Location: Maitland , 32751
Do Not Show Listings
624 TUSCARORA TRL, MAITLAND, FL 32751
$945,00021 Days on yellowkey MLS ID: O6418744
1 Days Off yellowkey (back on 6/30/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3370 Built: 1961 Tax: $5,322 (2025)Community: Dommerich HillsSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,322
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Under contract-accepting backup offers. Welcome to this impressive 5-bedroom, 3-bath split-level POOL home in desirable Dommerich Hills, perfectly nestled on a generous 0.34-acre lot backing to a quiet creek and scenic green space.. Enjoy exceptional privacy and natural beauty with no rear neighbors, creating a peaceful backyard retreat. This remarkable residence offers almost 3400 square feet of living space, providing plenty of room for family living and entertaining. Thoughtfully designed, the home features expansive gathering areas, comfortable bedrooms, and inviting indoor-outdoor living spaces that take full advantage of the beautiful backyard setting. The stunning living room showcases cathedral ceilings with beautiful tongue-and-groove wood detailing, wood burning fireplace creating a warm and inviting atmosphere. French doors open to an expansive outdoor deck overlooking the large backyard and sparkling pool, seamlessly blending indoor and outdoor living. The well-equipped, efficient kitchen is designed for both everyday living and entertaining; appointed with custom shaker cabinetry, granite surfaces, and premium stainless steel appliances serves as the heart of the home. The kitchen boasts a separate breakfast room, with a large picture window capturing beautiful views of the backyard and pool, filling the space with natural light. The oversized primary suite serves as a private retreat, featuring French doors that open to the outdoor deck, an updated en-suite bath, and a large walk-in closet. The secondary bedrooms and guest bath on this level are generously sized and offer ample closet space, providing comfort and flexibility for family members or guests. Downstairs features a spacious family room with a cozy fireplace, two bedrooms, a full guest bath, and a convenient laundry room PLUS wonderful storage room. French doors open to a charming brick terrace overlooking a beautifully manicured backyard that backs onto a peaceful creek. The outdoor space also includes a large swimming pool and a life-size chess/checkerboard area, creating an ideal setting for relaxation and family fun! Recent improvements include windows replaced (2008, 2009), travertine and wood flooring, roof replaced in 2020, A/C' dates2022/2007, freshly painted exterior, and a new sewer connection completed in 2025. A detached two-car garage and long driveway provide abundant parking space, easily accommodating multiple vehicles and making it ideal for guests, recreational vehicles, or a growing family. Ideally located just a short bike ride from highly regarded Dommerich Elementary and Maitland Middle School. Conveniently located just minutes from downtown Maitland, Winter Park, premier shopping, dining, and major roadways, providing easy access to everything Central Florida has to offer. This one-of-a-kind property combines space, privacy, character, and convenience in one remarkable package. Schedule your private showing today and experience all this exceptional home has to offer.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Mary Colton (407-222-7388)
245 ORANGE PL, MAITLAND, FL 32751
$675,00023 Days on yellowkey MLS ID: O6419510
3 Days Off yellowkey (back on 6/29/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1935 Built: 1946 Tax: $10,093 (2025)Community: Orangedale Park RepSingle Family
Taxes:$10,093
Remarks: Under contract-accepting backup offers. Location, location!! Discover a rare opportunity to own a single family home plus 2 ADUs, just steps from the iconic Enzian Theater and vibrant Downtown Maitland. This property features three separate units, each with three separate electric meters, water meters and IN-UNIT washer and dryers - a highly sought-after feature for both tenants and owner-occupants alike.With all exterior siding replaced in 2026 on all three units, newer roofs installed in 2026 and 2021, and updated kitchens already completed, this property offers an exceptional turnkey investment with major improvements already in place for long-term peace of mind. This property also has ample parking and an oversized storage shed. The main house is a spacious 2 Bed/1 Bath unit (currently rented for $1,950/month), Unit 2 is a 1 Bed/1 Bath rented for $1,500/month, and Unit 3 is a studio rented for $1,100/month. Current rents are currently below market value and all three units are occupied by long-standing tenants who provide dependable income and minimal turnover. All three leases are set to expire in July and August of 2026, providing future flexibility for an investor or owner-occupant, and two of the tenants have already indicated interest in extending their leases, offering continued income stability from day one. Whether you’re looking to expand your investment portfolio, take advantage of a house-hacking opportunity, or explore the potential for short-term rental income, this property offers exceptional versatility in one of Central Florida’s most sought-after locations. Live in one unit while generating income from the others, or maximize returns through a strategic blend of long-term and short-term rental options. Location truly sets this property apart. Enjoy being just minutes from Winter Park Village, offering endless shopping, dining, entertainment, and a movie theater, while also being a short drive from the charm and excitement of Park Avenue and everything Winter Park has to offer. Residents will love easy access to weekend farmers markets in both Maitland and Winter Park, nearby grocery stores, top-rated restaurants, local boutiques, and convenient commuter routes. The property is also located near Rollins College, adding even more appeal to the location.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Jessica Lee (773-313-5099)
551 RUFFEL ST, MAITLAND, FL 32751
$278,500106 Days on yellowkey MLS ID: S5146986
REDUCED by $21,400 (7.1%) on 06/29/2026
Bed: 3 Bath: 1.5 Liv Area Sq Ft: 1162 Built: 1970 Tax: $396 (2025)Community: Clark Homes AcresSpa: NoSingle Family
Taxes:$396
High School: Edgewater High
Remarks: Situated at the end of a cul-de-sac in the Eatonville/Maitland area, this home offers a great opportunity for a first-time buyer or someone looking to downsize. According to the owner, the property was rehabilitated by the county in 2017, with updates that included the HVAC, plumbing, and electrical systems, and the roof was replaced approximately 10 years ago. Conveniently located near I-4 and Winter Park, this home is just minutes from local eateries, the library, and public transportation.
Listing is courtesy of: RESIDENTIAL MATCHMAKERS LLC (407-286-1698)
Listing Agent: Buffy Barrott (321-332-4503)
1440 LAKE SHADOW CIR #8305, MAITLAND, FL 32751
$184,95093 Days on yellowkey MLS ID: O6397395
REDUCED by $5,050 (2.7%) on 06/29/2026
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)
1000 WINDERLEY PL #239, MAITLAND, FL 32751
$299,000106 Days on yellowkey MLS ID: O6395472
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1164 Built: 1982Monthly Fee: $523 Tax: $489 (2025)Community: Sun Bay Club CondoSpa: NoCondo
Taxes:$489
Elementary School: Lake Sybelia Elem
Middle School: Lockhart Middle
Remarks: 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.
Listing Agent: Nancy Bagby (407-620-8868)
220 ADAMS DR, MAITLAND, FL 32751
$1,995,00042 Days on yellowkey MLS ID: O6413737
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3005 Built: 1977 Tax: $15,563 (2025)Community: Kings RowSpa: NoSingle Family
Taxes:$15,563
Remarks: Welcome to 220 Adams Drive — a breathtaking, completely remodeled single-story masterpiece nestled in the heart of Maitland's coveted Kings Row neighborhood. Thoughtfully reimagined from the studs out with exquisite craftsmanship and elevated design, this stunning home offers 4 bedrooms, a dedicated private office, 3.5 baths, and over 3,000 square feet of refined living on a fully fenced, oversized lot. The renovation is truly comprehensive — all-new plumbing, electrical, ductwork, and three separate AC units provide complete peace of mind. Spray foam insulation delivers exceptional energy efficiency, propane gas powers the chef's kitchen cooktop and tankless hot water heater, and Lutron touch-slide dimmers indoors plus automated Lutron outdoor lighting give the home a level of sophistication and control that is rarely found at any price. French drains round out a property that has been engineered as thoughtfully as it has been finished. Step through a charming covered front porch and into a bright, open-concept interior where elevated ceilings, rich wood floors, and designer recessed lighting create an effortlessly elegant atmosphere. The chef's kitchen is a showstopper — outfitted with high-end appliances including a gas cooktop, custom white cabinetry, clever appliance garages, and bespoke built-ins that marry beauty with function. The warm and inviting living room anchors the home with a wood-burning fireplace and seamless sliding doors to the pool beyond. The split-bedroom layout offers exceptional privacy for every member of the household. The oversized primary suite features a spa-inspired en suite with a double-sink vanity, walk-in glass shower, and soaking tub — plus a large walk-in closet with custom built-ins. The second bedroom enjoys its own private en suite with a walk-in shower, perfect for guests or multi-generational living. Bedrooms three and four share a well-appointed hall bath with a tub/shower combination. Outside, your private resort awaits. The saltwater pool with sunshelf is the perfect centerpiece, framed by a covered cabana with fireplace and a fully equipped outdoor kitchen. The Lutron automated lighting system extends seamlessly to the exterior, creating effortless ambiance day and night. The fully fenced yard offers privacy and room to breathe. The property features a two-car garage and a separate one-car garage — both finished with epoxy floors. The one-car garage is currently appointed as a private home gym with an adjacent storage room, offering flexible utility from day one. Located in a quiet, tucked-away neighborhood with a community park and playground, this home is just minutes from Winter Park, Park Avenue, the Winter Park Racquet Club, and scenic parks and trails. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High School. Homes of this caliber — fully rebuilt, impeccably finished, with every system new — are extraordinarily rare. Schedule your private showing today.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
1100 LAKE SHADOW CIR #2307, MAITLAND, FL 32751
$190,00086 Days on yellowkey MLS ID: S5148098
REDUCED by $10,000 (5.0%) on 06/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1111 Built: 2000 Tax: $3,059 (2025)Community: Visconti WestCondo
Taxes:$3,059
Remarks: 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.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Jodi Lambiase (407-848-0847)
892 PARK LAKE CIR #69, MAITLAND, FL 32751
$225,00050 Days on yellowkey MLS ID: O6411386
REDUCED by $4,000 (1.7%) on 06/23/2026
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1353 Built: 1972 Tax: $3,327 (2025)Community: Park Lake TwnhsTownhouse
Taxes:$3,327
Remarks: Maitland's Hidden Gem! Discover comfort, style, and convenience in this BEAUTIFULLY MAINTAINED 2-bedroom, 1.5-bath condo in the desirable Park Lake Townhouses community of Maitland with NEW A/C 2026 and NEW Water Heater 2026. Located minutes from Park Ave, Trader Joes, Lifetime Fitness and all Winter Park/Maitland has to offer! Offering the FEEL OF A TOWNHOME with two spacious levels, a private patio, and a one-car garage, this home is tucked away in a QUIET LOCATION with PEACEFUL GREEN SPACE VIEWS from the front. Step inside to find EASY-CARE TILE FLOORING throughout the main level and a bright, welcoming Living Room filled with NATURAL LIGHT from the large front window. A convenient half bath and SPACIOUS CLOSET are located just off the hallway before the home opens into the Dining and Kitchen areas. Perfect for both everyday living and entertaining, the Dining area features sliding glass doors leading to a PRIVATE FENCED PATIO, creating a wonderful outdoor space for morning coffee, grilling, or relaxing evenings. The patio also provides direct access to the ATTACHED ONE-CAR GARAGE. Just off the Dining area, you'll find a DEDICATED LAUNDRY ROOM complete with an included washer and dryer. The beautiful Kitchen is sure to impress with its abundance of cabinetry, GRANITE COUNTERTOPS, stainless steel appliances, CHIC TILE BACKSPLASH, and center island that adds both functionality and style. Upstairs, two generously sized bedrooms provide comfortable retreats. The Primary Bedroom features ATTRACTIVE HARDWOOD FLOORING, while the second bedroom is carpeted for added comfort. Both bedrooms offer DOUBLE MIRRORED CLOSET DOORS and share a well-appointed en suite bath. FROSTED GLASS-PANELED INTERIOR DOORS throughout the home add a modern and distinctive touch. Adding even more value and peace of mind, the home features a NEW AC SYSTEM and NEW WATER HEATER. Residents of Park Lake Townhouses enjoy a SPARKLING COMMUNITY POOL along with HOA-covered trash collection, lawn care and exterior maintenance, including the roof, making for a LOW-MAINTENANCE LIFESTYLE. Ideally located, you're just minutes from the boutiques, restaurants, and cafés of PARK AVENUE IN WINTER PARK, as well as CULTURAL DESTINATIONS such as Rollins College, Morse Museum of American Art, and Winter Park Scenic Boat Tour. Nearby shopping, dining, and entertainment options abound at MAITLAND CITY CENTRE, while commuters will appreciate EASY ACCESS to I-4, SR 414, and downtown Orlando. With its STYLISH UPDATES, private outdoor space, attached garage access, and EXCEPTIONAL LOCATION near some of Central Florida's most beloved destinations, this CHARMING residence is ready to welcome you home. Act quickly—this GEM won't last long!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
791 SEQUOIA TRL, MAITLAND, FL 32751
$939,000316 Days on yellowkey MLS ID: O6340919
REDUCED by $56,000 (5.6%) on 06/28/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4144 Built: 1961 Tax: $4,128 (2024)Community: Dommerich WoodsSpa: NoSingle Family
Taxes:$4,128
Tax Year: 2024
Remarks: Discover a rare opportunity in Dommerich Woods, a distinguished and established Maitland neighborhood celebrated for its rich heritage. Situated on .33 acre of lushly landscaped grounds, this remarkable property welcomes with paver drive and enjoys a tranquil setting along a peaceful creek connecting Lake Minnehaha and Lake of the Woods - creating an atmosphere of natural elegance and privacy. Re-roofed in 2023, this expansive 5 bedroom, 3 1/2 bath residence offers 4,144 HSF, and WHOLE HOUSE WATER SOFTNER, showcases a versatile TWO-LEVEL design, perfectly suited for refined living and gracious entertaining. The main level opens with a foyer leading into a bright, open living and dining area, where CEILING FANS throughout the main level add comfort and elegance. From here, step out onto the COVERED UPPER DECK with sweeping views of the SCREENED POOL, TROPICAL GARDEN, and serene backyard retreat - an ideal setting for morning coffee or evening gatherings. At the heart of the home, the GOURMET KITCHEN blends style and functionality with SOLID WOOD CABINETRY, a built-in WINE REFRIGERATOR and WINE RACK, granite countertops, and a CENTER ISLAND with SEATING, and REVERSE OSMOSIS WATER SYSTEM under the DOUBLE SINK. The adjacent laundry room offers exceptional storage, keeping household essentials organized. For added convenience , a two-car garage with built-in cabinets and workshop area, adjoins the spacious laundry room that has granite counters and washer and dryer. Also on the main level , adjacent to the primary bedroom with en-suite bath, a bedroom has been thoughtfully converted into a large closet featuring a CUSTOM CLOSET system, providing abundant space for wardrobe organization. Both levels feature inviting WOOD-BURNING FIREPLACES that add ambiance to the living spaces. On the lower level, a spacious family room, kitchenette, study/library/office, two bedrooms, full bath and half bath provide the perfect complement to easy living. Along the hallway, built-in wood shelving creates a refined showcase for books, art, or personal collections. While one bedroom includes a custom built in desk- ideal for work or study, a second bedroom adds flexibility for creative projects. This level opens onto the screened pool and patio area, designed for seamless indoor-outdoor living. Outside, tropical plantings, METERED IRRIGATION, and a winding private walkway leads along the soft murmur of the BORDERING CREEK. An added bonus is the storage room located below the kitchen which is approximately 375 sq.ft. Whether hosting guests or enjoying a quiet evening, this private oasis offers the ultimate backdrop for relaxed Florida living. Enjoy the opportunity to join the Dommerich Beach Civic Association with membership options including access to a private picnic area, boat ramp, canoe and kayak storage, and unforgettable evening sunsets. With its rare combination of design, flexible spaces, and an idyllic setting , this residence presents a unique opportunity to experience the very best of Maitland and Central Florida living. All this is convenient to some of Central Florida's finest schools, shopping, restaurants, parks, entertainment, businesses and more!
Listing is courtesy of: VANWORMER REALTY & DEVELOPMENT (407-927-1304)
Listing Agent: David Vanwormer (407-927-1304)
1507 GROVE ST, MAITLAND, FL 32751
$231,00044 Days on yellowkey MLS ID: O6412094
REDUCED by $4,000 (1.7%) on 06/10/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1256 Built: 1979Monthly Fee: $450 Tax: $1,550 (2025)Community: Park Lake Villas CondoCondo
Taxes:$1,550
Remarks: Welcome home to this beautifully maintained 3 bedroom, 2 bath, one-story condo offering 1,256 square feet of comfortable living space in one of Central Florida's most sought-after school districts, zoned for Dommerich Elementary and Maitland Middle School. This move-in-ready home features significant recent upgrades, including a brand-new roof (2024) , new HVAC system (2024), and new Electrical panel (2026), providing peace of mind and energy efficiency for years to come. Inside, you'll find a functional floor plan with spacious living and dining areas, generous bedrooms, and abundant natural light throughout. Step outside to your large, private, fully fenced back patio, ideal for entertaining, relaxing, or enjoying outdoor living. The patio offers direct access to the community pool, making it easy to enjoy Florida's year-round sunshine. Ideally located near shopping, dining, and major roadways, this home combines low-maintenance living with top-rated schools and outstanding community amenities.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ingrid Livingston (407-595-5972)
219 QUAYSIDE CIR, MAITLAND, FL 32751
$850,000274 Days on yellowkey MLS ID: O6352851
REDUCED by $45,000 (5.0%) on 06/19/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1459 Built: 1985 Tax: $6,212 (2024)Community: The MooringsCondo
Taxes:$6,212
Remarks: Every so often, a property comes along that redefines what lake living can be, and this is that home. Thoughtfully reimagined from top to bottom, this two-bedroom, two-and-a-half-bath residence blends refined design with the effortless lifestyle of the Winter Park Chain of Lakes. Go inside to discover a fully renovated interior anchored by a showstopping 14-foot Cambria quartz waterfall island, the heart of a kitchen designed for entertaining and everyday luxury. The GE Monogram and Café appliance suite, paired with custom solid wood, soft-close cabinetry, makes every detail feel bespoke. Natural light fills the living spaces through PGT double-pane insulated windows and Andersen French doors, framing tranquil garden views that create a sense of calm and privacy. Upstairs, two spacious bedroom suites offer comfort and style, each crafted with high-end finishes and thoughtful touches throughout. Beyond the walls, enjoy the rare privilege of a dedicated boat slip on Lake Maitland, Winter Park’s largest and sought-after body of water. Cruise the connected lakes, explore the historic canals or simply unwind at sunset, all just near home. Built in 1985 and completely transformed with modern systems, including a 2023 HVAC and water heater, this residence offers peace of mind to match its beauty. A one-car garage adds convenience, while every finish reflects care, quality and craftsmanship. Here, luxury isn’t just found inside, it’s a way of life, lived by the water.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Chad Isenhart (407-955-0033)
9001 LAKE CHARITY DR, MAITLAND, FL 32751
$575,00070 Days on yellowkey MLS ID: O6405361
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1623 Built: 1958 Tax: $1,937 (2025)Community: Druid Hills EstsSingle Family
Taxes:$1,937
Remarks: Welcome to a rare opportunity in the beautiful neighborhood of Druid Hills in Maitland—this charming single-family home is on the market for the first time in 45 years. Built with solid block construction, this home offers exceptional durability, structural soundness, and reliable weather resistance, giving peace of mind for years to come. Situated on an expansive and highly desirable corner lot, the property provides a unique blend of privacy, space, and long-term potential. With .41 acres of land, this double lot offers endless possibilities, whether you’re looking to enjoy the generous yard or explore the option to split it into two separate parcels. Inside, the home features 3 bedrooms and 2 bathrooms across 1,623 square feet of thoughtfully designed living space. A spacious layout provides comfort and functionality, while large windows invite in natural light, creating a warm and welcoming atmosphere throughout. The 2-car garage offers ample storage and convenience, complementing the home’s practical appeal for everyday living. Outside, the oversized lot is truly the standout feature—lush, open, and full of potential for outdoor living, expansion, or future development. With its prime location, generous lot size, and first-time availability in decades, this is a one-of-a-kind opportunity you won’t want to miss.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Joseph Sipp (407-820-7016)
320 WHITE OAK CIR, MAITLAND, FL 32751
$799,000125 Days on yellowkey MLS ID: O6390473
1 Days Off yellowkey (back on 6/27/2026)
REDUCED by $26,000 (3.2%) on 06/23/2026
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: Under contract-accepting backup offers. 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)
933 and 935 ROBINHOOD CT, MAITLAND, FL 32751
$549,000265 Days on yellowkey MLS ID: O6355207
0 Days Off yellowkey (back on 6/24/2026)
REDUCED by $50,900 (8.5%) on 06/10/2026
Bed: 6 Bath: 0.0 Gar: 4 Liv Area Sq Ft: 2484 Built: 1979 Tax: $7,294 (2024)Community: OakwoodApartment
Taxes:$7,294
Remarks: 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.
Listing is courtesy of: KGV REALTY GROUP (407-474-0844)
Listing Agent: Olaf Stenger (407-325-4147)
614 BROOKWOOD LN, MAITLAND, FL 32751
$899,00062 Days on yellowkey MLS ID: O6408295
REDUCED by $26,000 (2.8%) on 06/24/2026
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 3485 Built: 1968 Tax: $2,836 (2024)Community: Forest BrookSpa: NoSingle Family
Taxes:$2,836
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: JUST REDUCED - Welcome to this meticulously updated, one-story masterpiece situated on a sprawling, professionally landscaped 1/3-acre lot. This 5-bedroom, 3.5-bath sanctuary plus bonus room seamlessly blends high-end design with modern efficiency. At the heart of the home lies an extra-large gourmet kitchen designed for the serious chef, featuring double ovens, dual microwaves, and two dishwashers. The culinary space flows effortlessly into an impressively large dining room, while the living room offers a cozy retreat centered around a classic wood-burning fireplace, perfect for crisp winter mornings. The interior has been refreshed with a brand-new neutral paint palette that complements the fully updated bathrooms and high-end finishes found throughout. Outside, the large fully fenced backyard serves as a private oasis, boasting a stunning pool and ample space for grand-scale entertaining. A massive storage shed, equivalent in size to a full garage bay, conveys with the property to provide incredible storage or workshop potential. This home offers ultimate peace of mind with significant mechanical upgrades, including a 2021 AC unit, 2019 water heater, 2013 roof, and a new pool pump, new interior doors throughout and new door hardware as well Also Plantation Shutters throughout. Sustainability meets savings with a solar panel system that slashes the electric bill to approximately $50 a month for this expansive home. Whether you are seeking a fabulous primary residence, vacation home or a high-performing investment property, that can also be rented as a short -term rental/Airbnb this is the home for you. Available furnished or unfurnished. Garage was converted to a bonus room and laundry with a ½ bath and a small second kitchen. It can easily be converted back to a garage. HUGE STORAGE SHED IN SIDE YARD EQUAL TO A ONE CAR GARAGE. Well water used for in ground sprinklers, a huge savings on your water bill. This rare find delivers the space, privacy, and modern luxury today’s buyers demand. Near everything including Whole Foods, Trader Joes, Great Winter Park- Park Ave Shopping, Dining and galleries.
Listing Agent: Gale Milgrim (407-443-9832)
195 CEDARWOOD DR, MAITLAND, FL 32751
$800,00028 Days on yellowkey MLS ID: O6418229
0 Days Off yellowkey (back on 6/23/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1941 Built: 1958 Tax: $2,492 (2025)Community: Lakewood Shores 1St AddSingle Family
Taxes:$2,492
Remarks: Under contract-accepting backup offers. Nestled on the shores of skiable Lake of the Woods, this beautifully maintained 3-bedroom, 2 and a half bath waterfront residence offers over 105 feet of private lake frontage with breathtaking open-water views. Designed for those who embrace the lake lifestyle, the property features a private boat launch, two docks, and a solar-powered boat lift, providing effortless access to one of Central Florida's most desirable private lakes. Inside, vaulted ceilings and abundant natural light create an inviting atmosphere, while the updated kitchen opens seamlessly to the living and dining spaces, making everyday living and entertaining a pleasure. The primary suite enjoys peaceful water views, and the home's coastal-inspired finishes enhance the relaxed lakefront setting. A spacious rear deck overlooks the water and serves as the perfect place to enjoy sunrise coffee, sunset gatherings, and weekends on the lake. Additional highlights include a durable metal roof, wood floors, mature landscaping, generous outdoor living spaces, and a prime Maitland location convenient to shopping, dining, top-rated schools, Winter Park, and Downtown Orlando. Rarely does an opportunity arise to own a move-in ready waterfront home with this combination of frontage, amenities, and direct access to skiable waters.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Chase Tate, Pllc (217-899-2619)
653 GREEN MEADOW AVE, MAITLAND, FL 32751
$495,00076 Days on yellowkey MLS ID: O6402661
REDUCED by $23,000 (4.4%) on 06/23/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1909 Built: 1970 Tax: $1,992 (2024)Community: Forest Brook 3Rd SecSingle Family
Taxes:$1,992
Remarks: One or more photo(s) has been virtually staged. Seller Motivated. Location, Location, Welcome to your new 4 BED 2 BATH home tucked away on a quiet cul-de-sac street in the desirable Maitland community of "Forest Brook" This one-of-a-kind home offers the perfect blend of charm, space, and functionality. Lovingly maintained, the home welcomes you with a grand Foyer, Formal Living and Dinng rooms, open family room, ideal for gatherings. A new updated Chef's Kitchen, complete with a gas range, beautiful Cherry cabinets, new appliances, and new Quartz countertops. The spacious Florida Room has a fun step up bar with pass through access to the kitchen. Perfect for entertaining and offers its own AC/Heater unit. Step outside to the large wrap around Deck. Tons of space for outdoor entertaining. No neighbors behind you, just tons of conservation space. Additional upgrades include Roof-2021, AC-2023-Fl Room, AC-2025, Gas Water Heater-2010, Kitchen appliances 2023, Electrical panel- 2024. This home is ideally located just minutes from Winter Park, Casselberry, Winter Springs, Easy access to shopping, dining, and major commuter routes. Start living your Best Life.
Listing is courtesy of: A+ REALTY PROFESSIONALS, INC (407-702-5243)
Listing Agent: Darlene Chance (407-247-2307)
1149 CHARMING ST, MAITLAND, FL 32751
$590,00036 Days on yellowkey MLS ID: O6414938
1 Days Off yellowkey (back on 6/23/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2474 Built: 2006Monthly Fee: $520 Tax: $5,576 (2025)Community: Enclave/Maitland A-FTownhouse
Taxes:$5,576
Remarks: The Enclave at Maitland (Montacino), Beautifully Updated, First Floor Primary Bedroom, Oversized 20' x 26' Garage, Gated Community Living in the Enclave at Maitland which is highly sought-after, offering the perfect blend of style, comfort, and maintenance-free living. This fully updated Spanish-style townhome features 4 bedrooms, 3.5 bathrooms, a private paver courtyard, and an oversized attached two-car garage measuring approximately 20' x 26'—providing valuable extra space for storage, hobbies, a workshop area, or larger vehicles. One of the home's most desirable features is the spacious first-floor Primary Suite, offering privacy and convenience along with a beautifully updated en-suite bath featuring dual vanities, a soaking tub, separate shower, and walk-in closet. The thoughtfully designed floor plan is enhanced by soaring 9'8" ceilings on the main level, extensive crown molding, ceiling fans, and abundant natural light throughout. At the heart of the home is a stunning remodeled kitchen featuring 42-inch cabinetry with crown molding, granite countertops, stainless steel appliances, breakfast bar seating, and a cozy breakfast nook overlooking the private courtyard. The kitchen, all bathrooms, and even the laundry room have been tastefully updated, providing a move-in-ready experience for the next owner. You've got to see it! Upstairs you'll find a second private suite with its own updated bathroom, two additional bedrooms, another full bath, and a conveniently located laundry room. Closet organizer systems throughout the home provide exceptional storage and functionality. Residents enjoy access to a resort-style community pool overlooking picturesque Lake Charity, all within the security and convenience of a gated neighborhood. Ideally located near Maitland Boulevard and I-4, this exceptional location provides easy access to Downtowns of Orlando, Maitland and Winter Park, with premier shopping, dining, entertainment, and major employment centers. Offering a rare combination of updated finishes, flexible living space, oversized garage storage, and an unbeatable location, this exceptional townhome is ready to impress even the most discerning buyers.
Listing is courtesy of: YOUNG REAL ESTATE (407-904-0069)
Listing Agent: Ross Hudson (407-247-7288)
1511 E HORATIO AVE, MAITLAND, FL 32751
$719,00086 Days on yellowkey MLS ID: O6401235
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2676 Built: 1957 Tax: $6,013 (2025)Community: Minnehaha ShoresSingle Family
Taxes:$6,013
Remarks: Welcome to your dream home located in the heart of Maitland, FL. This stunning 4-bedroom, 3-bathroom residence is a perfect blend of modern comfort and timeless elegance. Lease Purchase available with a downpayment. Total Living Area 2760 Sq Ft. As you step inside, you'll be greeted by an inviting foyer that leads to a spacious open-concept living area, featuring high ceilings and abundant natural light. The gourmet kitchen boasts quartz countertops, new appliances, and ample cabinet space, ideal for culinary enthusiasts. The adjoining dining area is perfect for entertaining guests or enjoying family meals. The master suite is a true retreat with a walk-in closet and an en-suite bathroom featuring a luxurious soaking tub, dual vanities, and a separate shower. Three additional bedrooms provide plenty of space for family or guests, while the three full bathrooms ensure convenience and privacy for all. Outside, the large backyard offers a serene setting with a covered fenced-in yard, perfect for outdoor dining or relaxing in the Florida sunshine. The newly meticulously landscaped yard is designed for low maintenance, allowing you to enjoy the beautiful surroundings without the hassle. This property is located in a prime location, just minutes away from top-rated schools such as Maitland Middle School and Winter Park High School. Enjoy easy access to local landmarks and attractions including the Maitland Art Center, Lake Lily Park, and the Enzian Theater. For your shopping and dining needs, the Maitland City Centre and Winter Park Village are just a short drive away, offering a variety of upscale boutiques, restaurants, and entertainment options. Don't miss this incredible opportunity to own a piece of Maitland's finest real estate. Schedule your private tour today and experience the elegance and convenience of 1511 East Horatio Avenue. This home won't last long!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Gustavo Vargas (407-854-2161)
444 BANYON TREE CIR #202, MAITLAND, FL 32751
$239,90071 Days on yellowkey MLS ID: TB8502707
REDUCED by $10,100 (4.0%) on 06/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1428 Built: 1973Monthly Fee: $555 Tax: $2,506 (2024)Community: Carrington Park A CondoCondo
Taxes:$2,506
Remarks: Beautifully well-maintained 3 bedroom, 2 bathroom condo located in the desirable Maitland area. This second floor unit features an updated kitchen, laminate flooring throughout, and an ope-concept layout that offers abundant natural light, including a bright and inviting porch space. The spacious primary-suite includes two walk-in closets. The communit offers a playground, fitness center, clubhouse a nice pool. Located closed to major roads and is walking distance to Publix, Starbucks and many other stores. Don't miss this exceptional opportunity!
Listing is courtesy of: THE KEYES COMPANY (305-371-3592)
Listing Agent: Lidia Gloria (561-756-3266)
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