Displaying: For Sale
Location: Maitland
Property Type(s): Single Family
Price: $400,000 to $499,000
Do Not Show Listings
Maitland - 6 properties found
775 WOODSIDE RD, MAITLAND, FL 32751
$449,0003 Days on yellowkey MLS ID: O6403039
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1456 Built: 1973 Tax: $3,458 (2025)Community: Forest Brook 5Th SecSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,458
Elementary School: English Estates Elementary
High School: Lake Howell High
Tax Year: 2025
Middle School: South Seminole Middle
Remarks: Welcome to 775 Woodside Road, ideally situated on a quiet cul-de-sac just minutes from Maitland and Winter Park’s most popular destinations. This beautifully updated three-bedroom, two-bath home offers an open floor plan filled with inviting living spaces and abundant natural light. Luxury vinyl flooring was installed throughout the home in 2023, while plantation shutters in the living room and bedrooms add both style and privacy. Sliding glass doors from the dining area and primary bedroom open to the spacious backyard, offering plenty of green space and room for a future pool. The kitchen is both functional and welcoming, featuring soft-close cabinetry, quartz countertops, stainless steel appliances, a designer backsplash, farmhouse sink, and a breakfast bar perfect for casual dining or entertaining. All three bedrooms offer generous closet space, complemented by two additional hallway linen closets. The spacious primary suite includes a walk-in closet and an updated bath with a large glass-enclosed shower and dual-sink vanity. The guest bath features a shower/tub combination and an updated vanity. Recent improvements provide peace of mind and include a newer water heater (2019), HVAC system (2020), roof (2021), and a partial re-pipe to reroute the main sewer line (2021).
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Wendy Williams Crumit (321-356-8590)
220 ALPINE DR, MAITLAND, FL 32751
$450,00060 Days on yellowkey MLS ID: O6388051
0 Days Off yellowkey (back on 5/2/2026)
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
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same family since the 1960s, is ideally located near shopping, dining, parks, and major roadways, providing convenient access throughout Central Florida. The property offers potential for renovation, expansion, or redevelopment, with a lot that provides space for future improvements. Ideal for homeowners, builders, or investors seeking a property in a desirable and established area. The adjacent property to the west (210 Alpine) is also available for purchase. Contact the listing agent for additional information and pricing on the neighboring parcel.
Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)
Listing Agent: Beth Hathaway (407-314-1300)
2150 TORTOISE SHELL DR, MAITLAND, FL 32751
$429,90011 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
Elementary School: Lake Sybelia Elem
High School: Edgewater High
Middle School: Lockhart Middle
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 is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Claire Sims Llc (203-767-8109)
2065 DERBYSHIRE RD, MAITLAND, FL 32751
$449,990122 Days on yellowkey MLS ID: S5140785
1 Days Off yellowkey (back on 5/1/2026)
REDUCED by $40,000 (8.2%) on 04/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1430 Built: 1959 Tax: $1,582 (2024)Community: English Estates Unit 1Single Family
Taxes:$1,582
Remarks: Under contract-accepting backup offers. Beautifully renovated and move-in ready, this 3-bedroom, 2-bath home offers modern design in a .24 acre lots, solid upgrades, and comfortable living in a prime Maitland location. Featuring an open-concept layout filled with abundant natural light, the home delivers a warm and inviting atmosphere from the moment you enter. The updated kitchen serves as the heart of the home, showcasing sleek cabinetry, a spacious island, and a full suite of stainless steel appliances, including refrigerator, stove, microwave, dishwasher, washer, dryer, and range hood—ideal for both everyday living and entertaining. Contemporary flooring flows seamlessly throughout, enhancing the home’s clean and modern aesthetic. Major systems have been thoughtfully updated, providing peace of mind to the next owner: roof replaced in 2021, A/C updated in 2019, and water heater installed in 2020. The home features copper electrical wiring and durable plumbing with cross-linked polyethylene inside walls and PVC piping beneath, reflecting quality construction and modernization. Spacious living areas delivers comfort and functionality, while the backyard provides a versatile outdoor space ready for relaxation, entertaining, or personalization. The property includes a 2-car garage and is located in a community with NO HOA and NO CDD, offering flexibility and lower ownership costs. Conveniently situated near major roads, shopping, dining, and everyday amenities, this home presents an excellent opportunity for buyers seeking style, reliability, and location in one complete package.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Ceila Morales (888-883-8509)
1231 SIDCUP RD, MAITLAND, FL 32751
$495,000271 Days on yellowkey MLS ID: TB8414987
2 Days Off yellowkey (back on 3/13/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1798 Built: 1960 Tax: $1,683 (2024)Community: English Estates Unit 1Spa: NoSingle Family
Taxes:$1,683
Remarks: Under contract-accepting backup offers. Prepare to be captivated by this fully renovated gem located in the highly sought after English Estates neighborhood. Offering 1,798 square feet of meticulously designed living space, this three bedroom, two bathroom home blends timeless charm with modern luxury. Every inch has been thoughtfully updated, including a brand new air conditioning system, new thermostat, and a newer roof. The home features an open layout with custom details such as designer sconces, a fluted accent wall, and an abundance of natural light throughout. The spacious primary suite includes a spa inspired bathroom designed to feel like a private retreat. Step outside to a fully fenced backyard oasis complete with a sparkling pool and outdoor shower, perfect for entertaining or relaxing in total privacy. Located in a no flood zone, this property offers peace of mind and lifestyle convenience. Just minutes from I-4, the Altamonte Mall, and a short walk or bike ride to the scenic Kawannee Trail, this location provides easy access to everything Orlando has to offer. This is a rare opportunity to own a stunning home in a well established neighborhood. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)
Listing Agent: Andrea Heck (813-777-7219)
1291 OXFORD RD, MAITLAND, FL 32751
$469,900 MLS ID: O6387809
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1370 Built: 1961Community: English Estates Unit 2Single Family
Taxes:
Tax Year:
Remarks: Welcome to this thoughtfully updated one-story home in the established community of English Estates, where timeless design and everyday comfort come together. A brick paver driveway leads to the front porch creating an inviting first impression. Inside, the light-filled living room opens effortlessly into the heart of the home. The updated kitchen features granite countertops, beautiful 42-inch cabinets, stainless steel appliances, and a convenient breakfast bar perfectly positioned to flow into the dining area. A separate family room offers additional living space and opens to a covered, screened porch which is an ideal setting for relaxed evenings or casual outdoor dining. Back inside, two secondary bedrooms share a beautifully updated full bath, while the primary bedroom offers a peaceful retreat complete with its own private en suite bathroom. Step outside to a spacious, fenced backyard with plenty of room for entertaining, gardening, or simply enjoying the Florida sunshine. Recent improvements that add both value and peace of mind, include a new roof (2024) with transferable five-year warranty, A/C (2021), whole house replumbed (2021), irrigation system (2022), septic drain field (2018) and updated double paned windows. You will love how close you will be to to Winter Park with their great farmers markets, Park Ave and so much more! Conveniently located with easy access to major roadways, shopping, and restaurants, this move in ready home offers a wonderful blend of comfort, updates, and location. A home that is easy to enjoy and well worth seeing in person. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Barrett Spray (407-927-3650)
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