Location: Maitland
Do Not Show Listings
612 GREEN MEADOW AVE, MAITLAND, FL 32751
$490,00041 Days on yellowkey MLS ID: O6401412
5 Days Off yellowkey (back on 5/27/2026)
REDUCED by $10,000 (2.0%) on 05/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1707 Built: 1970 Tax: $5,400 (2024)Community: Forest Brook 3Rd SecSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,400
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2024
Middle School: South Seminole Middle
Remarks: Under contract-accepting backup offers. Welcome to a home that doesn’t just check boxes — it supports your lifestyle. Tucked into one of Maitland’s beloved neighborhoods, Forest Brook, this delightful property blends comfort, practicality, and a little everyday serenity. *Lots of new since 2023: Whole house generator, 20’x12’ shed, front and back sod (just completed 4/2026), renovated driveway, gutters, vinyl fence in backyard & so much more!!* Home oozes charm showcasing a sunny yellow exterior with shutter details, white columns on covered front porch, fresh Florida style landscaping, finished concrete driveway, all leading you to covered front entry with pretty leaded glass front door. Step inside to tiled foyer entry and you’ll find a split floor plan offering privacy, flow, and room to spread out — whether you’re hosting, working from home, or simply enjoying a quiet morning. Separate formal dining room complete with sparkling chandelier and French door to patio has yard views. Generous living room has wood floors, new ceiling fan and wall of windows with double French doors to patio plus Plantation shutters. Inviting kitchen is a true gathering spot with a large island with seating on both sides, not to mention all the counter space, white cabinetry, complete stainless steel appliance package and new window above sink. Dedicated office/bonus space has ceiling fan and French door to patio with Plantation shutters. Spacious primary suite flaunts Plantation shutters, new ceiling fan, a walk-in closet plus an en-suite bath with adult height dual vanities, private commode and tiled shower stall. Two guest bedrooms on the other side of the home share updated bath with stylish modern vanity, dual sinks, decorative framed mirrors, chic light and a tub/shower combo. Unwind out back on the oversized covered and screened patio with dual ceiling fans offering lots of gathering space. Every room on the backside of the home contains a French door making it the perfect opportunity for that indoor-outdoor feel. Oversized backyard is fully fenced, freshly sodded and creates the perfect lush, green space ready for play, pets, gardening or gatherings. 20’x12’ shed is a dream for storage lovers or anyone who needs extra space – double doors, tons of room and endless possibilities. No power outages here! A whole house generator keeps life running smoothly no matter the weather. No scrambling, no stress — just uninterrupted comfort and security. Tree lined streets and quick access to parks, major connectors like 436, 414, N Orlando Avenue, Howell Branch Rd/Horatio, Red Bug Rd plus the YMCA, Advent Health and endless dining and shopping options like the Maitland City Center, Downtown Winter Park and so much more— it’s the kind of place where life feels a little easier and a lot more enjoyable!
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Stacy Wayne (407-415-9484)
502 OAK LN, MAITLAND, FL 32751
$599,00063 Days on yellowkey MLS ID: O6394681
REDUCED by $30,000 (4.8%) on 05/01/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1966 Built: 1958 Tax: $5,118 (2025)Community: Oakland ShoresSingle Family
Taxes:$5,118
Elementary School: Lake Orienta Elementary
High School: Lyman High
Tax Year: 2025
Middle School: Millennium Middle
Remarks: Welcome to 502 Oak Lane in Maitland, a beautifully updated pool home that blends comfort, character, and peace of mind. This fully improved 3 bedroom, 3.5 bathroom home has been thoughtfully updated throughout, including the replacement of the cast iron plumbing, offering both charm and important system improvements. Inside, you will find a well designed layout with spacious living areas, updated finishes, and plenty of natural light. Each bedroom offers its own bathroom, creating privacy and flexibility for guests or family. The home has been meticulously maintained and improved, making it truly move in ready. Step outside to your private backyard oasis featuring a pool, perfect for relaxing afternoons or entertaining friends and family. Located on a quiet street in Maitland, this home offers a great combination of location, updates, and lifestyle. This is a rare opportunity to own a fully improved pool home in one of Maitland’s most desirable areas.
Listing is courtesy of: KRESSLER REAL ESTATE (407-864-2184)
Listing Agent: Andre Kressler (407-864-2184)
933 and 935 ROBINHOOD CT, MAITLAND, FL 32751
$599,900221 Days on yellowkey MLS ID: O6355207
REDUCED by $75,100 (11.1%) on 04/14/2026
Bed: 6 Bath: 0.0 Gar: 4 Liv Area Sq Ft: 2484 Built: 1979 Tax: $7,294 (2024)Community: OakwoodApartment
Taxes:$7,294
Elementary School: None
High School: None
Middle School: None
Remarks: HUGE PRICE DROP! Whole Duplex. 6/4 (3 bed 2 bath in each unit). The Duplex is located in a cul-de-sac on a large lot that backs up to walking trail. Oakmont neighborhood has access directly to Sunrail Maitland Station. No HOA. Unit 933 has a fireplace for those cold Florida winters. The backyard is fully fenced and has an above-the-ground pool and a fully functionable bar with electric and running water. Great Investment Opportunity! Reroofed in 2018. FREE 1-0 Temporary Buydown Rate (receive a 1% lower rate for 12 months) through the seller's preferred lender. Ask your agent for more info!! Offer expires June 30th.
Listing is courtesy of: KGV REALTY GROUP (407-474-0844)
Listing Agent: Olaf Stenger (407-325-4147)
104 TANGELO CT, MAITLAND, FL 32751
$675,0007 Days on yellowkey MLS ID: O6403054
0 Days Off yellowkey (back on 5/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1850 Built: 1956 Tax: $4,493 (2025)Community: Hollieanna ShoresSingle Family
Taxes:$4,493
Elementary School: Dommerich Elem
High School: Winter Park High
Middle School: Maitland Middle
Remarks: Welcome to this updated 3 bedroom, 2 bath, plus office home located in sought-after Hollieanna Shores.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Wendy Williams Crumit (321-356-8590)
2809 WAUMPI TRL, MAITLAND, FL 32751
$745,00047 Days on yellowkey MLS ID: O6399820
0 Days Off yellowkey (back on 5/4/2026)
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: Under contract-accepting backup offers. 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)
1001 VERSAILLES CT, MAITLAND, FL 32751
$998,00038 Days on yellowkey MLS ID: O6401795
REDUCED by $52,000 (5.0%) on 05/15/2026
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
Elementary School: Lake Sybelia Elem
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)
623 GREEN MEADOW AVE, MAITLAND, FL 32751
$525,000110 Days on yellowkey MLS ID: O6380203
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1909 Built: 1970 Tax: $2,070 (2024)Community: Forest Brook 3Rd SecSingle Family
Taxes:$2,070
Remarks: Welcome to this two-owner concrete block home offering the perfect blend of comfort, character, and Florida outdoor living — all with no HOA and an ideal Central Florida location. A majestic Kapok tree gracefully anchors the front yard, while a lush, foliaged trellis guides you to the inviting front entrance, setting the tone for the unique charm found throughout. Inside, you’ll discover an open floorplan designed for both everyday living and effortless entertaining. The kitchen is a true showstopper, featuring a gorgeous tongue-in-groove ceiling, stylish pendant lighting, and a chef-inspired gas range that will delight any home cook. The living spaces flow seamlessly, creating a bright and welcoming atmosphere. The generous primary bedroom offers a relaxing retreat, while three additional bedrooms and two full baths provide flexibility for family, guests, or a home office. An oversized double garage adds convenience and plenty of storage. Step outside to your private backyard oasis. A screened patio and rear yard pergola invite year-round outdoor enjoyment, while the terraced backyard leads down to a serene pondfront, inground pool — perfect for relaxing, entertaining, or simply taking in the peaceful water views. Ideally located just minutes from Full Sail University, along with Winter Park, Casselberry, Winter Springs, and Altamonte Springs, this home offers both tranquility and easy access to shopping, dining, and major commuter routes. This is Florida living at its finest — schedule your private showing today! ROOF/HVAC/Water Heater 2021
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: John Muccigrosso, Pa (407-234-6330)
1256 WELLINGTON TER, MAITLAND, FL 32751
$1,250,000102 Days on yellowkey MLS ID: O6383274
1 Days Off yellowkey (back on 5/26/2026)
REDUCED by $140,000 (10.1%) on 05/12/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4280 Built: 1987Monthly Fee: $48 Tax: $13,013 (2025)Community: WellingtonSpa: NoSingle Family
Taxes:$13,013
Remarks: Under contract-accepting backup offers. HARD TO FIND SKI LAKEFRONT! Classic traditional beauty – ready for a lucky buyer to make home. Stunning water & sunset views over Lake of the Woods from most living areas. Enter into the impressive foyer with curved stairway; light & bright large formal rooms with French doors to wrap around covered porch; Large open kitchen, wood cabinets, granite tops, stainless appliances and breakfast nook to sip coffee and bird watch! Inviting family room with fireplace and custom built in surrounds. First level guest suite and full bath; elevator serves to 2nd level huge Master suite, with open deck and lake views; Master bath, dual vanities, Jacuzzi tub and shower, walk in closet. 2 additional large sunny bedrooms share Jack & Jill bath, 3rd upstairs bedroom is ensuite with a large walk in closet. Lovely landscape provides privacy and beauty. New boathouse and dock are ready for action! Super side entry 3 car garage, storage, huge utility room. Survey, pool plan available. Seminole County Schools PLUS excellent Private Schools within a few miles. Neutral colors, tile roof. Bring your water skis, knee boards, fishing poles & kayaks! Sold As-is; seller may consider decor credit with acceptable offer!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Lisa Gould (407-721-7612)
109 KYLE DR, MAITLAND, FL 32751
$850,00011 Days on yellowkey MLS ID: O6410033
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1870 Built: 1973Monthly Fee: $13 Tax: $6,724 (2025)Community: Minnehaha ShoresSpa: NoSingle Family
Taxes:$6,724
Remarks: A tropical retreat in Minnehaha Shores with deeded lake access to the Winter Park Chain of Lakes. Tree-lined streets welcome you to this beautifully reimagined four-bedroom, two-bath split-plan home with coastal influences throughout. Formal living, dining and family spaces blend seamlessly together, creating great flexibility in layout. French doors line the back of the home and open to the covered lanai, offering effortless indoor-outdoor entertaining. This home offers an outdoor living experience that feels exceptional. Carefully curated with Florida native plants, tropical palms and ambient landscape lighting, the private backyard surrounds a beautiful pool, fountain feature, fire pit lounge and hot tub, a property that has it all. The kitchen features solid 42-inch cabinetry, stainless steel appliances, exotic granite countertops and counter seating. A beautiful porcelain sink overlooks the outdoor oasis, bringing the beauty of the outdoors inside. The primary suite is privately situated on one side of the home, while the remaining bedrooms are grouped together on the opposite side. The renovated primary bath showcases a spacious walk-in shower, designer finishes and ambient lighting. Additional improvements include a 2022 roof, updated plumbing and electrical panels, designer wallpaper throughout, engineered wood flooring in select spaces, recessed lighting, upgraded rear windows, a pool pump (2024), a repoured driveway with an additional parking pad and room for a boat or RV with 30 amp electrical, a wood-burning fireplace and much more. This neighborhood is special. Minnehaha Park sits at the entrance to the community and features tennis courts, new pickleball courts, a playground and expansive green space. Enjoy easy access to downtown Maitland and Maitland Social, which host many planned community events throughout the year. Maitland is home to renowned restaurants, The Enzian Independent Theater with Annual Film Festival and Lake Lily Park with weekly farmer’s market. Maitland offers a quintessential Florida lifestyle. Minnehaha Shores is a quiet neighborhood with no cut-through streets and enjoys access to a shared lakefront lot with a boat ramp and green space for entertaining or simply enjoying a Florida sunset. Zoned for highly regarded Orange County Public Schools, including Lake Sybelia Elementary School, Maitland Middle School and Winter Park High School, home to the globally recognized International Baccalaureate Program.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
105 TANGELO CT, MAITLAND, FL 32751
$1,798,999180 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)
1851 HURON TRL, MAITLAND, FL 32751
$949,90018 Days on yellowkey MLS ID: O6407236
0 Days Off yellowkey (back on 5/19/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2312 Built: 1959 Tax: $11,783 (2025)Community: Dommerich Estates 3Rd Add MaitlandSpa: YesSingle Family
Taxes:$11,783
Remarks: Under contract-accepting backup offers. Beautifully updated four-bedroom, 2.5-bath home in the heart of Dommerich Estates, one of Maitland’s loved neighborhoods known for its top-rated schools, tree-lined streets and access to the Winter Park Chain of Lakes. Just steps from the neighborhood lake lot and nearby Maitland Community Park, this home offers over 2,300 square feet with warm wood flooring, crisp light walls and thoughtful designer updates throughout. Formal living and dining spaces flow into an open kitchen and gathering area, with large sliding doors leading to the backyard for effortless indoor-outdoor entertaining. The kitchen features custom 42-inch cabinetry, quartz countertops, stainless steel appliances, peninsula seating and generous pantry and laundry space. The living room centers around a charming brick, wood-burning fireplace with expansive backyard views. Outside, enjoy a screened porch, a PebbleTec pool, a paver deck and additional green space perfect for relaxing or entertaining. The spacious primary suite includes double vanities, a walk-in shower and ample closet space. Major updates include a roof (2022), Trane XV19 variable-speed HVAC (2024), updated kitchen finishes (2022), a Pentair pool heater, a new pool pump, a Jandy iAquaLink automation system, recessed lighting, a Google Nest doorbell and Lutron Caseta smart home controls. Enjoy close proximity to Dommerich Elementary and Maitland Middle, zoned for Winter Park High, plus easy access to parks, Lake Lily, the Enzian Theater, restaurants and more.
24 MINNEHAHA CIR, MAITLAND, FL 32751
$849,90018 Days on yellowkey MLS ID: O6407597
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2669 Built: 1957Monthly Fee: $13 Tax: $674,620 (2025)Community: Minnehaha ShoresSpa: NoSingle Family
Taxes:$674,620
Remarks: Move-in ready 5-bedroom pool home in sought-after Minnehaha Shores with private lake access to Lake Minnehaha and the Winter Park Chain of Lakes. This beautifully updated Maitland home features a NEW Roof (2022), all NEW flooring throughout, beautiful plantation shutters, updated modern fixtures, updated electrical panel & wiring, and plumbing already completed for added peace of mind. Located within one of Maitland’s most desirable residential communities, Minnehaha Shores is comprised of only 42 homes and offers residents private lake access and community dock, park, playground and tennis courts. Inside, the flexible 5-bedroom layout includes TWO primary suites and a desirable 3-way split floor plan that provides exceptional privacy and versatility for multigenerational living, guests, or work-from-home needs. The spacious living room welcomes you with a beautiful stacked-stone fireplace, while the formal dining room connects naturally to the kitchen and family room, creating an ideal flow for both everyday living and entertaining. The remodeled kitchen features shaker-style cabinetry, granite countertops, stainless steel appliances, oversized pantry , and an adjoining breakfast area with additional storage options and built-in desk. Multiple living spaces, spacious laundry room, great natural light, and thoughtful design details throughout make the home feel both comfortable and functional. The main primary suite is positioned privately toward the back of the home and includes an attached flex space perfect for an office, nursery, sitting room, or workout area. A secondary primary suite is located off the main living area that creates an ideal guest or in-law setup. Outside, enjoy Florida living year-round with a screen-enclosed pool & patio, and easy-maintenance landscaping that enhance the home’s overall privacy and curb appeal. Additional upgrades include dual-pane energy-efficient windows and French doors, fiberglass exterior doors, modern lighting, gorgeous large porcelain tile & ceramic wood-look tile throughout, decorative baseboards & trim, plantation shutters, and extensive storage throughout. If you’ve been searching for an updated Maitland pool home that offers private access to the Winter Park Chain of Lakes, a flexible living space, modern upgrades, and a prime location close to the area's top dining, shopping, and entertainment... this home offers a rare combination of lifestyle, functionality, and convenience.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Allison Day (407-617-2881)
2453 WORTHINGTON RD, MAITLAND, FL 32751
$585,000178 Days on yellowkey MLS ID: TB8454086
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1959 Built: 1966 Tax: $1,675 (2024)Community: English Estates Unit 3Spa: NoSingle Family
Taxes:$1,675
Remarks: A lovely well designed 4bdr. 2 bath home with an eat in kitchen open to a spacious family rm. A formal din.rm. and formal lvg.rm. are ready for any occasion. The long 2 lane brick driveway can accommodate multiple vehicles. Nearby schools for all levels and the amenities for recreation and entertainment are too numerous to list. This house should be added to your list when searching for your new home.
Listing is courtesy of: REALTY OF RIVERVIEW LLC (813-863-3948)
Listing Agent: Stephen Hachey (813-863-3948)
2150 TORTOISE SHELL DR, MAITLAND, FL 32751
$429,90040 Days on yellowkey MLS ID: O6392895
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1512 Built: 1997Monthly Fee: $17 Tax: $5,334 (2025)Community: WinfieldSingle Family
Taxes:$5,334
High School: Edgewater High
Middle School: Lockhart Middle
Remarks: One or more photo(s) has been virtually staged. FRESHLY UPDATED CABINETRY, FOURTH BEDROOM OPTION ADDED! Welcome to this beautifully maintained home in the heart of Maitland, offering the perfect blend of comfort, functionality, and Florida lifestyle living. This thoughtfully designed residence features a bright and open layout with spacious living areas, soaring ceilings, and an abundance of natural light throughout. The kitchen serves as the heart of the home, complete with ample cabinetry, generous counter space, and a convenient breakfast bar that opens seamlessly to the main living and dining areas, ideal for both everyday living and entertaining. Sliding glass doors lead to a private backyard with a paver patio, creating the perfect space to relax or host gatherings. The primary suite offers a peaceful retreat with plenty of space, natural light, and an en-suite bathroom for added convenience. Additional bedrooms are well-sized and versatile, perfect for guests, a home office, or growing households. Situated on a quiet street, this home features a fully fenced yard, mature landscaping, and a two-car garage. Conveniently located near shopping, dining, major roadways, and top-rated schools, this property combines tranquility with accessibility. Don’t miss the opportunity to make this move-in ready Maitland gem your own, schedule your private showing today.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Claire Sims Llc (203-767-8109)
1511 GLASTONBERRY RD, MAITLAND, FL 32751
$565,00028 Days on yellowkey MLS ID: O6404282
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2376 Built: 1969 Tax: $1,959 (2024)Community: NorthgateSingle Family
Taxes:$1,959
Remarks: This AMAZING!, spacious 5-bedroom, 3-bath split-level home is located in a fantastic neighborhood and is packed with standout features. Upstairs, you’ll find beautiful engineered hardwood flooring throughout the main living areas, with carpet in the bedrooms and tile in the baths. A stunning screened-in porch overlooks the backyard and pool, offering a perfect spot to relax or entertain. The bright and airy formal living room provides plenty of space, while the dining room includes sliding doors that lead out to the porch. The large eat-in kitchen offers ample cabinet storage and even features a convenient pass-through window to the porch/outside bar—ideal for hosting. The upper level includes three bedrooms two bathrooms. Just a few steps down, the lower level opens to a massive family room with tile floors set to entertain family and friends with two additional bedrooms with carpet and a full bath. Tile flooring runs throughout this level. Additional highlights include outdoor spa , updated windows, a re-piped plumbing system, updated Electrical, and a well-maintained interior full of character. The home comes with paid in full solar panels and a Terminix termite bond and Well Maintained sprinkler system on well. Washer/Dryer are located in the garage. The garage include cabinets for additional storage. The yard features mature Citrus trees and Magnolia trees adding to the home’s charm. With its flexible layout, inviting screened porch, and beautiful salt water pool area, this home truly has it all.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Maydelin Munoz (407-485-4990)
2837 SHADOW VIEW CIR #2837, MAITLAND, FL 32751
$225,000104 Days on yellowkey MLS ID: O6382993
3 Days Off yellowkey (back on 5/16/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1280 Built: 2000 Tax: $3,600 (2025)Community: Visconti EastCondo
Taxes:$3,600
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. LIMITED TIME ONLY THROUGH MAY 11! Seller is offering a $5,000 contribution towards buyer’s closing costs. Move-In Ready Maitland Condo with Rare 2-Car Garage & Flexible Work-From-Home Layout Welcome to this beautifully updated three-level condo in a gated Maitland community—offering the space, flexibility, and low-maintenance lifestyle today’s buyers are looking for. This 2-bedroom, 2-bath home features a versatile office/flex room, ideal for working from home, a guest space, gym, or creative studio. Soaring ceilings, abundant natural light, and a smart multi-level layout create a bright and open feel throughout. Recent 2026 upgrades include fresh interior paint, brand-new carpet, updated bathrooms, new window blinds, and stainless steel appliances (refrigerator 2024), along with a full-size in-unit washer and dryer—making this home truly move-in ready. One of the standout features is the rare 2-car garage—hard to find in this area—offering added convenience and storage. Enjoy a low-maintenance lifestyle with HOA coverage that includes exterior maintenance, landscaping, valet trash, water, sewer, and pest control. The community offers resort-style amenities including two pools, fitness center, clubhouse, tennis and basketball courts, and playground. Ideally located just minutes from I-4, shopping, dining, and daily conveniences, this home offers both comfort and connectivity. Home includes a warranty and is available for immediate occupancy.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Nilufer Rohleder (407-962-7494)
1140 S ORLANDO AVE #E2, MAITLAND, FL 32751
$235,00017 Days on yellowkey MLS ID: O6404875
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 612 Built: 1971 Tax: $539 (2025)Community: Lake Maitland Terrace AptsCondo
Taxes:$539
Remarks: Live the lake lifestyle in this beautifully updated 1-bedroom condo located in the iconic mid-century modern community of Lake Maitland Terrace. Completely refreshed in 2025, this first-floor residence features a brand-new HVAC system, new appliances including washer, dryer, and kitchen disposal, updated kitchen countertops, and new flooring throughout the living areas. Freshly painted and thoughtfully enhanced, the home blends timeless mid-century character with modern comfort and style. The spacious bedroom showcases sleek modern concrete flooring, adding to the authentic architectural aesthetic and contemporary feel. Perfectly positioned within a charming two-story mid-rise building, this residence offers effortless access to the community’s exceptional waterfront amenities and relaxed lakefront atmosphere. Set on Lake Maitland—the largest lake on the Winter Park Chain of Lakes—residents enjoy direct lake access for boating, kayaking, canoeing, fishing, and water-skiing. A private community dock is located on-site, while the City of Maitland public boat ramp sits conveniently next door. Boat slips may also be available upon request. The location is truly unbeatable. Just one block from Lake Lily and Fort Maitland Park, and only minutes from Park Avenue, residents can walk to the Maitland Farmers Market, local restaurants, coffee shops, gym, dry cleaning, barber shop, boba tea, and more—all directly across the street. Enjoy easy biking access to Park Avenue for premier shopping, dining, and entertainment. Residents of Lake Maitland Terrace enjoy outstanding amenities including a newer community pool, lakefront clubhouse with breathtaking views available for private events, on-site laundry facilities, free unlimited water, and twice-weekly valet trash service. Experience maintenance-free living where iconic mid-century modern design meets modern updates and an unmatched Central Florida lakefront lifestyle.
Listing is courtesy of: METRO CITY REALTY (407-237-3331)
Listing Agent: Beatrice Miranda (407-592-4448)
2040 BOBTAIL DR, MAITLAND, FL 32751
$370,00014 Days on yellowkey MLS ID: O6408698
0 Days Off yellowkey (back on 5/22/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1382 Built: 1998Monthly Fee: $18 Tax: $3,097 (2025)Community: Winfield Ut 1Single Family
Taxes:$3,097
Remarks: Cute home alert! Finally — an updated, move-in ready home in an amazing Maitland location priced under $400K! Imagine hosting friends and family in the spacious separate dining room, gathering around the oversized kitchen island while dinner cooks, and spending evenings relaxing on the screened patio and playing safely in the fully fenced backyard. Tucked inside the quiet Winfield community with a low HOA, this beautifully maintained 3-bedroom, 2-bath home with split floor plan is an excellent balance of modern style and everyday functionality. Step inside to discover a bright, open-concept layout featuring vaulted ceilings, recessed lighting, and consistent hard-surface flooring throughout. The spacious living area flows seamlessly into the fully updated gourmet kitchen, complete with beautiful countertops, 42” solid wood soft-close cabinetry, and high-end stainless steel appliances — creating a welcoming space in the heart of your home. This split floor plan offers both privacy and flexibility, with an expansive primary suite featuring a walk-in closet with custom built-ins and a beautifully updated bathroom with dual vanities, a relaxing garden tub, and separate shower. On the opposite side of the home, two additional bedrooms are ideal for a nursery, guest room, playroom, or home office. The living space flows to a covered and screened patio, creating a perfect space for year-round indoor-outdoor living. Whether you’re enjoying slow mornings with coffee, hosting weekend get-togethers, or relaxing after work, the fully fenced backyard offers both comfort and privacy. Fresh landscaping, mature shade trees, and the perfect mix of filtered sunlight and greenery give the outdoor space a calm, inviting feel, while the tiled flooring adds a clean, polished touch that’s both stylish and low maintenance. ROOF: 2018
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: Michael Wathen (407-205-7660)
2134 KORAT LN, MAITLAND, FL 32751
$364,50016 Days on yellowkey MLS ID: O6401286
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1642 Built: 1998Monthly Fee: $18 Tax: $5,340 (2025)Community: WinfieldSingle Family
Taxes:$5,340
Remarks: All highest and best offers due by 10:00 AM EST on 5/21/26. Welcome home! This inviting three-bedroom, two-bathroom residence in the heart of Maitland combines everyday convenience with a comfortable living environment ready for years of memories. As you step inside, vaulted ceilings draw the eye upward, creating a sense of openness throughout the interior, while its functional design delivers multiple living areas, a spacious primary suite, and flexible secondary bedrooms, perfect for life’s ever-changing needs. The thoughtful floor plan boasts a natural flow between living areas, bedrooms, and the screened patio, creating a residence that feels both spacious and intimate; ideal for day-to-day life and entertaining guests. The new HVAC System, new Water Heater, and fresh exterior paint add to the list of positives, allowing for peace of mind for years to come. Beyond the interior, a partially covered screened lanai extends the living space, offering a sheltered retreat, with a fenced backyard to maximize privacy. Location-wise, this property places you in the heart of the action near vibrant shopping, dining, and entertainment options. Within one mile, you will find multiple restaurants, shopping plazas, and the Orlando Sportsplex/Ice Den, providing everyday needs at your doorstep. For days when you want to venture further, you are less than five miles from the Winter Park Village, Altamonte Mall, College Park, medical services, multiple golf courses and sports fields, various parks and nature trails, and immediate highway access, which allows for a straightforward journey to anywhere in Central Florida and beyond. Schedule your private showing today and experience the convenience of this move-in-ready property firsthand.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY (407-203-0007)
Listing Agent: Joseph Doher (407-203-0007)
1321 BENEVOLENT ST, MAITLAND, FL 32751
$369,000112 Days on yellowkey MLS ID: O6377413
3 Days Off yellowkey (back on 5/21/2026)
REDUCED by $5,900 (1.6%) on 05/02/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1751 Built: 2006Monthly Fee: $520 Tax: $2,204 (2024)Community: Enclave/Maitland A-FTownhouse
Taxes:$2,204
Remarks: Under contract-accepting backup offers. BELOW APPRAISAL + SELLER OFFERING INTEREST RATE BUY-DOWN with acceptable offer. /// Why settle for "standard" when you can own a designer-caliber home in Maitland with a lower monthly payment? Priced at $369,000—well below the recent $384K appraisal—this high-end unit offers instant equity. *LIFESTYLE & LOCATION /// RECLAIM YOUR TIME: Just 10 minutes to Downtown Orlando or Winter Park. PET FRIENDLY: Montecino is a gated, pet-loving community. LAKE CHARITY: Enjoy a scenic walk right outside your door. Maintenance-free living with a resort-style pool and gated security. *UPGRADES & VALUE /// MECHANICALLY NEW: New HVAC (Jan 2025), Bosch dishwasher, and 2026 fridge/microwave. DESIGNER FINISHES: Engineered hardwoods, fresh paint, and designer lighting. HOA BONUS: Monthly dues include High-Speed Internet, WiFi, and expanded TV/Streaming.*PEACE OF MIND /// Home just passed INSPECTION. Between the verified value, mechanical updates, and potential interest rate buy-down, this is the most secure and affordable luxury entry in Maitland. Also available for rent at $2500/month. Seller seeking a long-term, high-quality tenant.
Listing Agent: Shirley Jones (407-719-9180)
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