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$379,000
3 Beds ⋅ 3 Baths ⋅ Oakland Shores SubDv. ⋅ 32751 Zip Code
Welcome to 518 Oak Lane — a bright and spacious 3-bedroom, 3-bath home with 1,999 sq ft on a 0.33-acre lot in one of Maitland’s most desirable neighborhoods. On the market for the first time in nearly 50 years, this well-maintained property offers timeless charm, modern updates, and strong potential. Each bedroom features a walk-in closet, and all three bathrooms are designed for comfort and privacy. The home includes a large laundry room, built-in storage, and an open, light-filled layout with potential to connect the kitchen and living areas. Recent upgrades include a new roof (2024), new hot water tanks (2025), and replumb (2025), making it move-in ready. The oversized driveway offers ample parking, and with no HOA, you have freedom to personalize. Located near top-rated schools, parks, shopping, dining, and major highways — just minutes from downtown Maitland and Winter Park. Whether you're looking to renovate or invest, this home is a rare find with lasting value. This home may be under audio/visual surveillance.

518 Oak Lane, Maitland
$575,000
4 Beds ⋅ 3 Baths ⋅ Stonewood SubDv. ⋅ 32751 Zip Code
Nestled on a gorgeous tree-lined street, this charming residence exudes warmth, elegance, and timeless appeal. From the moment you arrive, the excellent curb appeal draws you in — with an established landscaped yard, paver driveway and walkways, classic brick exterior with shutters, and newer front and garage doors that set the tone for what awaits inside. Step into an inviting home where quality craftsmanship meets modern updates. The updated kitchen is a true showpiece, featuring granite countertops, solid wood cabinetry, tiled backsplash, breakfast bar with pendant lighting, and stainless steel appliances, including a Bosch dishwasher (2024) and a new double oven (2021). Throughout the main living areas, you’ll find gleaming hardwood floors and crown molding, enhancing the home’s sophisticated style. Large windows and solar tubes in the kitchen and family room fill the space with beautiful natural light. Enjoy two cozy wood-burning fireplaces — one in the family room and one in the living room — each flanked by built-in shelving and cabinetry. The living room’s large picturesque window offers the perfect spot for seasonal décor or simply enjoying the tranquil view. A separate dining room with built-in cabinets, crown molding, and sliders to the back porch makes entertaining effortless. The primary suite is spacious and serene, featuring a walk-in closet, crown molding, and a beautifully updated en suite bath with granite counters, tiled shower with glass enclosure, updated lighting and fixtures, and a new TOTO toilet. The three oversized secondary bedrooms offer ample closet space; one is currently used as an office. The updated guest bath includes granite countertops and modern finishes. The large inside laundry room, conveniently located off the kitchen, provides abundant cabinet and counter space, a utility sink, and two pantries, plus a private half bath with a new high-rise toilet for guests. Step into the tiled Florida room, where large windows and motorized retractable screens invite you to relax and enjoy the gorgeous, manicured backyard views. Off the Florida room, a brick porch with a retractable awning and coach lights provides a peaceful spot for morning coffee or evening gatherings. The fenced backyard features a paver-lined walkway and lush landscaping for added privacy and charm. Recent updates include: HVAC (2023) • Whole House Water Softener (2021) • Washer (2023) • Dryer (2019) • Water Heater (2021) • Porch Awning (2016) • Range (2021) • Refrigerator (2016) • Bosch Dishwasher (2024) • Roof (2013) replumbed (2002) Located near Maitland Avenue, I-4, and 414, this home offers easy access to dining, shopping, parks, the Maitland Farmers Market, and top-rated schools. Come see why homes in Stonewood are so highly sought-after — this one truly has it all: charm, comfort, and convenience in one of Maitland’s most picturesque neighborhoods.

448 Plumhollow Lane, Maitland
$775,000
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
$330,000
2 Beds ⋅ 1 Baths ⋅ Greenwood Gardens Rep SubDv. ⋅ 32751 Zip Code
COZY, 2 bedroom, 1 bath, 1 car garage home with a HUGE lot in a central location is ready for its new owners! As you enter, you will notice the OPEN living room and kitchen. The kitchen has custom wood cabinets, tile counters and backsplash. A large breakfast bar and eat-in nook area for your comfort. The bathroom is modern and sleek. Outside in the backyard, your OASIS awaits! There are fruit trees, areas for relaxing and a shed for storage. This home is in a NO HORN area of the railroad tracks that service the Sunrail and Amtrak. The Sunrail Station is within walking distance to the home for an easy work commute. NEWER ROOF, NEWER WINDOWS, updated electrical panel, tankless water heater, GAS stove, surround sound throughout as well. NO HOA. 30 minutes to downtown Orlando, 15 minutes to I-4 interstate and 5 minutes to 17-92. Whether you are looking for a great starter home, investment property or want to start from scratch and build your dream home, this one could be yours!!

735 Gamewell Avenue, Maitland
$221,000
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
$385,000
3 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
Experience Modern Florida Living at Its Finest Step inside this fully remodeled 3-bedroom, 2-bathroom residence and discover a seamless blend of sophistication, comfort, and everyday functionality. With a spacious 2-car garage, a welcoming front porch, and a large screened-in patio, this home offers the ideal balance of indoor elegance and outdoor tranquility. From the moment you enter, natural light fills the open-concept living and dining areas, highlighting the exquisite craftsmanship and premium finishes throughout. The gourmet chef’s kitchen is the true centerpiece — boasting custom cabinetry, sleek quartz countertops, a designer tile backsplash, and top-of-the-line stainless steel appliances. Whether you’re preparing weekday meals or hosting a dinner party, this kitchen delivers style and performance in perfect harmony. The home’s layout is thoughtfully designed for both comfort and connection. The living spaces flow effortlessly toward the screened-in patio, creating an inviting atmosphere for entertaining, relaxing, or enjoying quiet evenings in your own private retreat. Each of the two spa-inspired bathrooms has been completely transformed with luxury tile, contemporary vanities, and premium fixtures — evoking the serenity of a high-end resort. The primary suite serves as a peaceful haven, featuring generous space, soft natural light, and a modern ensuite designed for relaxation and rejuvenation. Step outside and enjoy the Florida lifestyle from your oversized screened patio, ideal for morning coffee, weekend gatherings, or simply unwinding under the stars. The 2-car garage provides plenty of room for vehicles and storage, adding convenience to your daily routine. Perfectly situated with easy access to major highways, this home offers unbeatable proximity to fine dining, upscale shopping, and world-famous theme parks. Whether you’re commuting, exploring, or entertaining, you’ll find yourself at the center of it all — without sacrificing peace and privacy at home. Every element of this remodel has been thoughtfully chosen to create a residence that feels brand new, yet instantly welcoming. From the modern finishes to the open layout and outdoor living space, this property captures the essence of effortless Florida living. Come experience the perfect combination of design, comfort, and location — and fall in love with the home you’ve been waiting for.

314 Banyan Drive, Maitland
$549,000
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
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
$350,000
3 Beds ⋅ 2 Baths ⋅ Druid Hills Park SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. GREAT OPPORTUNITY FOR FIRST TIME HOMEBUYERS AND INVESTORS TO TAKE ADVANTAGE OF THIS BELOW MEDIAN PRICE, $420,000 FOR SINGLE FAMILY AS OF MAY 2025, PROPERTY IN SOUGHT AFTER MAITLAND COMMUNITY OF DRUID HILLS. THIS PROPERTY BOASTS 3 BEDROOMS AND 2 BATHROOMS WITH A 2 CAR GARAGE NOT TO MENTION A DRIVEWAY FOR 4 OTHER CARS. ROOF IS NEW AS OF 2022, COMPLETE HVAC SYSTEM AIR HANDLER AND COMPRESSOR NEW AS OF 2023, CROWN MOLDING THRU OUT, SPACIOUS LOT WITH MATURE LANDSCAPING, RECENTLY REPLACED SEPTIC TANK PLUMBING PIPE, AND MORE. THIS PROPERTY IS CLOSE TO EVERYTHING. DOWNTOWN MAITLAND, WINTER PARK, AND ORLANDO JUST MINUTES AWAY. GREAT ACCESS TO I4 & THE 414. ORANGEWOOD CHRISTIAN SCHOOL JUST A FEW BLOCKS AWAY AND ALTAMONTE MALL JUST DOWN THE STREET. THIS WOULD BE A FANTASTIC STARTER HOME TO BEGIN TO BUILD A REAL ESTATE PORTFOLIO.

363 Croton Drive, Maitland
$335,000
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
$583,900
3 Beds ⋅ 2 Baths ⋅ Brittany Gardens SubDv. ⋅ 32751 Zip Code
Welcome to this beautifully appointed single-story, single-family home located in one of Maitland’s most exclusive gated communities. Nestled on the tranquil shores of Howell Creek and overlooking protected conservation land in the front, this residence offers a rare combination of privacy, natural beauty, and refined living. Step inside to an open and airy layout filled with natural light and serene water views. This residence features a split floor plan with 3 Bedrooms and 2 Full Bathrooms. The Floor Plan includes a Foyer, Formal Dining room with architectural designs, spacious living room with a gas fireplace, Open concept kitchen with generous cabinetry and countertop space, and a cozy dinette. The living spaces are thoughtfully designed for both relaxation and entertaining, featuring new vinyl plank flooring throughout the home. The primary suite offers a tranquil retreat with its own en-suite bath, while the additional bedrooms are ideal for family, guests, or a home office. Enjoy the outdoors in your private backyard oasis, where mature landscaping and direct frontage to Howell Creek create a serene setting for morning coffee or evening sunsets on the tiled screened porch or extended tile patio. The gated community provides added security all within a quiet, well-maintained environment. Just minutes to Park Avenue in Winter Park, Maitland Social, City Centre and Lake Lilly where you can enjoy Local Dining, Kelly's Ice Cream, Boutique Shopping, Farmer's Markets and Parks. Interlachen Country Club, The Racquet Club, WP9 are easily accessible. I-4, 417, Maitland Exchange and all the daily living needs such as Publix, Walgreens and CVS are within reach. Brittany Gardens Residents enjoy beautiful Common Areas that include Access to Howell Creek from the shore for fishing or non motor boat adventures and Brittany Park.

2634 Ultra Vista Drive, Maitland
$675,000
3 Beds ⋅ 2 Baths ⋅ Dixie Terrace SubDv. ⋅ 32751 Zip Code
Welcome to 1655 Sunnyside Drive, a beautifully charming home nestled on a picturesque corner lot in the heart of Maitland. Set on classic brick-lined roads, this 3-bedroom, 2-bathroom residence offers 1,418 square feet of thoughtfully designed living space filled with character and warmth. From the moment you arrive, you'll notice the inviting curb appeal, mature landscaping, and the undeniable charm that sets this home apart from the rest. Inside, the home exudes personality with unique architectural touches, cozy living spaces, and abundant natural light throughout. The well-appointed kitchen flows effortlessly into the main living area, making it perfect for both relaxing and entertaining. Each bedroom is spacious and comfortable, while the bathrooms offer tasteful finishes. Whether you're sipping coffee on the front porch or enjoying the peaceful surroundings, you'll feel right at home in this special space. Situated just minutes from the vibrant shops and restaurants of Park Avenue, this home also features two separate driveways, offering plenty of parking for guests or multiple vehicles—a rare find in this area. With its unbeatable location, timeless charm, and practical layout, 1655 Sunnyside Drive is the perfect blend of convenience and character. Don’t miss your opportunity to own a true gem in one of Maitland’s most desirable neighborhoods. ROOF: 2021 PLUMBING: 2021 AC: 2021 ELECTRICAL: 2021

1655 Sunnyside Drive, Maitland
$539,900
3 Beds ⋅ 2 Baths ⋅ Roosevelt Place SubDv. ⋅ 32751 Zip Code
This charming home boasts a wealth of valuable upgrades and improvements, making it an enticing opportunity for anyone seeking a move-in ready property The roof was replaced in 2024, ensuring long-lasting durability. A significant renovation in 2024 Both Bathrooms FULLY REMODELED, New AC inside and outside, all new baseboards too much to list. Extra Large kitchen, including all kitchen appliances and luxurious vinyl plank flooring, with extra flooring thoughtfully left in the house for future use. Two electric fireplaces provide cozy ambiance, and a fully functional wood fireplace offers additional charm and warmth if the buyer wishes to restore it. The property also received a host of exterior enhancements in 2017 and 2018, including a paver patio, fence, and a newly installed drain field for the septic system. The well pump was replaced around the same time Refurbished water treatment system. A relatively new Kinetico Premier water system, though exact installation date eludes memory, comes with operational paperwork for easy use. Further updates in 2020 include new windows in the garage and three bedrooms, a generator switch box, and new electrical panels. The attic received fresh insulation, and the ducts were professionally cleaned, ensuring energy efficiency. To top it all off, a brand-new shed was added in 2022, providing ample storage space for your convenience. This meticulously maintained property is a true gem, offering both modern amenities and peace of mind for years to come. Don't miss the chance to make it your own!

135 Roosevelt Place, Maitland
$770,000
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
$600,000
Hollieanna Shores SubDv. ⋅ 32751 Zip Code
Perfect opportunity to make this your dream home or add to your investment portfolio. This home is located on a 8x100 lot in the heart of Maitland and is walking to distance to Dommerich Elementary and Maitland Middle schools. This property provides loads of potential and offers a fenced backyard and a 2-car garage. Set up your showing today.

107 Tangelo Court, Maitland
$600,000
3 Beds ⋅ 3 Baths ⋅ Hollieanna Shores SubDv. ⋅ 32751 Zip Code
Perfect opportunity to make this your dream home or add to your investment portfolio. This home is located on an 80x100 lot in the heart of Maitland and is walking to distance to Dommerich Elementary and Maitland Middle schools. This property provides loads of potential and offers a fenced backyard and a 2-car garage. Set up your showing today.

107 Tangelo Court, Maitland
$575,000
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
$792,150
3 Beds ⋅ 2 Baths ⋅ Northwood Heights SubDv. ⋅ 32751 Zip Code
Perfectly positioned on the tranquil shores of Lake Seminary, this beautiful home offers the ultimate lakefront lifestyle in the heart of Maitland. From the moment you arrive, the home’s refreshed landscaping and elegant façade set the tone for what awaits inside. Step through the doors and you’re greeted by open living spaces accented by engineered hardwood floors, stylish finishes, and large windows that frame breathtaking views of the lake. The kitchen is a showcase of both function and design, featuring stainless steel appliances, generous counter space, and an open layout perfect for both entertaining and everyday living. The living room takes full advantage of the home’s lakefront setting, offering panoramic water views. The primary suite serves as a private retreat, featuring a large bathroom with dual vanities, a walk-in shower, and a spacious closet. Outdoors, the expansive backyard offers endless possibilities, whether you envision a custom pool, extended patio, or simply space to unwind and entertain with stunning lake views. An above-ground hot tub and patio overlook the glistening lake, creating the perfect setting to unwind while enjoying kayaking, boating, and fishing right from your own backyard. Set on nearly an acre of pristine land, the property features a rare combination of privacy, space, and stunning water views all just minutes from Maitland’s vibrant dining scene and major roadways, this home offers the perfect blend of lakeside tranquility and everyday convenience.

195 E Faith Terrace, Maitland
$571,430
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
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
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
$680,000
3 Beds ⋅ 4 Baths ⋅ Orangedale Park SubDv. ⋅ 32751 Zip Code
HUGE Price Reduction!! There is simply nothing that compares to this deal! This exquisite attached single family home blends contemporary elegance with unbeatable convenience in a truly coveted Maitland address. Just a stroll from Maitland Preparatory School and mere minutes from the vibrant heart of Downtown Winter Park, this residence offers the best of both worlds. From the moment you arrive, you’ll sense the refined lifestyle within. soaring ceilings, abundant natural light, and premium finishes throughout. The chef’s kitchen is a showpiece sleek cabinetry, stone countertops, and top-tier appliances. Entertain effortlessly with open living spaces that flow seamlessly to relaxing patios or balconies. With 3 bedrooms and 3½ baths, each space is a sanctuary. The primary suite impresses with its spa-style bath and custom closets. Upstairs, the laundry is tucked neatly beside the bedrooms for ease and efficiency. Thoughtfully designed storage niches and built-ins complete the picture. The real magic is the location. You’re only 5 minutes from Winter Park’s world-class dining, boutique shops, cultural venues, riverside parks, and Sunday farmer’s market. Stroll through cobbled streets, enjoy al fresco cafés, or catch live music on Park Avenue this home gives you that full lifestyle. Live luxuriously in a community where neighbors share the same roof and an unspoken sense of sophistication reigns. While it feels like condominium living, this is fee simple ownership in a four-unit enclave with NO HOA fees. You get the benefits without the burden. This is more than just a home it’s a statement. Don’t miss your opportunity to own a residence that’s as beautiful as it is brilliantly located.

183 Orange Place, Maitland
$970,000
4 Beds ⋅ 3 Baths ⋅ Dommerich Hills SubDv. ⋅ 32751 Zip Code
Sold data entry only

2031 Chippewa Trail, Maitland
$650,000
4 Beds ⋅ 3 Baths ⋅ Maitland Woods SubDv. ⋅ 32751 Zip Code
Incredible Opportunity to create your own dream home in the coveted Lake Sybelia / Maitland Woods neighborhood !! Spacious, One Story Living in this 4 bedroom, 3 bathroom home. Located just steps from Lake Sybelia Park. Convenient to I-4, Maitland Center, Winter Park, Altamonte Springs and downtown Orlando. After decades of being the stage for shared love and great family memories, this home is being offered to the market for the first time since 1974 - and offers the opportunity to make it your own for decades to come. Large living spaces including a kitchen with gas Viking range, additional built-in oven, two prep areas, two dishwashers (Bosch and Fisher & Paykel), 48" stainless refrigerator and deep stainless sinks. The living room includes a gas fireplace and opens to the adjacent Florida/Sun Room. The Primary Suite includes a sitting area with fireplace and a large ensuite bathroom. A covered hot tub/spa is adjacent to the Primary Bath. This spacious home is located on a generous, .39 acre, corner lot with the front of the home facing Willowbrook Trail and the garage entry from N. Lake Sybelia Dr. Roof and Skylights replaced in 2017. Separate utility shed for storing gardening tools or creating a workshop.

1100 Willowbrook Trail, Maitland
$350,000
3 Beds ⋅ 2 Baths ⋅ English Ests Unit 1 SubDv. ⋅ 32751 Zip Code
One or more photo(s) has been virtually staged. Nestled in the sought-after English Estates neighborhood, this classic Medallion home offers timeless character and the perfect opportunity to make it your own. Featuring its original Medallion hallmark in the kitchen pantry, this retro gem includes formal living and dining rooms, a cozy breakfast nook off the galley-style kitchen, and original terrazzo flooring. Recent updates include a reroof and exterior paint (2021), fresh interior paint (2025), hot water tank (2021) and an upgraded A/C system with UV light (2019). Your new home was replumbed in 2015 and the electrical updated in 2012. The interior laundry room adds convenience, while the spacious enclosed and screened porch provides a peaceful retreat to relax and enjoy the evening sunset. Don't miss the chance to bring your vision to this well-maintained mid-century treasure.

2065 Derbyshire Road, Maitland
$365,000
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
$635,000
Dixie Terrace SubDv. ⋅ 32751 Zip Code
Tucked away on a quiet dead-end street, this rare double lot is framed by a stately mature oak tree, setting the tone for the estate you’ve always envisioned. Positioned right on the border of Maitland and Winter Park, the location offers the best of both worlds, minutes from Park Avenue’s dining and boutiques, lake days on Lake Maitland, and seamless connectivity to I-4. Surrounded by top-rated schools and established luxury homes, this property offers limitless potential to design and build with the builder of your choice. More than just land, this is an opportunity to create your own sanctuary in one of Central Florida’s most desired enclaves.

1630 Lyndale Boulevard, Maitland
$375,000
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
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
$285,000
3 Beds ⋅ 2 Baths ⋅ Lake Eulalia Heights SubDv. ⋅ 32751 Zip Code
Tucked away in a tranquil setting, this charming 1958 split-level home offers a peaceful retreat surrounded by lush, thoughtfully landscaped gardens. As you arrive, you’ll feel an immediate sense of calm, greeted by a welcoming stairway and a serene garden path that invites you to explore before you even step inside. The main level features a spacious, light-filled living and dining area—perfect for entertaining or relaxing with loved ones. Large windows frame picturesque views of the gardens, flooding the space with natural light. Beneath the main level carpet, discover the timeless beauty of original terrazzo flooring, just waiting to be uncovered and restored. The lower-level bonus room is designed for both fun and function, complete with custom cabinetry and a sleek granite bar—ideal for hosting game nights or casual gatherings. Whether you’re entertaining or unwinding, this space offers flexibility and comfort. Step outside into your own tropical oasis, where mature landscaping, stone pathways, and private garden nooks create a perfect environment for relaxation and connection with nature. *The info in MLS is thought to be correct but not guaranteed*

721 Lake Avenue, Maitland