Gaylordsville CT Real Estate & Homes for Rent

Now leasing a top floor apartment in the premier rental residence located in the heart of Pawling. Styled in the character of Pawling's iconic Dutcher House & newly completed, it offers a unique opportunity to live in sophisticated elegance with fine finishing & details throughout. The theme is modern luxury set in a quaint upstate, bucolic 18th century village. The 4th floor apartment boasts an open floor plan between the kitchen, dining & living room. Lavish luxuries like oak hardwood flooring, soft-close custom cabinetry, granite counters, stainless steel GE appliances, multi zone heat & air, and an in-unit washer & dryer set these units apart from anything on the market. The secure building features an intercom system, well-lit hallways, elevator & sprinkler system. On Main Street in the charming Village of Pawling with fine dining, boutique shops, cultural attractions and numerous outdoor activities. Pawling's Metro North train station, and two private offsite parking lots all within walking distance.

This charming country Cape in the heart of Washington Depot is now available for rent after a considerable remodel. The home sits on just under 2 acres in a quiet setting, yet is walking distance from the center of town. Each of the main level's rooms are bright and well sized. The eat-in kitchen features marble counters, stainless steel appliances, a breakfast nook, and is adjacent to the dining room with built in cabinets. Off of the kitchen is a beautiful screened in porch with a bluestone floor, and a brand new full bath near the rear entrance.The opposite side of the main level consists of a large living room with a gas fireplace, built ins, and French doors leading to the back yard and porch. Additional windows were also added to produce even more natural light. Adjacent is a cozy den with a pullout couch that could be used as a 4th bedroom. The upper floor includes three bedrooms and 2 full bathrooms. The primary bedroom has a brand new full bathroom, equipped with a spacious shower and radiant marble floors. The two additional bedrooms are bright and comfortable, and a full bath in the hallway accommodates the two rooms. Hiking in Steep Rock Preserve, The Frederick Gunn School, and Washington's beautiful Lake Waramaug are all just minutes away. Shopping or dining in the Depot is less than half a mile and can be reached by car or on foot. Only 35 minutes to Metro North trains and 90 minutes to Manhattan. June & July at $11,500 per month. Off Season $7,000 per month.

AVAILABLE AUG 1- AUG 31 2024 @ $32,000. Chic Riverfront Summer rental. 4 bedroom 3 1/2 baths on a quiet street close to Steep Rock Land Trust's hiking trails and minutes from Washington Depot. Open floor plan, hardwood floors throughout, top of the line chef's kitchen w/ butler's pantry. 2 first floor bedrooms with jack-and-jill bath. 2 bedrooms upstairs, each with full baths, finished lower level. Covered porch and flagstone terrace, Heated gunite pool and Generator. Perfect country retreat with easy access to NYC.

Available only for the month of July, 2024. Adorable, uber-chic and gorgeous July 2024 rental walking distance to the center of much-desired Washington Depot, on a quiet street near the entrance to miles of hiking trails in Steep Rock Preserve. Fully renovated and updated in 2023, 4 BR and 3 full baths, PLUS the party barn with a sleeping loft, kitchenette and full bath can sleep four more people (beds not provided in barn). Heated salt water gunite pool, beautiful stone walls, lovely front porch from which to watch the sunrise. Truly a place for anyone wishing to get away to paradise.

AVAILABLE JAN 16- MAR 31 2024 @ $7,500. Chic Riverfront winter rental. 4 bedroom 3 1/2 baths on a quiet street close to Steep Rock Land Trust's hiking trails and minutes from Washington Depot. Open floor plan, hardwood floors throughout, top of the line chef's kitchen w/ butler's pantry. 2 first floor bedrooms with jack-and-jill bath. 2 bedrooms upstairs, each with full baths, finished lower level. Covered porch and flagstone terrace, Whole house Generator. Perfect country retreat with easy access to NYC. Close to Mohawk Ski area.

Nestled on a country hillside you will find the summer sanctuary you've been looking for. It calls for you while boasting eagle eye views of both Lake Waramaug and The Berkshires. Rejuvenate through the day immersed at gorgeous Warren Town Beach or Macricostas Preserve, a favorite hike of CT Magazine. Seeking more trails, Steep Rock will lend you access to a 235' train tunnel and Hidden Valley Preserve offers Thoreau Bridge. Unwind at a local favorite Hopkins Vineyard with tastings and festivities through the season. This wonderful property is being offered at a rate of $20,000. for the month of August. Pets will be considered. Secure your summer retreat and reach out to schedule your private tour today.

This won't last. HEAT INCLUDED , 2 bedroom , Living room, Kitchen and bath. Close To Town Center, Shopping & Dining. First months rent and 2 months security(unless over 65). Credit and back ground check should have around a 600 credit score. Please use our rental application and Venmo on bottom for the credit check $30 per person over 18 living in the unit. NO PETS, NO SMOKING

Boar House is an extraordinary property set on 4.72 acres bordering Steeprock Preserve. Redesigned and expanded by noted neoclassical Charleston architect, Randolph Martz, this spacious and elegant house offers 5 bedrooms, 5 1/2 baths & over 4,900 sq ft of living space. Both the formal living and dining rooms are impressive with high ceilings, fireplaces and floor to ceiling windows. The renovated gourmet chef's eat-in kitchen includes a large work area , honed granite counters and SubZero and Viking appliances. The kitchen enjoys the view of the tranquil setting of the formal gardens through multiple picture windows. Just around the corner is the charming library/family room with window seat and wetbar. The first of two main floor bedrooms has a full bath, walk-in closet and French doors to the private deck. The second bedroom has built-ins and full bath. The primary bedroom is privately located on the second floor and has a fireplace, marble bath, and large dressing room. There are two additional ensuite bedrooms on the second level. Through a separate exterior entrance is a detached finished space including office & entertainment area and full bath. There is an audio system and a whole house generator. The grounds are magnificent with in ground heated pool, professionally designed gardens, brick & bluestone walkways, stonewalls, terrace with pergola. There is a playhouse, trampoline, soccer goal, and direct access to Steep Rock hiking trail. Available for the month of July

Pristine Arts & Crafts Carriage House. Perfect setting on Washington's Historic Green surrounded by the Frederick Gunn School and historic shingle-style Rossiter mansions. Ground floor ensuite primary bedroom, office with sleeper sofa and cozy den with wood-burning fireplace. Upstairs, king bedroom with ensuite bath, large living room, dining room and eat-in kitchen. Fabulous mahogany deck for barbequing. Wonderful walking or biking neighborhood near the Gunn Library & Museum, churches, a caf?, and the Steep Rock Land Preserve. Beautiful neighborhood views. SUMMER June - August $15,900/month; Memorial - Labor Day $39,900 OFF-SEASON September - May $10,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $109,000. Inquire about other/shorter rental terms.

AVAILABLE SEPT 3, 2024 THRU MAY 30 2025 @ $7,500 PER MONTH. Quintessential CT Country Off-Season rental. Pristine 3 bedroom main house with 3.5 baths is perfect for entertaining. The home is nestled on 21+ acres with new circular driveway, large expanses of lawn, mature trees. Gourmet kitchen, formal dining room, living room with fireplace, large sun room. Covered back porch with comfortable sitting area and outdoor dining. Conveniently located close to town, The Mayflower Inn, tennis courts, fine dining and chic shopping. Walk across the street to Steeprock hiking trails. 25 minutes to Mohawk Mountain Ski area and 1.5 hours to NYC. Also available annually @ $10,000 per month beginning Sept 3, 2024.

AVAILABLE ANNUALLY starting Sept 3, 2024 @ $10,000 PER MONTH. Quintessential CT Country annual rental. Magnificent over-sized pool of 50' x 20' with spa, cabana with a full bathroom, changing room, kitchenette and outdoor grill. Pristine 3 bedroom main house with 3.5 baths is perfect for entertaining. The home is nestled on 21+ acres with new circular driveway, large expanses of lawn, mature trees. Gourmet kitchen, formal dining room, living room with fireplace, large sun room. Covered back porch with comfortable sitting area and outdoor dining. Conveniently located close to town, The Mayflower Inn, tennis courts, fine dining and chic shopping. 25 minutes to Mohawk Mountain Ski area and 1.5 hours to NYC. Also available $7500 per month Sept 3, '24 - May '25.

Set in one of the most beautiful areas of Roxbury and short walk to acres of land trust, this light, bright and airy open floor plan 18th century Colonial has over 26 acres of peace and quiet. There is a large tranquil pond which is surrounded by white pine trees. A place to one with nature! The home features 2 primary bedrooms, one on each level and an additional bedroom on the second level. The designer kitchen with Carrara marble counters, a vaulted ceiling and custom island opens to a stone patio and screened porch. The huge living room is light filled with wide board floors, French doors and a wood burning fireplace. This home also features central air conditioning, a security system, first floor laundry. Enjoy the sites and sounds of nature in this very special retreat property and relax in this paradise, under 2 hours from New York City.

This lovely Cottage in Inglenook is super charming and ready for you to move in! Tucked away on a private lot with level land, this 2 Bedroom 1 Bath is renovated and ready to go. The Open Living Room/Dining Room offers great space and is nicely furnished. The Kitchen offers new cabinetry and appliances. Primary Bedroom with French doors out to your own private deck. 2nd Bedroom with a closet and a full bath complete the home. Enjoy the outdoors on the expansive deck. This home is available furnished either for the summer, short term, or year round. Very good credit.

A special setting! Five-room cottage in excellent condition, privately situated on a working farm. Free picking provision of sweet corn and garden vegetables when in season. Ideal for someone who enjoys farm activity and country living. No smoking allowed in cottage. A pet dog will be considered on a case-by-case basis. References and credit report required.

AVAILABLE Sept 2024 - May 2025 @ $6,500 PER MO Top Washington location. Five bedroom main house plus 2 bedroom, 2 bath guest house. Plenty of flat land. Pond for fishing/skating. Media room/cabana with foosball. Gym and lighted paddle ball court will keep you busy and in shape. Spacious kitchen opens to stone terrace with bbq. 30 Minutes to Mohawk Mountain Ski Area. Tenant pays for utilities, weekly lawn care and housekeeping. Landlord pays for alarm service, pest control, additional gardening expenses. Inquire for addl time

Available from Memorial Day to Labor day at $7,000/month. Escape to this charming 2-bed, 1-bath summer rental retreat nestled on the shores of Candlewood Lake. This newly remodeled home offers the perfect escape from the hustle and bustle, just 90 minutes from NYC. Step inside to discover a cozy, casual living space filled with natural light and a welcoming ambiance. The open layout seamlessly connects the living area to the kitchen, creating a warm and inviting atmosphere. The kitchen boasts lake views, ample cabinet space, and a convenient layout, making meal preparation a breeze. The two bedrooms provide comfortable accommodations, each offering a peaceful sanctuary to relax after a day of lakeside adventures. Outside, the private waterfront yard and dock provide plenty of space for outdoor enjoyment and entertaining. Whether you're savoring morning coffee by the lake or hosting friends in the spacious waterside yard, this property offers the ideal setting for making lasting memories. Embrace the tranquility of lakeside living and take advantage of the nearby recreational activities, including miles of hiking in Squantz Pond State Park (a minute away), and exploring all that Northern Fairfield and Litchfield Co. have to offer. Don't miss this opportunity to experience the ultimate summer getaway in this beautifully remodeled home. Discover the perfect retreat at 11 Bogus Hill Road and create unforgettable summer memories in this idyllic lakeside setting.

Available from Memorial Day to Labor day at $21,000 for the entire term. Escape to this charming 2-bed, 1-bath summer rental retreat nestled on the shores of Candlewood Lake. This newly remodeled home offers the perfect escape from the hustle and bustle, just 90 minutes from NYC. Step inside to discover a cozy, casual living space filled with natural light and a welcoming ambiance. The open layout seamlessly connects the living area to the kitchen, creating a warm and inviting atmosphere. The kitchen boasts lake views, ample cabinet space, and a convenient layout, making meal preparation a breeze. The two bedrooms provide comfortable accommodations, each offering a peaceful sanctuary to relax after a day of lakeside adventures. Outside, the private waterfront yard and dock provide plenty of space for outdoor enjoyment and entertaining. Whether you're savoring morning coffee by the lake or hosting friends in the spacious waterside yard, this property offers the ideal setting for making lasting memories. Embrace the tranquility of lakeside living and take advantage of the nearby recreational activities, including miles of hiking in Squantz Pond State Park (a minute away), and exploring all that Northern Fairfield and Litchfield Co. have to offer. Don't miss this opportunity to experience the ultimate summer getaway in this beautifully remodeled home. Discover the perfect retreat and create unforgettable summer memories in this idyllic lakeside setting.

AVAILABLE June 18th - July 14th at $20,000 and/or Aug 13th - Sept 9 at $20,000 Top Washington location. Five bedroom main house with central air plus 2 bedroom, 2 bath guest house with window units. Gunite heated pool, pond with boat/fishing, media room/cabana with foosball. Gym and lighted paddle ball court will keep you busy and in shape. Expansive high end kitchen opens to stone terrace with bbq. Tenant pays for utilities, weekly pool maintenance, lawn care, garbage, and housekeeping. Landlord pays for alarm service, pest control, additional gardening expenses.

Unique Raised Ranch, located privately on 2 acres in a lovely, rural setting, surrounded by an estate & a horse farm. This special home has been completely renovated to perfection this year, nothing is left of the original house. New windows, electric fplc, new Trex deck, stunning new chef's kitchen w/quartz counters & stainless appliances, opened up to the dining area, new flooring thruout, new bathrooms, it's all been refurbished. There is a whole house propane generator, central air & electric heat pump for heat. There are 3 BR's, an office, a family room, the lower bathroom opens to a laundry w/access to the garage. There is a new blacktop driveway & a new path to the back of the property. This home is unique & wonderful, not to mention how close it is to the Village, the train & highways. The location couldn't be better! Tenant pays all utilities, mowing & plowing. Tenants must fill out application, credit score 700 or more, Rent Spree for background & credit is $20 each.

This beautifully renovated Revolutionary War Era home is a rare find in Dutchess County. It is a cherished gem from the Georgian period and is highly regarded in the Millbrook region. Situated on a spacious, manicured and private 120-acre property overlooking a pond, the updated home offers all the amenities needed for a perfect summer vacation in upstate New York. An oversized family room makes for memorable gatherings, the expansive eat-in kitchen opens up to a covered porch, gardens (enhanced with recent plantings), and an inviting inground saltwater pool; perfect for cooling off in the summer heat. Additionally, there is a gym for those who enjoy staying active. Enjoy a large primary suite and four well-appointed guest bedrooms and 5.5 bathrooms. For those who love to entertain, the formal dining room and library are perfect spaces for hosting summer gatherings, as is the outdoor patio for entertaining and al-fresco dining. Upon request, there is also a newly refurbished apartment available. The downtown area of Millbrook and the Dover Plains train station are just a short distance away, adding to the convenience and charm of this exceptional property.

Fantastic Candlewood Lake direct waterfront summer rental. Available between May 23 and September 5,2024, this home will allow your family to create long-lasting memories (seasonal or extended use). The views of the lake are spectacular. There is a private boat dock and access to two private sandy beaches on the property. Gorgeous open floor plan. The home offers 4 bedrooms and 3.5 baths. Primary bedroom with beautiful lake view & offers luxury en-suite with large soaking tub and oversized walk in shower. All bathrooms offer quality fixtures. Gourmet kitchen with a six burner Viking stove, Sub-Zero refrigerator, Bosch microwave & oven. Living room with wood burning stone fireplace, two story windows overlooking the lake & similarly high ceilings. Home office as well as an incredible play room with a gas fireplace, air hockey table & shuffleboard. Large windows throughout the home. All hardwood floors. Main level laundry. Playground and patio overlooking the lake. A great getaway for the season, but easy access to major shopping, dining, services and interstate. Owner to pay all utilities and maintain lawn. 4 car tandem garage, room to sleep 9. $25,000/monthly rent between May 23-Sept 5,2024 or $87,500 for the season. Additional time available.

Spacious one bedroom accessory apartment located off a quiet country road in a beautiful setting. Great natural light, new windows, new bamboo floors. Sliding doors off the living room lead to a deck and fantastic yard. The primary bedroom has a large en-suite full bathroom. Nice sized kitchen, separate laundry room with washer and dryer and half bath complete the unit. Heat is included in the monthly rent. Pets are welcome. The unit has 200 amperage service and central air conditioning. Storage available in the attic. Ideal location, five minutes to Metro North, restaurants, and shopping in Wassaic and Amenia. Less than 15 minutes to Kent, CT another chic fabulous town with shopping, stores, and restaurants.

Summer 2024 $20k June, $25k July & August $30k. This historic center hall colonial is located on 40 acres has modern day amenities including a large Chef's kitchen and a full first floor bathroom. The spacious dining room seats up to 12. The large 2nd floor primary suite features a newly renovated bath and private lanai which overlooks the pool and ponds. There are two additional bedrooms on this floor with a new marble bath & a laundry room with built-ins. The third floor contains 2 additional bedrooms that share a marble bath. There is a den with large screen t.v. and wood burning stove, a formal living room with a gas fireplace and a 4 season sunroom with heated floor, breakfast table and lounge furniture. The property is completely private for your enjoyment and utterly whimsical with a large, heated pool set amid nature with views of the pond and ridge-line. Amazing western sunsets with sun on the pool until 8pm. Quintessential country living at its best.

Featured in CTC & G January, 2024 Issue! Striking Modern Renovation of Artist's home in private, much sought after location in the rural Litchfield Hills. On a quiet country road, surrounded by woodlands, this 1 bedroom/ 1 bath apartment, is located beneath the main house and may be rented with the Main House or completely closed off on its own with own laundry room. Ideally situated for hiking and birding in the thousands of acres of Roxbury Land Trust & Steep Rock Preserves. Lake activities and near by the Shepaug River, local farmstands, local fairs, antiquing, cultural venues as well as wonderful restaurants and shops. Golf and tennis nearby. This home is close to the charming Town of Roxbury, minutes to Washington Depot and 90 minutes from NYC. RATES FOR LABOR DAY TO MEMORIAL DAY, 2024/25 as follows: 1 BR apt- $2,000/month or whole house-$5,250. SUMMER MONTHS, 2024:1 BR Apt- $2,700 or whole house-$7,850. Plus, utilities & $300 cleaning fee. Inquire for shorter or longer stays. Must See! Main House listed separately as MLS #170623403.

Featured in CTC & G January, 2024 Issue! Striking Modern Renovation of Artist's home in private, much sought after location in the rural Litchfield Hills. On a quiet country road, surrounded by woodlands, this 3-bedroom, 2 bath home rests on five acres with a gentle stream running through it. State of the art chef's kitchen with all new appliances including a wine cooler. Great Room with beams, soaring ceilings, hardwood floors and wood-burning fireplace. Outdoor deck for relaxing and listening to the quiet rush of the stream. Fully-fenced backyard, BBQ Grill, Fire Pit. Central Air. Ideally situated for hiking and birding in the thousands of acres of Roxbury Land Trust & Steep Rock Preserves. Lake activities and near by the Shepaug River, local farmstands, local fairs, antiquing, cultural venues as well as wonderful restaurants and shops. Golf and tennis nearby. This home is close to the charming Town of Roxbury, minutes to Washington Depot and 90 minutes from NYC. NB: This listing is located above a 1 BR apartment, which is currently closed off from the Main House. You have your own private front door entrance, deck and washer and dryer. RATES FOR LABOR DAY-MEMORIAL DAY as follows: Main House- $4,000/mth ADD 1 BR apt- $5,250. SUMMER MONTHS, 2024: MAIN HOUSE -$6,000 ADD 1 BR Apt- $7,850. Plus, utilities & $300 cleaning fee. Inquire for shorter or longer stays. Must See! One bedroom apartment listed separately as MLS #170623688