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Maitland Real Estate Search

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Maitland Homes for Sale

The well-established city of Maitland in Central Florida presents homebuyers with lovely condos, townhomes, and single-family homes for sale to choose from. Waterfront homes in Maitland showcase views of the 20 lakes including the especially beautiful Lake Lucien and Lake Sybella. Affordable houses in Maitland are discoverable with open layouts consisting of between three and four bedrooms across 1,000-3,000+ square-foot floor plans. 

The city of Maitland is situated in Orange County, Florida and became incorporated in 1959. This Orlando suburb is currently populated by more than 17,000 people spanning just six square miles and features a whopping 21 lakes throughout the city.

Hopeful residents looking to buy one of the Maitland houses for sale can find beautiful properties near major thoroughfares like a local SunRail Station, Orlando Avenue, and the I-4, making commuting in and out of the city that much easier.

History and art aficionados are able to enrich their lives by visiting sites like the Maitland Historical Museum, the Maitland Art Center, and the Maitland Telephone Museum. The independent Enzian Theater is a local staple, and the Florida Film Festival is held in Maitland as well.

Active homeowners are encouraged to test out the RDV Sportsplex or hang at beautiful outdoor spaces like Lake Lily Park, Maitland Community Park, or Minnehaha Park where visitors can play tennis or fish. 

Living in this community allows homebuyers to remain in a bustling city while coming home to private, peaceful lakeside living. If you are interested in purchasing one of the Maitland homes or condos for sale in Florida, please contact us today. 

1160 Willowbrook Trail, Maitland image
1160 Willowbrook Trail, Maitland $950,000

Marvelous Mid Century Classic Traditional offers many options in family living including a unique multi level floor plan. The split level home upstairs accommodates the m...

  • 5 Beds
  • 3.5 Baths
  • Maitland Woods SubDv.
  • 32751 Zip Code
103 Whitecaps Circle, Maitland image
103 Whitecaps Circle, Maitland $529,900

This charming 3/2 mid-century ranch is an amazing home. The open floorpan as you enter has beautiful hardwood floors, the family room area has terrazzo with a beautiful s...

  • 3 Beds
  • 2 Baths
  • Hollieanna Shores 1st Add SubDv.
  • 32751 Zip Code
2015 Mohawk Trail, Maitland image
2015 Mohawk Trail, Maitland $699,000

Lovely 4 BDRM/2BATH home located in much sought after Dommerich Estates. Best Feature: Brand New Roof just completed. There is plenty of space to spread out with separat...

  • 4 Beds
  • 2 Baths
  • Dommerich Hills SubDv.
  • 32751 Zip Code
1700 Cheyenne Trail, Maitland image
1700 Cheyenne Trail, Maitland $595,000

Dommerich Estates home with an open and spacious floor plan including 4 large picture windows in the living areas bringing in plenty of natural light. Just under 2000 sf,...

  • 3 Beds
  • 2 Baths
  • Dommerich Estates 1st Add SubDv.
  • 32751 Zip Code
1160 Kewannee Trail, Maitland image
1160 Kewannee Trail, Maitland $805,000

**Fully Renovated** Stunning home located in the sought after Dommerich community of Maitland. 5 bed / 3 full baths detailed with elegance and perfection, this home has i...

  • 5 Beds
  • 3 Baths
  • Dommerich Hills 3rd Add SubDv.
  • 32751 Zip Code
171 Dommerich Drive, Maitland image
171 Dommerich Drive, Maitland $750,000

Come and see this newly remodeled Dommerich Estates home! The home boasts 3 completely updated bedrooms with new carpet and trim, fresh paint, new LED lighting and new ce...

  • 3 Beds
  • 2.5 Baths
  • Dommerich Estates SubDv.
  • 32751 Zip Code
2100 Geronimo Trail, Maitland image
2100 Geronimo Trail, Maitland $799,900

One or more photo(s) has been virtually staged. *** Updated & Designed for Entertaining *** Open Concept *** Large Kitchen *** Latest design trend of Natural Wood Cabinet...

  • 4 Beds
  • 2.5 Baths
  • Highland Park Estates SubDv.
  • 32751 Zip Code
2330 Huron Trail, Maitland image
2330 Huron Trail, Maitland $649,900

Welcome home to this Dommerich Hills 3 bedroom PLUS OFFICE beauty! Pride of ownership is featured throughout this amazing property. Absolutely STUNNING oversized lot with...

  • 3 Beds
  • 2 Baths
  • Dommerich Hills First Add SubDv.
  • 32751 Zip Code
2305 Haywood Court Unit 101, Maitland image
2305 Haywood Court Unit 101, Maitland — 2305 $170,000

This very spacious first floor condo offers 2 large bedrooms and nice open floor plan. The private enclosed patio perfect for relaxing while enjoying the peaceful view o...

  • 2 Beds
  • 2 Baths
  • Carrington Park A Condo SubDv.
  • 32751 Zip Code
1700 Lyndale Boulevard, Maitland image
1700 Lyndale Boulevard, Maitland $1,499,000

Enjoy an exquisite living experience in this custom built Dave Cahill Home. Mediterranean style with Spanish tile roof located on a beautiful corner lot. You are greet...

  • 4 Beds
  • 4.5 Baths
  • Dixie Terrace SubDv.
  • 32751 Zip Code
801 S Lake Destiny Road, Maitland image
801 S Lake Destiny Road, Maitland $500,000

Waterfront 3 Parcel Offering with single family home. Awesome opportunity to renovate home and have fabulous waterfront property. This is a total renovation so bring an ...

  • 3 Beds
  • 2 Baths
  • N/A SubDv.
  • 32751 Zip Code
761 S Lake Destiny Road, Maitland image
761 S Lake Destiny Road, Maitland $225,000

Cozy 2 bedroom home just needs your finishing touches to make it your own. Nice terrazo flooring throughout. Spacious living room with bonus room. Fenced yard and conven...

  • 2 Beds
  • 1.5 Baths
  • N/A SubDv.
  • 32751 Zip Code
1938 Bobtail Drive, Maitland image
1938 Bobtail Drive, Maitland $415,000

Beautiful three bedroom, two bath Maitland home located in a charming neighborhood. Living/dining room combo with high vaulted ceilings and freshly painted walls. The Kit...

  • 3 Beds
  • 2 Baths
  • Winfield SubDv.
  • 32751 Zip Code
865 Cranes Court, Maitland image
865 Cranes Court, Maitland $995,000

MAITLAND GATED COMMUNITY / Exquisite Pool Home! Nested between Lake Catherine and Lake Sybelia is the best-kept hidden little secret known as Lake Sybelia Cove of 19 cus...

  • 4 Beds
  • 3.5 Baths
  • Lake Sybelia Cove Ph 01 SubDv.
  • 32751 Zip Code
2241 Deloraine Trail, Maitland image
2241 Deloraine Trail, Maitland $609,000

A beautiful Dommerich Neighborhood Pool home in the peaceful, tree lined streets of the highly sought after Dommerich Elementary, Maitland Middle & Winter Park High schoo...

  • 3 Beds
  • 2 Baths
  • Highland Park Estates First Add SubDv.
  • 32751 Zip Code
707 Thunder Trail, Maitland image
707 Thunder Trail, Maitland $750,000 ▼

This stunning Dommerich 2900 SF, 4 bedroom/2 Bath pool home with bonus room, is what you have been waiting for! Beautiful finishes throughout including wood flooring, pla...

  • 4 Beds
  • 2 Baths
  • Dommerich Hills Second Add SubDv.
  • 32751 Zip Code
2631 Derbyshire Road, Maitland image
2631 Derbyshire Road, Maitland $499,900

Charming Home this home offers spacious 4 bedrooms and 2 bath open kitchen with new granite counter top, also offer a bonus room perfect for a den or office . Renovated m...

  • 4 Beds
  • 2 Baths
  • Indian Hills Unit 1 Rep SubDv.
  • 32751 Zip Code
1140 S Orlando Avenue Unit 11, Maitland image
1140 S Orlando Avenue Unit 11, Maitland — Arlington $228,750

LOCATION!! GREAT AMENITIES!! - Lake Maitland ACCESS!! Great "A" rated Schools!! WOW - Another Lake Maitland Terrace condo is NOW available. Enjoy the simple living in thi...

  • 1 Beds
  • 1 Baths
  • Lake Maitland Terrace Apts SubDv.
  • 32751 Zip Code
446 Cherrywood Gardens, Maitland image
446 Cherrywood Gardens, Maitland — 446 $209,999

One or more photo(s) has been virtually staged. Lovely 2 bedroom, 2 full bath condo in the sought after neighborhood Cherrywood Gardens. This is one of the bigger units s...

  • 2 Beds
  • 2 Baths
  • Cherrywood Gardens SubDv.
  • 32751 Zip Code
1980 Kenaston Road, Maitland image
1980 Kenaston Road, Maitland — 1980 $399,000

Absolutely gorgeous private end unit near pool, surrounded by mature trees that offer a peaceful environment. Home offers beautiful Bamboo flooring, Plantation shutters t...

  • 3 Beds
  • 3 Baths
  • Ultra Vista Condo SubDv.
  • 32751 Zip Code
291 W Lake Faith Drive Unit 142, Maitland image
291 W Lake Faith Drive Unit 142, Maitland — 142 $268,900

Adorable two bedroom and two and a half bathroom condo located in the highly desirable Maitland, Florida. Completely updated two-story townhome-like condo in the Lake Fai...

  • 2 Beds
  • 2.5 Baths
  • Lake Faith Villas Condo SubDv.
  • 32751 Zip Code
2450 Derbyshire Road, Maitland image
2450 Derbyshire Road, Maitland $685,000 ▼

FULLY RENOVATED. Jump on this incredible opportunity for a stunning, move-in ready property in the highly sought-after English Estates Maitland neighborhood just minutes ...

  • 4 Beds
  • 2.5 Baths
  • English Estates Unit 2 SubDv.
  • 32751 Zip Code
518 Oranole Road, Maitland image
518 Oranole Road, Maitland $390,000

Come in and experience this Mid century style home. Built on an oversized lot, the backyard is fenced in, perfect for kids to play in or pets to run around. Enjoy the mat...

  • 3 Beds
  • 1.5 Baths
  • Oakland Shores SubDv.
  • 32751 Zip Code
412 Lake Howell Road, Maitland image
412 Lake Howell Road, Maitland $395,000

Perfect Office For An End User or someone who needs office space and/or income from the M-T-M tenants. Consisting of 6 rooms / offices. Multiple Use Options, Including ...

  • Lake Howell Comm Cntr SubDv.
  • 32751 Zip Code
165 N Lakewood Circle, Maitland image
165 N Lakewood Circle, Maitland $440,000

One or more photo(s) has been virtually staged. This Maitland one-story home offers granite countertops, and a two-car garage.

  • 3 Beds
  • 2 Baths
  • Lakewood Shores SubDv.
  • 32751 Zip Code
734 Terra Place, Maitland image
734 Terra Place, Maitland $499,999

This is the very last lot in Maitland’s best-kept-secret neighborhood, Terra Place. Located on a quiet cul-de-sac with mature trees and great neighbors, this oversized 0....

  • Terra Place SubDv.
  • 32751 Zip Code
1770 Algonquin Trail, Maitland image
1770 Algonquin Trail, Maitland $550,000 ▼

PRICE REDUCED - This lovely home in the Dommerich neighborhood is in an amazing location in Maitland. It has a wonderful 4/2 floorplan with lush and mature landscaping. L...

  • 4 Beds
  • 2 Baths
  • Dommerich Estates 1st Add SubDv.
  • 32751 Zip Code
1000 Winderley Place Unit 246, Maitland image
1000 Winderley Place Unit 246, Maitland — 1000 $335,000

This beautiful 3-bedroom, 2-bathroom newly fully renovated unit located within a private, gated, lakefront community in lovely Maitland, Florida checks all the boxes! You...

  • 3 Beds
  • 2 Baths
  • Sun Bay Club SubDv.
  • 32751 Zip Code
447 Lake Howell Road, Maitland image
447 Lake Howell Road, Maitland $899,000

Turn key, stand alone office building with all furnishings included! Move right in! This 2,700+ square foot building has a reception area, 8 current offices, 1 executive...

  • Acreage & Unrec SubDv.
  • 32751 Zip Code
140 E Faith Terrace, Maitland image
140 E Faith Terrace, Maitland $399,900

MAITLAND HOME WITH ENDLESS POTENTIAL! Magnificent classic Mid-century modern home just off of Lake Seminary and located on a quiet street. This home is waiting for someon...

  • 3 Beds
  • 2 Baths
  • Northwood Heights SubDv.
  • 32751 Zip Code
2814 Shadow View Circle Unit 2814, Maitland image
2814 Shadow View Circle Unit 2814, Maitland — Na $329,000

Great investment opportunity! Spacious 3 bedroom, 2.5 bath condo in the gated community of Visconti East. Generous two car garage on the first level. Updated kitchen w...

  • 3 Beds
  • 2.5 Baths
  • Visconti East SubDv.
  • 32751 Zip Code
668 N Orlando Avenue Unit 1009, Maitland image
668 N Orlando Avenue Unit 1009, Maitland $599,000

Fantastic Ground Floor unit in Maitland Exchange Office Complex. Unit consists of 2 separate office spaces that could easily be made into 1 large unit! Both units feature...

  • 32751 Zip Code
30 Johnson Street, Eatonville image
30 Johnson Street, Eatonville $332,000 ▼

Great Family Home or Investment property. Oversized lot allows a legal lot split. The property is located within an Opportunity Zone and LMI census tract. Therefore, up t...

  • 4 Beds
  • 3 Baths
  • Eaton Manor SubDv.
  • 32751 Zip Code
2449 Legacy Lake Drive Unit 2449, Maitland image
2449 Legacy Lake Drive Unit 2449, Maitland — 24 $303,000 ▼

One or more photo(s) has been virtually staged. Welcome to this gorgeous neighborhood! Terrific 3 bedroom and 2.5 bath home with a 2 car garage. Enjoy preparing meals in ...

  • 3 Beds
  • 2.5 Baths
  • Visconti East SubDv.
  • 32751 Zip Code
1000 Winderley Place Unit 222, Maitland image
1000 Winderley Place Unit 222, Maitland — 1 $355,000

LOCATION! Move-in ready home located in Maitland walking distance to RDV Sportsplex Athletic Club. Gated lakefront community a few miles from downtown Orlando. This 2 bed...

  • 2 Beds
  • 2 Baths
  • Sun Bay Club Condo SubDv.
  • 32751 Zip Code
2638 Legacy Villas Drive Unit 2638, Maitland image
2638 Legacy Villas Drive Unit 2638, Maitland — Visconti East $299,000

Among the exclusive standard touches available are upgraded carpet & pad, track lighting in kitchen & dining areas and contemporary tile in foyer, kitchen & bathroom area...

  • 2 Beds
  • 2 Baths
  • Visconti East SubDv.
  • 32751 Zip Code
1000 Winderley Place Unit 128, Maitland image
1000 Winderley Place Unit 128, Maitland $265,000

Gated lakefront community in beautiful Maitland. Right off Maitland Blvd. and I-4. This 2 bedroom 2 bath on the ground floor with sliding glass doors in every room. 3 ...

  • 2 Beds
  • 2 Baths
  • Sun Bay Club Condo SubDv.
  • 32751 Zip Code
615 Lake Shore Drive, Maitland image
615 Lake Shore Drive, Maitland $700,000

Beautifully appointed in the heart of Maitland along Lake Shore Drive, this exquisite mid-century modern masterpiece combines privacy and sophistication for your enjoymen...

  • 3 Beds
  • 3 Baths
  • Oakland Shores SubDv.
  • 32751 Zip Code
2923 Shadow View Circle Unit 2923, Maitland image
2923 Shadow View Circle Unit 2923, Maitland — 30 $305,000

Work, live, and play in the elegant Visconti gated community a desirable condominium in Maitland City, Florida. This elegant Updated and upgraded 2 bedrooms and 2 bathroo...

  • 2 Beds
  • 2 Baths
  • Visconti East SubDv.
  • 32751 Zip Code
500 Banyon Tree Circle Unit 104, Maitland image
500 Banyon Tree Circle Unit 104, Maitland — Building 34 $215,999

This very spacious 3 bedroom/2 bath Maitland condo is your investment property to own in Carrington Park! This condo is in walking distance to the shops and restaurants i...

  • 3 Beds
  • 2 Baths
  • Carrington Park A Condo SubDv.
  • 32751 Zip Code
670 Old Horatio Avenue, Maitland image
670 Old Horatio Avenue, Maitland $839,000

CANAL FRONT in WINTER PARK CHAIN of LAKES on BUILDABLE LEVEL LOT ! 85 ft. of canal with sea wall, boat slip, deck & dry land 85 x 149, Total lot is 85 x 203. Waterfront &...

  • 3 Beds
  • 1 Baths
  • Long Branch Sub SubDv.
  • 32751 Zip Code
331 N Maitland Avenue Unit C-3, Maitland image
331 N Maitland Avenue Unit C-3, Maitland $259,000 ▼

If you have been searching for a one story office condo in Maitland your search is finally over! This one story end unit (C-3) has two entrances, one front and one rear. ...

  • Maitland Square SubDv.
  • 32751 Zip Code
120 Woodstream Court, Maitland image
120 Woodstream Court, Maitland $2,699,000 ▼

Welcome home to this beautiful contemporary lakefront home located on the Winter Park Chain of Lakes! With a plethora of recent improvements this home is sure to impress ...

  • 4 Beds
  • 4 Baths
  • Woodstream SubDv.
  • 32751 Zip Code
155 Oakleigh Lane, Maitland image
155 Oakleigh Lane, Maitland $5,200,000

One or more photo(s) has been virtually staged. Established on the shores of Lake Maitland privately navigable on Winter Park Chain of Lakes you will love this CUSTOM Cla...

  • 4 Beds
  • 4.5 Baths
  • Under Oaks SubDv.
  • 32751 Zip Code
125 Stone Hill Drive, Maitland image
125 Stone Hill Drive, Maitland $3,750,000

One or more photo(s) has been virtually staged. Welcome to your custom built "Mediterranean style" home at private Lake Seminary! This breathtaking 8,190 SQFT with 9 Bedr...

  • 9 Beds
  • 7 Baths
  • Stonehill SubDv.
  • 32751 Zip Code
2420 Mcintosh Way, Maitland image
2420 Mcintosh Way, Maitland $850,000 ▼

Incredible opportunity to live in Dommerich, one of Central Florida's most desirable neighborhoods. The home is tucked away on a picturesque street just minutes from top-...

  • 6 Beds
  • 4 Baths
  • Highland Park Estates First Add SubDv.
  • 32751 Zip Code
832 Brookside Road, Maitland image
832 Brookside Road, Maitland $484,900 ▼

Are you looking for a well-established Maitland neighborhood in desirable Seminole County? This is the one for you! This 3 bedroom 2 bath home sits on a corner lot that ...

  • 3 Beds
  • 2 Baths
  • Forest Brook 4th Sec SubDv.
  • 32751 Zip Code
570 Manor Road, Maitland image
570 Manor Road, Maitland $4,950,000 ▼

Located directly on Lake Maitland the largest lake on the “Winter Park Chain of Lakes”, 15 minutes to downtown Orlando, this beautifully constructed gated estate offers a...

  • 6 Beds
  • 7.5 Baths
  • Lake Maitland Manor SubDv.
  • 32751 Zip Code
175 Lookout Place, Maitland image
175 Lookout Place, Maitland $1,400,000

Stand alone office building completely renovated down to studs in 2020 with new flooring, lighting, paint both inside and out; in-place income from 2nd floor user; 1st fl...

  • Keewin Lexington Park SubDv.
  • 32751 Zip Code
640 Robinhood Drive Unit B, Maitland image
640 Robinhood Drive Unit B, Maitland — 640 $207,500 ▼

Two bedroom condominium with private screened patio and two reserved parking spaces in downtown Maitland. Spacious living and dining area includes tile flooring throughou...

  • 2 Beds
  • 1 Baths
  • Robinhood Villas Condo 02 SubDv.
  • 32751 Zip Code
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Orlando Real Estate Services
468 Lancers Dr.
Winter Springs, Florida 32708

Phone: 407-443-7200
Fax: 407-327-7187
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