Browse All Lake Mary FL Historical Properties for Sale

4 Beds ⋅ 2 Baths ⋅ The Cove SubDv. ⋅ 32746 Zip Code

**Never before offered for sale**, this extraordinary six-acre lakefront estate presents a once-in-a-generation opportunity to acquire one of Lake Mary's most remarkable legacy properties. Set behind the private gates of The Cove, yet uniquely exempt from the community's HOA, the estate is hidden at the end of a long, tree-lined private drive where the landscape unfolds dramatically to reveal more than 800 feet of pristine Crystal Lake shoreline. Spectacular sunset views, abundant wildlife, and the timeless beauty of Old Florida create a setting that has become exceedingly rare. High and dry with an expansive homesite overlooking the water, the property offers exceptional flexibility for those envisioning a custom waterfront estate unlike anything else in the area. Whether designing a grand primary residence with a guest house, resort-inspired outdoor living, expansive garages, or recreational amenities, the scale, privacy, and extraordinary waterfront frontage provide an unparalleled foundation for a truly exceptional estate. The existing century-old home reflects the property's rich history, while a detached two-car garage with an attached bonus room and a separate four-car garage complete with a workshop and expansive storage room provide immediate functionality while future plans take shape. What truly distinguishes this offering is the rare balance of privacy and convenience. Enjoy the exclusivity and security of a gated community without the limitations of HOA restrictions, an increasingly uncommon advantage for luxury buyers seeking the freedom to create a deeply personalized estate. Located just minutes from Lake Mary's thriving Midtown district, residents enjoy an exceptional collection of acclaimed restaurants, boutique shopping, cafés, entertainment, fitness studios, and community events, while nearby Interstate 4, SR 417, and the Wekiva Parkway provide effortless access to downtown Orlando, area airports, world-famous attractions, pristine beaches, and the very best of Central Florida. Properties of this significance are rarely available, especially those remaining in the same family and offered to the public for the very first time. Combining more than 800 feet of Crystal Lake shoreline, six picturesque acres, remarkable privacy, spectacular sunsets, and one of Lake Mary's most desirable locations, 2636 Reagan Trail presents a once-in-a-generation opportunity to create a waterfront estate that will be cherished for generations to come.

2636 Reagan Trail, Lake Mary

$250,000

1 Beds ⋅ 1 Baths ⋅ Crystal Lake Winter Homes SubDv. ⋅ 32746 Zip Code

Investor opportunity in a great Lake Mary location! Public records show this home as a 1 bedroom, 1 bath with 855 sq ft, but the property offers much more potential. The existing layout could easily be reimagined as a 2 bedroom, 1 bath, giving buyers the chance to add value and maximize the space. Situated on a nice .25 acre fenced lot, this property also features a large detached workshop with electric and plumbing already in place, creating exciting potential for a studio, guest space, home office, or possible ADU conversion. Buyer to verify all zoning, permitting, and intended use. Bring your vision and creativity. This property is being sold As Is, allowing the next owner to imagine the possibilities and make it their own. Great opportunity for investors, renovators, or buyers looking for a project with upside potential!

168 W Wilbur Avenue, Lake Mary

$350,000

3 Beds ⋅ 2 Baths ⋅ Glenwood SubDv. ⋅ 32746 Zip Code

Welcome to 178 Washington Avenue, Lake Mary. This 3 Bedroom, 2 Full Bathroom home has a split floor plan and is walking distance to downtown Lake Mary. Situated on a corner lot of nearly half an acre with mature trees and NO HOA. The back yard is fully fenced. Updates: New electrical panel and wiring throughout home 2022, septic & drainfield replaced 2020, home replumbed 2022. Tile & laminate floors throughout the home -- no carpet. This is a great opportunity to buy in the area and make the home your own. Zoned for Lake Mary Elementary, Greenwood Lakes Middle and Lake Mary High.

178 Washington Avenue, Lake Mary

$284,999

3 Beds ⋅ 2 Baths ⋅ Crystal Lake Winter Homes SubDv. ⋅ 32746 Zip Code

Virtually Staged. Located just moments from downtown Lake Mary, this single-story home offers an exceptional opportunity in a highly desirable area. Featuring three bedrooms and two bathrooms, the property provides a spacious layout with over 1,400 square feet of living space. Enjoy the convenience of being close to local restaurants, boutique shops, and the popular Saturday farmer’s market. Situated on a fenced lot with driveway parking, this home is ideal for buyers looking to renovate, invest, or create a personalized space in a prime location close to major roadways and everyday amenities.

170 W Crystal Lake Avenue, Lake Mary

$599,900

Crystal Lake Winter Homes SubDv. ⋅ 32746 Zip Code

BIG PRICE REDUCTION!!! Rare commercially zoned lot in downtown Lake Mary square connected to the vibrant shopping and dining district! Directly adjacent to Central Park at City Hall, downtown shops and restaurants, and walking distance to Lake Mary Sunrail Station. Property is zoned "DC" - Downtown Centre - Refer to chapter 154.67 in the Code of Ordinances. Allows for retail, office, restaurants, possible 2-story Live/Work opportunity. Sewer and water hooked up to residence. Micro retail development with salon space under construction on the southeast corner of 4th and Crystal Lake Ave, townhome projects proposed one block away on Wilbur Ave. City of Lake Mary has approved front parking on Crystal Lake and there is paved public parking on the corner and across the street. Located near City Hall, many great dining places, shopping, I-4, Lake Mary Blvd., and 417. Lots of exposure for your business and great foot traffic. Value is in the land. Similar commercial lot now under construction on the corner sold for $899,000!

160 N 4th Street, Lake Mary

Start Your Search

Lake Mary Historical Real Estate

Our website features the best real estate search for historical properties available in Lake Mary and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!