes throughout, this home balances sophistication and warmth in perfect measure. Located in an exclusive building with exceptional amenities including pool, spa, clubhouse, a BOAT SLIP and 1 covered carport space. This residence embodies elevated lakefront living, with distinctive character. Call today for your private viewing of this exquisite condo. Please note there is a $640 transfer fee for boat slip paid at closing by Buyer.

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

Elegant lakefront on the shores of Lake Maitland! Experience timeless refinement in this exquisitely renovated lakefront condominium, where bespoke craftmanship meets modern luxury. Every detail has been thoughtfully curated - from the custom millworker and intricate moldings to the tailored built-ins that evoke charm of a grand London flat. Light filled living spaces open to serene lake views, creating an atmosphere of both grace and tranquility. The gourmet kitchen is a study in elegance and function, featuring hand finished cabinetry, premium appliances, and stone surfaces. Gracious living room flows seamlessly into a charming sunroom, featuring French doors and classic brick flooring. The primary suite offers a peaceful, retreat with lake views, spa-inspired finishes and impeccable attention to detail. With rich textures, layered lighting, and designer finishes throughout, this home balances sophistication and warmth in perfect measure. Located in an exclusive building with exceptional amenities including pool, spa, clubhouse, a BOAT SLIP and 1 covered carport space. This residence embodies elevated lakefront living, with distinctive character. Call today for your private viewing of this exquisite condo. Please note there is a $640 transfer fee for boat slip paid at closing by Buyer.

204 Quayside Circle Unit 202, Maitland

$335,000

Price improved! CONDO WITH PRIVATE GARAGE - JUST REPLUMBED WITH WARRANTY! Discover the perfect blend of comfort, elegance, and convenience in this beautifully updated 2-bedroom, 2-bath condominium in the highly sought-after Sierra Condominiums of Maitland. This move-in ready condo welcomes you with a screened front porch and an inviting living room with a wood-burning fireplace with an electric insert. The bonus room can be used as a television room, as a Florida room (offering a sunny spot to enjoy morning coffee while watching butterflies in the garden), or as a hobby room; leaving the living room free for formal entertaining. The upgraded kitchen features quartz countertops, under-cabinet lighting, new appliances, and accessible cupboards for easy access. A versatile breakfast nook (which is currently used as an office), includes a beautiful built-in cabinet perfect for dishes, collectibles or files. Tile floors in the kitchen and baths complement attractive laminate flooring throughout the living areas. Double-pane windows with plantation shutters, a new front door, gas heat, and a gas water heater provide comfort and efficiency year-round. Surrounded by mature trees and lush landscaping, this friendly, walkable neighborhood (with no traffic going through it), offers a warm community feel. Sierra residents enjoy a sparkling pool, tennis/pickleball court, and a welcoming clubhouse. HOA fees cover exterior maintenance, reserves for roofs, painting, roadway and pool upkeep, lawn care and cable television. A wonderful opportunity for those looking to downsize while maintaining an independent lifestyle – or an ideal first home with a coveted Maitland location!

2 Beds ⋅ 2 Baths ⋅ Sierra Condominiums SubDv. ⋅ 32751 Zip Code

Price improved! CONDO WITH PRIVATE GARAGE - JUST REPLUMBED WITH WARRANTY! Discover the perfect blend of comfort, elegance, and convenience in this beautifully updated 2-bedroom, 2-bath condominium in the highly sought-after Sierra Condominiums of Maitland. This move-in ready condo welcomes you with a screened front porch and an inviting living room with a wood-burning fireplace with an electric insert. The bonus room can be used as a television room, as a Florida room (offering a sunny spot to enjoy morning coffee while watching butterflies in the garden), or as a hobby room; leaving the living room free for formal entertaining. The upgraded kitchen features quartz countertops, under-cabinet lighting, new appliances, and accessible cupboards for easy access. A versatile breakfast nook (which is currently used as an office), includes a beautiful built-in cabinet perfect for dishes, collectibles or files. Tile floors in the kitchen and baths complement attractive laminate flooring throughout the living areas. Double-pane windows with plantation shutters, a new front door, gas heat, and a gas water heater provide comfort and efficiency year-round. Surrounded by mature trees and lush landscaping, this friendly, walkable neighborhood (with no traffic going through it), offers a warm community feel. Sierra residents enjoy a sparkling pool, tennis/pickleball court, and a welcoming clubhouse. HOA fees cover exterior maintenance, reserves for roofs, painting, roadway and pool upkeep, lawn care and cable television. A wonderful opportunity for those looking to downsize while maintaining an independent lifestyle – or an ideal first home with a coveted Maitland location!

2344 Sierra Lane, Maitland

$228,000

One or more photo(s) has been virtually staged. **2024 ROOF, 2025 HVAC** FULLY RENOVATED TOP TO BOTTOM. Discover this stunning, newly renovated one story end unit boasting over 1,000 sq ft of modern living space. This spacious 2 bedroom, 2 bath condo features luxury vinyl plank flooring throughout, a stylish new kitchen with white shaker cabinets, quartz countertops, and stainless steel appliances, plus all new light fixtures and fresh interior and exterior paint. Both bathrooms have been tastefully updated, including a stand up shower with designer finishes. Additional upgrades include a newer water heater, 2024 exterior paint, new attic insulation and more. Enjoy outdoor living on the private fenced patio, perfect for relaxing or entertaining. With the HOA maintaining the exterior, roof, and landscaping, you’ll enjoy truly worry free living. Conveniently located just steps from the community pool and minutes from shopping, dining, the Maitland Farmers Market, SunRail, Park Avenue, Winter Park Village, and I4. Schedule your showing today!

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

One or more photo(s) has been virtually staged. **2024 ROOF, 2025 HVAC** FULLY RENOVATED TOP TO BOTTOM. Discover this stunning, newly renovated one story end unit boasting over 1,000 sq ft of modern living space. This spacious 2 bedroom, 2 bath condo features luxury vinyl plank flooring throughout, a stylish new kitchen with white shaker cabinets, quartz countertops, and stainless steel appliances, plus all new light fixtures and fresh interior and exterior paint. Both bathrooms have been tastefully updated, including a stand up shower with designer finishes. Additional upgrades include a newer water heater, 2024 exterior paint, new attic insulation and more. Enjoy outdoor living on the private fenced patio, perfect for relaxing or entertaining. With the HOA maintaining the exterior, roof, and landscaping, you’ll enjoy truly worry free living. Conveniently located just steps from the community pool and minutes from shopping, dining, the Maitland Farmers Market, SunRail, Park Avenue, Winter Park Village, and I4. Schedule your showing today!

1601 Grove Street Unit 552, Maitland

$770,000

In the Heart of Maitland Winter Park boundary ~ 0.36 Acre Pool Home ~ 4200 Square Foot ~ 4 Bedrooms ~ 5 Bathrooms ~ Pool Home **For those with vision!** This rare opportunity in Maitland’s coveted Oakleigh neighborhood offers the ideal canvas for renovation or redesign. Surrounded by lakefront estates on an oversized lot, this expansive 4,200 sq ft traditional ranch sits on over one-third of an acre and is filled with natural light. The great room overlooks a private outdoor oasis with a pool, mature landscaping, and a brick-paved patio—perfect for entertaining. The chef’s kitchen features a commercial gas range, double ovens, built-in refrigerator, and a cozy dinette with a wood-burning fireplace—ready for your modern touch. A flexible double-primary split floor plan includes 4 bedrooms, 5 baths, and multiple living spaces, offering endless potential for customization. The primary suite showcases wood beams, hardwood floors, and a sitting area with pool views. The spacious en-suite includes dual showers, walk-in closets, and a skylit garden tub awaiting your personal style. Just minutes from Downtown Maitland, Minnehaha Park, and Lake Maitland, with easy I-4 access, this property offers both prime location and unmatched potential. Whether you’re an investor, designer, or homeowner ready to create your dream home, **51 Oakleigh Lane** is ready to become a masterpiece.

4 Beds ⋅ 5 Baths ⋅ Oakleigh 3rd Add SubDv. ⋅ 32751 Zip Code

In the Heart of Maitland Winter Park boundary ~ 0.36 Acre Pool Home ~ 4200 Square Foot ~ 4 Bedrooms ~ 5 Bathrooms ~ Pool Home **For those with vision!** This rare opportunity in Maitland’s coveted Oakleigh neighborhood offers the ideal canvas for renovation or redesign. Surrounded by lakefront estates on an oversized lot, this expansive 4,200 sq ft traditional ranch sits on over one-third of an acre and is filled with natural light. The great room overlooks a private outdoor oasis with a pool, mature landscaping, and a brick-paved patio—perfect for entertaining. The chef’s kitchen features a commercial gas range, double ovens, built-in refrigerator, and a cozy dinette with a wood-burning fireplace—ready for your modern touch. A flexible double-primary split floor plan includes 4 bedrooms, 5 baths, and multiple living spaces, offering endless potential for customization. The primary suite showcases wood beams, hardwood floors, and a sitting area with pool views. The spacious en-suite includes dual showers, walk-in closets, and a skylit garden tub awaiting your personal style. Just minutes from Downtown Maitland, Minnehaha Park, and Lake Maitland, with easy I-4 access, this property offers both prime location and unmatched potential. Whether you’re an investor, designer, or homeowner ready to create your dream home, **51 Oakleigh Lane** is ready to become a masterpiece.

51 Oakleigh Lane, Maitland

$575,000

Experience refined living in this impeccably maintained 4Bd/2Ba pool home with a spacious layout, perfectly situated in a desirable, well-established neighborhood close to shopping, dining and everyday essentials. The customized kitchen is a true showpiece—featuring an expansive pull-out pantry, double pull-out corner cabinet system, built-in spice rack, and a spacious island designed for both function and elegance. Abundant natural light, updated flush mount lighting, and ample storage create a space that is as beautiful as it is practical. Throughout the home, you’ll find timeless finishes including crown molding, wood-look porcelain tile, and double-pane windows that enhance both style and comfort. Step outside to your private oasis—an extra-large refinished pool (2017) surrounded by premier artificial turf and lush landscaping offering the perfect balance of luxury and low maintenance. The oversized garage impresses with extra shelving, an insulated door with DC quiet opener and battery backup, and the refrigerator is included. Peace of mind comes with thoughtful updates: Roof (2021), HVAC (2016), and new ductwork, R30 insulation and aluminum soffits (2024). A home where craftsmanship meets comfort—modern sophistication and meticulous care make this a rare opportunity not to be missed. CALL TODAY to schedule your private viewing.

4 Beds ⋅ 2 Baths ⋅ Forest Brook 3rd Sec SubDv. ⋅ 32751 Zip Code

Experience refined living in this impeccably maintained 4Bd/2Ba pool home with a spacious layout, perfectly situated in a desirable, well-established neighborhood close to shopping, dining and everyday essentials. The customized kitchen is a true showpiece—featuring an expansive pull-out pantry, double pull-out corner cabinet system, built-in spice rack, and a spacious island designed for both function and elegance. Abundant natural light, updated flush mount lighting, and ample storage create a space that is as beautiful as it is practical. Throughout the home, you’ll find timeless finishes including crown molding, wood-look porcelain tile, and double-pane windows that enhance both style and comfort. Step outside to your private oasis—an extra-large refinished pool (2017) surrounded by premier artificial turf and lush landscaping offering the perfect balance of luxury and low maintenance. The oversized garage impresses with extra shelving, an insulated door with DC quiet opener and battery backup, and the refrigerator is included. Peace of mind comes with thoughtful updates: Roof (2021), HVAC (2016), and new ductwork, R30 insulation and aluminum soffits (2024). A home where craftsmanship meets comfort—modern sophistication and meticulous care make this a rare opportunity not to be missed. CALL TODAY to schedule your private viewing.

671 Brookside Road, Maitland

$571,430

RENOVATIONS OF THE HIGHEST STANDARD!! Sunshine State Home’s experienced design team continues to exceed the expectations of today’s discerning Buyer’s. The renovation of this classic Mid-Century Maitland home brings delightful charm within a highly sought after NON-HOA neighborhood of Indian Hills. The finished product “punches above it’s weight” in every possible way. KITCHEN offers two-tone, solid wood cabinetry topped with contemporary quartz counters. Stylish finishes including an undermount sink with long-neck faucet, upgraded black-matte cabinet door pulls and a modern stainless steel appliance package create a delightful cooking environment. LARGE LIVING SPACES including living / bonus / dinette and separate family rooms offer an abundance of options catering to a variety of lifestyle preferences and activities. BEDROOMS within this split-plan layout include His/Hers closets in the primary suite and a large 2nd bedroom and 3rd bedroom situated privately in the far corner of home. FLOORING throughout the home, upgraded Luxury Vinyl Plank was laid “wall-to-wall” and topped with upgraded 5 ¼“ baseboards, creating a peaceful yet contemporary feel to every room. BATHROOMS (both primary and secondary) have been fully remodeled including sinks, faucets, shower, tub, toilets, lighting and more. FINISHES including modern door hardware & hinges, ceiling fan and LED lighting throughout, wire rack shelving in all closets, updated electrical outlets and switches all combine to bring this vintage home up to today’s look & feel. OUTSIDE, a covered area on the back patio lanai provides the perfect shaded gathering place amidst a sun-filled day splashing in the inground swimming pool. Fully fenced and private, the backyard offers an oasis for sunbathing and a midnight swim. 4-POINT inspection items including roof (2023), hot-water heater (2025), HVAC (2019) will provide peace of mind. COMMUNITY events and activities abound within Indian Hills. Kewannee Park, a county park, offers walking trails and a boardwalk, fishing ponds, basketball court, and playgrounds all within walking distance. A-Rated Seminole County Public School district.

3 Beds ⋅ 2 Baths ⋅ Indian Hills Unit 9 SubDv. ⋅ 32751 Zip Code

RENOVATIONS OF THE HIGHEST STANDARD!! Sunshine State Home’s experienced design team continues to exceed the expectations of today’s discerning Buyer’s. The renovation of this classic Mid-Century Maitland home brings delightful charm within a highly sought after NON-HOA neighborhood of Indian Hills. The finished product “punches above it’s weight” in every possible way. KITCHEN offers two-tone, solid wood cabinetry topped with contemporary quartz counters. Stylish finishes including an undermount sink with long-neck faucet, upgraded black-matte cabinet door pulls and a modern stainless steel appliance package create a delightful cooking environment. LARGE LIVING SPACES including living / bonus / dinette and separate family rooms offer an abundance of options catering to a variety of lifestyle preferences and activities. BEDROOMS within this split-plan layout include His/Hers closets in the primary suite and a large 2nd bedroom and 3rd bedroom situated privately in the far corner of home. FLOORING throughout the home, upgraded Luxury Vinyl Plank was laid “wall-to-wall” and topped with upgraded 5 ¼“ baseboards, creating a peaceful yet contemporary feel to every room. BATHROOMS (both primary and secondary) have been fully remodeled including sinks, faucets, shower, tub, toilets, lighting and more. FINISHES including modern door hardware & hinges, ceiling fan and LED lighting throughout, wire rack shelving in all closets, updated electrical outlets and switches all combine to bring this vintage home up to today’s look & feel. OUTSIDE, a covered area on the back patio lanai provides the perfect shaded gathering place amidst a sun-filled day splashing in the inground swimming pool. Fully fenced and private, the backyard offers an oasis for sunbathing and a midnight swim. 4-POINT inspection items including roof (2023), hot-water heater (2025), HVAC (2019) will provide peace of mind. COMMUNITY events and activities abound within Indian Hills. Kewannee Park, a county park, offers walking trails and a boardwalk, fishing ponds, basketball court, and playgrounds all within walking distance. A-Rated Seminole County Public School district.

2666 Derbyshire Road, Maitland

$779,500

Welcome to this charming, move-in ready home nestled in the desirable, family-friendly Dommerich neighborhood. Featuring 3 bedrooms, 2 full bathrooms, and an open-concept living area filled with natural light, this home has the perfect blend of comfort and style. Featuring 2 additional dedicated office rooms, ideal for remote work or creative space, this home is ideal for modern living. The updated kitchen boasts stainless steel appliances, marble countertops, and ample cabinet space. Step into an open, light-filled interior with brand new flooring throughout and breathtaking floor-to-ceiling windows that has panoramic views of the sparkling saltwater pool. In the cooler months enjoy your own wood burning fireplace. Outside, enjoy a spacious paver driveway, a large 2-car garage, and a private backyard oasis. Major upgrades include a brand new roof (2025), ensuring peace of mind for years to come. Additional upgrades include recessed lighting, new flooring throughout, marble bathroom tiling, energy-efficient windows, new paver driveway and fresh interior/exterior paint. Enjoy private boat ramp access to the Winter Park Chain of Lakes. Zoned for A-rated Dommerich Elementary, Maitland Middle School and Winter Park High School. Walking distance to the Maitland Community Park, Maitland Social and the Maitland City Center. Minutes from Winter Park’s Park Avenue, known for its exquisite shopping and dining. Don’t miss out on this opportunity!

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

Welcome to this charming, move-in ready home nestled in the desirable, family-friendly Dommerich neighborhood. Featuring 3 bedrooms, 2 full bathrooms, and an open-concept living area filled with natural light, this home has the perfect blend of comfort and style. Featuring 2 additional dedicated office rooms, ideal for remote work or creative space, this home is ideal for modern living. The updated kitchen boasts stainless steel appliances, marble countertops, and ample cabinet space. Step into an open, light-filled interior with brand new flooring throughout and breathtaking floor-to-ceiling windows that has panoramic views of the sparkling saltwater pool. In the cooler months enjoy your own wood burning fireplace. Outside, enjoy a spacious paver driveway, a large 2-car garage, and a private backyard oasis. Major upgrades include a brand new roof (2025), ensuring peace of mind for years to come. Additional upgrades include recessed lighting, new flooring throughout, marble bathroom tiling, energy-efficient windows, new paver driveway and fresh interior/exterior paint. Enjoy private boat ramp access to the Winter Park Chain of Lakes. Zoned for A-rated Dommerich Elementary, Maitland Middle School and Winter Park High School. Walking distance to the Maitland Community Park, Maitland Social and the Maitland City Center. Minutes from Winter Park’s Park Avenue, known for its exquisite shopping and dining. Don’t miss out on this opportunity!

421 Arapaho Trail, Maitland

$500,000

**2025 ROOF** | **POOL HOME** Start your new life to one of Orlando's most prestigious suburbs! Located in the heart of Maitland and zoned for great schools! This 4 bedroom, 2 bath home is a sanctuary for a growing family or to start yours. In this stunning home comfort meets timeless charm. Outside you will find a Zen-like screened pool area and a serene back yard lushly landscaped with mature fruit trees. Enjoy the benefits of a newly installed roof and upgraded insulation, providing energy efficiency and cost savings. This home offers the perfect blend of value and comfort, situated minutes from downtown Winter Park, downtown Orlando and just walking distance from Kewanee Park. Here you’ll enjoy proximity to upscale boutiques, cafés and fine dining, making this home convenient and comfortable for everyday living. This is a rare opportunity to own a meticulously maintained and perfectly situated home. Ready for you to move in and enjoy!

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

**2025 ROOF** | **POOL HOME** Start your new life to one of Orlando's most prestigious suburbs! Located in the heart of Maitland and zoned for great schools! This 4 bedroom, 2 bath home is a sanctuary for a growing family or to start yours. In this stunning home comfort meets timeless charm. Outside you will find a Zen-like screened pool area and a serene back yard lushly landscaped with mature fruit trees. Enjoy the benefits of a newly installed roof and upgraded insulation, providing energy efficiency and cost savings. This home offers the perfect blend of value and comfort, situated minutes from downtown Winter Park, downtown Orlando and just walking distance from Kewanee Park. Here you’ll enjoy proximity to upscale boutiques, cafés and fine dining, making this home convenient and comfortable for everyday living. This is a rare opportunity to own a meticulously maintained and perfectly situated home. Ready for you to move in and enjoy!

2632 Derbyshire Road, Maitland

$970,000

Sold data entry only

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

Sold data entry only

2031 Chippewa Trail, Maitland

$400,000

Breathtaking views of Lake Maitland, the largest lake of the desirable Winter Park Chain of Lakes. Enjoy sunrises across the lake from the privacy of your balcony overlooking the pool. This 2-bedroom, 2-bath condo within West Cove Condos is centrally located in close proximity to a variety of restaurants, Lake Lily Park, Enzian Theater and easy access to I-4 and Maitland Blvd. Your association fees include access to the lakefront docks (boat slips assigned on availability basis and free of charge), work out room, lobby area for entertaining, heated swimming pool and spa, grilling area with sitting space, storage racks for canoes, kayaks and paddleboards, assigned and guest parking, laundry room on each floor, cable and internet through Spectrum, plus water, sewer and trash. Elevator has secured access to your floor.

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

Breathtaking views of Lake Maitland, the largest lake of the desirable Winter Park Chain of Lakes. Enjoy sunrises across the lake from the privacy of your balcony overlooking the pool. This 2-bedroom, 2-bath condo within West Cove Condos is centrally located in close proximity to a variety of restaurants, Lake Lily Park, Enzian Theater and easy access to I-4 and Maitland Blvd. Your association fees include access to the lakefront docks (boat slips assigned on availability basis and free of charge), work out room, lobby area for entertaining, heated swimming pool and spa, grilling area with sitting space, storage racks for canoes, kayaks and paddleboards, assigned and guest parking, laundry room on each floor, cable and internet through Spectrum, plus water, sewer and trash. Elevator has secured access to your floor.

1100 S Orlando Avenue Unit 208, Maitland

$365,000

Welcome to Montacino, a gated community offering both convenience and charm. This updated 3-bedroom, 2.5-bath townhome combines modern finishes with a comfortable, functional layout. The first floor features an open design with spacious living, dining, and kitchen areas that flow seamlessly for everyday living or entertaining. The kitchen includes granite countertops, stainless steel appliances, and a stylish backsplash, with views of the covered back porch overlooking a peaceful green space. A convenient half bath is also located downstairs. Upstairs, the primary suite offers a private balcony, walk-in closet, and en-suite bath with dual vanities and a walk-in shower. Two additional bedrooms, a full bathroom, and a conveniently located laundry closet with washer and dryer complete the second level. Recent updates include new laminate flooring downstairs, along with a new microwave and refrigerator. The home also includes a one-car garage. Residents enjoy truly maintenance-free living, with the HOA fee covering internet, cable TV, exterior pest/termite control, roof repair and/or replacement, and exterior upkeep, as well as access to a resort-style pool, beautifully landscaped grounds, and lakeside sidewalks perfect for a stroll. A transferable home warranty is also available for added peace of mind. Ideally located near I-4, Winter Park, and Downtown Orlando, this home offers the perfect balance of a peaceful retreat and city convenience.

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

Welcome to Montacino, a gated community offering both convenience and charm. This updated 3-bedroom, 2.5-bath townhome combines modern finishes with a comfortable, functional layout. The first floor features an open design with spacious living, dining, and kitchen areas that flow seamlessly for everyday living or entertaining. The kitchen includes granite countertops, stainless steel appliances, and a stylish backsplash, with views of the covered back porch overlooking a peaceful green space. A convenient half bath is also located downstairs. Upstairs, the primary suite offers a private balcony, walk-in closet, and en-suite bath with dual vanities and a walk-in shower. Two additional bedrooms, a full bathroom, and a conveniently located laundry closet with washer and dryer complete the second level. Recent updates include new laminate flooring downstairs, along with a new microwave and refrigerator. The home also includes a one-car garage. Residents enjoy truly maintenance-free living, with the HOA fee covering internet, cable TV, exterior pest/termite control, roof repair and/or replacement, and exterior upkeep, as well as access to a resort-style pool, beautifully landscaped grounds, and lakeside sidewalks perfect for a stroll. A transferable home warranty is also available for added peace of mind. Ideally located near I-4, Winter Park, and Downtown Orlando, this home offers the perfect balance of a peaceful retreat and city convenience.

1291 Blessing Street, Maitland

$545,000

Discover the perfect blend of style and location in this beautifully updated 3-bedroom, 2.5-bathroom townhome in the sought-after Moorings community. With 1,734 square feet of thoughtfully designed living space, this residence offers a bright, open floor plan enhanced by vaulted ceilings and an abundance of natural light. The heart of the home is the stunning kitchen, showcasing white cabinetry, quartz countertops, stainless steel appliances, a decorative hood above the cooktop, and a classic subway tile backsplash. A charming bay window creates the perfect breakfast nook, while the open-concept living and dining areas provide ideal space for entertaining and everyday living. A wood-burning fireplace adds warmth and ambiance to the living room, creating a cozy focal point. Step through French doors into a sun-drenched sunroom with walls of windows overlooking tranquil community green space – your own private retreat for morning coffee or evening relaxation. Luxury vinyl plank flooring flows throughout the main level, complemented by plantation shutters and fresh paint. The second floor houses all three generously sized bedrooms, including a serene primary suite with a completely renovated en suite bathroom featuring a double sink vanity, walk-in shower, and spacious walk-in closet with custom built-ins. The updated hall bath offers a tub/shower combo and single-sink vanity. The second bedroom also features custom built-in closet organizers for added storage and convenience. Additional features include ceiling fans, interior laundry, and an attached one-car garage. Living in The Moorings means enjoying exclusive amenities, including a community dock on Lake Maitland, sparkling pool, and clubhouse. The location is unbeatable – just moments from Maitland's charming Lake Lily Park and its popular weekly farmer's market, five minutes from the upscale shops and dining of Park Avenue, and surrounded by the best of Central Florida's shopping, restaurants, and entertainment.

3 Beds ⋅ 3 Baths ⋅ Moorings On Lake Maitland Condo Bldg 05 SubDv. ⋅ 32751 Zip Code

Discover the perfect blend of style and location in this beautifully updated 3-bedroom, 2.5-bathroom townhome in the sought-after Moorings community. With 1,734 square feet of thoughtfully designed living space, this residence offers a bright, open floor plan enhanced by vaulted ceilings and an abundance of natural light. The heart of the home is the stunning kitchen, showcasing white cabinetry, quartz countertops, stainless steel appliances, a decorative hood above the cooktop, and a classic subway tile backsplash. A charming bay window creates the perfect breakfast nook, while the open-concept living and dining areas provide ideal space for entertaining and everyday living. A wood-burning fireplace adds warmth and ambiance to the living room, creating a cozy focal point. Step through French doors into a sun-drenched sunroom with walls of windows overlooking tranquil community green space – your own private retreat for morning coffee or evening relaxation. Luxury vinyl plank flooring flows throughout the main level, complemented by plantation shutters and fresh paint. The second floor houses all three generously sized bedrooms, including a serene primary suite with a completely renovated en suite bathroom featuring a double sink vanity, walk-in shower, and spacious walk-in closet with custom built-ins. The updated hall bath offers a tub/shower combo and single-sink vanity. The second bedroom also features custom built-in closet organizers for added storage and convenience. Additional features include ceiling fans, interior laundry, and an attached one-car garage. Living in The Moorings means enjoying exclusive amenities, including a community dock on Lake Maitland, sparkling pool, and clubhouse. The location is unbeatable – just moments from Maitland's charming Lake Lily Park and its popular weekly farmer's market, five minutes from the upscale shops and dining of Park Avenue, and surrounded by the best of Central Florida's shopping, restaurants, and entertainment.

225 Quayside Circle, Maitland

$375,000

Stunning, renovated condo in Maitland’s Ultra Vista community with attached one-car garage. Expect to be impressed as you enter this luxury residence boasting vaulted ceilings which fill the home with natural light! Fall in love with this remodeled kitchen with a butcher block island, 42-inch white cabinetry, soft-close drawers, pantry, tile flooring, and stainless-steel appliances. Wonderful great room with wood-burning fireplace, dining room, and sliding doors leading to the enclosed outdoor porch, perfect for entertaining! Gorgeous wood flooring brings warmth to the home. Retreat to the primary suite with an impressive, updated bath featuring stone counters, walk-in closet, and spacious walk-in shower. The 2nd bedroom is bright and spacious with an updated en-suite bath with soaking tub. The downstairs bedroom with updated en-suite bath is perfectly positioned for a guest suite, home office or den. Enjoy the privacy outdoors with the stone patio and beautiful landscaping overlooking a conservation area. Updates include a new roof (2024), new electrical panel (2024), replumbed, AC (2016) and new exterior paint coming soon. This private community offers a sparkling swimming pool and dog park for its residence. Incredible location, minutes to Winter Park’s Park Ave for shopping and dining. This is the one you have been waiting for!

3 Beds ⋅ 3 Baths ⋅ Ultra Vista Condo SubDv. ⋅ 32751 Zip Code

Stunning, renovated condo in Maitland’s Ultra Vista community with attached one-car garage. Expect to be impressed as you enter this luxury residence boasting vaulted ceilings which fill the home with natural light! Fall in love with this remodeled kitchen with a butcher block island, 42-inch white cabinetry, soft-close drawers, pantry, tile flooring, and stainless-steel appliances. Wonderful great room with wood-burning fireplace, dining room, and sliding doors leading to the enclosed outdoor porch, perfect for entertaining! Gorgeous wood flooring brings warmth to the home. Retreat to the primary suite with an impressive, updated bath featuring stone counters, walk-in closet, and spacious walk-in shower. The 2nd bedroom is bright and spacious with an updated en-suite bath with soaking tub. The downstairs bedroom with updated en-suite bath is perfectly positioned for a guest suite, home office or den. Enjoy the privacy outdoors with the stone patio and beautiful landscaping overlooking a conservation area. Updates include a new roof (2024), new electrical panel (2024), replumbed, AC (2016) and new exterior paint coming soon. This private community offers a sparkling swimming pool and dog park for its residence. Incredible location, minutes to Winter Park’s Park Ave for shopping and dining. This is the one you have been waiting for!

1990 Kenaston Road Unit 1990, Maitland

$251,500

Live on Lake Maitland, part of the Winter Park Chain of Lakes, for just $250,000! This 2-bedroom, 1.5-bath condo in Lake Maitland Terrace is one of the most desirable units in the community, offering 816 square feet and a prime second-floor corner location with a screened-in front porch. Inside, you’ll find spacious living areas with bamboo flooring, plantation shutters, and abundant natural light. The porch extends your living space and is the perfect spot to quietly sip your morning coffee. Thoughtful upgrades set this home apart. The washer and dryer are conveniently located in the hallway, preserving closet space in both bedrooms. The primary bedroom features a true walk-in closet, and both bedrooms include custom closet systems that maximize storage and style. Opportunities to live on the Winter Park Chain of Lakes at this price point are incredibly rare. With its generous layout, upgraded features, and unbeatable location, this condo is a standout that won’t last long.

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

Live on Lake Maitland, part of the Winter Park Chain of Lakes, for just $250,000! This 2-bedroom, 1.5-bath condo in Lake Maitland Terrace is one of the most desirable units in the community, offering 816 square feet and a prime second-floor corner location with a screened-in front porch. Inside, you’ll find spacious living areas with bamboo flooring, plantation shutters, and abundant natural light. The porch extends your living space and is the perfect spot to quietly sip your morning coffee. Thoughtful upgrades set this home apart. The washer and dryer are conveniently located in the hallway, preserving closet space in both bedrooms. The primary bedroom features a true walk-in closet, and both bedrooms include custom closet systems that maximize storage and style. Opportunities to live on the Winter Park Chain of Lakes at this price point are incredibly rare. With its generous layout, upgraded features, and unbeatable location, this condo is a standout that won’t last long.

1140 S Orlando Avenue Unit F9, Maitland

$255,000

Step inside this beautifully reimagined Lake Maitland Terrace condo, where every detail has been thoughtfully updated for style and function. Renovated in 2021, this spacious one-bedroom residence embraces a modern design with clean lines, custom finishes, and a touch of industrial character from the exposed ceiling piping. The open layout features a bright great room that flows seamlessly into the kitchen, designed with both cooking and entertaining in mind. Highlights include Caesarstone quartz countertops, a mirrored backsplash, a farmhouse sink, KraftMaid soft-close cabinetry, and an oversized island with seating. Premium appliances such as a KitchenAid convection oven with induction cooktop, Bosch dishwasher, French-door refrigerator, and in-unit washer and dryer add convenience and sophistication. Originally configured as a two-bedroom, the condo has been transformed into a larger one-bedroom retreat but can easily be converted back if desired. The bathroom offers a tub/shower combination and an extra-wide pedestal sink. Enjoy a low-maintenance lifestyle with resort-style amenities, including a community pool, shuffleboard courts, fishing pier, and access to Lake Maitland and the Chain of Lakes. The unbeatable location puts you within walking distance of the Enzian Theater and Lake Lily, while Winter Park Village, Park Avenue, and A-rated schools are just minutes away.

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

Step inside this beautifully reimagined Lake Maitland Terrace condo, where every detail has been thoughtfully updated for style and function. Renovated in 2021, this spacious one-bedroom residence embraces a modern design with clean lines, custom finishes, and a touch of industrial character from the exposed ceiling piping. The open layout features a bright great room that flows seamlessly into the kitchen, designed with both cooking and entertaining in mind. Highlights include Caesarstone quartz countertops, a mirrored backsplash, a farmhouse sink, KraftMaid soft-close cabinetry, and an oversized island with seating. Premium appliances such as a KitchenAid convection oven with induction cooktop, Bosch dishwasher, French-door refrigerator, and in-unit washer and dryer add convenience and sophistication. Originally configured as a two-bedroom, the condo has been transformed into a larger one-bedroom retreat but can easily be converted back if desired. The bathroom offers a tub/shower combination and an extra-wide pedestal sink. Enjoy a low-maintenance lifestyle with resort-style amenities, including a community pool, shuffleboard courts, fishing pier, and access to Lake Maitland and the Chain of Lakes. The unbeatable location puts you within walking distance of the Enzian Theater and Lake Lily, while Winter Park Village, Park Avenue, and A-rated schools are just minutes away.

1140 S Orlando Avenue Unit J2, Maitland

$545,000

Seller is willing to assist with buyer closing costs or assist with interest rate buy down. This stunning 4-bedroom, 2-bathroom home has been completely reimagined from the ground up, offering flawless design, and premium finishes. Situated on a generous lot in a sought-after Maitland neighborhood, this home combines comfort, function, and style in every detail. Step inside to an inviting open-concept layout with luxury vinyl plank flooring, new lighting, and abundant natural light streaming through vinyl windows. The designer kitchen steals the spotlight with updates cabinetry, granite countertops with, and new appliances—crafted for the modern entertainer. The primary suite offers a tranquil retreat with a spa-inspired en suite bathroom featuring beautiful tilework and elegant fixtures. Both bathrooms have been tastefully renovated to reflect timeless design. Enjoy the added flexibility of a dedicated laundry room and a 2 car garage offering extra storage and workspace. Outside, the expansive backyard with a newly resurfaced in ground pool is your canvas for creating the outdoor lifestyle you've always wanted—whether it's hosting gatherings, gardening, or relaxing in the Florida sunshine. Located just minutes from top-rated schools, parks, shopping, and dining, 1470 Winston isn’t just move-in ready—it’s transformation perfected. Schedule your private showing today and fall in love with everything this exceptional home has to show. Clean 4 point inspection available by request.

4 Beds ⋅ 2 Baths ⋅ English Estates Unit 3 SubDv. ⋅ 32751 Zip Code

Seller is willing to assist with buyer closing costs or assist with interest rate buy down. This stunning 4-bedroom, 2-bathroom home has been completely reimagined from the ground up, offering flawless design, and premium finishes. Situated on a generous lot in a sought-after Maitland neighborhood, this home combines comfort, function, and style in every detail. Step inside to an inviting open-concept layout with luxury vinyl plank flooring, new lighting, and abundant natural light streaming through vinyl windows. The designer kitchen steals the spotlight with updates cabinetry, granite countertops with, and new appliances—crafted for the modern entertainer. The primary suite offers a tranquil retreat with a spa-inspired en suite bathroom featuring beautiful tilework and elegant fixtures. Both bathrooms have been tastefully renovated to reflect timeless design. Enjoy the added flexibility of a dedicated laundry room and a 2 car garage offering extra storage and workspace. Outside, the expansive backyard with a newly resurfaced in ground pool is your canvas for creating the outdoor lifestyle you've always wanted—whether it's hosting gatherings, gardening, or relaxing in the Florida sunshine. Located just minutes from top-rated schools, parks, shopping, and dining, 1470 Winston isn’t just move-in ready—it’s transformation perfected. Schedule your private showing today and fall in love with everything this exceptional home has to show. Clean 4 point inspection available by request.

1470 Winston Road, Maitland

$535,000

RARE OPPORTUNITY – Enjoy lakefront living with a PRIVATE BOAT SLIP on the Winter Park chain of lakes in this top-floor penthouse condo. The Moorings on Lake Maitland, one of Central Florida’s most coveted waterfront communities. This spacious 2-bedroom, 2-bath residence offers soaring vaulted ceilings, breathtaking lake views, and your own assigned private boat slip—a rare find on the Winter Park Chain of Lakes. Step inside to an abundance of natural light and a thoughtfully designed floor plan with no upstairs neighbors, ensuring maximum privacy and quiet. The large living area opens to a glass-enclosed sunroom with panoramic views of Lake Maitland—perfect for morning coffee or relaxing at sunset. The kitchen is bright and functional, featuring a breakfast nook and walk-in pantry. The split-bedroom layout offers privacy and flexibility. The primary suite includes a handicap-accessible bath, generous closet space, and tranquil lake views. The guest bedroom and full second bath are perfect for visitors or a home office. The laundry is conveniently located tucked off the main hall, and with custom closets in both bedrooms the amount of storage is great. For larger items the unit includes a locking storage closet on the landing, and is perfect for bikes, golf clubs, holiday decorations etc. The unit comes with one reserved covered parking space and plenty of guest parking. The complex has a newly renovated pool, hot tub & clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this rare top-floor condo offers an unbeatable combination of comfort, convenience, and waterfront access. Live the Florida lake lifestyle—schedule your private showing today!

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

RARE OPPORTUNITY – Enjoy lakefront living with a PRIVATE BOAT SLIP on the Winter Park chain of lakes in this top-floor penthouse condo. The Moorings on Lake Maitland, one of Central Florida’s most coveted waterfront communities. This spacious 2-bedroom, 2-bath residence offers soaring vaulted ceilings, breathtaking lake views, and your own assigned private boat slip—a rare find on the Winter Park Chain of Lakes. Step inside to an abundance of natural light and a thoughtfully designed floor plan with no upstairs neighbors, ensuring maximum privacy and quiet. The large living area opens to a glass-enclosed sunroom with panoramic views of Lake Maitland—perfect for morning coffee or relaxing at sunset. The kitchen is bright and functional, featuring a breakfast nook and walk-in pantry. The split-bedroom layout offers privacy and flexibility. The primary suite includes a handicap-accessible bath, generous closet space, and tranquil lake views. The guest bedroom and full second bath are perfect for visitors or a home office. The laundry is conveniently located tucked off the main hall, and with custom closets in both bedrooms the amount of storage is great. For larger items the unit includes a locking storage closet on the landing, and is perfect for bikes, golf clubs, holiday decorations etc. The unit comes with one reserved covered parking space and plenty of guest parking. The complex has a newly renovated pool, hot tub & clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this rare top-floor condo offers an unbeatable combination of comfort, convenience, and waterfront access. Live the Florida lake lifestyle—schedule your private showing today!

202 Quayside Circle Unit 404, Maitland

$475,000

Charming and Spacious Townhome in Maitland! Welcome to 1938 Michael Tiago a beautifully maintained 4-bedroom, 2.5 bathroom home located in the desirable Maitland Village Community with a POND VIEW and END UNIT. This stunning property offers a perfect blend of classic charm and modern convenience, making it an ideal place to call home. As you approach this inviting residence, you’ll notice the lush landscaping and curb appeal that instantly sets the tone for what’s inside. Step into the spacious living area, where natural light pours in through large windows, creating a warm and inviting atmosphere. The open-concept floor plan seamlessly flows into the dining area and kitchen, making this space perfect for both everyday living and entertaining guests. Crown molding enhances the rooms adding just that right touch! Custom Plantation Shutters adorn all the windows downstairs & upstairs. The kitchen is a chef's dream, featuring stainless steel appliances, granite countertops, and ample cabinet space for all your culinary needs. A walk in panty is another feature of the kitchen. Whether you're preparing a weeknight meal or hosting a dinner party, this kitchen will exceed your expectations. The primary suite is generously sized and offers a peaceful retreat, complete with a private en-suite bathroom featuring a dual vanity, soaking tub, and a separate walk-in shower. Two additional well-appointed bedrooms provide plenty of space for family. The fourth bedroom featuring French Doors is located downsttairs...it can also be used as an office if needed. The Loft upstairs is light & bright and would make a great office or home school area. The Tile Roof brings long lasting peace of mind. This is an End Unit which allows for more light to filter thru from outside. Hot Water Heater is new. New Stainless Steel Dishwasher & Disposal are being installed. HOA fees cover exterior maintenance, 500 Mbps internet, 250 channel cable, water, sewer, trash, lawn care, sprinklers, streetlights, community pool, clubhouse, gate access and management services. Your low HOA fee takes care of all the yard work so you can enjoy the Community Pool. This makes living here "totally carefree living at its best". Other highlights include tile & engineered wood flooring throughout downstairs, a covered porch with a pond view, no neighbor on one side and a 2-car garage that has 2-car EV-ready. Located just minutes from shopping, dining, and major roadways, this home offers the convenience of being close to everything while providing a quiet, serene neighborhood feel. Don't miss your chance to own this charming Maitland home. Schedule a showing today and make 1938 Michael Tioga your new address!

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

Charming and Spacious Townhome in Maitland! Welcome to 1938 Michael Tiago a beautifully maintained 4-bedroom, 2.5 bathroom home located in the desirable Maitland Village Community with a POND VIEW and END UNIT. This stunning property offers a perfect blend of classic charm and modern convenience, making it an ideal place to call home. As you approach this inviting residence, you’ll notice the lush landscaping and curb appeal that instantly sets the tone for what’s inside. Step into the spacious living area, where natural light pours in through large windows, creating a warm and inviting atmosphere. The open-concept floor plan seamlessly flows into the dining area and kitchen, making this space perfect for both everyday living and entertaining guests. Crown molding enhances the rooms adding just that right touch! Custom Plantation Shutters adorn all the windows downstairs & upstairs. The kitchen is a chef's dream, featuring stainless steel appliances, granite countertops, and ample cabinet space for all your culinary needs. A walk in panty is another feature of the kitchen. Whether you're preparing a weeknight meal or hosting a dinner party, this kitchen will exceed your expectations. The primary suite is generously sized and offers a peaceful retreat, complete with a private en-suite bathroom featuring a dual vanity, soaking tub, and a separate walk-in shower. Two additional well-appointed bedrooms provide plenty of space for family. The fourth bedroom featuring French Doors is located downsttairs...it can also be used as an office if needed. The Loft upstairs is light & bright and would make a great office or home school area. The Tile Roof brings long lasting peace of mind. This is an End Unit which allows for more light to filter thru from outside. Hot Water Heater is new. New Stainless Steel Dishwasher & Disposal are being installed. HOA fees cover exterior maintenance, 500 Mbps internet, 250 channel cable, water, sewer, trash, lawn care, sprinklers, streetlights, community pool, clubhouse, gate access and management services. Your low HOA fee takes care of all the yard work so you can enjoy the Community Pool. This makes living here "totally carefree living at its best". Other highlights include tile & engineered wood flooring throughout downstairs, a covered porch with a pond view, no neighbor on one side and a 2-car garage that has 2-car EV-ready. Located just minutes from shopping, dining, and major roadways, this home offers the convenience of being close to everything while providing a quiet, serene neighborhood feel. Don't miss your chance to own this charming Maitland home. Schedule a showing today and make 1938 Michael Tioga your new address!

1938 Michael Tiago Court, Maitland

$915,000

One-story home in Dommerich Hills within walking distance to Dommerich Elementary and Maitland Middle schools. Move-in ready with wonderful pool. Beautifully landscaped.

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

One-story home in Dommerich Hills within walking distance to Dommerich Elementary and Maitland Middle schools. Move-in ready with wonderful pool. Beautifully landscaped.

2021 Chippewa Trail, Maitland

$395,000

SELLER PAYING CONCESSIONS OF 6 MONTH HOA FEES. Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the Moorings on Lake Maitland. Enjoy relaxing on the Lake Front Dock or on your own Private Enclosed Patio! Step inside this spacious 2 bedroom 2 bath great room plan, perfect for relaxing or entertaining. The beautifully upgraded kitchen has stainless steel appliances and granite counters and a charming dining nook. The master suite features an updated ensuite bath with dual sinks and a walk in shower with a custom glass enclosure. There is a generous walk in closet with custom built ins. Imagine coffee in the morning with lake views from your living room or your spacious patio. Only 5 minute drive to Winter Park's shops & Sidewalk Dining along the famed Park Avenue. Stroll over to Maitland's lovely Lake Lilly Park for Seasonal Events, Art Festivals, Concerts and local Farmer's Market! Incredible Location & Lifestyle!!!!

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

SELLER PAYING CONCESSIONS OF 6 MONTH HOA FEES. Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the Moorings on Lake Maitland. Enjoy relaxing on the Lake Front Dock or on your own Private Enclosed Patio! Step inside this spacious 2 bedroom 2 bath great room plan, perfect for relaxing or entertaining. The beautifully upgraded kitchen has stainless steel appliances and granite counters and a charming dining nook. The master suite features an updated ensuite bath with dual sinks and a walk in shower with a custom glass enclosure. There is a generous walk in closet with custom built ins. Imagine coffee in the morning with lake views from your living room or your spacious patio. Only 5 minute drive to Winter Park's shops & Sidewalk Dining along the famed Park Avenue. Stroll over to Maitland's lovely Lake Lilly Park for Seasonal Events, Art Festivals, Concerts and local Farmer's Market! Incredible Location & Lifestyle!!!!

204 Quayside Circle Unit 304, Maitland

$178,900

Welcome to Cherrywood Gardens! This charming 2-bedroom, 1.5-bath condominium offers 953 sq. ft. of comfortable living space in the heart of Maitland. Step inside to find an inviting living and dining room combo, a bright kitchen with included appliances, and a primary suite with a walk-in closet. Enjoy your mornings on the front porch or take advantage of the community’s amenities, including a pool & clubhouse. Association fees cover water, sewer, trash, exterior maintenance, and grounds upkeep—making for worry-free living. Located near top-rated schools, shopping, dining, and major roadways, this home provides both comfort and convenience. Whether you’re a first-time buyer, downsizing, or looking for an investment, this condo is a great opportunity to own in a desirable Maitland community.

2 Beds ⋅ 2 Baths ⋅ Cherrywood Gardens SubDv. ⋅ 32751 Zip Code

Welcome to Cherrywood Gardens! This charming 2-bedroom, 1.5-bath condominium offers 953 sq. ft. of comfortable living space in the heart of Maitland. Step inside to find an inviting living and dining room combo, a bright kitchen with included appliances, and a primary suite with a walk-in closet. Enjoy your mornings on the front porch or take advantage of the community’s amenities, including a pool & clubhouse. Association fees cover water, sewer, trash, exterior maintenance, and grounds upkeep—making for worry-free living. Located near top-rated schools, shopping, dining, and major roadways, this home provides both comfort and convenience. Whether you’re a first-time buyer, downsizing, or looking for an investment, this condo is a great opportunity to own in a desirable Maitland community.

107 Cherrywood Gardens Drive Unit 8, Maitland