Location: Maitland , 32751
Do Not Show Listings
1140 S ORLANDO AVE #I14, MAITLAND, FL 32751
$325,00046 Days on yellowkey MLS ID: O6410595
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 816 Built: 1971Monthly Fee: $535 Tax: $2,086 (2026)Community: Lake Maitland TerrCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,086
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2026
Middle School: Maitland Middle
Remarks: One or more photo(s) has been virtually staged. Where Maitland's pristine waters meet a modern lifestyle! This luxury condominium in the coveted Lake Maitland Terrace community offers a rare blend of elegance and convenience on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Nestled among lush green spaces, this impeccably maintained mid-century modern complex boasts easy access to boutique shops, upscale dining, and vibrant entertainment. This unit stands out with its unique two-bedroom, one-and-a-half-bath layout—a rare find in the community, where most units are built with just one bath. Sunlight floods in through large windows, and warm wood floors flow throughout. This charming efficiently designed kitchen, with light cabinetry with contrasting hardware, quartz counters, and stainless steel appliances, is perfect for entertaining. Beyond the comforts of the home, enjoy the exclusive opportunity to secure a boat slip—a prized amenity in this tranquil lakeside retreat. Complex is amenity-rich with sidewalks, a community pool where residents enjoy lake access with beautiful views. The amenities include a clubhouse with a full kitchen, kayak racks, a fishing pier, and a personal storage unit. Walk to Lake Lily Park’s events, the Enzian Theater, and be just minutes from Winter Park Village and Park Avenue. Zoned for top-rated schools—Dommerich Elementary, Maitland Middle, and Winter Park High—this is a chance to embrace the best of Maitland living. Don’t miss your chance to claim this exceptional retreat as your own.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Michele Ostrander (407-435-3863)
204 QUAYSIDE CIR #304, MAITLAND, FL 32751
$395,000292 Days on yellowkey MLS ID: O6345967
REDUCED by $20,000 (4.8%) on 06/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1270 Built: 1984 Tax: $1,928 (2024)Community: Moorings On Lake Maitland CondoCondo
Taxes:$1,928
Elementary School: Lake Sybelia Elem
Tax Year: 2024
Remarks: SELLER PAYING CONCESSIONS OF 6 MONTH HOA FEES. Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the Moorings on Lake Maitland. Enjoy relaxing on the Lake Front Dock or on your own Private Enclosed Patio! Step inside this spacious 2 bedroom 2 bath great room plan, perfect for relaxing or entertaining. The beautifully upgraded kitchen has stainless steel appliances and granite counters and a charming dining nook. The master suite features an updated ensuite bath with dual sinks and a walk in shower with a custom glass enclosure. There is a generous walk in closet with custom built ins. Imagine coffee in the morning with lake views from your living room or your spacious patio. Only 5 minute drive to Winter Park's shops & Sidewalk Dining along the famed Park Avenue. Stroll over to Maitland's lovely Lake Lilly Park for Seasonal Events, Art Festivals, Concerts and local Farmer's Market! Incredible Location & Lifestyle!!!!
Listing is courtesy of: GALLERY PROPERTIES INTERNATIONAL (407-340-8487)
Listing Agent: Beatrice Cohen-Palladino, Pa (407-312-1820)
480 BANYON TREE CIR #100, MAITLAND, FL 32751
$106,000465 Days on yellowkey MLS ID: O6294907
REDUCED by $13,000 (10.9%) on 05/18/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 759 Built: 1973 Tax: $1,617 (2024)Community: Carrington Park A CondoCondo
Taxes:$1,617
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: Spacious 1/1 Carrington Park Condo; New community. Great amenities, pools, gym & club house. Close to Winter Park, Downtown Orlando & schools. The unit is in excellent condition. Floor and kitchen renovated. New air conditioning. Rented until Feb-28-2027 at $1000
Listing is courtesy of: MIAMI TANGO INVESTMENTS REALTY (786-464-8803)
Listing Agent: Moses Nae (407-499-0240)
1010 GREGORY DR, MAITLAND, FL 32751
$520,00043 Days on yellowkey MLS ID: O6411422
0 Days Off yellowkey (back on 6/1/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2227 Built: 1969 Tax: $4,288 (2025)Community: Druid Hills Estates 1St AddSpa: NoSingle Family
Taxes:$4,288
Elementary School: Lake Orienta Elementary
High School: Lyman High
Tax Year: 2025
Middle School: Milwee Middle
Remarks: Nestled in the heart of highly desirable Maitland, this spacious 4-bedroom, 2-bath pool home offers the perfect blend of location, functionality, and outdoor living on an oversized .28-acre lot with more than 12,000 square feet of property. Surrounded by mature trees and established neighborhoods, this prime location places you just minutes from Downtown Maitland, Historic Winter Park, Downtown Orlando, world-class shopping, dining, entertainment, and Central Florida’s renowned attractions. Maitland is loved for its charming restaurants, weekend farmer’s market, beautiful lakes, and scenic tree-lined streets, all while bordering some of the most prestigious real estate in Central Florida.The backyard is truly the showstopper of this property, featuring a sparkling open pool, beautiful vinyl fencing, and an expansive yard that is far larger than many homes in the area. Recent landscaping enhancements include a hardscaped entertaining space and decorative stone half wall, creating the perfect setting for relaxing, hosting guests, or enjoying Florida outdoor living under the shade of the beautiful oak tree.Inside, the home features a desirable split-bedroom floor plan with formal living and dining rooms, plus a spacious family room offering plenty of flexibility for everyday living and entertaining. The galley-style kitchen is equipped with granite countertops and overlooks the living areas for easy functionality. Attractive laminate wood flooring and tile flow throughout the home, while all bedrooms have been updated with new ceiling fans. Additional improvements include electrical upgrades, new exterior doors, a new roof installed in 2020, and added attic insulation for enhanced energy efficiency. Built with sturdy concrete block construction, this home offers lasting durability and peace of mind. The indoor laundry room includes the washer and dryer for added convenience. This is a rare opportunity to own a pool home with a large backyard in one of Central Florida’s most established and desirable locations.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kelly Hildebrand (407-310-5035)
1375 LAKE SHADOW CIR #11103, MAITLAND, FL 32751
$199,00063 Days on yellowkey MLS ID: O6405605
REDUCED by $10,777 (5.1%) on 05/29/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 898 Built: 2000 Tax: $2,714 (2025)Community: Visconti West CondominiumCondo
Taxes:$2,714
High School: Edgewater High
Middle School: Lockhart Middle
Remarks: Stunning fully renovated 2-bedroom, 1-bath condo featuring a complete top-to-bottom remodel completed in 2026, located in the highly desirable gated Visconti West community in Maitland. This move-in ready unit features luxury vinyl plank flooring throughout, a beautifully updated kitchen with modern soft-close cabinetry, sleek finishes, and stainless steel appliances, as well as a bright open-concept living and dining area. The living and dining room combination opens to a screened-in patio through large sliding glass doors, allowing for abundant natural light throughout the home. The kitchen includes a full suite of brand-new appliances, including a range, over-the-range microwave, dishwasher, refrigerator, and disposal, along with modern soft-close cabinetry and ample countertop space. Additional upgrades include a new water heater (2026) and AC system (2020). The unit also features a full-size washer and dryer and an additional storage closet on the patio. Community amenities include a resort-style pool, fitness center, clubhouse, tennis courts, and lake access. Conveniently located near shopping, dining, major highways, and downtown Orlando. Excellent opportunity for owner-occupants or investors.
Listing is courtesy of: M2M REALTY (407-401-2275)
Listing Agent: Margo Ford (407-761-6408)
1166 N LAKE SYBELIA, MAITLAND, FL 32751
$3,100,00042 Days on yellowkey MLS ID: O6411525
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 5355 Built: 1998 Tax: $11,303 (2025)Community: Lake Sybelia ShoresSingle Family
Taxes:$11,303
Remarks: Welcome to luxury lakefront living at its absolute finest in the heart of Maitland, Florida. Nestled along the pristine shores of Lake Sybelia, this extraordinary three-story estate offers an unparalleled combination of elegance, comfort, and breathtaking waterfront views. Boasting 5,355 square feet of thoughtfully designed living space, this stunning residence features six spacious bedrooms, four and a half bathrooms, and an open-concept floor plan perfectly crafted for both entertaining and everyday living. Expansive walls of glass fill the home with natural light while showcasing panoramic lake views from nearly every room. The main living area seamlessly connects the gourmet kitchen, dining room, living room, and family room, all overlooking the sparkling waters of skiable Lake Sybelia. Designed with indoor-outdoor living in mind, each floor features a balcony spanning the entire width of the rear of the home, creating multiple spaces to relax and enjoy Florida’s spectacular sunsets. Step outside to your private resort-style oasis complete with a gorgeous pool, lush landscaping, and direct lake access with your own private boat dock and lift, perfect for boating, skiing, and waterfront recreation year-round. The upstairs retreat is anchored by an impressive primary suite featuring serene lake views and private balcony access. The upper level also includes a dedicated private office, ideal for working from home while enjoying stunning lakefront views. Two additional bedrooms share a beautifully designed Jack-and-Jill bathroom, while another flexible bedroom space can easily serve as a nursery, fitness room, or additional guest bedroom. Every level of the home has been carefully designed to maximize comfort, privacy, and functionality while maintaining a sophisticated and timeless aesthetic throughout. The lower level offers endless entertainment possibilities with a spacious game room, a full movie theatre, an additional guest bedroom, and a full bathroom ideal for visitors or multi-generational living. Completing this exceptional property is a beautiful temperature controlled wine cellar holding almost 2,000 wine bottles, a two-car garage with additional storage space, a large home generator, and countless luxury details throughout. This one-of-a-kind Lake Sybelia estate delivers the perfect balance of upscale living, modern convenience, and the ultimate waterfront lifestyle in one of Central Florida’s most desirable locations.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Joseph Sipp (407-820-7016)
1230 HOLLYRIDGE TRL, MAITLAND, FL 32751
$534,900120 Days on yellowkey MLS ID: O6389346
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $40,000 (7.0%) on 05/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1641 Built: 1983 Tax: $1,955 (2024)Community: Dommerich Woods Unit 2Single Family
Taxes:$1,955
Remarks: Dommerich Woods gem! Tucked away on a cul-de-sac street in one of Maitland’s most sought-after neighborhoods, this beautifully updated 3-bedroom, 2-bath block home is the one you’ve been waiting for. Move-in ready and genuinely charming from the moment you walk in. The open floor plan feels airy and welcoming, with vaulted ceilings and natural light pouring through every room. The living room centers around a classic brick fireplace that anchors the space perfectly, while the kitchen is a true standout-quartz countertops, stainless appliances, 40-inch soft-close shaker cabinets and a built-in pantry. The layout flows effortlessly between living, dining and family spaces, making it as functional as it is inviting. The split bedroom layout offers great privacy for everyone. The primary suite is a real retreat- vaulted ceiling, spacious walk-in closet and a completely redone en-suite bath with a lovely garden window. Both bathrooms have been given a fresh, modern look that feels clean and polished. The updates list is long and impressive: newer LVP flooring throughout, AC (2022), water heater (2023), roof replaced in 2016, replumbed in 2008, newer paint inside and out, newer light fixtures and ceiling fans. Laundry is indoors and connects right to the two-car garage-a detail you’ll appreciate daily. Out back, the expansive yard is a genuine sanctuary. Mature trees, lush landscaping and total privacy make it the kind of space you’ll actually use. A large shed with 50-amp power is ready for a workshop, hobby space or serious storage-and with NO HOA, bring the toys too! Just minutes from Kewannee Park, the Seminole bike trail and easy access to major roads and local shops and restaurants. It’s a rare find in a neighborhood where homeowners rarely leave. Come take a look.
Listing is courtesy of: BOWERBIRD REALTY (407-716-0239)
Listing Agent: Stephanie Doucette (407-716-0239)
616 VILLA CIR #536, MAITLAND, FL 32751
$252,00047 Days on yellowkey MLS ID: O6410478
0 Days Off yellowkey (back on 5/28/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1256 Built: 1979 Tax: $2,360 (2025)Community: Park Lake Villas CondoCondo
Taxes:$2,360
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome home to this beautifully updated 2-bedroom, 2-bath condo offering 1,256 square feet of comfortable living in a quiet and well-maintained Central Florida community. With major upgrades already completed, this move-in-ready home combines modern style, energy efficiency, and low-maintenance living. Step inside, from your dedicated parking spot directly in front of the unit, to discover a stunning fully remodeled kitchen. Completed in 2025 and featuring granite countertops, soft-close cabinetry and drawers, recessed lighting, and an oversized island perfect for entertaining, meal prep, or casual dining. The open living space with upgraded bamboo flooring flows seamlessly through elegant French doors to a private fenced back patio and screened-in porch, creating the perfect indoor-outdoor retreat for relaxing year-round. The spacious primary suite includes a beautifully remodeled bathroom with updated shower tile and new ceramic tile flooring, completed in 2025. Additional recent upgrades provide peace of mind and long-term value, including upgraded energy-efficient windows, added insulation, a new electric panel, and a tankless hot water heater — all completed in 2025. The AC was replaced in 2020, the roof was replaced in 2024, and the exterior was freshly repainted in 2026. Enjoy the convenience of community amenities including a pool, just steps away from your front door, and exterior maintenance handled by the property management company, allowing for truly easy Florida living. Ideally located near restaurants, shopping, and major interstates, this home offers quick and convenient access throughout Central Florida while still being tucked away in a peaceful community setting. Schedule your private showing today and experience all this upgraded condo has to provide!
Listing is courtesy of: NESTA REAL ESTATE CONSULTANTS (407-442-0299)
Listing Agent: Jessica Loomis (407-953-9893)
1776 BOBTAIL DR, MAITLAND, FL 32751
$519,99991 Days on yellowkey MLS ID: G5110747
REDUCED by $5,000 (1.0%) on 05/27/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2344 Built: 1998Monthly Fee: $17 Tax: $2,578 (2025)Community: WinfieldSpa: NoSingle Family
Taxes:$2,578
Remarks: Welcome to 1776 Bobtail Drive — the kind of home that doesn’t just check boxes… it creates emotion, urgency, and that unmistakable “we need this one” reaction the moment your buyers walk through the door. From the very first glance, the curb appeal sets the stage with a warm, polished presence that immediately stands out from the competition. Inside, you’re welcomed by a light-filled, open-concept layout that feels expansive yet comfortable — the perfect balance of elegance and livability. Every space has been thoughtfully designed to flow effortlessly, creating an atmosphere that feels both elevated and inviting. The heart of the home is a beautifully positioned kitchen that seamlessly connects to the main living areas, making it ideal for entertaining, gathering, and everyday life. Whether hosting friends or enjoying a quiet night in, this home delivers the versatility today’s buyers demand. Generously sized living spaces and bedrooms provide comfort, privacy, and flexibility, while the overall layout offers a sense of ease and functionality that appeals to a broad range of buyers — from families to professionals to those simply looking to upgrade their lifestyle. Step outside and experience your own private Florida escape — a backyard setting that invites relaxation, weekend gatherings, and year-round enjoyment. It’s the kind of outdoor space that sells the lifestyle just as much as the home itself. Perfectly positioned in a highly desirable Maitland location, this property offers unbeatable convenience to top-rated dining, shopping, entertainment, and major highways — putting everything Central Florida has to offer right at your fingertips. This is not just another listing — it’s a high-impact, high-demand opportunity that shows beautifully, lives effortlessly, and is primed to sell quickly. Homes with this combination of appeal, location, and lifestyle don’t sit… they move. Bring your buyers with confidence — this is the one they’ve been waiting for.
Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)
Listing Agent: Anthony Scaraggi (516-749-6675)
1111 AUDUBON WAY, MAITLAND, FL 32751
$1,825,000136 Days on yellowkey MLS ID: O6382602
REDUCED by $150,000 (7.6%) on 05/27/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3754 Built: 1985 Tax: $13,827 (2025)Community: Maitland CoveSpa: NoSingle Family
Taxes:$13,827
Remarks: Welcome to a rare opportunity on the shores of Lake Sybelia, one of Maitland’s most desirable recreational lakes. This custom, one-owner home offers 3,754 square feet of thoughtfully designed living space that has been well-maintained with potential for cosmetic enhancements. A brick-paved horseshoe driveway and inviting front porch set the tone. Inside, rich wood floors, vaulted wood ceilings in the living and family rooms, two fireplaces, and custom built-ins showcase quality rarely found today. The spacious layout features four bedrooms and 3.5 baths, including two primary suites ideal for multi-generational living. Generous walk-in closets and a blend of wood, tile, and carpet add comfort and function. A new A/C (Oct 2025) and a 6.5-year-old roof provide peace of mind. Living areas open to a bright rear sunroom with tranquil lake views. Whether you’re entertaining by the fire, enjoying coffee on the porch, or heading out onto the lake, this property delivers the Florida lifestyle at its finest.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Melissa Shipp (407-748-7163)
105 TANGELO CT, MAITLAND, FL 32751
$1,798,999217 Days on yellowkey MLS ID: O6364116
2 Days Off yellowkey (back on 5/25/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3203 Built: 2026 Tax: $6,909 (2024)Community: Hollieanna ShoresSpa: NoSingle Family
Taxes:$6,909
Remarks: Under contract-accepting backup offers. Under Construction. A masterpiece of luxury design by LUIH Luxury Homes, perfectly positioned in the prestigious neighborhood of Hollieanna Shores. As you arrive, a striking façade with an elegant arched entryway sets an unforgettable tone. Beyond the front door, soaring ceilings and designer finishes frame an expansive living room where glass sliders dissolve the boundary between indoor and outdoor living, creating a seamless transition to the lanai and resort-style backyard. At the heart of the home, a chef’s kitchen designed for both performance and beauty exceeds every expectation. Sleek quartz countertops, a full Thermador appliance suite, custom cabinetry, and an oversized walk-in pantry elevate culinary experiences to a professional standard. The primary suite is a private sanctuary intentionally crafted to evoke a spa-like retreat. A stunning bathroom showcases a freestanding tub, an expansive walk-in shower, dual vanities, and exquisite finishes, while a large boutique-style closet with custom built-ins ensures every piece has its place. The upstairs level offers a generous loft and beautifully appointed secondary bedrooms, creating the ideal separation of space for family or guests. Outdoor living is nothing short of extraordinary, featuring a huge covered lanai with a full summer kitchen overlooking a shimmering pool and expansive, fully fenced backyard. Situated in the sought-after Hollieanna Shores neighborhood, this residence places you moments from Maitland City Centre, local parks, the iconic Enzian Theatre, and Park Ave. shopping and dining. If you’re seeking a home that feels both artful and effortless, this is where elevated living becomes reality.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
601 ORANOLE RD, MAITLAND, FL 32751
$385,900367 Days on yellowkey MLS ID: O6324872
3 Days Off yellowkey (back on 5/21/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1950 Built: 1958 Tax: $4,216 (2024)Community: Oakland Shores 3Rd Add RepSingle Family
Taxes:$4,216
Remarks: Under contract-accepting backup offers. Back on the market with renewed momentum. Nestled in one of Maitland's most sought-after neighborhoods, this fully renovated 3-bedroom, 2-bathroom home offers the perfect blend of modern comfort and timeless charm, ideal for families ready to make new memories. From the moment you step inside, you're greeted by an abundance of natural light and an open, airy layout that instantly feels like home. The heart of the house, the newly renovated kitchen features sleek stone countertops and new appliances, making it perfect for family meals and holiday gatherings. Step outside to the screened-in patio and picture slow mornings with coffee in hand, or peaceful evenings unwinding from a long day in the spacious backyard. Whether hosting a barbecue or enjoying a quiet night under the stars, this outdoor space is made for relaxation! Located just minutes from top-rated schools, grocery stores, dining, and major highways and less than 10 miles from the natural beauty of Wekiwa Springs State Park. This home offers the convenience you need and the lifestyle you've been dreaming of. Don't miss this opportunity to plant roots and grow in a home that has it all. Schedule your private tour today and discover the warmth, space, and charm waiting for your family.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Kay Shilling (407-716-9861)
220 ALPINE DR, MAITLAND, FL 32751
$427,400126 Days on yellowkey MLS ID: O6388051
REDUCED by $22,600 (5.0%) on 05/12/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 988 Built: 1953 Tax: $5,537 (2024)Community: Sunset RidgeSingle Family
Taxes:$5,537
Remarks: Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same family since the 1960s, is ideally located near shopping, dining, parks, and major roadways, providing convenient access throughout Central Florida. The property offers potential for renovation, expansion, or redevelopment, with a lot that provides space for future improvements. Ideal for homeowners, builders, or investors seeking a property in a desirable and established area. The adjacent property to the west (210 Alpine) is also available for purchase. Contact the listing agent for additional information and pricing on the neighboring parcel.
Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)
Listing Agent: Beth Hathaway (407-314-1300)
1100 S ORLANDO AVE #306, MAITLAND, FL 32751
$649,000110 Days on yellowkey MLS ID: O6392583
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1125 Built: 1973Monthly Fee: $618 Tax: $4,561 (2025)Community: West Cove CondoCondo
Taxes:$4,561
Remarks: TURN KEY AND RENOVATED IN SOUGHT-AFTER WEST COVE!! Wake up to breathtaking sunrises with a stunning, unobstructed view stretching across Lake Maitland—the largest lake in the highly sought-after Winter Park Chain of Lakes—from this beautifully renovated, truly turnkey condominium. All flooring, bathrooms, fixtures, paint, AC, water heater, sliding door to balcony, kitchen/appliances, and closet systems have been painstakingly updated to the highest level, making for an unparalleled opportunity to simply move right in and begin enjoying immersive lake views. The primary suite has been reimagined and has its own ensuite bath and a new built-in closet with copious storage, complete with signature views of Lake Maitland. This spacious residence offers an ideal central location, just moments from an array of dining options, Lake Lily Park, Enzian Theater, and convenient access to Interstate 4 via Lee Road or Maitland Boulevard. The monthly association fee—lower than most lakefront communities—provides exceptional value and includes access to lakefront docks (with boat slips available on a first-come basis), a fitness center, an inviting lobby for entertaining, a heated pool and spa, a grilling area with seating, storage for canoes, kayaks, and paddleboards, assigned and guest parking, laundry facilities on every floor, Spectrum cable and internet, as well as water, sewer, and trash services. This property may be under audio/visual surveillance.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Frank Benevento (407-492-5153)
448 STONEWOOD LN, MAITLAND, FL 32751
$624,990135 Days on yellowkey MLS ID: O6385060
INCREASED by $19,990 (3.3%) on 05/04/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3308 Built: 1980Monthly Fee: $33 Tax: $11,256 (2025)Community: StonewoodSpa: NoSingle Family
Taxes:$11,256
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 3-bathroom pool home offering the perfect blend of space, style, and location! From the moment you walk in, you’ll love the open layout and rich hardwood floors that create a warm and inviting atmosphere throughout. Designed for both everyday living and entertaining, this home features a dedicated office plus separate living, dining, and family rooms—giving everyone their own space while still feeling connected. The updated fireplace serves as a stunning focal point in the main living area, enhanced by natural light pouring in through the skylights. Recent upgrades provide added peace of mind and value, including a paver driveway and new gutters installed in 2019, full home re-pipe in 2021, air ducts sealed and new insulation added in 2021, a new pool pump and new AC compressor (one unit) in 2022, and new bedroom flooring in 2023.The kitchen is a true standout with 42” cabinetry, granite countertops, and newer stainless steel appliances, all overlooking the main living areas for seamless entertaining. A built-in wet bar adds the perfect touch for hosting gatherings and holiday celebrations. Retreat to the spacious primary suite and enjoy large closets throughout the home, providing ample storage for every lifestyle. Step outside to your private backyard oasis featuring a sparkling pool and expansive deck—ideal for relaxing weekends, outdoor dining, and Florida sunshine year-round. Located with easy access to Uptown Altamonte, I-4, 436, and Maitland Boulevard, this home places you just minutes from Lake Lily, Winter Park Village, Downtown Winter Park, and Cranes Roost—offering endless options for dining, shopping, parks, and entertainment. This home truly checks every box—space, updates, location, and a pool to top it all off! ????
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
2642 BROOKSIDE CT, MAITLAND, FL 32751
$629,00070 Days on yellowkey 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)
1140 S ORLANDO AVE #F11, MAITLAND, FL 32751
$349,000125 Days on yellowkey MLS ID: O6388276
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 816 Built: 1969 Tax: $3,419 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$3,419
Remarks: This luxury condominium is in the established complex of Lake Maitland Terrace which sits on the shores of Lake Maitland, Winter Park Chain of Lakes. This immaculately maintained complex includes 11, 2-story, mid-century modern buildings sprawled across several acres, creating beautiful green space and picturesque views across the lake. This unit is special. A complete renovation with every detail accounted for, it is turnkey with enduring design. Warm wood floors are carried through spaces, kitchen has been opened to living room and flanked with windows allowing natural light to shine. Kitchen features white 42-inch shaker style cabinetry, quartz counters, subway tile backsplash, open shelving and stainless appliances. Counter seating is inviting and creates great kitchen function with loads of counter space for the aspiring chef. Primary suite is spacious with large closet storage, and renovated bath. Secondary bedroom and additional bath add to the flexibility of the unit, a guest room or home office. Indoor laundry makes this lock-and-go lifestyle even more appealing. Custom window treatments, closet system storage, updated HVAC, and fresh paint throughout. The location is pristine with walkability to the Enzian independent theatre, Lake Lily Park with a recreational trail and park, and home to community events, many restaurants and more. A short distance to Winter Park Village and Park Avenue and zoned for incredible schools with Dommerich Elementary, Maitland Middle & Winter Park Highschool. Complex is amenity-rich with sidewalks, community pool, generous dock, shuffleboards and more. Make this rare opportunity yours to own a little slice of this Maitland treasure.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
1994 KENASTON RD #1994, MAITLAND, FL 32751
$399,000174 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
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)
987 BRIGHTWATER CIR, MAITLAND, FL 32751
$1,100,00076 Days on yellowkey MLS ID: O6401747
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3270 Built: 1996Monthly Fee: $395 Tax: $12,450 (2025)Community: Maitland ClubSpa: YesSingle Family
Taxes:$12,450
Remarks: Your dream home awaits. Welcome to this exquisitely Renovated 4/4 PLUS OFFICE PLUS BONUS ROOM POOL HOME. Located in the gorgeous guard gated enclave of Maitland Club. From the moment you enter, soaring ceilings and an elegant 3-way split floor plan create a sense of openness and refined comfort. At the heart of the home lies a beautiful updated kitchen, complete with a spacious center island, induction cooktop, and newer appliances - seamlessly flowing in to the sunlit breakfast nook and invitation family room, where a gas fireplace adds warmth and charm. All of these living spaces overlook a breathtaking outdoor retreat featuring a sparkling oversized swimming pool, perfect for both quiet relaxation and lively entertaining. Designed with versatility in mind this 3 way split plan has an upstairs bonus room with a full bath, - ideal as a playroom, home theater, exercise room or even a combination of spaces due to it's large size. Set on a generous one-third acre lot, the property offers ample room for outdoor enjoyment, from a potential playground to a thoughtfully designed lanai with dedicated areas for dining and lounging. Every corner of this home invites you to linger and enjoy. Ideally located near everything you love, this home offers easy access to premier grocery destinations, vibrant shopping and dining, major roadways, perfectly blending luxury with everyday convenience. Just minutes from Whole Foods, Trader Joe’s, Altamonte Mall, and the renowned shops and restaurants along Park Avenue in Winter Park, you’ll enjoy the best of Central Florida living right at your doorstep. Well-maintained home with A/C replaced in 2017. Interior upgrades completed in 2020, including a updated kitchen, newer appliances, new flooring, and three beautifully renovated bathrooms. No pool heater. Homes of this caliber do not last long.... come experience it for yourself.
Listing Agent: Gale Milgrim (407-443-9832)
360 LAKE SEMINARY CIR, MAITLAND, FL 32751
$4,999,000231 Days on yellowkey MLS ID: O6362152
Bed: 5 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 6466 Built: 2026 Tax: $3,536 (2024)Community: FloridahavenSpa: YesSingle Family
Taxes:$3,536
Remarks: Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Mel Bernstein (407-810-4726)
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