Community View
$1,589,000 | 35 Monterrey Drive, Smithtown, NY 11780 | 5 Bed, 4 Bath | Listing by Signature Premier Properties
Two-story residence with a gray shingle roof, light blue siding, and white trim
$1,699,000 | 38 Hamlet Woods Drive, Smithtown, NY 11780 | 4 Bed, 8 Bath | Listing by Maison Pawli LLC
Ranch-style house featuring a front lawn, asphalt driveway, an attached 2 car garage,
$1,025,000 | 39 Hamlet Woods Drive, Smithtown, NY 11780 | 3 Bed, 3 Bath | Listing by Douglas Elliman Real Estate
View of front of property with a balcony, french doors, a front yard, decorative driveway, and stone siding
$7,800 | 19 Hamlet Woods Drive, Smithtown, NY 11780 | 5 Bed, 5 Bath | Listing by Realty Connect USA L I Inc
Community View
$1,090,000 | 5 Hamlet Woods Drive, Smithtown, NY 11780 | 3 Bed, 3 Bath | Listing by Signature Premier Properties
View of front facade featuring a front lawn, aphalt driveway, a residential view, a garage, and stone siding
$1,495,000 | 22 Hamlet Woods Drive, Smithtown, NY 11780 | 3 Bed, 4 Bath | Listing by Douglas Elliman Real Estate
Single story home featuring stone siding, decorative driveway, a front yard, and fence
$1,490,000 | 52 Monterrey Drive, Smithtown, NY 11780 | 3 Bed, 3 Bath | Listing by Signature Premier Properties
View of front yard and a garage
$1,350,000 | 34 Hamlet Woods Drive, Smithtown, NY 11780 | 5 Bed, 5 Bath | Listing by Daniel Gale Sothebys Intl Rlty
Community View
$1,449,000 | 29 Monterrey Drive, Smithtown, NY 11780 | 5 Bed, 5 Bath | Listing by Signature Premier Properties
Living Room
$849,000 | 7 Country Woods Drive, Smithtown, NY 11780 | 3 Bed, 3 Bath | Listing by Douglas Elliman Real Estate
Community View
$1,080,000 | 49 Hamlet Woods Drive, Smithtown, NY 11780 | 4 Bed, 3 Bath | Listing by Prime Realty
Community View
$6,500 | 2 Pondview, Smithtown, NY 11780 | 4 Bed, 3 Bath | Listing by Patty Gallegos Rlty Intl Corp
Community View
$1,599,000 | 17 Monterrey Drive Unit 17, Smithtown, NY 11780 | 5 Bed, 7 Bath | Listing by Coldwell Banker American Homes
Community View
$1,475,000 | 12 Pondview, Smithtown, NY 11780 | 5 Bed, 5 Bath | Listing by Douglas Elliman Real Estate
Community View
$1,400,000 | 15 Monterrey Drive, Smithtown, NY 11780 | 5 Bed, 6 Bath | Listing by Netter Real Estate Inc
Community View
$879,000 | 31 Hamlet Woods Drive Unit 31, Smithtown, NY 11780 | 3 Bed, 3 Bath | Listing by Douglas Elliman Real Estate
Welcome Home!
$879,000 | 40 Monterrey Drive Unit 40, Smithtown, NY 11780 | 3 Bed, 3 Bath | Listing by Compass Greater NY LLC
Community View
$999,999 | 36 Hamlet Woods Drive, Smithtown, NY 11780 | 4 Bed, 3 Bath | Listing by BERKSHIRE HATHAWAY
Community View
$1,029,000 | 28 Hamlet Woods Drive, Smithtown, NY 11780 | 4 Bed, 4 Bath | Listing by Douglas Elliman Real Estate
Community View
$1,249,999 | 21 Monterrey Drive, Smithtown, NY 11780 | 4 Bed, 5 Bath | Listing by BERKSHIRE HATHAWAY

The Hamlet Estates Community

5 Hamlet Woods Dr, Saint James, NY 11780 | Suffolk, NY county

The Hamlet Estates at Saint James is a gated residential community offering an inviting blend of comfort, privacy, and resort-style living in one of Long Island’s most desirable North Shore locations. The neighborhood features a cohesive streetscape with private internal roadways, open green spaces, and scenic water features, including two lakes that add to the community’s tranquil atmosphere. Homes are set within a well-planned environment that balances natural beauty with modern infrastructure, creating a setting that feels established, private, and welcoming. Ideally located just minutes from shopping, dining, and major parkways, The Hamlet Estates at Saint James offers the convenience of easy access while maintaining a quiet, residential feel, making it an appealing choice for those seeking both relaxation and connectivity.

0.39 acres Average Lot Size
2 Active Listings
167 Total Housing Units
1,768 Average Square Footage

Resident Amenities

sports_basketball Basketball Court
family_group Clubhouse
fitness_center Fitness Center
award_star Gated Community
award_star Grounds & Common Area Maintenance
pool Pool
award_star Spa
sports_tennis Tennis Court
award_star Waterfront Access

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Resident Amenities

expand_less
sports_basketball Basketball Court
family_group Clubhouse
fitness_center Fitness Center
award_star Gated Community
award_star Grounds & Common Area Maintenance
pool Pool
award_star Spa
sports_tennis Tennis Court
award_star Waterfront Access

Active Listings & Homes For Sale and For Rent

Photo Lot Price Beds Baths Square Feet HOA Fees
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The Hamlet Estates Community (and nearby)
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The Hamlet Estates Residences

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Available Home Models

Addison

The Addison is a 3,500-square-foot, two-story home with four bedrooms, three and a half baths, and a three-car garage. Its main level centers on a spacious primary suite with a private bath featuring a separate shower and Jacuzzi tub. The open layout includes a gourmet kitchen, formal living and dining rooms, a library or office, and a den or great room with a fireplace. Upstairs are three bedrooms and a balcony loft. Hardwood floors, a full basement, and community pool and tennis access complete the picture; some homes also feature a patio and gazebo.

Single Family Residence
Build Type
4
Beds
3.5
Baths
3,500
Sqft
3
Garages
—
Stories

Andover

The Andover is a four-bedroom, three-and-a-half-bath Colonial in the gated Country Woods community at Saint James. A two-story entry foyer opens to formal living and dining rooms, with a gas fireplace in the living room. The kitchen has an island and updated appliances. Upstairs, the main en-suite includes walk-in closets and a bath with a Jacuzzi tub and separate shower. The home also has a finished basement with a wet bar, den, office, egress window, and full bath. Outdoors, a pool, custom waterfall, pavers, and gazebo create a private retreat.

Single Family Residence
Build Type
4
Beds
3.5
Baths
—
Sqft
—
Garages
—
Stories

Bristol

Bristol is a detached single-family home by The Holiday Organization, Inc., with five bedrooms, four bathrooms, and two stories.

Detached single-family home
Build Type
5
Beds
4
Baths
—
Sqft
—
Garages
2
Stories

Brookfield

The Brookfield is a four-bedroom home offering 2,802 square feet and two and a half baths. Described as a fully furnished and beautifully decorated model, it provides a ready-made example of the home’s presentation. Its nine total rooms include the four bedrooms and baths, with the half bath adding convenience beyond the two full baths. The home is in a gated community, and the reported homeowners association fee is $121.51 per month. These details give a sense of the model’s size and basic configuration without prescribing a particular interior arrangement.

Single Family Residence
Build Type
4
Beds
2.5
Baths
2,802
Sqft
—
Garages
—
Stories

Cambridge

The Cambridge is a ranch-style model with 2,200 square feet, three bedrooms, and two and a half baths. Its seven total rooms include the bedroom and bath count, with a half bath in addition to the two full baths. The model is described as to be built in one example, offering a sense of its planned rather than completed presentation there. Reported monthly homeowners association amounts differ, at $121.51 and $107. Together, the available details define the Cambridge as a three-bedroom ranch with a clearly specified footprint and room count.

Single Family Residence
Build Type
3
Beds
2.5
Baths
2,200
Sqft
—
Garages
—
Stories

Castleton

The Castleton is a two-story model with homes described at 5,000 square feet, five to six bedrooms, and three and a half to five and a half baths. Its grand foyer, vaulted ceilings, custom carved staircase, and detailed molding create a striking arrival. One description highlights a volume-ceiling living room with panoramic windows and a wood-burning fireplace, plus a formal dining room, oversized den with patio access, and large kitchen with an island and walk-in pantry. Some homes also feature a paved patio, built-in barbecue, lake views, or guest quarters.

Single Family Residence
Build Type
5–6
Beds
3.5–5.5
Baths
5,000
Sqft
—
Garages
2
Stories

Dartmouth

The Dartmouth is a two-story model with five bedrooms and homes ranging from 5,300 to 5,400 square feet. Bathrooms range from four and a half to five and a half. The interior is described with a dramatic foyer, detailed molding, a grand staircase, and a wood-burning fireplace. A gourmet kitchen with granite and stainless-steel appliances appears in one home, while another features a 20-foot ceiling in the great room, ten-foot ceilings in living areas, and radiant heat. Other described features include a primary en-suite, an upper landing sitting area, and a first-floor guest suite.

Single Family Residence
Build Type
5
Beds
4.5–5.5
Baths
5,300–5,400
Sqft
—
Garages
2
Stories

Eastbrook

The Eastbrook is a two-story model with five bedrooms and homes described with four and a half to five and a half baths. A vaulted 22-foot ceiling and two fireplaces feature in one home, along with a high-end kitchen, hardwood floors, custom millwork, and a first-floor office. Another description highlights a waterfront setting, an intimate courtyard, and dual garages. Its layout includes an open living room and a family room flowing into the kitchen; upstairs, two wings connect by a bridge overlooking the foyer and dining room. Amenities in the community include a clubhouse, pool, tennis, and lakes.

Condominium
Build Type
5
Beds
4.5–5.5
Baths
—
Sqft
—
Garages
2
Stories

Hampton

The Hampton is a three-story model with four to five bedrooms, three and a half to four and a half baths, and homes ranging from 3,505 to 4,665 square feet. A naturally lit two-story foyer leads to a formal living room with a gas fireplace and a formal dining room. One home features an oversized kitchen with a large island, a first-floor bedroom that can serve as an office, and a finished basement. Community amenities include a pool, gym, tennis courts, putting green, paddle boats, and clubhouse. Some homes also have radiant heat in the main bath areas.

Single Family Residence
Build Type
4–5
Beds
3.5–4.5
Baths
3,505–4,665
Sqft
—
Garages
3
Stories

Inverness

The Inverness offers four bedrooms and 2,5 to 3,5 baths in homes ranging from 3,183 to 3,400 square feet. A two-story foyer opens to a free-flowing main floor, with the kitchen looking out to the yard and connecting to a living room with a gas fireplace. Sliding doors lead to a patio. The bedrooms are upstairs, including a spacious primary suite with two walk-in closets; one home’s updated bath includes a steam shower. Custom wood doors and moldings are noted, and community amenities include a clubhouse, pool, gym, athletic courts, and putting green.

Single Family Residence
Build Type
4
Beds
2.5–3.5
Baths
3,183–3,400
Sqft
—
Garages
—
Stories

Kensington

The Kensington is a two-story model with four bedrooms and homes described with two and a half to three and a half baths. The open floor plan begins at a dramatic, 22-foot entry foyer, and the main-level primary suite is a signature feature. A gourmet kitchen opens to the family room and living and dining areas; one home includes a gas fireplace and water views. The plan also features a loft sitting area, and one home has a first-floor office. Descriptions note custom moldings and wood floors, while community amenities include a clubhouse, pool, gym, tennis courts, and lakes.

Single Family Residence
Build Type
4
Beds
2.5–3.5
Baths
—
Sqft
—
Garages
2
Stories

Nantucket

Priced from $1,025,000

Nantucket is a 2,284-square-foot, three-bedroom ranch-style home with two full bathrooms and a powder room, set within The Hamlet Estates’ gated community. Its gourmet kitchen features granite counters and hi-hat lighting, alongside formal living and dining rooms in an open floor plan. The primary suite offers two walk-in closets and an en-suite bath with a separate tub and shower; two additional bedrooms share a full bath. A spacious basement, stone patio, and park-like landscaping add room to relax, while community amenities include a clubhouse, pool, fitness center, tennis, bocce, sauna, and putting green.

Condominium
Build Type
3
Beds
2.5
Baths
2,284
Sqft
—
Garages
2
Stories

Available Home Models

Addison

Single Family Residence
Build Type
4
Beds
3.5
Baths
3,500
Sqft
3
Garages
—
Stories

The Addison is a 3,500-square-foot, two-story home with four bedrooms, three and a half baths, and a three-car garage. Its main level centers on a spacious primary suite with a private bath featuring a separate shower and Jacuzzi tub. The open layout includes a gourmet kitchen, formal living and dining rooms, a library or office, and a den or great room with a fireplace. Upstairs are three bedrooms and a balcony loft. Hardwood floors, a full basement, and community pool and tennis access complete the picture; some homes also feature a patio and gazebo.

Andover

Single Family Residence
Build Type
4
Beds
3.5
Baths
—
Sqft
—
Garages
—
Stories

The Andover is a four-bedroom, three-and-a-half-bath Colonial in the gated Country Woods community at Saint James. A two-story entry foyer opens to formal living and dining rooms, with a gas fireplace in the living room. The kitchen has an island and updated appliances. Upstairs, the main en-suite includes walk-in closets and a bath with a Jacuzzi tub and separate shower. The home also has a finished basement with a wet bar, den, office, egress window, and full bath. Outdoors, a pool, custom waterfall, pavers, and gazebo create a private retreat.

Bristol

Detached single-family home
Build Type
5
Beds
4
Baths
—
Sqft
—
Garages
2
Stories

Bristol is a detached single-family home by The Holiday Organization, Inc., with five bedrooms, four bathrooms, and two stories.

Brookfield

Single Family Residence
Build Type
4
Beds
2.5
Baths
2,802
Sqft
—
Garages
—
Stories

The Brookfield is a four-bedroom home offering 2,802 square feet and two and a half baths. Described as a fully furnished and beautifully decorated model, it provides a ready-made example of the home’s presentation. Its nine total rooms include the four bedrooms and baths, with the half bath adding convenience beyond the two full baths. The home is in a gated community, and the reported homeowners association fee is $121.51 per month. These details give a sense of the model’s size and basic configuration without prescribing a particular interior arrangement.

Cambridge

Single Family Residence
Build Type
3
Beds
2.5
Baths
2,200
Sqft
—
Garages
—
Stories

The Cambridge is a ranch-style model with 2,200 square feet, three bedrooms, and two and a half baths. Its seven total rooms include the bedroom and bath count, with a half bath in addition to the two full baths. The model is described as to be built in one example, offering a sense of its planned rather than completed presentation there. Reported monthly homeowners association amounts differ, at $121.51 and $107. Together, the available details define the Cambridge as a three-bedroom ranch with a clearly specified footprint and room count.

Castleton

Single Family Residence
Build Type
5–6
Beds
3.5–5.5
Baths
5,000
Sqft
—
Garages
2
Stories

The Castleton is a two-story model with homes described at 5,000 square feet, five to six bedrooms, and three and a half to five and a half baths. Its grand foyer, vaulted ceilings, custom carved staircase, and detailed molding create a striking arrival. One description highlights a volume-ceiling living room with panoramic windows and a wood-burning fireplace, plus a formal dining room, oversized den with patio access, and large kitchen with an island and walk-in pantry. Some homes also feature a paved patio, built-in barbecue, lake views, or guest quarters.

Dartmouth

Single Family Residence
Build Type
5
Beds
4.5–5.5
Baths
5,300–5,400
Sqft
—
Garages
2
Stories

The Dartmouth is a two-story model with five bedrooms and homes ranging from 5,300 to 5,400 square feet. Bathrooms range from four and a half to five and a half. The interior is described with a dramatic foyer, detailed molding, a grand staircase, and a wood-burning fireplace. A gourmet kitchen with granite and stainless-steel appliances appears in one home, while another features a 20-foot ceiling in the great room, ten-foot ceilings in living areas, and radiant heat. Other described features include a primary en-suite, an upper landing sitting area, and a first-floor guest suite.

Eastbrook

Condominium
Build Type
5
Beds
4.5–5.5
Baths
—
Sqft
—
Garages
2
Stories

The Eastbrook is a two-story model with five bedrooms and homes described with four and a half to five and a half baths. A vaulted 22-foot ceiling and two fireplaces feature in one home, along with a high-end kitchen, hardwood floors, custom millwork, and a first-floor office. Another description highlights a waterfront setting, an intimate courtyard, and dual garages. Its layout includes an open living room and a family room flowing into the kitchen; upstairs, two wings connect by a bridge overlooking the foyer and dining room. Amenities in the community include a clubhouse, pool, tennis, and lakes.

Hampton

Single Family Residence
Build Type
4–5
Beds
3.5–4.5
Baths
3,505–4,665
Sqft
—
Garages
3
Stories

The Hampton is a three-story model with four to five bedrooms, three and a half to four and a half baths, and homes ranging from 3,505 to 4,665 square feet. A naturally lit two-story foyer leads to a formal living room with a gas fireplace and a formal dining room. One home features an oversized kitchen with a large island, a first-floor bedroom that can serve as an office, and a finished basement. Community amenities include a pool, gym, tennis courts, putting green, paddle boats, and clubhouse. Some homes also have radiant heat in the main bath areas.

Inverness

Single Family Residence
Build Type
4
Beds
2.5–3.5
Baths
3,183–3,400
Sqft
—
Garages
—
Stories

The Inverness offers four bedrooms and 2,5 to 3,5 baths in homes ranging from 3,183 to 3,400 square feet. A two-story foyer opens to a free-flowing main floor, with the kitchen looking out to the yard and connecting to a living room with a gas fireplace. Sliding doors lead to a patio. The bedrooms are upstairs, including a spacious primary suite with two walk-in closets; one home’s updated bath includes a steam shower. Custom wood doors and moldings are noted, and community amenities include a clubhouse, pool, gym, athletic courts, and putting green.

Kensington

Single Family Residence
Build Type
4
Beds
2.5–3.5
Baths
—
Sqft
—
Garages
2
Stories

The Kensington is a two-story model with four bedrooms and homes described with two and a half to three and a half baths. The open floor plan begins at a dramatic, 22-foot entry foyer, and the main-level primary suite is a signature feature. A gourmet kitchen opens to the family room and living and dining areas; one home includes a gas fireplace and water views. The plan also features a loft sitting area, and one home has a first-floor office. Descriptions note custom moldings and wood floors, while community amenities include a clubhouse, pool, gym, tennis courts, and lakes.

Nantucket

Priced from $1,025,000

Condominium
Build Type
3
Beds
2.5
Baths
2,284
Sqft
—
Garages
2
Stories

Nantucket is a 2,284-square-foot, three-bedroom ranch-style home with two full bathrooms and a powder room, set within The Hamlet Estates’ gated community. Its gourmet kitchen features granite counters and hi-hat lighting, alongside formal living and dining rooms in an open floor plan. The primary suite offers two walk-in closets and an en-suite bath with a separate tub and shower; two additional bedrooms share a full bath. A spacious basement, stone patio, and park-like landscaping add room to relax, while community amenities include a clubhouse, pool, fitness center, tennis, bocce, sauna, and putting green.

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Community Facts

  • Community Name: The Hamlet Estates
  • Neighborhood: Smithtown
  • Year Established: 2008
  • Total Homes: 167 residences
  • Property Type: Houses, Townhomes
  • County: Suffolk, NY county
  • Available Sales Listings: 2
  • Available Rental Listings: 0
  • Lifestyle & HOA: Life at The Hamlet Estates at Saint James is centered on ease, recreation, and community connection. Residents enjoy access to an impressive collection of amenities designed to support an active and social lifestyle, including a luxurious clubhouse with gathering spaces, a swimming pool and spa, lighted tennis courts, a fitness center, basketball court, bocce court, playground, putting green, and two scenic lakes with paddle boats. The Homeowners Association maintains common areas, amenities, and shared infrastructure, allowing residents to enjoy a low-maintenance lifestyle within a well-cared-for community. Visitor parking and open spaces further enhance the ease and functionality of everyday living. With its gated setting, wide range of amenities, and convenient location near North Shore beaches, parks, and village centers, The Hamlet Estates at Saint James offers a lifestyle that feels both relaxed and refined, an inviting place to call home for those seeking comfort, recreation, and a strong sense of community.

Frequently Asked Questions

Learn more about the The Hamlet Estates community and available homes for sale and rent here in Saint James.

When was The Hamlet Estates built?
The Hamlet Estates was built in 2008.
Where is The Hamlet Estates located?
The Hamlet Estates is located at 5 Hamlet Woods Dr in Saint James in NY.
What amenities does the The Hamlet Estates community provide?
The Hamlet Estates provides the following resident amenities: Basketball Court, Clubhouse, Fitness Center, Gated Community, Grounds & Common Area Maintenance, Pool, Spa, Tennis Court, Waterfront Access.
What county is The Hamlet Estates located in?
The Hamlet Estates is located in Suffolk, NY county.
How many homes are currently available in The Hamlet Estates for sale or for rent?
Out of 167 homes in The Hamlet Estates, there are currently 2 sales listings and 0 rental listings available.
What is the average square footage in the The Hamlet Estates community?
The average square footage of homes in The Hamlet Estates is 1768 sq.ft.
How big is the The Hamlet Estates community?
The The Hamlet Estates community is made up of 167 homes with an average lot size of 16896 sq.ft.

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