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$645,000
3 Beds 2 Baths Greenwood Gardens Sec 02 Rep 01 SubDv. 32751 Zip Code
Under contract-accepting backup offers. Tucked away in the heart of Maitland, this thoughtfully updated three-bedroom, two bath residence blends everyday comfort with meaningful, modern upgrades. Freshly painted interior (June 2026) and a private spa pool WITH BRAND NEW POOL PUMP creates a serene outdoor retreat—perfect for unwinding or entertaining year-round in true Florida style. Inside, the home offers both function and peace of mind with a dedicated laundry room featuring a brand-new washer (2026) and newer dryer (2024). Major system updates have already been taken care of, including a new water heater (2025) and a recently installed HVAC system (April 2026), providing efficiency, reliability, and confidence from day one. Ideally located with close proximity to I-4 for easy commuting, and just a short walk to Maitland Community Park and Lake Lily, this home offers the perfect balance of convenience and lifestyle. A move-in-ready opportunity where the essential upgrades are already done for you.

910 Gamewell Avenue, Maitland

$1,199,000
4 Beds 4 Baths Lake Sybelia Cove Ph 01 SubDv. 32751 Zip Code
Now offered below recent appraised value, this exceptional residence combines luxury, location, and outstanding value in one of Maitland's most sought-after enclaves. Pride of ownership shines throughout this beautifully maintained original-owner home tucked away on a quiet cul-de-sac in the gated community of Sybelia Cove. Offering 4 bedrooms, 4 bathrooms, a side-entry 3-car garage, and 3,902 square feet, this spacious residence blends timeless design with thoughtful updates in one of Maitland’s most desirable locations. Inside, soaring ceilings and expansive windows fill the home with natural light, while the family room fireplace and wood flooring throughout the main entertaining spaces adds warmth and character. The functional floor plan features a private downstairs primary suite along with a dedicated office, creating flexibility for both everyday living and working from home. Upstairs, a spacious loft is accompanied by three additional bedrooms and bathrooms. Fresh carpeting in select areas enhances comfort throughout the home. The kitchen has been updated with refreshed cabinetry, countertops, and GE Café stainless steel appliances, flowing seamlessly into the main living spaces designed for entertaining and gathering. Step outside to a screened-in pool and outdoor living area designed for year-round enjoyment while taking advantage of breezes from nearby Lake Sybelia located just behind the home. A brand-new roof (2024) provides additional peace of mind. Located just moments from downtown Maitland’s shops, dining, and parks, this home offers the privacy of gated living with exceptional walkability and convenience. Call today for your private showing.

873 Cranes Court, Maitland

$549,000
5 Beds 3 Baths Northgate SubDv. 32751 Zip Code
*Seller is Offering 20k Credit to buyers at closing towards future upgrades!* This AMAZING!, spacious 5-bedroom, 3-bath split-level home is located in a fantastic neighborhood and is packed with standout features. Upstairs, you’ll find beautiful engineered hardwood flooring throughout the main living areas, with carpet in the bedrooms and tile in the baths. A stunning screened-in porch overlooks the backyard and pool, offering a perfect spot to relax or entertain. The bright and airy formal living room provides plenty of space, while the dining room includes sliding doors that lead out to the porch. The large eat-in kitchen offers ample cabinet storage and even features a convenient pass-through window to the porch/outside bar—ideal for hosting. The upper level includes three bedrooms two bathrooms. Just a few steps down, the lower level opens to a massive family room with tile floors set to entertain family and friends with two additional bedrooms with carpet and a full bath. Tile flooring runs throughout this level. Additional highlights include, updated windows, a re-piped plumbing system, updated Electrical, and a well-maintained interior full of character. The home comes with paid in full solar panels and a Terminix termite bond and Well Maintained sprinkler system on well. Washer/Dryer are located in the garage. The garage include cabinets for additional storage. The yard features mature Citrus trees and Magnolia trees adding to the home’s charm. With its flexible layout, inviting screened porch, and beautiful salt water pool area, this home truly has it all.

1511 Glastonberry Road, Maitland

$215,000
2 Beds 2 Baths Park Lake Twnhs SubDv. 32751 Zip Code
A beautiful affordable condo in Maitland. 2 bedrooms and 1 ½ baths with a 1 car garage. The kitchen has been updated with white cabinets and new counter tops. The appliances have been updated. There is a large dining room and separate living room. The utility room is on the 1st floor with an updated barn door for access. The 1st floor has wood flooring while the second floor has carpeting. The second floor has two bedrooms with an updated bathroom. The shower has been remodeled to allow easy access. This home has a large patio with artificial grass flooring. The one car garage is an added bonus. The property has had the window replaced, a new water heater (2026) and the electrical panel upgraded within the past couple of years. The A/C system was replaced in 2022. This wonderful unit is at a great price and will not last long.

814 Park Lake Circle Unit 8, Maitland

$1,695,000
4 Beds 5 Baths Lake Colony Ph 02 SubDv. 32751 Zip Code
Under contract-accepting backup offers. Priced for quick sale! Modern, mediterranean lakefront residence in one of Maitland’s most desirable GATED communities, positioned on a private cul-de-sac atop a natural rise. Set on over 1.3 acres with approximately 179 feet of frontage on Lake Jackson (ski lake), the property offers a rare combination of elevation, privacy and expansive water views in a central Maitland location with quick access to I-4, downtown Maitland and Park Avenue, Winter Park. Lake Colony Estates is conveniently located across the street from Orangewood School. The home was custom built by Keith Groninger, a 10-time Parade of Homes winner. A tree-lined drive leads to a paved driveway and a welcoming entry with imported hand-crafted 8-foot wood doors and tile roof. Inside, the foyer opens to a dramatic great room with 20-foot cathedral ceilings, clerestory windows and a floor-to-ceiling wood burning fireplace, butlers pantry and wet bar. The home has been refreshed with white interior paint, enhancing the natural light and giving the interiors a timeless backdrop. The gourmet kitchen is designed for both function and gathering, featuring 3cm granite countertops, a large island, 5-burner gas cooktop with custom stone and mortar arch detail, tumbled marble backsplash and vaulted ceilings with exposed wood beams sourced from Pennsylvania. Expansive lake-facing pocketing windows frame Lake Jackson and open the chef’s kitchen to the screened porch for effortless outdoor dining and entertaining The first-floor primary suite features engineered hardwood floors, direct access to the outdoor pool and a spacious bath finished in tumbled marble with a soaking tub, dual vanities and walk-in shower. A large custom walk-in closet provides generous storage. Upstairs, three oversized bedrooms each offer ensuite baths and a large bonus room overlooking the lake. Outdoor living is centered around the covered, screened porch, lakefront setting and gated pool. The private and expansive lawn -179 feet of shoreline, complemented by a private boathouse (newer lift) with direct access to Lake Jackson for boating, skiing, jet skis, canoes, paddleboards and more! Also, enjoy sunrise views over Lake Jackson! Additional features include two new ACs, oversized three-car garage, amazing storage and closet spaces, mature and new landscaping and carefully maintained architectural detailing throughout. Four point, roof certification and wind mitigation reports will be provided by the sellers. Seawall maintained by HOA. No flood insurance required on the home.

1244 E Lake Colony Drive, Maitland

$925,000
3 Beds 3 Baths Forest Brook 5th Sec SubDv. 32751 Zip Code
NEWLY PRICED TO SELL, UNDER APPRAISED VALUE, DO NOT MISS THIS OPPORTUNITY!! SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND FINISH has been REPLACED, REFRESHED and ELEVATED to perfection and just minutes from Winter Park. Located at 755 Woodside Road in the community of Forest Brook in Maitland with 3,054 Sq Ft. of living space, in a quiet CUL-DE- SAC, this 3 BEDROOM 3 FULL BATHROOM POOL home with 2 Car garage on a .31 ACRE LOT is effortless Florida living.**SOLAR PANELS-(Avg. utilities $40/MONTH) From the moment you arrive you will be impressed with the mature, manicured landscaping and architectural features that sets the tone for the quality you will find inside. The EXPANSIVE OPEN FLOOR PLAN draws you in with an effortless flow between living, dining, and entertaining spaces. SLEEK MODERN CABINETRY, MARBLE FLOORING and DESIGNER FIXTURES elevate every room. The chef-inspired kitchen features a LARGE CENTER ISLAND perfect for casual dining, meal prep or gathering with guests. A stylish PASS THROUG BAR connects seamlessly to the Florida Room making entertaining a breeze. The OVERSIZED PRIMARY SUITE is a true retreat with MARBLE FLOORING, an abundance of natural light and CUSTOM SLIDING GLASS DOORS leading to the expansive pool deck. The en-suite bathroom features FLOATING VANITIES, MARBLE FLOORING and a SEAMLESS GLASS ENCLOSED SHOWER and STAND ALONE TUB that continues the modern aesthetic that feels like a five star hotel everyday. Laundry with sink and overhead cabinets is centrally located near the kitchen and primary suite. The focal point of the family room is the stunning MARBLE FACED FIREPLACE. Two generously sized secondary bedrooms are located off the family room, sharing a beautiful bathroom featuring marble floors, floating dual sink vanity and walk-in shower-consistent with the finishes throughout. The Florida Room is where the fun truly begins. Currently set up as the ultimate entertainment space, this incredible space offers endless possibilities- playroom, game room, movie room or the perfect indoor/outdoor lounge for hosting family and friends.NEW OVERSIZED WINDOWS frame spectacular views of the pool, floods the space with natural light and seamlessly connect the indoors to the out. The THIRD FULL BATH located off the Florida Room serves as the POOL BATH with walk-in shower, Jacuzzi, floating vanity and premium finishes. This homes outdoor spaces provide something for everyone. The large, screened-in pool deck features a Tiki Bar and dedicated PROJECTOR SCREEN AREA (Screen & Tiki Bar CONVEY IN THE SALE) perfect for entertaining pool side.The side yard with artificial turf is clean, low maintenance, and pet friendly. A charming brick paver seating area creates as cozy spot to relax, unwind or let the pets roam freely. Enjoy the tranquility of this homes beautiful backyard. ADDITIONAL LIST OF UPGRADES: 2020 HARDSCAPE & LANDSCAPING, 2021 NEW WATER HEATER & POOL PUMP, 2024/2025 REPLACED LARGE AC AND DUCTWORK, AC PRIMARY SIDE UNIT, 2025 NEW FLORIDA ROOM WINDOWS, ADDED RID-O-RUST SYSTEM TO WELL FOR IRRIGATION, SCREENED IN POOL/DECK, SOLAR PANELS (to be paid off at closing) ADDED DRY BAR WITH UPPER AND LOWER CABINETS IN DINING AREA. Conveniently located minutes away from boutique shopping, acclaimed dining and vibrant entertainment of the beautiful city of Winter Park with easy access to Orlando and surrounding communities. This home won't last long. Call your Agent to schedule a showing today!

755 Woodside Road, Maitland

$169,900
2 Beds 1 Baths Visconti West SubDv. 32751 Zip Code
Amazing upgraded two-bedroom, one bath Condo in the gated waterfront community at Visconti in Maitland with features of spacious living and comfortability. This stunning Condo Unit features with large windows letting in plenty of natural light and giving the common living area a fresh air feel. The dining/living combo opens to a big, screened patio through sliding glass doors. The kitchen overlooks the living and dining room and contains a full suite, including the refrigerator, range, dishwasher, disposal and plenty of cabinet and countertop. The bedroom is also including a large walk-in closet. This unit has oversized laundry room that includes full-size washer and dryer.Visconti community comes with professional maintenance of Ponds, professionally landscaped and well-maintained common areas as well as a BEAUTIFUL Resort Style Pool and Club House along with tennis court, fitness, basketball court, car washing area ext. Primely located close to all shopping, entertainment areas and just minutes to major highways, I4. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures are not included to the listing

1375 Lake Shadow Circle Unit 11203, Maitland

$950,000
4 Beds 3 Baths Versailles SubDv. 32751 Zip Code
Virtually Staged. NEW PRICE! Nestled within the quiet, established community of Versailles, this exceptional residence invites you to slow down and savor the good life. Offering over 3,600 sq. ft., this home features 4 spacious bedrooms and 3 full baths, with a layout that is both functional and flexible. The PRIMARY SUITE is conveniently located on the MAIN FLOOR and features an EXPANSIVE ATTACHED OFFICE, CRAFT ROOM OR SITTING ROOM—perfect for today’s lifestyle. This generous space also presents a unique opportunity for reconfiguration, allowing you to expand the primary bedroom and/or create a truly luxurious bath retreat tailored to your vision. Upstairs, three additional BEDROOMS ARE IMPRESSIVELY SIZED, offering plenty of room for family or guests. A STANDOUT FEATURE of the home is the BONUS ROOM with its own private entrance, located just off the rear garage—ideal for a game room, media lounge, or entertainment hub complete with space for a pool table, ping pong table, and a large-screen TV. At the heart of the home, the EXPANSIVE 23 x14 kitchen is filled with potential and already equipped with premium appliances, including a SubZero refrigerator, separate SubZero freezer, and a Viking cooktop. Built-in desk space and charming banquet seating create a welcoming spot for casual dining and everyday moments. The inviting family room is designed for cozy evenings, featuring a wood-burning fireplace, beverage fridge, ice maker, and sink—perfect for entertaining or unwinding. For larger gatherings, the expansive living room and adjacent dining area provide an elegant backdrop, whether hosting dinner parties, game nights, or enjoying music by a grand piano. Step outside to your private oasis, set on NEARLY HALF OF AN ACRE of beautifully landscaped grounds. The generous deck surrounds a stunning 10-foot-deep SWIMMING POOL offering endless possibilities for outdoor entertaining, relaxation, and recreation. Life in Versailles extends beyond your front door. HOA Residents can enjoy PRIVATE ACCESS TO LAKE Minnehaha, complete with a dock—perfect for paddleboarding, kayaking, or soaking in breathtaking sunset views. Just beyond the back gate, Maitland Community Park offers an array of AMENITIES including playgrounds, tennis courts, basketball, racquetball, and scenic fitness trails. A convenient paved path even connects you to nearby shopping and dining, including Publix. Ideally located with easy access to Maitland Boulevard, SR 414, I-4, and 436, SUNRAIL station is close and ZONED IN TOP RATED SCHOOLS, this home offers both tranquility and convenience. With an optional HOA, you have the freedom to enjoy the community on your terms. This is more than a home—it’s a lifestyle waiting to be embraced. Make your appointment today to view this lovely home!

1001 Versailles Court, Maitland

$420,000
3 Beds 3 Baths Moorings On Lake Maitland Condo Bldg 04 SubDv. 32751 Zip Code
Welcome to The Moorings on Lake Maitland, one of the most in-demand communities in the area. Consider this unit, 3-bedrooms and 2-1/2 baths, approximately 1700 square feet of living space with a 1-car garage, and overlooking the beautiful peaceful courtyard, to be your blank slate. Gleaming wood floors and fresh painted throughout, it is just waiting for you to make it your own. You'll love this comfortable living space, and there is so much to work with! From the entry foyer you'll find the eat-in kitchen immediately on your right. Head through the kitchen to the spacious dining room, and into the living room with vaulted ceiling and zen garden view. Half-bath and inviting screened lanai complete the ground floor living space. Upstairs you'll find the large primary suite, also overlooking the courtyard, and two more bedrooms, both front-facing, and a full bath in the hallway. The laundry room with washer, dryer and utility sink is in the garage. The grounds, pool and club house are maintained by the community, so all you have to so is enjoy the ambiance of the beautiful grounds and the lakefront. The many advantages to this convenient location include being on Lake Maitland, and, easy access to necessities like grocery and drug stores, and restaurants within walking distance. This one is priced to sell, so don't miss this opportunity!

245 Quayside Circle, Maitland

$800,000
4 Beds 2 Baths Maitland Woods SubDv. 32751 Zip Code
Towering oaks and Spanish moss flowing in the breeze set the stage for this oasis in the heart of Maitland. This charming 4 bedroom, 2 bath abode with a tropical courtyard pool has been lovingly updated with luxe finishes and features. Step inside the covered airy breezeway where travertine pavers surround the screen enclosed pool deck and the true front door entrance. Beautiful crown moulding and wood-look ceramic tile flooring runs throughout the house (no carpeting). Double pane windows and sliders with build-in blinds accent the courtyard views. Arched doorways open to the poolside family room with wood-burning marble-surround fireplace and custom built-ins. Large enough for all your family and friends, the spacious living and dining rooms with custom window shutters and recessed lighting is sure to impress. Total kitchen remodel features handmade subway tile backsplash, quartz countertops, stainless steel appliances, and the most charming in-kitchen dining area with views out to the pool. A renovated full hall bathroom with double sink quartz vanity and tub/shower combo opens to the pool and is close to the 3 guest bedrooms (one bedroom also has sliders to the pool). Your large primary suite is tucked away at the back of the house with dressing area, walk-in closet, and separate toilet/shower room. And the views to the pool through the double sliders are inspiring. Indoor/outdoor living is a breeze in this unique Maitland courtyard style pool home. Plus, a fully fenced backyard is still big enough for children and pets to play. You’ll love the location with easy access to I-4, the shops and restaurants of Downtown Maitland and Lake Lily (home of a weekly farmer’s market), and walking distance to Lake Sybelia and lakefront Homer Hough Park. Improvements include NEW hot water heater 2026; NEW solar pool heater 2022; NEW paver driveway and motor court 2022; NEW roof 2021; NEW travertine pool deck 2021; NEW HVAC 2020; NEW Gernerac house generator; and Replumb CPVC 2015.

1170 Willowbrook Trail, Maitland

$497,000
3 Beds 3 Baths Maitland Village SubDv. 32751 Zip Code
You've been searching for a single-family home — the space, the privacy, the pride of ownership. What if you could have all of that and never mow the lawn, pay a cable bill, or worry about the water bill again? Welcome to 2011 Michael Tiago Circle, where the spaciousness and elegance of single-family home living meets the effortless ease of a low-maintenance lifestyle — truly the best of both worlds! This stunning, move-in ready, Mediterranean-style end-unit townhome is located in the gated enclave of Maitland Village. Step inside and you'll immediately notice the soaring ceilings, extra windows of an end-unit, added natural light and elevated craftsmanship that sets this home apart: decorative chair-rail and wainscoting grace the first floor and crown molding flows throughout every level, lending an air of elegance and sophistication. The open-concept kitchen is a true showstopper, featuring granite countertops, Samsung stainless steel appliances, and 42" custom cabinetry thoughtfully designed for real life — including a pantry cabinet with pull-out drawers, a corner Lazy Susan that maximizes every inch of storage, and a dedicated pull-out trash and recycling cabinet to keep things tidy and tucked away. Whether you're hosting a dinner party or meal-prepping for the week, this kitchen is ready for it all. Sliding glass doors open to your private covered porch overlooking a serene pond— the perfect backdrop for morning coffee or evening unwinding. Upstairs, a versatile loft provides the perfect flex space for a home office, exercise space or playroom. The large primary suite features a walk-in closet and a luxurious bath with dual vanities, soaking tub, glass enclosed shower and private water closet. The other two sizeable bedrooms are down the hall for privacy and share a full bathroom. The Maitland Village HOA fee includes community gated access, swimming pool and clubhouse, lawn/shrub care, irrigation, cable/high-speed internet, water/sewer, trash/recycle pick-up and pest inspections. Conveniently located with easy access to I-4, SR 414/429 and just minutes to local parks, the Orlando Sportsplex, Maitland City Center, Winter Park and Altamonte Springs for a variety of shopping, dining and entertainment options. Make your appointment to see this beautiful home today!

2011 Michael Tiago Circle, Maitland

$190,000
2 Beds 2 Baths Visconti West SubDv. 32751 Zip Code
Virtually Staged. Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in the sought-after Visconti community, where comfort, convenience, and lifestyle come together. Located on the third floor, this light-filled residence features soaring vaulted ceilings that create an open, airy feel, complemented by abundant natural light throughout. Ideally positioned just steps from the clubhouse, you’ll enjoy effortless access to resort-style amenities, including a sparkling pool and fully equipped fitness center—perfect for both relaxation and an active lifestyle. This move-in ready condo is an excellent opportunity for both homeowners and investors alike. With quick access to I-4, commuting to Downtown Orlando is easy, while the shopping, dining, and entertainment of Altamonte Springs are just minutes away. Opportunities like this in Visconti don’t last—schedule your private showing today.

1100 Lake Shadow Circle Unit 2307, Maitland

$973,600
4 Beds 3 Baths Highland Park Estates SubDv. 32751 Zip Code
Fully renovated pool home in the heart of Dommerich featuring a rare dual-primary layout and a 2019-built owner’s suite addition—designed for modern living and effortless maintenance. Originally built in 1967 and completely reimagined in 2019, the home blends timeless character with major system upgrades including roof, HVAC, plumbing, electrical, windows, and doors—providing peace of mind rarely found in this area. The home is vacant and move-in ready. The open-concept living and dining areas flow seamlessly into a private, resort-style backyard featuring a screened-in pool, covered patio, and low-maintenance landscaping. With xeriscaped grounds, paver walkways, and perimeter planting beds, the outdoor space is designed to be enjoyed—not managed. The kitchen is built for both function and flow, offering extensive drawer-based cabinetry, a dedicated coffee bar, natural gas cooking, and direct access to the main living areas and garage. The home is equipped with natural gas, supporting the cooktop, dryer, tankless water heater, and pool/spa heater—providing enhanced efficiency, faster performance, and lower operating costs compared to all-electric homes. The 2019-built primary suite is a true retreat with vaulted ceilings, pool access, a custom walk-in closet, en-suite bath, and a dedicated laundry space. A second primary bedroom with en-suite bath also serves as a pool bath—ideal for guests, multigenerational living, or flexible use. Two additional bedrooms and a shared hall bath complete the layout. Located in one of Central Florida’s most established and sought-after neighborhoods, Dommerich offers top-rated schools, tree-lined streets, parks, and unmatched proximity to shopping, dining, and major roadways. Vacant and move-in ready. Homes with this layout and level of renovation in Dommerich rarely come available. And the price was recently repositioned to provide one of the best values among fully renovated pool homes in Dommerich.

921 N Thistle Lane, Maitland

$467,000
2 Beds 2 Baths Moorings On Lake Maitland Condo SubDv. 32751 Zip Code
Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated spacious kitchen features stainless steel appliances and a breakfast nook situated in a bay window. The dining living room combo is very spacious making it perfect for relaxing or entertaining. The condo offers washer and dryer in the unit as well as a private storage closet on the same floor just across the hall. The Moorings Lakefront community offers an amazing recently updated pool and spa area along a large clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this condo and community offers an amazing combination of comfort and convenience.

204 Quayside Circle Unit 201, Maitland

$735,000
5 Beds 3 Baths Dommerich Hills 6th Add SubDv. 32751 Zip Code
Completely Remodeled 2026 | Single-Story | Split Floorplan | The redesigned kitchen features 42" shaker cabinetry, Calcutta quartz countertops, a marble backsplash, and new stainless steel Fisher & Paykel appliances. Bathrooms have been completely remodeled with updated finishes. Luxury vinyl flooring extends through all common areas, complemented by LED recessed lighting and updated fixtures throughout. The open layout provides clear sight-lines between the kitchen and family room, creating a connected main living area. The pavers meet manicured lawns and fresh landscaping for a clean, contemporary finish that is 100% move-in ready. Additional features include an interior laundry room and a fully fenced backyard with a pool. Enjoy being just minutes from Park Avenue, Lake Lily, and Maitland City Centre where you'll find farmers markets, local dining, and boutique shopping. With easy access to I-4, 417, and the Maitland Exchange, you're well connected to everything Central Florida has to offer.

2809 Waumpi Trail, Maitland

$362,500
3 Beds 3 Baths Enclave/Maitland A-F SubDv. 32751 Zip Code
This beautiful Maitland Florida town home feels like living in a gated resort! 3 bedrooms, 2 1/2 baths, plus garage and loaded with upgrades including hardwood floors on both levels, crown molding, tall wood cabinets, stone counters and so much more. Welcoming entry foyer with half bath, kitchen with island sink, large breakfast bar, stainless appliances, granite counters and custom backsplash. Inviting living room and dining area offer plenty of space for entertaining, french door opens to private covered porch which overlooks the rear yard. Upstairs the ensuite primary bedroom has a walk-in closet, great covered balcony area and a dual sink bathroom with glass enclosed shower. Additional 2 bedrooms in the front of the upstairs share a hall bath and laundry closet with washer and dryer included. Montacino is a gated European feeling award winning community with amazing pool area, lake frontage and a convenient location to shopping and i4. This townhouse has a quiet location within the community offering privacy in the back area. All exterior maintenance is included (roof and paint too)! HOA dues include new fiber with internet and channel package and all Montacino amenities.

1393 Benevolent Street, Maitland

$159,950
2 Beds 2 Baths Visconti West Condo SubDv. 32751 Zip Code
Welcome to Visconti! A Gated Waterfront Community in the Heart of Maitland. Step into an easy, low-maintenance living with this move-in ready 2-bedroom, 2-bath condo located on the third floor, offering added privacy and a peaceful, elevated feel. With all new flooring and fresh interior paint, this home is completely refreshed and ready for its next owner. The split floor plan layout offers a comfortable and functional flow, ideal for both everyday living and entertaining. Natural light fills the space, creating a bright and inviting atmosphere throughout. Whether you’re starting your day or winding down in the evening, this home delivers a relaxed, low-stress environment that truly feels like home. Located within the highly desirable Visconti community, residents enjoy resort-style amenities including a sparkling pool, fitness center, clubhouse, tennis and basketball courts, playground, and scenic walking paths with a waterfront gazebo. The gated entry and beautifully maintained grounds enhance both privacy and curb appeal. The HOA includes water service and valet trash, helping simplify your monthly expenses and making condo living even more convenient. Positioned in one of Maitland’s most central locations, you’ll have quick access to I-4, 414, and 434, with nearby shopping, dining, and entertainment options including Maitland Promenade, Winter Park Village, Cranes Roost Park, and Uptown Altamonte. Downtown Orlando is just a short drive away. If you’re looking for a fully updated, move-in ready condo in a gated community with strong amenities and an unbeatable location, this one checks all the boxes.

1440 Lake Shadow Circle Unit 8305, Maitland

$113,000
1 Beds 1 Baths Carrington Park A Condo SubDv. 32751 Zip Code
Great opportunity to own this 1-bedroom, 1-bathroom first-floor unit in a desirable and well-maintained community! This property offers a comfortable and functional layout with easy first-floor access, perfect for both homeowners and investors alike. Currently tenant-occupied with a lease in place through June 30, 2026, providing immediate rental income with future flexibility for personal use. Residents enjoy access to excellent community amenities, including a sparkling pool, fitness center, and playground, all within a lovely and welcoming environment. Conveniently located near major highways, shopping, dining, and entertainment, this property offers both lifestyle and investment potential. Don’t miss this versatile opportunity!

2422 Branch Way Unit 100, Maitland

$595,000
4 Beds 2 Baths English Woods SubDv. 32751 Zip Code
Welcome to 2466 Fieldingwood Rd, a fully re-imagined pool home in Maitland, FL. This 4 bedroom, 2 bathroom home has been completely renovated from top to bottom with a fresh, modern feel that is move-in ready and designed for today’s lifestyle. From the moment you arrive, you will notice the clean exterior, updated landscaping, and quiet street that sets the tone for the rest of the home. ALL major systems have been updates: Roof 2022, Plumbing 2024, Hot Water Heater 2024, AC 2016, and newer pool equiptment. Inside, the layout flows effortlessly with light-filled living spaces, updated flooring, and a bright, open feel throughout. The kitchen and main living areas connect seamlessly, making it perfect for both everyday living and entertaining. Step outside to your private backyard retreat featuring a newly refreshed pool and spacious deck area. This is the kind of space that feels like Florida living should. Whether you are hosting friends or enjoying a quiet evening at home, this backyard delivers. The bedrooms offer comfortable, flexible space for families, guests, or a home office, while the primary suite provides a clean and calming place to unwind. Located in English Estates, you are just minutes from Winter Park with easy access to 17-92, 436, and Red Bug Lake Road. Commuting is simple with quick access to I-4 and the express lane entrance, getting you to downtown Orlando efficiently. If you are looking for a fully updated home with a pool in a central location that actually makes your day-to-day life easier, this is one you need to see in person.

2466 Fieldingwood Road, Maitland

$111,000
1 Beds 1 Baths Carrington Park A Condo SubDv. 32751 Zip Code
Discover this beautifully maintained 1-bedroom, 1-bath condo in the highly desirable Banyan Tree Condominium of Maitland. Located on the second floor, this unit boasts abundant natural light, a functional layout, and low-maintenance living—perfect for families, first-time buyers, or savvy investors seeking rental income. Enjoy affordable HOA fees ($255.86/month) covering building insurance, pool, landscaping, and common areas. Situated in Seminole County, close to top-rated schools, shopping, dining, and major highways. Flood Zone X, no CDD, not currently homesteaded. This is an exceptional opportunity to own a comfortable home or a turnkey investment property. Act now—buyer to verify all information including school zoning, rental restrictions, and flood insurance requirements.

416 Banyon Tree Circle Unit 206, Maitland

$769,000
4 Beds 2 Baths Maitland Isle SubDv. 32751 Zip Code
Welcome to an exceptional residence in the Maitland Isle subdivision, where timeless elegance meets modern comfort. This beautifully updated four-bedroom, two-bath home spans 2,413 square feet and offers exclusive private lake access to Lake Maitland on the prestigious Winter Park Chain of Lakes. Designed for refined living and effortless entertaining, the home features a thoughtfully curated interior with upgraded finishes, including laminate flooring, enhanced baseboards, wet bar in family room and a seamless, light-filled layout. The kitchen, enhanced with quality wood cabinetry, flows seamlessly into the main living areas, while generously sized split bedroom plan provides flexibility for family, guests or a home office. A comprehensive list of upgrades reflects pride of ownership such as a newer roof (2020), resurfaced pool (2020), advanced air-conditioning system with Enviracare Elite air purification (2019), updated electrical panels (2012), replumbing (2006) and a water heater (2022). More recent enhancements include full interior and exterior painting (2025), a newly installed wooden fence and a serviced sprinkler system with a new impeller (2026). Outdoors, enjoy a private retreat with a sparkling pool and covered deck with an outdoor entertainment area, ideal for year-round Florida living. Residents of Maitland Isle benefit from exclusive access to Lake Maitland, offering a rare opportunity for boating and waterfront recreation within one of Central Florida’s desirable communities. Ideally in a top-rated school district and just a short distance to the charm of downtown Maitland, this home delivers a lifestyle of convenience, prestige and tranquility. A rare offering where location, quality and lifestyle converge.

101 Mariner Way, Maitland

$779,000
3 Beds 2 Baths Highland Park Estates First Add SubDv. 32751 Zip Code
HUGE PRICE REDUCTION. Welcome to this beautifully renovated pool home in the highly sought-after Dommerich neighborhood of Maitland. Offering over 2,000 square feet of living space, this 3-bedroom, 2-bath residence perfectly blends modern upgrades with comfortable, functional living. Inside the home is designed for both everyday living and entertaining. The spacious living room serves as the heart of the home, featuring a stunning marble fireplace and seamless flow into multiple gathering areas, including a dedicated dining space just off the kitchen, a family room that leads to the outside and access to the bedrooms. The fully renovated chef’s kitchen is a true standout, showcasing soft-gray shaker cabinetry, quartz countertops, a Carrera marble backsplash, and stainless steel appliances. With ample counter space and a built-in water filtration system, this kitchen is as functional as it is beautiful. Throughout the home, you’ll find upgraded Italian wood-plank porcelain tile flooring, offering both durability and elegance. The primary suite provides a peaceful retreat with a walk-in closet and a fully updated ensuite bathroom featuring a double-sink vanity, granite countertops, and a spacious walk-in shower with marble and porcelain finishes. Step outside into your private backyard oasis. Designed for true Florida living, this space features a Pebble Tec pool, paver deck, covered gazebo with ceiling fan, a 65” outdoor TV, and a premium sound system perfect for entertaining or relaxing year-round. The lush landscaping, grassy area, and additional storage shed complete the outdoor experience. Additional highlights include a new roof (2019), A/C system (2021), WiFi-enabled irrigation system, fresh interior paint, and new LG washer, dryer, and dishwasher. Located in the desirable Dommerich area, just minutes from top-rated schools, dining, shopping, and major roadways, this home offers the perfect combination of location, upgrades, and lifestyle. This is the one you’ve been waiting for.

2130 Deloraine Trail, Maitland

$899,000
4 Beds 4 Baths Dommerich Hills SubDv. 32751 Zip Code
NEW PRICE…NEW OPPORTUNITY!! This beautiful, impeccably maintained and updated four bedroom and three and a half bath pool home absolutely has it all, including the added benefit of new electrical wiring throughout. Perfectly located in Maitland’s much sought after Dommerich neighborhood and walking distance to top rated elementary and middle schools. This attractive split-floor plan offers for spacious bedrooms and three full baths on the first level and a bonus room/5th bedroom with half bath on the second level. The gorgeous kitchen, boasts handsome, solid wood cabinets, granite countertops, and stainless steel appliances with double ovens. The first floor open layout includes a large dining area with brick fireplace leading into a wonderfully sized family room with fireplace and custom built-ins. Newly installed double pane, hurricane proof French doors brings in tons of natural light and leads out to your private oasis, including the newly resurfaced pool with new pool pump and filter, brick paver deck, open patio, and super fun gazebo with gas grill and nighttime lighting for entertaining! Awesome potential to install gas into the kitchen, as well. This home is fully supported by a new Generac system, never to be without power! Entire interior just freshly painted and new carpets installed in bedrooms and bonus room. Newer ROOF (2021), HVAC (2020) and tankless water heater. Samsung washer and dryer also included. Gorgeous architectural landscape with LED lighting add to its charm and warmth. This opportunity does not come along often and is absolutely MOVE-IN READY! Look forward to meeting you there!

2112 Chippewa Trail, Maitland

$299,000
2 Beds 2 Baths Sun Bay Club Condo SubDv. 32751 Zip Code
Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away.

1000 Winderley Place Unit 239, Maitland

$578,000
3 Beds 4 Baths Oakland Shores SubDv. 32751 Zip Code
Virtually Staged. Welcome to 502 Oak Lane in Maitland, a beautifully updated 3 bedroom, 3.5 bathroom pool home offering comfort, character, and peace of mind. Thoughtfully improved throughout, the home features fully updated plumbing, including the replacement of the original cast iron plumbing, along with a brand-new pool pump. Inside, you will find a well-designed layout with spacious living areas, updated finishes, and abundant natural light. Each bedroom has access to its own private bathroom, providing excellent privacy and flexibility for family members, overnight guests, or a home office. The home has been meticulously maintained and is truly move-in ready. Step outside to your private backyard oasis, complete with a swimming pool that is perfect for relaxing, entertaining, or enjoying Florida living year-round. Located on a quiet street in Maitland, the home is approximately 10 minutes from Winter Park and offers convenient access to major highways, shopping, dining, and everyday conveniences. This is a rare opportunity to own a fully updated pool home in one of Maitland’s most desirable and centrally located areas.

502 Oak Lane, Maitland