The Matthews Team

William Raveis Lifestyles Realty

Highland Lake Real Estate

Highland Lake Homes for SaleFind current listings for Highland Lake real estate below. You may also be interested in viewing available Litchfield County lakefront homes.

Browse Highland Lake CT Homes for Sale

Contact the William Raveis Lifestyles Team at 860-868-0511 or online with any questions or to schedule a private tour.

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262 Perch Rock Trail Winchester CT 06098
Pending Continue to Show

MLS Number 170509862

  • Single Family
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 4,416
  • Acreage 0.24

Your own oasis on the lake! Lovingly renovated waterfront home with western exposures on highly sought-after Highland Lake. As you walk into the grand foyer with cathedral ceilings and a newly built staircase, you are greeted by a living room with floor to ceiling tinted windows overlooking the lake. The main floor has a newly remodeled kitchen with Cambria quartz countertops, custom-built cabinets, high-end stainless-steel appliances, and an expansive island. The upper level boasts a brand-new primary suite, sitting area, with a separately designated walk-in closet and laundry. A brand new luxurious bathroom with custom-made Italian vanities, marble countertops and expansive shower with upgraded low iron frameless glass. Two of the three large upstairs bedrooms have water views! The lower level family room and bedroom walks out to a newly built stone covered sitting area with an outside television and bar for those rainy days and direct water front patio with a new dock and stairs to enter lake. City water/sewer with new high efficiency heating and cooling system and propane whole house generator! Make this place your summer home or live here all year round! Full list of renovations available upon request.

Listed by Jon Sheaffer of Sheaffer & Company Real Estate LLC

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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552 East Wakefield Boulevard Winchester CT 06098

MLS Number 170509036

  • Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,764
  • Acreage 0.28

Escape to paradise! The property is in the 3rd bay sunny eastside of Highland Lake. A 444-acre lake in Winchester, CT. Just a 30+ min drive to Bradley or appr 2 1/2 hours from NYC or Boston. Just 4 miles from Route 8. This is the lake house of your dreams. Magnificent lake views from every room in the house with a different sunset every night. Something for everyone. A large upper deck to enjoy the sun and a covered patio to enjoy the lake in the shade. Drive your car into the garage and it is just 2 steps into the great room which is open to the dining area and center isle kitchen. Upstairs you will find the master suite with full bath and walk in closes along with two modestly sized bedrooms and another full bath. The lower level features a family room with a fireplace (easily converted to a gas log set) a gorgeous full wet bar with a slider out to the covered patio and just a few steps to the lake. The dock is permanent (no in and out) and the sea wall is gunite (less maintenance). There is a utility shed to hold all your water toys/yard equipment and a small cottage is now used for storage but could be a future quest house. Plenty of off-street parking. The property has a boat lift and jet ski lift permit. Owner and agent related.

Listed by Frank C Carfiro of Northwest CT Realty

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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132 Spencer Hill Road Winchester CT 06098

MLS Number 170207910

  • Land
  • Acreage 82
  • Zoning R-1

Very special land parcel. Western views overlooking Highland Lake. Pastures, fields, stone walls, brook & wooded areas showcase this wonderful building site. Ideal single family or subdivision potential. Land is actual several parcels on both Spencer Hill Rd and Spencer St totaling 81 +/- acres, Sewer & water nearby, but not yet permitted. Taxes and assessment are for both parcels.

Listed by Stephen M Drezen and Karen Newton of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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229 West Wakefield Boulevard Winchester CT 06098

MLS Number 170525022

  • Single Family
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,305
  • Acreage 0.39

Waterfront Property!! This spectacular 4 bedroom, 2 bath waterfront home is the luxury year-round lake house of your dreams! Situated on the west side of Second Bay at Highland Lake, this home has unobstructed water views and features a flat, level waterfront lot with over 70 ft of shorefront. Easy access to the water with sandy beach entry. Located in Winchester, Litchfield County CT you can spend your days enjoying all the activities this boating lake has to offer. Meticulously and fully renovated in 2016, this stunning home exemplifies great design. With hardwood floors, state of the art kitchen and bathrooms, a 1-year old roof, central air, fireplace, new windows and doors, all you need to do is move right in! The home's open concept floor plan and spacious living area make entertaining easy as you take in the unobstructed lake views. The eat-in kitchen boasts stainless steel appliances as well as beautiful quartz countertops. The gorgeous sunroom is another ideal spot to take in the beautiful vistas over Highland Lake. Upstairs there are 4 bedrooms and the sprawling primary bedroom is sure to be a serene lakeside retreat. First floor laundry, a generator, a security system, and auxiliary water pump ensure your only worry will be having fun and making memories to last a lifetime. Plenty of storage throughout. With all furnishings included, you can move into this stunning property immediately and have the beautiful clean water of Highland Lake right outside your door!

Listed by Kate D'addabbo of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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232 Perch Rock Trail Winchester CT 06098

Winchester, CT232 Perch Rock Trail

Price$775,000

Est. Mortgage: $/month

MLS Number 170526283

  • Multi Family Multi-Family For Sale
  • Square Feet 1,836
  • Acreage 0.14

LOCATION! LOCATION! LOCATION! This 4 bed, 2 bath, 4 season home is located on a quiet side street directly on Highland Lake. Public records list it as a 2 family home, there is no second kitchen and it has been used as a single family by current owner. Near major travel routes and just a couple hour drive to New York or Boston. Highland Lake offers year round beauty and recreation in the quiet Northwest Corner of Connecticut. This home could be gutted and renovated or torn down and the footprint used to build your lakeside dream home.

Listed by Debbie Videtto and Darcy Abbott of Berkshire Hathaway NE Prop.

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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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268 Perch Rock Trail Winchester CT 06098
Pending Continue to Show

MLS Number 170511074

  • Single Family
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 972
  • Acreage 0.16

Welcome Home to Highland Lake! A great place to work and play. Whether you need a home office with an amazing view or just a place to rest and relax or both, this 4-season Lakefront property has it all. The private setting is off the main road with an ample yard, plenty of parking and an attached carport. This home includes central air, pellet stove, fireplace and a generator that is turnkey ready. On the lakeside, steps lead right into the water to cool off on a hot day and a dock where you can fish and moor your boat. The unfinished basement has potential for more living space. The sunset views are waiting for you!

Listed by John Mahoney of Northwest CT Realty

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$
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$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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537 West Wakefield Boulevard Winchester CT 06098

MLS Number 170519639

  • Single Family
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1,781
  • Acreage 0.23

Welcome to the Highland Lake community! Enjoy this well-maintained home that is situated on a quiet street with a private yard. You will find a well thought out and versatile floor plan. This beautiful home has gorgeous views of the lake all year round. The updated kitchen with granite countertops has an open concept eating and entertaining space. There is a bedroom and full bath on the main level and a second bedroom and full bath on the second level. The lower level can be another bedroom, office, gym. The upper-level loft is being used as a reading room but, is a transitional space that can serve many different options. The lower level includes a laundry room and half bath. Enjoy lakeside living featuring a marina, beaches, local shops, restaurants, state parks and ski slopes all a short drive away.

Listed by Solidea Pitruzzello of Berkshire Hathaway NE Prop.

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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817 East Wakefield Boulevard Winchester CT 06098

MLS Number 170498508

  • Single Family
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,051
  • Acreage 0.62

This is the one you've been waiting for! This amazing home is beautifully situated on a quiet, private lot providing incredible views of Highland Lake. Walk across the street to your own private dock and waterfront property to enjoy all lake living has to offer and retreat to your deck for a perfect dinner view. If you prefer to stay indoors and enjoy the lake view, get comfortable in the sunroom or sunken dining room and enjoy the views. Updated kitchen, main level washer and dryer access, and main floor bedroom off the living room make everything easy. Wake up to the lovely view of the lake from the second floor bedroom if you prefer. Composite deck leads to enclosed "pool house" for hot tub. Private, wooded backyard area, Oil,wood and coal fired furnace, shed and back porch are even more reasons to make this the perfect year round or vacation home. Schedule your showing TODAY!!!!

Listed by Patricia Careddu of Sullivan Real Estate Inc

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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20 Laurel Street Winchester CT 06098
Active With Contract

MLS Number 170515886

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,459
  • Acreage 0.64

All the work has been done! Lovingly cared for Cape with 3-4 Bedrooms, 2 Baths and an oversized garage, three season room. Walking distance to Highland Lake. Property includes extra lot located on Boyd St. Taxes and Acreage are for both properties. Keep the lot for a larger yard or potential building. Level yard and driveway, full basement with hatch. This home has it all!

Listed by Kelly Sullivan and Austin Brochu of Sullivan Real Estate Inc

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7 Arbor Ridge Road Torrington CT 06790

Torrington, CT7 Arbor Ridge Road

Price$289,500

Est. Mortgage: $/month

MLS Number 170511818

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1,936
  • Acreage 0.39

Location, location, location! Desirable East end Hi-Ranch located at the end of a cul-de-sac in Arbor Ridge. This gem features 3 bedrooms, 3 FULL baths, large eat in kitchen, open living room with cathedral ceilings, hardwood floors and lots of natural sunlight. Finished lower level with laminate flooring, currently being used as an office and can be converted into a 4th bedroom or in law apt. The 2 bay OVERSIZED garage has plenty of storage and both doors have been recently replaced! Outside features a vinyl fence which was installed in 2019 for added privacy. The back yard is exceptionally peaceful. Solar panels were installed in 2019, draw 104% of power and the sellers will have them paid off in full at closing! In addition to having only a $10/month electric bill, never lose power as the home has a FULL house generator hook up installed in 2012. Conveniently located to shopping, fitness center, walking trail. Only 2 miles from greenwoods Country Club and 4 miles from Highland Lake where you can swim, motor boat, fish and more! Great commuter location less than 2 miles to Rt 8. A little cosmetic love will go a long way! Make your dreams come true! Don't miss this wonderful opportunity, schedule your showing today!

Listed by Anthony Gioia of The Washington Agency

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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100 Hurlbut Street Winchester CT 06098

Winchester, CT100 Hurlbut Street

Price$244,900

Est. Mortgage: $/month

MLS Number 170524374

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,539
  • Acreage 0.23

Welcome to Highland Lake! This 3 bedroom Cape is so close to the lake, you can see it from the end of the driveway. It is located in close proximity to Resha Beach, just up the street from The Marina, and directly across the street from a natural spring. Inside you'll enjoy hardwood floors and a newly redone first floor bathroom. One of this home's bedrooms is conveniently located on the first floor while the other two are on the upper level. The primary bedroom has an attached additional room which may be used as additional storage, large closet, office, or just about anything else you can come up with. With the walk-up attic and full basement, you won't run out of storage space. This home features a one-car garage, private back yard, and is generator ready.

Listed by Jeffrey Liskin of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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129 Maloney Court Winchester CT 06098
Active With Contract

MLS Number 170521152

  • Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,618
  • Acreage 0.35

Adorable move in ready Ranch in a great neighborhood with open concept Living room/Eat in Kitchen combo. Living room has a fireplace insert. Master bedroom has a walk in closet; another good sized bedroom and a 3rd bedroom that is currently being used as an office. Downstairs/basement area has potential to be used as an in-law suite or one big family room that has a full bath along with a sectioned off laundry/storage room. The Navien tankless water system is only 1.5 years new! Walk out access to the back yard that has a partially flat and cleared area as well as additonal wooded acreage. Nice sized deck big enough for table and chairs and a grill. Front yard is all fenced in with a doggie door on the front door to give your pet(s) easy access to come and go safely. The roof is only 6 months old!! Solar panels are newly activated and ready to save the new owners money with the plan in place the new owners will take over. House is being "sold as is". Highland lake is only a 2.5 mile drive. Defintely worth your time to come and take a look! Book your showing now!

Listed by Maria P Smith of Turning Point Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.7% last updated on Sep 29, 2022
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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