Maitland, FL Homes

/40
$174,900
- 2 Beds
- 1 Bath
- 898 Sq Ft
1375 Lake Shadow Cir Unit 11203, Maitland, FL 32751

Amazing upgraded two-bedroom, one bath Condo in the gated waterfront community at Visconti in Maitland with features of spacious living and comfortability. This stunning Condo Unit features with large windows letting in plenty of natural light and giving the common living area a fresh air feel. The dining/living combo opens to a big, screened patio through sliding glass doors. The kitchen

Simon Colak USCO CAPITAL GROUP

1375 Lake Shadow Cir Unit 11203, Maitland, FL 32751
/8
$1,235 Per Month
- 1 Bed
- 1 Bath
- Condo for Rent
118 Eaton St Unit 4, Eatonville, FL 32751

O/LB 1 Bedroom, 1 Bath, Living Room, Eat In Kitchen, Quad-Plex! Apply Today! If you would like to view this property, and TO SCHEDULE A SHOWING PLEASE EMAIL US AT FOR AVAILABLE SHOW TIMES. Please send us your Name, Phone Contact and Email Address. All Showings are done Monday thru Friday between 10am & 4pm.HOW TO APPLY/ABOUT OUR APPLICATION PROCESS: Our application process has

118 Eaton St Unit 4, Eatonville, FL 32751
/2
$507,200 Sold Dec 04, 2025

1550 Ridgewood Ave, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,760 Sq Ft
- Built 1989
Last Sold Summary
- 2% Below List Price
- $288/SF
- 46 Days On Market
Current Estimated Value $543,746

Last Listing Agent Justin Pekarek ORLANDO PROPERTY ADVISORS

1550 Ridgewood Ave, Maitland, FL 32751

/2
Est $218,977 Not Listed For Sale

1501 Grove St Unit 560, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,087 Sq Ft
- Built 1979
1501 Grove St Unit 560, Maitland, FL 32751

Last Sold Summary
- 4% Below List Price
- $211/SF
- 57 Days On Market
- Last Sold Price $229,000
- Aug 22, 2024
Last Listing Agent Rebecca Hopson CHARLES RUTENBERG REALTY ORLANDO

/29
$449,000 Pending
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
775 Woodside Rd, Maitland, FL 32751

Under contract-accepting backup offers. 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

Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

775 Woodside Rd, Maitland, FL 32751
/32
$1,695 Per Month
- 2 Beds
- 1 Bath
- 770 Sq Ft
- Townhouse for Rent
190 Ventris Ave W, Maitland, FL 32751

One or more photo(s) has been virtually staged. This beautiful home is a completely renovated and updated 2-bedroom, 1-bath duplex in Maitland, FL, offering modern finishes throughout! Enjoy a large backyard, private parking and an exterior laundry room for added convenience. This home has spacious and bright bedrooms and a beautifully updated kitchen! Freshly painted, brand-new flooring and a

Linda Baez DON ASHER & ASSOCIATES, INC.

190 Ventris Ave W, Maitland, FL 32751
/2
$579,000 Sold Oct 10, 2025

1434 Winston Rd, Maitland, FL 32751
- 4 Beds
- 2 Baths
- 2,312 Sq Ft
- Built 1971
Last Sold Summary
- $250/SF
- 16 Days On Market
Current Estimated Value $567,266

Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

1434 Winston Rd, Maitland, FL 32751

/2
Est $216,074 Not Listed For Sale

1225 Lake Shadow Cir Unit 14202, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,111 Sq Ft
- Built 2000
1225 Lake Shadow Cir Unit 14202, Maitland, FL 32751

Last Sold Summary
- 8% Below List Price
- $212/SF
- 55 Days On Market
- Last Sold Price $235,000
- Aug 13, 2024
Last Listing Agent Kati Ettinger INNOVATIVE REALTY, LLC

/52
$1,390,000
- 5 Beds
- 4.5 Baths
- 4,280 Sq Ft
1256 Wellington Terrace, Maitland, FL 32751

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

Lisa Gould KELLER WILLIAMS WINTER PARK

1256 Wellington Terrace, Maitland, FL 32751
/23
$2,450 Per Month
- 3 Beds
- 2 Baths
- 1,496 Sq Ft
- House for Rent
520 Seneca Trail, Maitland, FL 32751

Spacious Maitland Rental Home located in the Community of Dommerich Estates. Conveniently located Minutes from Dommerich Elementary School, Howell Branch Park, Lake Minnehaha, Downtown Winter Park, and Downtown Orlando. Home offers Newly Renovated Kitchen & Bathroom , 3 Bedroom, 2 Bath home features a 2 Car Carport, Ceiling Fans, Terrazzo Floors throughout, Laundry Room, Fenced Back Yard, and

520 Seneca Trail, Maitland, FL 32751
/2
$255,000 Sold Dec 08, 2025

240 Cherrywood Dr, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,161 Sq Ft
- Built 1959
Last Sold Summary
- 9% Below List Price
- $220/SF
- 6 Days On Market
Current Estimated Value $260,825

Last Listing Agent Martha Grasty EXP REALTY LLC

240 Cherrywood Dr, Maitland, FL 32751

/40
Est $319,333 Not Listed For Sale

1010 Winderley Place Unit 131, Maitland, FL 32751
- 3 Beds
- 2.5 Baths
- 1,563 Sq Ft
- Built 1997
1010 Winderley Place Unit 131, Maitland, FL 32751

Last Sold Summary
- 10% Below List Price
- $227/SF
- 17 Days On Market
- Last Sold Price $355,000
- Jun 11, 2024
Last Listing Agent Jean Chalifour COLDWELL BANKER REALTY

/18
$349,000 Pre-Foreclosure
- 3 Beds
- 2 Baths
- 1,407 Sq Ft
361 Hickory Dr, Maitland, FL 32751

Under contract-accepting backup offers. 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

Emma Nelson KELLER WILLIAMS REALTY AT THE PARKS

361 Hickory Dr, Maitland, FL 32751
/17
$1,650 Per Month
- 2 Beds
- 1 Bath
- 1,100 Sq Ft
- House for Rent
301 Clark St Unit 2, Maitland, FL 32751

Cozy and private 2-bedrooms, 1-bath rental located in Maitland. This comfortable unit features a living area and a functional kitchen equipped with a stove and microwave, ideal for convenient everyday living.Rent includes water, electricity, and internet, offering a simple and hassle-free living experience. Conveniently located with easy access to shopping, dining, and major roadways, this

Laury Cruz Penalo De Gomez MY REALTY GROUP, LLC.

301 Clark St Unit 2, Maitland, FL 32751
/2
$330,000 Sold Dec 30, 2025

735 Gamewell Ave, Maitland, FL 32751
- 2 Beds
- 1 Bath
- 938 Sq Ft
- Built 1952
Last Sold Summary
- $352/SF
- 2 Days On Market
Current Estimated Value $327,739

Last Listing Agent Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

735 Gamewell Ave, Maitland, FL 32751

/22
Est $188,438 Not Listed For Sale

216 Cherrywood Gardens Dr Unit 216, Maitland, FL 32751
- 2 Beds
- 1.5 Baths
- 953 Sq Ft
- Built 1974
216 Cherrywood Gardens Dr Unit 216, Maitland, FL 32751

Last Sold Summary
- 16% Below List Price
- $236/SF
- 3 Days On Market
- Last Sold Price $225,000
- Apr 19, 2024
Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

/38
$1,240,000
- 4 Beds
- 4 Baths
- 4,149 Sq Ft
51 Oakleigh Ln, Maitland, FL 32751

Come see 51 Oakleigh Ln, a functional residence arranged for everyday practicality. A comfortable living space features a fireplace. The kitchen includes an accent backsplash and all stainless steel appliances. The primary bedroom has a walk in closet, and its bathroom features double sinks and a separate tub and shower. Outside, a patio connects to an in ground pool within a fenced in backyard.

Karen Albright OPENDOOR BROKERAGE LLC

51 Oakleigh Ln, Maitland, FL 32751
/17
$2,295 Per Month
- 4 Beds
- 3 Baths
- 2,300 Sq Ft
- Townhouse for Rent
243 W Lake Faith Dr, Maitland, FL 32751

Don't miss out on this large 4 bed 3 bath town home in a fantastic location! Rare find with 2,300/SF of living space. Fresh paint, new carpet and large kitchen with granite counters and new fridge. All 4 bedrooms are very nice sizes (there is one large bedroom and bathroom downstairs and all others are upstairs, including the master bedroom). You won't believe the additional closet and storage

243 W Lake Faith Dr, Maitland, FL 32751
/2
$385,000 Sold Feb 24, 2026

210 Magnolia Rd Unit 106, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,394 Sq Ft
- Built 1971
Last Sold Summary
- 4% Below List Price
- $276/SF
- 16 Days On Market
Current Estimated Value $385,258

Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

210 Magnolia Rd Unit 106, Maitland, FL 32751

/34
Est $261,856 Not Listed For Sale

852 Park Lake Cir Unit 49, Maitland, FL 32751
- 3 Beds
- 3 Baths
- 1,496 Sq Ft
- Built 1972
852 Park Lake Cir Unit 49, Maitland, FL 32751

Last Sold Summary
- 9% Below List Price
- $193/SF
- 43 Days On Market
- Last Sold Price $289,000
- May 24, 2024
Last Listing Agent Eddie Cooper MAINFRAME REAL ESTATE

/69
$2,395,000
- 5 Beds
- 3 Baths
- 3,456 Sq Ft
530 Lake Catherine Dr, Maitland, FL 32751

An incredible opportunity in one of Maitland’s most exclusive communities offers stunning lakefront views of both Lake Catherine and Lake Eulalia. With one of only three private docks on Lake Catherine, this is truly a rare and special property. A charming brick street winds along the lake and leads to this timeless residence, uniquely positioned with frontage on two lakes. This elegant two-story

Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

530 Lake Catherine Dr, Maitland, FL 32751
/12
$1,950 Per Month
- 4 Beds
- 2 Baths
- 1,372 Sq Ft
- Condo for Rent
1175 Lake Shadow Cir Unit 4207, Maitland, FL 32751

Great 4 bedroom condo available in a fantastic gated community. Visconti has a lot to offer its residents, from swimming pool, tennis, basketball, nature walks, fitness center, club house, etc. This community is located in close proximity to I-4 and Maitland exchange.

Mona Rodriguez CAPITAL REALTY GROUP FLORIDA

1175 Lake Shadow Cir Unit 4207, Maitland, FL 32751
/2
$555,000 Sold Oct 01, 2025

1771 Chinook Trail, Maitland, FL 32751
- 2 Beds
- 2 Baths
- 1,704 Sq Ft
- Built 1959
Last Sold Summary
- 4% Below List Price
- $326/SF
- 20 Days On Market
Current Estimated Value $557,301

Last Listing Agent Hazel Sun RE/MAX 200 REALTY

1771 Chinook Trail, Maitland, FL 32751

/51
Est $277,565 Not Listed For Sale

903 Town Cir Unit 194, Maitland, FL 32751
- 3 Beds
- 2.5 Baths
- 1,565 Sq Ft
- Built 1979
903 Town Cir Unit 194, Maitland, FL 32751

Last Sold Summary
- 9% Below List Price
- $195/SF
- 105 Days On Market
- Last Sold Price $305,000
- Jun 07, 2024
Last Listing Agent Reeta Gulati RE REALTY

/32
$1,975,000
- 4 Beds
- 3.5 Baths
- 3,754 Sq Ft
1111 Audubon Way, Maitland, FL 32751

Welcome to a rare opportunity on the shores of Lake Sybelia, one of Maitland’s most desirable recreational lakes. This custom, one-owner home offers 3,754 square feet of thoughtfully designed living space that has been well-maintained with potential for cosmetic enhancements. A brick-paved horseshoe driveway and inviting front porch set the tone. Inside, rich wood floors, vaulted wood ceilings in

Melissa Shipp KELLER WILLIAMS ADVANTAGE REALTY

1111 Audubon Way, Maitland, FL 32751
/8
$1,185 Per Month
- 2 Beds
- 1 Bath
- Condo for Rent
114 Eaton St Unit 3, Eatonville, FL 32751

O/LB - 2 Bedroom, 1 Bath, Living Room, Eat In Kitchen, Quad-Plex! Apply Today! If you would like to view this property, and TO SCHEDULE A SHOWING PLEASE EMAIL US AT FOR AVAILABLE SHOW TIMES. Please send us your Name, Phone Contact and Email Address. All Showings are done Monday thru Friday between 10am & 2pm.Offering a $100 Special upon approval!HOW TO APPLY/ABOUT OUR

114 Eaton St Unit 3, Eatonville, FL 32751
/2
$595,000 Sold May 05, 2026

2466 Fieldingwood Rd, Maitland, FL 32751
- 4 Beds
- 2 Baths
- 1,765 Sq Ft
- Built 1972
Last Sold Summary
- 1% Below List Price
- $337/SF
- 2 Days On Market
Current Estimated Value $351,825

Last Listing Agent Kristine McKinley RE/MAX TOWN & COUNTRY REALTY

2466 Fieldingwood Rd, Maitland, FL 32751

/29
Est $381,431 Not Listed For Sale

1840 Rogers Ave, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,458 Sq Ft
- Built 2024
1840 Rogers Ave, Maitland, FL 32751

Last Sold Summary
- $261/SF
- 3 Days On Market
- Last Sold Price $380,000
- Mar 08, 2024
Last Listing Agent Mario Zendeli COMPASS FLORIDA LLC

/28
$479,900 Pending
- 4 Beds
- 2 Baths
- 1,879 Sq Ft
1928 South Blvd, Maitland, FL 32751

Under contract-accepting backup offers. A rare Maitland find that combines a spacious 4-bedroom layout. Enjoy the freedom of a non-flood zone and no HOA fees or restrictions. The "Big Three" are already done: Roof (2022), HVAC (2023), and Water Heater (2024). Bonus: Original windows successfully passed all 4-point and wind mitigation inspections. Inside, a wide-open interior is flooded with

Doori Sung LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

1928 South Blvd, Maitland, FL 32751
/23
$1,600 Per Month
- 2 Beds
- 2 Baths
- 1,048 Sq Ft
- Condo for Rent
1408 Lake Shadow Cir Unit 1304, Maitland, FL 32751

Minutes away from the Maitland business center, I-4, Winter Park and downtown Orlando. Beautiful 2 bedroom 2 bathroom condominium in the gated community of Visconti. The first floor condominium offers community amenities include a resort style pool, fitness center, valet trash service, car wash, basketball and tennis courts.

Matthew Angell VIDA REAL ESTATE SERVICES LLC

1408 Lake Shadow Cir Unit 1304, Maitland, FL 32751
/2
$239,000 Sold May 08, 2026

602 Villa Cir Unit 543, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,256 Sq Ft
- Built 1979
Last Sold Summary
- 4% Below List Price
- $190/SF
- 49 Days On Market
Current Estimated Value $245,557

Last Listing Agent Odel Ximinies COLDWELL BANKER REALTY

602 Villa Cir Unit 543, Maitland, FL 32751

/2
Est $527,000 Not Listed For Sale

229 Quayside Cir Unit C, Maitland, FL 32751
- 3 Beds
- 2.5 Baths
- 1,652 Sq Ft
- Built 1985
229 Quayside Cir Unit C, Maitland, FL 32751

Last Sold Summary
- 4% Below List Price
- $333/SF
- 92 Days On Market
- Last Sold Price $550,000
- May 10, 2024
Last Listing Agent MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

/13
$120,000
- 1 Bed
- 1 Bath
- 550 Sq Ft
2517 Caper Ln Unit 205, Maitland, FL 32751

**ATTENTION INVESTORS** Take advantage of this great opportunity and Add this income producing property to your portfolio with tenant in place. Corner unit 1 bed 1 bath condo with new laminate floors and granite countertops. This second floor unit means there is no one above you and has a pool view located steps away. The mailbox and pool are only a few steps away. Location is walking distances

MAYOLET BORNAS MAYOLET REALTY LLC

2517 Caper Ln Unit 205, Maitland, FL 32751
/20
$2,500 Per Month
- 3 Beds
- 2.5 Baths
- 2,042 Sq Ft
- House for Rent
7915 Chartreux Ln, Maitland, FL 32751

GORGEOUS single-family home located in beautiful Maitland, FL.This spacious 3-bedroom, 2.5-bathroom residence offers approximately 2,042 sq. ft. of comfort and style, including a large bonus loft that overlooks the garden area—perfect as a TV room, additional living space, or home office.The home features an open-concept kitchen, indoor fireplace, and an elegant stairway leading to

7915 Chartreux Ln, Maitland, FL 32751
/2
$1,820,000 Sold Jun 07, 2025

251 W Trotters Dr, Maitland, FL 32751
- 4 Beds
- 2.5 Baths
- 3,524 Sq Ft
- Built 1964
Last Sold Summary
- 4% Below List Price
- $516/SF
- 8 Days On Market
Current Estimated Value $1,831,908

Last Listing Agent Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

251 W Trotters Dr, Maitland, FL 32751

/12
Est $363,814 Not Listed For Sale

1920 Rogers Ave, Maitland, FL 32751
- 3 Beds
- 2 Baths
- 1,559 Sq Ft
- Built 2023
1920 Rogers Ave, Maitland, FL 32751

Last Sold Summary
- 1% Below List Price
- $237/SF
- 32 Days On Market
- Last Sold Price $369,000
- Feb 12, 2024
Last Listing Agent Keishawn Thomas KELLER WILLIAMS REALTY AT THE PARKS

/34
$599,000
- 3 Beds
- 3.5 Baths
- 1,966 Sq Ft
502 Oak Ln, Maitland, FL 32751

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,

Andre Kressler KRESSLER REAL ESTATE

502 Oak Ln, Maitland, FL 32751
/34
$1,550 Per Month
- 1 Bed
- 1 Bath
- 612 Sq Ft
- Condo for Rent
1140 S Orlando Ave Unit E2, Maitland, FL 32751

Live the lakefront lifestyle in this beautifully updated 1-bedroom condo located in the iconic mid-century modern community of Lake Maitland Terrace. Freshly painted and completely refreshed, this residence features brand-new appliances, a brand-new air conditioning system, and stunning new wood flooring throughout the main living areas. The bedroom offers sleek, modern concrete flooring—adding

Beatrice Miranda METRO CITY REALTY

1140 S Orlando Ave Unit E2, Maitland, FL 32751
/2
$515,000 Sold Nov 07, 2025

2162 Lake Howell Preserve Ct, Maitland, FL 32751
- 3 Beds
- 3.5 Baths
- 2,188 Sq Ft
- Built 2021
Last Sold Summary
- 6% Below List Price
- $235/SF
- 27 Days On Market
Last Listing Agent Mark Raumaker SERHANT

2162 Lake Howell Preserve Ct, Maitland, FL 32751

/65
Est $255,753 Not Listed For Sale

804 Park Lake Cir Unit 3, Maitland, FL 32751
- 3 Beds
- 3 Baths
- 1,575 Sq Ft
- Built 1972
804 Park Lake Cir Unit 3, Maitland, FL 32751

Last Sold Summary
- 7% Below List Price
- $175/SF
- 52 Days On Market
- Last Sold Price $275,000
- Feb 23, 2024
Last Listing Agent Amber Finch FINCH REAL ESTATE COMPANY

Showing Results 161 - 200, Page 5 of 18

Florida Orange County Maitland

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Maitland, FL Homes

Real Estate & Homes