Location: Maitland, 32751
Do Not Show Listings
2130 DELORAINE TRL, MAITLAND, FL 32751
$850,0009 Days on yellowkey MLS ID: O6397018
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2175 Built: 1964 Tax: $10,394 (2025)Community: Highland Park Estates First AddSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,394
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: 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.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Mario Zendeli (407-325-3893)
790 S LAKE SYBELIA DR, MAITLAND, FL 32751
$975,00043 Days on yellowkey MLS ID: G5108209
REDUCED by $20,000 (2.0%) on 04/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2021 Built: 1958 Tax: $6,881 (2025)Community: Acreage & UnrecSingle Family
Taxes:$6,881
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Remarks: One or more photo(s) has been virtually staged. Rare opportunity to own a private 0.66-acre Estate homesite in Maitland with deeded Lake Sybelia access. 790 S Lake Sybelia Drive offers a unique combination of land, privacy, and lake rights in one of Maitland’s most desirable communities. Set on a secluded, no-HOA .66 acre's of land, the property includes 12 feet of lake frontage extending approximately 268 feet into Lake Sybelia, providing true and usable access. Private lake access you can actually use — without the $2M price tag. The updated home features 3 bedrooms and 2.5 bathrooms, a warm living room with a wood-burning fireplace, a panoramic window seat, and a spacious Florida room. Move in and enjoy as-is, or take advantage of the property’s full potential. This property is ideal for expansion, a second-story addition, pool, guest house, or a custom new build, offering flexibility rarely found in Maitland. The 0.66-acre lot is fully fenced with mature landscaping and provides ample space for outdoor living, entertaining, storing your RV or Boat. Opportunities combining large land for privacy and Lake Sybelia access are increasingly rare. Recent updates include: Roof (2019), AC (2023), insulation (2025), and updated electrical and plumbing. Ideally located near Lake Sybelia Park, the Iconic Enzian Theater, Maitland Art & History Center, Lake Lily Park, and just minutes to Winter Park and Downtown Orlando. Enjoy paddleboarding at sunrise or relaxing in your private backyard retreat — this property delivers a rare blend of space, privacy, and lake access in the heart of Maitland.
Listing is courtesy of: LISA REALTY PARTNERS (407-500-5472)
Listing Agent: Lisa Pownall (407-927-1698)
1440 LAKE SHADOW CIR #8305, MAITLAND, FL 32751
$197,5002 Days on yellowkey MLS ID: O6397395
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1048 Built: 2000Monthly Fee: $417 Tax: $2,886 (2025)Community: Visconti West CondoCondo
Taxes:$2,886
Elementary School: None
High School: None
Middle School: None
Remarks: 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.
Listing is courtesy of: INNOVATIVE REALTY, LLC (407-772-5555)
Listing Agent: Michael Rogers (407-782-3200)
2422 BRANCH WAY #100, MAITLAND, FL 32751
$115,0002 Days on yellowkey MLS ID: O6398992
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 550 Built: 1973Monthly Fee: $126 Tax: $1,408 (2024)Community: Carrington Park A CondoCondo
Taxes:$1,408
Tax Year: 2024
Remarks: 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!
Listing is courtesy of: MIAMI TANGO INVESTMENTS REALTY (786-464-8803)
Listing Agent: Moses Nae (407-499-0240)
1421 SUNNYSIDE DR, MAITLAND, FL 32751
$1,100,000146 Days on yellowkey MLS ID: O6358123
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2116 Built: 1966 Tax: $5,513 (2024)Community: Maitland Park SouthSingle Family
Taxes:$5,513
Remarks: One or more photo(s) has been virtually staged. HUGE PRICE IMPROVEMENT Welcome to 1421 Sunnyside Drive, Maitland, FL, a beautifully maintained 4-bedroom, 2.5-bath single-family home with a pool, located on a corner lot directly adjacent to Winter Park. While this home carries a Maitland address, it sits just steps from Winter Park homes, offering the best of both locations. This move-in-ready residence features thoughtfully designed indoor and outdoor living spaces and is zoned for the top-rated Dommerich Elementary School. From the moment you arrive, manicured landscaping and an inviting covered front porch create a warm first impression. Inside, natural light fills the home through skylights and bay windows, highlighting hardwood floors and a wood-burning fireplace. The open layout provides a seamless flow between living spaces, ideal for everyday living and entertaining. The chef’s kitchen serves as the heart of the home and features custom hardwood cabinetry, granite countertops, stainless steel appliances, a wine chiller, and a spacious breakfast island with ample seating. The kitchen opens to the main living areas, creating a functional and welcoming space. The primary suite offers a private retreat with wood floors and French doors leading directly to the porch. The ensuite bathroom includes an oversized shower with spa-style jets and customized storage. Three additional bedrooms and a full bathroom are located down a terrazzo-finished hallway and include custom upgrades. The dining area captures beautiful morning light through the bay window, while the living room features French doors that open to the outdoor living space. The private backyard oasis is designed for year-round enjoyment and includes a heated pool enclosed by a full screened deck and patio, creating a true indoor-outdoor lifestyle. Additional features include a custom built-in home office with abundant storage, a freshly refinished two-car garage, and an oversized driveway with a 30-amp electrical hookup for an RV or boat. The home has been freshly painted inside and out, includes new carpet, and reflects quality craftsmanship throughout. Enjoy quick access to Winter Park’s shops, dining, parks, and cultural offerings, along with the conveniences of Maitland living, making this home an exceptional opportunity in a highly desirable Central Florida location.
Listing is courtesy of: STRICKLAND REALTY GROUP INC (407-448-5068)
Listing Agent: Amanda Binns (407-448-5068)
781 GOLDWATER CT, MAITLAND, FL 32751
$860,00056 Days on yellowkey MLS ID: O6383680
REDUCED by $25,000 (2.8%) on 04/14/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2550 Built: 1970 Tax: $5,042 (2025)Community: Maitland Highlands DommerichSingle Family
Taxes:$5,042
Remarks: Exclusive Dommerich opportunity to own a true 5 Bedroom, 3 Bath home PLUS a dedicated office—an almost impossible combination to find in this celebrated neighborhood. Situated on a quiet, private-feeling cul-de-sac on over 1/3 acre, this home offers space, function, and timeless charm to love for years to come. This enclave of Dommerich is special - with neighbors often gathering and enjoying afternoons in Adirondack chairs neatly situated in front lawns, thanks to the serene nature of the streets. Even more charm is found in the front exterior of this home, which includes a front courtyard, perfect for gardening or a cup of coffee in the morning. Inside, the flexible floorplan includes formal living and dining rooms on the same wing as the primary retreat, plus a spacious den/office overlooking the pool on the opposite side of the home. The cozy family room features a fireplace and built-ins, and opens to a well-designed kitchen with granite counters, stainless steel appliances, bar seating, and a functional breakfast nook. Durable wood-look tile runs through the kitchen, family room, and roomy den for easy maintenance and enjoyment for years to come! Newer sliders provide great views and access to the sparkling pool from the den that could also make a great office or play space. The split bedroom layout provides privacy, with the primary suite in its own wing featuring a large walk-in closet, dual sinks in the renovated bathroom, and a spacious size that makes this suite truly feel like a retreat. On the guest bedroom wing of the home, the first two bedrooms share a remodeled Jack-and-Jill bathroom with each also having walk-in closets (yes, WALK-IN CLOSETS in guest bedrooms!). Bedrooms 4 and 5 share the 3rd Bathroom (ALSO REMODELED) that can easily function as a pool bath thanks to the tile floors that seamlessly flow through the guest hall. Storage abounds in this home with multiple hall closets, an indoor laundry room, plus an oversized garage for any sports or recreation equipment. Enjoy Florida living in the 20,000+ gallon pool with an expansive paver deck that extends along the side yard for additional entertaining space. This great backyard is low-maintenance thanks to the beautiful pavers, but a secluded yard space was saved for outdoor recreation or just enjoying the Dommerich neighborhood! Ideally located just across from top-rated Dommerich Elementary and Maitland Middle, savor a leisurely walk or bike ride to school daily. The home is also zoned for Winter Park High School! All easily accessible from Dommerich is Maitland Community Park featuring walking trails, fitness classes, and tennis; Maitland City Centre, known for its restaurants and festivals; renowned Winter Park and Park Avenue; and smooth access to all of Central Florida via nearby I-4. Move-in is easy thanks to major updates, including a full Roof Replacement in 2023, new exterior paint, an AC Replacement in 2021, a Replumb with PEX lines, sewer lines already connected with NO assestment fees, and no HOA. Don't miss this hard-to-find 5 Bedroom Dommerich home - you might be waiting YEARS for another chance like this!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Erin Baker (407-719-0030)
933 and 935 ROBINHOOD CT, MAITLAND, FL 32751
$599,900174 Days on yellowkey MLS ID: O6355207
REDUCED by $75,100 (11.1%) on 04/14/2026
Bed: 6 Bath: 0.0 Gar: 4 Liv Area Sq Ft: 2484 Built: 1979 Tax: $7,294 (2024)Community: OakwoodApartment
Taxes:$7,294
Remarks: 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.
Listing is courtesy of: KGV REALTY GROUP (407-474-0844)
Listing Agent: Olaf Stenger (407-325-4147)
2453 WORTHINGTON RD, MAITLAND, FL 32751
$585,000131 Days on yellowkey MLS ID: TB8454086
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1959 Built: 1966 Tax: $1,675 (2024)Community: English Estates Unit 3Spa: NoSingle Family
Taxes:$1,675
Remarks: A lovely well designed 4bdr. 2 bath home with an eat in kitchen open to a spacious family rm. A formal din.rm. and formal lvg.rm. are ready for any occasion. The long 2 lane brick driveway can accommodate multiple vehicles. Nearby schools for all levels and the amenities for recreation and entertainment are too numerous to list. This house should be added to your list when searching for your new home.
Listing is courtesy of: REALTY OF RIVERVIEW LLC (813-863-3948)
Listing Agent: Stephen Hachey (813-863-3948)
1275 LAKE SHADOW CIR #13107, MAITLAND, FL 32751
$179,90088 Days on yellowkey MLS ID: O6374698
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 672 Built: 2000 Tax: $2,194 (2024)Community: Visconti WestCondo
Taxes:$2,194
Middle School: Lockhart Middle
Remarks: Welcome home to this truly move-in-ready, beautifully updated 1-bedroom, 1-bath ground-floor condo located in the highly desirable Visconti West community in Maitland. This unit stands out from others of its size by offering upgrades and features that provide both comfort and peace of mind. From the moment you walk in, you’ll notice the new modern flooring throughout the living and bedrooms, creating a clean, updated look that flows seamlessly across the entire space. The kitchen has been completely refreshed and features a full suite of brand-new, high-efficiency appliances, including a built-in microwave, designed not only for style but also to help save money on your monthly utility bills. The home continues to impress with additional upgrades that are hard to find in comparable units, including a brand-new washer and dryer for added convenience. The bathroom has been fully updated with a sleek, modern design, featuring a step-in glass-enclosed shower that elevates the entire space. One of the standout features is the brand-new double pane glass window in the bedroom, offering enhanced insulation, reduced outside noise, and improved energy efficiency—another added benefit for comfort and cost savings. The open and functional layout provides a bright living space filled with natural light, while the private screened patio with additional storage offers the perfect place to relax or enjoy your morning coffee. What truly makes this property special is that no other unit of this size in the community offers this level of upgrades, modern finishes, and energy-efficient improvements. It’s a rare opportunity to own a condo where the big-ticket items have already been taken care of, allowing you to move in with confidence and peace of mind. Located in a gated, resort-style community with amenities including a pool, fitness center, basketball and tennis courts, playground, and beautifully maintained grounds, and just minutes from Winter Park, Downtown Orlando, Altamonte Springs, shopping, dining, and major highways—this home offers both lifestyle and convenience.
Listing is courtesy of: SHAWFIELD REALTY GROUP (407-963-7749)
Listing Agent: Carrie Sue Shawfield (407-963-7749)
320 WHITE OAK CIR, MAITLAND, FL 32751
$849,00034 Days on yellowkey MLS ID: O6390473
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2681 Built: 1973Monthly Fee: $31 Tax: $3,975 (2025)Community: Maitland GroveSingle Family
Taxes:$3,975
Remarks: ENTERTAINING MAITLAND GROVE POOL HOME. Step inside to discover oversized rooms, including a spacious great room overlooking the covered lanai and swimming pool in a private setting perfect for gatherings. Back yard includes a vinyl privacy fence, Pool resurfaced with Pebble Tec. Patio and pool decking have pavers with plenty of room for extra lounging. Lots of Room for everyone, including lIving Room, Dining Room and 4 bedrooms. Kitchen features all new SS appliances and sink w/ faucet, a separate breakfast room and laundry room. Primary room features en suite updated bathroom with dual vanity, shower, w/ tub, walk in closet and large slider doors overlooking the serene pool. Home offers lots of closet and ample storage. Extra Long driveway with side entry oversized garage includes utility sink. Home has been lovingly cared for. Call to view today!
Listing is courtesy of: OVERSTREET REAL ESTATE INC (407-595-5546)
Listing Agent: Susan Filebark (407-595-5546)
1501 DRUID ISLE RD, MAITLAND, FL 32751
$850,00030 Days on yellowkey MLS ID: O6389520
REDUCED by $25,000 (2.9%) on 04/14/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 3000 Built: 1971 Tax: $11,716 (2025)Community: Druid IsleSingle Family
Taxes:$11,716
Remarks: LAKESIDE LIVING in Maitland, Florida! Nestled canal front with direct access to Lake Charity, this vintage block home is built like a fortress with all the modern luxuries of today. A unique home for those who desire authenticity in both design and quality. A side entry garage leads to a courtyard like entrance with a marble path and asian influenced landscape. Double doors open into an expansive footprint with 3 large bedrooms, 2 baths and over 3,000 sq ft of living space. A 42 x 12 sunroom overlooking the water pays homage to the nostalgic Florida charm of this decade. No expense was spared when renovating this interior. Luxurious finishings and professional installation can make all the difference! Especially noted in the kitchen and baths! Upon entering, a Balsato Beige Porcelain fireplace surround wall anchors the space with plenty of areas to create conversational seating, a designer’s dream! The kitchen island is open to the entire living space with tons of storage and a double waterfall edge in Taj Mahal Quartzite. The perimeter counters are done in beautiful Bora Bora Quartz by Sharifstone. Real wood cabinetry in white dove compliments the earth tones giving a more transitional than modern vibe. Brushed gold hardware, lighting & plumbing fixtures are the perfect “jewelry” for the space! All new high end appliances convey. A brick fireplace graces the dining/living room wall (sounding like a song), yet another functional design opportunity to really create a home that works for YOU. There’s plenty of spots for an office, although not formally mentioned and the ability to use some of the square footage to create an additional “room” if needed. The primary suite closet takes the cake with all the fun features a dream closet should have! The ensuite bath has a lovely vanity with Quartz tops, dual sinks and a gorgeous shower with designer tile and a frameless glass door. Hardware is all in a matte black. The additional 2 bedrooms share a bath that has also had a complete remodel! This home is move in ready with a timeless style throughout. Flooring is a cohesive blend of tile and luxury vinyl plank. New roof 2024. With ideal proximity to fine dining & shopping in Maitland, Winter Park’s infamous Park Avenue and the Theme Parks, you’ll find yourself “staycationing” a little more often!
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Autumn Makin (352-455-0044)
1009 GROVE ST #1009, MAITLAND, FL 32751
$219,500174 Days on yellowkey MLS ID: O6353973
REDUCED by $5,500 (2.4%) on 04/03/2026
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1353 Built: 1972Monthly Fee: $483 Tax: $2,929 (2024)Community: Park Lake TownhousesCondo
Taxes:$2,929
Remarks: 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.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Ingrid Livingston (407-595-5972)
1404 STRATFORD RD, MAITLAND, FL 32751
$419,90042 Days on yellowkey MLS ID: O6387116
1 Days Off yellowkey (back on 3/13/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2473 Built: 1961Monthly Fee: $3 Tax: $5,107 (2024)Community: English Estates Unit 1Single Family
Taxes:$5,107
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Spacious one-story home featuring 4 bedrooms and 2.5 bathrooms with a functional, open layout. The kitchen offers a convenient breakfast bar overlooking the dining area. Step outside to enjoy the screened-in back porch and private in-ground pool, perfect for relaxing or hosting gatherings. The wood-fenced backyard provides added privacy, and the 2-car garage offers ample storage and parking. A fantastic opportunity with great indoor and outdoor living space!
Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)
Listing Agent: Eva Hockenberry (800-583-2914)
310 WHITE OAK CIR, MAITLAND, FL 32751
$849,00090 Days on yellowkey MLS ID: O6373919
1 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2995 Built: 1973Monthly Fee: $35 Tax: $7,779 (2025)Community: Maitland Grove Unit 1Single Family
Taxes:$7,779
Remarks: Under contract-accepting backup offers. Welcome home to one of the established Maitland neighborhoods in a pristine location close to everything, Maitland Groves. A lovely brick walkway invites you up to a charming entrance with a bricked front porch. A four- or five-bedroom, four-bath home features nearly 3,000 square feet with a generous flex space, checks all the boxes. The spaces have been opened with living spilling into dining and a bay window adding charm to an ideal gathering room to entertain in. Custom tile throughout for seamless design with an abundance of light making the spaces inviting and easy to relax in. Kitchen is updated with custom 42-inch wood cabinets, custom moldings, stainless appliances with new dishwasher, gas range and oven, granite counters with counter seating, and unbelievable storage and cabinet space. Florida room spans the back of the house with a bricked floor, a wet bar and a dedicated office/bedroom. Updated primary bedroom with a large walk-in closet. Main bath with dual sinks and new rainfall shower heads, tower storage cabinets, seamless glass with walk-in shower, stone floor and custom tile. Outside patio enjoys a paver deck with large Florida pool and plenty of green space with room to grow. Other updates include roof (2021), solar energy system so energy bills are low, recently painted in select areas, wood laminate floors in all bedrooms, renovated second and third baths, spacious indoor laundry and mudroom for organization, fenced yard, recessed lighting in living spaces, re-plumbed, plantation shutters, 2021 pool pump, pool converted to saltwater system and new garage door. If you need space, this has it. Terrific schools, close to Interstate 4, downtown Maitland which is home to Lake Lily with a weekly farmers market, independently owned Enzian Theatre, world-class restaurants and fantastic community parks home to many community events.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
2801 WAUMPI TRL, MAITLAND, FL 32751
$879,00024 Days on yellowkey MLS ID: S5146322
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2836 Built: 1972 Tax: $305 (2024)Community: Dommerich Hills 6Th AddSingle Family
Taxes:$305
Remarks: Welcome to Dommerich Hills! This fully renovated property delivers clean modern design with real functionality with NO HOA with a paver driveway, and double-door entry set the tone from the start. Inside, a bright open layout is anchored by a statement kitchen featuring sleek cabinetry, stainless steel appliances, and a waterfall island with custom wood detailing. The bathrooms follow with spa-inspired finishes, glass-enclosed showers, and modern fixtures throughout. Step outside to a covered lanai overlooking a private pool and expansive paver patio built for true Florida indoor outdoor living. Move in ready and designed to stand out, Located just minutes major highways, premium shopping, dining, and entertainment, this home delivers convenience and lifestyle all in one to the city beautiful. call to make a appointment to see this amazing Home.
Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)
Listing Agent: Javin Lopez (407-873-6606)
344 BANYAN DR, MAITLAND, FL 32751
$398,0006 Days on yellowkey MLS ID: O6397900
1 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1408 Built: 1972 Tax: $1,336 (2024)Community: Druid Hills ParkSingle Family
Taxes:$1,336
Elementary School: Sabal Point Elementary
Remarks: STUNNING MODERN REVIVAL IN THE HEART OF MAITLAND. Welcome to 344 Banyan Drive, where classic Maitland charm meets contemporary elegance. Experience the pinnacle of move-in-ready luxury at 344 Banyan Dr. This impeccably renovated residence has been transformed from top to bottom with sophisticated finishes and meticulous attention to detail. The open-concept interior shines with all-new flooring, contemporary baseboards, and a fresh, designer paint palette. The newly renovated kitchen is a true showstopper, boasting new custom cabinetry, sleek stone countertops, a stylish tile backsplash, and a premium stainless steel appliance package. Both the living spaces and the fully renovated bathrooms feature all-new designer lighting that creates a warm, inviting ambiance throughout. Every inch of this home feels brand new. Don't miss your chance to own a masterpiece in 32751!
Listing is courtesy of: REMAX SUNSTATE REALTY (416-450-7436)
Listing Agent: Ketan Patel (416-508-9037)
220 ALPINE DR, MAITLAND, FL 32751
$450,00042 Days on yellowkey MLS ID: O6388051
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 988 Built: 1953 Tax: $5,537 (2024)Community: Sunset RidgeSingle Family
Taxes:$5,537
Remarks: Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same family since the 1960s, is ideally located near shopping, dining, parks, and major roadways, providing convenient access throughout Central Florida. The property offers potential for renovation, expansion, or redevelopment, with a lot that provides space for future improvements. Ideal for homeowners, builders, or investors seeking a property in a desirable and established area. The adjacent property to the west (210 Alpine) is also available for purchase. Contact the listing agent for additional information and pricing on the neighboring parcel.
Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)
Listing Agent: Beth Hathaway (407-314-1300)
1994 KENASTON RD #1994, MAITLAND, FL 32751
$415,00090 Days on yellowkey MLS ID: O6374243
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2103 Built: 1982 Tax: $4,582 (2025)Community: Ultra Vista CondoSpa: NoCondo
Taxes:$4,582
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: Located in the desirable city of Maitland, just three miles from Winter Park’s renowned Park Avenue, this extensively updated 3-bedroom, 3.5-bath townhouse offers modern living in a prime Central Florida location. Tucked within a quiet residential setting and zoned for highly rated Seminole County schools, the home provides easy access to dining, shopping, and entertainment while maintaining a sense of privacy and comfort. The thoughtfully designed layout offers flexibility and convenience across two levels. The main floor features a spacious primary bedroom complete with a walk-in closet and private bathroom. Also on the first level is a welcoming living area with vaulted ceilings, creating an open and airy feel, along with a dining space that looks out through French doors. The kitchen is well-appointed with stainless steel appliances, stone countertops, and ample workspace, making it ideal for everyday living and entertaining. A screened rear porch extends the living space outdoors, perfect for relaxing or enjoying Florida evenings. Upstairs, you’ll find a second primary bedroom with an attached bathroom, offering a private retreat for guests or multi-generational living. A third bedroom, also with its own bathroom, is located just off a landing that overlooks the living area below, adding architectural interest and an open-concept feel. Significant updates completed in 2024 enhance both comfort and long-term value, including a new roof, upgraded air conditioning system with a 10-year manufacturer warranty, fully updated plumbing, and modern electrical improvements with new breaker boxes, switches, and receptacles. Interior finishes include wood flooring on the main level, luxury vinyl plank flooring upstairs, tile in wet areas, energy-efficient Low-E double-pane windows, recessed LED lighting throughout, and updated fixtures in the kitchen and closets. The exterior was freshly painted in 2025, adding to the home’s curb appeal and move-in-ready condition. With its low-maintenance design, versatile floor plan, and unbeatable location near Winter Park’s Park Avenue and the scenic Chain of Lakes, this home presents
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Veronica Figueroa (407-519-3980)
1529 GLASTONBERRY RD, MAITLAND, FL 32751
$525,00042 Days on yellowkey MLS ID: O6387618
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1655 Built: 1970Monthly Fee: $3 Tax: $5,753 (2024)Community: NorthgateSingle Family
Taxes:$5,753
Remarks: Under contract-accepting backup offers. Welcome to 1529 Glastonberry Rd, a 4 bedroom, 2 bath pool home in the heart of Maitland. You will love this tastefully updated home. Upon entering, you will love the open floor plan and the way the homes flows from the spacious living room to the airy dining room straight into the bright, sparkling kitchen with stainless steel appliances. The whole area overlooks the inviting salt water pool and enclosed lanai. It's a dream space for entertaining. The primary overlooks the pool with a separate entrance, an updated bath and walk in closet. With three other great sized rooms, there is plenty of room and storage. Located in vibrant Maitland, shopping, restaurants, entertainment and night life are close.
Listing is courtesy of: RE/MAX TOWN CENTRE (407-996-3200)
Listing Agent: Tamara Rorman (407-491-1642)
2466 FIELDINGWOOD RD, MAITLAND, FL 32751
$599,0006 Days on yellowkey MLS ID: O6396883
0 Days Off yellowkey (back on 4/12/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1765 Built: 1972 Tax: $1,712 (2024)Community: English WoodsSpa: NoSingle Family
Taxes:$1,712
Remarks: 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.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kristine Mckinley (407-415-2412)
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