Dunedin Homes With a Guest House For Sale

This page features homes for sale in Dunedin with a guest house. If you are interested in the Dunedin real estate market, specifically properties that include a guest house, you will find all available listings below. These properties are highly sought after, offering flexible living solutions for multi-generational families or potential rental income opportunities. To learn more about a specific property, click on the listing to view detailed information. Our Dunedin real estate team can also provide prospective buyers with disclosures, past sales history, and prices of recently sold homes with guest houses in the area.

Even if you are just beginning your home search, we encourage you to register for a free account. An active account allows you to utilize our advanced search features, share listings with friends and family, and receive email alerts as soon as new Dunedin homes with a guest house become available. This ensures you stay informed and ahead of other potential buyers in the market.

Search Dunedin Homes with a Guest House

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$6,603,000

↓ $347,000

147 & 139 Edgewater Drive, DUNEDIN

6 Beds 6 Baths 9,978 SqFt Residential MLS® # TB8374458

$2,390,000

2133 Harbor View Drive, DUNEDIN

5 Beds 4 Baths 2,878 SqFt Residential MLS® # TB8425448

Pending

$1,970,000

20 Outlook Way 10, DUNEDIN

3 Beds 3 Baths 2,163 SqFt Residential MLS® # TB8388228

$1,950,000

43 Edgewater Drive, DUNEDIN

4 Beds 3 Baths 3,677 SqFt Residential MLS® # TB8395344

$1,790,000

225 President Street, DUNEDIN

3 Beds 3 Baths 2,243 SqFt Residential MLS® # TB8428221

Openhouse

$1,774,000

↓ $21,000

400 Broadway, DUNEDIN

3 Beds 4 Baths 2,677 SqFt Residential MLS® # TB8422521

$1,690,000

16 Outlook Way 9, DUNEDIN

3 Beds 3 Baths 2,091 SqFt Residential MLS® # TB8408730

Openhouse

$1,675,000

↓ $20,999

429 Scotland Street, DUNEDIN

4 Beds 3 Baths 2,160 SqFt Residential MLS® # TB8430849

$1,585,000

1956 Cedar Drive, DUNEDIN

3 Beds 3 Baths 2,436 SqFt Residential MLS® # TB8450485

Pending

$1,500,000

1454 Aberdeen Oaks Drive, DUNEDIN

4 Beds 6 Baths 3,624 SqFt Residential MLS® # TB8450615

$1,375,000

20 Outlook Way 7, DUNEDIN

3 Beds 3 Baths 2,065 SqFt Residential MLS® # TB8381028

Pending

$1,350,000

↓ $150,000

2035 Indian Creek Court, DUNEDIN

4 Beds 4 Baths 3,429 SqFt Residential MLS® # TB8441140

Pending

$1,345,000

35 Concord Drive, DUNEDIN

4 Beds 3 Baths 2,618 SqFt Residential MLS® # TB8433289

Pending

$1,250,000

606 New York Avenue, DUNEDIN

4 Beds 2 Baths 2,850 SqFt Residential MLS® # TB8443597

$1,250,000

1340 Bayshore Boulevard 304, DUNEDIN

3 Beds 3 Baths 2,706 SqFt Residential MLS® # TB8437458

$1,175,000

↓ $25,000

2012 Culberson Avenue, DUNEDIN

4 Beds 2 Baths 2,432 SqFt Residential MLS® # TB8440588

$1,100,000

2127 Lagoon Drive, DUNEDIN

3 Beds 2 Baths 2,416 SqFt Residential MLS® # TB8402530

$990,000

↓ $35,000

2279 Ranchette Lane, DUNEDIN

4 Beds 3 Baths 3,169 SqFt Residential MLS® # TB8386283

Pending

$960,000

515 Douglas Place, DUNEDIN

4 Beds 4 Baths 2,415 SqFt Residential MLS® # TB8438415

Pending

$925,000

2251 Highwood Court, DUNEDIN

4 Beds 3 Baths 2,736 SqFt Residential MLS® # TB8440051

Pending

$875,000

2298 Hannah Way N, DUNEDIN

5 Beds 3 Baths 3,510 SqFt Residential MLS® # TB8419816

Pending

$849,000

↓ $20,000

1180 Nelson Street, DUNEDIN

4 Beds 3 Baths 2,029 SqFt Residential MLS® # TB8412090

Pending

$847,000

1955 Dunloe Circle, DUNEDIN

3 Beds 3 Baths 2,332 SqFt Residential MLS® # TB8444714

$820,000

↓ $5,000

2353 Demaret Drive, DUNEDIN

4 Beds 3 Baths 1,934 SqFt Residential MLS® # TB8436831

$815,000

↓ $15,000

2654 Crystal Circle, DUNEDIN

3 Beds 3 Baths 2,314 SqFt Residential MLS® # O6358555

Pending

$800,000

↓ $99,900

642 Weathersfield Drive, DUNEDIN

4 Beds 4 Baths 3,648 SqFt Residential MLS® # TB8438649

$780,000

↓ $19,900

58 Arnoni Drive, DUNEDIN

4 Beds 3 Baths 2,323 SqFt Residential MLS® # TB8419814

$775,000

1245 Curlew Road, DUNEDIN

4 Beds 3 Baths 2,619 SqFt Residential MLS® # TB8450486

$759,000

↓ $30,000

214 Scotland St, DUNEDIN

2 Beds 2 Baths 1,248 SqFt Residential MLS® # TB8390202

$729,000

↓ $10,000

433 S Paula Drive 31, DUNEDIN

3 Beds 3 Baths 1,755 SqFt Residential MLS® # TB8394654

$725,000

2363 Hanover Drive, DUNEDIN

3 Beds 2 Baths 2,166 SqFt Residential MLS® # TB8446550

Pending

$649,900

1561 Mac Charles Court, DUNEDIN

4 Beds 3 Baths 2,678 SqFt Residential MLS® # O6356406

Pending

$649,000

219 Park Circle S, DUNEDIN

2 Beds 2 Baths 1,961 SqFt Residential MLS® # TB8377537

$639,000

↓ $10,000

554 Louden Avenue, DUNEDIN

2 Beds 2 Baths 1,806 SqFt Residential MLS® # TB8416064

$639,000

↓ $5,500

1290 Michigan Boulevard, DUNEDIN

4 Beds 3 Baths 1,869 SqFt Residential MLS® # TB8389154

Pending

$625,000

2275 Twin Lane Drive, DUNEDIN

3 Beds 3 Baths 2,425 SqFt Residential MLS® # TB8437755

$589,000

↓ $10,000

2056 Bellhurst Drive, DUNEDIN

3 Beds 2 Baths 1,725 SqFt Residential MLS® # TB8443486

$575,000

1787 Santa Barbara Drive, DUNEDIN

3 Beds 2 Baths 1,485 SqFt Residential MLS® # TB8448989

$575,000

↓ $14,000

1559 Roxburg Lane, DUNEDIN

3 Beds 2 Baths 1,813 SqFt Residential MLS® # TB8452251

$569,900

↓ $25,100

2237 Spanish Vistas Drive, DUNEDIN

3 Beds 2 Baths 1,399 SqFt Residential MLS® # TB8434704

Openhouse

$562,000

2700 Bayshore Boulevard 11405, DUNEDIN

2 Beds 2 Baths 1,245 SqFt Residential MLS® # TB8408165

New Listing

$540,000

711 San Salvador Drive, DUNEDIN

3 Beds 2 Baths 1,622 SqFt Residential MLS® # TB8454321

Pending

$499,900

↓ $20,000

787 San Salvador Drive, DUNEDIN

4 Beds 3 Baths 2,065 SqFt Residential MLS® # TB8407009

$495,000

↓ $4,000

2480 Del Rio Way, DUNEDIN

3 Beds 2 Baths 1,479 SqFt Residential MLS® # TB8420150

$494,900

1393 Chesterfield Drive, DUNEDIN

3 Beds 2 Baths 1,296 SqFt Residential MLS® # TB8435868

$485,900

↑ $1,000

2700 Bayshore Boulevard 11308, DUNEDIN

2 Beds 2 Baths 1,185 SqFt Residential MLS® # TB8390076

Pending

$475,000

501 Louden Avenue, DUNEDIN

3 Beds 2 Baths 1,358 SqFt Residential MLS® # TB8440239

$470,000

3292 Covered Bridge Drive E, DUNEDIN

3 Beds 3 Baths 2,027 SqFt Residential MLS® # TB8378905

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Buying a Dunedin Home With a Guest House 

Buying a home in Dunedin, FL, with a guest house offers a unique opportunity to enjoy the charm of this coastal town while benefiting from added space and versatility. Dunedin, known for its vibrant downtown, stunning waterfront views, and small-town feel, is a highly desirable location for homebuyers. Its proximity to the Gulf of Mexico, Honeymoon Island State Park, and the Pinellas Trail makes it a haven for outdoor enthusiasts and those seeking a relaxed lifestyle.

Homes with guest houses in Dunedin are particularly in demand due to their flexibility. A guest house can serve as a private retreat for visiting family and friends, a home office, or even a rental property to generate additional income. With Dunedin’s thriving tourism scene and events like the Dunedin Highland Games and Art Festivals, short-term rental opportunities are especially appealing.

The town’s historic charm, with its tree-lined streets and bungalow-style homes, adds to the allure of properties with guest houses. Many of these homes are located near the walkable downtown area, which is filled with boutique shops, local breweries, and waterfront dining options. The sense of community in Dunedin is strong, with frequent events and a welcoming atmosphere that attracts families, retirees, and professionals alike.

For those seeking a blend of coastal living, investment potential, and a vibrant community, buying a home in Dunedin with a guest house is an excellent choice. It’s a lifestyle upgrade that offers both comfort and opportunity in one of Florida’s most charming towns.

Continue Searching Homes with a Guest House in Florida 

Not seeing the right home with a guest house that fits your needs, wants, or budget here? Continue searching homes for sale with a guest house for sale in other Florida cities and towns using our homes with a guest house-by-city directory below.