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Rolling Hills Homes for Sale

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  • /26

    $305,000

    • 3 Beds
    • 2.5 Baths
    • 1,484 Sq Ft

    54 Ridge Lake Rd, Saint Augustine, FL 32086

    Reside in Park Ridge and discover the St. Augustine lifestyle, where coastal charm and historic character meet modern living. This 3-bedroom, 2.5-bath townhome places you minutes from the city's vibrant downtown, filled with cobblestone streets, unique shops, and award-winning dining. Spend weekends on the sandy shores of St. Augustine Beach, catch live music at the St. Augustine Amphitheatre, or

    Agent Photo

    TERRI APODACA

    DAVIDSON REALTY, INC.

    (855) 612-6172

    54 Ridge Lake Rd, Saint Augustine, FL 32086
  • /40

    $355,000

    • 3 Beds
    • 2 Baths
    • 1,335 Sq Ft

    421 Chamberlain Dr, Saint Augustine, FL 32086

    Welcome to 421 Chamberlain Drive — a beautifully maintained 3 bedroom, 2 bathroom home in the heart of St. Augustine, offering comfort, convenience, and peace of mind. Ideally located just minutes from top-rated schools, Flagler Hospital, and St. Augustine University, it’s a perfect fit for medical and education professionals, students, or anyone who wants quick access to everyday essentials.

    Paul Wenglowsky Keller Williams Realty Atlantic Partners St Augustine

    421 Chamberlain Dr, Saint Augustine, FL 32086
  • /18

    $240,000 Pre-Foreclosure

    • 2 Beds
    • 2.5 Baths
    • 1,211 Sq Ft

    62 Buckley Ct, Saint Augustine, FL 32086

    Welcome to this charming 2 bed 2 bath townhome in beautiful Saint Augustine. This light and bright home offers an open living area, spacious bedrooms, and a functional kitchen with plenty of storage. Enjoy peaceful mornings on your private patio or take advantage of the community amenities. Located just minutes from shopping dining and everyday conveniences along US 1 and only a short drive to

    Josiah Tripp NEXTHOME COAST2COAST

    62 Buckley Ct, Saint Augustine, FL 32086
  • /4

    $225,000

    • Land
    • 0.75 Acre
    • $300,000 per Acre

    0 Dobbs Rd Unit 255110, Saint Augustine, FL 32086

    Prime industrial-zoned land opportunity located on Dobbs Road with convenient access to both State Road 207 and State Road 312 W. This site offers excellent visibility and connectivity, making it ideal for industrial development, distribution, or flex use. Positioned in a growing commercial corridor, the property provides strong logistical advantages for businesses seeking a central location with

    Eric Maimo Coldwell Banker Commercial Premier Properties

    0 Dobbs Rd Unit 255110, Saint Augustine, FL 32086
  • /7

    $225,000

    • Land
    • 1.23 Acres
    • $182,927 per Acre

    00 Kings Estate Rd, Saint Augustine, FL 32086

    Vacant Lot in St. Augustine – Close to the Historic District! An opportunity to build your dream home on this vacant lot located just moments away from St. Augustine's historic district. This lot offers a perfect blend of serene living and vibrant city life, making it an ideal spot for your future home. Situated in the heart of St. Augustine, this lot is just a short drive from the historic

    howard hughes Coastal Realty Pros LLC

    00 Kings Estate Rd, Saint Augustine, FL 32086
  • /39

    $387,500

    • 3 Beds
    • 2 Baths
    • 1,591 Sq Ft

    305 Green Turtle Ln, St. Augustine, FL 32086

    ** NEW PRICE!** Opportunity is knocking at this beautiful 3-bedroom home in the popular community of Deerfield Preserve, conveniently located and within a short drive to the historic downtown district, beaches, hospitals, restaurants, shopping and I-95. The kitchen is the heart of the home, which features a large island, granite counters and eat-in dining area. The spacious living room looks out

    K. Jennifer Cook Compass Florida

    305 Green Turtle Ln, St. Augustine, FL 32086
  • /21

    $185,000

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    405 S Villa San Marco Dr Unit 302, Saint Augustine, FL 32086

    Effortless living awaits in the sought-after Villa San Marco community! This beautifully maintained 2BR/2BA condo offers a bright open floor plan with split bedrooms for privacy, new flooring throughout, fresh paint, and tranquil preserve views from every window. The kitchen with island seating and breakfast nook flows seamlessly into the living area—perfect for entertaining. Enjoy peaceful

    Zachary Esposito ENDLESS SUMMER REALTY

    405 S Villa San Marco Dr Unit 302, Saint Augustine, FL 32086
  • /51

    $449,000

    • 4 Beds
    • 2 Baths
    • 2,067 Sq Ft

    228 Fox Water Trail, St. Augustine, FL 32086

    Live the St. Augustine lifestyle in this beautifully upgraded 4BR/2BA home! Step inside to a bright, open layout featuring durable tile flooring, granite countertops, stainless steel appliances (just over a year old), and modern matching light fixtures throughout. The spacious primary suite offers a large walk-in closet, and the home includes a NEW HVAC system for year-round comfort. Enjoy major

    Anh Hoang Keller Williams Realty Atlantic Partners St Augustine

    228 Fox Water Trail, St. Augustine, FL 32086
  • /34

    $230,000

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    410 S Villa San Marco Dr Unit 303, Saint Augustine, FL 32086

    Spacious 2 bedroom/2 bath split bedroom floor plan. The unit has a screened in balcony. New A/C 2025, wood flooring, bathrooms, kitchen. Community amenities include a clubhouse with pool and fitness center. Location is ideal being close to I-95, colleges, stores, restaurants, historic St. Augustine and minutes to the beach.

    Luis Cancel GLOBAL BROKERS RLTY OF FLORIDA

    410 S Villa San Marco Dr Unit 303, Saint Augustine, FL 32086
  • /25

    $399,900

    • 4 Beds
    • 3 Baths
    • 1,925 Sq Ft

    709 Deer Crossing Rd, Saint Augustine, FL 32086

    Here's your golden ticket to snag a gem in the sought-after Deerfield Preserve! This charming abode boasts 4 bedrooms, with not one, but TWO master suites! Nestled in a lively gas community, you'll enjoy a fabulous amenity center complete with a gym, pool, playground, and soccer field, all encircled by a delightful walking trail. Carpet-phobes rejoice—this home features stylish tile and LPV

    Lorraine Manna Exp Realty

    709 Deer Crossing Rd, Saint Augustine, FL 32086
  • /18

    $199,990

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    420 S Villa San Marco Dr Unit 304, Saint Augustine, FL 32086

    A $5,000 concession with an acceptable offer toward buyer's closing cost. This BELOW MARKET VALUE spacious super clean 2-bedroom 2-bath has a good size balcony that backs to a peaceful wooded preserve. That this condo sits in the high A rated school districts, is but one of its many benefits of living in this great community. Not to mention its resort-like amenities that include a lush,

    Ray Feliciano FLORIDA HOMES REALTY & MTG LLC

    420 S Villa San Marco Dr Unit 304, Saint Augustine, FL 32086
  • /32

    $219,000

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    410 S Villa San Marco Dr Unit 106, Saint Augustine, FL 32086

    GROUND FLOOR WITH GARAGE! Find your peaceful spot with beautiful lake views in this well-kept ground-floor 2-bedroom, 2-bath condo at Villa San Marco — complete with a private garage! The open layout with a smart split floor plan gives you plenty of space to relax or entertain. You'll love the private enclosed balcony — perfect for morning coffee or unwinding with friends. Low HOA fees cover

    Trudy Padilla KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE

    410 S Villa San Marco Dr Unit 106, Saint Augustine, FL 32086
  • /35

    $199,900

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    415 S Villa San Marco Dr Unit 205, Saint Augustine, FL 32086

    **Motivated Seller**Location, Location! This efficient 2 bedroom 2 bath unit shows that it has been well maintained and the highly-desirable Villa San Marco community is a wonderful and meticulously-maintained community as well! Enjoy all the conveniences of resort style living with a clubhouse, pool and gym. Its central location is just minutes to our historic downtown as well as the sugar sand

    Gloria Worley Century 21 St Augustine Properties

    415 S Villa San Marco Dr Unit 205, Saint Augustine, FL 32086
  • /26

    $279,500

    • 3 Beds
    • 2.5 Baths
    • 1,499 Sq Ft

    22 Buckley Ct, Saint Augustine, FL 32086

    Beautiful Townhome located in Cypress Bay, 3 bedroom 2.5 bath end unit with attached Garage. New Paint and Newer Flooring throughout! Large open kitchen with stainless appliances and spacious living area. Washer and dryer included! Move in Ready!

    Tari Taylor Premier Homes Realty, Inc.

    22 Buckley Ct, Saint Augustine, FL 32086
  • /49

    $334,900

    • 3 Beds
    • 2.5 Baths
    • 1,505 Sq Ft

    74 Ridge Lake Rd, St. Augustine, FL 32086

    This elegant 3-bedroom, 2.5-bath townhome is a remarkable find surpassing new construction with its thoughtful upgrades and pristine condition. Built in 2022, this end unit features an open floor plan complemented by 9-foot ceilings and oversized front and rear doors that enhance the living space and provides natural lighting. Kitchen boasts a large island with quartz countertops, gray shaker

    Nancy DeLellis Keller Williams Realty Atlantic Partners St Augustine

    74 Ridge Lake Rd, St. Augustine, FL 32086
  • /29

    $199,000

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    410 S Villa San Marco Dr Unit 203, Saint Augustine, FL 32086

    Find your peaceful spot in this well-kept 2-bedroom, 2-bath condo at Villa San Marco. The open layout with a smart split floor plan gives you plenty of space to relax or entertain. You'll love the private enclosed balcony — perfect for morning coffee or unwinding with friends. Low HOA fees cover water, sewer, and garbage, so you can focus on what matters most. Plus, you're just minutes from

    Trudy Padilla KELLER WILLIAMS REALTY ATLANTIC PARTNERS ST. AUGUSTINE

    410 S Villa San Marco Dr Unit 203, Saint Augustine, FL 32086
  • /27

    $255,000

    • 2 Beds
    • 2.5 Baths
    • 1,341 Sq Ft

    253 Whitland Way, Saint Augustine, FL 32086

    Welcome to 253 Whitland Way, a modern 2-bed, 2.5-bath townhome built in 2018, offering 1,346 sq ft of stylish, low-maintenance living in the desirable Cypress Bay community. This home backs to a natural preserve, providing rare privacy and peaceful views that set it apart from others. Inside, you'll find an open floor plan with contemporary finishes, a spacious kitchen with breakfast bar, in-unit

    Ryan Raymond PA JASON MITCHELL REAL ESTATE FLORIDA, LLC.

    253 Whitland Way, Saint Augustine, FL 32086
  • /4

    $225,000

    • Land
    • 0.75 Acre
    • $300,000 per Acre

    0 Dobbs Rd Unit MFRGC533824, Saint Augustine, FL 32086

    Prime industrial-zoned land opportunity located on Dobbs Road with convenient access to both State Road 207 and State Road 312 W. This site offers excellent visibility and connectivity, making it ideal for industrial development, distribution, or flex use. Positioned in a growing commercial corridor, the property provides strong logistical advantages for businesses seeking a central location with

    Eric Maimo COLDWELL BANKER COMMERCIAL PREMIER PROPERTIES

    0 Dobbs Rd Unit MFRGC533824, Saint Augustine, FL 32086
  • /57

    $399,900

    • 4 Beds
    • 2 Baths
    • 1,916 Sq Ft

    38 Green Turtle Ln, St. Augustine, FL 32086

    Charming 4-Bedroom Home in Saint Augustine, FL with almost no electric bill due to paid off solar panels at closing that come with the home. This spacious 1,916 sq ft home offers 4 bedrooms and 2 bathrooms with newer roof and HVAC, providing ample space for comfortable living. This home features an open concept living area. The expansive floor plan seamlessly connects the living, dining, and

    Shane Radcliff REALTY EXCHANGE OF FLORIDA

    38 Green Turtle Ln, St. Augustine, FL 32086
  • /54

    $389,000

    • 3 Beds
    • 2 Baths
    • 1,709 Sq Ft

    509 Deer Crossing Rd, St. Augustine, FL 32086

    Welcome to your perfect Florida lifestyle! This charming 3-bedroom 2-bathroom home is nestled in a sought-after residential community featuring a sparkling pool, inviting clubhouse, and fully equipped gym. Whether you’re raising a family or enjoying retirement, you’ll love this peaceful neighborhood feel with resort-style amenities right at your doorstep. Just minutes from vibrant downtown

    Sommer Warring Florida Homes Realty & Mortgage

    509 Deer Crossing Rd, St. Augustine, FL 32086
  • /12

    $199,990

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    420 S Villa San Marco Dr, Saint Augustine, FL 32086

    A $5,000 concession with an acceptable offer toward buyer's closing cost. This BELOW MARKET VALUE spacious super clean 2-bedroom 2-bath has a good size balcony that backs to a peaceful wooded preserve. That this condo sits in the high A rated school districts, is but one of its many benefits of living in this great community. Not to mention its resort-like amenities that include a lush,

    Ray Feliciano Florida Homes Realty & Mortgage

    420 S Villa San Marco Dr, Saint Augustine, FL 32086
  • /33

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft

    405 S Villa San Marco Dr Unit 208, Saint Augustine, FL 32086

    This spacious 3 bedroom, 2 bath condominium has been a consistent, high-performing investment for nearly two years. While serving as a primary residence for the seller during college, it also generated $2,200 a month in rental income from the additional bedrooms, proving itself as both a comfortable home and a reliable income-producing asset. Conveniently located just 5 minutes from the

    Courtney McQuaig MAXREV, LLC

    405 S Villa San Marco Dr Unit 208, Saint Augustine, FL 32086
  • /36

    $359,000

    • 4 Beds
    • 2 Baths
    • 2,239 Sq Ft

    425 S Hidden Tree Dr, Saint Augustine, FL 32086

    Discover exceptional value in The Hideaway at Old Moultrie with this spacious 4-bedroom home offering an open, airy floor plan, 10-foot ceilings and fully tiled flooring. Enjoy a large living area that flows seamlessly into a well-appointed kitchen featuring maple cabinetry, stainless steel appliances, and an island with generous prep space. The oversized primary suite includes a tray ceiling,

    Jason Neely Landmark Realty Inc

    425 S Hidden Tree Dr, Saint Augustine, FL 32086
  • /53

    $329,500

    • 3 Beds
    • 2.5 Baths
    • 1,470 Sq Ft

    22 Ridge Lake Rd, Saint Augustine, FL 32086

    Modern Townhome in Prime St. Augustine Location | 3 Bed, 2.5 Bath | Built in 2022 | Motivated Seller – Concessions Available! Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome in the sought-after Park Ridge community, just 10 minutes from historic downtown St. Augustine! Built in 2022, this home combines stylish modern finishes with energy efficiency and low-maintenance living.

    John Sansaricq SANCASTLE REALTY LLC

    22 Ridge Lake Rd, Saint Augustine, FL 32086
  • /15

    $197,000

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft

    425 S Villa San Marco Dr Unit 301, Saint Augustine, FL 32086

    This very well maintained condo is in the sought after Villa San Marco Community. Owner occupied for the last 5 years. Split open floor plan. Newer appliances. Master bedroom has a walk in closet. Stackable washer/dryer, screened in porch with a good view, custom blinds and a reverse osmosis drinking water system in kitchen. Recently replaced toilets and sinks in both bathrooms. Plank flooring

    Mark Kempler Crescent Beach Realty of St Augustine

    425 S Villa San Marco Dr Unit 301, Saint Augustine, FL 32086
  • /30

    $549,000

    • 3 Beds
    • 2 Baths
    • 1,505 Sq Ft

    725 Cypress Rd, Saint Augustine, FL 32086

    Rare opportunity in St. Augustine Beach! Enjoy over 1.5 acres of partially cleared, lushly landscaped land with no HOA, a true find this close to the coast. Tucked away on a quiet street with only 10 homes, this property offers privacy, space, and endless potential. Property highlights are this 3 Bedrooms, 2 Bathrooms, 1,500+ sq ft home. Two 12x30 ft sheds with electricity — ideal for a workshop,

    Marian Schneider RE/MAX Prime Properties

    725 Cypress Rd, Saint Augustine, FL 32086

Why Live in Rolling Hills

Rolling Hills in Saint Augustine is a neighborhood featuring modern homes built primarily in the 2000s and 2010s, with new constructions still available. The community is characterized by wide, well-kept sidewalks lined with palm trees and subdivisions like Deerfield Preserve that offer waterfront views. While the proximity to state Road 207 can result in some highway noise, the area is safer than the national average. Residents have access to various parks, including Vaill Point Park and Trail, known for its birdwatching opportunities, and Treaty Park, which offers softball fields, bocce ball courts, and a skate park. Stone Climbing provides rock climbing classes, and the Doug Crane Boat Ramp allows for boating on the Matanzas River. For entertainment, Epic Theatres of Saint Augustine screens both new and classic films. Dining options include Saint Augustine Fish House & Oyster Company and Ned’s Southside Kitchen, with shopping available at Cobblestone Village and upscale stores at Saint Augustine Premium Outlets, 11 miles away. The neighborhood is well-connected, with state Road 207 and U.S. Route 1 providing easy travel, and downtown Saint Augustine just four miles away. Schools in the area are highly rated, with Osceola Elementary School, R.J. Murray Middle School, and Saint Joseph Academy all receiving high marks. The Sunshine Bus Company offers convenient transportation for older residents.

Frequently Asked Questions

Is Rolling Hills a good place to live?
Rolling Hills is a good place to live. Rolling Hills is considered very car-dependent and somewhat bikeable. Rolling Hills is a neighborhood with a crime score of 4, on par with the average neighborhood in the U.S. Rolling Hills has 6 parks for recreational activities. It is sparse in population with 2.6 people per acre and a median age of 42. The average household income is $72,603 which is below the national average. College graduates make up 29.9% of residents. A majority of residents in Rolling Hills are home owners, with 41.8% of residents renting and 58.2% of residents owning their home. A local real estate agent serving Rolling Hills can help you decide if this neighborhood is the right one for you. Learn more on our Rolling Hills neighborhood guide.
Is Rolling Hills, FL a safe neighborhood?
Rolling Hills, FL is a safe neighborhood and is on par with the average neighborhood in the United States. It received a crime score of 4 out of 10.
How much do you need to make to afford a house in Rolling Hills?
The median home price in Rolling Hills is $329,900. If you put a 20% down payment of $66,000 and had a 30-year fixed mortgage with an interest rate of 6.22%, your estimated principal and interest payment would be $1,620 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $69K a year to afford the median home price in Rolling Hills. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Rolling Hills is $73K.
What are the best public schools in Rolling Hills?
The best public schools that serve Rolling Hills are:
What are the best private schools in Rolling Hills?
The best private schools that serve Rolling Hills are:
What are the most popular zip codes in Rolling Hills, Saint Augustine, FL?
The most popular zip codes in Rolling Hills, Saint Augustine, FL include 32086, 32084, 32258, 32080 and 32095.
What are the most popular neighborhoods near Rolling Hills, Saint Augustine, FL?
The most popular neighborhoods near Rolling Hills, Saint Augustine, FL are West Augustine, Kings, Marketplace, Wildwood and Lincolnville.
Are home prices dropping in Rolling Hills?
Yes, home prices in Rolling Hills are down 11% in the last 12 months.

Home Trends in Rolling Hills, FL

Housing Trends

Median Sale Price
$329,000
Median Single Family Sale Price
$380,000
Median Townhouse Sale Price
$251,500
Median 2 Bedroom Sale Price
$199,900
Median 1 Bedroom Sale Price
$177,000
Average Price Per Sq Ft
$203
Number of Homes for Sale
23
Last 12 months Home Sales
58
Months of Supply
4.80
Median List Price
$329,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-5%
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