Vintage homes for sale & real estate in Hernando County, FL

35 homes

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ABOUT THIS HOME
Vintage Home for sale in Hernando County, FL:
Nearly 2.5 Acres, a 1946 Charmer & a Garage That Means Business! Looking for a home with character? How about character, acreage, history, and a garage that could probably run its own small business? Welcome to this charming 1946 Brooksville original, sitting on nearly 2.5 acres right in historic downtown. Yes, you read that correctly—almost 2.5 acres, downtown. Because apparently, this property didn’t get the memo that downtown living is supposed to mean giving up your elbow room. The home features 2 bedrooms (can be 3 bedrooms), 2 bathrooms, and an office/bonus room—perfect for working from home, hobbies, guests, or that room you swear will eventually be organize

$350,000

2 beds2 baths1,236 sq ft

1205 S Main St, Brooksville, FL 34601

Historic downtown • Nearly 2.5 acres • Detached garage

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Hernando County, FL:
Virtually Staged. Welcome to this well-maintained 2-bedroom, 1-bath home offering 1,119 square feet on a fully fenced . 69-acre lot with NO HOA! Tucked away in a quiet neighborhood yet conveniently located just about 4 miles from I-75, grocery stores, restaurants, and everyday conveniences, this property offers plenty of space both inside and out. Step inside to an open living and dining area with a spacious kitchen featuring wood cabinetry and plenty of workspace. Brand-new laminate flooring was installed in 2026 as well as fresh, new interior paint, adding a fresh, updated look throughout the home. Just off the living room is a Florida room overlooking the rear deck and pool area, creatin

$259,900

2 beds1 bath1,119 sq ft

5223 Azalea Cir, Dade City, FL 33523

Large wooden deck • Spacious kitchen • Florida room

ABOUT THIS HOME
Vintage Home for sale in Hernando County, FL:
* * ROOF 2026-HVAC 2023-MAIN PANEL 2023-WATER HEATER 2023-SURVEY AVAILABLE * * Welcome to this charming property in Brooksville, Florida, where you can enjoy the freedom of NO HOA fees and the relaxed lifestyle that makes Hernando County so desirable. Whether you're looking for a primary residence, seasonal getaway, or investment opportunity, this property offers flexibility without the added costs or restrictions of a homeowners association. Ideally located, you'll enjoy convenient access to Historic Downtown Brooksville, known for its locally owned restaurants, boutiques, coffee shops, and year-round festivals. Brooksville's unique rolling hills, oak-lined streets, and small-town charm

$199,999

2 beds1 bath785 sq ft

21397 Canal Dr, Brooksville, FL 34601

Access to i-75 • Access to us-41 • No hoa fees

ABOUT THIS HOME
Vintage Home for sale in Hernando County, FL:
2 Bedroom home on a corner lot. This property has 4 Lots included. Lots 51 52 53 54, totaling . 40 acres of land- Lots 53 & 54 are behind the home on Union St. Close to dining and the quaint Downtown Brooksville. The front porch greets you before entering the home. There is a cozy living room and also an additional room that can be used as a dining room. Eating space in the kitchen area. Laminate flooring throughout, Great fenced in backyard for privacy. Call Today For A Showing.

$99,899

2 beds1 bath656 sq ft

521 Smith & Union ST Lots 53 & 54, Brooksville, FL 34601

Fenced in backyard • 4 lots included • 40 acres of land

ABOUT THIS HOME
Vintage Home for sale in Hernando County, FL:
INVESTOR SPECIAL / MAJOR REHAB OPPORTUNITY! Bring your vision to this Brooksville property situated on a spacious lot with beautiful mature trees. This property offers significant potential for an investor, contractor, or experienced renovator looking for their next project. The home is in need of extensive renovation and is being sold in its current AS-IS condition. Substantial repairs and improvements are needed throughout. Buyer and buyer's agent are responsible for independently verifying property condition, measurements, permitted use, zoning, and all information deemed important to the purchase.

$99,900

4 beds2 baths1,724 sq ft

822 Live Oak Dr, Brooksville, FL 34601

0.5 acre lot • Built 1958 • Listed 25 days

Property at 255 Benes Rd, Brooksville, FL 34604, 4 beds, 2.5 baths

$965,000

4 beds2.5 baths2,971 sq ft

255 Benes Rd, Brooksville, FL 34604

Property at 117 S Brooksville Ave, Brooksville, FL 34601, 4 beds, 2 baths

$325,000

4 beds2 baths2,758 sq ft

117 S Brooksville Ave, Brooksville, FL 34601

Property at 380 Moale Rd, Brooksville, FL 34604, 3 beds, 1 bath

$799,900

3 beds1 bath1,385 sq ft

380 Moale Rd, Brooksville, FL 34604

Property at 310 Longwood Dr, Brooksville, FL 34601, 3 beds, 2 baths

$250,000

3 beds2 baths1,306 sq ft

310 Longwood Dr, Brooksville, FL 34601

Property at 16170 Hurban St, Brooksville, FL 34604, 2 beds, 1 bath

$175,000

2 beds1 bath762 sq ft

16170 Hurban St, Brooksville, FL 34604

Property at 5364 Cyril Dr, Dade City, FL 33523, 2 beds, 1 bath

$149,900

2 beds1 bath400 sq ft

5364 Cyril Dr, Dade City, FL 33523

Property at 34746 Gardenia Way, Dade City, FL 33523, 3 beds, 3 baths

$300,000

3 beds3 baths1,835 sq ft

34746 Gardenia Way, Dade City, FL 33523

Property at 236 Pryor St, Brooksville, FL 34601, 3 beds, 2 baths

$265,000

3 beds2 baths1,233 sq ft

236 Pryor St, Brooksville, FL 34601

Property at 453 Bell Ave, Brooksville, FL 34601, 4 beds, 2.5 baths

$380,000

4 beds2.5 baths1,968 sq ft

453 Bell Ave, Brooksville, FL 34601

Property at 515 Stafford Ave, Brooksville, FL 34601, 4 beds, 2 baths

$299,900

4 beds2 baths2,374 sq ft

515 Stafford Ave, Brooksville, FL 34601

Property at 65 Olive St, Brooksville, FL 34601, 3 beds, 3 baths

$599,000

3 beds3 baths1,961 sq ft

65 Olive St, Brooksville, FL 34601

Property at 19199 Fort Dade Ave, Brooksville, FL 34601, 1 bed, 1 bath

$209,000

1 bed1 bath816 sq ft

19199 Fort Dade Ave, Brooksville, FL 34601

Property at 6462 Sealawn Dr, Spring Hill, FL 34606, 2 beds, 1 bath

$198,000

2 beds1 bath907 sq ft

6462 Sealawn Dr, Spring Hill, FL 34606

Property at 3037 Sunset Vista Dr, Spring Hill, FL 34607, 3 beds, 2 baths

$220,000

3 beds2 baths2,137 sq ft

3037 Sunset Vista Dr, Spring Hill, FL 34607

Property at 1019 S Mildred Ave, Brooksville, FL 34601, 3 beds, 2.5 baths

$485,000

3 beds2.5 baths2,707 sq ft

1019 S Mildred Ave, Brooksville, FL 34601

Property at 9499 Treiman Blvd, Webster, FL 33597, 3 beds, 1 bath

$539,000

3 beds1 bath1,782 sq ft

9499 Treiman Blvd, Webster, FL 33597

Property at 5473 Darlene St, Weeki Wachee, FL 34607, 2 beds, 1 bath

$449,000

2 beds1 bath995 sq ft

5473 Darlene St, Weeki Wachee, FL 34607

Property at 19222 Fort Dade Ave, Brooksville, FL 34601, 7 beds, 3 baths

$299,400

7 beds3 baths1,762 sq ft

19222 Fort Dade Ave, Brooksville, FL 34601

Property at 15458 Snow Memorial Hwy, Brooksville, FL 34601, 10 beds, 4 baths

$950,000

10 beds4 baths3,456 sq ft

15458 Snow Memorial Hwy, Brooksville, FL 34601

Property at 11317 Salina St, Brooksville, FL 34614, 1 bed, 1 bath

$354,000

1 bed1 bath780 sq ft

11317 Salina St, Brooksville, FL 34614

Property at 16119 Wilson Blvd, Brooksville, FL 34604, 3 beds, 2 baths

$325,000

3 beds2 baths1,776 sq ft

16119 Wilson Blvd, Brooksville, FL 34604

Property at 34798 Evergreen Way, Dade City, FL 33523, 3 beds, 1.5 baths

$289,900

3 beds1.5 baths1,330 sq ft

34798 Evergreen Way, Dade City, FL 33523

Property at 3044 Sunset Vista Dr, Spring Hill, FL 34607, 2 beds, 2 baths

$390,000

2 beds2 baths986 sq ft

3044 Sunset Vista Dr, Spring Hill, FL 34607

Property at 34796 Gardenia Way, Dade City, FL 33523, 3 beds, 1 bath

$248,900

3 beds1 bath1,521 sq ft

34796 Gardenia Way, Dade City, FL 33523

Property at 1524 Indian Bay Rd, Spring Hill, FL 34607, 2 beds, 1.5 baths

$725,000

2 beds1.5 baths1,348 sq ft

1524 Indian Bay Rd, Spring Hill, FL 34607

Property at 13499 Old Crystal River Rd, Brooksville, FL 34601, 2 beds, 2 baths

$824,900

2 beds2 baths967 sq ft

13499 Old Crystal River Rd, Brooksville, FL 34601

Property at 29373 Cortez Blvd, Brooksville, FL 34602, 2 beds, 1 bath

$999,999

Land9.74 acres (lot)

29373 Cortez Blvd, Brooksville, FL 34602

Property at LOT 1 Nightingale Rd, Brooksville, FL 34613, 2 beds, 2 baths

$55,000

Land0.46 acre (lot)

LOT 1 Nightingale Rd, Brooksville, FL 34613

Property at 17476 Nicholas Ave, Brooksville, FL 34604, 2 beds, 1 bath

$252,900

Land1.47 acres (lot)

17476 Nicholas Ave, Brooksville, FL 34604

Property at 7419 Buck Hope Rd, Brooksville, FL 34601, 1 bath

$145,000

Land0.66 acre (lot)

7419 Buck Hope Rd, Brooksville, FL 34601

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Based on information submitted to the MLS GRID as of Wed Oct 14 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Hernando County

There are currently 35 vintage homes for sale in Hernando County at a median listing price of $350K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Hernando County stay on the market for 89 days and receive 3 offers. This map is refreshed with the newest listings in Hernando County every 15 minutes.

In the past month, 329 homes have been sold in Hernando County. In addition to houses in Hernando County, there were also 21 condos, 5 townhouses, and 6 multi-family units for sale in Hernando County last month. Find your dream home in Hernando County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Hernando County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Hernando County. If you're looking to sell your home in the Hernando County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Hernando County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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