Location: Maitland , 32751
Do Not Show Listings
1244 E LAKE COLONY DR, MAITLAND, FL 32751
$1,895,000Listed 04/30/2026 3:19PM MLS ID: O6402702
Bed: 4 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4226 Built: 2002Monthly Fee: $342 Tax: $17,421 (2025)Community: Lake Colony Ph 02Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$17,421
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: 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. American Home Shield home warranty offered with full price or higher offer for American Home Shield. Four point, roof certification and wind mitigation reports will be provided by the sellers.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Jennifer Sloan (407-810-8333)
636 HILLCREST AVE, MAITLAND, FL 32751
$549,000Listed 04/30/2026 2:53PM MLS ID: O6403352
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1576 Built: 1977 Tax: $6,383 (2025)Community: Greenwood AcresSingle Family
Taxes:$6,383
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Middle School: Maitland Middle
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to this beautifully updated 3 bedroom, 2 bathroom home offering nearly 1,600 square feet of comfortable living space in the heart of Maitland. Featuring a modern look throughout, this well maintained property showcases luxury vinyl flooring that flows seamlessly through the main living areas, creating both style and durability. The spacious layout includes generous living and dining areas, perfect for relaxing or entertaining, along with a functional kitchen that offers ample storage and workspace. A brand new roof installed in 2025 adds peace of mind and long term value. Step outside to enjoy a fully fenced backyard, ideal for privacy, pets, or outdoor gatherings. A wooden deck provides the perfect space for weekend barbecues or quiet evenings at home. Situated in a quiet, established neighborhood, this home offers a highly convenient location. You are just minutes from major roadways including I-4 and Maitland Boulevard, making commuting throughout Central Florida simple. Nearby shopping and dining options include Maitland Center, Altamonte Mall, and a variety of local plazas along Orlando Avenue. Parks, schools, and everyday essentials are all within easy reach, adding to the home’s overall appeal. This property combines modern updates, functional outdoor space, and a prime location, making it an excellent opportunity for a wide range of buyers.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
370 SULTANA LN, MAITLAND, FL 32751
$509,900Listed 04/30/2026 2:48PM MLS ID: O6401047
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1683 Built: 1967 Tax: $2,809 (2024)Community: Druid Hills ParkSingle Family
Taxes:$2,809
Elementary School: Lake Orienta Elementary
High School: Lyman High
Tax Year: 2024
Middle School: Milwee Middle
Remarks: Welcome to 370 Sultana Lane, a beautifully renovated 3-bedroom, 2-bathroom home located in the highly desirable Druid Hills community of Maitland. With over $60,000 in thoughtful upgrades, this move-in-ready residence offers modern comfort without the hassle of future projects. Step inside to a fully reimagined open floor plan designed for both everyday living and entertaining. A redesigned foyer creates a warm and inviting entry, leading into a bright living space filled with natural light from surrounding windows. The home features brand-new flooring, fresh interior paint, updated lighting, and new blinds throughout, creating a clean, cohesive look. The kitchen has been completely transformed with new cabinetry, modern appliances, and a large contemporary sink—blending style and functionality. The guest bathroom has been fully renovated, while the primary suite offers tasteful upgrades, including a walk-in shower with subway tile and elegant grey-and-white hex flooring. Dual closets provide added convenience and storage. At the heart of the home, the spacious living area features a charming brick wood-burning fireplace, perfect for cozy evenings. A versatile bonus room at the front of the home offers flexibility for a home office, playroom, or additional living space. Crown molding throughout adds a refined touch. Major system updates provide peace of mind, including a 2020 roof, newer AC, newer water heater, upgraded electrical panel, PEX plumbing, and energy-efficient double-pane vinyl windows. The home also includes a water softener and fully paid-off solar panels for long-term savings. The two-car garage offers ample space, plus an additional refrigerator for extra convenience. Outside, enjoy fresh exterior paint, newly installed sod, and refreshed landscaping—ready for your personal touch. Situated in a quiet, friendly neighborhood with no HOA, this property offers flexibility and freedom. It is zoned for top-rated schools in Seminole County Public Schools and is just minutes from parks, dining, and major roadways, providing easy access throughout Central Florida. Whether you're searching for a primary residence or a smart investment opportunity, this home delivers exceptional value in a prime location.
Listing is courtesy of: EQUITYPRO LLC (407-203-6860)
Listing Agent: Melissa Osborne (407-747-0885)
1994 KENASTON RD #1994, MAITLAND, FL 32751
$399,000104 Days on yellowkey MLS ID: O6374243
REDUCED by $16,000 (3.9%) on 04/28/2026
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)
2642 BROOKSIDE CT, MAITLAND, FL 32751
$629,000Listed 04/30/2026 12:22PM MLS ID: O6403669
Bed: 5 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2360 Built: 1970 Tax: $5,909 (2025)Community: Forest Brook 3Rd SecSingle Family
Taxes:$5,909
Remarks: Indulge in the epitome of modern living with this fully renovated masterpiece! Boasting a thoughtfully designed split floor plan, 5 bedrooms, and 2 bathrooms, this home offers the perfect blend of space, style, and versatility. The heart of the home, the sleek kitchen, is a culinary haven equipped with stainless steel appliances, and ample counter space with upscale quartz countertops and storage. It's a canvas for your culinary creations. Whether you're a passionate collector or a lover of occasional indulgence, the built-in wine cooler transforms ordinary moments into extraordinary ones. Beyond elegant glass doors, unveil an expansive living room that is sure to captivate. Bathed in natural light, this grand space invites relaxation, entertainment, and cherished family moments. With 5 well-appointed bedrooms, there's ample space for everyone. The split floor plan ensures privacy and convenience for all members of the household. The master bedroom is a sanctuary of sophistication and comfort. With its spacious design and thoughtful layout, it provides an inviting escape from the world outside. The en-suite bathroom complements the master suite with its lavish features, double vanities, and a spa-like shower - experience the touch of rainfall from above and immerse yourself in the lap of luxury with the ceiling-mounted shower head. A dedicated bonus room adds an extra layer of versatility, it's ideal for a home office, playroom, or creative studio, the space adapts to your unique needs. Don't miss the chance to call this fully renovated gem your own. With its spacious layout, and modern finishes.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Giancarlo Chavez (312-869-1888)
2344 SIERRA LN, MAITLAND, FL 32751
$335,000197 Days on yellowkey MLS ID: O6352359
1 Days Off yellowkey (back on 4/9/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1177 Built: 1984Community: Sierra CondominiumsSpa: NoCondo
Taxes:$0
Remarks: Under contract-accepting backup offers. Price improved! CONDO WITH PRIVATE GARAGE - JUST REPLUMBED WITH WARRANTY! Discover the perfect blend of comfort, elegance, and convenience in this beautifully updated 2-bedroom, 2-bath condominium in the highly sought-after Sierra Condominiums of Maitland. This move-in ready condo welcomes you with a screened front porch and an inviting living room with a wood-burning fireplace with an electric insert. The bonus room can be used as a television room, as a Florida room (offering a sunny spot to enjoy morning coffee while watching butterflies in the garden), or as a hobby room; leaving the living room free for formal entertaining. The upgraded kitchen features quartz countertops, under-cabinet lighting, new appliances, and accessible cupboards for easy access. A versatile breakfast nook (which is currently used as an office), includes a beautiful built-in cabinet perfect for dishes, collectibles or files. Tile floors in the kitchen and baths complement attractive laminate flooring throughout the living areas. Double-pane windows with plantation shutters, a new front door, gas heat, and a gas water heater provide comfort and efficiency year-round. Surrounded by mature trees and lush landscaping, this friendly, walkable neighborhood (with no traffic going through it), offers a warm community feel. Sierra residents enjoy a sparkling pool, tennis/pickleball court, and a welcoming clubhouse. HOA fees cover exterior maintenance, reserves for roofs, painting, roadway and pool upkeep, lawn care and cable television. A wonderful opportunity for those looking to downsize while maintaining an independent lifestyle – or an ideal first home with a coveted Maitland location!
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Kathy Mcdonald (407-973-4026)
1275 LAKE SHADOW CIR #13206, MAITLAND, FL 32751
$157,50071 Days on yellowkey MLS ID: O6383068
REDUCED by $2,500 (1.6%) on 04/30/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 672 Built: 2000Monthly Fee: $400 Tax: $1,942 (2024)Community: Visconti West CondoSpa: NoCondo
Taxes:$1,942
Middle School: Lockhart Middle
Remarks: One or more photo(s) has been virtually staged. Seller to offer credit of up to $5000 towards buyer closing costs. Water views, brand-new mechanicals, and the best price in the building. This 1-bedroom, 1-bath condo at Visconti is offered at $9,000 less than the only comparable unit in the same building — and comes with a new Goodman 2-ton, 14.3 SEER HVAC system (2025), new water heater with expansion tank (2026), and a refreshed kitchen featuring new shaker cabinets (2025), representing over $15,000 in recent improvements. Enjoy peaceful pond views from your private balcony and bedroom, accessed through a large sliding glass door off the open living area, which features built-in shelving and a bright, functional layout. A separate laundry room adds everyday convenience. Residents enjoy two resort-style pools, a fitness center, a clubhouse, and sports courts in a gated community where HOA fees include trash, water, and sewer. Minutes to I-4 with easy access to downtown Orlando, Winter Park, Walt Disney World, Universal, and Orlando International Airport. Ideal for first-time buyers, those right-sizing, or investors seeking a low-maintenance rental. Seller offering a $2,000 appliance upgrade credit, and mortgage savings may be available for qualified buyers.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Trevin Perez (305-793-6807)
921 N THISTLE LN, MAITLAND, FL 32751
$1,049,00013 Days on yellowkey MLS ID: R4911080
REDUCED by $51,000 (4.6%) on 04/22/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2300 Built: 1967 Tax: $4,489 (2025)Community: Highland Park EstatesSpa: YesSingle Family
Taxes:$4,489
Elementary School: Dommerich Elem
High School: Winter Park High
Remarks: Central location, fully renovated, A-rated schools, a resort-style pool - this Dommerich home checks every box - and it is move-in ready, turnkey for your lifestyle. Situated in one of Central Florida’s most sought-after neighborhoods for over 60 years, Dommerich is known for its top-rated schools, tree-lined streets, parks, and unmatched convenience. This home sits right in the heart of it all. Originally built in 1967 and thoughtfully reimagined in a top-to-bottom renovation completed in 2019, the property blends classic charm with modern design and systems. Major updates include roof, HVAC, plumbing, electrical, windows, doors, insulation, appliances, kitchen, primary wing addition, natural gas connection, and a Rinnai tankless water heater. Inside, the open-concept living and dining spaces flow seamlessly to a designer pool and screened patio, creating an ideal indoor-outdoor lifestyle. The modern kitchen features extensive cabinetry with drawer-based storage, a coffee bar, and easy access to the garage and main living areas. A standout feature is the 2019-built primary suite addition, offering vaulted ceilings, a custom walk-in closet, en-suite bath, laundry, utility closet, and direct access to the pool area. The home also includes a second primary bedroom with its own en-suite bath that doubles as a pool bath, plus two additional bedrooms and a shared hall bath. The curb appeal is anchored by a mature, storybook-style shade tree, setting the tone for the character found throughout the property. Enjoy a short walk to the schools on a secluded sidewalk or take in the open sports fields across the street and Maitland Community park a few streets over.
Listing is courtesy of: VISTA NATIONAL MANAGEMENT INC (407-252-5052)
Listing Agent: Garrett Mcginnis (321-278-9511)
1001 VERSAILLES CT, MAITLAND, FL 32751
$1,050,0005 Days on yellowkey MLS ID: O6401795
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3625 Built: 1981Monthly Fee: $29 Tax: $6,161 (2025)Community: VersaillesSingle Family
Taxes:$6,161
Remarks: One or more photo(s) has been virtually staged. 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!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Heather Frazee (321-689-9465)
755 WOODSIDE RD, MAITLAND, FL 32751
$999,9991 Day on yellowkey MLS ID: O6402797
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3049 Built: 1974Monthly Fee: $8 Tax: $6,508 (2024)Community: Forest Brook 5Th SecSingle Family
Taxes:$6,508
Remarks: This is the one you've been waiting for- a SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND FINISH has been REPLACED, REFRESHED and ELEVATED to perfection! 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. 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. From the moment you enter, 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 the sound of water flowing from the stone wall fountain feature in the backyard and bring your garden dreams to life planting your favorites in the large stone faced planter box. 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, 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!
Listing Agent: Diane Heiken (407-920-4491)
1610 LYNDALE BLVD, MAITLAND, FL 32751
$1,021,00042 Days on yellowkey MLS ID: G5109784
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $54,000 (5.0%) on 04/24/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2598 Built: 2006 Tax: $17,444 (2025)Community: Dixie TerraceSingle Family
Taxes:$17,444
Remarks: Under contract-accepting backup offers. PRICE REDUCTION, Incredible price for this property! LOCATION, LOCATION, LOCATION! Ideally situated just off Park Avenue in the highly desirable Maitland/Winter Park area, this beautifully maintained home offers the perfect blend of charm, functionality, and convenience. Featuring 4 bedrooms and 3.5 bathrooms, the home welcomes you with elegant formal living and dining spaces enhanced by detailed trim work, crown molding, and updated lighting. The spacious kitchen is designed for both everyday living and entertaining, showcasing a large quartz island and seamlessly overlooking the inviting family room, highlighted by a stunning fireplace. Step outside to a private backyard retreat complete with a spacious deck and covered patio—ideal for enjoying Florida’s outdoor lifestyle and hosting gatherings year-round. The primary suite, located on the second floor, offers a peaceful escape with its own private balcony—perfect for morning coffee or evening relaxation. The spa-like primary bathroom has been fully updated with a large walk-in shower, freestanding soaking tub, and modern finishes, along with an expansive walk-in closet featuring custom built-ins. Additional highlights include a freshly painted interior, a newer roof (2023), a fully fenced yard, large shed and beautifully landscaped grounds with irrigation and mature fruit trees. The extended driveway leads to a detached 2-car garage equipped with an electric vehicle charging station for modern convenience. Home is zoned for Winter Park Highs school and Dommerich Elementary. It is also conveniently located just minutes from Enzian Theater, Park Maitland School and the top shopping and dining destinations Winter Park has to offer, this move-in ready home delivers exceptional living in one of Central Florida’s most sought-after locations.
Listing is courtesy of: CAPITAL EQUITY REAL ESTATE CO (321-300-4211)
Listing Agent: Christian Del Pino (407-925-9389)
1421 SUNNYSIDE DR, MAITLAND, FL 32751
$999,999160 Days on yellowkey MLS ID: O6358123
REDUCED by $100,001 (9.1%) on 04/24/2026
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. Priced below appraised value for a limited opportunity to capture instant equity. 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)
2837 SHADOW VIEW CIR #2837, MAITLAND, FL 32751
$225,00071 Days on yellowkey MLS ID: O6382993
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1280 Built: 2000 Tax: $3,600 (2025)Community: Visconti EastCondo
Taxes:$3,600
Remarks: One or more photo(s) has been virtually staged. Move-In Ready Maitland Condo with Rare 2-Car Garage & Flexible Work-From-Home Layout Welcome to this beautifully updated three-level condo in a gated Maitland community—offering the space, flexibility, and low-maintenance lifestyle today’s buyers are looking for. This 2-bedroom, 2-bath home features a versatile office/flex room, ideal for working from home, a guest space, gym, or creative studio. Soaring ceilings, abundant natural light, and a smart multi-level layout create a bright and open feel throughout. Recent 2026 upgrades include fresh interior paint, brand-new carpet, updated bathrooms, new window blinds, and stainless steel appliances (refrigerator 2024), along with a full-size in-unit washer and dryer—making this home truly move-in ready. One of the standout features is the rare 2-car garage—hard to find in this area—offering added convenience and storage. Enjoy a low-maintenance lifestyle with HOA coverage that includes exterior maintenance, landscaping, valet trash, water, sewer, and pest control. The community offers resort-style amenities including two pools, fitness center, clubhouse, tennis and basketball courts, and playground. Ideally located just minutes from I-4, shopping, dining, and daily conveniences, this home offers both comfort and connectivity. Home includes a warranty and is available for immediate occupancy.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Nilufer Rohleder (407-962-7494)
204 QUAYSIDE CIR #504, MAITLAND, FL 32751
$459,00068 Days on yellowkey MLS ID: O6383019
REDUCED by $36,000 (7.3%) on 04/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1270 Built: 1984Monthly Fee: $590 Tax: $6,851 (2024)Community: Moorings On Lake Maitland CondoCondo
Taxes:$6,851
Remarks: Wake up to shimmering lake views and end your day with breathtaking Florida sunsets in this beautifully maintained 2 bedroom, 2 bathroom condo residence. The moment you step off the elevator and enter, you are welcomed by a bright open concept living space filled with natural light and oversized new glass sliding doors leading to your private enclosed patio. The kitchen features upgraded cabinetry, abundant natural light, a spacious eat in area, and a large island perfect for entertaining. Flooring was upgraded after purchase, new carpet was installed just six months ago, and the AC unit was replaced two years ago for added comfort and peace of mind. Custom tailored curtains add a polished finishing touch. The primary suite offers a private bath and peaceful retreat, while the split bedroom layout provides privacy for guests. Living in The Moorings means enjoying a serene lakeside lifestyle with a community pool, heated spa, clubhouse, beautifully landscaped grounds, and direct access to Lake Maitland on the Winter Park Chain of Lakes. Relax on the lakefront dock or entertain family and friends poolside. Walk across the street to Luke’s and Antonio’s or stroll to Maitland’s newly designed downtown area with open green space, farmers markets, movies in the park, and community events.
Listing is courtesy of: LUXE HUNTER REAL ESTATE (407-984-4888)
Listing Agent: Allison Hunter (407-221-4669)
1135 THUNDER TRL, MAITLAND, FL 32751
$850,00051 Days on yellowkey MLS ID: O6385581
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2966 Built: 1967 Tax: $6,279 (2025)Community: Dommerich Hills Fifth AddSpa: NoSingle Family
Taxes:$6,279
Remarks: One or more photo(s) has been virtually staged. Welcome to 1135 Thunder Trail, a beautifully updated pool home in Maitland, Florida, located in the highly desirable Dommerich Hills neighborhood. Situated on an oversized lot with no HOA, this property offers nearly 3,000 square feet of flexible living space, combining comfort, functionality, and the best of Florida outdoor living. Step inside to an open and inviting floor plan featuring a formal living room and dining area that flow seamlessly into a spacious family room, perfect for everyday living and entertaining. The heart of the home is the fully upgraded gourmet kitchen, complete with high-end appliances, double ovens, large cooktop, stone countertops, custom cabinetry, oversized refrigerator, and a massive center island designed for gathering. The family room is warm and stylish with a fireplace, custom feature wall, and a built-in wine bar with beverage coolers, bar sink, and coffee station. Large windows fill the home with natural light and provide views of the private backyard oasis. The first-floor primary suite offers a true retreat with dual walk-in closets, French doors leading to the pool, and a renovated ensuite bathroom featuring double vanities and a walk-in shower. Upstairs, you’ll find an expansive bonus room (26x17) with a half bath and built-in daybed, ideal as a media room, game room, home office, or guest suite, plus three additional bedrooms, a full bath with dual sinks, and custom built-ins throughout. Step outside to your private backyard paradise, featuring a sparkling in-ground pool, outdoor shower, fire pit area, multiple gazebo seating spaces, mature landscaping, and fruit trees. The fully fenced yard offers privacy and plenty of space for pets or play, while built-in gas lines make outdoor cooking effortless. Recent upgrades include: * New roof (2022) * New windows (2021) * New doors (2025) * HVAC (2019) * Fresh interior paint & updated landscaping Additional features include a two-car garage, large indoor laundry room with cabinetry, irrigation well, city sewer, and abundant storage throughout. Located just minutes from Maitland Social, Maitland City Centre, shopping, dining, and parks—and zoned for top-rated schools including Dommerich Elementary School, Maitland Middle School, and Winter Park High School—this home offers the perfect combination of location, lifestyle, and value. If you’ve been searching for a move-in ready pool home in Maitland with no HOA and top schools, this is the one.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Angela Worachek Pllc (503-381-1575)
1321 BENEVOLENT ST, MAITLAND, FL 32751
$374,90079 Days on yellowkey MLS ID: O6377413
REDUCED by $9,100 (2.4%) on 04/17/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1751 Built: 2006Monthly Fee: $520 Tax: $2,204 (2024)Community: Enclave/Maitland A-FTownhouse
Taxes:$2,204
Remarks: $9K BELOW APPRAISAL + SELLER OFFERING INTEREST RATE BUY-DOWN with acceptable offer. /// Why settle for "standard" when you can own a designer-caliber home in Maitland with a lower monthly payment? Priced at $374,900—well below the recent $384K appraisal—this high-end unit offers instant equity. *LIFESTYLE & LOCATION /// RECLAIM YOUR TIME: Just 10 minutes to Downtown Orlando or Winter Park. PET FRIENDLY: Montecino is a gated, pet-loving community. LAKE CHARITY: Enjoy a scenic walk right outside your door. Maintenance-free living with a resort-style pool and gated security. *UPGRADES & VALUE /// MECHANICALLY NEW: New HVAC (Jan 2025), Bosch dishwasher, and 2026 fridge/microwave. DESIGNER FINISHES: Engineered hardwoods, fresh paint, and designer lighting. HOA BONUS: Monthly dues include High-Speed Internet, WiFi, and expanded TV/Streaming.*PEACE OF MIND /// Home just passed INSPECTION. Between the verified value, mechanical updates, and potential interest rate buy-down, this is the most secure and affordable luxury entry in Maitland.
Listing Agent: Shirley Jones (407-719-9180)
225 QUAYSIDE CIR, MAITLAND, FL 32751
$560,000210 Days on yellowkey MLS ID: O6338754
2 Days Off yellowkey (back on 4/29/2026)
REDUCED by $35,000 (5.9%) on 04/03/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1734 Built: 1985 Tax: $3,080 (2024)Community: Moorings On Lake Maitland Condo Bldg 05Condo
Taxes:$3,080
Remarks: Under contract-accepting backup offers. Discover the perfect blend of style and location in this beautifully updated 3-bedroom, 2.5-bathroom townhome in the sought-after Moorings community. With 1,734 square feet of thoughtfully designed living space, this residence offers a bright, open floor plan enhanced by vaulted ceilings and an abundance of natural light. The heart of the home is the stunning kitchen, showcasing white cabinetry, quartz countertops, stainless steel appliances, a decorative hood above the cooktop, and a classic subway tile backsplash. A charming bay window creates the perfect breakfast nook, while the open-concept living and dining areas provide ideal space for entertaining and everyday living. A wood-burning fireplace adds warmth and ambiance to the living room, creating a cozy focal point. Step through French doors into a sun-drenched sunroom with walls of windows overlooking tranquil community green space – your own private retreat for morning coffee or evening relaxation. Luxury vinyl plank flooring flows throughout the main level, complemented by plantation shutters and fresh paint. The second floor houses all three generously sized bedrooms, including a serene primary suite with a completely renovated en suite bathroom featuring a double sink vanity, walk-in shower, and spacious walk-in closet with custom built-ins. The updated hall bath offers a tub/shower combo and single-sink vanity. The second bedroom also features custom built-in closet organizers for added storage and convenience. Additional features include ceiling fans, interior laundry, and an attached one-car garage. Living in The Moorings means enjoying exclusive amenities, including a community dock on Lake Maitland, sparkling pool, and clubhouse. The location is unbeatable – just moments from Maitland's charming Lake Lily Park and its popular weekly farmer's market, five minutes from the upscale shops and dining of Park Avenue, and surrounded by the best of Central Florida's shopping, restaurants, and entertainment.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
2150 TORTOISE SHELL DR, MAITLAND, FL 32751
$429,9007 Days on yellowkey MLS ID: O6392895
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1512 Built: 1997Monthly Fee: $17 Tax: $5,334 (2025)Community: WinfieldSingle Family
Taxes:$5,334
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained home in the heart of Maitland, offering the perfect blend of comfort, functionality, and Florida lifestyle living. This thoughtfully designed residence features a bright and open layout with spacious living areas, soaring ceilings, and an abundance of natural light throughout. The kitchen serves as the heart of the home, complete with ample cabinetry, generous counter space, and a convenient breakfast bar that opens seamlessly to the main living and dining areas, ideal for both everyday living and entertaining. Sliding glass doors lead to a private backyard with a paver patio, creating the perfect space to relax or host gatherings. The primary suite offers a peaceful retreat with plenty of space, natural light, and an en-suite bathroom for added convenience. Additional bedrooms are well-sized and versatile, perfect for guests, a home office, or growing households. Situated on a quiet street, this home features a fully fenced yard, mature landscaping, and a two-car garage. Conveniently located near shopping, dining, major roadways, and top-rated schools, this property combines tranquility with accessibility. Don’t miss the opportunity to make this move-in ready Maitland gem your own, schedule your private showing today.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Claire Sims Llc (203-767-8109)
1000 WINDERLEY PL #226, MAITLAND, FL 32751
$325,0002 Days on yellowkey MLS ID: O6402450
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1538 Built: 1982 Tax: $1,318 (2025)Community: Sun Bay Club CondoCondo
Taxes:$1,318
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath condo located in the highly desirable Sun Bay Club in Maitland. Offering 1,538 square feet of living space, this second-floor unit combines comfort, style, and convenience in a serene, gated community setting. Step inside to an impressive open floor plan featuring soaring 20-foot ceilings that create a bright and airy atmosphere, seamlessly connecting the living and dining areas—perfect for both everyday living and entertaining. The cozy fireplace adds warmth and charm, making this space feel like home from the moment you walk in. The newly remodeled kitchen is a standout, offering modern finishes and functionality for any home chef. Just beyond, enjoy your private sunroom with peaceful views of the community’s water fountain—an ideal spot for morning coffee or unwinding at the end of the day. Residents of Sun Bay Club enjoy access to exceptional amenities, including a clubhouse, pool, tennis courts, and scenic walking paths around the expansive lake. The location is unbeatable—just a short walk to the RDV Sportsplex and conveniently close to shopping, major highways, and everyday essentials. Plus, you’re only a short drive to downtown Orlando, world-famous theme parks, and Orlando International Airport. Additional highlights include a roof that is only 2 years old, offering added peace of mind. This is a fantastic opportunity to own a spacious, updated condo in a prime location—schedule your private showing today!
Listing is courtesy of: INVESTOR'S REAL ESTATE LLC (407-688-4355)
Listing Agent: Cece Mercado (407-300-8823)
2517 CAPER LN #205, MAITLAND, FL 32751
$120,000176 Days on yellowkey MLS ID: O6358434
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 550 Built: 1973 Tax: $1,789 (2025)Community: Carrington Park A CondoCondo
Taxes:$1,789
Remarks: **ATTENTION INVESTORS** Take advantage of this great opportunity and Add this income producing property to your portfolio with tenant in place. Corner unit 1 bed 1 bath condo with new laminate floors and granite countertops. This second floor unit means there is no one above you and has a pool view located steps away. The mailbox and pool are only a few steps away. Location is walking distances to Publix, Starbucks and many other stores. It is also just a 10 min drive to Full Sail University and a 30 minute drive to the parks. Best location in Orlando! Best Return available!
Listing is courtesy of: MAYOLET REALTY LLC (407-491-4893)
Listing Agent: Mayolet Bornas Moreira (407-491-4893)
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