Middleton Homes with Cottage Style

Welcome to Middleton, a charming subdivision nestled in the heart of St. Augustine, Florida. This picturesque community is a hidden gem in St. Johns County, where the rich history of the area blends seamlessly with modern comforts and stunning natural landscapes. Middleton is renowned for its enchanting cottage-style homes, which evoke a sense of warmth and nostalgia, making it the perfect place for families, retirees, and everyone in between.

As you stroll through the tree-lined streets of Middleton, you'll be captivated by the whimsical architecture and vibrant gardens that adorn each property. These cottage-style homes feature charming details such as gabled roofs, inviting porches, and cozy nooks, creating an atmosphere that feels like a storybook come to life. Inside, you'll find open floor plans, modern amenities, and a design that emphasizes both comfort and functionality, allowing you to create lasting memories with family and friends.

Living in Middleton means embracing a lifestyle rich in community and convenience. Residents enjoy easy access to nearby parks, scenic trails, and the stunning beaches of St. Augustine, where the Atlantic Ocean beckons with its sun-soaked shores. The historic downtown area is just a short drive away, offering delightful shops, restaurants, and cultural attractions that celebrate the unique heritage of this timeless city.

Whether you're seeking a peaceful retreat or a vibrant community, Middleton offers the best of both worlds. Discover your dream cottage-style home in this enchanting subdivision and start making memories in one of Florida's most beloved locales!

Newest Middleton Homes with Cottage Style

$589,900

2 Beds ⋅ 2 Baths ⋅ 2160270 MLS

LOCATION! Beautiful Crescent Beach, known for surfing, fishing, boating, kayaking, and its laid-back coastal lifestyle. This charming vintage cottage was extensively renovated in 2017 and features vaulted ceilings with exposed beams, a cozy sunroom, custom cabinetry, granite countertops, and black stainless-steel appliances. No HOA! Sold AS-IS and fully furnished with recently updated furniture. Currently operated as an active, successful short-term rental--a great investment opportunity for someone looking for a turnkey, ready-to-go Airbnb business, vacation home, or primary residence.

6880 Middleton Avenue, St. Augustine

$749,900

3 Beds ⋅ 3 Baths ⋅ 2159963 MLS

ADORABLE 3BR/2.5BA BEACH HOME FEATURING SALTWATER POOL, NO HOA & AN UNBEATABLE LOCATION JUST 2 BLOCKS FROM CRESCENT BEACH! Built in 2018, this is a perfect full time home, beach getaway or investment property. Meticulous, turnkey home where nightly rentals are allowed. Offered furnished or unfurnished. Spacious owner suite on 1st floor. Large roomy kitchen has lots of cabinets, granite counter space & stainless steel appliances. Spacious living & dining rooms. Separate laundry room leads to garage. Upstairs includes 2 bedrooms, 1 bathroom & an 11x13 family room! Fully fenced paved patio around heated pool & low maintenance yard. Wash your sandy toes in the outdoor shower. CONCRETE BOARD SIDING & HIGH ELEVATION OF HOME KEEPS INSURANCE COSTS LOW! Flood insurance is only $1400 and is transferable! Bring your boat! Green Rd Boat Ramp only 1/2 mile south. 2 blocks to Historic Genungs Fish Camp on the ICW. Less than 15 min to shopping, Amphtiheater & historic downtown St Augustine.

6832 Middleton Avenue, St. Augustine

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The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Northeast Florida Multiple Listing Service, Inc. Real estate listings held by brokerage firms other than Realty Exchange LLC are marked with the listing broker’s name and detailed information about such listings includes the name of the listing brokers. Data provided is deemed reliable but is not guaranteed. © 2026 Northeast Florida Multiple Listing Service, Inc. All rights reserved. Data last updated