Location: Maitland
Do Not Show Listings
987 BRIGHTWATER CIR, MAITLAND, FL 32751
$1,100,0005 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,450
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Tax Year: 2025
Middle School: Maitland Middle
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 is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Gale Milgrim (407-443-9832)
1776 BOBTAIL DR, MAITLAND, FL 32751
$524,99920 Days on yellowkey MLS ID: G5110747
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
Middle School: Lockhart Middle
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)
210 ALPINE DR, MAITLAND, FL 32751
$550,00029 Days on yellowkey MLS ID: O6395056
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
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)
1501 DRUID ISLE RD, MAITLAND, FL 32751
$824,00043 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
Elementary School: None
High School: None
Middle School: None
Remarks: 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)
2040 GERONIMO TRL, MAITLAND, FL 32751
$799,00048 Days on yellowkey MLS ID: O6390221
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2375 Built: 1963 Tax: $3,301 (2025)Community: Highland Park EstsSingle Family
Taxes:$3,301
Remarks: Set on one of the most sought-after streets in Dommerich, this completely renovated home combines the solid construction of a 1963 block home with thoughtful modern updates throughout. From the moment you arrive, the circular driveway, classic brick accents, and welcoming front porch set the tone. Inside, a bright foyer opens to beautiful solid maple wood floors and a light, airy feel that carries throughout the home. To the right, the formal living room features built-in shelving and a striking brick wood-burning fireplace, while the adjoining formal dining room connects directly to the kitchen and can be closed off with pocket doors if you want a little separation. The eat-in kitchen is truly the heart of the home, showcasing rich solid cherry cabinetry, unique man-made glass countertops, a large farmhouse sink, and top-of-the-line stainless Bosch appliances including a built-in oven and gas cooktop. A generous peninsula overlooks the oversized family room, where French doors open to a stunning Florida room that fills the home with natural light. This space is a showstopper—large, lined with windows, and finished with soaring shiplap ceilings—creating the kind of room you’ll use year-round, with direct access to the backyard. The primary suite is spacious and refined with crown molding, a built-in closet plus a walk-in, and a beautifully renovated bath featuring matching glass countertops, a Kohler vanity, and a glass shower with both a large rain head and handheld fixture. Two additional bedrooms are generously sized and share an updated hall bath with a large vanity, classic subway tile, and a soaking tub. The interior also includes a well-equipped laundry room with cabinetry, a cedar storage closet, and access to the two-car garage. Out back, the fully fenced private yard offers plenty of room for entertainment, recently re-sodded with irrigation and enclosed with a brand new wood fence installed in 2025—leaving ample space for a future pool or patio if desired. Additional upgrades include smooth flat ceilings with recessed lighting throughout, new drywall, plantation shutters, updated windows and doors, and an energy-efficient hybrid water heater. Beyond the home itself, the location is hard to beat—just a short walk to Dommerich Elementary, Maitland Middle School, and Maitland Community Park offering tennis courts, indoor racquetball, and playgrounds. Zoned for highly regarded Winter Park High School. Call today to schedule your private showing!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Maria Van Warner (407-256-8066)
1281 WELLINGTON TER, MAITLAND, FL 32751
$979,0009 Days on yellowkey MLS ID: TB8499961
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2931 Built: 1985Monthly Fee: $48 Tax: $6,219 (2024)Community: WellingtonSingle Family
Taxes:$6,219
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: South Seminole Middle
Remarks: Beautiful and spacious home at 1281 Wellington Terrace featuring high beam ceilings and elegant tile floors throughout. The open layout offers wonderful natural light and two master bedrooms, perfect for flexible living. New windows add comfort and efficiency. Enjoy a private, low-maintenance backyard ideal for relaxing or entertaining. Located in a beautiful neighborhood just minutes from Winter Park shopping and dining, with easy access to I-4 for convenient commuting.
Listing is courtesy of: LISTED SIMPLY (800-995-5879)
Listing Agent: Sinan Zakaria (800-995-5879)
250 ORANGE PL, MAITLAND, FL 32751
$325,00062 Days on yellowkey MLS ID: O6384786
0 Days Off yellowkey (back on 4/27/2026)
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 564 Built: 1940 Tax: $3,885 (2025)Community: Orangedale Park RepSingle Family
Taxes:$3,885
Remarks: Under contract-accepting backup offers. Welcome to 250 Orange Place, This charming bungalow in an unbeatable location just two blocks from Winter Park. This well-maintained one-bedroom cottage features a welcoming rocking-chair front porch, attractive kitchen, clawfoot bathtub, indoor laundry room, and one-car garage with additional off-street parking. Enjoy a shaded, hammock-ready backyard perfect for relaxing. Walk the tree-lined streets to the Enzian Theatre, Fort Maitland Park, and Park Avenue, or head minutes away to Whole Foods and Winter Park Village via Hwy 17-92. A rare opportunity to own a character-filled home in a highly walkable and convenient location.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
361 HICKORY DR, MAITLAND, FL 32751
$349,00027 Days on yellowkey MLS ID: O6395765
REDUCED by $20,000 (5.4%) on 04/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1407 Built: 1959 Tax: $2,679 (2024)Community: Druid Hills ParkSingle Family
Taxes:$2,679
Elementary School: Lake Orienta Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to 361 Hickory Drive, a truly special opportunity in a quiet, well-established community in the heart of Maitland. This charming home offers the perfect blend of comfort, mid-century historic charm and an unbeatable location making it ideal for those seeking both tranquility and convenience. Set on an oversized lot, this property provides ample space to entertain or enjoy the peaceful surroundings. The neighborhood is known for its quiet atmosphere with NO HOA, giving you the freedom to truly make this home your own without added restrictions. Upon walking in, you are greeted with an open concept living room space with the dining room to the left. The kitchen features ample cabinet space and a separate cooktop. The 2nd and 3rd bedrooms are generously sized with the primary including an en-suite bathroom. A BRAND NEW ROOF will be installed prior to closing, offering peace of mind. Upgrades include a New Water Heater (2026) and A/C(2019) ensuring comfort and efficiency. This home is also zoned in Top Rated Seminole County School Districts. Whether you're looking to settle into a serene neighborhood or invest in a property with strong fundamentals, this one checks all the boxes. Don’t miss your chance to call this Maitland gem home today!
Listing Agent: Emma Nelson (224-703-9190)
1170 WILLOWBROOK TRL, MAITLAND, FL 32751
$759,00021 Days on yellowkey MLS ID: O6396754
0 Days Off yellowkey (back on 4/26/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2159 Built: 1966 Tax: $4,455 (2025)Community: Maitland WoodsSpa: NoSingle Family
Taxes:$4,455
Remarks: Towering oaks and Spanish moss flowing in the breeze set the stage for this oasis in the heart of Maitland. This charming 4 bedroom, 2 bath abode with a tropical courtyard pool has been lovingly updated with luxe finishes and features. Step inside the covered airy breezeway where travertine pavers surround the screen enclosed pool deck and the true front door entrance. Beautiful crown moulding and wood-look ceramic tile flooring runs throughout the house (no carpeting). Double pane windows and sliders with build-in blinds accent the courtyard views. Arched doorways open to the poolside family room with wood-burning marble-surround fireplace and custom built-ins. Large enough for all your family and friends, the spacious living and dining rooms with custom window shutters and recessed lighting is sure to impress. Total kitchen remodel features handmade subway tile backsplash, quartz countertops, stainless steel appliances, and the most charming in-kitchen dining area with views out to the pool. A renovated full hall bathroom with double sink quartz vanity and tub/shower combo opens to the pool and is close to the 3 guest bedrooms (one bedroom also has sliders to the pool). Your large primary suite is tucked away at the back of the house with dressing area, walk-in closet, and separate toilet/shower room. And the views to the pool through the double sliders are inspiring. Indoor/outdoor living is a breeze in this unique Maitland courtyard style pool home. Plus, a fully fenced backyard is still big enough for children and pets to play. You’ll love the location with easy access to I-4, the shops and restaurants of Downtown Maitland and Lake Lily (home of a weekly farmer’s market), and walking distance to Lake Sybelia and lakefront Homer Hough Park. Improvements include NEW hot water heater 2026; NEW solar pool heater 2022; NEW paver driveway and motor court 2022; NEW roof 2021; NEW travertine pool deck 2021; NEW HVAC 2020; NEW Gernerac house generator; and Replumb CPVC 2015.
Listing Agent: Steven Ritz (321-277-8271)
1001 VERSAILLES CT, MAITLAND, FL 32751
$1,050,0004 Days on yellowkey MLS ID: O6401795
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3625 Built: 1981Monthly Fee: $29 Tax: $6,161 (2025)Community: VersaillesSingle Family
Taxes:$6,161
Remarks: One or more photo(s) has been virtually staged. Nestled within the quiet, established community of Versailles, this exceptional residence invites you to slow down and savor the good life. Offering over 3,600 sq. ft., this home features 4 spacious bedrooms and 3 full baths, with a layout that is both functional and flexible. The PRIMARY SUITE is conveniently located on the MAIN FLOOR and features an EXPANSIVE ATTACHED OFFICE, CRAFT ROOM OR SITTING ROOM—perfect for today’s lifestyle. This generous space also presents a unique opportunity for reconfiguration, allowing you to expand the primary bedroom and/or create a truly luxurious bath retreat tailored to your vision. Upstairs, three additional BEDROOMS ARE IMPRESSIVELY SIZED, offering plenty of room for family or guests. A STANDOUT FEATURE of the home is the BONUS ROOM with its own private entrance, located just off the rear garage—ideal for a game room, media lounge, or entertainment hub complete with space for a pool table, ping pong table, and a large-screen TV. At the heart of the home, the EXPANSIVE 23 x14 kitchen is filled with potential and already equipped with premium appliances, including a SubZero refrigerator, separate SubZero freezer, and a Viking cooktop. Built-in desk space and charming banquet seating create a welcoming spot for casual dining and everyday moments. The inviting family room is designed for cozy evenings, featuring a wood-burning fireplace, beverage fridge, ice maker, and sink—perfect for entertaining or unwinding. For larger gatherings, the expansive living room and adjacent dining area provide an elegant backdrop, whether hosting dinner parties, game nights, or enjoying music by a grand piano. Step outside to your private oasis, set on NEARLY HALF OF AN ACRE of beautifully landscaped grounds. The generous deck surrounds a stunning 10-foot-deep SWIMMING POOL offering endless possibilities for outdoor entertaining, relaxation, and recreation. Life in Versailles extends beyond your front door. HOA Residents can enjoy PRIVATE ACCESS TO LAKE Minnehaha, complete with a dock—perfect for paddleboarding, kayaking, or soaking in breathtaking sunset views. Just beyond the back gate, Maitland Community Park offers an array of AMENITIES including playgrounds, tennis courts, basketball, racquetball, and scenic fitness trails. A convenient paved path even connects you to nearby shopping and dining, including Publix. Ideally located with easy access to Maitland Boulevard, SR 414, I-4, and 436, SUNRAIL station is close and ZONED IN TOP RATED SCHOOLS, this home offers both tranquility and convenience. With an optional HOA, you have the freedom to enjoy the community on your terms. This is more than a home—it’s a lifestyle waiting to be embraced. Make your appointment today to view this lovely home!
Listing Agent: Heather Frazee (321-689-9465)
921 N THISTLE LN, MAITLAND, FL 32751
$1,049,00012 Days on yellowkey MLS ID: R4911080
REDUCED by $51,000 (4.6%) on 04/22/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2300 Built: 1967 Tax: $4,489 (2025)Community: Highland Park EstatesSpa: YesSingle Family
Taxes:$4,489
Remarks: Central location, fully renovated, A-rated schools, a resort-style pool - this Dommerich home checks every box - and it is move-in ready, turnkey for your lifestyle. Situated in one of Central Florida’s most sought-after neighborhoods for over 60 years, Dommerich is known for its top-rated schools, tree-lined streets, parks, and unmatched convenience. This home sits right in the heart of it all. Originally built in 1967 and thoughtfully reimagined in a top-to-bottom renovation completed in 2019, the property blends classic charm with modern design and systems. Major updates include roof, HVAC, plumbing, electrical, windows, doors, insulation, appliances, kitchen, primary wing addition, natural gas connection, and a Rinnai tankless water heater. Inside, the open-concept living and dining spaces flow seamlessly to a designer pool and screened patio, creating an ideal indoor-outdoor lifestyle. The modern kitchen features extensive cabinetry with drawer-based storage, a coffee bar, and easy access to the garage and main living areas. A standout feature is the 2019-built primary suite addition, offering vaulted ceilings, a custom walk-in closet, en-suite bath, laundry, utility closet, and direct access to the pool area. The home also includes a second primary bedroom with its own en-suite bath that doubles as a pool bath, plus two additional bedrooms and a shared hall bath. The curb appeal is anchored by a mature, storybook-style shade tree, setting the tone for the character found throughout the property. Enjoy a short walk to the schools on a secluded sidewalk or take in the open sports fields across the street and Maitland Community park a few streets over.
Listing is courtesy of: VISTA NATIONAL MANAGEMENT INC (407-252-5052)
Listing Agent: Garrett Mcginnis (321-278-9511)
140 WIGWAM PL, MAITLAND, FL 32751
$649,9007 Days on yellowkey MLS ID: O6401560
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. 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)
2809 WAUMPI TRL, MAITLAND, FL 32751
$745,00013 Days on yellowkey MLS ID: O6399820
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2330 Built: 1971 Tax: $6,426 (2024)Community: Dommerich Hills 6Th AddSpa: NoSingle Family
Taxes:$6,426
Remarks: Completely Remodeled 2026 | Single-Story | Split Floorplan | The redesigned kitchen features 42" shaker cabinetry, Calcutta quartz countertops, a marble backsplash, and new stainless steel Fisher & Paykel appliances. Bathrooms have been completely remodeled with updated finishes. Luxury vinyl flooring extends through all common areas, complemented by LED recessed lighting and updated fixtures throughout. The open layout provides clear sight-lines between the kitchen and family room, creating a connected main living area. The pavers meet manicured lawns and fresh landscaping for a clean, contemporary finish that is 100% move-in ready. Additional features include an interior laundry room and a fully fenced backyard with a pool. Enjoy being just minutes from Park Avenue, Lake Lily, and Maitland City Centre where you'll find farmers markets, local dining, and boutique shopping. With easy access to I-4, 417, and the Maitland Exchange, you're well connected to everything Central Florida has to offer.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Farhad Haniff (516-587-2799)
1750 POCAHONTAS PATH, MAITLAND, FL 32751
$659,00030 Days on yellowkey MLS ID: O6394358
REDUCED by $20,000 (2.9%) on 04/21/2026
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)
106 OAKWOOD DR, MAITLAND, FL 32751
$649,90046 Days on yellowkey MLS ID: O6390412
REDUCED by $30,000 (4.4%) on 04/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1877 Built: 1963 Tax: $1,940 (2024)Community: N/ASingle Family
Taxes:$1,940
Remarks: One or more photo(s) has been virtually staged. MAJOR PRICE IMPROVEMENT Fully reimagined designer pool home with deeded access to skiable Lake Seminary, offering a rare blend of modern luxury, privacy, and prime Maitland location. Tucked away in a peaceful setting, this home lives like a private retreat while remaining just minutes from everything Maitland and Winter Park have to enjoy. At the heart of the home is a true showpiece kitchen, thoughtfully designed with a striking waterfall-edge island, full-height quartz backsplash, beverage fridge, and a clean, modern aesthetic reminiscent of a custom build. The open-concept layout is filled with natural light and flows effortlessly into the main living spaces—perfect for both elevated entertaining and everyday living. The primary suite delivers a spa-inspired retreat, featuring a freestanding soaking tub, oversized walk-in shower with dual heads, and carefully curated designer finishes that create a true sense of escape. Step outside to your own private backyard oasis, complete with a sparkling pool, expansive paver patio, and newly fenced yard—designed for both relaxation and hosting. The oversized lot offers exceptional flexibility, with ample space to add a garage, guest house, or additional storage to suit your needs. This home has been fully renovated with a strong emphasis on quality craftsmanship and high-end finishes throughout, including a new roof, HVAC, windows, flooring, and more—offering true move-in-ready peace of mind. Enjoy deeded access to skiable Lake Seminary via recorded easement—an exceptional and increasingly rare feature in this area. Buyer to verify access and use. Conveniently located near Maitland and Winter Park, with easy access to shopping, dining, and major roadways—giving you the perfect balance of privacy and accessibility.
Listing Agent: Kikzeny Cartagena (215-359-6910)
2514 TUSCARORA TRL, MAITLAND, FL 32751
$759,00081 Days on yellowkey MLS ID: O6380728
REDUCED by $20,000 (2.6%) on 04/16/2026
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 3000 Built: 1971 Tax: $4,200 (2025)Community: Dommerich Hills 2 Nd AddSingle Family
Taxes:$4,200
Remarks: To Buyer “Discover the advantage of owning one of Tuscarora Trail’s premier homesites—where space, privacy, and lifestyle come together, all within the highly sought-after Dommerich school district, supporting both today’s living and tomorrow’s resale value. ” Nestled on a serene lakeside setting in the heart of Maitland, this beautifully upgraded 4-bedroom, 2.5-bath home offers more than just square footage—it delivers a lifestyle steeped in comfort, elegance, and Florida charm. Spanning nearly 3,000 square feet on a generous 0.43-acre lot, this residence frames breathtaking lake and sunset views that greet you with every evening breeze. Sunlight dances through expansive glass doors, illuminating open living spaces that flow effortlessly into a resort-style outdoor oasis complete with a sparkling private pool, covered patio, and lush water-framed views—perfect for quiet mornings with coffee or lively gatherings under starlit skies. Inside, thoughtful updates—like fresh interior and exterior paint, major systems enhanced for modern living, and paid-off solar panels for incredibly low utility costs—blend timeless Florida living with smart sustainability. Situated in the highly sought-after Dommerich Elementary and Winter Park school districts, this home embodies both tranquil retreat and everyday convenience. You’re just minutes from the charming boutiques, world-class dining, and cultural attractions of Winter Park’s Park Avenue, and a comfortable drive to Orlando’s theme parks—including Walt Disney World® Resort—and the region’s major airports for effortless travel. Whether you’re hosting family by the pool, savoring sunset reflections on the lake, or enjoying the top-tier schools and vibrant local lifestyle, 2514 Tuscarora Trail is more than a house—it’s home. NO HOA
Listing is courtesy of: NOELKE REALTY (407-607-7166)
Listing Agent: Tom Noelke (407-607-7166)
67 CYPRESS LN, MAITLAND, FL 32751
$1,130,000111 Days on yellowkey MLS ID: O6371328
REDUCED by $95,000 (7.8%) on 04/16/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2292 Built: 1979Monthly Fee: $8 Tax: $4,139 (2024)Community: Maitland ShoresSingle Family
Taxes:$4,139
Remarks: Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths. Step inside to discover hardwood floors flowing throughout the first level, leading to a dramatic sunken living room and formal dining room perfect for entertaining. The heart of the home is the spectacular family room featuring soaring 17-foot ceilings, a wood-burning fireplace, and expansive windows that bathe the space in natural light. The well-appointed kitchen boasts granite countertops, a charming breakfast nook, and glass sliders opening to a covered side porch—ideal for morning coffee or evening relaxation. The main level also includes a convenient guest bedroom and full bath, separate living and dining rooms, plus an attached 2-car garage. Upstairs, retreat to the loft-style primary suite with private en suite bath, two additional guest bedrooms, a hall bath, and laundry facilities for ultimate convenience. Outdoor living shines here with a front deck off the family room and multiple porch spaces. The quiet, dead-end street ensures peace and privacy. For just $100/year, the optional HOA provides deeded park access to beautiful Lake Maitland directly across the street—feel the refreshing lake breeze from your front door! Just minutes from the Winter Park Racquet Club and all that downtown Winter Park and Maitland have to offer. Zoned for award-winning Dommerich Elementary, Maitland Middle, and Winter Park High School. Complete with Terminix termite bond for peace of mind. This tranquil neighborhood retreat offers a rare combination of custom quality, natural beauty, and an unbeatable location. Don't miss this exceptional opportunity!
Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)
Listing Agent: Kelly Price (407-645-4321)
2150 TORTOISE SHELL DR, MAITLAND, FL 32751
$429,9006 Days on yellowkey MLS ID: O6392895
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1512 Built: 1997Monthly Fee: $17 Tax: $5,334 (2025)Community: WinfieldSingle Family
Taxes:$5,334
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained home in the heart of Maitland, offering the perfect blend of comfort, functionality, and Florida lifestyle living. This thoughtfully designed residence features a bright and open layout with spacious living areas, soaring ceilings, and an abundance of natural light throughout. The kitchen serves as the heart of the home, complete with ample cabinetry, generous counter space, and a convenient breakfast bar that opens seamlessly to the main living and dining areas, ideal for both everyday living and entertaining. Sliding glass doors lead to a private backyard with a paver patio, creating the perfect space to relax or host gatherings. The primary suite offers a peaceful retreat with plenty of space, natural light, and an en-suite bathroom for added convenience. Additional bedrooms are well-sized and versatile, perfect for guests, a home office, or growing households. Situated on a quiet street, this home features a fully fenced yard, mature landscaping, and a two-car garage. Conveniently located near shopping, dining, major roadways, and top-rated schools, this property combines tranquility with accessibility. Don’t miss the opportunity to make this move-in ready Maitland gem your own, schedule your private showing today.
Listing Agent: Claire Sims Llc (203-767-8109)
1610 LYNDALE BLVD, MAITLAND, FL 32751
$1,021,00041 Days on yellowkey MLS ID: G5109784
REDUCED by $54,000 (5.0%) on 04/24/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2598 Built: 2006 Tax: $17,444 (2025)Community: Dixie TerraceSingle Family
Taxes:$17,444
Remarks: PRICE REDUCTION, Incredible price for this property! LOCATION, LOCATION, LOCATION! Ideally situated just off Park Avenue in the highly desirable Maitland/Winter Park area, this beautifully maintained home offers the perfect blend of charm, functionality, and convenience. Featuring 4 bedrooms and 3.5 bathrooms, the home welcomes you with elegant formal living and dining spaces enhanced by detailed trim work, crown molding, and updated lighting. The spacious kitchen is designed for both everyday living and entertaining, showcasing a large quartz island and seamlessly overlooking the inviting family room, highlighted by a stunning fireplace. Step outside to a private backyard retreat complete with a spacious deck and covered patio—ideal for enjoying Florida’s outdoor lifestyle and hosting gatherings year-round. The primary suite, located on the second floor, offers a peaceful escape with its own private balcony—perfect for morning coffee or evening relaxation. The spa-like primary bathroom has been fully updated with a large walk-in shower, freestanding soaking tub, and modern finishes, along with an expansive walk-in closet featuring custom built-ins. Additional highlights include a freshly painted interior, a newer roof (2023), a fully fenced yard, large shed and beautifully landscaped grounds with irrigation and mature fruit trees. The extended driveway leads to a detached 2-car garage equipped with an electric vehicle charging station for modern convenience. Home is zoned for Winter Park Highs school and Dommerich Elementary. It is also conveniently located just minutes from Enzian Theater, Park Maitland School and the top shopping and dining destinations Winter Park has to offer, this move-in ready home delivers exceptional living in one of Central Florida’s most sought-after locations.
Listing is courtesy of: CAPITAL EQUITY REAL ESTATE CO (321-300-4211)
Listing Agent: Christian Del Pino (407-925-9389)
2130 DELORAINE TRL, MAITLAND, FL 32751
$829,00022 Days on yellowkey MLS ID: O6397018
REDUCED by $21,000 (2.5%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2175 Built: 1964 Tax: $10,394 (2025)Community: Highland Park Estates First AddSpa: NoSingle Family
Taxes:$10,394
Remarks: Welcome to this beautifully renovated pool home in the highly sought-after Dommerich neighborhood of Maitland. Offering over 2,000 square feet of living space, this 3-bedroom, 2-bath residence perfectly blends modern upgrades with comfortable, functional living. Inside the home is designed for both everyday living and entertaining. The spacious living room serves as the heart of the home, featuring a stunning marble fireplace and seamless flow into multiple gathering areas, including a dedicated dining space just off the kitchen, a family room that leads to the outside and access to the bedrooms. The fully renovated chef’s kitchen is a true standout, showcasing soft-gray shaker cabinetry, quartz countertops, a Carrera marble backsplash, and stainless steel appliances. With ample counter space and a built-in water filtration system, this kitchen is as functional as it is beautiful. Throughout the home, you’ll find upgraded Italian wood-plank porcelain tile flooring, offering both durability and elegance. The primary suite provides a peaceful retreat with a walk-in closet and a fully updated ensuite bathroom featuring a double-sink vanity, granite countertops, and a spacious walk-in shower with marble and porcelain finishes. Step outside into your private backyard oasis. Designed for true Florida living, this space features a Pebble Tec pool, paver deck, covered gazebo with ceiling fan, a 65” outdoor TV, and a premium sound system perfect for entertaining or relaxing year-round. The lush landscaping, grassy area, and additional storage shed complete the outdoor experience. Additional highlights include a new roof (2019), A/C system (2021), WiFi-enabled irrigation system, fresh interior paint, and new LG washer, dryer, and dishwasher. Located in the desirable Dommerich area, just minutes from top-rated schools, dining, shopping, and major roadways, this home offers the perfect combination of location, upgrades, and lifestyle. This is the one you’ve been waiting for.
Listing Agent: Mario Zendeli (407-325-3893)
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