Location: Maitland
Do Not Show Listings
601 ORANOLE RD, MAITLAND, FL 32751
$385,900330 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,216
Elementary School: Lake Orienta Elementary
High School: Lyman High
Tax Year: 2024
Middle School: Milwee Middle
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)
210 ALPINE DR, MAITLAND, FL 32751
$527,30063 Days on yellowkey MLS ID: O6395056
REDUCED by $22,700 (4.1%) on 05/12/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1328 Built: 1950 Tax: $7,052 (2025)Community: Sunset RidgeSingle Family
Taxes:$7,052
Elementary School: Dommerich Elem
High School: Winter Park High
Tax Year: 2025
Middle School: Maitland Middle
Remarks: Don't miss this Great opportunity in the Maitland-Winter Park area! There's Potential for Renovation, Expansion or Development with this property. Imagine the Improvements that can be made for the Future. This is a One Owner Home held be the same family since the 1960s. New roof in 2022. The adjacent property at 220 Alpine is also available for purchase.
Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)
Listing Agent: Beth Hathaway (407-314-1300)
220 ALPINE DR, MAITLAND, FL 32751
$427,40089 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
Elementary School: None
High School: None
Middle School: None
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.
1501 DRUID ISLE RD, MAITLAND, FL 32751
$824,00077 Days on yellowkey MLS ID: O6389520
REDUCED by $26,000 (3.1%) on 04/28/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 3000 Built: 1971 Tax: $11,716 (2025)Community: Druid IsleSingle Family
Taxes:$11,716
Remarks: Lease option considered. LAKESIDE LIVING in Maitland, Florida! Nestled canal front with direct access to Lake Charity, this vintage block home is built like a fortress with all the modern luxuries of today. A unique home for those who desire authenticity in both design and quality. A side entry garage leads to a courtyard like entrance with a marble path and asian influenced landscape. Double doors open into an expansive footprint with 3 large bedrooms, 2 baths and over 3,000 sq ft of living space. A 42 x 12 sunroom overlooking the water pays homage to the nostalgic Florida charm of this decade. No expense was spared when renovating this interior. Luxurious finishings and professional installation can make all the difference! Especially noted in the kitchen and baths! Upon entering, a Balsato Beige Porcelain fireplace surround wall anchors the space with plenty of areas to create conversational seating, a designer’s dream! The kitchen island is open to the entire living space with tons of storage and a double waterfall edge in Taj Mahal Quartzite. The perimeter counters are done in beautiful Bora Bora Quartz by Sharifstone. Real wood cabinetry in white dove compliments the earth tones giving a more transitional than modern vibe. Brushed gold hardware, lighting & plumbing fixtures are the perfect “jewelry” for the space! All new high end appliances convey. A brick fireplace graces the dining/living room wall (sounding like a song), yet another functional design opportunity to really create a home that works for YOU. There’s plenty of spots for an office, although not formally mentioned and the ability to use some of the square footage to create an additional “room” if needed. The primary suite closet takes the cake with all the fun features a dream closet should have! The ensuite bath has a lovely vanity with Quartz tops, dual sinks and a gorgeous shower with designer tile and a frameless glass door. Hardware is all in a matte black. The additional 2 bedrooms share a bath that has also had a complete remodel! This home is move in ready with a timeless style throughout. Flooring is a cohesive blend of tile and luxury vinyl plank. New roof 2024. With ideal proximity to fine dining & shopping in Maitland, Winter Park’s infamous Park Avenue and the Theme Parks, you’ll find yourself “staycationing” a little more often!
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Autumn Makin (352-455-0044)
221 MINNEHAHA RD, MAITLAND, FL 32751
$1,489,00018 Days on yellowkey MLS ID: O6406760
1 Days Off yellowkey (back on 5/21/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3797 Built: 1957 Tax: $11,067 (2025)Community: Packwood SubSpa: YesSingle Family
Taxes:$11,067
Elementary School: Lake Sybelia Elem
Remarks: Under contract-accepting backup offers. A rare opportunity on one of Maitland’s most coveted cul-de-sac streets, where custom estates line a quiet neighborhood bordering the Winter Park Chain of Lakes, this stunning Mediterranean estate offers the privacy of a secluded retreat while placing you just moments from Maitland City Centre, Publix & the area’s vibrant dining and shopping scene. Completely reimagined in 2007 w/ a 2,000+ SF addition, including a new façade, expansive covered front porch & 2-car garage, this 4-bedroom, 3-bath home offers 3,797 SF of beautifully renovated living space on a fully fenced 0.35-acre lot. A paver circular drive welcomes guests, while the arched covered entry sets the tone for the character found throughout. Inside, the foyer offers a gracious arrival w/ a custom built-in library, wood floors & a wood-burning fireplace w/ brick surround. The dining room flows seamlessly to a well-appointed butler’s pantry & wet bar with second dishwasher, beverage refrigerator & sink. Both the dining room and kitchen open to the spacious and comfortable family room, creating exceptional flow for everyday living & entertaining. The kitchen features a Dacor 6-burner professional gas cooktop, GE Monogram double wall ovens with warming drawer, honed oversized black granite countertops, 42” wood cabinetry, travertine floors, designer lighting & an oversized island with seating for four or more. A generously sized eat-in area provides comfortable casual dining, while the adjacent family room features tall ceilings, extensive millwork, decorative wood beams & French doors overlooking the backyard oasis. Privately positioned on the opposite side of the home, the primary suite is a true sanctuary w/ two organized walk-in closets, back porch access & a renovated spa bath featuring a freestanding soaking tub, frameless glass shower & beautifully appointed vanity. Located near the primary suite on the main level, a versatile second bedroom sits across the hall from a full bath and works well as a guest suite, office, nursery or fitness room. The first floor is further enhanced by an exceptional media room with platform theater-style seating & surround sound set up, along w/ a large laundry room featuring exceptional storage & a second-floor laundry chute. Upstairs, two generous bedrooms w/ decorative beamed ceilings & ample closets share a Jack-and-Jill bath w/ jetted tub, while the rear bedroom opens to a deep balcony overlooking the grounds. Outside, the fully fenced lot delivers a resort-like setting with sparkling pool, covered porch w/ a tongue and groove ceiling, open entertaining deck & mature landscaping designed for both privacy and enjoyment. A rear gate offers direct access to Maitland City Centre, the farmers market, restaurants, retail & grocery just three blocks away. New roof w/ skylight 2021. Three upgraded HVAC systems 2021–2023. Twenty-five new double-pane, Low-E, argon-filled window, double-strength glass currently in progress & expected to be completed by the end of May. Satisfactory 4-Point Inspection and professional measurement completed May 2026. Offering exceptional privacy, generous living spaces & a remarkably walkable location, this is your opportunity to own a beautifully updated home in one of Maitland’s most desirable neighborhoods, zoned for highly regarded Winter Park High School & convenient to Orlando Avenue, Minnehaha Park, Lake Lily, Fort Maitland, and less than ten minutes from the shops and restaurants of Winter Park's Park Avenue.
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Padgett Mccormick (407-645-4321)
1761 TIPPICANOE TRL, MAITLAND, FL 32751
$729,00025 Days on yellowkey MLS ID: O6405841
REDUCED by $30,000 (4.0%) on 05/21/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2066 Built: 1964Monthly Fee: $17 Tax: $5,026 (2026)Community: Dommerich Ests 1St AddSingle Family
Taxes:$5,026
Tax Year: 2026
Remarks: Welcome to 1761 Tippicanoe Trail, a beautifully maintained home nestled on a quiet, tree-lined street in one of Maitland’s most desirable neighborhoods. This inviting residence blends timeless charm with thoughtful updates, offering comfort, style, and an exceptional location. Step inside to find warm and welcoming living spaces filled with natural light, spacious gathering areas, and a functional layout ideal for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the dining and family areas, creating an easy and comfortable lifestyle. The home features comfortable bedrooms, including a peaceful primary suite with a newly remodeled primary bathroom designed with modern style and convenience in mind. Additional updates include a newer AC system that is only one year old, providing peace of mind and energy efficiency. Enjoy Florida living year-round with a private backyard perfect for relaxing or hosting guests. Residents also enjoy deeded lake access, adding even more appeal to this special Maitland property. Don't miss the virtual walk through and floor plan sketch. Located in a great school district and just minutes from Park Avenue, beautiful parks, shopping, dining, and major roadways, this home offers the perfect combination of location, lifestyle, and value. Don’t miss the opportunity to make 1761 Tippicanoe your next home.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Jeff Clark (407-733-0773)
140 WIGWAM PL, MAITLAND, FL 32751
$629,90041 Days on yellowkey MLS ID: O6401560
REDUCED by $20,000 (3.1%) on 05/14/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2236 Built: 1957 Tax: $3,978 (2025)Community: Dommerich EstatesSingle Family
Taxes:$3,978
Remarks: One or more photo(s) has been virtually staged. Tucked away on a cul-de-sac in beautiful Maitland, this 3-bedroom, 3-bath home with a bonus room offers space, comfort, and privacy on a generous 1/3-acre lot. With 2,236 square feet of living space and a 2-car garage, the home features an updated kitchen and upgraded bathrooms, blending modern touches with everyday functionality. Enjoy cozy evenings by the fireplace or relax in the bright sunroom overlooking the fully fenced backyard with a concrete wall for added privacy. A screened-in porch provides the perfect spot to enjoy Florida living year-round. Homeowners have access to Lake Minnehaha and by the way of the Winter Park chain of lakes, Lake Maitland. Access can use for boat launch or watercraft, dock for fishing, picnic area, kayak storage. It’s only $200 year annually. Only $100 year if no boats or watercraft privileges needed. This home’s prime location in Maitland provides easy access to top-rated schools, parks, shopping, dining, and major highways, making it both a peaceful retreat and a convenient base for daily living!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Blake Bolton (407-318-0361)
747 N LAKE SYBELIA DR, MAITLAND, FL 32751
$3,895,00021 Days on yellowkey MLS ID: O6406879
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 5347 Built: 2023 Tax: $23,099 (2025)Community: Sybelia Shores Second AddSpa: YesSingle Family
Taxes:$23,099
High School: Edgewater High
Remarks: Welcome to 747 N Lake Sybelia Drive, an extraordinary lakefront estate gracefully positioned along the desired northern shoreline of beautiful Lake Sybelia. Completed in late 2023, this breathtaking California Coastal-inspired residence spans 4,755 square feet on an expansive 0.76-acre homesite, blending timeless architecture with refined finishes to create a lifestyle defined by elegance, comfort and effortless lakefront living. Ideally situated on a gently sloping lot, the home captures stunning elevated views of the water, offering a rare sense of privacy, tranquility and perspective. Thoughtfully designed interiors are filled with natural light and crafted for everyday living and exceptional entertaining. The main level showcases a beautifully appointed chef’s kitchen anchored by an oversized island and complemented by a spacious walk-in butler’s pantry. Open-concept dining and living spaces are framed by picturesque lake views, while the expansive great room seamlessly connects indoor and outdoor living. A private office, guest suite and dedicated pool bath complete the first floor. Upstairs, a versatile loft and homework nook provide flexible living space, while two en-suite bedrooms and a serene primary retreat offer exceptional comfort and privacy. The luxurious primary suite and one secondary bedroom open to a spacious lakeside balcony, an idyllic place to enjoy morning coffee, evening sunsets and sweeping water views. Exceptional outdoor living spaces surround the home. A welcoming covered front porch offers the perfect vantage point to enjoy lake views and watch boating activity, while the expansive rear covered lanai is designed for year-round entertaining with a summer kitchen and generous space for lounging and dining. Overlooking the beautifully landscaped backyard, complete with bamboo-lined fencing for privacy, is a sparkling saltwater pool and spa by Titan Pools, thoughtfully designed for resort-style enjoyment and capable of both gas and electric heating. Uniquely embraced by water and recreation, the home enjoys tranquil lake vistas to the south and the stunning pool retreat to the north. The waterfront experience is elevated by a newly constructed composite dock with a heavy-duty dual-motor lift, while a thoughtfully designed shell-base boat ramp provides seamless, eco-conscious access for launching watercraft directly from your property. Adding even more versatility, a 500+ square-foot unfinished bonus room above the garage offers incredible potential for customization, ideal for a media room, guest retreat, fitness studio or creative space. Plumbing has been extended for a future bath or bar, and the space is currently enjoyed as a golf simulator. Car enthusiasts will appreciate the impressive four-car tandem garage featuring soaring 15-foot ceilings designed to accommodate vehicle lifts, premium wall-mounted jackshaft openers for maximum overhead clearance and a separate side-access bay ideal for golf cart storage. Engineered for longevity as much as luxury, the home features an extensive stormwater drainage system with hard-piped gutters designed to protect the land and prevent erosion. Ideally located, enjoy a short visit or golf cart ride to Maitland City Centre and Homer Hough Park at Sybelia Point, while the shopping and dining of Park Avenue are just minutes away. Convenient access to Interstate 4 and express lanes ensures effortless travel throughout the greater Orlando area.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Mick Night (407-629-4446)
1000 S ORLANDO AVE #B25, MAITLAND, FL 32751
$332,50075 Days on yellowkey MLS ID: O6391679
1 Days Off yellowkey (back on 5/18/2026)
REDUCED by $2,500 (0.7%) on 05/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 952 Built: 1964 Tax: $2,559 (2025)Community: Maitland Harbour AptsCondo
Taxes:$2,559
Remarks: Under contract-accepting backup offers. Offered at a newly improved price, this highly desirable residence at Maitland Harbour is located within a boutique 38-unit lakefront condominium community nestled in the heart of Maitland. Ideally positioned on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—this intimate and picturesque enclave offers access to the entire chain and a truly exceptional waterfront lifestyle. A hidden gem, Maitland Harbour blends timeless Mid-Century Modern architecture with the serenity of lakefront living. Designed by renowned architect Manfred Lopatka, a protégé of Frank Lloyd Wright, and built in 1964, the community reflects a distinctive Central Florida interpretation of classic modernist design. Inside this beautifully updated 2-bedroom, 2-bath residence offering 952 square feet, you will find light-filled living space with a clean, cohesive aesthetic throughout. The kitchen, renovated in 2020, features quartz countertops, a subway tile backsplash, open wood shelving, and a pass-through to the dining area, creating both functionality and visual connection to the main living space. The open-concept living and dining areas are bright and inviting, with warm-toned wood flooring and neutral finishes. The primary suite is a true retreat, complete with updated flooring (2020), soft natural light, newly added barn-style closet doors for improved storage access, and direct access to the private balcony—ideal for enjoying morning coffee or evening breezes. The en-suite bath, renovated by a previous owner, features neutral finishes and a glass-enclosed shower. The secondary bedroom is spacious and offers consistent updated flooring and fresh paint, and is located adjacent to a full guest bath with recent updates including vanity, lighting, and fixtures. Additional improvements include a new refrigerator (2023), new windows (2024), new HVAC (2025), and fresh interior paint (2025/2026). The community has completed major improvements including new roofs, pool enclosure, and exterior paint, and both the milestone inspection and structural integrity reserve study have been completed and are available for review. Residents enjoy a full suite of lakefront amenities including a waterfront pool, courtyard, boat slips, fishing pier, kayak storage, community room, private storage, covered parking, and an expansive entertaining deck overlooking Lake Maitland. The location is adjacent to historic Fort Maitland Park and directly across from Lake Lily, the heart of Maitland’s Cultural Corridor, known for concerts, the Maitland Art Festival, and the Sunday Farmers Market, and is just a short walk to the Enzian Theater and local dining, with easy access to Winter Park’s Park Avenue offering premier shopping, restaurants, museums, and year-round events. Enjoy low-maintenance lakefront living with beautiful interior spaces, a private balcony, and access to one of Central Florida’s most sought-after waterfront settings.
653 GREEN MEADOW AVE, MAITLAND, FL 32751
$518,00032 Days on yellowkey MLS ID: O6402661
REDUCED by $10,000 (1.9%) on 05/18/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1909 Built: 1970 Tax: $1,992 (2024)Community: Forest Brook 3Rd SecSingle Family
Taxes:$1,992
Elementary School: English Estates Elementary
High School: Lake Howell High
Middle School: South Seminole Middle
Remarks: One or more photo(s) has been virtually staged. Location, Location, Welcome to your new 4 BED 2 BATH home tucked away on a quiet cul-de-sac street in the desirable Maitland community of "Forest Brook" This one-of-a-kind home offers the perfect blend of charm, space, and functionality. Lovingly maintained, the home welcomes you with a grand Foyer, Formal Living and Dinng rooms, open family room, ideal for gatherings. A new updated Chef's Kitchen, complete with a gas range, beautiful Cherry cabinets, new appliances, and new Quartz countertops. The spacious Florida Room has a fun step up bar with pass through access to the kitchen. Perfect for entertaining and offers its own AC/Heater unit. Step outside to the large wrap around Deck. Tons of space for outdoor entertaining. No neighbors behind you, just tons of conservation space. Additional upgrades include Roof-2021, AC-2023-Fl Room, AC-2025, Gas Water Heater-2010, Kitchen appliances 2023, Electrical panel- 2024. This home is ideally located just minutes from Winter Park, Casselberry, Winter Springs, Easy access to shopping, dining, and major commuter routes. Start living your Best Life.
Listing is courtesy of: A+ REALTY PROFESSIONALS, INC (407-702-5243)
Listing Agent: Darlene Chance (407-247-2307)
1275 LAKE SHADOW CIR #13206, MAITLAND, FL 32751
$145,500104 Days on yellowkey MLS ID: O6383068
REDUCED by $12,000 (7.6%) on 05/18/2026
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. 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. Mortgage savings may be available for buyers of this listing.
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Trevin Perez (305-793-6807)
1750 POCAHONTAS PATH, MAITLAND, FL 32751
$639,00064 Days on yellowkey MLS ID: O6394358
REDUCED by $20,000 (3.0%) on 05/04/2026
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. 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)
755 WOODSIDE RD, MAITLAND, FL 32751
$999,99934 Days 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 and minutes from Winter Park without the WP price tag! 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. UTITLITIES $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)
416 BANYON TREE CIR #206, MAITLAND, FL 32751
$117,90054 Days on yellowkey MLS ID: O6394980
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 658 Built: 1973Monthly Fee: $256 Tax: $1,736 (2024)Community: Carrington Park A CondoSpa: NoCondo
Taxes:$1,736
Remarks: Discover this beautifully maintained 1-bedroom, 1-bath condo in the highly desirable Banyan Tree Condominium of Maitland. Located on the second floor, this unit boasts abundant natural light, a functional layout, and low-maintenance living—perfect for families, first-time buyers, or savvy investors seeking rental income. Enjoy affordable HOA fees ($255.86/month) covering building insurance, pool, landscaping, and common areas. Situated in Seminole County, close to top-rated schools, shopping, dining, and major highways. Flood Zone X, no CDD, not currently homesteaded. This is an exceptional opportunity to own a comfortable home or a turnkey investment property. Act now—buyer to verify all information including school zoning, rental restrictions, and flood insurance requirements.
Listing is courtesy of: NEXUS INTERNATIONAL REALTY (305-301-3861)
Listing Agent: Yuleana Gil Abreu (561-564-1436)
1175 LAKE SHADOW CIR #4308, MAITLAND, FL 32751
$234,000194 Days on yellowkey MLS ID: O6361097
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1372 Built: 2000 Tax: $3,355 (2024)Community: Visconti WestSpa: NoCondo
Taxes:$3,355
Remarks: Experience true resort-style living at its finest in this lovely 4-bedroom, 2-bath condominium in the beautiful, gated community Visconti West. As you enter the home, you are welcomed by an open and spacious floor plan filled with abundant natural light, vaulted ceilings and decorative cutouts. Enjoy a split-plan layout that offers comfort and privacy for family and guests. The kitchen features a breakfast bar, track lighting, kitchen appliances, pantry closet and a separate inside laundry space for convenience. Step out onto your private balcony from the main living space and take in the breathtaking water views, perfectly positioned for stunning sunsets – your own peaceful retreat at the end of the day. The primary bedroom offers stunning water views, a private bath and walk in closet. Guest bedrooms are spacious and are light and bright. This highly sought-after community offers exceptional amenities, including a resort-style lakefront pool, dock, walking trails with lake views, state-of-the-art fitness center, clubhouse, tennis & pickleball court, basketball court, and a recreational playground—providing something for everyone to enjoy. It is conveniently located in the heart of Maitland, close to Maitland Ballfield Complex, Genesis Sporting Complex and minutes from downtown Winter Park. Easy access to all major highways, restaurants, retail and shopping. This home is perfect for those who are seeking a low-maintenance lifestyle. Schedule your showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Julie Ruh (407-587-9654)
628 WOODLEY RD, MAITLAND, FL 32751
$429,90026 Days on yellowkey MLS ID: O6405045
1 Days Off yellowkey (back on 5/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1697 Built: 1959 Tax: $1,767 (2025)Community: Oakland Shores 1St AddSingle Family
Taxes:$1,767
Remarks: Under contract-accepting backup offers. Welcome to life in one of Maitland’s most desirable established neighborhoods, located in Seminole County and known for its strong schools, friendly community, and convenient access to everything Central Florida. Just minutes from beautiful lakes, local restaurants, shopping, and the interstate for an easy commute, this home offers the perfect blend of comfort, connection, and lifestyle. Step inside to an inviting open-concept layout filled with natural light, creating a bright and airy feel throughout. The heart of the home is a brand new custom-designed gourmet kitchen, thoughtfully finished and ideal for both everyday living and entertaining. Bamboo flooring and stunning terrazzo details gives the home a timeless mid-century modern feel with warmth and character. Enjoy the added flexibility of a Florida room, perfect for a home office, playroom, or additional living space. A garage and a carport, along with abundant storage throughout maximizes the space. The outdoor area is designed for hosting and gathering, featuring new sod and plenty of room to relax or entertain. Major updates include a 2024 HVAC, 2025 water heater, and new piping. Schedule your private showing today! This one won’t last long.
Listing is courtesy of: CENTRAL FLORIDA REALTY EXPERTS (407-542-4403)
Listing Agent: Kelly Althof (941-962-9933)
2570 DERBYSHIRE BLVD, MAITLAND, FL 32751
$545,000122 Days on yellowkey MLS ID: O6378592
2 Days Off yellowkey (back on 5/13/2026)
REDUCED by $10,000 (1.8%) on 04/20/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1857 Built: 1964 Tax: $1,891 (2024)Community: English Estates Unit 2Single Family
Taxes:$1,891
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 2570 Derbyshire Blvd, a fully transformed 4-bedroom, 3-bathroom Maitland pool home where modern design meets effortless Florida living. This top-to-bottom renovation delivers both style and tranquility, featuring a brand-new 2026 roof, all-new windows, and a newly refinished pool. Inside, the heart of the home is the stunning designer kitchen with quartz countertops, brand-new soft-close cabinetry, and a sleek, open layout that flows seamlessly into the main living and dining areas. All three bathrooms have been completely updated with modern finishes and a comfortable feel. The flexible floor plan offers four spacious bedrooms, perfect for families, guests, or a home office. Step outside to your private backyard retreat and enjoy the freshly refinished pool and shaded yard perfect for relaxing or hosting year-round in the Florida sun. Don't miss out on the chance of making this house your home!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Nelson Folchini (617-775-3581)
868 TOWN CIR #123, MAITLAND, FL 32751
$260,00025 Days on yellowkey MLS ID: O6406031
0 Days Off yellowkey (back on 5/12/2026)
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1565 Built: 1979Monthly Fee: $425 Tax: $1,811 (2025)Community: Park Lake Twnhs Ph 02Condo
Taxes:$1,811
Remarks: This is the kind of first home that makes life easier. With over 1,500 SqFt, 3 bedrooms, 2.5 baths, and thoughtful updates throughout, this Maitland condo gives you room to grow without the heavy upkeep of a single family home. The remodeled kitchen features quartz counters, stainless steel appliances, and updated cabinetry, while downstairs tile flooring keeps maintenance simple. Enjoy a large dining area, separate living room, laundry room, enclosed patio, and attached garage. Upstairs, the spacious primary suite opens to a balcony overlooking the courtyard. The community pool, lake access, and HOA covered exterior maintenance add even more value, all in a location close to Maitland favorites, Winter Park, and downtown Orlando.
Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)
Listing Agent: Myriam Balthazar (941-445-1019)
200 SPARTAN DR, MAITLAND, FL 32751
$525,00063 Days on yellowkey MLS ID: O6394981
REDUCED by $15,000 (2.8%) on 05/12/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1830 Built: 1962 Tax: $5,197 (2025)Community: Cool-More SubSingle Family
Taxes:$5,197
Remarks: More photos to come soon! Welcome to 200 Spartan Dr, a beautifully updated 3/2 (with bonus room and large laundry room) pool home in the heart of Maitland. The interior has been thoughtfully opened up by removing walls between the living area and kitchen, creating a much more spacious and modern feel, and a large island was added to make the kitchen the center of the home. The home also features a bonus room offering great flexibility for a home office, workout space, or hobby room. Outside, enjoy a private pool and backyard space perfect for relaxing or entertaining. Conveniently located near shopping, dining, parks, and major roadways, this home offers comfort, functionality, and a great Maitland location. Roof, HVAC, and Water heater from 2018.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Nick Mandiola (407-453-0190)
1100 S ORLANDO AVE #306, MAITLAND, FL 32751
$649,00073 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)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.