Location: Maitland
Do Not Show Listings
1010 WINDERLEY PL #127, MAITLAND, FL 32751
$329,900100 Days on yellowkey MLS ID: O6395028
REDUCED by $2,600 (0.8%) on 07/09/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1563 Built: 1997Monthly Fee: $375 Tax: $4,625 (2025)Community: Villas Lake DestinyTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,625
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Tax Year: 2025
Middle School: Lockhart Middle
Remarks: Back on the market through no fault of the property. Recently appraised at $340,000 and inspections were completed without issue. A great opportunity for a qualified buyer seeking a smooth transaction and quick closing. Tucked into one of Maitland's most coveted lakefront enclaves, this beautifully updated townhome sits within a quietly maintained, tree-lined setting with direct access to Lake Destiny, a private community boat ramp, resort-style pool, and tennis courts, all just minutes from I-4, the 414, RDV Sportsplex, and the dining and shopping corridors of Maitland Center. First impressions set a private and secluded tone with a wrought-iron gated courtyard leads to a covered entry porch before you reach the front door. Inside, soaring vaulted ceilings and a dramatic arched transom window above the sliding glass doors flood the main level with natural light, creating an airy, open feel that far exceeds the square footage on paper. Wide-plank tile flooring runs throughout the main living areas, connecting the open living and dining spaces to a thoughtfully updated kitchen featuring white shaker cabinetry with crown accents, solid stone countertops, stainless steel appliances including a French door refrigerator and built-in microwave, pendant lighting above the breakfast bar peninsula, and a subway tile backsplash. The sliding doors open directly to a private screened patio framed by mature landscaping, creating the kind of indoor-outdoor flow that defines Florida living at its best. Upstairs, three generously sized bedrooms each offer ceiling fans, ample closet space, and brand new carpet and paint. The primary suite stands out with a 26ft footprint, two closets including a walk-in, and an ensuite bath featuring dual vanities, a full-wall vanity mirror, and a walk-in shower. Two additional bedrooms and a full bath complete the upper level, with the layout providing genuine separation and privacy between spaces. Back on the main floor, a versatile 9x9 bonus room with indoor laundry handles the day-to-day, and the full-size washer and dryer convey. The big-ticket items are handled: 30-year tile roof replaced in 2023, HVAC installed in 2020, and brushed nickel fixtures updated throughout. The one-car garage with additional driveway parking and the gated courtyard entry give this unit a sense of privacy and security rare in townhome living. Whether you are looking for a low-maintenance primary residence, a lock-and-leave second home, or a smart investment in a well-managed community with real amenities and a lakefront address, this one makes an easy case.
Listing is courtesy of: DON HARKINS REALTY LLC (321-377-0341)
Listing Agent: Donald Harkins, Iii (321-377-0341)
51 OAKLEIGH LN, MAITLAND, FL 32751
$1,110,00085 Days on yellowkey MLS ID: O6399404
REDUCED by $25,000 (2.2%) on 07/08/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4149 Built: 1972 Tax: $5,558 (2025)Community: Oakleigh Third AddSpa: NoSingle Family
Taxes:$5,558
Elementary School: None
High School: None
Middle School: None
Remarks: Come see 51 Oakleigh Ln, a functional residence arranged for everyday practicality. A comfortable living space features a fireplace. The kitchen includes an accent backsplash and all stainless steel appliances. The primary bedroom has a walk in closet, and its bathroom features double sinks and a separate tub and shower. Outside, a patio connects to an in ground pool within a fenced in backyard. This property is a must-see for comfort and outdoor living. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
1140 S ORLANDO AVE #E11, MAITLAND, FL 32751
$195,9008 Days on yellowkey MLS ID: O6421126
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 612 Built: 1971 Tax: $2,526 (2024)Community: Lake Maitland Terrace AptsCondo
Taxes:$2,526
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2024
Middle School: Maitland Middle
Remarks: LAKE LIFE!! Welcome to 1140 S. Orlando Ave E11, a charming lake access condo perfectly nestled on the border of Winter Park and Maitland. Embrace the laid-back Florida lifestyle with Lake Maitland just steps away, offering endless opportunities for paddle boarding, kayaking, boating and relaxing by the water. A brand-new community pool with stunning lakefront vibes to enjoy poolside get togethers. The on-site clubhouse isn't just a great place to unwind, it's also available to rent for private events and gatherings, making it ideal for hosting celebrations or get-togethers with friends and family. Other amenities include a shuffle board and putting green. Inside the condo, you'll find a functional layout with defined living and dining areas, cozy charm, and loads of potential. This unit offers a comfortable, well-maintained space in one of Central Florida’s most scenic communities. Whether you're soaking in the lake breeze, heading out for a paddle, or planning your next event at the clubhouse, this is your chance to live the lake life you've been dreaming of. Walking distance to Eden Bar and Enzian theater, Lukes, Antonio's, Francesco's, the Shoppes at Maitland, and festive Lake Lily. This condo is turn-key ready. Unit comes with small storage unit. Laundry on site. No washer/dryer in unit.
Listing is courtesy of: IAD REAL ESTATE (407-720-0020)
Listing Agent: Abby Green (321-947-4460)
1783 SUNNYSIDE DR, MAITLAND, FL 32751
$849,9009 Days on yellowkey MLS ID: O6420390
0 Days Off yellowkey (back on 7/8/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2055 Built: 1986 Tax: $4,197 (2025)Community: Dixie TerraceSpa: NoSingle Family
Taxes:$4,197
Remarks: Under contract-accepting backup offers. Perfectly positioned between Maitland and Winter Park, this beautifully maintained 3-bedroom, 2.5-bath pool home offers an exceptional combination of charm, character, and an unbeatable location just minutes from the shops and restaurants of Park Avenue. Warm hardwood floors flow throughout the home, while the impressive two-story family room showcases soaring ceilings and a wood-burning fireplace that creates a welcoming gathering space. Separate living and dining rooms provide flexibility for both everyday living and effortless entertaining. The kitchen is thoughtfully designed with newer stainless-steel appliances and opens to the family room. French doors invite you outside to a private backyard retreat, while the adjacent sunroom is the perfect place to enjoy morning coffee with peaceful views of the pool and lush landscaping. Upstairs, you'll find three spacious bedrooms and two beautifully renovated baths. The primary suite is filled with natural light from a charming bay window and features a spa-inspired bath with marble floors, quartz countertops, dual vanities, and timeless subway tile. Step outside to your own backyard oasis. The covered lanai, complete with a summer kitchen, overlooks a newer saltwater pool and an expansive brick patio, creating the ideal setting for year-round outdoor living, entertaining, or simply unwinding in a private, tranquil setting. Adding to its appeal, the home is located just one house from the Winter Park city limits and is zoned for highly acclaimed Dommerich Elementary, Maitland Middle, and Winter Park High School. Enjoy the convenience of nearby Lake Lily, Enzian Theater, Maitland City Centre, and the boutiques, dining, and vibrant lifestyle of Winter Park's famed Park Avenue. This home offers the rare opportunity to enjoy a peaceful neighborhood setting with the very best of Maitland and Winter Park just moments away.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Wendy Williams Crumit (321-356-8590)
1750 POCAHONTAS PATH, MAITLAND, FL 32751
$599,000101 Days on yellowkey MLS ID: O6394358
REDUCED by $20,000 (3.2%) on 07/02/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1922 Built: 1957Monthly Fee: $17 Tax: $4,060 (2025)Community: Dommerich Estates 1St AddSingle Family
Taxes:$4,060
Remarks: Set along a quiet, tree-lined street in Maitland, this 3 bedroom, 2 bathroom home with 1,922 square feet captures the essence of mid-century modern design with a fresh, updated edge. Clean lines, open flow, and a strong connection to the outdoors define the home from the moment you step inside. Major updates include the kitchen in 2019, bathrooms in 2021, Roof 2022, and HVAC in 2024. The living spaces feel intentional and uncluttered, with natural light highlighting the architectural simplicity that makes this style so enduring. An updated kitchen anchors the home with modern finishes and functionality, complemented by an eat-in dining area that invites everyday gathering. A dedicated bar area adds character and ease for entertaining, creating a space that feels both relaxed and refined. A separate office/flex space provides flexibility for today’s lifestyle, offering a quiet place to work or create without disrupting the flow of the home. Updated bathrooms carry a cohesive, minimalist design throughout, staying true to the home’s architectural roots. The outdoor space continues the story. Minimalist landscaping and open, usable areas create a calm and private setting that feels like a natural extension of the interior. It is a setting designed for both quiet mornings and easy evenings with friends. An optional HOA provides deeded lake access, adding a lifestyle component that is increasingly hard to find. All of this is paired with access to some of the most highly regarded schools in Central Florida and a location just minutes from Park Avenue, dining, and shopping. This is not just a home with style. It is a home with intention.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brian Rotenberger (407-948-8478)
1404 CARING CT, MAITLAND, FL 32751
$639,00021 Days on yellowkey MLS ID: G5113516
REDUCED by $20,500 (3.1%) on 07/08/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2110 Built: 2005Monthly Fee: $285 Tax: $8,409 (2025)Community: Enclave At Maitland A-FSingle Family
Taxes:$8,409
Remarks: "PRICE IMPROVEMENT" ON THIS MOVE-IN READY 3-BED, 2.5-BATH SINGLE FAMILY HOME IN THE "EXCLUSIVE GATED COMMUNITY OF ENCLAVE AT MAITLAND", FL 32751. Nestled within the highly sought-after & gated community of Enclave at Maitland, Single Family Homes rarely come on the market and this home offers a Luxury Interior Footprint that's a perfect balance of privacy, elegance, and convenience. Fully updated & loaded with high-end finishes, the triple split-plan layout features separate Formal Dining & Family Rooms that maximize both entertaining and day-to-day privacy. Enter through a HUGE 21' Long Foyer into the Large Family Room which boasts a 14' High Tray Ceiling and the Centerpiece of the home. Just off the Family Room is the Formal Dining room, perfect for entertaining & family dinners. The Kitchen is perfectly designed for the Serious Chef, boasting Level 3, 42" Maple Cabinetry with Upper Crown Molding, Premium Granite, Center Island with a (3) Person Breakfast Bar, Stainless Appliance Package including Double Built-In Ovens, French Style Refrigerator, Flat-Top Range, Tons of Counter & Storage Space, Dual Stainless Sink, Custom Tile Backsplash, Pendant & Recessed Lighting, Closet Pantry and an adjoining Sunlit Dinette that provides the perfect spot for casual morning coffee. The Primary Suite is the Perfect Couples Retreat! The Bedroom is generous in size and will accommodate all of your oversized furniture & features a HUGE Tray Ceiling, Crown Molding, Laminate flooring, and Dual Walk-In Closets outfitted w/Custom Storage Organizers. The En-Suite Bathroom offers His-and-Her Maple Vanities w/Undermount Sinks, Granite Counters, Deep Garden Soaking Tub wrapped in Custom Tile, Large Walk-In Shower engineered with Dual Shower heads at opposite ends, Under-Cabinet Accent Lighting and a Glass Block Window for lots of natural lighting. On the opposite side of the residence, Two Additional Bedrooms share a beautifully appointed Full Bathroom, offering an ideal setup for Children & Guests. If you work from home or just looking for a quiet space, you'll enjoy the Private Office/Den located just off the Family Room. The Interior Laundry Room is highly functional and included Front-Load Washer & Dryer, Integrated Wash Tub/Sink & Upper Storage Cabinets. Your living space effortlessly expands outdoors through a Triple-Slider to the 12'x16' Covered Back Porch w/Premium Slate Tile flooring. Here, you can unwind against the peaceful backdrop of an unobstructed Lake View & Conservation Area. Additional Features: Prestigious Maitland Lifestyle, Low-Maintenance Luxury, Directly Across from the Pool, Block & Stucco, Barrell Tile Roof, Freshly Painted Inside & Out, High Ceilings Throughout, Carrier HVAC (2021), Vacuflo Central Vac System, GE Hybrid 50 Gal Water Heater (2016), Double-Paned Windows, 18x18 Tile Flooring Flowing Diagonally, Premium 8" Crown Molding, Elegant Custom Arches, Tray Ceilings, 8’ High Doors, Upgraded 6" Baseboards, Surround Sound Speaker & Prewire, Security System, Ceiling Fans/Light, Pre Plumbing for Summer Kitchen, Epoxy Coated Garage Floor and (2) Garage Door Openers, Custom Garage Storage, Paver Driveway, Beautiful Palms, Magnolias & Ivy, Private Mailbox, Irrigation System and more. Incredible location close to I-4, Downtown Maitland, Altamonte & Orlando, Shopping, Dining, Theme Parks, Turnpike, Beaches and all Central Florida has to offer. Call today for more info or schedule a private showing. This is Move-In Ready Perfection!
Listing is courtesy of: ROCK SPRINGS REALTY, LLC (877-333-2811)
Listing Agent: Joel Bornstein (407-252-8092)
1140 S ORLANDO AVE #E2, MAITLAND, FL 32751
$214,50054 Days on yellowkey MLS ID: O6404875
REDUCED by $5,000 (2.3%) on 07/08/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 612 Built: 1971 Tax: $539 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$539
Remarks: Live the lake lifestyle in this beautifully updated 1-bedroom condo located in the iconic mid-century modern community of Lake Maitland Terrace. Completely refreshed in 2025, this first-floor residence features a brand-new HVAC system, new appliances including washer, dryer, and kitchen disposal, updated kitchen countertops, and new flooring throughout the living areas. Freshly painted and thoughtfully enhanced, the home blends timeless mid-century character with modern comfort and style. The spacious bedroom showcases sleek modern concrete flooring, adding to the authentic architectural aesthetic and contemporary feel. Perfectly positioned within a charming two-story mid-rise building, this residence offers effortless access to the community’s exceptional waterfront amenities and relaxed lakefront atmosphere. Set on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—residents enjoy direct lake access for boating, kayaking, canoeing, fishing, and water-skiing. A private community dock is located on-site, while the City of Maitland public boat ramp sits conveniently next door. Boat slips may also be available upon request. The location is truly unbeatable. Just one block from Lake Lily and Fort Maitland Park, and only minutes from Park Avenue, residents can walk to the Maitland Farmers Market, local restaurants, coffee shops, gym, dry cleaning, barber shop, boba tea, and more—all directly across the street. Enjoy easy biking access to Park Avenue for premier shopping, dining, and entertainment. Residents of Lake Maitland Terrace enjoy outstanding amenities including a newer community pool, lakefront clubhouse with breathtaking views available for private events, on-site laundry facilities, free unlimited water, and twice-weekly valet trash service. Experience maintenance-free living where iconic mid-century modern design meets modern updates and an unmatched Central Florida lakefront lifestyle.
Listing is courtesy of: METRO CITY REALTY (407-237-3331)
Listing Agent: Beatrice Miranda (407-592-4448)
249 W LAKE FAITH DR #205, MAITLAND, FL 32751
$325,00055 Days on yellowkey MLS ID: O6406744
REDUCED by $14,000 (4.1%) on 06/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1739 Built: 1974Monthly Fee: $620 Tax: $1,339 (2025)Community: Lake Faith VillasCondo
Taxes:$1,339
Remarks: One or more photo(s) has been virtually staged. Tucked away in this delightful and quiet lakefront community this beautifully renovated GROUND FLOOR condo offers so much, including a 2 PARKING SPACES - one is a deeded carport and the other is an open assigned parking spot... And there is a separate storage closet too! Situated on one level, this condo overlooks the charming grounds and a peek of Lake Faith from the living areas and porch. Inside is a treat for sure with a large open living and dining room layout that is light and bright. The unit has a luxury vinyl plank flooring throughout most of the unit and tile flooring in the kitchen and baths. The kitchen is updated with granite countertops and plenty of cabinetry. Off the living room is an expansive back porch that has tile flooring and was recently updated with newer windows and entry door (2024) .... And off the dining area is a charming, covered porch. So, lots of areas to enjoy day to day or if you like to entertain. The master bedroom is a spacious size and also opens to the back porch… You will love the master bath - completely redone with a large shower, a stylish vanity with ample storage as well as a make-up vanity and a generous walk-in closet. The 2 additional bedrooms are both a good size with great closet storage. Other notable features are the inside laundry closet with open shelving and newer LG washer and dryer (2024) and the custom shades installed in the living areas and bedrooms (2023). Along with these upgrades, there have been system updates including new hot water heater (2015), new AC (2016) and replumbed (2013). This complex offers a private, tranquil atmosphere and has terrific amenities including a gated entrance, clubhouse, and pool. And the location couldn’t be more convenient, with easy access to I-4 as well as a new retail and restaurant development within a short stroll. This is one not to miss!
Listing Agent: Dawn Romance (407-929-2826)
1511 GLASTONBERRY RD, MAITLAND, FL 32751
$549,00065 Days on yellowkey MLS ID: O6404282
REDUCED by $16,000 (2.8%) on 06/24/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2376 Built: 1969 Tax: $1,959 (2024)Community: NorthgateSingle Family
Taxes:$1,959
Remarks: This AMAZING!, spacious 5-bedroom, 3-bath split-level home is located in a fantastic neighborhood and is packed with standout features. Upstairs, you’ll find beautiful engineered hardwood flooring throughout the main living areas, with carpet in the bedrooms and tile in the baths. A stunning screened-in porch overlooks the backyard and pool, offering a perfect spot to relax or entertain. The bright and airy formal living room provides plenty of space, while the dining room includes sliding doors that lead out to the porch. The large eat-in kitchen offers ample cabinet storage and even features a convenient pass-through window to the porch/outside bar—ideal for hosting. The upper level includes three bedrooms two bathrooms. Just a few steps down, the lower level opens to a massive family room with tile floors set to entertain family and friends with two additional bedrooms with carpet and a full bath. Tile flooring runs throughout this level. Additional highlights include outdoor spa , updated windows, a re-piped plumbing system, updated Electrical, and a well-maintained interior full of character. The home comes with paid in full solar panels and a Terminix termite bond and Well Maintained sprinkler system on well. Washer/Dryer are located in the garage. The garage include cabinets for additional storage. The yard features mature Citrus trees and Magnolia trees adding to the home’s charm. With its flexible layout, inviting screened porch, and beautiful salt water pool area, this home truly has it all.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Maydelin Munoz (407-485-4990)
726 FOREST GLEN CT, MAITLAND, FL 32751
$559,90011 Days on yellowkey MLS ID: O6420590
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1801 Built: 1973 Tax: $2,879 (2025)Community: Forest Brook 5Th SecSpa: NoSingle Family
Taxes:$2,879
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: This beautifully redesigned and renovated move in ready pool home sits on a quiet cul-de-sac in desirable Maitland. Inside, the open floor plan features a brand-new kitchen with quartz countertops, shaker cabinetry, waterfall island, and stainless-steel appliances. Luxury flooring, remodeled baths, and modern finishes run throughout. Major updates include a new roof, newer HVAC, newer water heater, and French doors that open to a large backyard oasis. A bonus room with a mini split AC offers flexibility for an office or gym. Enjoy the private pool, patio, and proximity to top schools, shopping, and dining.
Listing is courtesy of: FLORIDA REALTY OF MIAMI CORP (305-598-5488)
Listing Agent: Janet Garay (786-355-7514)
823 WOODS COURT, MAITLAND, FL 32751
$950,0003 Days on yellowkey MLS ID: O6422384
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2145 Built: 1979 Tax: $7,742 (2025)Community: Dommerich WoodsSingle Family
Taxes:$7,742
Remarks: Outstanding Dommerich Woods location on .28 acre lot with serene views of the nature preserve! This immaculate home offers the perfect blend of comfort, style and privacy. Tucked away on a charming tree-lined cul-de-sac, 823 Woods Court welcomes you with exceptional curb appeal. Step inside to a spacious foyer introducing gleaming wood floors, elegant crown molding, and an abundance of natural light. The versatile floor plan offers several inviting living spaces! At the front of the home, the formal living & dining rooms flow seamlessly into the beautifully updated kitchen, complete with a cozy breakfast nook, new cabinetry, quartz countertops, stainless steel appliances and an oversized breakfast bar overlooking bright family room. French doors open to the spectacular 28x11 sunroom with vaulted ceilings and a stunning wall of windows, providing breathtaking views of the manicured backyard, two private patios and the tranquil nature preserve- creating a peaceful retreat you'll enjoy year-round. The spacious primary suite features two closets and a generously sized en-suite bath with dual vanities and built-in storage. Two additional guest bedrooms and a large guest bathroom with built-in closets provide plenty of space for family and visitors. Additional updates and features include fresh interior paint, an inside laundry room, a two-car garage with new garage door, a new Trane HVAC system. new water heater. irrigation system with new well pump, & NO HOA! Excellent schools: Dommerich Elementary, Maitland Middle & Winter Park High! Residents enjoy access to the Dommerich boat ramp on Lake Minnehaha/Chain of Lakes, as well as a short stroll to the newly refurbished boardwalk leading to Maitland Community Park. This move-in ready home combines an exceptional location, thoughtful updates, and picturesque surroundings ...WELCOME HOME!
Listing Agent: Catherine D'Amico (407-252-3210)
200 MOSELEY AVE, MAITLAND, FL 32751
$410,00036 Days on yellowkey MLS ID: O6413652
0 Days Off yellowkey (back on 7/7/2026)
REDUCED by $10,000 (2.4%) on 06/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1625 Built: 2026 Tax: $1,843 (2025)Community: Pindar SubSingle Family
Taxes:$1,843
Elementary School: Hungerford Elem
Remarks: Every detail of this home was thoughtfully curated to offer timeless beauty, upscale finishes, and modern functionality. This exceptional property blends contemporary design with everyday comfort, creating the perfect living experiences. The oversized walk-in shower creates a true resort-style experience with floor-to-ceiling marble-inspired tile, frameless glass enclosure, rainfall showerhead, and designer pebble stone flooring that adds texture and tranquility. Natural light pours through the window, enhancing the bright, airy atmosphere while highlighting the glossy porcelain tile floors that flow seamlessly throughout the space. lastly this home has the perfect blend of modern elegance and functionality in this beautifully designed gourmet kitchen. Featuring stunning granite countertops, sleek custom gray shaker cabinetry, and premium stainless-steel appliances, this space was crafted with both style and everyday living in mind.
Listing is courtesy of: SYCHAR REALTY (407-921-0069)
Listing Agent: Brianna Grant (407-764-8436)
2329 COAWOOD #103, MAITLAND, FL 32751
$140,0008 Days on yellowkey MLS ID: O6421431
0 Days Off yellowkey (back on 7/6/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1206 Built: 1973Monthly Fee: $470 Tax: $2,475 (2025)Community: Carrington Park A CondoCondo
Taxes:$2,475
Remarks: Under contract-accepting backup offers. Welcome to Carrington Park — one of Maitland’s most conveniently located communities! This ground-floor 2-bedroom, 2-bathroom condo offers 1,200+ square feet of comfortable living space at an unbeatable price point, making it an ideal primary residence or a smart addition to any investment portfolio.The open living and dining area flows naturally to a private screened patio perfect for enjoying Florida’s year-round weather without the bugs. Both bedrooms are generously sized, and the split-style layout offers privacy for owners and guests alike.Residents enjoy access to community amenities including a sparkling pool, fitness center, and more, all just steps from your front door. Situated at the corner of Howell Branch and SR-436, you’re minutes from shopping, dining, and major employers, with easy access to UCF, Full Sail, and Downtown Orlando.Whether you’re looking for a place to call home or a turnkey rental opportunity in a high-demand corridor, this one checks all the boxes. Priced at $140,000, schedule your showing before it’s gone.
Listing is courtesy of: NEXTHOME SUNSHINE REALTY (321-900-2389)
Listing Agent: Jahmarie Jean (919-638-5652)
1140 S ORLANDO AVE #H3, MAITLAND, FL 32751
$419,90021 Days on yellowkey MLS ID: O6415783
REDUCED by $20,000 (4.5%) on 07/07/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 816 Built: 1964Monthly Fee: $546 Tax: $2,530 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$2,530
Remarks: Virtually Staged. RARE LAKEFRONT opportunity to Live right on LAKE MAITLAND! Sip your morning coffee with one of the most premier views in the entire community! BONUS: It's on the main FIRST floor, so NO STAIRS! Just a pure unencumbered view of Lake Maitland right from your living room! And only a few steps to the dock or community pool!! This unit has the EXTRA HALF BATHROOM and has been tastefully updated to accentuate it's incredible mid century modern original features, that are in immaculate condition! There may never be another unit quite like this one! The high end plantation shutters offer privacy when needed, but can stay wide open for that view! Enjoy the remodeled Community POOL & Clubhouse all on the stunning water front of Lake Maitland which is also connected to the Winter Park Chain of Lakes. Plenty of fishing, fun and relaxing to be had on the community dock, shuffleboard and putting green! So many amenities nestled amongst the towering shade trees and mature landscaping. The Mid Century Modern architecture is about as timeless of a look that you can find that fits the Maitland/Winter Park lifestyle. You couldn't ask for a better location at just minutes from downtown Winter Park, Park Ave, SunRail station and all the restaurants surrounding the 17/92 Maitland/Winter Park Corridor. All Units recently had metal roof replacement in 2025 and were just freshly painted as well. It's completely move in ready with all New Luxury Vinyl Plank Flooring, Kitchen and bathroom updates,. This unit has not been available for many years, so don't miss out on this view!
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Christopher Schiffermiller, Llc (407-409-5702)
814 PARK LAKE CIR #8, MAITLAND, FL 32751
$215,00065 Days on yellowkey MLS ID: O6404876
REDUCED by $1,000 (0.5%) on 07/07/2026
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1432 Built: 1972 Tax: $3,936 (2025)Community: Park Lake TwnhsCondo
Taxes:$3,936
Remarks: A beautiful affordable condo in Maitland. 2 bedrooms and 1 ½ baths with a 1 car garage. The kitchen has been updated with white cabinets and new counter tops. The appliances have been updated. There is a large dining room and separate living room. The utility room is on the 1st floor with an updated barn door for access. The 1st floor has wood flooring while the second floor has carpeting. The second floor has two bedrooms with an updated bathroom. The shower has been remodeled to allow easy access. This home has a large patio with artificial grass flooring. The one car garage is an added bonus. The property has had the window replaced, a new hot water heater and the electrical panel upgraded within the past couple of years. This wonderful unit is at a great price and will not last long.
Listing is courtesy of: NEXTHOME NEIGHBORHOOD REALTY (407-377-7735)
Listing Agent: Warren Gagne (407-461-9120)
900 BRIGHTWATER CIR, MAITLAND, FL 32751
$1,150,00010 Days on yellowkey MLS ID: O6420911
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3857 Built: 1999Monthly Fee: $395 Tax: $8,875 (2025)Community: Maitland Club RepSpa: NoSingle Family
Taxes:$8,875
Remarks: Welcome to the Premier community of Maitland Club. The paver walkway and covered front patio lead you into the spacious foyer, featuring the elegant formal living and dining rooms with hardwood floors, crown molding and plantation shutters. The Kitchen features Granite countertops, 42” cabinets and lots of natural light. The warm and inviting family room area offers a woodburning fireplace with built-in shelving and an open floor plan. The 1st Floor Master has a Large Walk-in closet and master bathroom. Separate shower and Granite countertops. Upstairs boasts a Bonus Room, ample built-in storage, and a 5th Bedroom with a large Walk-in closet. Vaulted Ceilings throughout. The Screened Pool, Covered Lanai, and Large Fenced yard are great for entertaining. The community offers tennis and basketball courts and a 24-hour guard gated community. New roof in 2024 ($80,000 value). The carpet in the home was replaced in 2020.New A/C replacement in 2024.Termite bond which is transferable. TV's convey with the home in the living room. Pool has been resurfaced. The master bath and kitchen have been updated. This home is located within minutes of downtown Winter Park, Maitland Town Center, shopping, restaurants, hospitals, Genesis Health Club and easy access to I-4.
Listing is courtesy of: ENGEL & VOLKERS ORLANDO DR PHILLIPS (407-905-6700)
Listing Agent: David Alderman (407-758-7358)
255 W GEORGE AVE, MAITLAND, FL 32751
$1,499,00027 Days on yellowkey MLS ID: O6415928
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4814 Built: 1957 Tax: $7,347 (2025)Community: Replat Blk B Poors AddSingle Family
Taxes:$7,347
Remarks: A premier street offering an accessible lifestyle to Maitland’s vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. Five bedrooms, four baths, stretching across 4,814 square feet with bonus space, there are many ways to make it your own. Inspired by classic Charleston architecture with Florida influences, the exterior features French doors across the front and rear elevations, lantern-style lighting and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters and upper-level balconies at both sides of home complete the design. Enter inside to a sweeping staircase with elegant iron details, with neutral travertine flooring that flows throughout the main level and finished with volume ceilings. The kitchen, living and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink and high-end stainless-steel appliances. Generous laundry and pantry storage are bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround-sound speakers and direct access to outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms, and the spacious primary retreat opens to a private balcony spanning across the back of home and with pool views. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light, and great closet storage and additional loft are a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining or a private workspace. Outdoor speaker system adds to the ambience. Additional improvements and features include a newer metal roof (2020), two HVACs (2021), water heater (tankless Rinnai installed by Maitland/Winter Park plumbing), plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and primary suite have ceiling-installed concert speakers and outdoor speakers. Lower-floor speakers have individual room controls and are served by a pantry stereo system. This exceptional home offers a desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a standout in one of Maitland’s special neighborhoods.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
1150 LAKE SHADOW CIR #3304, MAITLAND, FL 32751
$139,90057 Days on yellowkey MLS ID: A4693485
0 Days Off yellowkey (back on 5/27/2026)
REDUCED by $10,000 (6.7%) on 05/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1048 Built: 2000Monthly Fee: $509 Tax: $3,110 (2025)Community: Visconti EastCondo
Taxes:$3,110
Remarks: Sought-after Visconti community of Maitland. The lowest 2-2 entry point currently available. This third-floor, 2-bed, 2-bath, 1,048 sqft condo features updated flooring, designer paint, LED lighting, new ceiling fans, updated faucets, and a screened patio with exterior storage. Community amenities include two pools overlooking Lake Shadow, tennis courts, lakeside walking paths, dog stations, and car wash stations, minutes to I-4, 429, downtown Orlando. Sold as-is, priced to sell.
Listing is courtesy of: JOSEPH WALTER REALTY LLC (248-294-7850)
Listing Agent: Scott Fader (248-294-7850)
1460 LAKE SHADOW CIR #7207, MAITLAND, FL 32751
$245,0003 Days on yellowkey MLS ID: O6422624
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1372 Built: 2000 Tax: $3,635 (2025)Community: Visconti West CondoCondo
Taxes:$3,635
Remarks: A rare 4 BR condo with A rated High School could be your next home. Visconti is a high end luxury community featuring a huge lakeside pool with beach entry, fitness center that rivals many commercial gyms, tennis courts, walking paths, and a fantastic clubhouse. The 2nd floor condo has an extremely functional layout that separates the master BR from the other 3 bedrooms. The kitchen is stunning with updated cabinets, solid surface counters and a gorgeous back splash. The common areas feature wood laminate floors with carpet in the bedrooms. Conveniently located in Maitland, this homes is just minutes away from restaurants, shops, I4, 414, and the Maitland business center. A fantastic choice for your main home, a 2nd home or an addition to a rental portfolio.
Listing is courtesy of: INFINITY REAL ESTATE GROUP (407-760-0835)
Listing Agent: Christopher Paul (321-277-7609)
755 WOODSIDE RD, MAITLAND, FL 32751
$925,00071 Days on yellowkey MLS ID: O6402797
REDUCED by $50,000 (5.1%) on 07/07/2026
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: NEWLY PRICED TO SELL, UNDER APPRAISED VALUE, DO NOT MISS THIS OPPORTUNITY!! SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND FINISH has been REPLACED, REFRESHED and ELEVATED to perfection and just minutes from Winter Park. Located at 755 Woodside Road in the community of Forest Brook in Maitland with 3,054 Sq Ft. of living space, in a quiet CUL-DE- SAC, this 3 BEDROOM 3 FULL BATHROOM POOL home with 2 Car garage on a .31 ACRE LOT is effortless Florida living.**SOLAR PANELS-(Avg. utilities $40/MONTH) From the moment you arrive you will be impressed with the mature, manicured landscaping and architectural features that sets the tone for the quality you will find inside. The EXPANSIVE OPEN FLOOR PLAN draws you in with an effortless flow between living, dining, and entertaining spaces. SLEEK MODERN CABINETRY, MARBLE FLOORING and DESIGNER FIXTURES elevate every room. The chef-inspired kitchen features a LARGE CENTER ISLAND perfect for casual dining, meal prep or gathering with guests. A stylish PASS THROUG BAR connects seamlessly to the Florida Room making entertaining a breeze. The OVERSIZED PRIMARY SUITE is a true retreat with MARBLE FLOORING, an abundance of natural light and CUSTOM SLIDING GLASS DOORS leading to the expansive pool deck. The en-suite bathroom features FLOATING VANITIES, MARBLE FLOORING and a SEAMLESS GLASS ENCLOSED SHOWER and STAND ALONE TUB that continues the modern aesthetic that feels like a five star hotel everyday. Laundry with sink and overhead cabinets is centrally located near the kitchen and primary suite. The focal point of the family room is the stunning MARBLE FACED FIREPLACE. Two generously sized secondary bedrooms are located off the family room, sharing a beautiful bathroom featuring marble floors, floating dual sink vanity and walk-in shower-consistent with the finishes throughout. The Florida Room is where the fun truly begins. Currently set up as the ultimate entertainment space, this incredible space offers endless possibilities- playroom, game room, movie room or the perfect indoor/outdoor lounge for hosting family and friends.NEW OVERSIZED WINDOWS frame spectacular views of the pool, floods the space with natural light and seamlessly connect the indoors to the out. The THIRD FULL BATH located off the Florida Room serves as the POOL BATH with walk-in shower, Jacuzzi, floating vanity and premium finishes. This homes outdoor spaces provide something for everyone. The large, screened-in pool deck features a Tiki Bar and dedicated PROJECTOR SCREEN AREA (Screen & Tiki Bar CONVEY IN THE SALE) perfect for entertaining pool side.The side yard with artificial turf is clean, low maintenance, and pet friendly. A charming brick paver seating area creates as cozy spot to relax, unwind or let the pets roam freely. Enjoy the tranquility of this homes beautiful backyard. ADDITIONAL LIST OF UPGRADES: 2020 HARDSCAPE & LANDSCAPING, 2021 NEW WATER HEATER & POOL PUMP, 2024/2025 REPLACED LARGE AC AND DUCTWORK, AC PRIMARY SIDE UNIT, 2025 NEW FLORIDA ROOM WINDOWS, ADDED RID-O-RUST SYSTEM TO WELL FOR IRRIGATION, SCREENED IN POOL/DECK, SOLAR PANELS (to be paid off at closing) ADDED DRY BAR WITH UPPER AND LOWER CABINETS IN DINING AREA. Conveniently located minutes away from boutique shopping, acclaimed dining and vibrant entertainment of the beautiful city of Winter Park with easy access to Orlando and surrounding communities. This home won't last long. Call your Agent to schedule a showing today!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Diane Heiken (407-920-4491)
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